Winter Park Single Family Homes For Sale - 218 homes

Remarks: 3 bedroom 3 bathroom pool home. Enjoy the large backyard. Schedule your showing today!

Listing is courtesy of: ALFA REAL ESTATE LLC (407-545-9562)

Listing Agent: Thai Nguyen (407-545-9562)

Remarks: Under contract-accepting backup offers. Amazing location near Park Ave! Completely reimagined and rebuilt from the studs, this exceptional one-story 3-bedroom, 2-bath residence offers the perfect blend of modern luxury and timeless charm in one of Winter Park’s most coveted locations—just a short stroll to the boutiques, dining, and cultural attractions of Park Avenue. Every inch of this home has been thoughtfully renovated in 2026 with no detail overlooked. Enjoy peace of mind with all-new electrical, plumbing, HVAC, windows, and garage door, ensuring efficiency and reliability for years to come. Roof 2021. A beautifully designed paver driveway enhances the home's curb appeal, creating a warm and welcoming first impression. Inside, the open and inviting floor plan is enhanced by premium tile flooring, designer finishes, and an abundance of natural light. The stunning, fully updated kitchen serves as the heart of the home, featuring sleek cabinetry, quartz counters, high-end finishes, and center island with bar seating. The kitchen flows seamlessly into the living and dining spaces—perfect for both everyday living and entertaining. Both bathrooms have been beautifully redesigned with modern fixtures and elegant touches. The spacious first floor primary suite offers a serene retreat with en-suite bath featuring a stunning walk in shower. Enjoy the convenience of the indoor laundry room with extra storage space. Step outside to the screened in back porch to enjoy the Florida lifestyle. Situated in a highly desirable Winter Park neighborhood, this turnkey home combines walkability, luxury upgrades, and an unbeatable location. A rare opportunity to own a like-new home just moments from the very best of Park Avenue living.

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

Listing Agent: Ingrid Livingston (407-595-5972)

Remarks: Under contract-accepting backup offers. Beautifully designed and impeccably maintained, this light-filled home offers the perfect blend of modern comfort and timeless style. Featuring an open and airy layout, the home is highlighted by abundant natural light, neutral designer finishes, and thoughtfully curated living spaces throughout. The bright and inviting living area flows seamlessly, creating the ideal space for both everyday living and effortless entertaining, while a spacious loft provides additional flexibility for a media room, lounge, or family retreat. The serene primary suite offers a true retreat-like atmosphere with soft neutral tones and abundant natural light, complemented by a well-appointed primary bath featuring dual vanities, expansive counter space, and a clean, modern design. The master bedroom is on the first floor. Additional bedrooms are upstairs, comfortable, and versatile, each filled with natural light and designed to accommodate guests, family, or personalized use. A charming flex space is also upstairs and offers endless possibilities as a playroom, creative studio, or additional living area. Secondary bathrooms are well-maintained with modern finishes and timeless appeal, enhancing both style and convenience throughout the home. Step outside to an expansive screened lanai that creates a private outdoor oasis, ideal for dining, lounging, or entertaining while enjoying tranquil views. An additional outdoor seating area further enhances the home’s indoor-outdoor lifestyle, offering the perfect setting for relaxing or gathering with guests. Move-in ready and thoughtfully styled, this home combines comfort, versatility, and elevated design in every detail, making it an exceptional opportunity for a wide range of buyers. The neighborhood also offers a plethora of amenities including a dog park, pool, clubhouse, gym, and walking trails. You are also in close proximity to dining, schools, and entertainment. Come see this home today!

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

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

Remarks: Under contract-accepting backup offers. Newly remodeled ranch in a prime location! Situated in a great neighborhood with easy access to everything, this move-in ready home checks all the boxes. Featuring a desirable split floor plan, this home offers both functionality and privacy. Inside, you’ll find brand new windows, beautiful new wood flooring, and new carpet in the guest bedrooms, along with fresh interior paint, new baseboards and door trim, and updated ceiling fans and light fixtures throughout. The fully renovated kitchen showcases new cabinets with soft-close features and quartz countertops, creating a clean, modern feel. Bathrooms have been refreshed with new toilets, and every detail has been thoughtfully updated. Enjoy the outdoors with a screened porch featuring new outdoor carpet and a new irrigation system to keep your yard looking its best. The home also features a newly painted exterior and a roof replaced in 2022 for added peace of mind. This is a truly turnkey home with quality upgrades throughout—ready for its next owner to move in and enjoy.

