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Luxury Homes in Winter Park

Properties
Nestled within the exclusive community of Windsong on Lake Berry, this magnificent 1.6-acre gated Mediterranean Estate is a true 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 that is rarely found in Winter Park. The home features 7 spacious bedrooms and 9 full and 2 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 own private gated entrance, this home is a one-of-a-kind opportunity to enjoy all of the amenities that Winter Park and Windsong have to offer. $11,900,000 Active

1120 Preserve Point Drive Winter Park, Florida

7 Beds 11 Baths 11,255 SqFt 1.63 Acres

CALLING HIGHEST AND BEST BY 4/30/2025!! Introducing a Unique, Stunning Modern Home A groundbreaking architectural masterpiece, this one-of-a-kind residence is built with reinforced concrete, steel, and iron framing, featuring floor-to-ceiling glass walls with no traditional windows. Designed to exceed Florida’s strictest building codes, this home follows commercial-grade construction standards, making it a bunker-style fortress unlike any other. Luxury Meets Modern Innovation Nestled in the heart of Historic Winter Park, Florida, this exceptional residence blends contemporary design with timeless elegance, offering unparalleled craftsmanship, high-end finishes, and an open-concept layout for those who appreciate architectural brilliance and luxury living. Key Features:     •    4,564 sq. ft. of living space     •    4 Bedrooms, 4.5 Bathrooms     •    Custom Costa One-Tree Solid Piece – A 16-foot steel masterpiece, a true work of art in the home’s design     •    Floor-to-ceiling impact-resistant Techno Glass walls—enhancing natural light and structural resilience     •    Imported Italian porcelain flooring throughout     •    All lighting fixtures imported from Greece, designed for maximum brightness and ambiance     •    Gourmet Chef’s Kitchen with:     •    1-inch thick Italian Quartz countertops     •    Imported Italian cabinetry     •    Extended island—ideal for entertaining     •    Top-of-the-line Wolf appliances & Sub-Zero refrigerator     •    Two Master Suites—one on each level, each with private luxury baths and custom walk-in closets     •    Private balconies crafted from exquisite boat wood, offering serene views and a tranquil retreat Exclusive Location & Lifestyle     •    Situated on a corner lot on Via Tuscany, one of Winter Park’s most exclusive and private streets     •    Just minutes from Interlachen Country Club, a historic private golf course     •    Short drive to Downtown Orlando and the best of Winter Park’s shopping, dining, and cultural experiences     •    Winter Park’s rich history and charming atmosphere make it one of Central Florida’s most desirable locations This architectural masterpiece is a true rarity, combining bunker-level resilience with breathtaking modern design. Experience the pinnacle of luxury living—schedule a private tour today. $8,799,000 Active

2661 Via Tuscany Winter Park, Florida

4 Beds 5 Baths 4,564 SqFt 0.36 Acres

Custom Waterfront Estate located in the heart of Winter Park with a covered Boat Dock on Lake Maitland - the largest of the Winter Park Chain of Lakes. A timeless Neoclassical Italian home that exudes luxury and sophistication, spanning a total of 7,916 square feet. Built by Charles Clayton. Designed by Marc Michaels. The main house boasts over 7,100 sf with 4 bedrooms, 4 full bathrooms, and 3 half bathrooms. The detached Guest House/In-Law is approx. 500 sf, with 1 bedroom, 1 bathroom, two closets, and a wet bar. The detached Catering Room with half (pool) bath is approx. 350 sf with an additional refrigerator and wall-to-wall storage, conveniently attached to one of the two-car garages. Recently upgraded with a NEW barrel tile ROOF installed in 2023. Enjoy expansive entertaining areas that seamlessly blend indoor and outdoor spaces, offering a grand setting for lavish gatherings. Outfitted with the finest custom finishes, gourmet chef's kitchen, equipped with top-of-the-line appliances, an oversized island, and large dinette space. Awe-inspiring private courtyard with heated pool and spa, covered porch, outdoor grill, and several separate terraces. Impressive primary suite with office and sitting area has separate his and hers ensuite bathrooms and closets. Stunning two-story closet with office on the second floor and laundry room on first floor. Impressive entertainment/media room with state-of-the-art projector, media equipment and electronic blackout shades. Second story features a spacious loft, 3 bedrooms, 2 full bathrooms, a laundry room and two balconies. Storage is abundant throughout this property. You will find two 2 car garages behind the electronic gated side facing driveway, one garage with a kennel and a Tesla charging station. Experience quintessential Winter Park living in this one-of-a-kind estate that is the epitome of opulence and grandeur. $6,500,000 Active

1400 Alabama Drive Winter Park, Florida

5 Beds 9 Baths 7,916 SqFt 0.7 Acres

*Price Improvement* The sellers received an unexpected opportunity and are relocating out of state, so the house is priced to sell quickly. Walk in with instant equity in this once in a lifetime lake home. Welcome to your dream home in the heart of Winter Park, Florida! Nestled in the prestigious Timberlane Shores neighborhood, this exquisite custom-built residence by Farina & Sons offers the perfect blend of luxury and tranquility. With 4 bedrooms, 3.5 baths, and a generous 4,725 sq ft of living space, this home is an Aurora and Parade of Homes Grand Winner and boasts 130 ft of lakefront frontage on the serene Lake Virginia. As you approach this stunning property, you'll find it situated on a quiet cul-de-sac, ensuring peace and privacy. Step into the backyard oasis, where a lanai with a gas fireplace invites you to unwind and enjoy Florida's beautiful weather. Relax in the hot tub or take a dip in the pool equipped with an Ultraviolet System which ensures the healthiest pool water possible, complete with an outdoor shower. The outdoor home lighting creates an enchanting ambiance, while the boat dock with a covered electronic boat lift offers easy access to water adventures. Experience breathtaking sunrises and sunsets over Rollins and Knowles Chapel from your own piece of paradise. The first floor of this home is designed for both comfort and style. Anderson doors and windows fill the space with natural light, highlighting the wood floors and architectural details like coffered ceilings with wood beams in the open family room. The master suite serves as a private retreat, featuring a spa bathroom, custom closets, and ample storage. Two additional bedrooms, a bathroom, and a half bath provide versatility and convenience. The kitchen is a chef's delight, boasting Caesarstone concrete countertops, a copper hood range, top-of-the-line Subzero and Viking appliances, walk-in pantry. A walk-in bar and wine room enhance the home's functionality, while a Pelican whole house water filtration system and a Kangen Leveluk water purifier ensure the highest quality water. The second floor is perfect for entertaining, offering a spacious area with a bonus room, bar, kitchenette, and an additional bedroom with an en-suite bath. This versatile space is ideal for hosting guests or creating a personal retreat. The city of Winter Park has approved plans to add an enclosed 385 square feet to the second floor, providing potential for additional space. Don't miss the opportunity to own this extraordinary lakefront home in one of Winter Park's most sought-after neighborhoods. Experience luxury living at its finest with unparalleled lakefront views, exceptional amenities and convenience to all the restaurants and shopping that Winter Park has to offer. $5,800,000 Active

541 Virginia Drive Winter Park, Florida

4 Beds 4 Baths 4,725 SqFt 0.51 Acres

Experience refined luxury in this newly constructed 2024 Hamptons-style residence, a seamless blend of elegance and modern sophistication. A remote-operated gated entrance opens to a grand circular driveway and private motor court, setting the stage for this exceptional estate. The two-story foyer impresses with a glass-paneled staircase that wraps around a temperature-controlled wine room and a transparent glass elevator, effortlessly connecting all levels, including an expansive third-floor multi-purpose retreat. Designed for contemporary living, the thoughtfully curated floor plan features a spacious open-concept gathering room with multiple French doors leading to a covered lanai. The dining area, framed by a striking glass wall, overlooks a serene backyard with a sparkling pool and spa. The main residence offers four private bedroom suites, complemented by a detached pool cabana that serves as a fifth bedroom or versatile guest retreat. A hidden office, den and an expansive upstairs lounge provide flexible living spaces ideal for a media room, bar or billiards area. 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 first-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. The second level hosts three additional bedrooms with en suites, a generous family lounge, a bar, a full bath and a well-appointed laundry room with extensive cabinetry. The third level, accessible by the staircase and elevator, offers nearly 770 square feet of adaptable space. 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. The detached cabana offers flexibility as 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 plumbing and electrical fixtures, and Trane HVAC system, 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 state-of-the-art car lift providing space for three vehicles. Ideally near Interlachen Country Club, Winter Park Racquet Club, Phelps Park/YMCA, and renowned Park Avenue, this exquisite estate offers an unparalleled lifestyle. Note: Partial staging by Restoration Hardware. The furnishings package can be purchased separately. $5,200,000 Active

