4 Beds ⋅ 2 Baths ⋅ Georgetown Estates SubDv. ⋅ 32792 Zip Code

Welcome to this beautifully remodeled, move-in-ready home in the highly sought-after Winter Park area. This single-story residence features 4 bedrooms and 2 bathrooms, offering a bright, open floor plan with modern finishes designed for both comfort and functionality. A standout feature of this property is its commitment to sustainable living and energy efficiency. Highlights include: - Newer Roof: Installed in 2023 - Radiant Barrier & Blown-In Attic Insulation: Keeps the Florida heat out and significantly lowers cooling costs. - High-Efficiency HVAC: Energy Star rated AC unit ensuring consistent temperatures and peak savings. Step outside to an expansive backyard featuring a private pool, perfect for relaxing or entertaining. This large outdoor space offers endless possibilities for customization, such as a garden or an outdoor kitchen. Located in a quiet, established neighborhood within an A+ rated school zone, this home provides convenient access to top shopping, dining, parks, and major highways. Don't miss this incredible opportunity to own a fully updated turnkey property in one of the most desirable areas of Winter Park.

501 Heritage Boulevard, Winter Park

$1,199,000

3 Beds ⋅ 3 Baths ⋅ Osceola Heights SubDv. ⋅ 32789 Zip Code

This new residence, thoughtfully designed by Michael Wenrich, captures the timeless elegance and refined simplicity reminiscent of the iconic coastal architecture of Alys Beach. Clean architectural lines, graceful curves, and abundant natural light combine to create a home that feels sophisticated and inviting. Inside, gorgeous chevron-patterned wood floors flow throughout the main living areas, setting a warm and elegant tone. The open-concept floor plan is designed for everyday living and effortless entertaining, with expansive windows allowing natural sunlight to pour into every space. At the heart of the home is a beautifully designed kitchen that blends classic style with modern functionality. A stunning quartz waterfall island anchors the space, complemented by custom cabinetry and a suite of high-end appliances including an ILVE induction range with six elements and Café French door refrigerator, dishwasher and microwave. Designer-grade lighting and refined finishes elevate the kitchen into a centerpiece of the home. The dining room is filled with light and character, featuring three sets of French doors that open to a charming private front and side courtyard, an ideal setting for morning coffee or intimate outdoor dining. In the living room, a dramatic wall of sliding glass doors connects the interior to the brick patio and backyard, creating a seamless indoor-outdoor lifestyle. The first-floor primary suite offers a peaceful retreat, complete with a spacious walk-in closet and a spa-inspired bath featuring a large glass-enclosed shower, separate soaking tub and dual vanities. Additional conveniences on the main level include a beautifully appointed powder bath, a dedicated laundry room and a generous storage room tucked neatly beneath the staircase. Upstairs, a versatile loft provides additional living space ideal for a media area, office or lounge. Two additional bedrooms are also on the second floor, each featuring custom built-in closets, beautiful designer lighting and abundant natural light. Built with quality and efficiency in mind, the home includes numerous upgrades such as a slate roof, Trane air-conditioning system, Rheem tankless water heater and a two-car attached garage. Ideally just minutes from the renowned shopping and dining of Park Avenue and charm of downtown Winter Park, this exceptional home also offers convenient access to major roadways, Orlando International Airport, leading hospitals, and top-rated public and private schools, bringing together style, comfort and location in one remarkable new construction opportunity.

1870 Walker Avenue, Winter Park

$918,000

4 Beds ⋅ 3 Baths ⋅ Karolina On Killarney SubDv. ⋅ 32789 Zip Code

Pre-Construction. To be built. This is your final opportunity to build a custom home in one of Winter Park’s most sought-after pockets. Set on a 6,748 sq ft lot, this brand-new 4-bedroom, 3.5-bath residence offers 2,662 sq ft of thoughtfully designed living space, blending clean modern architecture with the comfort and functionality today’s buyers expect. Crisp lines, open-concept living, and intentional design create a home that feels both elevated and livable. What makes this opportunity truly unique: this is the last remaining homesite within a curated collection of three custom builds—each thoughtfully designed with its own architectural identity, yet unified in creating a refined, cohesive streetscape. The other two homes are already underway, making this your only chance to secure a position in this limited offering. Located just 6 minutes from Park Avenue, you’re moments from Winter Park’s best—boutique shopping, award-winning dining, and everyday conveniences—while also being close to top-rated hospitals and major thoroughfares. Offered as a custom build, this home allows you to tailor finishes, selections, and details to match your vision. Pricing reflects the base build, with upgrade options available to create a fully personalized end product. With new construction opportunities in 32789 at this price point becoming increasingly scarce, offerings like this are few and far between—especially with the ability to fully customize your home from the ground up.

