Homes for Sale Near Winter Park High in Winter Park - 164 homes

Remarks: JUST COMPLETED....WINTER PARK / LAKE SUE DISTRICT — A TRUE STANDOUT IN TODAY’S LUXURY NEW CONSTRUCTION MARKET Proudly presented by RARE Builders, a name synonymous with design-forward custom homes that continue to help set and raise the standard in Orlando and Winter Park, this newly completed residence represents a rare opportunity to secure a fully realized custom home in one of the area’s most sought-after neighborhoods. Positioned just steps from Lake Chelton and Lake Sue, and located within a highly desirable Winter Park school district, the setting delivers an exceptional lifestyle in one of Central Florida’s most dynamic and tightly held areas. While new construction inventory exists in today’s market, this home stands apart offering a fresh, cutting-edge architectural vision brought to life through exceptional planning, material selection, and execution. Prominently sited on an elevated homesite with a striking front elevation, the home offers 4,500 square feet of living space, including nearly 3,000 square feet on the ground level alone... a rare and highly functional configuration. The layout is both expansive and intentional, featuring multiple large living spaces, a private ground-floor primary suite, and a well-appointed guest suite/study/flex space. Upstairs, each bedroom is thoughtfully designed with either an en-suite bath or direct access to a full bath, delivering both comfort and privacy throughout. The defining feature of this home...and one rarely seen in the market... is the massive Renlita Floataway door system, which opens an entire wall of the home to seamlessly connect the interior Florida room with the resort-style outdoor living environment. This creates a true four-season entertaining space, transforming the way the home lives and offering a level of indoor-outdoor integration that is both dramatic and highly functional. The outdoor setting is designed as a private resort, complete with a pool, spa, fire and water features, pergola, and summer kitchen... all curated to complement the home’s architectural vision. Inside, the level of finish and design is exceptional. From breathtaking Venetian plaster walls to a dramatic two-story foyer, the home is defined by a refined and highly curated selection of materials, fixtures, and hardware. Every element has been intentionally sourced and executed, resulting in a level of craftsmanship and aesthetic cohesion that is rarely achieved and immediately recognized by discerning buyers. A well-appointed kitchen with walk-in butler’s pantry and thoughtfully designed secondary spaces further enhance both function and livability. Integrated Control4 home automation, audio, and security systems complete the offering. Located just minutes from Downtown Orlando, Winter Park, Park Avenue, Winter Park Village, AdventHealth, and Orlando Health, this home delivers a rare combination of location, design, and execution at the highest level. This is not simply new construction, it is a distinct, design-driven custom residence offering a level of detail, presence, and livability that is truly rare in the current Winter Park market.

Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)

Listing Agent: Robert Kurzreiter Pa (407-476-4156)

Remarks: Exquisite new construction in the heart of Winter Park, this LUIH Luxury Homes residence distinguishes itself through refined design, thoughtful efficiency, and an elevated level of craftsmanship. From the moment you enter, the home reveals itself with deliberate intention, clean architectural lines and a light-filled, open-concept layout create an effortless flow throughout. The main living space is both sophisticated and inviting, anchored by a sleek electric fireplace and expansive pocketing glass doors that gracefully blur the line between indoor and outdoor living. At the heart of the home, the chef’s kitchen is as striking as it is functional. Adorned with Calacatta quartz countertops and a full suite of premium Thermador appliances, it is designed to accommodate both everyday living and elegant entertaining. The kitchen transitions seamlessly into the dining area, while a walk-in pantry, generously sized mudroom / laundry space, and wine cellar add layers of convenience and luxury rarely found in homes at this price point. The primary bedroom suite offers a true sanctuary with direct access to a secluded outdoor patio that provides a serene extension of the space. The spa-inspired bath showcases a freestanding soaking tub, dual vanities, and an expansive walk-in shower. Upstairs, four additional bedrooms offer generous proportions and versatility, ideal for guests, family, or tailored uses such as a home office or fitness studio. Designed for year-round enjoyment, the outdoor living experience is equally captivating. A sprawling covered lanai features a fully equipped summer kitchen with grill, sink, and beverage refrigerator, overlooking a meticulously designed backyard complete with a resort-style pool and spa, perfect for both intimate evenings and grand entertaining. All of this is ideally located just moments from the boutiques and dining of Park Avenue, with convenient access to Phelps Park and the Winter Park YMCA, placing you at the center of one of Central Florida’s most desirable lifestyles.