1660 Palmer Avenue Winter Park, Florida

5 Beds 7 Baths 6,406 SqFt 0.36 Acres

Gorgeous Winter Park home beautifully curated with designer details and recently featured in June’s “Orange Appeal” and was the 2022 Mystery Home Tour selected by Council of 101 for the Orlando Museum of Art. This elegant transitional French Provincial residence is located on a large, elevated corner lot in a quiet and secluded area in the Via’s of Winter Park. This designer home has been significantly enhanced inside and out by the current owner and is in “brand new condition.” The home features 5,100 square feet of living space and 800+ square feet of outdoor space with 5 bedrooms, 5 bathrooms, 1 half bathroom, 3 car garage, pool, patio, outdoor shower and professionally landscaped yard and lighting. Upon entry, you are welcomed through the exquisite foyer where you instantly notice the craftsmanship and expert care that went into the custom carpentry and crown molding details throughout. To the left of the foyer is an elegant and intimate parlor with grass cloth wallpaper, a gas vented fireplace and built-in bookshelves. To the right of the foyer is the formal dining room with beautiful hand painted wallpaper and an adjacent butler’s pantry. Past the foyer you are led to a spacious and grand formal living room with lacquered walls and 6 new French iron doors that flow out to a covered brick porch and picturesque back yard & pool. Designed with entertainment in mind, the adjoining chef’s kitchen includes newly painted custom cabinetry, a Sub-Zero/Wolf appliance package, a grand center island and a walk-in pantry. Built in desk and casual dining area all open to the adjoining beamed ceiling family room with gas vented fireplace and additional French doors that lead to street side patio with new awnings. First floor master retreat overlooks the pool & yard and features 14-foot wood beam vaulted ceilings. The oversized master bath with double custom lacquered vanities made in Palm Beach, mosaic marble shower and a Waterworks free standing tub, brushed brass fixtures, and walk in closet. The second-floor features nine-foot ceilings with four bedrooms (one which was converted to a beautiful women’s dressing room) and four ensuite bathrooms, covered balcony adjoining two bedrooms, two built in desks and bookshelves for office/study time and large media room with big screen tv and wet-bar. There are also two laundry rooms, one upstairs and one downstairs. Attic space inside the home and inside the garage. Recent upgrades include new slate roof/swooped decorative copper roof with chimney caps, complete chimney rebuild, nine new iron French doors, new ebony-stained oak hardwood floors, lacquered walls, newly renovated master bath and two ensuite baths. This home offers boat access to the Winter Park chain of lakes and is within short distance of the Winter Park Racquet Club. It’s also a bike ride away and a short drive to the Interlachen Country Club and Park Avenue shopping and dining district. The property is zoned for Dommerich Elementary, Maitland Middle School, and Winter Park High School. $5,000,000 Active

2228 Azalea Place Winter Park, Florida

5 Beds 6 Baths 5,072 SqFt 0.33 Acres

New Home Nestled in the esteemed The Vias area and near the WPRC. Situated on a secluded street, it occupies an approximately 0.58-acre lot with an expansive backyard landscape that is truly captivating. This exquisite home encompasses five bedrooms and six-and-a-half bathrooms with a four-car garage. An indomitable presence is seen in its immense and grand pivoting iron door which directs you to a double-height foyer and great room separated by a glass-railing catwalk. The property boasts exclusive features like a formal dining room endowed with a glass-encased wine display as well as an intimate den/office safeguarded by private entrance doors. The airy master bedroom is adorned with sliding doors that open up to reveal a private lanai overlooking the pool area; one cannot overlook its distinctively vast his-and-hers walk-in closets complemented by a spa-like luxurious bathroom suite. A state-of-the-art kitchen featuring gold Calacatta Quartz countertops/backsplash matched alongside an oversized walk-in pantry, creating everyday usability flanked with indulgence! Two separate upper and lower level laundry rooms serve this expansive open floor plan a win-win situation for convenience! Adding exceptional charm to this stunning home is a family room equipped with zero corner sliding doors opening up towards the summer kitchen leading onto a large covered patio encased in travertine pavers-- making it your personal haven for enhancing entertainment moods. Venturing upstairs via an elegant Quartz staircase leads you to an additional four en-suite bedrooms (each with walk-in closets). Complementing your leisure needs flawlessly are a comfy lounge space and fun-filled game room with a wet bar setup; creating a direct pathway onto a sprawling balcony exhibiting glass railings overlooking backyards - commanding mesmerizing views of your saltwater gas-heated pool and cozy gas firepit with a seating area for social gatherings! A dedicated full-bath pool with a steam shower. Home gets fully enveloped using high-quality materials fashioned from Large Porcelain format tiles, European tiles, Travertine pavers, and Swiss-origin WPL catering to its strength quotient. Tor uniquely detailed outlook, the property also offers a detached additional building that has been thoughtfully renovated to deliver an extra 600 sq ft of living space - not part of the main house size calculation (6475 sq ft). With 1 bedroom, 1 full bath, a fully functional kitchen surrounded by a living area, and a covered/tiled porch; it makes for a rare addition delivering discernible usefulness. Think creativity! Convert it into a guest house, in-law suite, gym space, professional office setup, or even a hobby room - multiple endless usage options make its possession a valued choice! The home is available now and move-in ready! Get one step closer to owning the realization of your dream dwelling experience! $4,750,000 Active

2161 Sharon Road Winter Park, Florida

5 Beds 7 Baths 6,338 SqFt 0.58 Acres

"The Point House" on lake Killarney. Rarely available oasis, this spectacular lake front residence is positioned on a peninsula with .90 acres and over 440+ feet of lake frontage with unobstructed lake views to the south, west and east. Constructed in 2012, this home features 6,000 living square footage (3,977 on the 1st level / 1,950 on the 2nd level), 4,000 sq. ft. of outdoor space, elevator, infinity pool, boat house and tennis court. Main level offers 35 x 32 great room w/kitchen and dining, a separate dining area, 36 x 20 family room with bar/wine room, 4 bedrooms/ 3.5 baths, laundry room and 4 multi slider panel doors that open to wrap around patio with outdoor kitchen. 2nd floor offers a 2nd laundry room, lofted library, guest bedroom and primary bedroom with suite/lounge/built in wet bar and additional 4 multi slide panel doors that open to a wrap around balcony. Experience the serenity and tranquility of old Florida under the majestic cypress trees beaming with wildlife/eagles/beavers and the ever changing landscape from sunrise to sunset. $4,600,000 Pending

2118 Lake Drive Winter Park, Florida

6 Beds 6 Baths 6,000 SqFt 0.91 Acres

Welcome to Lincoln! This new construction single family home has been meticulously crafted and constructed by Wooten Built, a locally established, award-winning developer and luxury home Builder. Location! Location! Location! Lincoln Circle is a quiet street next to Park Avenue restaurants and shopping. Easily walk to Winter Park shops, restaurants, and the Winter Park Golf Course. This bespoke home includes premium features, appliances, fixtures and finishes as follows: Elevator, Wolf/Sub-Zero appliances, wine cooler tower, built-in coffee maker, Lutron RA3 Automation, wired for security with plenty of camera drops, whole-house audio pre-wire featuring Sonos speakers and 5.1 surround, first floor primary bedroom with ensuite washer/dryer, additional guest suite first floor, 11’4” first floor ceilings and custom 10’ solid core DOORS, wet bar, large vaulted upstairs living room, large flex-space upstairs bonus room, trey ceilings, huge front entry window and door system, two 10’x10’ full-view garage doors, circular driveway, full-house natural gas generator, heated pool with spa and fire & water bowls, plenty of pool deck space, and exquisite landscaping. Smart glass covers the large ~14’ x 10’ front entry system… Choose frosted for privacy or transparent/thru-view at the press of a button! A 6’ masonry-stucco wall encompasses the property. The rear cabana/pergola houses the summer kitchen, pool bar, pool-bath and outdoor shower. Enjoy two fireplaces!: a 100” linear electric fireplace in living room and a 60” linear natural gas fireplace by the pool deck. Inquire with agent for more information. $4,599,000 Pending