Listing is courtesy of: LISTY, LLC (561-309-9240)

Listing Agent: Nicholas Macy (561-309-9240)

Remarks: Tucked within the prestigious enclave of Windsong Lakeside in Winter Park, this extraordinary estate is a masterclass in refined living—where thoughtful design, cutting-edge technology, and timeless elegance converge. From the moment you arrive, the circular drive and stately presence set a tone of quiet grandeur. Step inside, and the home unfolds with an effortless sense of scale, defined by soaring vaulted ceilings and an abundance of natural light filtering through custom windows. Every detail has been meticulously curated—from the rich new flooring installed in 2025 to the soft glow of Currey & Co. lighting that adds warmth and sophistication to each space. Designed for both comfort and control, the residence is fully integrated with a wireless home automation system, allowing seamless management of lighting, climate, security, and more. Three A/C units ensure optimal comfort, while a new tankless water heater, water softener, and whole-home surround sound system elevate everyday living. A comprehensive security camera system and ADT Home Control provide peace of mind with modern convenience. Each of the four bedrooms is a private sanctuary, complete with its own en-suite bath, offering an elevated sense of privacy for residents and guests alike. The primary suite is a retreat unto itself, featuring custom built-in storage and electric storm shutters with blackout capability. The spa-inspired primary bath showcases a dual Grohe shower system, thermostatic auto tub filler and integrated TV - creating an environment of indulgence and serenity. At the heart of the home lies a newly renovated (2025) chef’s kitchen—an exquisite blend of form and function. Outfitted with premier appliances including a Wolf six-burner gas range, Sub-Zero refrigerator, Monogram built-in microwave, and dual dishwashers, the space is designed for both intimate meals and grand entertaining. Custom cabinetry with integrated lift features, dual sinks, filtered water dispenser, and elegant stone countertops complete this culinary haven. The living room invites relaxation with its newly renovated gas fireplace (2025), while a dedicated office offers bespoke built-in cabinetry with marble surfaces and glass shelving—ideal for sophisticated work-from-home living. Upstairs, the home transforms into an entertainment destination, complete with a projector theatre setup, wet bar, additional powder bath, and extensive storage. A dedicated A/V closet and the potential for an upstairs laundry add both function and flexibility. Outdoors, a private resort-style oasis awaits. The backyard has been completely reimagined, featuring lush turf, a sun deck platform, and even an in-ground trampoline—blending luxury with playfulness. The saltwater pool and spa, enhanced with upgraded LED lighting and a new heater (2025), were fully refinished and redesigned in 2021 to create a serene and visually stunning escape. A fully equipped summer kitchen—complete with a built-in gas grill, dual burners, refrigerator, and screened enclosure—sets the stage for unforgettable gatherings under the Florida sky. The three-car garage is equally impressive, featuring a Wallbox Level 2 electric vehicle charger (2023), seamlessly blending luxury with modern sustainability. This is more than a home—it is a statement of lifestyle, craftsmanship, and elevated living in one of Central Florida’s most sought-after lakefront communities.

Listing is courtesy of: KGV REALTY GROUP (407-474-0844)

Listing Agent: Kristin Vogt Pllc (407-417-7206)

Remarks: ***WINTER PARK **** 4 BEDROOMS ****3 BATHROOM **** PAID OFF SOLAR ***** WILL HELP BUYER****METAL ROOF ***1/3 ACRE*** Welcome to 1923 Linden Rd, Winter Park—a well-maintained single-story residence offering space, character, and an exceptional location. Built in 1955, this solid masonry and concrete block home features 4 bedrooms, 3 full bathrooms, and approximately 2,117 heated square feet, with 2,281 total building square feet. Located in the highly desirable area of Winter Park, the home provides convenient access to shopping, dining, parks, and top-rated schools, as well as nearby Park Avenue and downtown Orlando. The interior offers a functional layout with multiple living areas, ideal for both everyday living and entertaining. Original character elements such as plaster interior walls and two fireplaces add warmth and timeless appeal. The centrally located kitchen provides ample workspace and flows seamlessly into the main living areas. Situated on a generous 0.315-acre lot (13,717 sq ft) with approximately 117 feet of frontage and 114 feet of depth, the property offers plenty of room for outdoor enjoyment, future enhancements, or expansion. Additional features include Metal Roof that allows for 20 degrees cool, continuous footing foundation, and package cooling system. A strong opportunity for buyers seeking a well-built home with character, space, and long-term value in a prime location.