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

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

Remarks: Welcome to this fully remodeled, move-in ready home in the highly sought-after Winter Park area! This beautifully updated single-story residence features 4 bedrooms and 2 bathrooms, offering comfortable living with a bright and inviting layout. Step inside to discover a bright, open floor plan with modern finishes and thoughtfully updated living spaces, designed for both comfort and functionality. The home offers spacious bedrooms, stylish upgrades, and a fresh contemporary feel throughout, making it perfect for families, first-time buyers, or anyone seeking a turnkey property. Step outside to an expansive backyard featuring a beautiful pool, creating the perfect space for relaxing, entertaining, and enjoying Florida living year-round. The large outdoor space offers endless possibilities to customize the backyard your way—whether it’s adding an outdoor kitchen, lounge area, garden, or entertainment space to create your dream outdoor oasis. Located in a quiet, established neighborhood within an A+ rated school zone, this home also offers convenient access to top shopping, dining, parks, and major highways, making commuting and daily errands a breeze. Don’t miss this incredible opportunity to own a fully remodeled home with a pool in one of the most desirable areas of Winter Park.

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

Listing Agent: Bernardo Carrasquel (407-920-4973)

Remarks: A masterfully crafted custom residence in the heart of Winter Park, this 2014 Barefoot Brothers home blends timeless architecture with modern functionality just moments from Park Avenue and the Audubon Park Garden District. Designed for both refined entertaining and active everyday living, this 5-bedroom + office home offers a flexible, family-focused floor plan plus an expansive second floor bonus room, ideal for recreation, media, or study. A formal dining room and oversized great room with 11.5’ ceilings create the perfect balance of comfort and sophistication. The first-floor primary suite features a private, attached office space and a spa-inspired ensuite with marble floors, marble-topped double vanity, freestanding cast iron soaking tub with gooseneck filler, double walk-in shower, Kohler fixtures, and a statement chandelier over the tub. The chef’s kitchen showcases marble countertops, a walnut center island, a large walk-in pantry, 10’ ceilings, GE gas range, new Samsung refrigerator, and Bosch dishwasher — all opening seamlessly to the living area anchored by a gas fireplace with custom built-ins and double French doors leading outside. Designed with connection in mind, the breezeway links the main home to the detached garage and opens to a charming river rock paved patio — perfect for gatherings and outdoor dining. A recently repainted timber-framed front porch welcomes guests with timeless curb appeal, complemented by a circular driveway, irrigation system, and landscape lighting. Built with longevity and energy efficiency in mind, this home features insulated concrete form (ICF) construction, vinyl double-pane Low-E windows, two tankless water heaters, natural gas connections (fireplace, range, dryer, outdoor grill), Cat 6 ethernet wiring, surround sound, and ceiling fans throughout. Spend your mornings biking to coffee in Audubon Park and your evenings enjoying dinner on the Park Avenue — all while coming home to a thoughtfully constructed retreat designed for modern family living. With roof, electrical, and plumbing completed in 2014, this home offers peace of mind, architectural character, and an exceptional lifestyle in one of Winter Park’s most desirable corridors. Schedule your private showing today!

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

Listing Agent: Jill Healey (407-797-1420)

Remarks: "Open the Doors to Your Dreams" of owning an Affordable Home with a pool in Winter Park. The home features a Spacious Kitchen with Upgraded Cabinets, and stone countertops; Primary bedroom suite is amazing. You will love the layout and upgraded primary bathroom; Beautiful Porcelain tile flooring throughout the home; Large family room with fireplace; Large screened back porch/LANAI. And there is an inground pool in the back yard. You will enjoy entertaining in this home featuring a gourmet kitchen with granite countertops, and stainless steel appliances. This property may qualify for Seller Financing (Vendee). If property was built prior to 1978, Lead Based Paint Potentially Exists. Come tour this home today. We expect this one to sell quickly.

Listing is courtesy of: WEATHERSPOON REALTY INC (407-878-4468)

Listing Agent: Eugene Weatherspoon (407-878-4468)