985 Lincoln Circle Winter Park, Florida

5 Beds 7 Baths 3,660 SqFt 0.23 Acres

This elegant Winter Park lakefront residence offers luxury lakeside living, situated on the picturesque shores of Lake Osceola. This exquisite home invites you in with a grand circular driveway and meticulous, landscaped grounds, combined with elevated panoramic views from a spacious 3/4 acre lot, with approx. 140 feet on the street and approx.. 110 feet of prime lake frontage. This property offers a sense of privacy, tranquility and breathtaking views capturing both northern sunrises & sunsets… Inside, you'll find extensive renovations, over the years, that have elevated the space enhanced with Wolfe-Rizor Interior Design elements… There is plenty of natural light throughout, with extensive windows, numerous French doors and a thoughtful layout that seamlessly blends indoor and outdoor living spaces. The primary level includes a defined foyer entry, secluded library/home office, kitchen, gathering room, formal living and dining rooms. The chef’s kitchen is thoughtfully designed and enhanced by an expansive island, commercial grade range, lake side breakfast room, and catering area for creating culinary experiences in hosting family and friends. The lavish living room includes room for a grand piano and has its own fireplace open to an expansive 30’ long dining room with direct lake views… along with a screened lanai... The primary suite is conveniently located on the ground floor, offering a private expansive retreat with a sitting area and serene, picturesque lake views. The luxurious primary bathroom provides a spa-like experience including modern fixtures, his/her separate baths, and a generous walk-in closet/dressing room. The main level also includes a potential 6th bedroom used previously for a caretaker’s quarters tucked away by the garage entry... The upstairs living areas, include 4 additional bedroom suites (generous sizes) located on the second floor with a couple of bonus/flex rooms and sitting area... When you're not savoring the indoor elegance, step outside to enjoy the lakefront living with entertaining terrace, tropical pool, sprawling lawn with retaining walls, boathouse and majestic cypress, oak & palm trees to enhance the lakefront lifestyle... Located on private, quiet street with oversized 3-car garage… Note: roof replaced in 2021. All within walking distance to downtown Winter Park and famed Park Avenue… $4,500,000 Active

421 Lakewood Drive Winter Park, Florida

5 Beds 9 Baths 5,847 SqFt 0.72 Acres

Under Construction. New Custom Home in the Desirable Winter Park Via’s – Completion Expected June 2025 This exceptional residence, designed with European English Tudor-inspired architecture, offers the perfect blend of timeless charm and modern luxury. Close to Park Avenue, the home is crafted by Winter Park Design and Floridian Custom Homes, with interiors curated by Brianna Michelle Interior Design and landscape & pool design by Signature Landscape. Every detail of this home has been meticulously planned, from the handcrafted cabinetry to the luxurious natural stone and quartz countertops. Custom woodwork throughout the main living areas and master suite exudes craftsmanship and sophistication. Wide-plank European oak flooring and natural stone accents add warmth and elegance to every room. Details, details, details! Exterior Features:?The home's striking exterior features an authentic clay brick façade, smooth steel trowel stucco, and exposed wide-beam rafters and tails. Enjoy the beauty of exposed tongue-and-groove decking and a tile roof, paired with Anderson clad windows and custom mahogany doors. Additional highlights include seamless gutters, brick and natural stone pavers, and an attached brick-clad cabana. The outdoor space includes a custom-tiled heated pool with therapy jets, lounging areas, a privacy wall, custom gates, and expertly designed landscaping that ensures ultimate privacy and beauty. Gourmet Kitchen: Designed for the most discerning chefs, the kitchen features custom furniture-grade cabinetry, a La Cornue range, a custom copper hood, and top-of-the-line Thermador refrigerator and freezer columns. The space also boasts beverage drawers and a spacious back kitchen/pantry, providing ample storage and functionality. Every inch of this kitchen has been carefully crafted to impress. Master Suite Retreat: The master suite serves as a serene escape, featuring custom woodwork, a cozy sitting area, and stunning wood floors. The master bathroom is equally luxurious, with marble finishes, custom cabinetry, and a spacious walk-in closet designed for the most refined tastes. Additional Features: * 3,720 SF of A/C space * Four spacious bedroom suites * Private study with a full bathroom (can function as a 5th bedroom or nursery) * Upstairs loft/bonus room * Large two-car garage * Separate mudroom and back kitchen/pantry * Open great room for seamless entertaining This brand new custom home offers the ultimate Winter Park lifestyle in one of the area's most sought-after neighborhoods, with easy access to Park Avenue and a thoughtfully designed layout that combines modern convenience with old-world charm. The perfect home for those seeking luxurious living and refined elegance. $4,500,000 Active

702 Via Bella Winter Park, Florida

5 Beds 6 Baths 3,720 SqFt 0.23 Acres

One or more photo(s) has been virtually staged. Discover a stunning blend of modern luxury and award-winning design in this architectural gem by Phil Kean. Originally the International Showcase Home for the National Association of Home Builders, it has received numerous accolades for its exceptional design and construction. Location! Location! Location! On one of Winter Park’s most desirable streets, this home offers a lock and leave lifestyle just steps from the Alfond Inn and downtown’s vibrant offerings. With 4,431 square feet of beautifully designed space, it balances privacy and urban convenience, featuring a serene outdoor lanai with a sleek pool, and a summer kitchen, your private oasis for relaxation and entertaining. The versatile casita can serve as a pool cabana, guest house, gym or office. Inside, enjoy sophisticated spaces, including a 14-foot ceiling art gallery with 40-feet display wall leading to an inviting bar, ideal for gatherings. A modern elevator connects both levels, enhancing accessibility. The primary retreat on the second level features a spa-like bath, three private terraces and a media room, designed for ultimate relaxation. Additionally, a versatile room with full bath on second floor that can serve as a bedroom, gym, office or dressing room. Technology integrated home and energy-efficient features, including a whole-house generator, ensure modern living and peace of mind. Outdoor spaces boast low-maintenance landscaping and a dedicated dog run, making this home ideal for effortless living. Experience luxury, innovation and convenience in one of Winter Park’s sought-after locations, moments from dining, shopping and cultural experiences. $4,395,000 Active

229 Alexander Place Winter Park, Florida

4 Beds 6 Baths 4,431 SqFt 0.27 Acres

Just Listed ~ Stunning lakefront home in Winter Park that has been completely remodeled and offers 4 bedrooms, a bonus room, and guest apartment! This home is exquisite from top to bottom and features elevated ceilings, crown moldings, designer fixtures and wall coverings. Large picture windows overlook Lake Sue from the living room, dining room, and kitchen. The kitchen is gorgeous and offers chef-grade appliances, a large center island, plenty of soft-closed cabinetry for storage, and an open-concept layout for inclusive entertaining. French doors open off the family room to seamlessly blend the indoor/outdoor living space. A covered lanai with outdoor kitchen overlooks the beautiful, resort-inspired, heated pool and spa, multi-level summer terrace with gardens, and the custom 3-hole putting course. Back inside, located on the 2nd floor, the primary suite has a Juliette balcony that overlooks the shores of Lake Sue and features an en suite bath with a double-headed shower, separate soaking tub and double-sink vanity. An oversized guest suite with private bath and two bedrooms and a hall bath complete the second floors. On the first floor is a bonus room (ideal for use as a playroom, home office, or studio), a full bath, and laundry room. Above the detached 2-car garage is an apartment with a kitchenette and full bath with walk-in shower. The expansive 0.58 acre property extends over the charming brick street and includes a large, park-like green space, shaded beneath majestic oaks, s small beach area, elongated dock, and boathouse (no lift). Located within minutes of Park Avenue, this lakefront estate is a short walk or bike ride to nearby shops and dining and is zoned for one of the best school districts in the area. Audubon Park, Baldwin Park, the Mills District, and Downtown Orlando are all within a 10-minute drive. Showings are by appointment only – schedule yours today. $4,395,000 Active

