Winter Park Single Family Homes For Sale - 255 homes

Remarks: Under contract-accepting backup offers. *Under Contract - Accepting Backup Offers* An expression of modern luxury by SMRS Design and Cole Homes, The Maybourne masterfully blends Neoclassical elegance with Art Deco sophistication—all just steps from Winter Park’s iconic Park Avenue. A curved, manicured driveway leads to a grand entrance featuring bespoke double doors with electromagnetic privacy glass, setting the tone for the artistry within. Inside, a European hotel–inspired foyer greets guests with precast stone-clad walls, inlaid marble flooring, and a Murano-style polyhedral chandelier. Two first-floor guest suites, each with its own bath, are adorned with rift-cut white oak millwork, curved ceilings, and crystal chandeliers. At the heart of the home lies the main salon, where oak detailing and a deco-style stone fireplace with a holographic insert create an atmosphere of understated grandeur. The two-tone oak kitchen, wrapped in natural quartzite and anchored by a curved island and custom hood, features a curated suite of professional-grade appliances: • ILVE range • Miele refrigerator, freezer, and dishwasher • Sub-Zero wine and beverage preservation systems Adjacent, a dining area glows under a custom chandelier, while the powder bath impresses with wood and marble accents, an integrated stone sink, and a Saint Louis crystal faucet by Kallista. A scullery expands the culinary capability with a chef’s sink, Samsung Bespoke laundry and refrigeration, Wolf microwave drawer, and additional Miele dishwasher—ideal for both entertaining and daily ease. The first floor primary suite, discreetly hidden behind millwork, offers a serene retreat with an opulent closet system and a marble mosaic-clad bathing suite featuring Kohler digital shower technology and MTI tub. Upstairs, two additional ensuite bedrooms, a bonus room with walk-in closet, and a secondary laundry continue the home’s standard of refined luxury. Outdoors, the residence embraces resort-style living with a natural gas summer kitchen, infinity-edge pool, and 360-degree raised glass-tile spa. A two-car garage and porte cochere, both EV-ready, provide elegant utility. Modern conveniences include Lutron HomeWorks lighting and shade prewire, built-in SONOS audio zones, pre-installed speakers, and a commercial-grade Ubiquiti WiFi network ensuring flawless connectivity throughout. A feast for the senses, The Maybourne is more than a home—it’s a statement of artistry and craftsmanship, conceived for the most discerning Winter Park resident.

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

Listing Agent: Rikhil Amin (407-792-8069)

Remarks: Welcome to this charming, meticulously maintained 3-bedroom, 2-bath residence in the heart of Winter Park—lovingly cared for by the same owner for over 30 years. This home reflects true pride of ownership with thoughtful updates and improvements that provide both comfort and peace of mind. Enjoy entertaining in the spacious eat in kitchen with full Stainless appliance package. Outdoor living shines with an extended paver driveway and rear patio, screened lanai, and lush, mature landscaping—creating a private, relaxing retreat perfect for entertaining or everyday enjoyment. Major upgrades include energy-efficient double-pane windows and patio door (2014), HVAC system (2020), redesigned Primary Bath Shower, updated electrical panel with new breakers including surge protection (2024), Water Heater (2024), Roof (2022). The home has also been repiped features a replaced drain field and a recently serviced septic system (2025). Additional improvements include gutters with mesh guards (2019), vinyl fencing and garage door hardware updates (2025). Designed for worry-free living, this home includes a long-standing transferable termite bond and resilient fiber cement siding for enhanced durability and protection. Ideally situated in a desirable Winter Park corridor, this home offers effortless access to both downtown Winter Park and Orlando, as well as the vibrant amenities of Baldwin Park. Surrounded by properties ranging from $600,000 to multi-million-dollar estates, the location presents an exceptional opportunity to enjoy a premier lifestyle with strong long-term value. Residents benefit from zoning to highly regarded schools and proximity to Park Avenue, Rollins College, and an array of fine dining, shopping, and cultural destinations. With convenient access to major roadways, daily commuting and connectivity are seamless. Set within an established neighborhood characterized by a blend of long-time ownership and thoughtfully updated homes, the area continues to experience ongoing growth and enhancement. A rare opportunity to own a beautifully maintained home in one of Central Florida’s most desirable communities.

