Homes For Sale in Winter Park 32789 - 190 homes

Remarks: $50,0000 Price Improvement on this amazing oversized lot! Located in one of Winter Park’s most desirable and picturesque neighborhoods, Timberlane Shores! This stunning five-bedroom residence has been recently renovated in an elegant, European style blending timeless character with modern luxury. Situated on over one-third of an acre, the property is accented by majestic oak trees and lush Florida-native landscaping that's creates a private and serene retreat where peacocks often roam freely through your yard. The heart of the home is the beautifully designed chef’s kitchen, featuring quartz countertops, a gas range with custom hood, double built-in convection ovens, stainless steel appliances, a wine refrigerator, and a well-appointed butler’s pantry—perfect for entertaining. The light-filled family room is open to the kitchen and showcases a wood-burning fireplace, custom built-ins, and an original brick accent wall that adds warmth and architectural charm. Engineered hardwood flooring and preserved original terrazzo floors run throughout the home, enhancing its quality designer choices but also an inviting feel. The flexible floor plan offers five spacious bedrooms, three full bathrooms, and two half baths, providing ample space for both everyday living and hosting guests. Expect to be impressed by the elegant owner's suite with a sizable walk-in closet and stunning ensuite bathroom featuring dual vanities, beautiful cabinetry with lots of storage and a generously sized soaking tub. Outdoor living is equally impressive, with a resort-style heated pool complete with a sun shelf, an outdoor kitchen with a built-in grill, sand volleyball court and a large deck featuring built-in seating and a fire pit—ideal for gatherings or relaxing evenings under the stars. Zoned for Winter Park’s top-rated schools, this exceptional home is just a five-minute drive to Park Avenue’s renowned shopping and dining, and walking distance to Baldwin Park’s vibrant downtown, offering shops, restaurants, and a Publix. This is a rare opportunity to own a thoughtfully renovated home in one of Winter Park’s most beautiful and sought-after settings. Experience the rare combination of European-inspired luxury, resort-style outdoor living, and an unparalleled Winter Park location. Be sure to watch the video tour and virtual property walkthrough in the attachments. Better yet, schedule a private showing today and discover a home that truly defines elevated Florida living.

Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)

Listing Agent: Farah Bloom (407-873-5222)

Remarks: Welcome to this beautifully updated Winter Park home, perfectly positioned on a desirable corner lot and zoned for Audubon Park K-8 and Winter Park High School. With 5 bedrooms and 3 full baths, this spacious residence offers the ideal blend of functionality and style for modern living. Step inside to an open, light filled floor plan featuring luxury vinyl floors and a cozy wood burning fireplace that anchors the main living space. The renovated kitchen is thoughtfully designed with both everyday living and entertaining in mind, flowing seamlessly into the dining and living areas. A dedicated office provides the perfect work from home setup or quiet retreat, while the flexible layout offers plenty of room for guests, growing families, or multi generational living. Outside, enjoy a private backyard with a charming fire pit and rock gathering are deal for relaxing evenings or hosting friends. The oversized lot also offers ample space to add a pool and create your own backyard oasis. Additional highlights include a 2-car garage, roof replaced in 2018, home repiped in 2019, and updated AC for peace of mind. This is a rare opportunity to own a move-in ready home in one of Winter Park’s most sought after neighborhoods, walking distance to the Audubon Park Garden District with amazing dining, and shopping.

Listing is courtesy of: NORDQUIST & COMPANY INC (407-694-0996)

Listing Agent: Elizabeth Nordquist (407-694-0996)

Remarks: Located in the heart of Winter Park, this beautifully appointed 3,048 sq. ft. residence with saltwater pool and spa offers an ideal blend of comfort, style, and functionality. Designed for both everyday living and entertaining, the home features an open and inviting floor plan filled with natural light and high-end finishes throughout. The gourmet kitchen is equipped with granite countertops, stainless steel appliances, gas range, center island with breakfast bar, and 42” cabinetry with crown molding, all overlooking the spacious family room with gas fireplace and French doors leading to the pool and outdoor living area. The first-floor primary suite offers private French door access to the pool, a generous walk-in closet, and a luxurious bath featuring dual vanities, jetted soaking tub, and a large walk-in shower. Upstairs you will find three additional bedrooms, a large bonus room (easily convertible to a fifth bedroom), two balconies, and a convenient wet bar, creating a perfect space for guests, family living, or entertainment. Additional interior highlights include travertine flooring on the main level, tray ceilings, solid wood doors, extensive crown molding, built-in closet shelving, updated lighting, and dual tankless energy-efficient gas water heaters. The private outdoor area is designed for Florida living with a heated saltwater pool and spa, outdoor shower, summer kitchen hookups, and spacious green yard ideal for relaxing or entertaining. This exceptional property offers a rare opportunity to enjoy luxury living in one of Winter Park’s most desirable locations.