Remarks: Timeless Elegance Meets Modern Luxury in Winter Park's Most Coveted Location Discover an extraordinary residence where exceptional craftsmanship and sophisticated design converge at 948 Poinciana Lane. This meticulously reimagined estate represents the pinnacle of refined living in one of Winter Park's most prestigious neighborhoods, offering an effortless blend of classic architecture and contemporary luxury. From the moment you step through the elegant foyer, you're greeted by sun-drenched interiors showcasing gleaming hardwood floors, soaring coffered ceilings, and designer details at every turn. The thoughtful floor plan reveals a private home office with custom built-ins and fireplace to the right, and a gracious formal dining room to the left—perfect for hosting memorable gatherings. The heart of this home is the spectacular kitchen, a true chef's masterpiece featuring custom cabinetry, pristine marble countertops, statement pendant lighting, and top-tier appliances. This culinary haven flows seamlessly into the light-filled family room, where expansive windows frame views of your private outdoor sanctuary. The first-floor primary retreat is a haven of tranquility, featuring an expansive walk-in dressing room with exceptional storage and a spa-inspired ensuite bath. Luxuriate in the freestanding soaking tub, refresh in the walk-in shower, or prepare for your day at the generous double vanity—all appointed with elegant finishes befitting this caliber of home. Three generously proportioned guest bedrooms upstairs offer optimal comfort and privacy, complemented by a Jack-and-Jill bath and additional hall bath. A spacious bonus room with backyard views provides versatility for a media room, playroom, or home gym. Above the garage, an additional 260-square-foot bonus room with wet bar and wine fridge creates the ideal entertainer's lounge or game room. Step through French doors to your private resort-style backyard—a meticulously landscaped oasis featuring a sparkling pool and spa surrounded by lush greenery, stately palms, and thoughtful lighting. Whether gathering around the firepit, lounging poolside, or dining alfresco under the stars, this outdoor retreat elevates everyday living to an art form. No detail has been overlooked in this complete renovation: designer light fixtures and custom window treatments throughout, first-floor laundry convenience, elevated trim and baseboard, fresh paint, recessed lighting, and three HVAC units ensuring year-round comfort. The location is simply unparalleled—a leisurely stroll to the Winter Park Racquet Club, zoned for A-rated public schools, and just moments from the world-renowned shops and restaurants of Park Avenue. This is more than a home; it's a lifestyle of distinction in Central Florida's most desirable address.

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

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

Remarks: In the heart of Winter Park, 1150 Via Salerno is a newly completed Mediterranean-minimalist residence that blends architectural refinement w/ organic warmth. Now offered at a newly adjusted price, the home presents a compelling opportunity to experience design-forward new construction in the Vias neighborhood. Developed and designed by Steve & Jodie Warrick Konold of Scout & Co., the 3,850-sf layout offers 4 bedrooms & 5.5 baths, wrapped in the intentional privacy of a luxury retreat. Beyond its terraced walkway & garden courtyard—envisioned in collaboration w/ architect Cynde Norris—French antique gates open to a native-planted entry garden, creating a soft transition to the interior. A glass foyer introduces a tongue-and-groove ceiling & woven rattan chandelier, sourced & designed in London, leading to a sculptural stairwell positioned just off the main living spaces. The great room features soaring ceilings, a sleek fireplace & walls of glass windows & doors that blur the boundary between inside & out. Ten-inch baseboards meet level 5 drywall in a clean reveal, paired w/ micro-crete flooring on the main level & wide-plank European oak upstairs. In the kitchen, materials w/ function are elevated w/ a Thermadore dual-fuel range, custom plaster hood, full refrigerator & freezer columns & a large island topped in honed black quartzite. The surrounding cabinetry is crafted from hand-carved V-groove panels w/ soft-close hardware & integrated pullout storage. Caesarstone surfaces run along the perimeter while steel-and-glass open shelving w/ a sculptural black sconce balance the composition. A vintage chandelier from Prize Home & Garden sourced in Round Top completes the room. The primary suite occupies a private wing on the main floor accessed via antique gallery doors that lead to the rear courtyard. Vaulted ceilings, a custom walk-in closet w/ a spa-like bath provide a luxurious retreat. Features include a long double vanity, matte black Kohler fixtures, a freestanding tub, walk-in shower w/ built-in bench & separate water closet. On the mezzanine level, the powder bath makes a dramatic statement w/ a floating black quartzite trough sink w/ handwoven mirror. Across the hall, the laundry room blends beauty w/ utility w/ custom cabinetry, matching quartzite surfaces, matte black fixtures & a side-by-side front-load washer & dryer. A nearby guest suite is marked by an antique door entry. The en-suite bath features a hand-painted tile threshold & suede-framed mirror. Two upstairs bedroom suites feature en-suite baths, designer lighting, distinctive mirrors & continuous European oak flooring. Positioned at the front of the home, the rooftop terrace is accessible via the upper hallway. The detached casita opens to the pool courtyard through accordion glass doors & features micro-crete floors, a woven rattan chandelier & a full bath—ideal as a studio, gym or office. Outdoor spaces include two garden courtyards, a fully fenced backyard, a heated saltwater pool & a rooftop terrace, all enclosed by masonry walls & a board-on-board privacy fence. Additional features include a lower-level two-car garage, storage closet, 3 HVAC systems, Rinnai tankless water heater, Sierra Pacific windows, customized closets, solid core interior doors, 6” round gutters & a Barcelona barrel tile roof. Thoughtfully designed & beautifully executed, 1150 Via Salerno offers a refined lifestyle tucked within one of Winter Park’s most exclusive enclaves.

