Luxury Homes in Winter Park

Properties

In the exclusive community of Windsong on Lake Berry, this magnificent 1.6-acre gated Mediterranean estate is a private oasis. With over 11,000 square feet of living area and a beautifully landscaped lakefront lot, this residence offers an exceptional blend of elegance, charm and privacy rarely found in Winter Park. The home features seven spacious bedrooms and nine full and two half baths. Entertain in the all-glass conservatory, dedicated theater room with motorized seating and a fully equipped game room. Modern conveniences throughout including gas-powered generators, an elevator and dumbwaiter. Two above-garage apartments provide ideal accommodations for guests and family. Outdoors, enjoy an expansive covered lanai, infinity edge pool and spa, boat dock with jet ski lift, and a summer kitchen complete with wood-burning fireplace, gas grill, refrigerator and icemaker, all overlooking the beautifully landscaped yard and lake. With its private gated entrance, this home is a one-of-a-kind opportunity to enjoy all the amenities Winter Park and Windsong have to offer.

$8,950,000 Active

1120 Preserve Point Drive Winter Park, Florida

7 Beds 11 Baths 11,255 SqFt 1.63 Acres

Under Construction. Opportunities like this rarely present themself, just a eight-minute walk from the iconic shops, restaurants, and cafés of Park Avenue, 40 Palmer represents a rare convergence of architectural significance, uncompromising craftsmanship, and premier Winter Park location. Built by Vimaro Homes, this extraordinary new construction estate is a statement piece that redefines what luxury living looks like in the heart of Winter Park. The exterior architecture is refined yet commanding, with classical influences interpreted through a modern lens, setting the tone for the exceptional level of design and finishes found inside. One of the most remarkable features, and an offering rarely found in Winter Park, is the underground four-car garage. Designed to discreetly accommodate an impressive vehicle collection, the garage is complemented by a striking spiral staircase that rises from the basement through the main living level and continues to the second floor. The family room is nothing short of breathtaking, featuring bespoke millwork with integrated shelving, soft architectural lighting, and a dramatic fireplace wrapped entirely in marble. The kitchen is a culinary showpiece designed for those who expect nothing less than perfection. Calcutta marble countertops cascade across the space, paired with stunning custom cabinetry, and a professional-grade Thermador appliance suite. A dedicated dirty kitchen allows for discreet preparation, while an expansive walk-in pantry ensures effortless hosting and immaculate presentation. The primary bedroom wing features a spa-inspired bathroom finished in rich marble, featuring dual vanities, a freestanding soaking tub and an enormous walk-in closet with a separate washer and dryer. Upstairs, a dedicated laundry room and a spacious secondary living area provide flexibility for family living, guests, or relaxation. The lower level extends the home’s versatility, offering a workshop, dedicated holiday and seasonal storage, and seamless elevator access to the main level of the home. Outdoor living is equally impressive. A large covered exterior lanai with a pool bath and full summer kitchen creates a seamless indoor-outdoor lifestyle, ideal for entertaining year-round. The backyard is truly resort-inspired, featuring a large swimming pool, sunken fire pit, and spa, all set within a private, beautifully secluded outdoor setting. What ultimately sets 40 Palmer apart is not just its design or finishes, but its unmatched combination of luxury and location. Just minutes from Park Ave shopping and restaurants, moments from the famous Winter Park Golf Course, yet privately tucked away, this home offers a lifestyle that is both vibrant and exclusive. A truly rare opportunity to own a part of the exceptional standard of living delivered by Vimaro Homes.

$6,950,000 Active

40 Palmer Avenue Winter Park, Florida

5 Beds 6 Baths 5,905 SqFt 0.3 Acres

Rarely does a property of this caliber grace the Winter Park market. Nestled along the coveted Venetian Canal with 95 feet of pristine waterfrontage, this magnificent masonry estate is the pinnacle of refined Florida living — offering 6,396 square feet of meticulously crafted space, a private boathouse, resort-style grounds, and an address mere steps from the best of Park Avenue.From the moment you arrive, the circular driveway, porte-cochère, and motor court signal that something extraordinary awaits. Solid brick construction and lush, manicured landscaping frame a grand entrance that sets the tone for every detail within.Step through the dramatic grand foyer into a home defined by elevated ceilings, rich hardwood floors, and exquisite crown moldings throughout. The formal living and dining rooms offer elegant spaces for entertaining, while a beautifully appointed wine room with stunning glass doors adds an unmistakable touch of sophistication. A chef's kitchen that truly inspires — outfitted with professional WOLF, Sub-Zero, and Miele appliances, dual islands with breathtaking countertops, a prep sink, built-in nugget ice machine, and a butler's hallway with floor-to-ceiling storage — flows effortlessly into the warm and inviting family room (complete with fireplace) and informal dining area. Bright, sun-drenched interiors and French doors open to a spectacular covered outdoor kitchen and a beautifully landscaped turf backyard, where a stunning saltwater pool and spa invite you to unwind in style.The first-floor primary suite is a sanctuary unto itself — featuring a private office, den, or sitting room anchored by a stunning double-sided fireplace, and a spa-caliber en suite with double vanities, jetted soaking tub, walk-in shower, and an oversized custom-built walk-in closet. A true retreat from the world.Upstairs, four generously sized bedrooms offer comfort and privacy for family and guests alike. One bedroom enjoys its own private en suite and a delightful secret bonus room — a magical hideaway perfect for children. Two bedrooms share a beautifully appointed Jack-and-Jill bath, each with its own private vanity area, and the fourth bedroom is spacious and well-served by the hall bath. The pièce de résistance of the upper level is a state-of-the-art home theater, complete with projector and screen, ceiling surround sound speakers, and a built-in dry bar with wine fridge — the ultimate in at-home entertainment.A detached guest casita with a full bath and wet bar provides ideal accommodations for visitors, while a detached three-car garage offers ample space for vehicles and storage. Two laundry rooms — one per floor — add everyday convenience, and custom storage solutions are found throughout. The whole-house Lutron lighting system and full-house generator ensure comfort, security, and seamless living at every turn.And then there is the water. The private boathouse along the Venetian Canal, with 95 feet of serene waterfront, offers a lifestyle that simply cannot be replicated — direct access to Winter Park's legendary chain of lakes, all from your own backyard.Located just a short stroll to the boutiques and dining of Park Avenue, the beauty of Kraft Azalea Gardens, and the Winter Park Racquet Club, this estate offers not just a home — but a way of life that the most discerning buyers have only dreamed of.

$6,900,000 Active

1260 Alabama Drive Winter Park, Florida

6 Beds 7 Baths 6,396 SqFt 0.57 Acres

Exquisite new construction with 5 Bedrooms 6.5 Baths and a 3 car garage, in the Heart of Winter Park perfectly positioned on an oversized lot just steps from Park Avenue’s renowned shops, fine dining, and the iconic Winter Park 9-hole golf course, this extraordinary custom residence is a showcase of timeless design and modern luxury. Conceived by acclaimed architect Dan Delong of Origins Residential Design and brought to life by Sean Wulff of Native Homes, every detail has been thoughtfully curated to impress even the most discerning buyer. The expansive floor plan encompasses 5 bedrooms, 6 full baths, and 1 half bath, blending sophistication and comfort across multiple living spaces. Highlights include a dramatic great room, inviting family room, private study, downstairs guest suite, a full bar featuring a 56-bottle wine refrigerator, and an upstairs game room ideal for both everyday living and elegant entertaining. A grand entry reveals the great room with soaring floor-to-ceiling windows and elegant Italian porcelain tile, all overlooking the serene pool and patio. The chef’s kitchen seamlessly connects to the family room and features Canadian-crafted European-style cabinetry, Wolf, Sub-Zero & Fisher & Paykel appliances (dual ovens, dual dishwashers, built-in coffee maker, wine cooler, and beverage center), quartzite countertops, a large island with bar seating, hidden walk-in pantry, plus whole house water softener and filtration systems for premium convenience. The first-floor primary suite is a true retreat with spa-inspired amenities and a custom-built walk-in closet complete with cabinetry and a spacious island. Also on the main level: a private guest suite and dedicated home office/study. Upstairs, a generous game room and three additional en suite bedrooms provide comfort and privacy for family and guests alike. Designed for seamless indoor-outdoor living, the residence boasts two covered lanais finished in Turkish Marble, disappearing screens, a summer kitchen with Urban Bonfire Cabinetry, refrigerator, and ice maker, along with a freestanding fire pit and lush tropical landscaping. The saltwater pool with sun shelf and heated gas spa ensures year-round enjoyment. Built to the highest standards, the home features R-14 block walls with core 500 insulation, open cell foam insulation in attic, Andersen windows, a flat concrete tile roof, and tongue-and-groove ceilings on all lanais. Additional luxuries include:Select European white oak wood floors and Italian porcelain flooring throughout12’ ceilings on the main level, 10’ ceilings upstairsCutting-edge construction for efficiency and durability

