Homes for Sale Between $1,500,000 to $2,000,000 in Winter Park, FL

4 Beds ⋅ 4 Baths ⋅ Tantum Add SubDv. ⋅ 32789 Zip Code

Truly a rare Winter Park offering. Perfectly positioned along the dogleg of the fourth fairway of the historic Winter Park 9-Hole Golf Course, this beautifully renovated four-bedroom, four-bath Mediterranean residence seamlessly blends timeless architectural character with sophisticated modern living. Rich in charm and thoughtfully updated throughout, the home welcomes you with an elegant living room featuring a gas fireplace, classic built-in shelving and abundant natural light. At the heart of the home is a stunning chef's kitchen, complete with custom floor-to-ceiling cabinetry, premium Thermador appliances, a charming breakfast nook and an inviting bar with wine refrigeration that flows effortlessly into the formal dining room, ideal for entertaining. A distinguished first-floor office offers an exceptional work-from-home environment, showcasing a breathtaking custom wall of built-in shelving, cabinetry and an integrated desk. This versatile space also serves beautifully as a library or den. Upstairs, all four bedrooms provide privacy and comfort. The luxurious primary suite features two separate closets, a spacious spa-inspired bath with a soaking tub overlooking the golf course and a private covered balcony perfect for enjoying peaceful morning coffee or evening sunsets. A generously sized secondary suite offers exceptional flexibility with its own custom walk-in closet, en suite bath and private rear staircase, making it ideal for guests, multigenerational living or a secluded retreat. Two additional bedrooms and a well-appointed full bath complete the second level. Updated features include smart house lighting, cabinet and shelving accent lighting, custom built-ins and much more. Designed to embrace Florida's indoor-outdoor lifestyle, the home offers a screened porch accessible from both the dining room and breakfast nook, creating an inviting space for year-round entertaining. Two additional open patios provide the perfect setting to relax while enjoying picturesque golf course views and the tranquil surroundings. Perhaps the home's greatest luxury is its exceptional location. Just steps from the boutiques, acclaimed restaurants, sidewalk cafés and vibrant atmosphere of Park Avenue, this residence offers an unmatched Winter Park lifestyle. Convenient access to downtown Orlando, major hospitals, world-renowned attractions and both Orlando International and Orlando Executive airports makes everyday living as effortless as it is elegant. This is a rare opportunity to own a beautifully updated Mediterranean home in one of Winter Park's most coveted and locations.

922 N Pennsylvania Avenue, Winter Park

$1,950,000

32792 Zip Code

Rare opportunity to acquire an established church property on 6.21 acres with outstanding frontage and visibility along one of the area's busiest corridors. The existing sanctuary, ample parking, and expansive grounds provide an excellent opportunity for a growing congregation to establish or expand its ministry. For investors and developers, the property's Future Land Use designation for multifamily offers exceptional long-term redevelopment potential in a high-demand location. A unique offering with immediate functionality and future possibilities.

3075 N Goldenrod Road, Winter Park

$1,899,000

5 Beds ⋅ 5 Baths ⋅ The Enclave Winter Park SubDv. ⋅ 32792 Zip Code

Pre-Construction. To be built. The Enclave is a premier, boutique community in the heart of Winter Park, featuring just 23 thoughtfully designed residences nestled beneath mature oak canopies being built by FG Schaub Custom Homes. A short walk to Phelps Park, YMCA, dinner and shopping. Surrounded by natural beauty and designed with intention, The Enclave offers a rare opportunity to enjoy a private, residential setting while remaining connected to the area’s finest dining, shopping, and cultural amenities just minutes away in downtown Winter Park.. With a limited collection of custom homes, this community delivers an elevated lifestyle defined by architecture, walkability, and enduring charm. This custom single-family home is thoughtfully designed with exceptional craftsmanship and upscale finishes throughout. Each residence features high-performance, low-E double-pane windows, 8-foot solid core interior doors, and tankless gas water heaters for modern efficiency and comfort. Homes are appointed with premium Wolf and Sub-Zero appliances, designer-selected finishes, and a curated palette of colors and materials. These homes have it all; summer kitchens well equipped with fridge and grill and a sparkling pool. Spacious layouts, refined detailing, and quality construction create an elevated yet livable environment, all set within a beautifully landscaped and private setting. There is still time for the Buyer to personalize design selections and explore certain home plan modifications. Upgrade options are also available, including the opportunity to add a detached cabana and/or guest house, subject to builder pricing, lot compatibility, and community guidelines. Please inquire for additional details and available customization options. Renderings are for inspirational purposes.