1840 W Fawsett Road Winter Park, Florida

5 Beds 5 Baths 4,129 SqFt 0.58 Acres

Under contract-accepting backup offers. Pre-Construction. To be built. Welcome to Winter Park lakefront living at its finest. In the heart of Winter Park, this new construction residence promises to be a masterpiece of luxury and modern living. Spanning over 5,500 square feet, this magnificent lakefront residence offers an unparalleled lifestyle with breathtaking panoramic sunset views. Tolaris Homes, an esteemed custom builder in Central Florida with over 45 years of expertise, will guide you from conceptualization to realization of your dream home. Designed to capture the essence of serene lakeside living, the home is ideally positioned to provide scenic vistas of the water and the vibrant hues of the setting sun. As you step onto the expansive balcony, the splendor of this property unfolds. The balcony, designed for relaxation and entertainment, offers a front-row seat to nature's nightly show, where the sky transforms into a canvas of oranges, pinks and purples. Imagine enjoying a glass of wine or hosting a gathering with friends and family, all while soaking in the tranquil beauty of the lake and its surroundings. Inside the home, elegance blends harmoniously with modernity, featuring spacious open-plan living areas that seamlessly transition from one room to the next. High ceilings and large windows ensure natural light illuminates the interior, enhancing the feeling of openness and connection to the outdoors. The thoughtful design includes luxurious finishes and state-of-the-art amenities, catering to every need and desire of its future owners. Experience the ultimate lakefront lifestyle with year-round boating, kayaking and water skiing on your private lake in Florida. Lake Killarney is one of the few lakes in Central Florida where you can land your seaplane on the water. Beyond the walls of this exquisite home, Winter Park offers a vibrant community rich in culture and amenities. From upscale dining and shopping to outdoor activities and renowned schools, this location balances convenience and exclusivity. $4,200,000 Pending

571 Lake Front Boulevard Winter Park, Florida

7 Beds 5 Baths 5,500 SqFt 0.48 Acres

Under Construction. UNDER CONSTURCTION.....Step into this stunning West-Indies inspired luxury home crafted by Nautilus Homes, where tropical charm meets timeless elegance. An architectural masterpiece in the heart of City of Winter Park. Exquisite Interior Features that are offered starts with entering the grand foyer with 10ft high ceiling and the flex room and formal dining to your left and right. Followed by entering the gallery that leads to the massive grand room. The Chef’s Kitchen, a culinary dream featuring an oversized center island, quartz countertops throughout, custom 42"+15" 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. Heading to the second floor that has 10ft ceilings as well. As you reach the top the space opens into a massive game room and entertainment retreat—designed for both relaxation and celebration. All second-floor bedrooms have a thoughtfully design with full a 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. Welcomed with elegant pavers and recessed lighting, effortlessly extending your living space into the open air. Just beyond, the sparkling 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 seamless indoor-outdoor flow creates the ultimate setting for enjoying the Florida lifestyle in style and comfort. Finally, tucked away with its own private entrance on 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 small refrigerator and sink—ideal for extended stays or multi-generational living. Whether used for guests, family, or as a private retreat, this suite provides a quiet, self-sufficient escape with all the essentials of home. This masterpiece includes a full irrigation system around the home, exterior lighting, exterior cameras for security and includes a fully controlled smart home system for your convenience. The home welcomes you with a beautifully designed U-shaped driveway wrapped in upgraded pavers, offering both elegance and functionality. a spacious 4-car garage and abundant parking, there's plenty of room for guests to arrive in style. Interlachen Golf community less than 5 min, Park Ave 10 min and restaurant and retail minutes away. Schedule your private tour today. $4,100,000 Active

1782 Pine Avenue Winter Park, Florida

5 Beds 7 Baths 4,782 SqFt 0.36 Acres

Presenting a stunning luxury estate in the highly coveted Windsong community with access to the gorgeous Winter Park chain of lakes. Prepare to be impressed as you enter this almost 6,000 square foot home adorned with custom high-end features throughout, plus a fabulous guest apartment with a full bathroom and kitchenette fully renovated to be enjoyed as a private poker/bourbon room. This exceptional residence has been converted to a full Smart Home with integrated controls for lighting, audio/video, security system with cameras, intercom, thermostat and sun shade. The beautiful chef's kitchen boasts a brand new 48” Sub-Zero refrigerator, and all new Wolf appliances including double 30” electric ovens, microwave, gas cooktop, hood insert, and warming drawer. For added convenience, a fully appointed Butler's pantry is adjacent to the kitchen. Retreat to the stunning first floor owner's suite featuring a newly installed electric fireplace, sitting area, a walk-in closet with custom cabinetry, a separate office/home gym and a spa-inspired bathroom with a jetted tub and steam shower. Just outside, step into your own personal wellness retreat with a new Polar Monkey brand cold plunge and a four-person sauna. Also, guests will enjoy the convenience of another private first floor bedroom suite. Upstairs are the additional three spacious bedrooms and bathrooms, a huge loft area, and hidden stairs leading to a generous air conditioned storage room, great for a home theater. The outside oasis greets you with a fully reimagined expansive covered lanai with an outdoor kitchen complete with a 60" Fire Magic grill, 60" Fire Magic vent hood, Summit refrigerator, and stainless steel cabinets. Relax by the sparkling saltwater pool with its sun shelf, retractable screen, and travertine deck surrounded by lush tropical landscaping and artificial turf for carefree living. The extensive renovations to this luxury estate continue with the installation of a new roof, new gutters with leaf guards, freshly painted exterior, new wood trellis, all new saltwater pool equipment, and epoxy garage flooring with added custom cabinets. Embrace this luxury lifestyle with exclusive access to the Windsong Residence Club overlooking the Winter Park Chain of Lakes, with amenities including lake access, community pools, splash park, playground, and use of the pontoon boat. This home may be purchased fully furnished. Don't miss the opportunity to own this spectacular home in one of Winter Park's most sought after neighborhoods with its top-rated schools, and proximity to shopping and dining on Park Avenue in picturesque downtown Winter Park! $3,980,000 Active

141 S Phelps Avenue Winter Park, Florida

6 Beds 6 Baths 5,878 SqFt 0.28 Acres

Nestled on a sprawling 0.89-acre estate, this luxurious home offers the perfect balance of privacy and convenience, just moments from the vibrant downtown Winter Park. A rare gem, this 1935 James Gamble Rogers masterpiece blends Old World charm with European influences, creating an inviting, character-rich ambiance. The main home features 3 bedrooms, 2 1/2 bathrooms, and 3,908 square feet of elegant living space, complemented by a 1-bedroom, 1-bathroom guest cottage, adding 406 square feet, for a total of 4,314 square feet. Accessed via a long, secluded driveway, this estate seamlessly blends indoor and outdoor living with lush gardens, expansive courtyards, and tranquil patios. Inside, arched doorways, reclaimed doors, and rounded stucco walls evoke a Santa Barbara Mediterranean feel. The kitchen is outfitted with stainless steel appliances, granite countertops, and a butler’s pantry—ideal for entertaining. The formal dining room opens to a living room with a curved barrel ceiling, a fireplace, and French doors leading to a garden patio. A sunlit sunroom offers panoramic garden and pool views, perfect for relaxation. The expansive downstairs owner's suite features vaulted ceilings, French doors to the patio, a cozy fireplace, and a lavish marble bath with a Jacuzzi tub, double sinks, and a dressing area with custom cabinetry and two large walk-in closets. Upstairs, two bedrooms share a beautifully renovated marble bath. The detached 2-car garage is adjacent to the laundry room, while the guest house offers a studio layout with terra-cotta floors, a kitchenette, a full bath, and French doors overlooking the pool. The backyard is an oasis of tranquility with a stunning resort-style pool, an expansive patio, and lush landscaping, providing ultimate privacy. This home offers the best of both worlds: a rare opportunity to own a piece of Winter Park history, yet lovingly maintained with modern updates and conveniences throughout. $3,950,000 Pending