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

Listing Agent: Milton James (407-572-4458)

Remarks: PRICED TO SELL! Charming, quaint, and character-filled 3-bedroom, 2-bath home in the heart of Winter Park. From the moment you enter, you’re welcomed by warm original cognac hardwood floors that flow throughout the main living areas, creating a timeless and inviting atmosphere. The home offers a comfortable and functional layout with open yet cozy living and dining spaces, ideal for everyday living and entertaining. The remodeled kitchen blends classic charm with modern convenience and connects seamlessly to both indoor and outdoor living. The primary bedroom and bathroom offer a cozy, intimate setting, with excellent potential for future expansion or customization to suit your needs. While there are no walk-in closets, all closets have been custom-designed by California Closets, maximizing storage and organization throughout the home. Step outside to a private backyard retreat designed for Florida living. The saltwater pool, fully equipped outdoor kitchen with built-in bar, and tranquil pond with waterfall create a serene, zen-like setting perfect for relaxing or entertaining. Additional features include a tiled 2-car garage with abundant storage space, roof (2023), AC (2023), ductwork (2022), and a hybrid energy-efficient water heater (2020). Ideally located near top-rated schools, shopping, dining, and parks, this home offers a rare blend of charm, lifestyle, and opportunity in a prime Winter Park location.

Listing is courtesy of: ZEN LIVING HOMES LLC (407-800-2717)

Listing Agent: Nydia Marrero (407-620-6221)

Remarks: Under Construction. 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.

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

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

Remarks: 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: 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: Tucked behind the gates of Cypress Reserve, this stunning custom-built lakefront home sits on 110 feet of private waterfront along the serene shores of Bear Gully Lake. Inspired by a featured Southern Living plan and thoughtfully expanded, the home blends timeless architecture with generous, well-appointed living spaces — all framed by panoramic water views, rolling greens, and towering oaks and cypress trees that define the lakefront lifestyle at its finest. Inside, the main level offers a gracious and versatile floor plan with formal living and dining rooms, a family room anchored by an electric fireplace, and a dedicated office or flex space. The spacious kitchen features custom cabinetry, generous prep space, and an adjoining dinette — with plenty of room to add an island — while a large laundry room with extensive cabinetry and a utility sink, plus a half bath, ensure exceptional everyday functionality. The first-floor primary suite is a true sanctuary, offering breathtaking lake views, a spa-inspired en suite with a jetted tub, walk-in shower, a very desirable his and her split bath with abundant counter space and storage, and an oversized walk-in closet complete with built-in shelving and dresser drawers. Upstairs, two oversized bedrooms each enjoy their own private en suite with tub/shower combination, ample closet space, and comfortable proportions. The enormous bonus room above the garage fills with natural light through dormer windows and offers endless possibilities. A walk-in attic provides exceptional storage rarely found in homes of any size. Step out to the covered back porch and take in sweeping panoramic views of Bear Gully Lake — a breathtaking backdrop that shifts beautifully with the light throughout the day - this is Florida lakefront living at its absolute finest. Meander down to your private dock for a morning kayak or a sunset boat ride, then rinse off at the east-facing porch complete with a sink and outdoor shower before heading back inside. The rolling greens, ancient oaks, and towering cypress trees frame the property in natural splendor, and an additional storage room with its own entrance and hurricane shutters ensures everything you need for lake life is right at hand. Set in the gated community of Cypress Reserve with easy access to top private schools including The Geneva School and Trinity Prep, and with convenient proximity to SR-417 for effortless travel to Orlando International Airport and beyond, this is a rare opportunity to own a one-of-a-kind lakefront estate in one of Winter Park's most coveted settings.

Listing is courtesy of: KELLY PRICE & COMPANY LLC (407-645-4321)

Listing Agent: Kelly Price (407-645-4321)