Lot #21 Karolina Ave, Winter Park

$3,275,000

4 Beds ⋅ 6 Baths ⋅ Ellno Willo SubDv. ⋅ 32789 Zip Code

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

1581 Forest Avenue, Winter Park

$430,000

4 Beds ⋅ 2 Baths ⋅ Winter Park Estates SubDv. ⋅ 32792 Zip Code

Updated 4-bedroom, 2-bath home in a premium Winter Park location with NO HOA and a spacious backyard. This home is currently in the final phase of renovation and has already undergone major upgrades, including remodeled bathrooms, updated kitchen, new flooring, upgraded electrical, new AC System and a newer roof. The interior has been thoughtfully modernized, offering a bright open layout ideal for comfortable living and entertaining. The property is being sold in its current condition; exterior improvements will not be completed, giving the future owner the opportunity to finish and customize the exterior to their preference. Conveniently located near shopping, dining, schools, and major roadways.

Winter Park

$574,900

3 Beds ⋅ 2 Baths ⋅ Metzingers Add SubDv. ⋅ 32789 Zip Code

Virtually Staged. Fabulous location in Winter Park! Completely remodeled from top to bottom this stunning home blends modern design with everyday comfort in a highly desirable Winter Park location. Thoughtfully updated with stylish and contemporary finishes throughout this home offers a bright and open feel that’s perfect for today’s lifestyle. The beautifully renovated interior features a modern kitchen, quartz countertops, soft-close shaker cabinets overlooking the dining room & family room. The updated bathrooms and fresh finishes throughout create a move-in ready home that feels brand new! The spacious layout flows seamlessly into the outdoor living area where you’ll find a large fenced-in backyard with a pavered patio and a cozy fireplace perfect for entertaining, relaxing or enjoying Florida evenings. Located just minutes from shopping, dining, parks, and top Winter Park amenities this property is an excellent opportunity for first-time homebuyers or investors looking for a turnkey home in a prime location. A rare opportunity to own a fully updated home with modern style and a spacious backyard in the heart of Winter Park!

1354 Indiana Avenue, Winter Park

$1,649,000

5 Beds ⋅ 4 Baths ⋅ Parklando #3 SubDv. ⋅ 32789 Zip Code

PRICED BELOW APPRAISAL, CUSTOM BAREFOOT BROTHERS HOME IN WINTER PARK. Finding a truly CUSTOM-BUILT home in Winter Park is rare. Finding one built this recently—with this level of craftsmanship, infrastructure, and thoughtful design—is even rarer. Built by Barefoot Brothers in 2014 and thoughtfully designed for an active family that values entertaining, work-from-home flexibility, and elevated everyday living, this exceptional 5-bedroom, 3.5-bath residence (currently configured as 4 bedrooms + dedicated office) offers a level of quality that simply cannot be replicated at this price point. Just minutes from Park Avenue, Audubon Park, dining, shopping, and top Winter Park amenities, the location is as compelling as the home itself. This residence delivers the rare combination of TIMELESS ARCHITECTURE + MODERN CONSTRUCTION. Built using INSULATED CONCRETE FORM (ICF) CONSTRUCTION, the home offers exceptional durability, energy efficiency, and a remarkably quiet interior—creating a true retreat from outside noise and Florida heat. Average summer utility bills are approximately $185/month. The exterior was freshly repainted in 2023, further enhancing the home’s curb appeal and long-term maintenance appeal. The floor plan was intentionally designed for real life. The FIRST-FLOOR PRIMARY SUITE serves as a private retreat with an attached office, custom walk-in closet with hidden under-stair storage, and a spa-like bath featuring dual sinks, marble vanity, freestanding cast iron soaking tub, marble floors, and an oversized walk-in shower with dual shower heads. A separate downstairs office easily functions as a fifth bedroom if desired. At the center of the home, the chef’s kitchen was built to perform as beautifully as it looks with MARBLE COUNTERTOPS, WALNUT ISLAND, GE CAFÉ GAS RANGE, BOSCH DISHWASHER, BRAND-NEW SAMSUNG REFRIGERATOR, and an oversized walk-in pantry/butler’s pantry. The adjacent living room is equally impressive with extensive custom built-ins, gas fireplace, library shelving, surround sound wiring, and French doors opening seamlessly to outdoor entertaining spaces. Designed with entertaining in mind, the outdoor spaces feel like an extension of the home with a spacious river rock patio, covered breezeway with tongue-and-groove ceiling, natural gas hookup for grilling, detached rear-entry two-car garage, circular front drive, and additional rear parking—an uncommon luxury in this highly sought-after location. Upstairs, soaring ceilings frame a large bonus/playroom alongside three additional bedrooms and two baths, including a Jack-and-Jill layout. A climate-controlled attic space under AC offers valuable bonus storage not included in the home’s stated square footage. Additional upgrades include NATURAL GAS (range, fireplace, dryer & grill), TANKLESS WATER HEATERS, CAT 6 ETHERNET WIRING, QUANTUM FIBER READINESS, and LOW-E DOUBLE PANE WINDOWS. Every inch of this home was intentionally designed with longevity, comfort, and function in mind. Try building this level of fully custom home in Winter Park today—on this timeline, with these finishes, this infrastructure, and this location—at this price point. It’s nearly impossible. Homes of this caliber rarely become available, especially PRICED BELOW APPRAISAL. Schedule your private showing and experience firsthand what makes this Winter Park home so exceptional.