$6,495,000 Active

550 Palmer Avenue Winter Park, Florida

5 Beds 7 Baths 5,939 SqFt 0.48 Acres

Experience timeless elegance and deliberate craftsmanship in the heart of prestigious Winter Park. This one-of-a-kind exceptional estate offers more than 7,300 square feet across three beautifully designed levels, blendingrefined luxury with modern comfort.Rich architectural details include solid red oak flooring with a walnut finish, nearly 10-foot ceilings, stackedcrown moldings, custom ironwork, designer lighting, and extensive millwork throughout. The gourmet kitchen isthoughtfully appointed with Viking and GE Monogram appliances, custom Busby cabinetry, an oversized island,and a butler’s pantry. It also includes multiple filtered water and ice zones designed for effortless entertaining.The spacious primary suite offers a true retreat with spa-inspired marble finishes, an oversized walk-in shower, ajetted soaking tub, and exceptional custom closet space.Additional features include a private elevator, Control4 automation, integrated audio/video/security systems,five HVAC systems, a central vacuum system, and a Generac whole-home generator.A fully finished and expansive basement level serves as a unique and exceptional extension of the home’s livingand entertaining space. Designed for both relaxation and recreation, it features a game and arcade room, a fullbeverage center with a dishwasher, microwave, and Scotsman ice machine, a fitness area with a sauna andsteam room, an additional laundry room, a creative storage center, and a private 4K theater with seating formultiple guests.Outdoors, resort-style living awaits with a saltwater pool and spa, a summer kitchen with a custom copper hood,an electric gated entry, landscape lighting, lush cascading bougainvillea, and ten mature magnolia trees creatingexceptional beauty and privacy. The property also features a dog run with artificial turf.Three ventless gas fireplaces, including one on the private covered porch, add warmth and ambiancethroughout the home. This home also features a whole-house water softener system.Top-rated A+ public schools are within a short walk or bike ride. Nearby highly regarded private schools includePark Maitland School, The Christ School, The First Academy, Trinity Preparatory School, Lake HighlandPreparatory School, and Bishop Moore Catholic High School.Perfectly positioned within walking distance of the boutiques and dining of Park Avenue, and just minutes fromthe Winter Park Golf Course, Rollins College, and Advent Health Winter Park, this is a rare opportunity to own anexceptional custom estate in one of Central Florida’s most sought-after communities.

$6,000,000 Active

1571 Woodland Avenue Winter Park, Florida

5 Beds 8 Baths 7,397 SqFt 0.38 Acres

Along one of the cobblestone brick streets in the prestigious Via’s of Winter Park, this completely renovated residence pairs timeless European influence with clean architectural lines and bespoke finishes throughout. A circular driveway and manicured grounds designed by Signature Landscapes create a graceful approach. Inside, a dramatic curved staircase crowned by a breathtaking 1960s vintage Venini chandelier immediately sets the tone for the exceptional craftsmanship carried throughout the home. The main gathering room is striking and inviting, defined by vaulted ceilings, a Sequoia leathered stone fireplace hearth, and a wall of glass sliders that open seamlessly to the covered lanai and heated saltwater pool. The connection between indoors and out is effortless, designed for year-round entertaining and relaxed daily living, enhanced by a full outdoor audio system. A light-filled breakfast room sits just off the kitchen, offering an intimate everyday dining space. At the heart of the home, the custom kitchen is a showpiece. Naica leathered stone countertops and a waterfall island are complemented by custom cabinetry extending to the ceiling, a professional-grade appliance suite featuring Sub-Zero and Wolf, and convenience of two Miele dishwashers. Directly adjacent, the pantry mirrors the kitchen’s cabinetry and craftsmanship and features a built-in coffee station, seamlessly connecting to the laundry area and three-car side-entry garage. A beautifully appointed guest powder room with an integrated sink is thoughtfully positioned nearby. A separate lounge showcases a custom wet bar highlighted by dramatic stonework and an integrated sink, an elegant setting for conversation and evening gatherings. A dedicated office positioned just outside the primary suite features a wall of floor-to-ceiling shelving, cabinetry and file drawers. The primary suite serves as a private sanctuary, enhanced by vaulted ceilings, backyard views and a stately two-sided stone fireplace shared with the office. Two custom walk-in closets provide exceptional storage, while the spa-inspired bath showcases Taj Mahal leathered stone countertops with integrated dual sinks, a soaking tub and an oversized glass shower with dual showerheads. Upstairs, four additional bedrooms with custom closets are complemented by beautifully finished baths and a loft sitting area with hallway built-ins. Two of the bedrooms and a bath may be closed off to create a private suite, ideal for guests or multigenerational living. A secondary staircase leads to an impressive media room equipped with a 98-inch television, state-of-the-art 7.1 surround sound and extensive storage. Outdoor living is equally elevated, featuring a weathered marble pool deck, dedicated pool bath, newly installed summer kitchen with Coyote gas grill, hood vent, sink, and leathered stone counters and backsplash, plus an outdoor living room anchored by a two-sided fireplace and television. Modern systems include a Lutron lighting system on the main level, water filtration & softener, ADT alarm - security cameras throughout and a whole-home natural gas generator. Every element of this residence has been newly installed and custom-designed, resulting in a home that blends sophisticated design, advanced functionality, and exceptional spaces for intimate living and grand entertaining. From custom millwork to curated stone selections, this home reflects uncompromising quality and thoughtful design.

$5,995,000 Active

1200 Via Salerno Winter Park, Florida

5 Beds 6 Baths 5,476 SqFt 0.45 Acres

Pre-Construction. To be built. This extraordinary lakefront residence on beautiful Lake Sylvan, set on a .37-acre (16,603± square foot) homesite, presents a rare opportunity to own a thoughtfully curated custom home by renowned builder Floridian Custom Homes, brought to life in collaboration with Winter Park Design, Brianna Michelle Interior Design and Signature Landscape. Offering 4,775 heated square feet of expertly crafted living space, this four-bedroom plus office, four-and-one-half-bath home blends timeless architecture, elevated finishes and effortless lakefront living. Designed with an open-concept floor plan ideal for everyday living and entertaining, the home showcases stunning European white oak hardwood flooring throughout all main living areas and bedrooms. The heart of the home is the spectacular chef’s kitchen, featuring two oversized islands, custom-designed wood cabinetry, an expansive walk-in pantry, and a premium Sub-Zero and Wolf appliance package highlighted by a 48-inch, eight-burner range. The private first-floor primary suite serves as a luxurious retreat, complete with an expansive walk-in closet and a spa-inspired bath adorned with marble tile shower walls and flooring. Also on the main level is a versatile office/den with a built-in closet. Upstairs, an expansive media/family room provides additional gathering space, accompanied by a dedicated office and three generously sized secondary bedrooms, each featuring en-suite baths and walk-in closets. The fourth bedroom offers exceptional flexibility and may easily serve as a secondary primary suite, ideal for guests or multigenerational living. Designed to embrace seamless indoor-outdoor living, expansive glass sliders extend from the gathering and dining rooms to a covered lanai overlooking the resort-style custom pool. Retractable screens create a setting for year-round enjoyment, while the fully equipped summer kitchen and generous lounge and dining areas make entertaining effortless. Expertly designed by Signature Landscape, the pool features a sun shelf, LED lighting and elegant travertine limestone decking, all surrounded by lush professional landscaping, Zoysia grass and privacy hedging for a serene outdoor setting. Additional notable features include a Brava slate tile roof and a striking custom glass front entry door, further elevating the home’s exceptional curb appeal. Ideally just minutes from the vibrant shops and dining of Park Avenue, this remarkable residence also offers convenient access to major roadways, leading area hospitals and top private schools, all within an A-rated school district. An exceptional opportunity to enjoy luxury lakefront living in one of Central Florida’s desirable settings.