910 Enclave Place, Winter Park

$1,895,000

3 Beds ⋅ 4 Baths ⋅ Pennsylvania Place Rep SubDv. ⋅ 32789 Zip Code

Located just steps to the Golf Course and Park Avenue, in downtown Winter Park, 622 Penn Place is in the highly sought after Penn Place neighborhood. One of the few homes fronting the park with beautiful views from upper and lower porches, balconies and windows. This home provides the perfect balance of quiet privacy and convenient access to everything. The heart of the home features white kitchen cabinets, New stainless steel appliances and gas cooktop, overlooking eat-in breakfast nook and family room with gas fireplace & three sets of French doors opening to a bird and butterfly paradise with a huge covered, porch. There is also a dedicated office with built-in's and wet bar. The upstairs can be reached by both Elevator or elegant staircase and houses the owner’s suite with private balcony. It includes a large bathroom with dual sinks + makeup vanity, tub & separate shower, and oversized custom closet. Two additional bedrooms split from the master, as well as upstairs laundry room. Custom built by Maroon Fine Homes and beautifully updated and maintained, the high quality details and finishes can be felt throughout - features include high ceilings, crown molding, plantation shutters, and hardwood floors throughout. New Roof, New interior/exterior paint, acp tankless gas water heater and three covered patios. Fenced/Gated yard with four zone sprinkler system, paver driveway and attached 2 car garage with back alley entry. With its unparalleled location and custom details, 622 Penn Place is a rare opportunity to own in walking distance to downtown. Don’t miss your chance to make this exceptional property your next home!

622 Penn Place, Winter Park

$1,895,000

2 Beds ⋅ 2 Baths ⋅ Whispering Waters/Phillips Circle Rep SubDv. ⋅ 32789 Zip Code

Enjoy the Winter Park lifestyle in this beautifully renovated 2-bedroom, 2-bath lakefront condo offering 2,304 square feet in the heart of downtown Winter Park. Located on the second floor of Building 1, this light-filled residence was extensively remodeled in 2023 with an open floor plan and raised ceiling heights that give the home an airy, comfortable feel throughout. The spacious living room and kitchen take full advantage of the breathtaking views of Lake Osceola, while two fireplaces—one in the living room and another in the primary bedroom—add warmth and character to the space. The kitchen has been updated with white cabinetry, stainless steel appliances, double ovens, induction cooktop, tile backsplash, center island, and wine/beverage refrigerator. Formal living and dining spaces offer plenty of room for entertaining, and the oversized entertainment room off the primary bedroom features a closet and separate entry, making it a great option for a third bedroom, media room, or home office. The primary suite offers a walk-in closet and en-suite bathroom with a shower and dual sinks. The secondary bedroom includes two closets along with a separate alcove ideal for a reading nook or office space. A Florida room, currently used as a storage room, features brick flooring. Other highlights include plantation shutters throughout, beautiful exposed beams, additional storage closet in the garage, and two designated parking spaces in the covered garage. Residents enjoy a community pool, gated underground parking with elevator access, and an unbeatable location just steps from Park Avenue’s shops, restaurants, museums, and seasonal events. A rare opportunity to enjoy spacious lakefront living in one of Winter Park’s most desirable communities.