Remarks: Pre-Construction. To be built. Discover a rare opportunity to build a fully custom residence in the highly sought-after Killarney Shores neighborhood of Winter Park—one of the last areas where new construction at this level remains attainable below $1.3M. Exclusively curated by The Hope Group, this offering pairs premier design with a seamless build experience alongside Deep Roots Construction, MJS Designers, and Collins & Co. From concept to completion, every detail is thoughtfully orchestrated, allowing the future owner to tailor finishes, layout, and architectural style to match their vision. Ideally positioned just minutes from Park Avenue’s renowned dining, boutique shopping, and vibrant lifestyle, the property also offers convenient access to I-4, College Park, and Downtown Orlando—delivering both prestige and connectivity. The proposed residence spans approximately 2,500 square feet and is designed with intentional flow, abundant natural light, and refined modern finishes. The layout allows for elevated indoor-outdoor living, with the option to incorporate a private pool and outdoor entertaining space. Located within close proximity to major medical centers, including AdventHealth Winter Park (approximately 2.5 miles), AdventHealth Orlando (approximately 4 miles), and Orlando Health Orlando Regional Medical Center (approximately 5 miles), this location offers both lifestyle and practical convenience for medical professionals and those seeking proximity to top-tier healthcare. Opportunities like this are increasingly limited in Winter Park—secure your homesite and begin designing a one-of-a-kind residence in one of Central Florida’s most desirable zip codes.

Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)

Listing Agent: Vinny Lay (407-756-4255)

Remarks: 330 Elkhorn Ct is a beautifully renovated, move-in-ready home located in the highly desired Winter Park Pines community. Inside, you’ll find a bright, open layout with wide-plank flooring, recessed lighting, and a modern neutral color palette that feels clean and inviting. The kitchen has been thoughtfully updated with shaker-style cabinetry, sleek countertops, stainless steel appliances, and designer finishes—including a farmhouse sink and gold hardware/fixtures that add a high-end touch. The bedrooms offer comfortable space with updated finishes throughout, while the oversized backyard provides plenty of room to relax, entertain, garden, or create your ideal outdoor setup. Conveniently located near shopping, dining, parks, and major roadways—and zoned for top-rated schools including Winter Park High School—this home is a standout opportunity in one of the area’s most sought-after neighborhoods.

Listing is courtesy of: LA ROSA REALTY CW PROPERTIES L (407-910-2168)

Listing Agent: Neil Chetram (407-752-1597)

Remarks: Masterclass in Modern Luxury on Alabama Drive 3 Beds | 3 Baths | Premier Corner Lot | Winter Park, FL Nestled on a premier corner lot at the intersection of Alabama Drive and Palmer Avenue, this fully renovated 3-bedroom, 3-bathroom residence stands as a masterclass in modern luxury. Located in one of Winter Park’s most highly sought-after areas, the property is beautifully framed by the iconic tree-lined brick streets of the Chain of Lakes district and surrounded by historic estate homes. The Lifestyle: Central Florida's Premier Luxury Destination Living at 1110 Alabama Drive means immersing yourself in the rich culture and timeless elegance of Winter Park. This historic city is celebrated for its deep canopy oak trees, world-class amenities, and a laid-back atmosphere. A Walker's & Boater's Paradise: You are just a short, scenic stroll from the exclusive boutiques, acclaimed sidewalk cafes, and Michelin-starred dining lining Park Avenue. Spend your weekends grabbing fresh produce at the famous local farmers' market or launching a boat onto the stunning interconnected freshwater Chain of Lakes. Surrounded by Beauty: This home places you moments from the breathtaking, massive cypress trees and vibrant blooms of Kraft Azalea Gardens, as well as the private, historic Winter Park Racquet Club. The Residence: Fully Renovated & Refined No detail has been spared in this total home transformation, seamlessly blending a classic, highly coveted location with cutting-edge modern amenities. Gourmet Kitchen: Discover a massive chef’s footprint appointed with premium granite countertops and high-end finishes, making it the focal point for both daily living and grand entertaining. Designer Upgrades: Rich hardwood flooring flows effortlessly throughout the home, beautifully complemented by high-efficiency upgraded Pella windows that provide enhanced aesthetics and excellent energy savings. Modern Infrastructure: Enjoy total peace of mind with meticulously updated systems, including a 5-year-old tankless water heater, a custom-designed garage door, and a well-maintained 12-year-old roof. The Ultimate Outdoor Oasis Designed intentionally for the true Florida lifestyle, the exterior of this property serves as a completely private sanctuary. Signature Screened Porch: Step out into an expansive outdoor living space anchored by a cozy gas fireplace—serving as the ultimate venue for year-round entertaining. The Grounds: Relax by the private, open-air pool surrounded by lush, tropical landscaping and a fully irrigated lot, capturing resort-style living in your own backyard. Whether you are searching for a turnkey luxury residence or looking to secure a rare, premier canvas in Central Florida’s most coveted zip code, this estate has it all.

Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)

Listing Agent: Omar Albaba (813-951-7475)

Remarks: Under contract-accepting backup offers. Set on an oversized 1/3-acre lot in the heart of Winter Park, this one-owner home was custom built in 1997 and has been meticulously maintained ever since. Solid block construction, timeless stone accents, and mature landscaping give it great curb appeal from the moment you arrive. Step inside to a spacious foyer with hardwood floors that carry through most of the main living areas. To the right, the living room features built-in shelving and a bay window that fills the space with natural light. It flows into the formal dining room, also with hardwood floors, plantation shutters, and plenty of room to host. A conveniently located powder bath serves this side of the home. To the left is the heart of the house - a generously sized kitchen with abundant white cabinetry, stone countertops, a center island, double ovens, a built-in pantry with pull-out storage, and a breakfast bar. The separate eat-in area overlooks the backyard and opens to the screened porch through French doors. The kitchen connects to a large family room with coffered ceilings, a gas fireplace, built-ins, and additional French doors leading outside. The home offers a three-way split floor plan for privacy. The primary suite sits on its own wing and is very spacious, featuring crown molding, a bay window, and French doors to the patio. The en-suite bath includes double vanities, large "His & Hers" walk-in closets with custom closet systems, a soaking tub, separate shower, and private water closet. On the opposite side of the home, you’ll find a generously sized secondary bedroom with its own en-suite bathroom and walk-in closet. Toward the back of the house is a third bedroom with a built-in desk, French doors to the exterior, and an en-suite Jack-and-Jill bath that also serves the family room. The first floor also includes an indoor laundry room with ample cabinetry and a utility sink. Upstairs, a huge bonus room offers incredible flexibility - game room, media room, office, or potential fourth bedroom. There is also space to add a bathroom if desired. Out back, a large screened porch with high ceilings overlooks a peaceful, lushly landscaped yard with plenty of room to enjoy Florida living. Additional features include plantation shutters throughout, a spacious two-car garage, and an unbeatable location just minutes from Park Avenue’s shopping and dining. Zoned for highly rated Dommerich Elementary, Maitland Middle, and Winter Park High. Call today to schedule your private showing!

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

Listing Agent: Maria Van Warner (407-256-8066)

Remarks: Welcome to 1760 Alabama Drive, a striking mid-century residence where architectural character, thoughtful modernization, and exceptional livability come together in one of Winter Park’s most desirable neighborhoods. Spanning 2,841 square feet, this distinctive home celebrates authentic mid-century design with clean lines, intentional geometry, and expansive walls of glass that bring the outdoors in. Natural light pours through oversized windows throughout the home, while dramatic 20 foot hedges on both sides create a rare sense of privacy. The result is a space that feels bright, open, and connected to nature while remaining remarkably secluded. At the heart of the home is an extraordinary chef’s kitchen designed for anyone who truly love to cook. Completely custom cabinetry is paired with restaurant quality appliances to create a culinary workspace that rivals professional kitchens. This is not decorative luxury, it is functional craftsmanship. Every detail has been considered to support both serious cooking and effortless entertaining, with the kitchen flowing naturally into the home’s main living areas and gathering spaces. The home offers four bedrooms and two and a half baths, including an impressively scaled primary suite that serves as a private retreat within the home. One of the most memorable spaces is the massive great room anchored by a functional fireplace. Currently styled as a study and office, the room offers incredible flexibility and architectural presence, equally suited as a dramatic living room or central gathering space. Outdoor living is just as compelling. The backyard is designed for entertaining at scale, centered around a fully realized outdoor gourmet kitchen and generous gathering area built for long dinners, celebrations, and relaxed evenings under the Florida sky. A private rear driveway and two car garage provide convenience and privacy rarely found in this part of Winter Park. And then there is the location. 1760 Alabama Drive sits within Winter Park’s coveted Golden Triangle, known locally as The Vias, just steps from Kraft Azalea Park and moments from the Chain of Lakes lifestyle. Tree lined streets, lakefront sunsets, and one of the area’s most respected racquet clubs are all part of the daily rhythm here. In a market where location ultimately drives long term value, this address delivers something rare: architectural distinction, extraordinary privacy, and immediate access to some of Winter Park’s most treasured spaces. This address is not just a location, it’s a strategic position.