Listing is courtesy of: RE/MAX SELECT GROUP (407-352-5800)

Listing Agent: Helen Thompson (407-766-7537)

Remarks: Along one of the cobblestone brick streets in the prestigious Via’s of Winter Park, this completely renovated residence pairs timeless European influence with clean architectural lines and bespoke finishes throughout. A circular driveway and manicured grounds designed by Signature Landscapes create a graceful approach. Inside, a dramatic curved staircase crowned by a breathtaking 1960s vintage Venini chandelier immediately sets the tone for the exceptional craftsmanship carried throughout the home. The main gathering room is striking and inviting, defined by vaulted ceilings, a Sequoia leathered stone fireplace hearth, and a wall of glass sliders that open seamlessly to the covered lanai and heated saltwater pool. The connection between indoors and out is effortless, designed for year-round entertaining and relaxed daily living, enhanced by a full outdoor audio system. A light-filled breakfast room sits just off the kitchen, offering an intimate everyday dining space. At the heart of the home, the custom kitchen is a showpiece. Naica leathered stone countertops and a waterfall island are complemented by custom cabinetry extending to the ceiling, a professional-grade appliance suite featuring Sub-Zero and Wolf, and convenience of two Miele dishwashers. Directly adjacent, the pantry mirrors the kitchen’s cabinetry and craftsmanship and features a built-in coffee station, seamlessly connecting to the laundry area and three-car side-entry garage. A beautifully appointed guest powder room with an integrated sink is thoughtfully positioned nearby. A separate lounge showcases a custom wet bar highlighted by dramatic stonework and an integrated sink, an elegant setting for conversation and evening gatherings. A dedicated office positioned just outside the primary suite features a wall of floor-to-ceiling shelving, cabinetry and file drawers. The primary suite serves as a private sanctuary, enhanced by vaulted ceilings, backyard views and a stately two-sided stone fireplace shared with the office. Two custom walk-in closets provide exceptional storage, while the spa-inspired bath showcases Taj Mahal leathered stone countertops with integrated dual sinks, a soaking tub and an oversized glass shower with dual showerheads. Upstairs, four additional bedrooms with custom closets are complemented by beautifully finished baths and a loft sitting area with hallway built-ins. Two of the bedrooms and a bath may be closed off to create a private suite, ideal for guests or multigenerational living. A secondary staircase leads to an impressive media room equipped with a 98-inch television, state-of-the-art 7.1 surround sound and extensive storage. Outdoor living is equally elevated, featuring a weathered marble pool deck, dedicated pool bath, newly installed summer kitchen with Coyote gas grill, hood vent, sink, and leathered stone counters and backsplash, plus an outdoor living room anchored by a two-sided fireplace and television. Modern systems include a Lutron lighting system on the main level, water filtration & softener, ADT alarm - security cameras throughout and a whole-home natural gas generator. Every element of this residence has been newly installed and custom-designed, resulting in a home that blends sophisticated design, advanced functionality, and exceptional spaces for intimate living and grand entertaining. From custom millwork to curated stone selections, this home reflects uncompromising quality and thoughtful design.

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

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

Remarks: Located on a quiet cul-de-sac in the heart of Winter Park, this traditional two-story home offers a functional, well-designed floorplan for both everyday living and entertaining. From the moment you step inside, the home has an inviting warmth that you can immediately feel. The main level features a spacious primary suite along with connected living spaces that flow easily from room to room. The primary suite and family room both feature tall ceilings and an abundance of natural light, creating a bright and inviting wing of the home. The kitchen opens to the casual dining area and family room, creating a central gathering space. French doors from the family room lead to a peaceful, southern-inspired screened patio overlooking a spacious yard on nearly half an acre. At the front of the home, a separate living room provides a quieter setting, while the formal dining room is complemented by a butler’s kitchen for added functionality when hosting. Upstairs includes four additional bedrooms with classic charm, featuring original hardwood floors and generously sized rooms, offering flexibility for guests, family, or office space. Just steps from Park Avenue and the Winter Park 9, this home offers an ideal location with easy access to shopping, dining, and golf.

Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)

Listing Agent: Jennifer King (407-595-3272)

Remarks: Experience the art of luxury living just steps from the boutiques, cafés & celebrated dining of Park Avenue, Winter Park Village, Rollins College & the iconic Winter Park Art Festival. This beautifully crafted custom one-story pool home built in 2024 blends elegant design with an effortless, modern lifestyle. THIS HOME RECEIVED THE 2025 ARDA GRAND AWARD FOR CUSTOM HOME (built). A thoughtful quad split bedroom layout offers 4 bedrooms & 4.5 baths, including a serene primary suite with Hunter Douglas automated light filtering/light blocking shades. The primary suite includes a spectacular custom walk-in closet featuring an island, 36 drawers, built-in benches, dual hampers, a safe, locking jewelry drawers & display shelving. The ensuite bath provides a spa-like retreat. Additionally, two guest suites also enjoy private ensuite baths & large walk-in closets. The showpiece chef’s kitchen is designed for both culinary mastery & entertaining, featuring Dura Supreme cabinetry, a 60" Wolf dual fuel range with griddle, pot filler, 36" Sub Zero Designer Column refrigerator, Sub Zero freezer drawers, two Bosch dishwashers, Wolf microwave drawer, Revati dual tier 57" sink with custom inserts for colander, cutting board & strainer & dual automatic faucets. Dramatic 15-foot waterfall island with Dekton countertops & matching backsplash. A hidden scullery adds even more function with a French door refrigerator, sink, pantry shelving, Dekton counters & floating LED-lit shelves. The stylish wet bar includes white oak floating shelves with LED lighting, Dekton countertops & backsplash, a glass rinser, Scotsman gourmet ice machine & Thermador refrigerator drawers. Dining room has a climate-controlled wine cellar that holds up to 240 bottles. Enjoy picking lemons, limes & oranges from your own mature trees for juicing or garnishes. The expansive family room impresses with six LED-lit floating shelves, a 60" linear gas fireplace & an extraordinary 52 feet of 10-foot-tall sliding stacking patio doors that create seamless indoor-outdoor flow. Step outside to a resort-style outdoor kitchen & living area, complete with a Dekton waterfall countertop, Perlick refrigerator drawers & kegerator, 48" DCS grill with rotisserie & 2 side burners, pizza oven, Ruvati sink with ice chest, bar-height island seating, three 60" Minka Aire remote control fans, outdoor electric fireplace & retractable screens. The app-controlled pool features water elements, bubblers, two ledge loungers with umbrella holder/end table/ice chest & a 9-seat hot tub. Custom closets are found throughout the home, including the media room with built-in Queen Murphy bed & closet & a dedicated exercise room with closet or potential fifth bedroom. Large office filled with natural sunlight. The laundry room includes custom cabinetry with built-ins for pet bowls & bed & a fold-out ironing board. Additional features include Visual Comfort lighting, Guardian security system, Trane home automation, Quantum Fiber, built-in speakers throughout the main living areas & outdoor kitchen, living room & pool, Emtek hardware, PGT casement windows & 8" white oak hardwood floors. The sellers will also provide a one-year home warranty for added benefit. This home delivers a refined, fun & effortless luxury lifestyle in one of Winter Park’s most coveted locations—where every detail is designed to impress. Finding a one-story, almost-new home on a large lot in Winter Park is like finding a rare gem!

Listing is courtesy of: ROYALTY R E BOUTIQUE INC (407-658-0601)

Listing Agent: Domenique Lombardo (407-474-7000)

Remarks: Charming 2-bed home in Winter Park located in the Golfview subdivision offering approximately 1,150 square feet of living space on a 6,414 square foot lot. Built in 1946, this single family residence features a functional layout with a blend of original character and updated interior finishes. The home includes original pine flooring in the main living areas, ceramic tile in the kitchen and dining spaces, and strong natural light from multiple window exposures. The kitchen has been updated with white cabinetry, granite countertops, and a mix of stainless steel and black appliances. The bathroom features updated finishes including a modern vanity and shower. Additional features include a covered front porch, one car attached garage with laundry area, central air conditioning with updated ductwork, and a fenced backyard with deck space suitable for outdoor use. The property is connected to public water and sewer and offers practical living with no HOA. Located near Dubsdread Golf Course and within close proximity to AdventHealth, College Park, and Downtown Orlando. Easy access to I-4 and surrounding roadways supports convenient travel to employment, dining, and retail centers. This property is suitable for a primary residence or investment opportunity in a well located Winter Park area.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Tyler Gibson Llc (877-366-2213)