851 Georgia Avenue Winter Park, Florida

4 Beds 4 Baths 4,314 SqFt 0.89 Acres

Nestled on one of Winter Park’s most picturesque brick-lined streets, this stunning Mediterranean residence offers a refined blend of timeless elegance and modern luxury. With six bedrooms, six full baths, and two half baths, this expansive 6,939-square-foot estate is designed for both grand entertaining and intimate everyday living—and is ideally suited as a multigenerational home. Originally built by esteemed custom homebuilder Ira Kitograd and recently renovated by George Driscoll, the property features a complete gut and renovation of the kitchen, family room, and luxurious master bath, elevating the home’s design, flow, and functionality with exceptional craftsmanship and designer finishes. Beyond the arched glass French doors, the formal living room opens to a charming courtyard-style pool area, while a dedicated office with a fireplace and built-in bookshelves provides a quiet retreat. A guest suite with an ensuite bath offers private courtyard access. The formal dining room leads to a sprawling chef’s kitchen featuring two oversized islands, high-end appliances—including a Lacanche range and Sub-Zero side-by-side refrigerator with a glass door, refrigeration drawers, warming drawers—a walk-in pantry, and a butler’s pantry. Overlooking the kitchen, the family room showcases a vaulted arched ceiling, a fireplace, and a concealed TV with a remote-controlled screen. A study with a built-in desk and custom cabinetry is tucked off the family room, while a wall of glass sliders seamlessly connects the indoors to the covered lanai and courtyard. The private primary suite features a sitting area, an elegant renovated marble bath with a walk-in shower and marble flooring, and a custom walk-in closet. The second floor includes a media room with a large screen and equipment, a den or bonus room, and three additional bedrooms, each with an ensuite bath. Internet is hard-wired on both floors, making this home ideal for gaming, streaming, and working from home. Two laundry rooms, one on each level, add to the home’s convenience. The outdoor living spaces are designed for both relaxation and entertaining, with a covered lanai, an expansive terra-cotta pool deck, and a sparkling pool framed by towering palms and lush Birds of Paradise. A long driveway leads to the rear-entry three-car garage, complete with a tremendous amount of custom storage cabinetry. Both the front and rear garages are air conditioned, and the main house’s attached one-car garage includes a universal car charging station. Above the detached garage sits a spacious guest house, perfect for a nanny, estate manager, or visiting guests, featuring a living room, built-in kitchenette with wine refrigeration, beverage coolers, a microwave, and French doors leading to a private bedroom. The guest house’s balcony overlooks the pool and courtyard, offering serene views and added privacy. A circular driveway with a centerpiece fountain enhances the estate’s meticulously maintained curb appeal. Situated in the heart of Winter Park, this exquisite property offers the perfect blend of sophistication, comfort, privacy, and location. $3,850,000 Active

861 Bonita Drive Winter Park, Florida

6 Beds 8 Baths 6,939 SqFt 0.59 Acres

On one of Winter Park’s most scenic brick-lined streets, this exceptional two-story residence commands attention on a spacious corner lot, blending timeless architectural elegance with modern luxury. Built in 2016 by the highly regarded Rex-Tibbs Development & Construction, the home showcases quality craftsmanship throughout, from its striking curb appeal to its impeccably appointed interiors. A three-car side-entry garage, air-conditioned and offering generous storage, is connected to the home via a covered walkway, adding functionality and charm. Inside, beautiful wood floors extend seamlessly throughout the entire home, including all bedrooms, creating a warm, cohesive atmosphere. The main level offers an elegant formal dining room and a flexible front room that can serve as a home office, library or formal living area. The heart of the home is the expansive family room, anchored by a gas fireplace and illuminated by natural light through large sliding glass doors that open to the lanai and pool. Overlooking the family room, the open-concept kitchen is a culinary dream, featuring a Wolf six-burner gas range with double ovens, Sub-Zero refrigerator, abundant cabinetry and expansive counter space, ideal for everyday living and entertaining. The first-floor primary suite is a retreat, with French doors leading directly to the pool area, a luxurious spa-style bath, and a custom 14-by-10-foot walk-in closet designed for maximum organization and style. A secondary primary suite, also on the main level, includes a generous walk-in closet and a private en-suite bath, offering flexibility for guests or multigenerational living. Upstairs, the home continues to impress with a spacious recreation/game room, a separate bonus room and three additional bedrooms, all of which feature en-suite baths and walk-in closets, ensuring comfort and privacy for family and visitors alike. Step outside to experience resort-style living at its finest. The covered lanai is equipped with a fully outfitted summer kitchen, including a built-in grill, while the pool area is a showstopper, complete with a dramatic gas fire display, tranquil waterfall, ambient lighting, and a lush wall of bamboo that enhances privacy and lends a tropical ambiance. A separate outdoor cabana with TV and seating area offers a place to unwind or entertain in style. Beyond the home, the location is unbeatable. In one of Winter Park’s most desirable neighborhoods, you’re just minutes from the upscale shops, fine dining and cultural attractions of Park Avenue. The home is also conveniently close to top-rated public and private schools, premier medical facilities and major transportation hubs, including the Orlando Executive Airport and Orlando International Airport, ensuring ease of access for business and leisure travel alike. This remarkable property offers the ultimate in refined living, combining luxury, comfort and convenience in one of Central Florida’s sought-after communities. $3,750,000 Active

2171 Forrest Road Winter Park, Florida

5 Beds 6 Baths 4,565 SqFt 0.25 Acres

Welcome to a stunning new home positioned near Windsong and the AdventHealth Hospital. This extraordinary property boasts 4,812 square feet under AC. The stately manner is thoughtfully designed with four commodious bedrooms and five full-size bathrooms. Additionally, it features an expansive three-car garage complemented by an impressively constructed circular paver driveway. The first floor showcases lofty 11.4-foot ceilings, while the second floor features equally impressive 10-foot ceilings. A plentiful array of windows and numerous sliding doors augment the home's overall charm by inviting a flood of natural sunlight. A medley of Lutron dimmers and smart switches grants effortless convenience at your fingertips. You will be warmly welcomed by a majestic steel glass hurricane impact door. Upon setting foot into this marvelous residence, one is instantly greeted by the glow of Oak wood floors, thoughtfully woven throughout each corner of the abode. Well-appointed Walnut and Oak wall panels add an unparalleled layer of understated luxury to this remarkable home. The kitchen is a visual treat with an expansive waterfall island dominating the space. Floor-to-ceiling cabinets deliver abundant storage while the gleaming Quartz countertops exhibit both beauty and durability. To add to its grandeur, a matching Quartz backsplash extends all the way to touch the ceiling, seamlessly melding simplicity with luxury. The kitchen comes fully equipped with all Thermador appliances, ready to cater to your every culinary need. This suite of top-tier appliances includes a grand 72-inch combo Freezer/Wine Tower/Fridge, a natural gas 48-inch Range with a steam oven guarantees an enjoyable cooking experience each time. Two fully equipped laundry rooms, one located on each floor. The master bedroom features an expansive sliding glass door leading you directly to the tranquillity of the sprawling backyard. The master bathroom is a serene, spa-like haven designed with luxurious Italian tiles, a natural stone accent wall that lends an air of sophistication. The floating cabinets add to the modern aesthetic and are enhanced by the backlit marble countertops, radiating a soft glow, adding to the relaxing atmosphere. The second floor boasts 3 well-appointed bedrooms and corresponding bathrooms, each outfitted with Marble countertops that enhance their plush ambience. Uniquely offering versatility, a large flex area graces this floor, which could be customized according to your liking or needs. Ensuring fun entertainment spaces within the confines of your home exists a game room too, catering to all age groups! The special feature is an in-built wet bar complemented by Cristallo Quartzite counters and custom cabinetry, thus serving as an ideal indoor party venue. As an extension of indoor living space, the outdoors is a sizeable terrace accented with contemporary glass railings. Yes, the backyard is a true oasis in this property. A large covered lanai provides ample space for relaxation or outdoor dining. The summer kitchen features state-of-the-art appliances to assist in making your entertaining dreams come true. No luxury home would be complete without a pool, and this one comes with a gas-heated saltwater pool and a spa. A full pool Bathroom with a Steam Shower. Travertine pavers enhance the overall appeal. In conclusion, the home exhibits a smooth blend of advanced technology and high-end finishes, promising a luxurious living experience! $3,600,000 Active

