Homes For Sale in Winter Park 32789 - 201 homes

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: 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: 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: 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: Under contract-accepting backup offers. Enjoy the Winter Park lifestyle in this spacious 2-bedroom, 2-bath lakefront condo offering 1,900 square feet in the heart of downtown Winter Park. Enjoy serene lake views from the 120 sq ft screened porch—perfect for morning coffee or evening wine. The light-filled living area features soaring 8 ft 10 in ceilings, creating an open, airy atmosphere. A cozy family room offers built-in shelving and a wet bar, ideal for relaxing or entertaining. The galley kitchen features granite countertops, a natural gas range, and a convenient laundry closet with a stackable washer and dryer. The primary bedroom boasts a walk-in closet with ample storage, additional closet in the rear alcove, and a primary bath with dual sinks and a walk-in shower. The secondary bedroom includes an adjoining office alcove, while the secondary bath offers a walk-in shower. Neutral tones flow throughout the condo, and the dinette provides beautiful views of Lake Osceola. Completely rebuilt in 2011 with new plumbing, electrical wiring, air conditioning, and ductwork, this home offers modern efficiency and peace of mind. A covered boat slip (#15) with lift, two covered parking spaces in the gated underground garage accessible with a key access in the elevator, approximately 90 sq ft of private utility storage, and a community pool complete this exceptional offering. Just steps from Park Avenue, enjoy walkable access to premier shopping, dining, museums, and seasonal events, making this a rare opportunity for true lakefront living in one of Winter Park’s most desirable locations.

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

Listing Agent: Megan Cross (407-353-9997)

Remarks: Welcome to 647 Randy Lane in Winter Park. This is a rare opportunity to own a designer residence in one of the area's most sought-after neighborhoods, offered for the first time in over 10 years. Situated on a spacious corner lot, 0.36 acres, this meticulously maintained home showcases timeless charm paired with modern luxury. Lush, mature landscaping surrounds an oversized private pool, expansive patio and generous backyard, creating a Florida outdoor living experience ideal for entertaining or relaxing year-round. Inside, the home features an open-concept floor plan designed for both comfort and style. The chef's kitchen stands out, appointed with quartz countertops, premium Wolf double ovens and a built-in Sub-Zero refrigerator, delivering high-end performance with sophisticated design. Seamless indoor-outdoor flow enhances the living experience, leading to a resort-style backyard retreat complete with ambient lighting, perfect for evening gatherings and weekend enjoyment. Ideally situated minutes from Park Avenue's renowned dining, boutique shopping, and cultural attractions, this home offers unparalleled convenience in the heart of Winter Park. Located in one of the area’s most desired school districts, including Audubon K-8 and Winter Park High School. The home is equipped with updated features like a newer roof (2024), solar panels (2024), resurfaced pool and tile (2021), well irrigation, tankless gas water heater, oversized indoor laundry room and more. This exceptional property blends luxury, location and lifestyle-making it a standout opportunity in the Winter Park real estate market.

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

Listing Agent: Sara Cambron (321-277-8444)

Remarks: 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.

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

Listing Agent: Drew Henner (407-406-0662)

Remarks: Welcome to an exceptional opportunity in the highly desirable Park Grove community, an impeccably updated one-story residence ideally situated just moments from the vibrant shops and dining of Park Avenue and all that downtown Winter Park has to offer. With charming curb appeal, pristine landscaping and timeless architectural appeal, this home makes a stunning first impression. Inside, a thoughtfully designed floor plan offers seamless flow, perfectly suited for both everyday living and effortless entertaining. Beautiful wood flooring spans the main living areas, while the Florida room showcases distinctive Mexican tile, adding warmth and character. Designer lighting, curated tile selections and stylish wallpaper accents create a bright, inviting aesthetic throughout. The formal sitting room, complete with custom built-ins and an elegant dining room provide refined gathering spaces. At the heart of the home, a light-filled kitchen opens to the spacious family room, where a cozy wood-burning fireplace serves as a focal point. The adjacent Florida room is lined with windows, offering serene views of the sparkling pool and lush, private backyard. The generously sized primary suite is thoughtfully positioned for privacy, featuring its own wood-burning fireplace, a large walk-in closet and a beautifully appointed ensuite bath with dual vanities and an oversized walk-in shower. Four additional bedrooms are located on the opposite side of the home, two of which include ensuite baths, ideal for guests or multi-generational living. Outdoor living is equally impressive, with a beautifully paved lanai overlooking the pool and ample space for alfresco dining, entertaining and relaxing poolside. Tucked away in one of Winter Park’s sought-after neighborhoods, this home offers tranquility and convenience, with easy access to downtown Orlando, major hospitals, top-rated public and private schools and key roadways. A rare blend of style, comfort and location; this is Florida living at its finest.

