Winter Park Single Family Homes For Sale - 241 homes

Remarks: Tucked along one of Winter Park’s charming brick streets and positioned directly across from Lake Sylvan, this recently renovated residence unfolds like a quiet design story, one where character, craftsmanship and modern ease are aligned. From the moment you arrive, the home’s inviting curb appeal and reimagined cottage gardens set the tone, offering a sense of arrival that feels timeless and effortlessly refined. Inside, light pours through expansive picture windows, illuminating marble floors that flow seamlessly through the living room, dining area and kitchen. Every space has been thoughtfully curated by New York City–based interior designer Paulette Pascarella, where classic architecture is elevated by contemporary finishes and a restrained, sophisticated palette. The new kitchen serves as a centerpiece and a gathering space, featuring custom cabinetry, quartz countertops with a full-height backsplash and a high-end appliance suite anchored by a Bertazzoni refrigerator, equally suited for everyday living or intimate entertaining. Just beyond, the family room or den introduces warmth and texture with beautiful wood floors and custom built-ins designed for function and form. Motorized shades by The Shade Store, lighting by Visual Comfort and Currey, and hardware details by Buster + Punch are layered throughout the home, complemented by exquisite textile selections from Brunschwig, Schumacher, Thibaut, and Cowtan & Tout, each detail quietly reinforcing the level of thought and design intention behind the renovation. The second floor is a serene retreat and allows for elevated view of Lake Sylvan. The primary suite with soaring ceilings offers a generous window framing treetop views. The spa-inspired bath features a large glass-enclosed shower and a custom built-in dressing area, creating a private sanctuary that feels removed from the everyday. Two additional bedrooms, one with an en-suite bath, complete the upper level, offering flexibility for guests, work-from-home needs or extended stays. Outdoors, the grounds have been thoughtfully reimagined to evoke a cottage garden feel, providing a peaceful backdrop for morning coffee or evening strolls along the brick-lined street. The location is equally compelling, in a neighborhood known for its winding roads and timeless charm, just minutes from shopping, dining and cultural offerings of Park Avenue. Offering a lock-and-leave lifestyle, this home lives beautifully as a primary residence or as a second or third home and presents a compelling alternative to condominium or townhome living, where privacy, design and a desired Winter Park setting come together in one exceptional offering. There is potential for a third bedroom suite by converting the den/family room on the first floor as it is adjacent to a full bath.

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

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

Remarks: Timeless Olde Winter Park charm meets relaxed Florida living at 823 Granville Drive, a true Park Grove gem on an expansive 100' x 135' lot. Nestled among tree-lined streets in this coveted, well-established neighborhood, this single-story residence offers 4 bedrooms, 3.5 baths, and effortless indoor-outdoor living. Thoughtfully designed for entertaining, the home features two fireplaces that anchor inviting living and family spaces, creating a warm, elegant backdrop for gatherings large and small. The open, flowing layout keeps daily living convenient on one level while offering plenty of separation for guests or multi-generational living. Step outside to your own private retreat: a screened, enclosed pool area that feels like an outdoor living room, perfect for morning laps, weekend barbecues, or evening cocktails. The generous lot provides room to play, garden, or simply enjoy the lush surroundings and privacy Park Grove is known for. Practical features include a two-car garage, ample storage, and the rare opportunity to own a pool home in one of Winter Park’s most sought-after neighborhoods, just minutes to Park Avenue shopping, dining, lakes, and cultural venues. This is the Park Grove lifestyle—single-story, pool, charm, and location—all in one compelling property.

Listing is courtesy of: FLORIDA ONE REAL ESTATE LLC (407-599-7070)

Listing Agent: Anthony Consalvo (407-599-7070)

Remarks: One or more photo(s) has been virtually staged. NESTLED IN THE HEART OF HISTORIC WINTER PARK, THIS CHARMING RESIDENCE AT 518 SHOREVIEW AVE OFFERS TIMELESS CHARCTER. JUST STEPS FROM BEAUTIFUL LAKE KILARNEY. INSIDE, YOU WILL FIND STUNNING HARDWOOD FLOORS THAT ADD WARMTH AND ELEGANCE THROUGHOUT, ALONG WITH AN UPDATED PRIMARY BATHROOM FEATURING A RELAXING GARDEN TUB.THE INVITING FLORIDA ROOM PROVIDES THE PERFECT SPACE TO UNWIND OR ENTERTAIN WHILE ENJOYING THE NATURAL SURROUNDINGS. THE KITCHEN FEATURES A REVERSE OSMOSIS SYSTEM TO FILTER THE DRINKING WATER. THIS PROPERTY IS A RARE OPPORTUNITY TO OWN A PIECE OF WINTER PARK HISTORY IN AN UNBEATABLE LOCATION NEXT TO FABULOUS SHOPPING AND DINING EXPERIENCES. ** SELLER HAS PLANS FOR ATTIC EXPANSION AVAILABLE.