Remarks: One or more photo(s) has been virtually staged. OUTSTANDING RENOVATION in a FANTASTIC LOCATION! Peace, Quiet & GOLF COURSE LIVING! This rare opportunity places you along the 13TH tee & offers tranquil backyard views of the 16TH fairway of the Winter Park Pines Golf Course (WP18)! Tree-lined street welcomes you to this completely renovated Floor to Ceiling ONE STORY beauty offers Serendipity LW Wood & porcelain tile flooring throughout. Updates include (but definitely not limited to) BRAND new kitchen with Stainless Steel Appliances, new cabinets & quartz countertops. Formal living & dining rooms PLUS Family room with vaulted ceilings featuring a new electric fireplace for amazing ambiance and sliding doors inviting you to new brick pavered 31x 11 screened porch overlooking newly refinished sparkling pool & golf course (no rear or side neighbors!!) Bedroom wing of home offers a large inside laundry room, beautiful guest/pool bath with dual sinks & shower/tub and 2 fresh guest bedrooms. THE PRIMARY SUITE has been thoughtfully remodeled with sliding doors to pool, AMAZING primary bath with oversized work-of-art shower with dual shower heads, dual vanity, separate water closet & HUGE walk-in closet! Extras include: NEW double paned windows & 3 sliding doors to pool/patio, crown molding, NEW roof November 2024, oversized 2 car garage, NEW landscaping, all NEW ceiling fans & light fixtures, NO HOA!! Zoned for Brookshire Elementary, Glenridge Middle & Winter Park High. WELCOME HOME!

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

Listing Agent: Catherine D'Amico (407-252-3210)

Remarks: Experience the perfect blend of classic elegance and modern comfort in this spacious pool home. From the moment you step inside, the open spindle staircase sets a sophisticated tone that carries throughout the residence. In the Heart of the home is an upscale Kitchen equipped with solid wood cabinetry, sleek granite countertops, and a convenient breakfast bar for your morning breakfast or casual dining. Move freely from inside to outside through 3 sets of sliding glass doors in the kitchen, dining room and great room. Just walk out anytime to the massive brick paver patio and enjoy one of the two covered patio areas. The outside is Entertainment ready as the expansive brick pavers wrap around the pool, creating a seamless environment perfect for hosting summer parties or quiet evening dips. On the cool days you can retreat to the family room to enjoy the warmth of the wood-burning fireplace. The primary Suite is a true getaway featuring direct pool access via private sliders, a generous walk-in closet, and a spa-like bath. Indulge in the soaking tub or the walk-in shower with double shower heads. Includes double vanities and ample storage for a clutter-free environment. The upper level will allow family and guests to feel right at home with three spacious bedrooms and a dedicated full bathroom upstairs. You can also rest easy knowing that the Roof was installed in 2018, the Hot Water Heater was installed in 2018, and the HVAC system was installed in 2019. An oversized 2-car garage offers room for a workbench and "toys" plus an inside laundry room and convenient half-bath are located close by. This prime location is ideally situated near A/B-rated schools, UCF, and Oviedo Hospital. Enjoy easy access to the 417 and Aloma Ave with plenty of shopping, Winter Park’s nightlife and the Tuscawilla Country Club just minutes from your front door. If this sounds like YOUR Dream home, please come see it today!