$5,500,000 Active

313 Sylvan Drive Winter Park, Florida

4 Beds 5 Baths 4,775 SqFt 0.37 Acres

Under contract-accepting backup offers. New Hamptons-style residence offering a seamless blend of elegance and modern sophistication. A gated entrance opening to a circular driveway and motor court, set the stage for enjoying this exceptional estate. As you enter home, an impressive 2-story foyer with a glass-paneled staircase wraps around a temperature-controlled wine room and a transparent glass elevator, effortlessly connecting all levels including an expansive third-floor multi-purpose space. Designed for contemporary living, the thoughtfully curated floor plan features a spacious open concept kitchen/gathering room along with the dining area enjoy a wall of glass doors and picture window overlooking an expansive lanai, and serene backyard with a sparkling pool and spa. The main residence offers 4 bedrooms, private home office, and multiple flex spaces, complemented by a detached pool cabana that serves as a 5th guest retreat or versatile use building. The gourmet kitchen is an entertainer’s dream, featuring dual 10-foot stone islands, a 60-inch Wolf range, dual 36-inch Sub-Zero refrigerator and freezer columns, a warming drawer, beverage center and a 146-bottle Sub-Zero dual-zone wine cooler. A separate pantry kitchen is equipped with a Dacor induction cooktop, convection oven, additional refrigerator, microwave, dishwasher and ample cabinetry, ideal for catering and meal preparation. The 1st-level primary suite is a tranquil retreat, offering a sitting area, an all-marble bath with a glass-enclosed shower, multiple body sprays, a soaking tub, and French doors leading to a secluded Zen garden with an outdoor shower and fountain. There is also a hidden private home office near the front of home. The second level hosts 3 additional en-suite bedrooms, a generous lounge area, bar, and a well-appointed laundry room with extra storage cabinetry. As noted previously, there is also a unique 3rd level accessible by a staircase or elevator, that offers nearly 770 square feet of multi-use space. The outdoor living is elevated with a spacious lanai featuring motorized screens, a gas fireplace, dining space, and a summer kitchen with a 54-inch Coyote wood and gas grill, plus a separate burner beneath a remote-controlled louvered roof. There is also a detached cabana perfectly suited for a guest suite, fitness studio, additional office or game room, complete with a full bath, mini kitchen, and washer/dryer. Crafted with meticulous attention to detail, this home showcases Anderson windows, 10-foot solid doors, high-end lighting, plumbing and electrical fixtures, custom cabinetry built-ins, as well as Trane HVAC systems, ensuring quality and comfort... Lush landscaping, including magnolia trees, bamboo and cypress, surrounds the property, creating a private sanctuary. An attached side-entry garage features a powered car lift providing space for up to three vehicles. Ideally near Interlachen Country Club, Winter Park Racquet Club, Phelps Park/YMCA, and renowned Park Avenue. Note: Partial staging by RH and the furniture package can be purchased separately...

$4,950,000 Pending

1660 Palmer Avenue Winter Park, Florida

5 Beds 7 Baths 6,406 SqFt 0.36 Acres

Residing among the treelined streets of Winter Park, this stunning, contemporary pool home, designed and built by renowned Phil Kean, truly captures the essence of luxury living. Showcasing his signature aesthetic, the home emphasizes sleek architectural lines, refined finishes, and a seamless connection between indoor and outdoor spaces. Expansive walls of glass flood the interior with natural light and create a striking façade that embodies its contemporary elegance. The main living areas are designed for both entertaining and everyday living. A dramatic two-story living room is anchored by designer furnishings, which extend throughout the home, while the spacious dining area comfortably accommodates large gatherings. The adjacent family room continues the modern aesthetic with a built-in media wall, sleek fireplace, textured design elements, and a triple sliding door connecting the indoor and outdoor spaces. Ready for any caliber of chef, the kitchen boasts Thermador appliances, along with extensive cabinetry and countertop space, soft-close drawers, a waterfall edge island, generously sized pantry, and reverse osmosis water filtration. A private home theater on the main level offers a true cinematic experience with surround sound, custom seating, and blackout shades, along with a stylish wet bar, providing additional space for entertaining. The home’s Crestron automation system is discreetly integrated, allowing full control of lighting, climate, and technology from a single interface. Upstairs, a striking floating staircase leads to a gallery-style landing overlooking the living space below. For those exhausting days, you can instead take a ride on the elevator. The expansive primary suite features a sitting area, a custom closet, and terrace access. The spa-inspired primary bath includes dual rain showers with body sprays, a soaking tub, and dual vanities with elegant finishes. Additional second-floor amenities include a fitness room with steam shower and sauna, an additional en-suite bedroom, one of the two laundry rooms, and access to an upper-level terrace overlooking the landscaped grounds and pool. Two en-suite guest bedrooms are conveniently tucked away on the first floor for maximum privacy. Offering four bedrooms, five full bathrooms, and two half baths, the home delivers both comfort and sophistication at every turn. Thoughtfully integrated automated shades provide effortless privacy, while the advanced air purification systems and whole-home water softener complement the home's advanced smart features. This residence is offered fully furnished with curated Restoration Hardware pieces, including custom-selected furniture, lighting, rugs, and artwork that enhance its cohesive design. Outdoor living is equally impressive, with covered lanai spaces enhanced by automated roll-down screens, designer furnishings, a summer kitchen with gas grill and ventilation, and tranquil poolside views. The property also includes a split, three-car garage with a large driveway protected by a gated entrance. Completing this extraordinary dwelling is its location in the heart of Winter Park. This lakeside residence sits minutes from Park Ave Shopping, Rollins College, AdventHealth, multiple Botanical Gardens and Museums, well-rated grade schools, and highway access. Schedule your private showing today and experience the Winter Park lifestyle firsthand.

$4,950,000 Active

231 Chelton Circle Winter Park, Florida

4 Beds 7 Baths 5,550 SqFt 0.6 Acres

Beautifully built in 2022 by Lonnie Richardson, this custom one-story home sits on a quiet cul-de-sac in the heart of Winter Park. Designed with a modern, timeless style, it offers luxury finishes paired with a warm, comfortable feel.The home features 4,060 square feet, including four en-suite bedrooms, five full bathrooms, a powder bath, and a bonus room with a built-in office. The spacious gourmet kitchen overlooks the main living areas and pool, and is equipped with premium Wolf appliances and a separate chef’s kitchen for added convenience.Enjoy seamless indoor-outdoor living with a covered lanai featuring motorized screens, heaters, and a mosquito misting system. The outdoor space also includes a summer kitchen, gas fire pit, and a pool equipped with a swim jet system that creates a continuous current, effectively transforming it into an endless lap pool.A detached fitness studio with a steam shower provides a private wellness retreat. Additional highlights include custom built-ins, engineered hardwood floors and surround sound throughout.The oversized two-car garage offers epoxy flooring, custom storage, and a dog wash station. Irrigation is supplied by a private well, and the home also features underground utilities and a full security system.The exterior is designed for both beauty and low maintenance, with manicured landscaping and artificial turf that stays lush year-round. With no HOA, added privacy, and exceptional attention to detail throughout, this home offers a rare opportunity to experience luxury living at its finest.This home is conveniently located near the Enzian Theater and less than a mile from Winter Park Village, with top-rated schools nearby, this home combines comfort, style and an unbeatable location.Schedule your private showing today.

$4,285,000 Active

1441 Cardinal Court Winter Park, Florida

4 Beds 6 Baths 4,066 SqFt 0.36 Acres

Under contract-accepting backup offers. Introducing one of Winter Park's most extraordinary offerings — a meticulously designed transitional masterpiece by the acclaimed Winter Park Custom Homes, set on a rare 0.34-acre corner lot in one of the city's most coveted neighborhoods. From the moment you arrive at the circular front drive and step onto the marble-tiled covered front porch, it's clear this home is in a class of its own. Inside, soaring beamed ceilings and wide-plank engineered wood floors set an elevated tone throughout. The grand living room features a gas fireplace and dramatic accordion glass doors that dissolve the boundary between indoors and out, opening to the resort-style backyard with ease. The chef's kitchen is a true work of art: anchored by a massive island with wraparound seating, Thermador gas range and oven, built-in refrigerator and microwave, marble countertops, and a generous walk-in pantry — all complemented by stunning herringbone hardwood floors that make this space feel straight out of the pages of a design magazine. A butler's hallway and charming brick-floored cozy reading room add warmth and character to the everyday. Also on the main level, a full en-suite office — easily serving as a 6th bedroom — offers flexible living for guests or multi-generational needs, while a separate powder room is thoughtfully reserved for guest use. The primary suite is a sanctuary unto itself: a private vestibule entry leads to a spacious bedroom retreat with accordion-style doors that open directly to stepping stones leading into your personal spa. The spa-inspired primary bath showcases marble countertops and inlay floors, separate sink vanities, a freestanding soaking tub, a walk-in shower, and a custom-built walk-in closet that rivals any boutique. Upstairs, four generously sized en-suite bedrooms — each with walk-in closets — surround a spectacular bonus room complete with a wet bar, perfect for entertaining or movie nights. The third floor is a true Winter Park rarity — an expansive additional living level with a dedicated gym area and playroom ideal for home theater, creative pursuits, or whatever your lifestyle demands. Built-in speakers complete the experience. Step outside to your own private resort. A heated pool and spa with a sun shelf, fire bowl, and serene stepping stones are framed by lush artificial turf and elegant marble-inlaid pavers. The covered back patio with tongue-and-groove ceiling and fireplace creates an al fresco living room, while the outdoor grill with prep sink makes entertaining effortless. Natural gas throughout, a full-house generator, sauna, and an epoxy-floored two-car side garage round out this exceptional property — all seamlessly controlled through a whole-home Control4 automation system that puts lighting, climate, audio, security, and more at your fingertips. Zoned for A-rated Winter Park schools and just minutes from Park Maitland School (K–6), Park Avenue's world-class dining and boutiques, and all that Central Florida has to offer. Homes of this caliber, at this scale, in this location simply do not come available often. This is not just a home — it's a lifestyle.