Listing is courtesy of: PARK TOWN REAL ESTATE LLC (561-801-9199)

Listing Agent: David Auerbach (407-619-5250)

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

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)

Listing Agent: Prentice Williams (321-438-8955)

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

Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC (407-312-8003)

Listing Agent: Julie Christensen (407-592-2055)

Remarks: One or more photo(s) has been virtually staged. Set on a prized corner lot in Winter Parks sought after Orwin Manor Neighborhood, 1651 Westchester Ave is a timeless classic with Cape Cod inspired architecture that has been meticulously reimagined with today’s luxury finishes while preserving its original charm. Refinished Original Pine hardwood flooring and a beautifully updated fireplace welcome you into the main living space, while the showpiece kitchen delivers true chef-level design with new Custom European Cabinetry, Quartz Countertops with a Waterfall Island, Porcelain Tile floors, premium lighting, under counter Kitchen Aid Ice Maker and a top-tier appliance suite including Wolf Gas Range-top, Wolf Built-in Oven & Microwave and Bosch Refrigerator and Dishwasher. The primary suite is a serene retreat with a newly redesigned spa style bath with frameless walk-in shower, soaking tub, new double sink vanity and lighting—plus a walk-in closet with California Closet built-in’s and a versatile bonus room ideal for a sitting area, nursery, or dedicated laundry space. Outdoors, enjoy resort-style living under the expansive 26’ x 24’ covered Lanai featuring vaulted tongue-and-groove ceilings, tile flooring, a striking stone gas fireplace with RealFyre burners, stainless mantle, perfect for effortless entertaining. There is even enough room to customize the outdoor space with your own Pool Oasis. Recent improvements include a re-roof 2020, HVAC System, Double-Pane windows, 4-panel slider & front door, fresh interior/exterior paint, new custom shades, privacy bamboo landscaping, privacy fencing and an extended paver driveway. The attached Garage offers dedicated storage space and a bonus room with mini-split system which could offer space for home gym or office. Just minutes from Park Avenue’s acclaimed dining and shopping, top Winter Park amenities, Advent Health Medical Campus and quick access to key corridors for an easy downtown Orlando commute, this is 32789 living at its most refined—classic architecture, modern systems, and elevated indoor-outdoor lifestyle in one of Winter Park’s most sought-after neighborhoods.

Listing is courtesy of: SERHANT (786-296-8626)

Listing Agent: Shawn Layton (321-514-8055)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Enjoy the best of downtown Winter Park living in this spacious 1-bedroom, 2-bathroom condominium located in the highly sought-after Park West Condominiums. This well designed residence offers comfortable living with the rare convenience of two full bathrooms. Park West is a gated community known for its exceptional amenities, including a resort-style swimming pool, lighted tennis courts, and a clubhouse perfect for social gatherings and private events. Residents also benefit from secure entry, covered parking, and beautifully maintained grounds, creating a quiet and private residential setting just moments from the heart of the city. One of the community’s most desirable features is its unbeatable proximity to Park Avenue. Just a short walk away, you’ll find Winter Park’s premier destination for boutique shopping, award-winning restaurants, cafés, art galleries, Central Park, Rollins College, and the weekly farmers market. Whether you’re enjoying a casual coffee, fine dining, or cultural events, everything downtown Winter Park has to offer is right at your doorstep. This condominium combines location, convenience, and lifestyle amenities, making it an ideal opportunity for full-time residents or those seeking a low-maintenance home in one of Central Florida’s most prestigious neighborhoods.

Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)

Listing Agent: Kevin Mcclanahan (407-491-8509)

Remarks: Welcome to this beautifully updated Winter Park bungalow, just steps from Hannibal Square and Park Avenue! This charming 3-bedroom, 2-bath home offers just over 1,100 square feet of thoughtfully renovated living space. The kitchen has been tastefully renovated and upgraded with modern appliances, while tile flooring runs throughout the entire home. Major updates include newer roof, fully replumbed system (completed this month), and a brand-new water heater—giving you true peace of mind. Inside, you’ll love the high ceilings in the living, dining, and kitchen areas, creating a bright and open feel. Large windows flood the home with natural Florida sunlight, and the private rear deck is perfect for relaxing or entertaining. This is a true move-in-ready home in one of Winter Park’s most desirable locations—schedule your showing today before it’s gone!