Listing is courtesy of: UNITED REAL ESTATE PREFERRED (407-243-8840)

Listing Agent: Kendra Wallace (407-457-7069)

Remarks: Winter Park “Sweet Spot”, Priced to Sell: Rare 3/2 Opportunity in Eastbrook Discover the perfect blend of value, location, and versatility in Winter Park’s highly sought-after Eastbrook neighborhood. This 3-bedroom, 2-bathroom home is ideal for homebuyers looking to make new memories or savvy investors seeking a turn-key property. Move-in Ready: From the moment you step inside this roomy, open floor plan, it’s ready to enjoy. The heart of the home—kitchen, dining and living room—is tastefully renewed and has plenty of space. The ample primary bedroom has a full ensuite bathroom and large windows. Two additional bedrooms share a full guest bathroom. Recent functional improvements provide peace of mind: new water heater, window blinds and exterior paint, and a 12-year-old insurable roof. Outdoor enthusiasts will love the massive, fully fenced backyard, including firepit for chilly (yes, chilly!) Florida nights and “grass-covered” patio. This private oasis is ready for pets, play, or future expansions. BONUS exterior features include carport and multicar driveway, large separate laundry room, lots of elevated carport storage, and an additional cross-fenced and gated side yard. Under Market Value for Quick Sale: Motivated sellers + a price well below area comparables = a win-win. Investor Advantage: This property currently serves as a high-performing, low-maintenance rental with risk-free reliable tenants. In May, renew the lease for continued cash flow or transition the home to a primary residence when the lease expires. • Location: Quiet, safe, and walkable Eastbrook, with shopping less than a mile away. • Condition: Well-maintained with modern updates. • Inclusions: Everything in the home conveys with the sale (excluding tenant furnishings). • Value: Instant ROI for investors and equity potential—priced to move fast! Don’t miss your chance to own a piece of Winter Park at an unbeatable price. Schedule your showing today!

Listing is courtesy of: SAVVY AVENUE, LLC (888-490-1268)

Listing Agent: Moe Mossa (888-490-1268)

Remarks: Under Construction. Spectacular new LUIH Luxury Home in the heart of Winter Park! Clean architectural lines, a bold façade, and curated exterior detailing set the tone for what unfolds inside. Beyond the entry, the home opens into a dramatic, light-filled living space featuring a sleek electric fireplace, framed by custom built-ins with ambient LED underlighting, while a glass-enclosed wine display serves as a stunning architectural detail. The kitchen is a true centerpiece, designed to impress at every level. Outfitted with a full suite of premium Thermador appliances, striking Calacatta quartz countertops, custom cabinetry, and a spacious walk-in pantry. Privately positioned, the primary suite is a sanctuary of calm and sophistication. The spa-inspired bath evokes a boutique hotel experience, featuring floating mirrors, a freestanding soaking tub, an expansive glass-enclosed walk-in shower, and refined finishes that create a sense of understated luxury. The custom walk-in closet is equally impressive, offering both scale and thoughtful organization. A rare and highly sought-after feature in Winter Park, the home offers two bedrooms on the first floor, ideal for guests. Upstairs, a spacious loft creates an additional living area perfect for relaxing or entertaining, complemented by a dedicated office and three generously sized bedrooms. The outdoor living experience is nothing short of amazing. As you step through the expansive sliders, the interior flows seamlessly to a covered lanai designed for true indoor-outdoor living. A fully equipped summer kitchen anchors the space, ideal for hosting, while the expansive backyard is transformed into a private retreat with a sparkling pool and spa, offering both tranquility and the perfect backdrop for entertaining. Perfectly positioned for the Winter Park lifestyle, you’re a short golf cart ride from the shops and dining of Park Avenue, with Cady Way Park, the YMCA, and Winter Park Village also just moments away. In a market where true quality is rare, this residence stands apart, an exceptional blend of design, craftsmanship, and livability that defines what luxury should feel like in Winter Park.