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

Listing Agent: Padgett Mccormick (407-645-4321)

Remarks: Exceptional design meets refined luxury in this brand-new architectural masterpiece by DaVinci. This 5 bedroom, 6.5 bath home offers over 4,500 square feet of bright, open living space designed for both comfort and functionality. Enter through your custom glass front door into the foyer leading to your main living area featuring a fireplace and sliding glass walls for indoor-outdoor living. This flows effortlessly into a gorgeous gourmet kitchen with high-end appliances featuring a Wolf range, Sub-Zero refrigerator, Euro-style cabinetry, oversized island, and walk-in pantry. The downstairs primary suite overlooks the pool and includes a spa-like bath with soaking tub and rain showers. An additional ensuite bedroom on the first floor works perfectly as a guest room or office. Upstairs you’ll find a large loft and media area with private balcony, along with three ensuite bedrooms including walk-in closets. Step outside and enjoy year-round living under the covered lanai featuring a summer kitchen overlooking the saltwater pool surrounded by mature landscaping. An outdoor bath adds extra convenience, and the oversized lot provides abundant space to relax, entertain or dine al fresco. This home comes complete with a spacious three-car garage with EV charging. Minutes to Interlachen Country Club, Winter Park Racquet Club, and Park Ave shopping. Don’t miss this beautiful custom modern home in one of Winter Park’s most sought-after neighborhoods! Ask about the new landscaping package, and driveway installation.

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

Listing Agent: Tab Bish Llc (855-450-0442)

Remarks: Under contract-accepting backup offers. Excellent opportunity to renovate existing home or build your dream home in Winter Park. Mid-Century Modern on 10,278 SqFt corner lot. Home being sold AS-IS. Updated roof & HVAC. Zoned for Lakemont, Maitland Middle, Winter Park High. Centrally located near restaurants, shopping, Winter Park Hospital & a short drive to Park Avenue, Rollins College & many local parks.

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

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

Remarks: One or more photo(s) has been virtually staged. This home can be purchased with NO INCOME VERIFICATION needed! Welcome to 720 W Webster Avenue, a beautifully renovated home in the heart of historic Carver Town in Winter Park—one of the most sought-after locations in Central Florida. Just a short walk to downtown Winter Park, this charming residence blends modern updates with timeless character while offering the lifestyle people move here for. This 3-bedroom, 2-bathroom home contains 1,356 square feet of thoughtfully updated living space designed for both comfort and style. From the moment you step inside, you'll notice the clean, modern feel created by zero carpet throughout the entire home, giving every room a fresh, cohesive look while making maintenance simple and practical. At the center of the home is the fully updated kitchen, featuring beautiful granite countertops, ample cabinetry, and a functional layout perfect for everyday living or entertaining guests. The kitchen serves as the heart of the home, separating the spacious living room from the formal dining room, creating a natural flow between gathering spaces while maintaining distinct areas for relaxing and hosting. Both bathrooms have been fully renovated, showcasing modern finishes that complement the home's updated aesthetic. Each bedroom offers comfortable space, natural light, and flexibility for a primary suite, guest room, or home office. Convenience continues with the laundry closet featuring a newer stackable washer and dryer, maximizing space while keeping everyday tasks simple and efficient. Step outside and you'll find a fully fenced backyard, providing privacy and plenty of room for pets, outdoor gatherings, or simply enjoying Florida’s beautiful weather. The property also includes an oversized covered carport, offering generous parking and protection from the elements. For electric vehicle owners, the carport is already equipped with a Tesla charger, making daily charging effortless and future-ready. What truly sets this property apart is its unbeatable location. Situated in historic Carver Town, you're just minutes from the charm and vibrancy of downtown Winter Park. Enjoy easy access to Park Avenue’s award-winning restaurants, boutique shopping, art galleries, and cultural attractions. Spend weekends exploring the Winter Park Farmers Market, taking a scenic boat tour on the Winter Park Chain of Lakes, or strolling through Central Park’s shaded oak-lined paths. Whether you're looking for a primary residence, a stylish Winter Park retreat, or a home close to everything that makes this city special, 720 W Webster Avenue delivers the perfect combination of location, updates, and lifestyle. Opportunities to own a fully renovated home this close to downtown Winter Park are rare. Schedule your private showing today and experience everything this exceptional property and location can provide!