Listing is courtesy of: ELLIS GROUP REALTY, LLC (407-960-4545)

Listing Agent: Jay Lacourt (386-313-5008)

Remarks: Fully remodeled! One of the most competitively priced homes featuring over 3,300 SF, in the 32789 zip code, and in the K-8 Audubon Park School District. The K-8 Audubon Park School District is a small pocket, and ranked one of the best district's in the state. Fully remodeled luxury pool homes in the highly sought-after Audubon K-8 and Winter Park school district with over 3,300 square feet of exceptional living space, capped with a brand-new, architecturally stunning tile barrel roof that blends timeless Mediterranean elegance with lasting durability. 2614 Parkland Drive, a fully reimagined luxury residence in the heart of Winter Park. This is your chance to own a showpiece property with over 3,300 SF zoned for the coveted Audubon Park K-8 and Winter Park High School districts. Completely remodeled in late 2022, this home radiates warmth and sophistication. Solid light oak floors, custom railings, and an open-concept flow make entertaining effortless. The chef’s kitchen is a centerpiece; quartz counters, full-height designer tile, and abundant storage bring form and function together. Out back, discover your private resort. A heatable custom pool & spa finished in ultra-rare Caribbean blue tile sets the tone; elevated with two natural-gas fire pits, dramatic waterfalls, porcelain privacy walls, and a built-in grill. Every evening feels like a five-star escape.The first-floor master suite offers direct access to the outdoor oasis, while upstairs features three oversized bedrooms, a loft, and a private patio for sunset views. Brand-new tile roof, dual tankless water heaters, central vacuum, and all-natural gas appliances ensure low-maintenance, worry-free living. This is more than a home it’s a statement. A chance to live where luxury, location, and lifestyle converge.

Listing is courtesy of: JW GASTON LLC (321-239-5540)

Listing Agent: Ryan Gaston (321-239-5540)

Remarks: "MOTIVATED SELLER" - NEED SOME CLOSING COST? RATE BUY DOWN? WE CAN HELP GET YOU INTO THIS "MOVE-IN READY", 3-BED, 2-FULL BATHS, SINGLE FAMILY HOME WITH "NO HOA" & LARGE PRIVATE YARD, WINTER PARK, FL 32789. The Seller has already relocated and willing to work with a "Fully Pre-Qualified" Buyer to get this home sold quickly. AWESOME LOCATION just off Corrine Drive. WALKING DISTANCE to East End Market. TOP-RATED Audubon Park (K-8) & Winter Park High (Magnet Program) Schools. The Owners completed a HOME ADDITION & UPDATE in 2020 w/over $115,000.00 of improvements, including a NEW Roof, NEW Primary Bath, EXPANDED Great Room, NEWLY Enclosed Entry way w/mudroom & pantry, along with mechanical & finishing upgrades. Enter the home through a fully ENCLOSED FOYER which allows easy access to the new MUDROOM, as well as the ENORMOUS GREATROOM, which features an open Family & Dining Room area featuring a Wood Burning Fireplace, Decorative Shiplap Niche, Vaulted Ceiling and a dual French Doors leading to the HUGE Patio & Back yard. The CHEF'S KITCHEN was redesigned to include 42" Wood Upper & Lower SHAKER CABINETS w/Soft Close Drawers, Quartz Countertops, HUGE FARM-STYLE Deep Sink, Custom Tile Backsplash, "LG" Stainless Package including a French Style Refrigerator, Flat-Top Range, Microwave, Dishwasher, Wine Refrigerator, Decorative Shelves & a Mid-Century Modern Bungalow Pendant. The Primary Suite is the perfect COUPLES RETREAT which includes a Large Bedroom, Vaulted Ceiling, and a HUGE 14' LONG WALK-IN CLOSET w/Customizable Organizers to store all your Clothes & Accessories. The Primary Bathroom includes HIS & HERS Matching Vanities with Quartz Countertops, Recessed Sinks, Dual Mirrors & Hardware. Enjoy the luxury of a custom jetted soaking tub—ideal for unwinding after a long day or for families with young children, complete with a Tile Backsplash. The "WALK-IN SHOWER" features Frameless Glass, Custom Wall & Floor Tile and an OVERHEAD RAIN SHOWER. Finally, the bathroom features oversized 24"x24" Custom Floor Tile to complete the design features. Do you ENJOY OUTDOOR SPACE & like to Entertain? Do you need a SPACIOUS KIDS AREA for them to safely play? If so, you will FALL-IN-LOVE” with the fully fenced & enclosed back yard featuring two HUGE 12'x21' and 15'x27' OPEN PAVER PATIO areas perfect for all your outdoor furniture & equipment. Also enjoy your own PRIVATE TAVERN with an 8'x12' Bar designed with Corrugated Metal Panels, a Bar Top, Shelving & Concrete Floor. The Bar is OPEN FOR YOUR FRIENDS & FAMILY. The Backyard also includes (2) Separate Gate Entrances which will accommodate & secure your Boat, Trucks, Trailers, Work Equipment, etc. In addition, there is an 8'x8' and 5'x8' Storage Rooms. Addl Features: NEW Roof (2025), NEW Interior & Exterior Paint (2025), Tankless Water heater, Carrier HVAC System (2019), Updated Electric Panel (2019), Updated PEX Plumbing (2019), Newer 8"x36" Custom Tile Flooring, Newer Double Paned Windows (2019), NEW Drain field (2024), Block Construction, HUGE Laundry & Storage Room wCustom Organizers, 6" Baseboards, Window Treatments, Ceiling Fans & Lights, Open Carport (13'x21'), Covered Carport perfect for a Golf Cart (8'x17'), Irrigation System, Gutters & Downspouts, Decorative Bamboo & much more. Just minutes to Park Avenue, Fine Dining, Leu Gardens, Downtown Orlando, Municipal & OIA Airports, Hwy 436, 408, 418, Turnpike, UCF & the Beaches. Call for more info or to schedule your private showing.