182 N Phelps Avenue Winter Park, Florida

4 Beds 5 Baths 4,812 SqFt 0.34 Acres

Welcome to 1391 Richmond Road, a true work of art and a surreal living experience now on the market. The most discerning buyer will fall in love with the optimal location, an unusually private lot right in the heart of Winter Park, a short stroll to Park Avenue along the stunning shores of Lake Virginia. This handcrafted Georgian style home, designed to emulate New York City townhouse living was masterfully crafted on a magical lot abundant with pristine natural vegetation. Enjoy the Florida lifestyle with frontage on Howell Creek…kayak or paddleboard amongst incredible wildlife to the Winter Park Chain of Lakes. As you arrive, you are greeted by an enticing mix of traditional and old Florida plantings, highlighted by Bevolo exterior lighting and gas lanterns leading the way to your custom mahogany/iron work front entry door. The grand foyer with soaring ceilings, stunning black and white marble flooring, and grand staircase which was built in place, with hand molded railing providing a welcoming signature. Flanked by separate formal living and dining areas on either side, the formal dining room features custom hand painted Gracie brand wallpaper and leads to the butler’s pantry with wine refrigerator. The gourmet kitchen boasts Busby cabinetry, new six burner Decor gas range, new Bosch dishwasher, Subzero refrigerator, large island with prep sink, built-in oven, and naturally lit breakfast area overlooking the backyard oasis. The kitchen opens to the spacious family room with extensive venetian painted millwork, gas/wood burning fireplace with custom Italian made marble surround, 11’4” ceilings, and French doors leading to the terrace and backyard retreat. The formal living room complete with venetian plaster, gas fireplace with custom marble is connected to the family room with a stunning barreled ceiling hallway conveniently located to a chic powder bath. The main floor also includes a full pool bath with access to one of the two garages with air conditioned work room, and a 2nd back staircase. The upstairs primary suite is a sanctuary, graced with an antiqued mirror entry, gas fireplace, double French doors leading to the serene balcony overlooking the statement backyard, and two custom closets with vast cabinetry and lighting. The spa-like bath features Walker Zanger flooring, generous walk-in shower, soaking tub and dual vanities with make-up area. Two additional ensuite bedrooms are also upstairs along with an office/flex room, full bath and laundry room. The second detached garage features a bonus room/convenient home gym. No expense was spared when building which displays antique and unique lighting fixtures, custom millwork, surround sound, central vacuum, reverse osmosis water filtration, and extensive storage throughout. Notable window treatments from the finest textile manufacturers worldwide (Clarence House, Elitis, Nancy Corzine, Carragio), wallcoverings (Fornasetti, Gracie, Schalamandre), lighting (Aerin, Niermann Weeks). This bespoke home is an entertainer’s dream with multiple outdoor areas to relax amongst the secret garden of terraced landscaping and four thoughtfully placed fountains. Celebrate nature’s wildlife which range from owls, great white egrets, blue herons, hawks, bunnies, and otters in your private sanctuary minutes to Winter Park’s premier dining, upscale shopping, Mead Botanical Garden, and the highly coveted Audubon K-8, and Winter Park High! $3,499,500 Active

1391 Richmond Road Winter Park, Florida

4 Beds 6 Baths 4,635 SqFt 0.45 Acres

Under Construction. Stunning architectural masterpiece built by LUIH homes nestled in the heart of prestigious Winter Park. This brand-new construction embodies the perfect fusion of contemporary design, timeless elegance, and exceptional quality offering 4 bedrooms, 4 full bathrooms, 2 half bathrooms, and over 4,200 square feet of thoughtfully designed luxury living space. As you step through the grand custom glass door, you're greeted by soaring ceilings, sleek wood flooring, and an abundance of natural light streaming through oversized windows and glass doors. Every detail has been curated to perfection from the artisan millwork and designer lighting to the open floor plan that seamlessly blends indoor and outdoor living. At the heart of the home lies a state-of-the-art kitchen designed to impress, featuring top-of-the-line Thermador appliances, a gas range, an oversized quartz waterfall island, custom cabinetry, and a walk-in pantry, it’s truly a culinary enthusiasts dream. Adjacent is a formal dining space with views of the stunning backyard space, perfect for entertaining. The expansive primary suite provides a serene retreat with its opulent en-suite bathroom featuring dual vanities, a spacious walk-in shower, a freestanding tub, and a huge walk-in closet. This home features three additional bedrooms each meticulously designed with their own en-suite bathrooms. Step outside to your own private backyard oasis featuring a sparkling pool and spa, a specious backyard, and a large, covered patio, perfect for al fresco dining. Jump on your golf cart and within minutes you’re transported to Park Ave, with its amazing shops, fine dining, and everything else that Winter Park features. Schedule your private showing today and experience the epitome of luxury Winter Park living. $3,490,000 Active

1910 Glencoe Road Winter Park, Florida

4 Beds 6 Baths 4,205 SqFt 0.25 Acres

Located in Winter Park’s highly sought-after “Golden Triangle,” 940 Lincoln Circle is a beautifully renovated West Indies/Key West-style home offering character, comfortable elegance, and functionality on an oversized .31-acre lot. This 4-bedroom, 4.5-bathroom residence spans 3,551 square feet and lives primarily as a one-story home, with a private upstairs suite that includes a bedroom, full bath, and bonus room—accessible both from within the home and via an alternate outdoor entrance. Perfect for multigenerational living, guests, or live-in assistance, the layout offers rare versatility in one of Winter Park’s most desirable neighborhoods. The gated front porch leads to a welcoming covered entry and soft foyer, opening into a spacious formal living room with vaulted wood-paneled ceilings and a gas fireplace. This space flows seamlessly into the dining area and kitchen, which overlook the screened porch and backyard oasis. The kitchen is appointed with marble countertops, custom cabinetry, gas cooktop, built-in cabinet-paneled Sub-Zero refrigerator/freezer, double ovens, and a walk-in pantry. A custom wine room, ideal for entertaining, sits just off the main living space. Nearby is a den or optional bedroom with closet, paired with a bright enclosed Florida room currently used as a home office with garden views. This wing connects to a full bath and a secondary bedroom at the front of the home. A stylish powder bath is tucked away for guests. The private primary suite is positioned at the rear of the property and features double custom closets, outdoor access, and a luxurious bathroom with dual vanities, large glass-enclosed shower, soaking tub, and private water closet. Upstairs, a second guest suite includes a bedroom, bathroom, and bonus/flex room, perfect for guests, a gym, or studio—accessible from inside the home or a private porch entry. At the back of the home, a spacious family room with fireplace opens to the screened lanai, offering ideal indoor-outdoor flow. The backyard features a fully fenced, landscaped retreat with a renovated saltwater pool and new equipment, surrounded by mature trees, hardscape patios, and garden paths. The summer kitchen includes a Blaze grill, Fire Magic refrigerator, Blackstone griddle, stainless sink, storage cabinetry, and vent hood—creating a resort-style space. The oversized two-car side-entry garage offers epoxy flooring, built-in storage, and room for larger vehicles. Additional upgrades include two Rinnai tankless water heaters, 2024 Trane condenser, 2019 Mitsubishi mini-split, full-house Generac generator with automatic transfer switch, and motorized shades by The Shade Store. The laundry room includes built-in cabinetry, a utility sink, and convenient side yard access. Thoughtfully designed and meticulously maintained, this turnkey home blends architectural charm with modern comfort—just a short walk from Park Avenue. $3,350,000 Active