311 E Morse Boulevard Unit 1-3, Winter Park

$1,895,000

5 Beds ⋅ 5 Baths ⋅ The Enclave Winter Park SubDv. ⋅ 32792 Zip Code

Pre-Construction. To be built. 914 Enclave Place is a beautiful Alys Beach inspired design. The Enclave is a premier, boutique community in the heart of Winter Park, featuring just 23 thoughtfully designed residences nestled beneath mature oak canopies, being built by FG Schaub Custom Homes. A short walk to Phelps Park, YMCA, dinner and shopping. Surrounded by natural beauty and designed with intention, The Enclave offers a rare opportunity to enjoy a private, residential setting while remaining connected to the area’s finest dining, shopping, and cultural amenities just minutes away in downtown Winter Park.. With a limited collection of custom homes, this community delivers an elevated lifestyle defined by architecture, walkability, and enduring charm. This custom single-family home is thoughtfully designed with exceptional craftsmanship and upscale finishes throughout. Each residence features high-performance, low-E double-pane windows, 8-foot solid core interior doors, and tankless gas water heaters for modern efficiency and comfort. Homes are appointed with premium Wolf and Sub-Zero appliances, designer-selected finishes, and a curated palette of colors and materials. These homes have it all; summer kitchens well equipped with fridge and grill and a sparkling pool. Spacious layouts, refined detailing, and quality construction create a elevated yet livable environment, all set within a beautifully landscaped and private setting. There is still time for the Buyer to personalize design selections and explore certain home plan modifications. Upgrade options are also available, including the opportunity to add a detached cabana and/or guest house, subject to builder pricing, lot compatibility, and community guidelines. Please inquire for additional details and available customization options.

914 Enclave Place, Winter Park

$1,888,888

5 Beds ⋅ 4 Baths ⋅ Kenilworth Shores Sec 03 SubDv. ⋅ 32792 Zip Code

A PRIVATE RESORT-STYLE SANCTUARY IN THE HEART OF WINTER PARK 5 Bedrooms | 4 Bathrooms | 3,400+ SF|Saltwater Pool & Spa|Minutes to Park Avenue Welcome to a rare offering where luxury, tranquility, and architectural sophistication converge. Nestled in one of Winter Park's most desirable neighborhoods, just minutes from the boutiques, fine dining, and cultural attractions of Park Avenue, this custom Mid-Century Modern residence delivers an extraordinary lifestyle defined by elegance, wellness, and privacy. The home is within the acclaimed Winter Park school district, less than four miles from Trinity Preparatory School, and minutes from Rollins College and the University of Central Florida, placing premier educational opportunities nearby. Thoughtfully designed with a Zen-inspired aesthetic, the home blends clean architectural lines with warm natural elements to create a refined, restorative living experience. From the moment you arrive, a sense of calm surrounds you, offering a peaceful escape while remaining minutes from everything Winter Park offers. Inside, soaring 10-foot ceilings, expansive walls of glass, and wide-plank engineered hardwood flooring create bright, open living spaces filled with natural light. A semi-floating steel staircase with solid white oak treads serves as a dramatic focal point, while designer Restoration Hardware lighting adds warmth and sophistication throughout. The main living area was designed for entertaining. A Dimplex fireplace anchors the great room, complemented by a custom wine bar. At the heart of the home, the chef's kitchen showcases a waterfall island, premium quartz countertops, marble backsplash, double-stacked cabinetry, and a custom pantry. High-end Samsung smart appliances, including a Family Hub refrigerator, WiFi-enabled convection wall oven, Flex Duo cooking system, and 36-inch Bluetooth cooktop, complete this exceptional culinary space. A first-floor guest suite and full bath provide flexibility for visitors, a private executive office, fitness studio, or wellness retreat. The finished two-car garage features epoxy flooring and a modern glass garage door. Upstairs, the primary suite serves as a private sanctuary. The spa-inspired bath features a freestanding soaking tub, dual-entry marble shower with a semi-frameless glass enclosure, dual vanities, and a custom walk-in closet. Beyond the walls of the home lies your own private paradise. Professionally designed by Exotic Landscape Company, the resort-style outdoor living space evokes the serenity of a Balinese retreat. The newly constructed saltwater pool and spa showcase glass tile finishes, mini-pebble surfaces, travertine coping, LED lighting, therapy jets, a cascading waterfall, and smartphone-controlled OmniLogic automation. A custom outdoor stone shower, yoga platform, lush tropical landscaping, and curated hardscapes create an environment dedicated to relaxation and wellness. Additional features include Eufy smart lock technology, Arlo video doorbell, Google Nest thermostat, WiFi-enabled irrigation, smart garage controls, Quality Edge Vesta steel plank siding, and an expanded driveway. Less than ten minutes from Park Avenue, this exceptional residence offers a rare opportunity to own a home that feels more like a private luxury resort. More than a home, it is a sanctuary where timeless design, resort-inspired living, and one of Central Florida's finest educational settings create an unparalleled lifestyle.