Listing is courtesy of: ROCK SPRINGS REALTY, LLC (877-333-2811)

Listing Agent: Joel Bornstein (407-252-8092)

Remarks: Under contract-accepting backup offers. Welcome home to this darling, move-in-ready Winter Park gem! Perfectly suited as a starter home or investment opportunity, this beautifully remodeled 3-bedroom, 1-bath residence features laminate flooring throughout, a fully remodeled bathroom, and an updated kitchen with granite countertops and stainless steel appliances. Updated plumbing completed in 2014 and a 2017 AC system offer added peace of mind, and tasteful window treatments are already in place. Step outside to a large, fully fenced backyard complete with a fire pit and shed—perfect for entertaining, relaxing, or enjoying Florida evenings. Ideally located in a great area of Winter Park, close to shops, dining, and approximately 30 minutes to everything you want to enjoy in Orlando. One of the best-priced remodeled homes in the area—this charming property is a must-see! NO HOA! Tour this home at

Listing is courtesy of: BHHS FLORIDA REALTY (407-876-2090)

Listing Agent: Catherine Lambert Pa (407-908-2525)

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: You'll love this single-owner gem in Winter Park! Step inside to a traditional foyer, which welcomes you into a formal living room with excellent natural light and great flow into the dining room. Adjacent, you'll find the centrally located, spacious kitchen which overlooks your family room! A true split plan, the primary bedroom and oversized suite are on one side of the home and the two secondary bedrooms and hall bathroom are on the other. Out back, the real "heart of the home" is the generously sized back porch overlooking an original swimming pool! Solidly built block construction on a slab foundation, this 70s home will have you saying "they just don't make them like this anymore"! The major systems have been carefully updated over the years and the next owner will appreciate the peace of mind that a 2019 roof and 2018 HVAC system provide. The laundry is located in the two-car garage.

Listing is courtesy of: MILLER GRANT AND COMPANY (407-399-6031)

Listing Agent: Courtney Pelfrey (407-454-0538)