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. TRANSFERABLE TERMITE BOND INCLUDED. Welcome home to the charm and character of the bygone days. This 3-bedroom, 2-bathroom home offers 2,556 square feet, with the historic main home originally built in 1922. Featuring original antique wood floors, a classic fireplace, and a one of a kind upstairs loft, there's nothing quite like it! A charming front porch welcomes you into the living room with a fireplace. A front room currently used as a formal parlor or sitting room doubles as the third bedroom, also ideal for entertaining or reading. Two additional bedrooms and full baths are located down the hall. The dining room sits just off the main living space, with French doors opening into the hallway. The kitchen is positioned toward the back of the home with a tucked away laundry closet. Accessed by an interior staircase off the kitchen, the HIGHLIGHT of the home is the handcrafted upstairs loft with design in a class of itself. Currently used as an exquisite billiards room and library, this flexible space can serve as a library, office, or creative retreat, and features a balcony with views of Lake Killarney. Additional features include 42-inch kitchen cabinets, stone countertops, a roof replaced in 2018, AC replaced in 2019. Wind mitigation passed April 2024, septic pumped October 2025, and on top of it all, no HOA! Conveniently located minutes from Downtown Winter Park, Park Avenue, Rollins College, and just minutes from I-4, this is a truly unique property offering craftsmanship and character rarely found today.

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Veronica Figueroa (407-519-3980)

Remarks: Under contract-accepting backup offers. Walk in and feel instantly at home in this stunning 5-bedroom, 3-bath POOL home with a 3-car garage, offering over 3,600 square feet of living space on more than ¾ of an acre in the highly desirable Sevilla neighborhood of Winter Park. Backing directly to Howell Creek and Mead Gardens, this property offers the rare luxury of no rear neighbors and exceptional privacy. Upon entry, you’re welcomed by beautiful wood floors and versatile spaces to the left that can serve as a formal living room, dining room, office, or playroom. Continue into the impressive family room, featuring vaulted ceilings, skylights, and a wood-burning fireplace, creating a light-filled and inviting atmosphere. To the right wing of the home are four bedrooms and two bathrooms, including the primary suite. One secondary bedroom connects to the primary, making it ideal for a nursery, home office, or sitting room. The spacious primary retreat offers large walk-in closets, dual vanities, a soaking tub, separate shower, and French doors that open directly to the pool and backyard oasis. The kitchen, located just off the family room, features travertine flooring and flows seamlessly into a huge pantry, oversized laundry room, drop zone, and a second primary suite with ensuite bath—perfect for guests or multigenerational living. Outside, the home has been meticulously maintained, showcasing a new roof (2023), exterior paint (2018), pavered circular driveway, well, and lush tropical landscaping that enhances the home’s curb appeal. Additional features include a three-car side-entry garage, pool heater, designer lighting, engineered hardwood floors, and crown molding throughout. Located within the highly sought-after Winter Park School District (Audubon K-8 and Winter Park High School) and just minutes from Park Avenue, Central Park, Rollins College, SunRail, the Winter Park Farmer’s Market, and world-class shopping and dining. Schedule your private showing today—this exceptional home won’t last long!