2032 Kimbrace Place, Winter Park

$1,850,000

4 Beds ⋅ 4 Baths ⋅ Villa View Park SubDv. ⋅ 32789 Zip Code

Ideally on a quiet residential street just near Park Avenue, this custom-built transitional residence offers the best of Winter Park living, accessible, refined and thoughtfully designed from the ground up. Built in 2018 by Carlos Posada, the home delivers 2,653 square feet of living space across two floors, with an additional 365 square feet walk-up attic, four bedrooms and four full baths. From the moment you enter, the home makes an impression. French clay tile flooring anchors the defined foyer, opening into an expansive great room where Bolivian rosewood built-ins frame a gas fireplace and oversized windows draw the eye toward the pool and lanai beyond. The living, dining and kitchen spaces connect seamlessly, designed for everyday ease and effortless entertaining. The kitchen is equipped for the serious home cook, anchored by a full Thermador appliance package and thoughtfully appointed beyond the expected. The large island integrates a sink, microwave drawer, ice maker and refrigeration drawers alongside generous seating, while a walk-in pantry, concealed outlets and a warming drawer round out a workspace as purposeful as it is refined. Outdoor living is equally deliberate. A covered lanai with fireplace and space for a mounted television flows to an open-air terrace and dedicated grilling area, all overlooking a linear pool with water feature and professionally designed landscaping with evening lighting. Upstairs, the primary suite is positioned at rear of the home for added privacy, with abundant natural light, a generous walk-in closet and an en-suite bath. Two additional bedrooms each offer their en-suite baths and built-in closets. A well-appointed laundry room, along with a linen closet and dedicated storage closet in the hall, complete the second floor. On the main level, a fourth bedroom is finished as a library with custom white oak built-ins and French doors opening to the exterior of the home, offering flexible living or professional workspace. Throughout, Panaget engineered hardwood flooring, decorative crown molding, Sierra Pacific windows and doors, cast stone accents, and integrated stair lighting reflect the home's elevated attention to detail. Additional highlights include a detached two-car garage, extensive storage throughout and an infrastructure designed for future elevator conversion. A rare opportunity to own a newer custom home in one of Winter Park's accessible and beloved neighborhoods.