Remarks: Under contract-accepting backup offers. CALLING FOR HIGHEST AND BEST OFFERS BY MONDAY, APRIL 20th at 9:00 AM. Tucked away on a quiet street in the heart of Winter Park, this fully renovated 4-bedroom, 2.5-bath pool home—enhanced by fully owned solar panels—offers a rare blend of privacy, thoughtful design, and effortless indoor-outdoor living. Set on a generous ¼-acre lot, every detail has been curated to create a home that feels both elevated and family-friendly. Inside, the home opens to a flowing layout ideal for both everyday living and entertaining. Wide-plank luxury vinyl flooring, designer tile, and a soothing, modern palette create a cohesive sense of calm throughout. The kitchen is both a statement and a gathering place, featuring an oversized island wrapped in Taj Mahal quartzite, stainless steel appliances, and a custom wine bar—designed for connection, conversation, and celebration. Adjacent to the kitchen, the sunroom is a showstopper bathed in natural light and enhanced with custom built-ins, this versatile space effortlessly transforms into a home office, playroom, or entertainment lounge. This is where this home comes alive; perfect for large gatherings. The primary suite offers a serene retreat, highlighted by a fully remodeled spa-inspired bathroom with a soaking tub and a sleek, modern shower; inviting you to slow down and unwind. Outside, the newly added 800-square-foot turf play area, side yard, and green space surrounding the pool create room to play, entertain, and relax. The cul de sac and backyard feel exceptionally private, quiet, and peaceful. Just minutes from Park Avenue, you are surrounded by boutique shopping, acclaimed dining, lakeside strolls, and a lifestyle that feels both vibrant and relaxed. From morning coffee runs to evening walks under oak-lined streets, this is the essence of Winter Park living. This home is more than move-in ready—it’s a place to gather, grow and live. ROOF (OCT. 2022) HVAC (2017) WATER HEATER (2016) PLUMBING (2020) ELECTRICAL (UPDATED 2026) POOL PUMP/MOTOR (2020), POOL RESURFACED (2017) DRAIN SYSTEM: FRENCH DRAINS, SUMP PUMPS, GUTTERS (2024)

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

Listing Agent: Rebecca Bininger Junod (407-230-3650)

Remarks: This beautifully renovated Winter Park home feels warm, inviting, and easy to love. Bright natural light highlights a brand-new kitchen with modern appliances, a waterfall countertop, and soft wood finishes. Both bathrooms have been transformed with elegant marble look tile and spa style showers. You’ll fall in love with the large private backyard, perfect for summer barbecues, outdoor entertaining, play space, or even adding your own backyard oasis. All of this with no HOA and close to top rated Winter Park schools, popular dining, shopping, and parks. This move-in ready home offers lifestyle, comfort, and value you have to see in person, so schedule your showing today before it’s gone!

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

Listing Agent: Lesly Hijar (321-347-7383)

Remarks: This beautifully updated 4-bedroom, 2-bath bungalow with a 2-car garage sits on a quiet cul-de-sac and underwent a major renovation in 2023. Nearly every big-ticket item has been replaced, including the roof, A/C, water heater, and double-pane windows-giving you peace of mind for years to come. The home also features a fully updated kitchen with new cabinets, countertops, and a complete appliance package—refrigerator, dishwasher, range, range hood, and microwave—along with new carpeting, ceiling fans, and a new front door. Inside, the spacious family room includes custom built-ins, offering an abundance of storage. Both bathrooms have been tastefully remodeled. The primary bath features a beautiful walk-in shower and dual sinks, while the guest bath offers dual sinks, a jetted tub, a linen closet, and convenient access to the pool area. Step outside to an oversized, fully fenced backyard where you’ll find a sparkling screened-in pool and a large covered patio with an extended overhang—perfect for relaxing or entertaining year-round. And best of all…No HOA! Conveniently located minutes from Downtown Winter Park, key highways, shopping and within an hours drive of all the major theme parks and Orlando International Airport. Welcome Home!

Listing is courtesy of: REAL LIVING R E SOLUTIONS (407-253-1377)

Listing Agent: Lynn Roeder (407-758-8565)

Remarks: Welcome to 1177 Kenwood Ave, a home that blends warmth, comfort, and thoughtful design. The inviting living room features a cozy fireplace, creating the perfect space to relax on cooler evenings. The kitchen is designed with both style and function in mind, stainless steel appliances and a center island ideal for meal preparation and gathering. The spacious primary suite serves as a retreat, complete with a walk-in closet and an en-suite bathroom featuring dual sinks, and a separate soaking Jacuzzi. Step outside to enjoy the covered patio—perfect for entertaining or unwinding. The backyard a outdoor escape with a sparkling in-ground pool and a fenced area for added versatility. Inside, the home has been refreshed with new interior paint and partial flooring updates, giving it a clean, updated feel. Don’t miss the opportunity to make this beautiful property your next home. Included 100-Day Home Warranty with buyer activation

Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)

Listing Agent: Karen Albright (480-462-5392)