Listing is courtesy of: SERHANT (646-480-7665)

Listing Agent: Vincent Cordaro (631-834-0816)

Remarks: Under contract-accepting backup offers. Welcome to 851 Miles Ave #13, a beautifully renovated 2-bedroom, 1-bathroom second-floor condo in the heart of charming Winter Park, FL 32789! Meticulously updated since 2023, this home blends modern luxury with effortless comfort and is truly move-in ready. As you step inside, you’ll be greeted by elegant porcelain tile flooring throughout—offering both durability and a look that’s easy to maintain. The heart of the home, the kitchen, has been completely reimagined with sleek granite countertops, fresh cabinetry, and contemporary finishes that make cooking and entertaining a joy. The bathroom has also received a full renovation, featuring granite countertops and updated fixtures that enhance both style and function. With thoughtful design at every turn, this condo feels fresh, bright, and uniquely yours. Situated on the second floor for added privacy and natural light, this unit provides a peaceful retreat while still being close to all that Winter Park has to offer. Enjoy being minutes from Park Avenue, with its array of boutique shopping, acclaimed restaurants, art galleries, and outdoor markets. Explore scenic parks, lakeside boat tours, cultural attractions, and community events that make Winter Park one of Central Florida’s most desirable places to live. Whether you’re searching for your next home or an exceptional investment opportunity, 851 Miles Ave #13 showcases stylish updates, quality finishes, and a location you’ll love. Don’t miss your chance — schedule a showing today!

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

Listing Agent: Eric Campbell (321-279-8941)

Remarks: Welcome to this beautifully maintained 2-bedroom, 2-bathroom first-floor corner-unit condo in Winter Park, offering comfort, convenience, and peace of mind, with major updates completed in 2026. These upgrades were specifically implemented to enhance the property's aesthetic appeal and energy efficiency. The exterior updates include replacing all windows with single-hung, double-pane, low-E glass vinyl units and installing a matching vinyl sliding patio door. Interior improvements include new interior and closet doors, 5" baseboards, and fresh paint on all ceilings, walls, and trim. Additionally, all ceilings have been modernized to a smooth finish, and 2" cordless faux-wood blinds have been installed throughout. Both bathrooms have been fully renovated with new flooring, wall tiling, tubs, toilets, vanities, and updated fixtures. The kitchen has also been completely transformed with new cabinetry, granite countertops, a modern faucet, and a full suite of stainless steel appliances. Located near the University of Central Florida, Full Sail University, and SR-417, this condo offers quick access to major commuting routes, shopping, dining, and everyday essentials. Whether you're looking for a primary residence or a long-term investment opportunity, this property combines location, functionality, and value in one of Orlando's most connected areas.

Listing is courtesy of: ANNE ROGERS REALTY GROUP INC (407-649-4141)

Listing Agent: Reza Shirzad (407-234-1515)

Remarks: One or more photo(s) has been virtually staged. Introducing 250 Cortland Ave — a refined expression of Winter Park living, ideally positioned on one of the area’s most picturesque brick-lined streets, surrounded by established luxury homes and mature canopy trees. From the moment you arrive, the home exudes a quiet sophistication, with manicured, low-maintenance landscaping and a sense of privacy that carries throughout the property. An oversized two-car garage and thoughtfully designed exterior set the tone for what awaits inside. Step through the entry and into a light-filled interior where volume ceilings and an open-concept layout create an immediate sense of space and flow. The home is designed to draw your eye outward — through expansive living areas, beyond the enclosed lanai, and into the serene pool and spa, creating a seamless connection between indoor and outdoor living. Every detail has been carefully curated to balance warmth and modern refinement. Rich Brazilian rosewood flooring anchors the main living spaces, while durable quarry tile provides both style and functionality in the kitchen and transitional areas. The kitchen itself has been reimagined with updated cabinetry and modern appliances, offering a clean, sophisticated space that remains highly functional for everyday living and entertaining. The split floor plan provides both comfort and privacy, with a spacious primary suite and well-appointed secondary bedrooms. Both bathrooms have been tastefully updated with contemporary finishes, while additional enhancements throughout the home — including updated lighting, hardware, flooring, and fresh interior touches — contribute to its move-in-ready appeal. Designed for the Florida lifestyle, the home truly comes to life when the expansive sliding glass doors are opened, blending the interior with the screened outdoor living space. The pool and spa become a natural extension of the home — perfect for quiet mornings, entertaining guests, or simply enjoying the year-round sunshine in complete privacy. Located just moments from Lake Mizell, part of the highly sought-after Winter Park Chain of Lakes, the property offers not only a beautiful home, but a lifestyle defined by scenic surroundings, walkability, and timeless charm. 250 Cortland Ave is more than a home — it is a rare opportunity to own a thoughtfully designed residence in one of Winter Park’s most desirable and established neighborhoods.