Listing is courtesy of: VOSS REALTY INC (407-456-0777)

Listing Agent: Lindsay Kaye Voss (407-456-0777)

Remarks: Beautifully built in 2022 by Lonnie Richardson, this custom one-story home sits on a quiet cul-de-sac in the heart of Winter Park. Designed with a modern, timeless style, it offers luxury finishes paired with a warm, comfortable feel. The home features 4,060 square feet, including four en-suite bedrooms, five full bathrooms, a powder bath, and a bonus room with a built-in office. The spacious gourmet kitchen overlooks the main living areas and pool, and is equipped with premium Wolf appliances and a separate chef’s kitchen for added convenience. Enjoy seamless indoor-outdoor living with a covered lanai featuring motorized screens, heaters, and a mosquito misting system. The outdoor space also includes a summer kitchen, gas fire pit, and a pool equipped with a swim jet system that creates a continuous current, effectively transforming it into an endless lap pool. A detached fitness studio with a steam shower provides a private wellness retreat. Additional highlights include custom built-ins, engineered hardwood floors and surround sound throughout. The oversized two-car garage offers epoxy flooring, custom storage, and a dog wash station. Irrigation is supplied by a private well, and the home also features underground utilities and a full security system. The exterior is designed for both beauty and low maintenance, with manicured landscaping and artificial turf that stays lush year-round. With no HOA, added privacy, and exceptional attention to detail throughout, this home offers a rare opportunity to experience luxury living at its finest. This home is conveniently located near the Enzian Theater and less than a mile from Winter Park Village, with top-rated schools nearby, this home combines comfort, style and an unbeatable location. Schedule your private showing today.

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

Listing Agent: Damian Bergler (650-398-5968)

Remarks: Under contract-accepting backup offers. Luxury living in Winter Park 32789 in this well-appointed, fee-simple townhouse just steps from Park Avenue, with no HOA or condo fees. Three-story home features refinished hardwood floors (Knight Flooring), high ceilings, crown moldings and a PRIVATE ELEVATOR for easy access to all levels. The first floor offers a flexible bedroom, currently used as an office and bedroom along with a full bath, spacious laundry room with quartz counters, and plenty of storage. On the second floor, you’ll find an open living and dining area with a gas fireplace, built-ins, plus a large screened porch with a retractable screen and summer kitchen, ideal for entertaining. The kitchen includes stainless appliances, gas cooktop, quartz island, built-in breakfast banquette seating and bar. Upstairs, the third floor has a second bedroom with en-suite bath and a generous primary suite with custom large walk-in closet and a bright Florida room with French doors and lots of windows. The primary bath features dual granite quartz, lighted mirrors, spa tub and separate shower. Additional highlights include a new roof, A/C systems updated in 2018 and 2024, landscaping improvements, a two-car garage with extra parking spaces, smart home features and a garage refrigerator that conveys. All of this in a highly walkable location near shops, dining, parks, and golf, without the upkeep of a yard. Ava, Boca, Prato, Imperial, Garp & Fuss restaurants are steps away! Saint Margaret Mary is across the street. Enjoy the immaculate public Winter Park Nine Golf Course and historic Casa Feliz for events and concerts and Morse Museum housing the comprehensive works by Louis Comfort Tiffany. Multiple events in the park - Winter Park Arts Festival, holiday events and tree lighting, popcorn in the park movies, live music and more! Furnishings may be available.

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

Listing Agent: Jennifer Sloan (407-810-8333)