$4,250,000 Pending

650 Dixie Parkway Winter Park, Florida

6 Beds 7 Baths 6,007 SqFt 0.34 Acres

Under contract-accepting backup offers. Pre-Construction. To be built. A Generational Opportunity in the Heart of Winter ParkPresenting an exceptionally rare opportunity to build a fully custom luxury estate on one of Winter Park’s most extraordinary homesites. Situated on an expansive 1/2-acre corner lot, an offering virtually unheard of in this coveted location, this property represents the pinnacle of luxury new construction potential.Scheduled for Summer 2027 completion, this bespoke residence offers the flexibility to bring the current architectural concept to life, collaborate with the builder to tailor the design, or create an entirely custom vision with your own architect and design team.The proposed architectural concept showcases an impressive modern estate designed for elevated living and grand-scale entertaining, featuring a dramatic double-height foyer, soaring two-story great room, expansive walls of glass that flood the interiors with natural light, a highly desirable 4-car garage, oversized bedroom suites, and thoughtfully curated indoor-outdoor living spaces throughout.Designed to deliver a true resort-style experience, the outdoor living concept includes a saltwater pool and spa, covered lanai, summer kitchen, and expansive entertaining areas ideal for year-round Florida living.Further elevating this offering is deeded access to Lake Sue, providing an exclusive lifestyle opportunity rarely available in this location. Enjoy the best of both privacy and recreation while being moments from everything Winter Park is known for.Perfectly positioned just minutes from renowned Park Avenue, residents enjoy immediate access to premier fine dining, luxury boutiques, private clubs, and cultural attractions, all while being zoned for top-rated schools.Oversized parcels of this caliber with deeded lake access are exceptionally scarce, making this a true legacy acquisition, an opportunity to create a one-of-one estate in one of Central Florida’s most sought-after neighborhoods.Luxury, land, lake access, and limitless potential—this is Winter Park living at its absolute finest.

$4,200,000 Pending

141 W Lake Sue Avenue Winter Park, Florida

5 Beds 7 Baths 5,500 SqFt 0.51 Acres

In the heart of Winter Park, 1150 Via Salerno is a newly completed Mediterranean-minimalist residence that blends architectural refinement w/ organic warmth. Now offered at a newly adjusted price, the home presents a compelling opportunity to experience design-forward new construction in the Vias neighborhood. Developed and designed by Steve & Jodie Warrick Konold of Scout & Co., the 3,850-sf layout offers 4 bedrooms & 5.5 baths, wrapped in the intentional privacy of a luxury retreat. Beyond its terraced walkway & garden courtyard—envisioned in collaboration w/ architect Cynde Norris—French antique gates open to a native-planted entry garden, creating a soft transition to the interior. A glass foyer introduces a tongue-and-groove ceiling & woven rattan chandelier, sourced & designed in London, leading to a sculptural stairwell positioned just off the main living spaces. The great room features soaring ceilings, a sleek fireplace & walls of glass windows & doors that blur the boundary between inside & out. Ten-inch baseboards meet level 5 drywall in a clean reveal, paired w/ micro-crete flooring on the main level & wide-plank European oak upstairs. In the kitchen, materials w/ function are elevated w/ a Thermadore dual-fuel range, custom plaster hood, full refrigerator & freezer columns & a large island topped in honed black quartzite. The surrounding cabinetry is crafted from hand-carved V-groove panels w/ soft-close hardware & integrated pullout storage. Caesarstone surfaces run along the perimeter while steel-and-glass open shelving w/ a sculptural black sconce balance the composition. A vintage chandelier from Prize Home & Garden sourced in Round Top completes the room. The primary suite occupies a private wing on the main floor accessed via antique gallery doors that lead to the rear courtyard. Vaulted ceilings, a custom walk-in closet w/ a spa-like bath provide a luxurious retreat. Features include a long double vanity, matte black Kohler fixtures, a freestanding tub, walk-in shower w/ built-in bench & separate water closet. On the mezzanine level, the powder bath makes a dramatic statement w/ a floating black quartzite trough sink w/ handwoven mirror. Across the hall, the laundry room blends beauty w/ utility w/ custom cabinetry, matching quartzite surfaces, matte black fixtures & a side-by-side front-load washer & dryer. A nearby guest suite is marked by an antique door entry. The en-suite bath features a hand-painted tile threshold & suede-framed mirror. Two upstairs bedroom suites feature en-suite baths, designer lighting, distinctive mirrors & continuous European oak flooring. Positioned at the front of the home, the rooftop terrace is accessible via the upper hallway. The detached casita opens to the pool courtyard through accordion glass doors & features micro-crete floors, a woven rattan chandelier & a full bath—ideal as a studio, gym or office. Outdoor spaces include two garden courtyards, a fully fenced backyard, a heated saltwater pool & a rooftop terrace, all enclosed by masonry walls & a board-on-board privacy fence. Additional features include a lower-level two-car garage, storage closet, 3 HVAC systems, Rinnai tankless water heater, Sierra Pacific windows, customized closets, solid core interior doors, 6” round gutters & a Barcelona barrel tile roof. Thoughtfully designed & beautifully executed, 1150 Via Salerno offers a refined lifestyle tucked within one of Winter Park’s most exclusive enclaves.

$4,195,000 Active

1150 Via Salerno Winter Park, Florida

4 Beds 6 Baths 3,850 SqFt 0.21 Acres

Long before this home stood gracefully on its prominent corner, it existed as a vision in the mind of master builder Keith D. Field. Conceived as the opposite of a production home, it was crafted with a builder’s eye for structural integrity, thoughtful flow, and a seamless connection between indoors and out. Set on a generous 91-foot wide lot, this custom residence offers 5 bedrooms and a floor plan that feels both substantial and inviting. A wide front veranda sets a timeless tone from the moment you arrive. Dark-framed windows and doors create a striking contrast, while manicured hedges and brick-paved drives enhance the classic curb appeal and highlight the home’s architectural details. Step inside and you immediately sense that this is more than just a beautiful house—it’s a home with a story. At its heart is the reclaimed pine flooring, sourced from a Florida bridge. Rich with character, worn in all the right ways, these floors bring a warmth and authenticity you simply cannot replicate with something new. A long, gracious foyer introduces the main living spaces. To your left, a handsome study/office with a brick fireplace offers an intimate retreat for working. To your right, a formal dining room with garden views comfortably accommodates twelve. A discreet swing door leads to a well-appointed wet bar and large walk-in pantry, which then opens into the expansive kitchen. The kitchen is the true hub of the home, anchored by coffered ceilings, an oversized island, a full suite of high-end appliances, abundant cabinetry, and extensive counter space. A light-filled dinette offers the perfect spot for casual meals. At the center of the home, an oversized great room draws everyone together with its tall brick fireplace, built-in display/bookshelves, and high ceilings that add volume without sacrificing warmth. Two bedrooms are thoughtfully located on the main level, including the primary suite, privately positioned in one of the quietest corners of the home. Filled with soft natural light, accentuating the detailed millwork that runs from floor to ceiling. The primary bath is a retreat in itself, featuring slate flooring, double vanity, claw-foot soaking tub, water closet, walk-in shower with rain head, and a massive custom walk-in closet. The second main-level bedroom functions beautifully as a guest suite or flexible space, with an en-suite bath that also serves as a pool bath, a built-in Murphy bed with integrated cabinetry. A back facing staircase leads to two additional en-suite bedrooms on the second level. At the top of the landing, a large built-in workstation creates an ideal homework or creative zone, and both bedrooms enjoy access to a full-length front balcony. At the back of the home, a separate staircase leads to the fifth bedroom—a wonderfully private suite with dormer windows, angled ceilings with beams, and its own en-suite bath. In addition to a walk-in closet, cleverly designed built-in storage along the walls ensures a place for everything. Off the great room, a covered lanai with tongue-and-groove wood ceiling and brick built-in grilling station creates a comfortable space for year-round relaxation. A 45-foot lap pool is anchored by a striking cabana with fireplace, evoking a resort-inspired setting for long afternoons, evening gatherings, and memorable celebrations. This is a rare opportunity to own a thoughtfully crafted estate where history, craftsmanship, and everyday comfort come together in perfect balance.