Listing is courtesy of: CREEGAN GROUP (407-622-1111)

Listing Agent: James Ferngren (407-739-3433)

Remarks: Welcome home to this beautifully updated two-story end-unit, ideally located just steps from Michelin-star dining, local boutiques, and the vibrant East End Market. On weekends, enjoy leisurely strolls to the area’s popular farmers markets and neighborhood events. Situated in the heart of Winter Park, this residence offers the perfect blend of lifestyle, convenience, and charm in one of Orlando’s most sought-after communities. Designed for both everyday comfort and effortless entertaining, the first floor features an open-concept kitchen and living area filled with abundant natural light, along with a convenient half bath—ideal for hosting guests. Upstairs, the spacious primary suite boasts a private ensuite bathroom, walk-in closet, and a newly refinished balcony—perfect for morning coffee or evening cocktails. Two additional bedrooms provide generous space and share access to a second balcony, creating a seamless indoor-outdoor living experience. Recent upgrades include a new dishwasher and smart refrigerator (2022), new water heater (2025), refinished front balcony (2025), new roof, and new carpet upstairs (2026). Updated light fixtures and primary bedroom flooring within the last five years add a modern touch throughout. The $400 monthly HOA fee includes landscaping and insurance, offering low-maintenance living and added peace of mind. Zoned for some of Orlando’s top-rated schools and walking distance from the new Audubon Park K-8 School, this home presents a rare opportunity to enjoy the very best of Winter Park living. Don’t miss your chance to call this exceptional property home.

Listing is courtesy of: ALL REAL ESTATE & INVESTMENTS (407-917-8206)

Listing Agent: Courtney Dietch (407-952-3779)

Remarks: Under Construction. A refined expression of new construction by LUIH Homes, this exceptional two-story residence blends timeless architecture with thoughtfully curated modern living in one of Central Florida’s desirable locations. From moment of arrival, the home impresses with beautiful curb appeal, a welcoming presence and a design that balances elegance with everyday comfort. Inside, gorgeous oak floors extend throughout the main living areas, complementing an open-concept floor plan designed for entertaining and relaxed living. The spacious chef’s kitchen serves as the heart of the home, featuring premium quartz countertops, custom cabinetry, a stylish wine bar with beverage refrigerator, and a high-end Thermador appliance package including a gas range, built-in oven and microwave. Overlooking the inviting family room with fireplace, a wall of glass sliders seamlessly connects the interior to the expansive covered lanai, creating an effortless indoor-outdoor lifestyle. The outdoor living space is equally impressive, offering generous room for lounging and dining, along with a fully equipped summer kitchen complete with a 32-inch built-in grill and beverage cooler. Beyond, a sparkling pool and spa are set within a meticulously landscaped, fenced backyard, an ideal setting for entertaining and quiet enjoyment. The first-floor primary suite provides a private retreat, featuring a large walk-in closet with a custom organization system and a spa-inspired bath with dual vanities, a soaking tub and an oversized glass-enclosed shower. A secondary bedroom suite with a private bath is also on the main level, offering flexibility for guests or multi-generational living. A spacious laundry room with Samsung washer and dryer and a well-appointed powder bath complete the first floor. Upstairs, the home continues to impress with three additional bedrooms, including one with an en-suite bath and two connected by a Jack and Jill bath. A dedicated office and a generous gathering or bonus room provide additional space for work, recreation or relaxation. Additional highlights include a two-car garage with epoxy flooring and an electric vehicle charger. Ideally just minutes from boutiques and dining of Park Avenue, as well as the vibrant restaurant scenes of Baldwin Park and Audubon Park, the home also offers convenient access to major roadways, downtown Orlando, leading hospitals, and Orlando International and executive airports. In a highly regarded A-rated public school district (Audubon K-8 and Winter Park High), this residence presents an exceptional opportunity to enjoy luxury, location and lifestyle in harmony.