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

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

Remarks: This home sits at the end of a cul-de-sac with an attractive courtyard entry to the 2 car garage. The Kitchen has been updated with new cabinets and tile flooring and the baths all have been remodeled and have tile flooring. The remodeled Primary Bedroom has Luxury Vinyl Flooring. The house has had all the windows and front door replaced. The screened porch overlooks a spacious fenced backyard that includes a block building (summer cottage) with electric and plumbing that is currently being used for storage. The Roof was replaced in 2022 and the yard has a sprinkler system. Make an appointment to see today!!

Listing is courtesy of: RE/MAX 200 REALTY (407-629-6330)

Listing Agent: Diane Gerry Pa (407-405-5550)

Remarks: Experience elevated living in this fully transformed luxury residence in the heart of Winter Park, where design, premium finishes, and effortless functionality come together seamlessly. This 3-bedroom, 3.5-bath pool home offers approximately 2,400 square feet of impeccably curated living space, designed for those who appreciate both style and substance. Expertly designed by Morrone Interiors, every detail reflects a refined, cohesive aesthetic. Step inside to warm oak wood floors and a light-filled open-concept layout ideal for both everyday living and upscale entertaining. The chef’s kitchen is a true statement, featuring custom oak cabinetry, sleek quartz countertops with a dramatic waterfall island, and an expansive breakfast bar. Top-of-the-line appliances include a Sub-Zero refrigerator, Wolf 6-burner gas professional range with grill and double ovens, Wolf microwave, Miele dishwasher with PowerDisk system, and a built-in Miele coffee station. The kitchen flows effortlessly into both a breakfast nook and a separate dining area, while the designer bar serves as a stunning focal point—complete with two Sub-Zero dual zone wine refrigerators accommodating more than 200 bottles, along with additional Sub-Zero refrigerator and freezer drawers. Downstairs all blinds are motorized and have gorgeous custom drapes. Upstairs, all three bedrooms are en suite, offering a private retreat for family and guests. A versatile loft area features a custom-designed laundry space concealed behind built-in cabinetry for a clean, streamlined aesthetic. One bedroom has been thoughtfully designed as a home office with a built-in Murphy bed, providing flexibility without compromising luxury. The outdoor space is equally refined, featuring low-maintenance turf, a beautifully designed pool, and a covered lanai perfect for relaxing or entertaining. A built-in grill area and lush privacy hedging create a serene backyard oasis, with landscaping professionally designed and maintained by Signature Landscaping. Additional highlights include a 2-car garage and a Sonos sound system in the living room and lanai, enhancing the home’s elevated lifestyle experience. Most furnishings are available for purchase separately, offering a truly turnkey, designer-furnished opportunity. Ideally located just minutes from Park Avenue, top-rated schools,Rollins College, fine dining, and boutique shopping, this exceptional home represents the very best of Winter Park luxury living. Perfect lock and leave home with the perfect location!

Listing is courtesy of: OLDE TOWN BROKERS INC (407-425-5069)

Listing Agent: Noelle Leblanc (407-491-2744)