Remarks: This custom 2014-built Winter Park residence is stretched over a double lot with a backyard resort style retreat yet close to all Winter Park offers. A home with function and flexibility with a separate guest house, office or studio based on your needs. This thoughtfully designed home is sophisticated with casual comfort and showcases four bedrooms, 3.5 baths and nearly 3,800 square feet, downstairs main and additional guest suite, and upstairs includes remaining beds and baths. An inviting foyer welcomes you with volume ceilings, wood floors and a large transom window that allows beautiful natural light in. The family room is spacious with a marble wrap electric fireplace with lighting detail and niche for a flat screen TV. Clear glass doors across the back of the house lead you to the outside covered porch for ease of entertainment. The kitchen is open, light and bright with 42-inch shaker double stack cabinetry, large pantry and great workspace, a peninsula with bar seating as well as an eat-in kitchen area for large gatherings. Stainless appliances, granite counters and creative backsplash round it all out. The oversized laundry room includes an extra refrigerator and a second pantry for added convenience. The dining with tray ceiling, designer fixture and textured wallpaper add to the style of the home as well as dedicated office or flex space. Luxury continues into a primary suite with built-ins, large spa-like bath with sleek finishes, soaking tub, large dual-head shower and spacious walk-in closet. The primary suite overlooks backyard and opens to an outdoor oasis with open-air lanai with generous covered porch to gather or enjoy a night of alfresco dining. State-of-the-art modern resort-style pool with heated spa, sun shelf with fountain feature, a fire feature runs along edge of pool and transforms the backyard into a luxurious tropical oasis particularly at night. Hardscaping elements include pathways trimmed with turf grass, professional landscape lighting that enhances and elevates the home. Don’t wait to tour this special home in the heart of Winter Park, close to the best schools with Lakemont Elementary, Glenridge Middle and Winter Park High. A mile from Park Avenue, close to hospital and walkable to the YMCA, Phelps Park and fantastic restaurants.

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

Listing Agent: Alison Mosley (407-304-6458)

Remarks: Price reduction. Motivated seller! Welcome home to the prestigious community of Windsong in Winter Park. Upon entering this Toll Brothers-built home, you will notice no detail has been spared. Soaring ceilings greet you as you enter the foyer with elegant lighting. This 4-bedroom, 3.5-bath home is loaded with upgrades. The office features beautiful wood and detailed, custom bookshelves, complete with a double-door entry for added privacy. The formal dining room features a pass-through to the Butler's Pantry, which leads into a chef's oasis—Wolf stainless steel appliances for the serious chef, and solid surface countertops. The gourmet kitchen opens up to the family room. This home is a Great floor plan for entertaining friends and family. Eat in nook is located off the kitchen for dinners together. The primary suite is located on the first floor with a spa-like ensuite. Double vanity, extra-large shower, large bathtub for when a relaxing bath is just what you need after a long day. Upstairs, you will find a bonus room, as well as the remaining bedrooms. off the bonus room is a bedroom and a full bathroom, great for guests. The other two bedrooms and bathroom are located on the opposite side of the upstairs to create a split floor plan. Large backyard for enjoying the Florida weather. New EV charger in garage, new A/C unit. Home includes surround sound. This home features numerous upgrades, too many to list. Windsong community offers a resort-style pool with lake views, a playground, lake for fishing. Close to restaurants, schools, and shopping.

Listing is courtesy of: SELECTIVE REALTY GROUP LLC (407-627-1727)

Listing Agent: Shanon Luiz (407-247-2241)

Remarks: https://my.matterport.com/show/?m=o2WBZtN1TXm Welcome to Wrenwood Heights Community!! Very well Maintain Pool Home on CUL-DE-SAC LOT!! Great community with no HOA. House located on spacious large lot 0.31 Acre. House features Open Concept with 3 bedroom and 2 bathroom! New Roff 2024. Pool was resurfaced in 2025. Fully Fenced Backyard with upgraded Paver patio and mature landscaping and Fruit trees. Community located in Winter Park close to parks, shopping, dining and main highways. Seminole County schools! Call today to schedule your private showing!

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

Listing Agent: Nataliya Voroshylo Hylton (407-284-7247)