Remarks: Winter Park 1964 Charmer! This wonderful ranch is located just minutes to Downtown Orlando as well as Park Ave. With over 4300 sq ft of living space, this, 4 bed/5.5 bath home is in the prime location. Upon entering you'll notice just how light and bright this home shows, to your right you will find a home office space. Rich dark wood, custom cabinetry and dramatic lighting provide the perfect space to start your morning or end your day. To the left of the entry, you will find the large formal living room with 1 of 2 gas fires places located in this home. The bay window lets you take in views of your lush landscaped front yard and fills the space with tons of sunlight. Stepping off the entry you are greeted with a large formal dining room space. Sliders lead to the patio and the unique courtyard patio gives you views of your pool from not only the dining but the primary and family room all with sliders making this the perfect patio for parties, social gatherings and events. Just off the dining room you will find the great room including the breakfast area with built in cabinetry, the family room and the kitchen. The heart of the home is your kitchen, and this space has been designed for the chef of the home. White cabinetry, island, solid surface counter tops, lighting, and a huge walk-in pantry are just a few of the special touches you will find. Stainless steel appliances: Sub-Zero refrigerator, Bosh dishwasher, double oven, and microwave all the tools needs to create amazing meals. The family room's jewelry is the barrel ceiling a special touch you won't find often. Gas fireplace, spacious, Sliders leading to the patio as well as a screened patio area. The family room also includes a wet bar with ice market and wine frig. Just off the living room is the half bath. A separate area off the living could be a mother-in-law suite, she or he cave or the options are endless. a large bonus room includes a full bath which also doubles as the pool bath, sliders leading to a private yard space and a sink area. Upstairs in this area you will also find a full bedroom with vaulted ceilings and a full bath. To the right of the dining room, you will find 2 additional rooms and 2 full baths. The primary suite includes a sitting room with double doors leading to the bedroom, massive suite with bay window and views of the pool. not 1 but 2 full baths and 2 walk in closet because why share when you can have your own. This home also includes 2 tankless heaters, newer roof, well for sprinklers, home generator, skylights, dog run circular driveway custom drapes, auto blinds, freshly painted, artificial turf and so much more. So what are you waiting for?

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

Listing Agent: Steven Looper (321-662-3582)

Remarks: Under Construction. Opportunities like this rarely present themself, just a eight-minute walk from the iconic shops, restaurants, and cafés of Park Avenue, 40 Palmer represents a rare convergence of architectural significance, uncompromising craftsmanship, and premier Winter Park location. Built by Vimaro Homes, this extraordinary new construction estate is a statement piece that redefines what luxury living looks like in the heart of Winter Park. The exterior architecture is refined yet commanding, with classical influences interpreted through a modern lens, setting the tone for the exceptional level of design and finishes found inside. One of the most remarkable features, and an offering rarely found in Winter Park, is the underground four-car garage. Designed to discreetly accommodate an impressive vehicle collection, the garage is complemented by a striking spiral staircase that rises from the basement through the main living level and continues to the second floor. The family room is nothing short of breathtaking, featuring bespoke millwork with integrated shelving, soft architectural lighting, and a dramatic fireplace wrapped entirely in marble. The kitchen is a culinary showpiece designed for those who expect nothing less than perfection. Calcutta marble countertops cascade across the space, paired with stunning custom cabinetry, and a professional-grade Thermador appliance suite. A dedicated dirty kitchen allows for discreet preparation, while an expansive walk-in pantry ensures effortless hosting and immaculate presentation. The primary bedroom wing features a spa-inspired bathroom finished in rich marble, featuring dual vanities, a freestanding soaking tub and an enormous walk-in closet with a separate washer and dryer. Upstairs, a dedicated laundry room and a spacious secondary living area provide flexibility for family living, guests, or relaxation. The lower level extends the home’s versatility, offering a workshop, dedicated holiday and seasonal storage, and seamless elevator access to the main level of the home. Outdoor living is equally impressive. A large covered exterior lanai with a pool bath and full summer kitchen creates a seamless indoor-outdoor lifestyle, ideal for entertaining year-round. The backyard is truly resort-inspired, featuring a large swimming pool, sunken fire pit, and spa, all set within a private, beautifully secluded outdoor setting. What ultimately sets 40 Palmer apart is not just its design or finishes, but its unmatched combination of luxury and location. Just minutes from Park Ave shopping and restaurants, moments from the famous Winter Park Golf Course, yet privately tucked away, this home offers a lifestyle that is both vibrant and exclusive. A truly rare opportunity to own a part of the exceptional standard of living delivered by Vimaro Homes.

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

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