Remarks: Grand Southern charm and architectural elegance define this stately residence in one of Winter Park’s most desirable neighborhoods, set along a quiet brick-lined street just steps from Lake Chelton. Positioned on nearly half an acre, the home spans over 5,200 square feet, offering 5 bedrooms, 4.5 baths, a designated office, a large, versatile media/game room, a 3-car garage, and an expansive lanai with summer kitchen and resort style pool— all brought together in a smart well-planned layout ideal for effortless everyday living and exceptional entertaining. Step inside to a beautifully curated interior where rich architectural detail and livable design come together. Extensive custom millwork—seen in detailed moldings, trim work, and built-ins—adds depth and character throughout. The entry opens to gracious living and dining spaces, complemented by an impressive 550+ bottle temperature-controlled wine room. At the heart of the home, a beautifully appointed Kitchen, featuring white wood cabinetry, a six-burner gas range, an oversized quartz island, and a delightful breakfast nook that seamlessly connects to the family room featuring custom built-ins and fireplace—creating a natural gathering space. Tucked away, the first-floor primary suite offers a spacious sitting area, a beautifully customized closet with dressing area, and a luxurious bath with marble flooring, a large double-head walk-in shower, dual vanities, a free -standing tub, and built-in linen cabinetry—designed as a calming and private sanctuary. The first level also features a private guest bedroom with en-suite bath, creating an ideal setup for friends & family. A generously sized laundry room offers abundant cabinetry and exceptional storage, making everyday tasks feel effortless. Upstairs, three spacious bedrooms and two full baths provide comfortable accommodations, with two bedrooms opening through French doors to the front double balcony—perfect for enjoying peaceful treetop views. The back of the home unfolds around a beautiful pool and spa, with French doors from multiple rooms opening to the lanai and creating a natural indoor-outdoor connection. Retractable screens allow for year-round enjoyment of the well-appointed summer kitchen, making it ideal for both relaxed evenings and easy entertaining. Other notable highlights: a whole house natural gas generator, extensive brick paver driveway & motor court, automated driveway gate, integrated sound system, security cameras and new roof 2024. Lastly, this profound property offers top rated Winter Park schools and easy access to Park Ave, Downtown Orlando, Audubon Park Garden District and Baldwin Park.

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

Listing Agent: Mary Colton (407-222-7388)

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: A New Standard of Modern Sophistication in Winter Park In a city known for its heritage, this ground-up architectural renovation emerges as a bold statement of modern luxury. Located within one of Winter Park’s most coveted enclaves, this four-bedroom, five-bathroom residence is not merely a place to live, but a meticulously crafted experience where high-design meets intuitive living. Step through the striking 10-foot glass pivot doors into a world defined by light and scale. The soaring foyer gives way to an expansive open-concept floor plan, where the boundary between indoors and out begins to blur. Sleek Italian wood flooring guides you through the main level to the heart of the home: a grand living area anchored by a statement fireplace. It is a space designed for the quiet morning coffee just as much as the vibrant evening gala. A Symphony of Intelligence. This home lives and breathes with you. Equipped with a fully integrated Control4 automation system, the environment responds to your touch. From your device, you can orchestrate the perfect atmosphere—adjusting custom lighting scenes, streaming high-fidelity music, or setting the climate before you even arrive. This "invisible concierge" extends to the water’s edge, allowing you to manage pool temperatures and lighting with effortless precision. The kitchen is a masterclass in culinary elegance, blending European minimalism with professional-grade power. Light-toned cabinetry hides clever storage solutions, while premium Sub-Zero and Wolf appliances sit beneath striking Neolith double countertops. It is a space that invites creativity, whether you are hosting an intimate chef-led dinner or enjoying a slow Sunday brunch. The commitment to "pride of ownership" is felt most deeply in the private quarters. Each of the four bedrooms is a dedicated en suite retreat, featuring voluminous walk-in closets and spa-inspired baths. Custom vanities, Neolith surfaces, and soft, indirect lighting create a hotel-level sense of calm, ensuring every guest or family member feels a sense of total seclusion. The Backyard Resort. The transition to the outdoors is seamless, revealing a private oasis designed for the quintessential Florida lifestyle. A Brazilian IPE wood deck surrounds a shimmering, heated mini-pebble pool in French gray. Beyond the water, the lushly landscaped grounds lead to a premier summer kitchen clad in sintered stone. Here, under the Florida stars, the integrated grill and sink provide the ultimate setting for al-fresco entertaining. Experience the pinnacle of Winter Park living. You are situated just moments from the refined energy of Park Avenue, the prestigious Interlachen Country Club, and the scenic beauty of Phelps Park. With zoning for the area’s top-rated schools the location is as strategic as it is beautiful. Notable Refinements: • Whole-home generator ensuring absolute peace of mind. • Finished garage floors and a circular driveway accented with salt and pepper gravel. • Full-home Control4 integration for music, light, and climate. Experience the art of living well—connect with us today for an exclusive private tour **Unique financial opportunities available: The seller is open to owner financing and Bitcoin (Digital Asset/ Crypto) as a medium of exchange. Please reach out to discuss how we can facilitate a transaction tailored to your needs.**

Listing is courtesy of: ROI AVE LLC (321-663-7276)

Listing Agent: Mark Anthony Buot (407-925-1716)

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: 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: 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: 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: 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)