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. Tremendous value in the land. Well cared for vintage Winter Park home that has 3 BEDROOM and two bath rooms. Potential to remodel, improve and expand or simply tear down to build a new custom home. However, this home is move in ready! There is not an HOA. 1343 total square feet and 1186 heated square feet. Newer DUAL-PANE WINDOWS! New HVAC system in NOvember 2025. Home was replumbed in 2024. SEPTIC PUMP OUT, OCT 2025. No carpeting instead there is SOLID FLOORING THROUGHOUT: WOOD PARQUET, TILE, LUXURY VINYL PLANK. The kitchen has been updated with SOLID WOOD KITCHEN CABINETS + GRANITE COUNTER TOPS and newer MATCHING APPLIANCES. The home has INDOOR WASHER/DRYER and a working fireplace. The back yard is FULLY FENCED. Local top rated CITY OF WINTER PARK SCHOOLS. And CITY OF WINTER PARK UTILITIES. The land, the lot have a fantastic upside. BOTH NEXT DOOR (WEST SIDE) AND REAR (NORTH SIDE) NEIGHBORING LOTS HAVE BEEN EMPTY FOR SEVERAL YEARS. This is a great investment and the property itself offers excellent rental income. Think "down the road" value + immediate return value.

Listing is courtesy of: GALLOWAY REAL ESTATE (407-421-9990)

Listing Agent: Sidney Galloway (407-421-9990)

Remarks: Motivated Sellers! Discover unparalleled luxury at The Douglas Grand, a distinguished location just a stone’s throw from Park Ave in Downtown Winter Park. This expansive 2-Story unit boasts 3,174 sq/ft of living space with your private elevator. From the moment you step inside, you’ll be captivated by the exquisite craftmanship and modern comforts that define this exceptional residence. This stunning condo boast three spacious ensuite bedrooms and abundance of storage. The heart of this home is the gourmet kitchen, custom-designed and built to fulfill every chef's dream complemented by top-of-the-line appliances that include a wall-mounted convection/microwave oven and a cutting-edge Wolfe induction stove top. The kitchen is not only functional but also perfect for entertaining, featuring a spacious breakfast bar where culinary creativity knows no bounds. As you move through this exceptional residence, in the living room, dining room, and entrance, creating an inviting ambiance that welcomes you home. Indulge in the spa-like sanctuary of the master bathroom, where luxury knows no bounds with a charming fireplace in the primary suite. Here, you'll find a sumptuous bathtub, separate vanity areas. With three generously appointed bedrooms, featuring custom closets, you'll have ample space to organize your wardrobe and storage needs effortlessly. Step onto the private balcony upstairs and be captivated by the breathtaking views. This secluded outdoor space is an ideal setting for unwinding with an evening cocktail, savoring a family dinner, or starting your day with a tranquil cup of morning coffee. The Douglas Grand enjoys a central location that places you within a lifestyle that defines this charming community. In addition to its unmatched location, this building offers a quiet, private, and secure environment—making it the perfect choice for those seeking a "lock and leave" second home or a luxurious vacation retreat. Don't miss this opportunity to experience the height of elegance and y reach of Downtown Winter Park's award-winning restaurants, cultural museums, upscale shopping boutiques, and the vibrant sophistication. Contact me today to schedule a private viewing of this remarkable residence.

Listing is courtesy of: COLDWELL BANKER REALTY (407-333-8088)

Listing Agent: Julie Scott (407-497-3492)

Remarks: Remodeled two-bedroom, one-and-one-half-bath residence in the Mead Garden Condominium community. Spanning 908 square feet, this first-floor home features a move-in-ready interior with an open-concept layout, luxury vinyl plank flooring throughout, and in-unit washer and dryer hookups, a rare offering within the building, located in the half bath. The kitchen includes raised-panel cabinetry in a warm wood tone, a mosaic tile backsplash and black appliances, including a refrigerator, range and dishwasher. A curved island with additional storage provides space for casual dining and entertaining. The kitchen opens to the dining area and living room, highlighted by a chandelier and access to a sunroom with sliding glass doors overlooking the community pool and landscaped grounds. The primary bedroom offers natural light from a pool-facing window, a walk-in closet, and an en-suite bath with a walk-in shower featuring white subway tile and a black-and-white mosaic tile floor. The second bedroom provides flexible space for guests or a home office. A half bath includes a pedestal sink, decorative mirror and gold-tone fixtures. Additional features include crown molding, updated plumbing fixtures, new windows and a leaded-glass front entry door. Near Azalea Park, Seven Oaks Park, Mead Botanical Garden and the Orange Avenue district with dining and retail. Close to Rollins College and Park Avenue.