$3,995,000 Active

1600 Legion Drive Winter Park, Florida

5 Beds 6 Baths 4,483 SqFt 0.32 Acres

Conveniently situated near the Winter Park Country Club, this contemporary masterpiece, built by premier builder Z Properties, offers the ideal mix of style, comfort, and modern living. Meticulously maintained with great inspection. Completed in 2021, the residence has 4,181 square feet of thoughtfully designed living space, including four bedrooms each with a private ensuite bath and an additional powder room. A 412-square-foot casita with a wet bar and private entrance completes its functionality by providing extra flexibility, perfect for guests, extended family, workspace or workout area.The interiors showcase timeless design with high ceilings, glass walls, and carefully curated finishes. The chef’s kitchen and butler’s pantry pair handcrafted cabinetry and stone surfaces with professional-grade appliances, flowing seamlessly into open living and dining spaces designed for both everyday living and entertaining.Outdoors, a 65-foot lap pool anchors the private backyard retreat, complemented by a covered lanai, marine-grade summer kitchen, fireplace lounge, tree garden and lush landscaping. Solid block construction, advanced state-of-the-art home systems, and a climate-controlled two-car garage with an extended hidden driveway highlight the home’s privacy, quality, and convenience.With a distinct European vibe under canopy trees and cobblestone streets in the desirable Valencia Terrace neighborhood, this home is just moments from Park Avenue’s boutiques, fine dining, Rollins College, the Farmers’ Market, and the Morse Museum. Zoned for top-rated Winter Park schools, it offers both luxury and practicality in one of Central Florida’s most sought-after communities.

$3,995,000 Active

1161 Valencia Avenue Winter Park, Florida

4 Beds 5 Baths 4,181 SqFt 0.32 Acres

(HUGE PRICE REDUCTION & NEWLY ENHANCED REAR LANDSCAPING ADDED FOR EXCEPTIONAL PRIVACY AND MORE SECLUDED OUTDOOR LIVING EXPERIENCE) Step into this stunning West-Indies inspired luxury home crafted by Nautilus Homes, where tropical charm meets timeless elegance. An architectural masterpiece in the City of Winter Park. This five-bedroom seven-bath home that includes a private in-law suite offers plenty of exquisite interior features. The home welcomes you with a beautifully designed 16 ft wide circular driveway wrapped in upgraded pavers, offering both elegance and functionality. A very rare 4-car garage in Winter Park with two in the rear and two in the front of the home. Starting with entering through massive 10 ft. double iron doors flowing into the foyer with 11ft high ceiling beginning with the flex/office room and formal dining to your left and right. Followed by entering the gallery that leads to the great room. The Chef’s Kitchen, a culinary dream featuring an oversized center island, quartz countertops throughout, custom 42"+15" wood cabinetry, a custom walk-in pantry, and top-of-the-line Thermador professional series. That Includes a 48' refrigerator, 48" gas cooktop, custom hood, dishwasher, built-in microwave, double convection ovens and built in coffee station. On your way to the formal dining, you pass by the show-stopping, Tempered glass wine room. Its crystal-clear glass enclosure offers a striking view of your curated collection, while the built-in wine chiller ensures each bottle is perfectly preserved. This elegant transition creates a seamless blend of function and sophistication, setting the tone for unforgettable dining experiences just steps away. The primary suite offers tranquility peace of mind, and the primary bath has a spa-like oasis with a spacious shower stand-alone tub. Followed by a custom closet thoughtfully design with plenty of room and storage. The guest retreat area has a huge bedroom, access to a full bath including private access to the Lania and pool. Tucked away with its own private entrance attached to the rear garage, the in-law suite above the garage offers the perfect blend of comfort and independence. This thoughtfully designed space includes a full bath, a cozy living area, and a convenient space with a kitchenette—ideal for extended stays or multi-generational living. Make your way to the second floor that has 11ft ceilings as well. As you reach the top the space opens into a massive game room with a wet bar, perfect for entertainment retreat with a balcony. All second-floor bedrooms have a thoughtfully design with a full bath for privacy. As you make your way back downstairs to outside, step through the oversized sliding glass doors and into your private outdoor oasis. Effortlessly extending your living space into the open air. Just beyond, the sparkling gas heated/saltwater pool and spa framed by lush landscaping and designed for both relaxation and recreation. Also, the fully equipped summer kitchen features gas grille, beverage refrigerator and ample counter space—perfect for alfresco dining and effortless entertaining. This masterpiece is equipped with a full irrigation system around the home, exterior lighting, exterior cameras for security. Smart home system ready for lighting, music and security controlled by Control 4 system for your convenience. Interlachen Golf community less than 5 min, Phelps Park walking distance, Park Ave 10 min and restaurant and retail minutes away.

$3,875,000 Active

1782 Pine Avenue Winter Park, Florida

5 Beds 7 Baths 4,782 SqFt 0.36 Acres

JUST COMPLETED....WINTER PARK / LAKE SUE DISTRICT — A TRUE STANDOUT IN TODAY’S LUXURY NEW CONSTRUCTION MARKETProudly presented by RARE Builders, a name synonymous with design-forward custom homes that continue to help set and raise the standard in Orlando and Winter Park, this newly completed residence represents a rare opportunity to secure a fully realized custom home in one of the area’s most sought-after neighborhoods.Positioned just steps from Lake Chelton and Lake Sue, and located within a highly desirable Winter Park school district, the setting delivers an exceptional lifestyle in one of Central Florida’s most dynamic and tightly held areas.While new construction inventory exists in today’s market, this home stands apart offering a fresh, cutting-edge architectural vision brought to life through exceptional planning, material selection, and execution. Prominently sited on an elevated homesite with a striking front elevation, the home offers 4,500 square feet of living space, including nearly 3,000 square feet on the ground level alone... a rare and highly functional configuration.The layout is both expansive and intentional, featuring multiple large living spaces, a private ground-floor primary suite, and a well-appointed guest suite/study/flex space. Upstairs, each bedroom is thoughtfully designed with either an en-suite bath or direct access to a full bath, delivering both comfort and privacy throughout.The defining feature of this home...and one rarely seen in the market... is the massive Renlita Floataway door system, which opens an entire wall of the home to seamlessly connect the interior Florida room with the resort-style outdoor living environment. This creates a true four-season entertaining space, transforming the way the home lives and offering a level of indoor-outdoor integration that is both dramatic and highly functional.The outdoor setting is designed as a private resort, complete with a pool, spa, fire and water features, pergola, and summer kitchen... all curated to complement the home’s architectural vision.Inside, the level of finish and design is exceptional. From breathtaking Venetian plaster walls to a dramatic two-story foyer, the home is defined by a refined and highly curated selection of materials, fixtures, and hardware. Every element has been intentionally sourced and executed, resulting in a level of craftsmanship and aesthetic cohesion that is rarely achieved and immediately recognized by discerning buyers.A well-appointed kitchen with walk-in butler’s pantry and thoughtfully designed secondary spaces further enhance both function and livability. Integrated Control4 home automation, audio, and security systems complete the offering.Located just minutes from Downtown Orlando, Winter Park, Park Avenue, Winter Park Village, AdventHealth, and Orlando Health, this home delivers a rare combination of location, design, and execution at the highest level.This is not simply new construction, it is a distinct, design-driven custom residence offering a level of detail, presence, and livability that is truly rare in the current Winter Park market.