721 Pansy Avenue, Winter Park

$1,849,900

3 Beds ⋅ 4 Baths ⋅ Winter Park Residential SubDv. ⋅ 32789 Zip Code

Discover luxury living in this exquisitely renovated two-story condominium, ideally situated on the third floor of the highly sought-after Douglas Grand in the heart of Winter Park. This elegant three-bedroom, three-and-one-half-bath residence seamlessly blends sophisticated design with everyday comfort. Immediately captivating, the light-filled open floor plan showcases stunning new wide-plank white oak flooring, high ceilings, detailed crown molding, and all-new designer lighting throughout. The chef’s kitchen is a showpiece, featuring crisp white cabinetry, luxurious white quartz countertops, a spacious breakfast bar island, elegant gold hardware, and a built-in desk. A charming breakfast nook offers the perfect setting for morning coffee or casual dining. French doors open to a private enclosed atrium, creating a versatile outdoor retreat ideal for alfresco dining, relaxing, or entertaining guests in style. The expansive living and dining spaces flow effortlessly, while a private first-floor bedroom with en suite bath and walkout balcony provides an ideal space for guests, multigenerational living, or a home office. Upstairs, the primary suite serves as a peaceful sanctuary, complete with an indulgent soaking tub, dual vanities, an oversized walk-in closet, and French doors leading to a large private balcony with sweeping views of Winter Park's iconic Park Avenue—perfect for enjoying sunrise coffee or evening sunsets. A second upstairs en suite bedroom offers its own private bath and generous walk-in closet. Thoughtful features include an upstairs laundry room, a spacious storage closet with potential elevator conversion for future accessibility, and a secure gated garage with two reserved parking spaces. Perfectly positioned in the heart of Winter Park, Douglas Grand places you just steps from Park Avenue, the Winter Park Farmers’ Market, Rollins College, Hannibal Square, Winter Park Golf Course, the Winter Park Tennis Center, Winter Park Village, and an array of renowned dining, shopping, and cultural attractions. Enjoy an unparalleled walkable lifestyle in one of Central Florida's most desirable communities. Notable improvements include an interior renovation (2026), front elevation windows and French doors (2024), interior paint (2024), and HVAC system (2022).

101 S New York Avenue Unit 311, Winter Park

$1,800,000

5 Beds ⋅ 5 Baths ⋅ Osceola Shores Sec 02 SubDv. ⋅ 32789 Zip Code

Short Sale. Welcome to this luxury, home in the heart of Winter Park. Less than a mile away from Park Ave. Winter Park that offers entertainment, restaurants, farmers market and so much more. A beautiful contemporary style home with modern interior finishes. Featuring an open floor plan, 5 bedrooms, 4.5 baths, a loft/flex space, media room, 2 study areas, front porch, back patio, lanai and so much more. Corner lot and privacy. Engineered hard wood floors through out the house and tile in utility rooms. 2 laundry rooms for convenience, located on 1st and 2nd floor of the home. Private backyard setting, a very large pool, an outdoor entertainment area featuring a kitchen and a fireplace and a screened in lanai. Metal Roof with Solar panels. A gas stove with large island and lots of space for entertainment. This home has a lot to offer in the most desirable location. Schedule your showing today.

281 Brewer Avenue, Winter Park

$1,800,000

4 Beds ⋅ 4 Baths ⋅ Horton Aaron SubDv. ⋅ 32789 Zip Code

Built by Clarkson Concepts and ideally located in the heart of Winter Park just moments from Park Avenue, this sophisticated modern residence blends luxury design, smart-home innovation, and effortless indoor-outdoor living across three thoughtfully designed levels. From the moment you arrive, the striking foyer makes a memorable first impression with its bold geometric detailing, designer finishes, and contemporary ambiance that immediately sets the tone for the home. Beyond the entry, the main living spaces unfold into an open-concept kitchen, dining, and living area designed for both everyday comfort and elevated entertaining. The chef’s kitchen is beautifully appointed with custom cabinetry, a Wolf stove, Bosch dishwasher, a premium side-by-side True Residential refrigerator and wine column combination, and a separate under-island beverage refrigerator designed for effortless entertaining. Expansive PGT sliding doors connect the interior spaces seamlessly to the lanai and outdoor retreat, while the Klipsch 5.1 surround sound system, electric fireplace, Anderson windows, ceiling fans, and integrated Elon smart-home system enhance the experience throughout the home. The outdoor living area was designed as a private modern zen-inspired escape, featuring a fully air-conditioned and heated lanai with cedar-lined ceilings, rolled screens, and direct access to the serene backyard retreat complete with a four-person sauna. Thoughtfully integrated technology and upgrades include Jellyfish lighting, Nest cameras, power-over-Ethernet shades, leak protection system, water filtration systems including Aqua Sauna Water Filter and Kohler Connect Water Minder, as well as two separate AC units serving each floor independently. The first floor also offers a private guest suite, ideal for visitors or multigenerational living. Upstairs, the second level features a spacious laundry room, two additional en-suite bedrooms, and an impressive primary suite designed as a true retreat. The luxurious primary bathroom showcases a standing shower with digital water controls, dual sinks with custom storage cabinetry, and an expansive custom walk-in closet. Additional highlights throughout the home include engineered wood flooring, electric blinds, and refined designer details at every turn. Crowning the residence is a spacious third-floor bonus area offering endless flexibility for a media room, fitness studio, office, or additional lounge space, all fully air-conditioned for year-round comfort. Combining exceptional craftsmanship, advanced smart-home functionality, and an unbeatable Winter Park location with exceptional proximity to both Park Avenue and Winter Park Village, this extraordinary residence places premier dining, boutique shopping, cafés, entertainment, and everyday conveniences just moments from home while delivering a truly elevated lifestyle experience.