Listing is courtesy of: DAILLAND REAL ESTATE (407-666-7860)

Listing Agent: Brian Ruth (407-881-8185)

Remarks: Under Construction. Estimated completion August!! Experience modern luxury living in the heart of Winter Park with this beautifully designed pool home at 1810 Hollywood Avenue. Offering 4 bedrooms, 3.5 bathrooms, and 2,604 square feet of thoughtfully planned living space, this residence blends high-end finishes with everyday functionality in one of Central Florida’s most sought-after locations. The open-concept layout creates an easy, natural flow between the living, dining, and kitchen spaces, ideal for both entertaining and daily life. The kitchen serves as the centerpiece of the home, featuring sleek design elements, quality craftsmanship, and ample storage that feels both elevated and practical.The first floor primary suite provides a private retreat with a well-appointed en-suite bath and generous closet space, while the additional bedrooms offer flexibility for guests, a home office, or growing households. Step outside to your own backyard oasis, complete with a pool and space to relax or entertain year-round, your personal escape without leaving home. A two-car garage adds convenience and storage, rounding out the home’s smart design.Perfectly positioned near Park Avenue, Winter Park Village, and downtown Winter Park, this location offers easy access to dining, shopping, and everyday conveniences while still feeling tucked away in a quiet residential setting. Zoned for Winter Park High School, this home delivers on location, lifestyle, and long-term value. 1810 Hollywood Avenue is where modern comfort meets classic Winter Park living.

Listing is courtesy of: REAL BROKER, LLC (855-450-0442)

Listing Agent: Ken Pozek (407-813-2773)

Remarks: One or more photo(s) has been virtually staged. Welcome to this aesthetic custom luxury home in an unbeatable Winter Park location.From the moment you arrive, the custom landscaping and automated lighting make a statement, day or night.At the center of the home, the chef's kitchen is both a showpiece and a performance space. A commanding 48-inch Z-Line gas range with 8 Italian-made brass burners anchors the room, complemented by Café luxury appliances, a stainless steel refrigerator, quartz countertops, and custom cabinetry. The walk-in pantry with floating shelves and under-shelf lighting adds both beauty and function. An indoor wine bar with built-in cabinetry and wine refrigerator enhances the entertaining experience, while an upstairs beverage station keeps every level equally equipped.The primary suite is a full spa experience. The glass enclosed shower features a rain head, body jets, and handheld fixtures. A soaking tub, dual vanities with quartz counters, and a generously proportioned walk-in closet complete the retreat. Imported aged brass designer light fixtures are included in the sale. Philips Hue smart lighting synchronizes every indoor and outdoor light in one app, and a smart security camera system with fingerprint keypad entry completes the tech package. The outdoor living experience rivals the interior. A covered lanai with a fully equipped summer kitchen, including a built-in grill, dedicated refrigerator, and generous prep space, flows into a landscaped courtyard designed with an Italian villa, Mediterranean feel. As evening falls, intentional landscape lighting transforms the grounds into an intimate setting perfect for al fresco dinners, fireside gatherings, or projecting the big game under the stars. Walk to pickleball courts, athletic fields, and a premier wellness facility. Park Avenue's celebrated boutiques and dining are just minutes away. New construction of this caliber is increasingly rare in Winter Park. Schedule your private showing today. The furniture and décor, curated by a professional design team, are negotiable, making it possible to move in with the full look already in place.

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

Listing Agent: Norma Gonsalves (407-451-9533)

Remarks: Rare opportunity in a quiet Winter Park neighborhood! This oasis home offers nearly 2,000 sq ft of living space PLUS a fully equipped studio apartment with private entrance, kitchenette, full bath, fireplace, separate A/C, and generous storage—ideal for guests, multi-generational living, or rental income. The main home features a freshly painted interior and exterior, new LVP flooring throughout, and a completely remodeled kitchen with new appliances. The primary suite includes an en suite bath that has been remodeled, and three additional bedrooms provide ample space for family or home office needs. Enjoy the Florida room overlooking a fenced, private backyard, perfect for entertaining. Roof replaced in 2024. A/C replaced in 2016. Zoned for top-rated Winter Park High School and conveniently located near Park Ave, shopping, dining, Costco, and major roadways. Move-in ready with room to personalize. Don't miss this versatile and rare Winter Park find!

Listing is courtesy of: HONEST REAL ESTATE COMPANY (407-417-1314)

Listing Agent: John Hwangbo (516-708-6207)

Remarks: 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.

Listing is courtesy of: EQUITYPRO LLC (407-203-6860)

Listing Agent: Navid Rokh (321-900-5977)