$3,799,000 Pending

150 Dana Way Winter Park, Florida

5 Beds 5 Baths 4,451 SqFt 0.27 Acres

Under Construction. Step into a world where the timeless charm of Old Winter Park meets the pinnacle of modern luxury designed by Winter Park Design and masterfully crafted by renowned builder Vimaro Homes. Nestled on one of Winter Park’s most coveted tree-lined streets, this stately home immediately commands attention with its double-entry driveway, framed by manicured landscaping and a sense of grandeur like no other. Inside, the home unfolds across more than 3,600 square feet of impeccably designed living space, with every room telling a story of quality, craftsmanship, and comfort. Rich herringbone hardwood floors stretch throughout the residence, complemented by bespoke millwork, and soaring ceilings. At the core of the home, the designer chef’s kitchen is a true showpiece, crafted for culinary excellence and effortless entertaining. Outfitted with top-of-the-line stainless steel appliances, custom cabinetry with designer hardware, and striking quartz countertops, the space is as functional as it is beautiful. A large island provides a natural gathering place, while an adjacent walk-in pantry offers seamless storage and prep. The primary suite is a retreat unto itself; a serene oasis tucked away for ultimate privacy. The spa-inspired en-suite bathroom rivals the finest resorts, featuring a soaking tub, walk-in shower with rainfall fixtures, designer lighting, dual vanities with custom cabinetry, and luxurious stone finishes throughout. A large, custom walk-in closet completes this elegant retreat. Beyond the main living areas, this home offers unique and thoughtfully designed spaces that elevate everyday living including a dedicated home office, a spacious loft, and a grand 3rd floor bonus room. Outdoors, a resort-style pool, covered lanai, and fully equipped summer kitchen create a private haven for year-round entertaining under the Florida sun. For the car enthusiast, this home offers a perfect fusion of elegance and functionality with a stately porte-cochere, a detached garage connected to the home by a breezeway, and an expansive motor court ideal for guest parking or showcasing a prized collection. Every element of this home speaks to impeccable taste and thoughtful design, from the curated finishes and luxury fixtures to the breathtaking architecture and designer lighting. Located just moments from Park Avenue, Rollins College, and Winter Park’s finest shopping and dining, you are truly in the heart of it all. More than a residence, this is a rare architectural masterpiece by Vimaro offering an unmatched lifestyle in the heart of one of Central Florida’s most coveted neighborhoods.

$3,650,000 Active

207 E Kings Way Winter Park, Florida

5 Beds 5 Baths 3,719 SqFt 0.23 Acres

Park Hill is one of Winter Park's most coveted addresses, a distinguished collection of luxury brownstones situated at the northern end of Park Avenue, moments from the city's finest boutiques, restaurants, cultural landmarks and the historic Winter Park Golf Course. Within this exclusive enclave, residence 649 occupies one of the community's most private settings. Beyond the stately brick courtyard and gas lantern-adorned entrance, this three-story home with a private elevator is thoughtfully scaled for refined living. Not oversized, but extraordinarily well-appointed. Ten-foot ceilings, intricate millwork and moldings and generous windows establish an ambiance of quiet elegance, while hardwood floors and designer fixtures carry that standard throughout. The open-concept main living area is built for effortless entertaining. The chef's kitchen features Wolf and Sub-Zero appliances, custom wood cabinetry, marble accents, a center island with bar seating and a wet bar with a beverage refrigerator and ice maker. The space opens directly to a private courtyard with a summer kitchen and dedicated alfresco dining area, creating a genuinely tranquil retreat that feels removed from the energy of the avenue. Upstairs, two guest suites each offer walk-in closets and en-suite baths. A dedicated laundry room and a covered terrace with a fireplace, wet bar and half bath complete the level. The third-floor primary suite provides a true sense of retreat, with two custom walk-in closets, a private balcony and a spa bath filled with natural light from windows and skylights. Dual vanities, a glass-enclosed steam shower and a soaking tub are finished throughout in premium materials. Constructed of Old Carolina brick with three-story block construction, precast exterior trim and a slate mansard roof, the residence features a two-car air-conditioned garage, ample storage and soundproof hollow core floors. With exterior maintenance managed by the association, the lifestyle here is genuinely lock-and-leave. This is a rare opportunity to own in one of Central Florida's most prestigious communities, in a location that simply cannot be replicated.

$3,500,000 Active

649 N Park Avenue Winter Park, Florida

3 Beds 5 Baths 3,180 SqFt 0.09 Acres

Experience resort-style living at 1836 Whitehall Drive! Inspired by the warm breeze and seaside elegance of a tranquil island paradise, this new custom home by Urban Perch, A Boutique Home Builder, offers a timeless front elevation, exquisite finishes inside and out, and unobstructed views of the beautiful outdoors from almost every room. Totaling 4,168 square feet, this five-bedroom, five-bath residence (and casita!) features a unique U-shaped floor plan ensuring natural light shines through every gathering space. Channeling the natural sands of a sunny retreat, the kitchen features white marble countertops and backsplash with blush pink undertones. A custom plaster hood, La Cornue gas range, a wall of cabinets with paneled GE Monogram appliances and a scullery with additional prep space create a kitchen ideal for entertaining. The marble island overlooks one of the main living rooms, where white oak trim highlights the precast stone surrounding the gas fireplace. A vaulted ceiling with natural wooden beams accentuates the bubble chandelier and level 5 drywall finish. Full-height sliding glass doors invite you to soak in the saltwater pool, summer kitchen, landscaped grounds and detached casita beyond. With accordion-style doors and a side entrance, the casita can serve as a pool house, personal home gym or additional bedroom with full bath. Sightlines from the main entrance lead you to the outdoors but also serve as observation points for the color-drenched first floor bedroom and primary suite with arched entry. A freestanding tub with smart glass window, zero-entry shower and extra thick Taj Mahal quartzite countertops elevate the primary bath to pure relaxation. Outside the primary suite, a concealed under-stairs laundry closet appears elegant, as impeccable millwork provides seamless transitions to the adjacent accent wall. Completing the first floor is a formal living room and dining room, a bold powder room, and a charming mudroom with custom cabinets. Follow the wrought-iron railing and engineered wood flooring to the expansive second floor. A flex room, three additional bedrooms and baths, a large laundry room, and built-in closets and benches keep everything organized and beautiful. This exceptional Winter Park home, crafted with intention and experience from award-winning local custom home builder, Urban Perch, elevates everyday living to approachable luxury.

$3,500,000 Active

1836 Whitehall Drive Winter Park, Florida

5 Beds 7 Baths 4,168 SqFt 0.25 Acres

Positioned on a quiet canal, this exceptional property features a covered boat dock with lift, offering effortless access to the renowned Winter Park Chain of Lakes. This home, built by Liberty Development, with 4-bedrooms plus two bonus rooms blends elegance with comfortable everyday living. The main level offers a dedicated office area, formal dining room, and an inviting gathering room with gas fireplace, all flowing seamlessly into the stunning chef’s kitchen. Designed for entertaining, the kitchen features two large islands, exotic granite countertops, under-cabinet lighting, and premium Thermador appliances including a 6-burner gas range with griddle. The walk-in butler’s pantry has a beverage cooler and ice maker adds both style and functionality. The adjoining breakfast area is framed by grand windows overlooking the pool, cabana, and canal. The luxurious downstairs primary suite enjoys tranquil water views and a spa-inspired bath with travertine stone floors, marble counters, custom cabinetry, soaking tub, walk-in shower with steam and generous closet space. Upstairs you’ll find three additional bedrooms and a spacious bonus room, while a separate bonus suite above the garage provides future space for a media room, gym or guest retreat. The interior of the home is highlighted by hardwood floors, plantation shutters, decorative moldings and designer lighting throughout. The outdoor living area is equally impressive. French doors open to a covered porch with classic Old Winter Park brick, leading to a travertine-surrounded pool and private cabana with a wood-burning fireplace. Exterior highlights include a metal roof, durable cement board siding and wooden shutters. Don’t miss this limited opportunity to have immediate and easy access to the coveted Winter Park Chain of Lakes. *Some photos have been virtually staged*