723 Symonds Avenue, Winter Park

$1,799,999

5 Beds ⋅ 5 Baths ⋅ Pervis Survey For R E SubDv. ⋅ 32792 Zip Code

Private, gated lakefront living on Bear Gully Lake one of Winter Park’s most desirable spring-fed ski lakes. Set on an expansive 137-acre body of water, this custom residence offers a rare combination of privacy, scale, and true Florida waterfront lifestyle. A circular driveway behind a private gate welcomes you to a thoughtfully renovated home designed to capture sweeping lake views. Bear Gully Lake is spring-fed and open to water vehicles, making it ideal for boating, water skiing, wakeboarding, tubing, fishing, and year-round enjoyment. The lakefront experience is exceptional, featuring a fully equipped dock with power, covered boat lift, and sun deck, perfectly positioned for enjoying stunning sunsets. Outdoor living is a highlight of the property. The expansive lanai and pool area overlook the lake and are ideal for entertaining, complete with a renovated summer kitchen featuring a grill, sink, mini refrigerator, and granite countertops. The oversized backyard provides ample space for gatherings, recreation, and pets. Inside, the home opens to a dramatic great room with vaulted ceilings, a striking stacked-stone feature wall with custom built-ins, and large sliding glass doors that fully retract to create seamless indoor-outdoor living. The space was reimagined during extensive renovations to maximize natural light and lake views. The chef’s kitchen, redesigned by award-winning designer Sandra Agurto of CCI, features all-wood cabinetry, quartz countertops, contemporary backsplash, oversized island with beverage and wine refrigerators, induction cooktop, convection ovens, and a separate full refrigerator and freezer, with abundant custom storage throughout. The primary suite is privately located in its own wing and offers serene lake views, high ceilings, and a spa-style en-suite bath renovated in 2022 with soaking tub, walk-in shower, expansive custom vanity, upgraded lighting, and private water closet with bidet. A large walk-in closet with custom built-ins completes the suite. All bedrooms feature their own bathrooms and walk-in closets, providing exceptional privacy and flexibility, with three full en-suite bedrooms ideal for guests or multigenerational living. Additional flexible spaces include a gym or bonus room suitable for formal living, dining, or a game room. Recent upgrades include a new roof (2018), new hot water heater (2024), fully fenced yard, Russound sound system, updated security system, new pool deck pavers, and a rebuilt dock with Trex decking and updated boat lift components. The home is part of a lake association with no mandatory dues, providing community updates and seasonal events such as the holiday boat parade. Conveniently located near SR-417, UCF, downtown Winter Park, and Trinity Prep, this is a rare opportunity to own a true spring-fed lakefront home on one of Winter Park’s most coveted lakes.

4469 Old Bear Run, Winter Park

Homes for Sale in Winter Park, FL Between $1,500,000 to $2,000,000

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