940 Lincoln Circle Winter Park, Florida

4 Beds 5 Baths 3,551 SqFt 0.33 Acres

Nestled in peaceful Winter Park, your new contemporary home boasts expansive open living areas featuring 12-foot ceilings, five en-suite bedrooms, and outdoor living spaces spanning two levels. The semi-circular driveway and landscaped courtyard lead you to the front entry, adorned with frosted-glass double doors.  Inside, the sweeping view of the spacious open living, dining, and kitchen spaces will leave a lasting impression. A fireplace, built-in floor-to-ceiling bookshelves, and sliding glass doors punctuate the bright living room, which enjoys both east and west exposure. The adjoining dining area, equipped with a built-in buffet, elegantly accommodates intimate dinners and large sit-down gatherings. The gourmet chef's kitchen features a waterfall-edge marble-topped center island and Thermador® appliances, including separate refrigerator and freezer towers, a dishwasher, a wine refrigerator, and a natural gas range with a pot filler above. Marble countertops, tile backsplashes, Legrand Adorne® under-cabinet outlets and lighting accent the wood cabinets.  Whether used as a coffee and tea station, a smoothie bar, or for preparing cocktails, the inset wet bar, with its sparkling window-pane mirrored wall, provides a defined and refined space for beverage preparation. Crowning the secluded owner's retreat is a barrel-vaulted ceiling and sliding glass doors that offer relaxing views of the fountains in the swimming pool and spa. Unwind and rejuvenate in your spacious 6' free-standing bathtub, or indulge in the luxurious Italian-style shower in the en-suite bathroom. The extensive dual-sink wood vanity and the generous 10' by 11' walk-in closet ensure ample space for your personal care accoutrements, clothing, and accessories. The first floor also includes another full guest suite (currently used as an office), a laundry room, a mudroom, and a half bathroom. Upstairs, the central vaulted-ceiling family room is flanked by a large balcony overlooking the pool area below. Additionally, there are three more complete suites and a second-level laundry room. The private backyard oasis offers an expansive undercover lanai incorporating a summer kitchen with a natural gas grill, a passthrough bar to the interior dining room, and ample room for dining and lounging. When desired, remotely controlled screen panels can shield the space from balmy-weather insects. The salt-water swimming pool features a beach shelf with two in-water chaise-longues and a fountain jet. The inset spa also doubles as a fountain when not in use. An outdoor shower is also available. Additional elements include an oversized two-car garage and two natural gas tankless water heaters. Imagine this home with all these amenities is just minutes from downtown Winter Park, Park Avenue, Rollins College, Baldwin Park, and Advent Health, and it is in the Winter Park Schools zone. It is, indeed.  You can make this home your new reality! $3,295,000 Active

532 Worthington Drive Winter Park, Florida

5 Beds 6 Baths 3,974 SqFt 0.26 Acres

Introducing a stunning brand-new custom home by Butler Ridge Development, located in the highly desirable Park Grove neighborhood—strolling distance to Winter Park’s famed Park Avenue. This home offers timeless elegance, modern luxury, and walkable access to top-tier dining, shopping, and culture. From the inviting circular drive and professionally designed landscaping by Joe Knight, including a signature front palm that sets the tone for this elegant Florida property, every exterior detail makes a statement. Step through the inviting entry into an airy and sun-drenched interior featuring soaring ceilings, wide-plank white oak floors, oversized picture windows, and beautiful crown molding throughout. Inside, a sophisticated office with custom built-ins welcomes you, alongside a thoughtfully designed guest suite with a luxurious bathroom with roll-in shower, soft white finishes, and a custom walk-in closet—ideal for extended family or visitors.   The heart of the home is a soaring great room with 14'8" ceilings, a sleek fireplace, and a full wall of sliding glass doors overlooking the resort-style backyard. Entertain with ease in the open-concept living, dining, and chef’s kitchen—complete with a dramatic waterfall island, premium Thermador appliances (including four freezer drawers and diamond ice), dual-fuel range ovens with 6-burner gas cooktop, a 3rd oven + convection microwave, and expansive custom pantry. Adjacent mudroom and decorative laundry room. The first-floor primary suite is a tranquil retreat, featuring pool access, spa bath with soaking tub, separate shower with multiple sprayers, dual vanities, and a spacious custom walk-in closet. Upstairs, a loft-style bonus room complements the smart split-plan layout with 3 additional bedroom suites, walk-ins, and ample storage. Enjoy the best of Florida living in the beautifully landscaped backyard. Designed for both relaxation and entertaining, the outdoor living space includes a saltwater pool with elegant fountain feature, marble pavers, summer kitchen with built-in grill, sink, and beverage fridge, an outdoor bathroom, and ample grassy area for play or pets. 3-Car garage. Located within the highly desirable Dommerich Elementary, Maitland Middle, and Winter Park High School zones, and just minutes from downtown Winter Park, this home offers walkability, elegance, and convenience—wrapped into one exceptional property. $3,288,000 Active

731 Williams Drive Winter Park, Florida

5 Beds 6 Baths 4,260 SqFt 0.31 Acres

Under contract-accepting backup offers. One of Winter Park’s iconic and cherished homes, just a short distance from Park Avenue. On one of the most picturesque, brick-lined streets in downtown Winter Park, this extraordinary residence is a rare opportunity to own a piece of the city’s rich architectural history, fully reimagined with modern elegance and thoughtful design. On the same city block as the Alfond Inn and a two-block stroll to the world-renowned Park Avenue, this home offers not only luxurious living but an unparalleled lifestyle in one of Central Florida’s sought-after communities. Park Avenue is the heartbeat of Winter Park, a tree-lined promenade brimming with charm, home to award-winning restaurants, boutique shopping, art galleries and cultural landmarks. Residents and visitors alike are drawn to its timeless ambiance, where the rhythm of the day flows from morning coffee at a corner café to evening dinners under twinkling lights. Whether enjoying “Movies in the Park,” seasonal art festivals, the lively Winter Park Farmers’ Market or beloved holiday parades, living here means having a front-row seat to all of Winter Park’s treasured traditions. Originally built in the 1930s, this five-bedroom, 5.5-bath home has been meticulously renovated in recent years to preserve its historic character while seamlessly incorporating every modern convenience. From the moment you enter, you’re greeted by gleaming hardwood floors, classic architectural details and a warm, inviting atmosphere. The gracious living room centers around a charming fireplace, flanked by two sets of French doors that lead to a cozy sunroom, ideal for morning coffee or afternoon reading. A formal dining room provides an elegant setting for entertaining, while the open-concept kitchen and family room encompass a blend of functionality and style. The kitchen is a showpiece, featuring a large 15-foot Soma quartz island and countertops and marble backsplash, handcrafted cabinetry, top-of-the-line Wolf and Sub-Zero appliances, and a custom wet bar with under-counter wine refrigerator. It’s a space designed for gatherings, large or small. The expansive and private primary suite is on the main level and features a walk-in closet with custom built-ins and a luxurious en-suite bath with dual sinks and a marble/glass shower. Upstairs, you’ll find three additional bedroom suites, including one that could easily serve as a second primary suite, complete with French doors leading to a covered balcony. Each bedroom offers its own en-suite bath, hardwood floors and thoughtfully designed closet space with built-ins. A spacious first-floor laundry room offers ample storage, while the detached two-car garage includes a beautifully renovated first-floor guest cottage. Complete with a kitchenette, full bath, and cedar-lined walk-in closet, it’s the ideal space for guests, a home office or extended family. Surrounded by lush landscaping and a charming circular driveway, this home radiates curb appeal and classic Winter Park style. Whether you're walking to Park Avenue for dinner, enjoying a leisurely afternoon in Central Park, or simply soaking in the historic beauty of your neighborhood, this home places you at the center of it all. This is more than just a home, it’s a lifestyle and a rare chance to own one of Winter Park’s rare downtown area treasured properties. $3,250,000 Pending