Listing is courtesy of: CENTRAL FLORIDA PRIME REAL ESTATE LLC (407-404-4041)

Listing Agent: Jonathan Nakhnoukh (407-334-5806)

Remarks: Under Construction. Stunning Winter Park new build by Vimaro Homes in Park Grove.

Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC (407-312-8003)

Listing Agent: Christopher Christensen (407-312-8003)

Remarks: Under contract-accepting backup offers. Presenting an extraordinary southern traditional estate in the heart of the coveted Vias of Winter Park, a residence that effortlessly blends timeless architecture with exceptional craftsmanship. This stunning home, designed by acclaimed architect Gary Hancock, made its debut as the Southeast Builder’s Conference Showhouse for two consecutive years, a testament to its design and quality. From the moment you arrive, the home’s presence is both elegant and inviting. A circular drive leads to a charming porte-cochère and an extended driveway, culminating in a three-car garage. The façade is defined by classic columns, a welcoming second-floor balcony, and eleven glowing Bevolo gas lanterns from New Orleans, while nineteen matching electric lanterns illuminate the backyard, casting a warm, timeless ambiance across the property. Inside, every detail tells a story. Reclaimed Chinese Elm wood floors, rich with character and history, flow throughout the main living spaces, perfectly complemented by soaring ceilings adorned with striking wood beams. The kitchen is both a showpiece and a workspace, outfitted with premium Thermador appliances, including a six-burner range, steam oven, warming drawer and dual integrated refrigerators. Antique ceiling tiles form a distinctive backsplash, while custom cabinetry with replicated antique float glass adds a layer of understated sophistication. A hidden walk-in pantry enhances both form and function. The kitchen opens into a grand great room anchored by a fireplace and custom built-ins, creating an ideal setting for both everyday living and entertaining. Beyond, a versatile billiards room shares a dramatic two-sided fireplace and features a full wet bar, wine refrigeration, dishwasher and an adjacent full bath, perfectly suited as a pool bath. The dining room, framed by French doors, offers serene views of the covered lanai and lush backyard. The first-floor primary suite is a private retreat designed for comfort and convenience. A fireplace anchors the space, while thoughtful amenities include a private laundry room, custom walk-in closet and a well-appointed wet bar with leathered granite counters, a Thermador fridge and a dishwasher. The primary bath serves as the main spa-like experience, featuring a marble walk-in shower, a soaking tub, and dual vanities. A second, separate full bath within the suite provides additional functionality. Upstairs, accessible by a sweeping curved staircase or elevator, you’ll find three generously sized ensuite bedrooms and a bonus room complete with a wet bar and access to the rear covered balcony while two bedrooms have access to the front covered balcony, perfect for enjoying morning light or evening breezes. A third-floor retreat, currently used as a playroom, offers endless possibilities for a home office or studio. Outdoor living is equally compelling, with a large, covered lanai overlooking a resort-style pool and expansive backyard designed for relaxation and entertaining. Ideally just minutes from the boutiques and dining of Park Avenue and within walking or biking distance to the Winter Park Racquet Club, this exceptional home is set among the tree-lined streets and distinguished estates that define the Vias, one of Winter Park’s most sought-after neighborhoods. A rare offering where classic elegance, thoughtful design and modern livability come together beautifully.

Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)

Listing Agent: Mick Night (407-629-4446)

