Luxury Homes for Sale in
Winter Park, Florida

Winter Park is a historic, upscale city just north of downtown Orlando, known for brick streets, the shops and cafes of Park Avenue, Rollins College, and its scenic chain of lakes. Its real estate spans historic estates, lakefront homes, and luxury new builds.

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Luxury Winter Park Properties

Explore homes across Winter Park, from historic Park Avenue estates to lakefront residences.

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Search homes for sale in Winter Park, from Park Avenue to the Winter Park chain of lakes.

Oscar Rodriguez
& Daniela Ledo

Oscar and Daniela’s mission is to serve Winter Park buyers and sellers with the highest ethical standards, guiding you with expertise and integrity from the first showing to closing day.

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Years Of Experience

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Sold Properties

Residential Listings in Winter Park

Under Construction. NEW CONSTRUCTION – Under Construction. Welcome to Winter Park! This stunning modern residence is meticulously designed and ideally located near everything. This beautifully crafted home features 4 bedrooms, 2.5 bathrooms, and 2,350 square feet of living space, plus an additional 1,247 square feet of terraces and lanai. The open-concept kitchen showcases quartz countertops, custom cabinetry, and stainless steel appliances, perfect for both everyday living and entertaining. Step outside to the private lanai, where you can enjoy a summer kitchen, pool, and lushly landscaped backyard, creating an ideal indoor-outdoor lifestyle. From the moment you enter, the home is filled with warm natural light and high-quality finishes throughout, creating a welcoming atmosphere. The primary bedroom is conveniently located on the first floor, offering privacy and comfort along with an inviting, functional layout. The second floor features three additional bedrooms, two bathrooms, and two expansive terraces, perfect for relaxation or entertaining. Located just minutes ( 1.25 Miles ) from Park Avenue Restaurants and shopping district, 15 min from Downtown Orlando, and an array of fine dining, boutique shopping, museums, and local cafés, this exceptional home offers modern luxury in an unbeatable location. $1,750,000 Active

1840 Anzle Avenue Winter Park, Florida

4 Beds 3 Baths 2,350 SqFt 0.15 Acres

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. $7,250,000 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

Stunning Custom Estate on the Shores of Lake Osceola $6,700,000 Pending

405 Lakewood Drive Winter Park, Florida

4 Beds 3 Baths 4,208 SqFt 1.21 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

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Winter Park Real Estate

B | LIVE helps buyers and sellers across Winter Park, from historic homes near Park Avenue to lakefront estates on the chain of lakes, with a deep understanding of this distinctive market.

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Park Avenue

Shops & dining

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College-town charm

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+23

Years Of Experience

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Listing your home in the MLS is not enough.

We make sure your Home is highlighted with those UNIQUE features each home has to offer. We want to impress potential buyers. In order to do so, we have an amazing team “behind the scenes” specialized in the latest trends in marketing online, a fantastic photographer that will take the best pictures, 3D Tours, Zillow Tours and a PERSONALIZED video that will show your home perfectly, specially to those out of state buyers.

All this amazing material we produce is used in the right platforms online with the best demographic strategy depending on the market flow in the moment you decide to list your home.

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What People Say About Us

+42 5-star Reviews

01 Testimonial

To say Daniela and Oscar are the BEST at what they do is an understatement! They are a dynamic duo!!!! They leave no stone unturned in helping guide you, stage for sale, from start to finish they will be at your side. They are the utmost professionals, know their market like no other(s), create fantastic videos and ..

Jose Cedeno

Windermere, FL

02 Testimonial

Oscar has been fantastic to work with. He has been diligent, responsive, proactive, honest and effective. He helped me rent my property over 8 years ago and when I told him I was ready to sell, he layed out a plan, we executed the plan, and the property was sold in less than 2 weeks. Full price

Dianne Russell

Orlando, FL

Winter Park Real Estate FAQ

Winter Park homes range from around $600,000 for bungalows and condos to well over $5 million for historic and lakefront estates.

Winter Park is known for its brick streets, Park Avenue shopping and dining, Rollins College, museums, and a scenic chain of lakes.

Yes. The Winter Park chain of lakes offers sought-after lakefront properties, many with docks and boat access.

Winter Park sits just north of downtown Orlando, only a short drive away, while keeping its own distinct, upscale character.

You will find historic estates, Mediterranean-style homes, bungalows, and luxury new construction throughout the city.

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Whether you are buying or selling in Winter Park, our team is here to guide you with a refined and personal real estate experience.

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