2501 Winter Park Road, Winter Park

$614,500

3 Beds ⋅ 2 Baths ⋅ Winter Park Pines Rep SubDv. ⋅ 32792 Zip Code

Welcome to 2708 Lion Heart Rd, where timeless charm meets modern elegance in the heart of Winter Park. This beautifully reimagined home has been thoughtfully renovated from top to bottom, offering a seamless blend of style, comfort, and functionality. Step inside to discover brand-new luxury vinyl plank flooring flowing throughout, creating a warm and cohesive feel in every room. The stunning two-tone kitchen is a true centerpiece, featuring sleek quartz countertops, contemporary finishes, and new appliances to be installed at closing—perfect for both everyday living and entertaining. The upgrades continue in the fully renovated bathrooms, where carefully selected color palettes and high-quality finishes provide a fresh, sophisticated look designed to stand the test of time. Every detail of this home has been meticulously considered, leaving no space untouched. Outdoors, enjoy your private oasis with a newly resurfaced pool—ideal for relaxing weekends or hosting gatherings year-round in Florida’s sunshine. This move-in-ready gem offers the perfect opportunity to own a like-new home in a highly desirable location. Come experience the beauty, quality, and lifestyle that 2708 Lion Heart Rd has to offer—your dream home awaits.

2708 Lion Heart Road, Winter Park

$6,900,000

6 Beds ⋅ 7 Baths ⋅ J Kronenberger Sub SubDv. ⋅ 32789 Zip Code

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.

1260 Alabama Drive, Winter Park

$820,000

5 Beds ⋅ 3 Baths ⋅ Lake Bell Terrace SubDv. ⋅ 32789 Zip Code

*Ask about a lender provided credit up to $12,500 on this home!*1927 Eland Avenue is a rare single family home for sale in Winter Park FL 32789, located on a quiet dead end street with no rear neighbors. This Winter Park home features a main residence plus a detached in law suite ADU built in 2022, offering exceptional flexibility for multi generational living, guest accommodations, or rental income potential. The main home offers three bedrooms and two bathrooms with real wood floors, Spanish Colonial architectural details, abundant natural light, and a functional open living layout. The primary bedroom and bathroom offer the opportunity to be expanded, allowing a future owner to customize and enhance the suite to their needs. Interior features include a wood beamed dining room, fireplace, and a built in bar with mini fridge, making this home ideal for entertaining and everyday living. Major updates include a 2015 roof, 2018 windows, and a 2022 HVAC system, providing added peace of mind for buyers seeking an updated home in Winter Park Florida. The detached in law suite cottage includes two bedrooms and one bathroom, along with a modern eat in kitchen featuring white cabinetry, butcher block countertops, and contemporary finishes. The guest house also offers its own laundry area and skylights that enhance the bright, open feel. A private brick paver patio creates a separate outdoor living space exclusively for the ADU. This ADU has the ability to be separately metered from the main house and can have its own independent address if desired. The main home’s outdoor living area includes an outdoor kitchen, brick paver patio, and a private backyard designed for relaxing and gatherings. Conveniently located near Lee Road, State Road 17-92, and Interstate 4, this property provides easy access to Winter Park, Maitland, College Park, and downtown Orlando. Buyers searching for a Winter Park home near Park Avenue, Rollins College, Winter Park Village, Trader Joe’s, SunRail, and the Winter Park Farmers Market will appreciate the central location and walkable lifestyle. This is a rare opportunity to own a versatile single family home with an in law suite ADU in one of the most desirable neighborhoods in Winter Park FL.

1927 Eland Avenue, Winter Park

$7,250,000

5 Beds ⋅ 6 Baths ⋅ Robert Dhu Macdonald Park SubDv. ⋅ 32789 Zip Code

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.

40 Palmer Avenue, Winter Park

$860,000

4 Beds ⋅ 2 Baths ⋅ 32792 Zip Code

Rare opportunity to own an established daycare operating from two structures on the same parcel, offered together with the real estate. The business currently provides immediate income for a hands-on owner or family-run operation. One structure is currently utilized for daycare operations, while the second structure is a single-family home that offers excellent potential for future daycare expansion (subject to licensing and approvals)—a unique value-add opportunity for growing operators. The property is already configured for childcare use with existing operations in place, making this an ideal turn-key opportunity for families looking to step into business ownership or operators seeking to expand their footprint. Sale includes real estate. Business goodwill, licensing, and operations may be included or negotiated separately. Convenient location with strong demand for childcare services. Please do not disturb staff or business operations. Showings by appointment only.

1521 Heron Wood Place, Winter Park

Recently Sold Listings in Winter Park, FL

All Sold Homes for Sale in Winter Park, FL

The Nest Group

Search

Resources

About