Remarks: Brand new construction luxury home in the heart of Winter Park! This stunning two-story custom residence offers nearly 3,000 sq ft of heated living space with 5 bedrooms and 4 1/2 bathrooms. A soaring two-story foyer creates a dramatic first impression and opens into an expansive great room featuring 12-foot ceilings, wide-plank flooring, and abundant natural light. The family room showcases a custom paneled feature wall with a sleek built-in electric fireplace, creating a striking focal point for the space. The gourmet kitchen is designed for both everyday living and entertaining, highlighted by a large center island with seating, European slab cabinetry, premium hardware, designer countertops, and high-end appliances. Ample storage and a clean modern aesthetic make this kitchen as functional as it is beautiful. Tucked beneath the staircase is a custom wine storage feature, adding a unique luxury detail. The first floor also includes a private guest suite with its own en suite bathroom, perfect for visitors or multi-generational living. A dedicated home office provides a quiet workspace, while the main-floor laundry room adds convenience. Outside, a professionally designed outdoor kitchen extends the living space and creates the perfect setting for year-round entertaining under the Florida sky. Upstairs, the luxurious primary suite serves as a private retreat. The spacious walk-in closet features a fully custom organization system, while the spa-inspired primary bathroom includes a dual-sink vanity, elegant freestanding soaking tub, and oversized walk-in shower with premium tile work. Three additional bedrooms complete the second floor. Two share a beautifully appointed Jack-and-Jill bathroom, while the fourth bedroom features its own private en suite bath, offering flexibility for guests or family members. Located at 240 N. Phelps Avenue, this home places you just minutes from Winter Park’s iconic Park Avenue — a vibrant destination known for its boutique shopping, award-winning restaurants, art galleries, and charming sidewalk cafés. Residents enjoy access to top-rated schools, including Winter Park High School, as well as renowned cultural destinations such as the Morse Museum of American Art and the Polasek Museum. Outdoor lovers will appreciate nearby Central Park, Mead Garden, and the scenic Winter Park Chain of Lakes. Conveniently located near I-4, SR-417, downtown Orlando, Lake Nona Medical City, UCF, and Orlando International Airport, this home offers the perfect balance of luxury, convenience, and the timeless charm that makes Winter Park one of Central Florida’s most sought-after communities. Schedule your private showing today.

Listing is courtesy of: GOLDEN GROUP REALTY LLC (407-990-5905)

Listing Agent: Milena Fernandes (407-990-5905)

Remarks: Totally traditional. This luxury single-story home is in the desirable Sevilla neighborhood in Winter Park. Sitting high and dry on approximately a half-acre, beautifully landscaped lot. Original home was mostly gutted down to the studs in 2011-2012 and completely re-done. Interior layout boasts formal living with bay window and tall ceilings, dining room with antiqued mirror set into extensive moldings and trim, plus a library/den with a tongue and groove wood vaulted ceiling and a wall of bookshelves and built-ins. The spacious family room with a white-washed brick, wood-burning fireplace wall and vaulted ceiling is all open to the breakfast area and kitchen. The gourmet kitchen features custom inset cabinet drawers and doors, white marble slab backsplashes, Kohler farmhouse sink and a large island with a deep prep sink. The kitchen is a chef’s delight with a 48-inch Viking gas range, Viking warming drawer, Jenn-Air refrigerator, wine refrigerator and a Bosch dishwasher. The kitchen also has amazing storage and two large pantries. There are a total of four bedrooms (two are in the in-law suite suite) and three full baths. Throughout the home are beautiful real ¾-inch-thick and 5-inch-wide plank walnut floors, beam and coffered ceilings, French doors, oversized picture windows and designer accents lighting. French doors off the family room open to seamlessly blend indoor and outdoor living, leading to a covered lanai with travertine stone tile overlooking a resort and entertaining backyard. Huge swimming pool and a 30-by-15-foot pergola with Bistro lighting, which is a wonderful spot to relax, dine and play, all on a tiny pebble surface, like an Italian driveway! French garden fountain, rose garden and synthetic turf for pets make the backyard a haven. The home’s floor plan offers a desirable layout with huge primary bedroom with a generously sized en-suite bath with dual sink counters, amazing Roman walk-in shower, jetted tub with bubblers and two large walk-in closets. Guest wing features a spacious bedroom and bath and the West Wing is a full In-law apartment, including a bedroom, handicapped bath, full kitchen and its living room (which would be easy to be converted back into the 4th bedroom - plans available). Imagine having a wonderful space for in-laws or an adult family member that needs space of their own. Just a short drive or bike ride from Park Avenue, this open and inviting home has easy access to Park Avenue, AdventHealth, downtown Orlando and is zoned for A-rated schools. Surround sound through most of the house and CAT 6 wiring throughout. Recent additional remodeling and updating have taken place including all new paint inside and out, as well as a new roof and gutters in 2023. A detailed list of all renovations is available upon request.

Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)

Listing Agent: Jan Walker (407-718-9644)

Remarks: Under contract-accepting backup offers. Under Construction. Renderings available soon. Brand-new custom construction on coveted Lakeview Avenue marries classic Winter Park charm with crisp, contemporary living. Behind its inviting façade you’ll find an airy two-story layout featuring four bedrooms and 4 ½ baths, including a full en-suite guest retreat on the main level. Three additional bedrooms share the upper floor with a bright loft that easily flexes as a playroom, office, or second lounge.The heart of the home is a chef-ready kitchen outfitted for serious cooking—double wall ovens, a dedicated cooktop, and generous countertop space—anchored by a spacious walk-in pantry and a convenient mudroom drop zone to keep daily life organized. Just beyond, a soaring great room centers on a built-in fireplace, while wide sliders open to a covered rear porch perfect for year-round alfresco dining. Upstairs, every bedroom enjoys direct or semi-private bath access, giving the residence the feel of four private suites, and a dedicated laundry room means no hauling baskets downstairs. Practical perks abound: an oversized two-car garage for gear and golf carts, impact-rated construction engineered to the latest Florida wind code, and full pre-wire rough-ins ready for your preferred appliance and lighting packages. All this sits minutes from Park Avenue’s dining and boutique shopping, Rollins College, and Winter Park’s famous chain of lakes. Schedule your private tour and discover the fresh, low-maintenance lifestyle waiting for you in one of Central Florida’s most sought-after neighborhoods. Final design and features subject to change.

Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE (407-647-1211)

Listing Agent: Marie Helen Ledbetter (407-286-4363)

Remarks: One or more photo(s) has been virtually staged. Limited-time incentive: Seller offering a $20,000 buyer credit for qualified buyers. Brand-New 2025 Mediterranean Luxury in Historic Winter Park. Introducing 1473 Berkshire Avenue — a just-completed luxury residence nestled on one of Winter Park’s most peaceful, tree-lined, and century-old streets. This two-story Mediterranean masterpiece delivers the perfect blend of timeless architecture and contemporary design, offering 5 bedrooms, 4 bathrooms, and nearly 2,900 sqft of refined living space. Step inside to discover: • 10-ft ceilings & 8-ft solid-core doors • Wide-plank luxury vinyl flooring throughout • Gourmet kitchen with quartz countertops, custom cabinetry, stainless steel appliances & oversized island • Elegant electric fireplace and expansive great room • Built-in wine cellar discreetly tucked under the stairs • Downstairs guest suite for added privacy Upstairs, the primary suite impresses with pool views and a spa-style bath: dual vanities, soaking tub, walk-in shower, and a generous closet. Three additional bedrooms include a Jack & Jill layout plus one with a private en-suite. A large upstairs laundry room adds convenience. Outside, your private backyard oasis awaits: • In-ground pool, fully landscaped • Summer kitchen with built-in grill • Covered patio for year-round entertaining Located just minutes from Park Avenue, this home offers walkability, top-rated schools, cultural landmarks, boutique shops, and dining. A rare opportunity to own new construction in one of Central Florida’s most iconic neighborhoods. Schedule your private tour today — this home defines the Winter Park lifestyle.

Listing is courtesy of: GOLDEN GROUP REALTY LLC (407-990-5905)

Listing Agent: Milena Fernandes (407-990-5905)

Remarks: In the sought-after Orwin Manor neighborhood, this beautifully updated one-story residence offers a seamless blend of comfort, style and convenience. Featuring three bedrooms and two baths, the home showcases an open-concept floor plan enhanced by engineered wood flooring that extends throughout every room, creating a cohesive and inviting living environment. The kitchen is thoughtfully updated with quartz countertops, refreshed cabinetry, newer appliances and a charming breakfast nook, ideal for casual dining. The living spaces flow effortlessly to a wonderful enclosed porch, providing additional year-round enjoyment, with direct access to an open brick-paver patio complete with a firepit, all set in a fully fenced backyard ideal for entertaining or relaxing in privacy. Both baths have been tastefully updated, and a new roof installed in 2021 that adds to the home’s overall appeal and peace of mind. Ideally just minutes from vibrant shopping and dining of downtown Winter Park and College Park, with convenient access to major roadways and the AdventHealth Orlando campus, this home offers exceptional accessibility to all metro Orlando has to offer. Whether as a primary residence or an investment opportunity, this property presents an exceptional offering in a prime, established location.

Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)

Listing Agent: Mick Night (407-629-4446)

Remarks: Under contract-accepting backup offers. Boasting a prestigious Park Avenue address, this striking modern architectural residence perfectly balances bold design with spa-like serenity. Set on a beautifully landscaped corner lot, the home embodies the rare combination of privacy and proximity, just a leisurely 25-minute stroll from Park Avenue’s world-class boutiques and dining. Every element of the design has been meticulously curated to evoke a sense of refined tranquility, where clean lines, natural textures, and warm tones create a timeless yet inviting atmosphere. Inside, expansive open concept living spaces are bathed in natural light, showcasing designer lighting, custom millwork, and seamless indoor-outdoor integration. The chef’s kitchen is a true centerpiece, anchored by dramatic quartz countertops, sleek custom cabinetry, and top-tier stainless steel appliances, complemented by a hidden walk-in pantry that enhances both style and function. The main living area opens effortlessly to the pool creating a fluid connection between indoor elegance and alfresco entertaining. The primary suite is a private retreat defined by calm sophistication offering a spa-inspired bath with a massive walk-in shower featuring multiple shower heads, a freestanding soaking tub, dual vanities, and a custom closet that feels like a boutique dressing room. Upstairs, a loft serves as a serene media or lounge area, while three spacious ensuite bedrooms provide comfort and privacy for family and guests. A dedicated home office continues the home’s minimalist aesthetic, fostering focus in a tranquil setting. Outdoors, the property unfolds into a private resort-like sanctuary with a sparkling pool, lush landscaping, and a fully equipped summer kitchen designed for seamless entertainment. A newly added rooftop deck serves as an architectural statement piece, connected by a spiral staircase that descends to the backyard below. The detached gym offers flexibility as a fitness studio, guest suite, game room, or creative workspace. From its sleek modern lines to its spa-like finishes, this home captures the essence of elevated Winter Park Living. A short walk to Winter Park Village and downtown WP puts you right in the middle of everything.

Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC (407-312-8003)

Listing Agent: Julie Christensen (407-592-2055)

Remarks: BRAND NEW CONSTRUCTION COMPLETED APRIL 2026, MOVE-IN READY. This 3,164 sqft home at 1523 Miller Ave, Winter Park, FL 32789 combines modern design, high-end finishes, and an unbeatable central location. Featuring 5 bedrooms, 4 full bathrooms, and a private salt-water pool, the home is designed for both everyday comfort and effortless entertaining. The open L-shaped living, kitchen, and dining area is filled with natural light and anchored by a 4-panel grand pocket slider that fully retracts, opening the entire living space to the covered patio for true indoor-outdoor living. The chef’s kitchen overlooks the main living area and flows seamlessly outside to a fully equipped outdoor kitchen with grill, sink, and fridge, complemented by a spacious seating area and pool—ideal for hosting year-round. Additional highlights include a shingle roof with metal accents, a pergola accenting the front of the garage, and clean architectural lines that elevate the curb appeal. The floor plan offers flexibility with generous bedroom sizes and well-appointed full baths, while the backyard retreat centers around the sparkling salt-water pool. Location is a major advantage—2 minutes to I-4, 4 minutes to Mills Avenue, 5 minutes to Park Avenue, 10 minutes to Downtown Orlando, and approximately 20 minutes to Disney, placing dining, shopping, nightlife, and major employers all within easy reach. A rare opportunity to own a brand-new construction home in one of Winter Park’s most connected neighborhoods.

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Eric Trumble Ii (407-592-8624)

Remarks: Under contract-accepting backup offers. Beauifully rennovated property on coveted brick street in PRIME Winter Park Location! This exceptional 3-bedroom, 3.5-bath home sits on a generously sized, fenced, private lot—perfect for entertaining or family living. Every inch of this residence has been thoughtfully updated, featuring 3-zone AC, updated plumbing, electrical, windows, foam insulation, and 2022 roof. Inside, luxurious designer touches abound. You're welcomed by an elegant foyer with Calacatta gold marble flooring and designer sphere lighting. The open-concept living space features rich eucalyptus flooring and soaring vaulted ceilings, seamlessly connecting to the outdoors through french doors that open to a bricked patio with tongue-and-groove wood ceiling, summer kitchen, and expansive yard. At the heart of the home is a gourmet kitchen that will delight any chef, complete with a Viking 6-burner natural gas range including griddle and double oven, an oversized entertaining island and a stylish wet bar with wine fridge. The thoughtfully designed floor plan includes two downstairs bedrooms, one makes a perfect home office, the other is a mother-in-law suite with a private entrance—ideal for guests or teens. Both secondary full bathrooms boast rainfall shower heads, dual flush toilets, and designer fixtures and tile. Upstairs, the expansive master suite offers vaulted ceilings, a custom walk-in closet, and french doors leading to a private balcony. The luxurious master bath features a 7-spray shower system, an aromatic Jacuzzi tub, and a ceiling-mounted waterfall spout for the ultimate spa-like experience. This home blends elegance, comfort, and functionality—an entertainer’s dream with a fantastic flow for everyday living!

Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)

Listing Agent: Olivia Maxwell (407-222-4440)

Remarks: Charming Winter Park Opportunity in Desirable Dubsdread Heights! NEW ROOF NEW A/c new kitchen ,bath, floor Welcome to 811 Overspin Drive, a cozy and character-filled 2-bedroom, 1-bath single-family home nestled in the heart of Winter Park. This property offers approximately 700+ square feet of living space on a generously sized lot, providing endless potential for homeowners, investors, or those looking to build their dream home in a prime location. Situated in the sought-after Dubsdread Heights neighborhood, this home is just minutes from downtown Winter Park, College Park, and Orlando’s vibrant dining, shopping, and entertainment districts. The property’s spacious lot offers room for expansion, renovation, or new construction, making it a rare opportunity in one of Central Florida’s most desirable zip codes. Whether you’re a first-time buyer, an investor seeking value-add potential, or someone looking to customize a home in a premium location, this property delivers both charm and opportunity. With strong surrounding home values and continued growth in the area, 811 Overspin Drive is an excellent chance to invest in the future of Winter Park living. Don’t miss your opportunity to own in one of Central Florida’s most sought-after communities!

Listing is courtesy of: RICK SINGH REAL ESTATE (407-383-3231)

Listing Agent: Rick Singh (407-383-3231)

Remarks: Welcome to your private slice of paradise, perfectly positioned on a charming brick-lined street in the heart of historic Winter Park. This custom-built estate exudes casual elegance from the moment you step through the grand double door entry, where soaring 12-foot ceilings, rich architectural details, and exceptional craftsmanship immediately set the tone. Thoughtfully designed with a well-balanced and highly functional floor plan, the home offers a seamless blend of formal and informal living spaces ideal for both everyday living and elevated entertaining. At the heart of the home, the pristine chef’s kitchen opens effortlessly to the family room and is outfitted with a built-in Thermador French door refrigerator, custom lighted cabinetry, granite countertops, a six-burner gas range with pot filler, double ovens with warming drawer, and an oversized island designed for gathering. A beautifully appointed butler’s pantry with wine fridge and wet bar creates the perfect transition to the formal dining space. Tucked away for privacy, a dedicated home office or library offers a quiet retreat for work or study. The first-floor primary suite is a true sanctuary, featuring intricate ceiling detail, expansive windows, and private French door access to the outdoor living space. The spa-inspired primary bath includes a jetted tub, dual vanities, and two oversized walk-in closets. Upstairs, three generously sized secondary bedrooms and two additional baths—including a private en suite—provide comfortable accommodations, while a charming Juliet balcony offers picturesque views of the tree-lined street below. Step outside to an exceptional outdoor living experience designed for year-round enjoyment. The covered lanai features a fully equipped summer kitchen with built-in grill, custom copper hood, and beverage fridge for the warmest Florida days. The saltwater pool creates a resort-style setting, surrounded by lush landscaping and enhanced by upgraded lighting and smart technology. This meticulously maintained home has been extensively upgraded, including new HVAC systems for both levels, on-demand water heater, whole-house surge protection, updated LED lighting with dimmer controls, smart home integrations for pool, irrigation, security, and climate, as well as complete interior and exterior repainting with premium finishes. High-end reclaimed maple and beech wood flooring has been installed and is complemented by refined architectural details such as curved archways, custom millwork, and elevated designer fixtures. Additional highlights include a newly created wine room, epoxy-coated garage flooring, central vacuum system, and enhanced exterior features with added awnings and detailed craftsmanship. Situated on a gorgeous lot with added privacy and with garage doors thoughtfully positioned away from the street, this home offers both presence and practicality. Just a short stroll to Lake Mizell and minutes from the renowned dining, shopping, and cultural experiences of Park Avenue, this exceptional property combines timeless design, modern upgrades, and an unbeatable location.

Listing is courtesy of: ORANGE SLICE PROPERTIES (863-632-9765)

Listing Agent: Liz Jones (407-619-6345)