266 Chase Avenue Winter Park, Florida

5 Beds 6 Baths 4,088 SqFt 0.31 Acres

Under Construction. Welcome to this exquisite 5-bedroom, 5.5-bathroom home built by Lundev, perfectly situated in the highly sought-after Timberlane Shores neighborhood of Winter Park. Spanning 4,080 square feet, this property offers the ultimate blend of luxury and comfort. Thoughtfully designed for both entertaining and everyday living, this home features high-end finishes and top-quality craftsmanship throughout. Upon entering, you're greeted by a charming front porch with a cozy fireplace, setting the tone for the warmth and elegance that continues inside. This inviting outdoor space is perfect for relaxing with a morning coffee or enjoying cool evenings with friends and family. Step inside to find a spacious great room, ideal for gathering and entertaining, boasting ample natural light and a seamless flow to the rest of the home’s main living areas. The gourmet kitchen is a chef’s dream, boasting high-quality appliances, a wine cooler, refrigerator drawers, and a casual café area for everyday dining. The adjacent formal dining room offers a sophisticated space for hosting elegant dinner parties and holiday gatherings. These thoughtfully designed spaces ensure that every meal and event is special. The luxurious primary suite is conveniently located on the first floor, providing a tranquil retreat with easy access. It features a spa-like bathroom with double sinks, a soaking tub, a shower, a linen closet, and a large walk-in wardrobe for ample storage. Additionally, on the main floor you will also find a detached bedroom or office with an en-suite bathroom, built-in closet, and private entrance offering flexibility and making it ideal for guests or as a private workspace. Upstairs, you’ll find three aditional bedrooms, each featuring its own en-suite bathroom and walk-in closet, providing comfort and privacy for all occupants. A versatile loft/den area on the second floor adds extra living space, perfect for a home office, playroom, or relaxation area, catering to various lifestyle needs. The outdoor area is an entertainer's paradise, complete with a private pool & spa, a cabana with a pleasant fireplace, and a summer kitchen for alfresco dining and entertaining. Whether hosting a barbecue or enjoying a quiet afternoon by the pool, this space is designed for relaxation and enjoyment. With its great location, this home offers excellent proximity to Blue Jacket Park, Baldwin Park, and the vibrant Park Avenue, known for its entertainment options, shops, and restaurants. Experience luxury living in one of Winter Park's most coveted areas. Schedule your private tour today to see this stunning property in person! $3,249,000 Active

1730 Winchester Drive Winter Park, Florida

5 Beds 6 Baths 4,080 SqFt 0.28 Acres

Welcome to a rare opportunity to embrace the Winter Park lakefront lifestyle in this custom-built masterpiece that blends timeless architecture with relaxed coastal sophistication. Crafted by Hanson Custom Homes and thoughtfully curated by Kate Voss Interiors, this modern coastal residence offers the perfect setting for those who value both refined living and a vibrant, connected lifestyle. With top-rated Winter Park schools, endless parks, bike paths, and the shopping, dining and events at Park Avenue and Baldwin Park just minutes away, the owners of this home spared no expense in creating a unique blend of luxury and livability in one of Central Florida’s most desirable communities. Step inside to soaring 14-foot ceilings, custom millwork, and a 20-foot Euro glass wall that disappears into a hidden pocket—blurring the line between indoors and out and filling the home with lake breezes and natural light. Whether you're hosting birthday parties by the lake, poolside barbecues, or just soaking in the serenity of a morning coffee on the water, this home was built to bring people together. The open-concept kitchen features exotic quartzite counters, a touchless faucet, Thermador appliances, and a full butler’s pantry and flows seamlessly into an expansive outdoor living space with motorized screens, a full summer kitchen, and views that stretch across your private beach and dock. Just steps from the pool, the lake becomes your playground—ideal for paddleboarding, fishing, or sunset cruises on your boat or jet ski. The primary suite comes complete with water views, motorized drapery, and spa-worthy bath finishes—including a steam shower, soaking tub, and private porch access. The main living areas are built for both entertaining guests and cozy family nights in, while the resort-style pool and spa deliver year-round fun with dual heat sources, LED lighting, and coral stone decking. Upstairs, every bedroom features lake views, walk-in closets, and smart layouts that offer both privacy and togetherness. The bright, central loft is perfect as a media room, homework space, or game lounge, keeping the family connected without sacrificing space. Energy-efficient spray foam insulation, an EV-ready oversized 3-car garage, smart-home integration, impact-rated glass, and commercial-grade soundproofing are just a few of the features that make everyday living seamless and secure. This one-of-a-kind property is ideally positioned with easy access to both Winter Park’s iconic charm and Baldwin Park’s family-friendly amenities—a true gem that offers the rare combination of newer construction, world-class craftsmanship, and a lifestyle built for generations to enjoy. There’s simply nothing else like this on the market. If you’ve been waiting for a newly built custom lakefront home that combines relaxed luxury with the best of Winter Park family living—this is the one. Call today to schedule your private showing. $3,200,000 Active

1891 Lake Spier Drive Winter Park, Florida

5 Beds 4 Baths 3,932 SqFt 0.79 Acres

Set on a sprawling half-acre, surrounded by meticulously manicured landscaping, this custom-built traditional estate exemplifies refined luxury, modern convenience, and an unparalleled lifestyle. The red brick façade, covered porches with glass doors, and gated side porte-cochere set a timeless tone, while two-story fluted columns add stately elegance. Inside, classic architectural details merge with modern design, highlighted by two-story coffered ceilings, intricate millwork, and expansive windows and French doors that flood the home with natural light. Thoughtfully designed for both entertaining and everyday living, the gourmet kitchen includes a 6-burner Viking gas cooktop, double dishwashers and sinks, a paneled refrigerator and separate full-sized freezer, a walk-in pantry, and an oversized island with breakfast bar seating. The first floor features a private primary retreat, two powder rooms, a workstation/mudroom accessible off the porte-cochere, and one of two laundry rooms. Upstairs offers three spacious bedroom suites with walk-in closets, a versatile bonus room, and a second laundry room. Embrace the Florida lifestyle from a two-story covered brick patio with a built-in gas grill, overlooking the private, fenced-in backyard oasis and breathtaking saltwater pool and heated spa, all elevated by a three-tier fountain and fire pit area, and wrapped in lush landscaping; this outdoor space is truly magical and not easily replicated in Winter Park! A circular driveway provides ample parking, while a gated side drive leads to an oversized, detached three-car garage with a bonus room above—ideal for a gym or studio. This particularly grand, wide street in the City of Winter Park is something truly special. Ideally located near Baldwin Park, Corrine Drive, and Park Avenue, and zoned for highly regarded Audubon K-8, this estate is more than a home—it’s a statement in timeless elegance. *Ask for a list of improvements, the floorplan and click on the virtual tour! $3,195,000 Active

1911 Stonehurst Road Winter Park, Florida

4 Beds 6 Baths 5,097 SqFt 0.5 Acres

Exquisite, Luxury Listing in the Heart of Winter Park! Stunning, single-story residence, customized and remodeled by Phil Kean Design Group. Open and spacious, 2,600 + SF interior layout which boasts 4 bedrooms, 3 full baths, a home office, living/dining spaces, a chef’s kitchen, and more. Throughout the home are beautiful hardwood floors, beam and coffered ceilings, plantation shutters, French doors, oversized picture windows, and designer accents. The gourmet kitchen features a large island with bar top seating, stone counters, marble tile backsplash, stainless steel appliances, WOLF gas range, SUBZERO refrigerator, dual drawer dishwasher, and walk-in pantry. French doors off the kitchen and living room open to seamlessly blend indoor and outdoor living, leading to a covered lanai that overlooks the meticulously landscaped backyard which includes a relaxing 8-jet spa, trellis garden, grill area, and turf greenspace. The home’s floorplan offers a desirable split-bedroom layout. The primary bedroom has a generously sized en suite with dual sinks, walk-in shower, and walk-in closet with built-in dressers. Each of the other 3 guest rooms are comfortably sized and feature ample closet space. Located just a short drive, walk, or bike ride from Park Avenue, this impeccable home is close to both Interlachen Country Club, the Winter Park Racquet Club, nearby shops and dining, Advent Health, and is zoned for the A-rated Lakemont/Maitland/WPHS school district. $3,195,000 Active

1020 Mayfield Avenue Winter Park, Florida

4 Beds 3 Baths 2,663 SqFt 0.26 Acres

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