$3,500,000 Active

2240 Venetian Way Winter Park, Florida

4 Beds 4 Baths 4,036 SqFt 0.31 Acres

Under Construction. New construction by LUIH Homes, ideally on a charming brick street in one of Winter Park’s desirable locations. Thoughtfully designed with over-the-top quality, exceptional functionality and timeless style, this five-bedroom, five-and-one-half-bath residence offers an outstanding floor plan for everyday living and entertaining. Elegant double entry doors open to a welcoming foyer and a light-filled interior featuring beautiful wood flooring throughout the main living areas and all bedrooms on both levels. The open-concept design seamlessly connects the spacious living room, dining area and chef’s kitchen, creating a warm and inviting atmosphere. Expansive windows and sliding glass doors flood the home with natural light while providing picturesque views of the covered lanai, pool and backyard. The kitchen is beautifully appointed with premium Thermador appliances, including a six-burner gas range with oven, built-in oven and microwave, and a Zephyr under-counter wine refrigerator. Custom cabinetry, generous workspace, and a large walk-in pantry make this kitchen as functional as it is stylish. The first floor also features a private guest suite complete with a walk-in closet and en-suite bath, as well as a dedicated office positioned toward the front of the home with views of the front entrance and driveway. Outdoor living is equally impressive. The expansive 40-by-14-foot covered lanai overlooks the approximately 40-by-15-foot pool and offers a fully equipped summer kitchen with abundant space for lounging, dining and entertaining year-round. Upstairs, the luxurious primary suite serves as a private retreat featuring a spa-inspired bath, oversized custom walk-in closet and access to a covered balcony. Three additional bedroom suites, each with a private bath, provide comfortable accommodations for family and guests. A spacious family/media room and secondary laundry room complete the second level. Enjoy an exceptional Winter Park lifestyle just minutes from the renowned shopping and dining destinations of Park Avenue, Hannibal Square and Winter Park Village. Zoned for sought-after Audubon K-8 and Winter Park High School, this outstanding location also offers convenient access to major hospitals, downtown Orlando, Orlando Executive Airport, Orlando International Airport and major roadways for easy commuting throughout Central Florida.

$3,490,000 Active

121 E Fawsett Road Winter Park, Florida

5 Beds 6 Baths 4,191 SqFt 0.28 Acres

This exceptional Winter Park residence offers a floor plan rarely found in the area, with nearly all living spaces thoughtfully positioned on a single level for effortless everyday living. Completely rebuilt in 2018 by renowned custom builder Posada Homes, a member of the elite Master Custom Builders Council, the home blends modern design, crisp architectural lines, and timeless elegance across an expansive 0.39-acre lot along one of Winter Park’s most picturesque tree-lined streets. The home immediately captivates with its refined architecture and beautifully manicured grounds. Inside, sunlight streams through expansive windows, illuminating hardwood flooring, intricate millwork, and thoughtfully curated finishes that reflect the craftsmanship of a true custom build. Just off the foyer, a hidden wine room provides a sophisticated surprise, perfect for those who love to entertain. At the center of the home is the chef’s kitchen designed for both beauty and functionality. Outfitted with premium Thermador appliances, sleek quartz countertops, a generous center island, and custom cabinetry, the kitchen flows effortlessly into the expansive great room where high ceilings, designer lighting, and elegant architectural details create an atmosphere that is both inviting and refined. Tucked away for privacy, the primary suite is positioned just off a luxurious family room featuring custom built-ins and a gas fireplace. The primary suite itself is a true sanctuary, complete with a sitting area, private coffee bar, and a spa-inspired bath featuring dual vanities, a soaking tub, and an oversized walk-in shower. Rarely found in Winter Park, all bedrooms are conveniently located on one level, including two primary suites, allowing the home to deliver seamless livability without sacrificing architectural interest or sophistication. Upstairs, a private office, half bath, and bonus room provide the perfect space for work, media, recreation, or relaxation. Outdoors, the home transforms into a private resort-style retreat. A covered lanai overlooks the sparkling pool and expansive grounds, creating the ideal setting for entertaining or quiet evenings at home. Adding even more flexibility, a 252-square-foot detached studio currently functions as a gym but could easily become a summer kitchen cabana, guest retreat, or art studio. Located within walking distance of Park Avenue’s boutiques, restaurants, and cafés, and just moments from Rollins College and the Winter Park Chain of Lakes, this residence embodies luxury living at its finest. Don’t miss this rare opportunity to own one of Winter Park’s most outstanding homes. The current flooring offers a rich look, and for those who prefer a lighter palette, the seller is open to providing a credit toward flooring updates and coordinating the installation of new flooring if desired.

$3,393,000 Active

1581 Forest Avenue Winter Park, Florida

4 Beds 6 Baths 4,683 SqFt 0.39 Acres

Nestled just moments from the boutiques and cafés on Park Avenue, this newly completed masterpiece redefines Winter Park luxury living. Perfectly positioned on an expansive 0.30-acre lot, this residence captures attention from the moment you arrive, with its striking architectural details, a sweeping driveway, and detached garage that together set a tone of timeless sophistication. Inside, soaring 20-foot ceilings welcome you into a grand foyer framed by curved archways and exceptional millwork. The living room is a true showpiece, centered around a statement fireplace with built-in shelving and subtle LED underlighting that accentuates every detail. The chef’s kitchen is a work of art, showcasing quartz countertops, exquisite custom cabinetry, integrated LED lighting, a Wolf appliance suite, and a charming breakfast nook. The formal dining room captivates, with stunning coffered ceilings floor to ceiling windows, and an atmosphere perfectly suited for elegant entertainment. The primary suite is a private sanctuary, offering dual vanities with floating mirrors, a freestanding soaking tub, a walk-in rain shower, and a spacious custom closet. Each additional bedroom has been thoughtfully designed with generous proportions and its own en-suite bath, blending comfort with sophistication. Upstairs, a loft and secondary laundry area provide convenience and versatility, while the main level includes a full mudroom and butler’s pantry with an additional washer and dryer, tailored for effortless living. The outdoor living space rivals the most luxurious resorts. A covered lanai with retractable screens seamlessly extends the interior’s sophistication outdoors, offering a year-round retreat for dining or lounging. The expansive pool deck unfolds around a sparkling pool and integrated spa, complemented by a dedicated pool bath connected to the detached garage. From the curved archways to the meticulous millwork and layered LED lighting throughout, every inch of this home reflects the builder’s attention to detail and commitment to craftsmanship. It is more than a home, it is a statement of style, presence, and precision in the heart of Winter Park’s most coveted location.

$3,390,000 Active

1751 Glencoe Road Winter Park, Florida

5 Beds 7 Baths 4,520 SqFt 0.3 Acres

Under contract-accepting backup offers. Set along a picturesque brick street, 2040 Randall Circle is a beautifully crafted residence that pairs timeless architecture with elevated, designer finishes and a functional floor plan. Framed by manicured landscaping and connected to a detached two-car garage by a covered walkway, the home offers classic curb appeal in an idyllic setting just minutes from vibrant shopping and dining on Park Avenue. Inside, rich hardwood floors run throughout the living spaces, complemented by Restoration Hardware lighting that brings a refined, cohesive feel to every room. The welcoming foyer opens to a gracious formal living room with a gas fireplace and custom built-ins, an elegant yet comfortable space for entertaining or relaxing. Just beyond, the formal dining room is well proportioned for hosting holiday gatherings and dinner parties with ease. The heart of the home is the expansive chef’s kitchen, thoughtfully designed for everyday living and effortless entertaining. An oversized island anchors the space, topped with Carrara marble counters and offering generous seating. A dual Wolf oven with six-burner range plus French cooktop, custom cabinetry, walk-in pantry, and a butler’s pantry complete with under-counter wine refrigerator provide beauty and functionality. A spacious breakfast room filled with natural light overlooks the backyard and flows seamlessly into the family room. Here, a gas fireplace, custom built-ins and three sets of French doors create a warm focal point while inviting in the outdoors. The first-floor primary suite serves as a private retreat, featuring large windows with tranquil views of the pool and direct access to the covered lanai. Dual walk-in closets provide ample storage, and the spa-like primary bath is finished in Carrara marble, offering a large soaking tub and an expansive glass-enclosed shower with dual shower heads. Two powder baths, one thoughtfully designed as a pool bath, along with one of two laundry rooms complete the main level. Upstairs, four additional bedrooms and a dedicated office provide generous space for family and guests. Two of the bedrooms feature private en-suite baths, while the remaining two share a well-appointed Jack & Jill bath. One of these rooms is arranged as a bonus lounge, offering flexibility to serve as a fifth bedroom, media room or additional gathering space if desired. The thoughtful second-floor layout easily adapts to a variety of lifestyle needs, whether accommodating guests, growing families or multi-generational living. A secondary laundry room upstairs adds an added layer of everyday convenience. Outdoor living is equally impressive. The spacious covered lanai with summer kitchen overlooks the saltwater, heated pool and spa, creating an extension of the interior living space. Brick paver flooring continues from the lanai to the open patio, offering multiple areas for lounging, dining and entertaining beneath the Florida sky. Ideally in a desirable location and zoned for sought-after Audubon Park K-8, 2040 Randall Circle offers timeless style, thoughtful design and seamless indoor-outdoor living in one of the area’s charming neighborhoods.