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

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

Remarks: Designer-Curated Coastal Renovation with Exceptional Lakefront Vistas! This sophisticated reimagining was taken down to original framework and meticulously rebuilt with elevated design and superior finishes throughout. The result is an expansive openness illuminated with natural light and accented by European oak wide-plank flooring, Level 5 smooth-finish walls and ceilings, architectural recessed lighting, and custom-tailored interior doors with modern glass knob hardware. With two walls of glass, the main living space extends to a generous wraparound balcony set among lush treetops and endless lake views—the perfect backdrop for morning coffee, sunset cocktails, and open-air entertaining. A restored floor-to-ceiling brick fireplace is a dramatic centerpiece, pairing modern simplicity with timeless appeal, that adds warmth and ambiance. The striking kitchen blends clean lines with elevated finishes. Crafted maple cabinetry rises to the ceiling, complemented by sleek hardware and under-cabinet lighting that softly highlights a dimensional subway tile backsplash for added depth and texture. Crisp quartz countertops provide a seamless surface, while a suite of premium Jenn Air appliances delivers both statement-making design and top-tier performance. A large peninsula offers generous seating and gathering space—ideal for casual dining or entertaining—and incorporates a discreetly integrated pet station, a thoughtful detail that enhances daily living. Open to the surrounding spaces, the entire space feels cohesive, inviting, and effortlessly functional. The primary suite is thoughtfully planned to provide a calm and comfortable retreat, featuring truly custom closet cabinetry for streamlined storage. Expansive windows frame serene lake views and a lush green backdrop, creating a tranquil, ever-changing setting—wake to soft morning light shimmering across the water and unwind in the evening with a sense of quiet ease. Also designed with intention and precision, the primary bath maximizes space with more custom cabinetry for additional clothing storage, a streamlined vanity with quartz counter, integrated laundry cabinet, and glass-enclosed shower—all executed in a refined palette that feels both elevated and livable. The inviting second bedroom is enhanced by a built-in closet offering a polished and highly functional storage solution. Equally well considered, the second bath features quartz counters and lots of custom cabinetry for a clean, detailed look. A seamless glass shower is complimented by a strategically placed frosted entry panel offering privacy without sacrificing natural light, while a full-width mirror amplifies the sense of space. The third bedroom offers a thoughtfully designed double desk, a customized closet for added style and function and sliding glass doors to the balcony for natural light and an outdoor connection. New laundry room is both functional and refined, featuring folding counter, abundant cabinetry, and a dedicated hanging area with a built-in bench & storage drawer. Custom integrated doors discreetly conceal mechanicals. The residence also includes assigned covered parking. Residents of The Cloisters enjoy a lakefront lifestyle with dock access, boat slips, along with/ other amenities including a fitness center, and renovated clubhouse w/ kitchen, putting green and pool—all supported by a professional on-site management and beautifully maintained grounds.

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

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

Remarks: This light and bright, single-story, almost 3,000 square foot pool home features a split plan with four full bedrooms and three full baths. Your guests will immediately appreciate the expansive paver driveway, which allows easy, off-street parking. Once inside, they will admire the abundance of natural light provided by the new, large-format windows. Not only do the new windows (2022) illuminate the interior space, but they are also impact-resistant, energy-efficient, noise-reducing, and offer UV protection. The interior renovation was designed with minimal barriers between living areas, creating open, fluid spaces that enhance day-to-day living. The bedroom and bathroom layout is ideal, offering maximum privacy: two large bedrooms share one full bathroom on one side of the house, another bedroom with an en-suite bathroom is at the center, and the primary bedroom and bathroom are on the other side. Wood or natural stone flooring, extensive millwork, vaulted ceilings, new paint, updated lighting fixtures, and new fans enhance the spaces throughout. The kitchen was renovated to include an oversized, under-mount farmhouse sink, commercial-grade faucet, new LED lighting, and quartz countertops with a waterfall edge. The primary suite was updated by a former owner but was renovated by the current owner to add a second walk-in closet with custom organization. All bathrooms received light renovations, ranging from hardware and paint to new fixtures or vanities and countertops. In addition to the visually appealing renovations, the roof was replaced in 2019 and the house was re-plumbed in 2020. The outdoor improvements may be the most valued, as they created endless opportunities for outdoor living and entertaining on the newly constructed deck and enhanced landscape. All of the outdoor living benefits Florida provides are available here. A natural gas line was brought to the house as part of the renovation, allowing for easy future modifications such as a tankless gas-fueled water heater or gas-fueled outdoor grill. Located just one and a half miles from the notable retail stores and restaurants of Park Avenue and within a well-graded public school zone, there is nothing you won’t love about this home or its location.

Listing is courtesy of: CREEGAN GROUP (407-622-1111)

Listing Agent: Chris Creegan (407-622-1111)