$3,350,000 Pending

2040 Randall Circle Winter Park, Florida

5 Beds 6 Baths 4,636 SqFt 0.27 Acres

One or more photo(s) has been virtually staged. Under Construction. Under construction. Experience approachable luxury combined with wellness-focused living in this newly crafted masterpiece by Urban Perch, a boutique home builder. In downtown Winter Park, this stunning new construction home offers 3,421 square feet of elegant, efficient living area. The primary residence features four bedrooms plus a generous flex space, the perfect office, home gym or playroom and 4.5 baths with designer fixtures and finishes. A separate casita with a full bath provides additional space for multigenerational living or as a private guesthouse. Upon entering, you are greeted by an expansive open-plan living area with soaring ceilings that effortlessly blends sophisticated style with indulging comfort. The kitchen is a culinary dream, equipped with Le Cornue and Monogram appliances, marble and quartzite countertops and a separate scullery with plenty of storage and ample prep space. The kitchen opens to one of the main living areas, featuring a precast concrete fireplace surround with exquisite millwork details, forming a focal point leading up to the angular ceiling and overhead beams. Engineered hardwood floors throughout and curated specialty tiles in wet spaces ensure the home maintains a clean, classic and modern feel. Floor-to-ceiling French doors and oversized sliders invite natural light and offer views of the beautifully landscaped grounds, including a sparkling heated saltwater pool and fully equipped outdoor kitchen. This wellness home incorporates advanced features to ensure a healthy living environment, from air and water purification systems to specialty lighting, all designed to promote a balanced lifestyle. Just moments from charming parks, highly rated restaurants and boutique shopping, 1627 Mizell Avenue is more than just a home, it’s a sanctuary. With excellent accessibility and a vibrant community, this is an ideal setting for those seeking a blend of suburban tranquility and urban convenience.

$3,300,000 Active

1627 Mizell Avenue Winter Park, Florida

5 Beds 6 Baths 3,421 SqFt 0.23 Acres

Under contract-accepting backup offers. 2026 PARADE OF HOMES ENTRY! - Positioned on an expansive corner lot in the heart of Winter Park, this extraordinary new masterpiece is a true architectural statement, delivering a level of craftsmanship and detail that is simply unforgettable. Framed by a massive front yard and a canopy of mature trees, the bold modern façade creates an immediate sense of arrival and sets the tone for what lies within. A grand set of double doors opens to a breathtaking two-story entry, where a dramatic marble mosaic feature establishes the home’s elevated design from the moment you step inside. The main living space is nothing short of stunning, anchored by a sleek electric fireplace and custom built-ins with integrated LED underlighting. At the heart of the home, the chef’s kitchen is a true showpiece, outfitted with Dekton Cosentino countertops, a paneled refrigerator, a full suite of Thermador appliances, and a hidden walk-in pantry. The kitchen flows effortlessly into the dining room which is bathed in natural light from an oversized statement window, making it perfect for hosting at any scale. Designed with versatility and luxury in mind, the home features two primary suites, one on each level. The downstairs primary offers soaring 12-foot ceilings and a serene, spa-like bath wrapped in marble mosaic tile. Upstairs, the main primary suite is a true showstopper, defined by its scale and attention to detail. Dual custom closet systems include an expansive hers closet complete with a dedicated makeup vanity, while the bathroom delivers a resort-caliber experience with stunning marble floors, a freestanding soaking tub, and dual vanities. The upper level continues to impress with a spacious loft designed for both relaxation and entertaining, complete with a custom entertainment center, wet bar, wine fridge, and a full bath. Each additional bedroom is ensuite, offering privacy and comfort for family and guests alike. Outdoor living rivals that of a private resort. A massive covered lanai features a fully equipped summer kitchen with tile backsplash, overlooking an expansive lounging area framed by a wall of glass. The heated pool and spa create the ultimate setting for year-round enjoyment, while the oversized front yard (an incredibly rare find in Winter Park), adds an unmatched sense of space and setting rarely found in this market. Additional features further elevate the home, including a sleek metal roof, striking hex LED lighting in the garage, and curated designer lighting fixtures throughout. Perfectly positioned just moments from Lake Chelton and Virginia Heights Park, with easy access to the boutiques and dining of Park Avenue and the charm of Hannibal Square, this residence offers a lifestyle that is as elevated as the home itself.

$3,290,000 Pending

1910 Glencoe Road Winter Park, Florida

4 Beds 6 Baths 3,788 SqFt 0.24 Acres

Under contract-accepting backup offers. Grand Southern charm and architectural elegance define this stately residence in one of Winter Park’s most desirable neighborhoods, set along a quiet brick-lined street just steps from Lake Chelton. Positioned on nearly half an acre, the home spans over 5,200 square feet, offering 5 bedrooms, 4.5 baths, a designated office, a large, versatile media/game room, a 3-car garage, and an expansive lanai with summer kitchen and resort style pool— all brought together in a smart well-planned layout ideal for effortless everyday living and exceptional entertaining.Step inside to a beautifully curated interior where rich architectural detail and livable design come together. Extensive custom millwork—seen in detailed moldings, trim work, and built-ins—adds depth and character throughout. The entry opens to gracious living and dining spaces, complemented by an impressive 550+ bottle temperature-controlled wine room.At the heart of the home, a beautifully appointed Kitchen, featuring white wood cabinetry, a six-burner gas range, an oversized quartz island, and a delightful breakfast nook that seamlessly connects to the family room featuring custom built-ins and fireplace—creating a natural gathering space.Tucked away, the first-floor primary suite offers a spacious sitting area, a beautifully customized closet with dressing area, and a luxurious bath with marble flooring, a large double-head walk-in shower, dual vanities, a free -standing tub, and built-in linen cabinetry—designed as a calming and private sanctuary.The first level also features a private guest bedroom with en-suite bath, creating an ideal setup for friends & family.A generously sized laundry room offers abundant cabinetry and exceptional storage, making everyday tasks feel effortless. Upstairs, three spacious bedrooms and two full baths provide comfortable accommodations, with two bedrooms opening through French doors to the front double balcony—perfect for enjoying peaceful treetop views.The back of the home unfolds around a beautiful pool and spa, with French doors from multiple rooms opening to the lanai and creating a natural indoor-outdoor connection. Retractable screens allow for year-round enjoyment of the well-appointed summer kitchen, making it ideal for both relaxed evenings and easy entertaining.Other notable highlights: a whole house natural gas generator, extensive brick paver driveway & motor court, automated driveway gate, integrated sound system, security cameras and new roof 2024.Lastly, this profound property offers top rated Winter Park schools and easy access to Park Ave, Downtown Orlando, Audubon Park Garden District and Baldwin Park.

$3,250,000 Pending

141 Glenridge Way Winter Park, Florida

5 Beds 5 Baths 5,243 SqFt 0.48 Acres

$3,235,000 Active

1821 Englewood Road Winter Park, Florida

5 Beds 6 Baths 3,863 SqFt 0.28 Acres

Under Construction. Just completed and ready to impress, this stunning custom-built residence delivers elevated design and effortless luxury in one of Winter Park’s most sought-after locations. Featuring 5 bedrooms and 4.5 bathrooms, this home blends timeless architecture with a fresh, curated aesthetic.From the moment you step inside, you’re greeted by warm wood flooring, custom millwork, and designer lighting that create a sophisticated, inviting atmosphere. The open-concept layout flows beautifully, centered around a showpiece kitchen with custom cabinetry, premium finishes, and an oversized island that anchors the space—perfect for gathering and entertaining. The great room is highlighted by a striking fireplace wall, adding depth and character.The first-floor primary suite offers a serene, private retreat, while a dedicated office with a full bath provides flexibility for guests or a refined work-from-home space. Upstairs, spacious secondary bedrooms and additional living areas offer comfort and privacy for family and visitors.Step outside to your own resort-style escape, complete with a sparkling pool, covered lanai, and fully equipped summer kitchen designed for seamless indoor-outdoor living.Ideally located just minutes from Park Avenue, top-rated schools, dining, and shopping, this newly completed home is a rare blend of style, comfort, and location.

$3,100,000 Pending

1351 Magnolia Avenue Winter Park, Florida

5 Beds 5 Baths 3,460 SqFt 0.24 Acres

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