Homes for Sale Near Winter Park High in Winter Park - 151 homes

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: Casa Noir — Brand new construction custom home selected as a 2026 Parade of Homes showcase in Winter Park. 4 bedrooms. 4 full baths. Dedicated office. Loft. 2-car garage. Just under 3,200 sq ft. Custom finishes done to perfection throughout. Inside, the foyer delivers on every promise made at the curb — soaring exposed oak beams, cascading brass pendants, and a sculpted arched alcove. Warm white oak wood floors begin here and do not stop. Anchoring the great room, the fireplace rises floor to ceiling in natural stone, with the kind of presence that makes everything else arrange itself around it. Custom oak built-ins with backlit shelving flank the space. At the far wall, a glass slider opens the room entirely to the pool beyond — where indoor and outdoor living become one. The kitchen is a destination. Custom white oak cabinetry climbs every wall to the ceiling. A full-height illuminated wine rack column. Glass-front uppers. The quartz island stretches across the heart of the room, dressed in brass pendants above and brass hardware at every pull. A 48-inch Thor gas range beneath a custom cabinet hood with integrated storage. A walk-in pantry connects both. Dining — connected, but defined. A sculptural alabaster chandelier hangs above a backlit arched niche. Easy for everyday. Elevated for hosting. Mudroom with a floating oak bench. Laundry finished in sage green cabinetry, quartz counters, and a matte black sink. Then the primary suite — and Casa Noir reaches its second act. An oak beam tray ceiling. A crystal chandelier on a brass canopy. The bath features floor-to-ceiling stone tile, a freestanding soaking tub, dual brass shower heads, and two independent floating fluted oak vanities, LED-lit at the base. The walk-in closet completes the space — floor-to-ceiling shelving, double hanging zones, and a built-in window seat. The office features moody charcoal walls, exposed oak beams, full-height wainscoting, steel-and-glass double doors, and a walk-in closet that allows it to function as a fifth bedroom when needed. The pool bath includes a fluted oak vanity with LED base lighting, terrazzo flooring, a ribbed tile shower, frameless glass, and brass throughout. Upstairs, a black steel staircase beneath a cascading glass disc chandelier leads to the loft. Three bedrooms follow — the ensuite finished in designer teal mosaic tile with brass fixtures and a frameless glass shower; the remaining two share a Jack-and-Jill bath with dual oak vanities, a herringbone tub surround, and brass throughout. Outside, a tongue-and-groove covered lanai anchors a fully built-in outdoor kitchen. Pavers lead to a crystal blue pool — a spa-resort setting that makes every weekend feel like a getaway without leaving home. Zoned for top-rated Audubon Park K-8 and Winter Park High School. Prime Winter Park location — minutes to Park Avenue, Rollins College, and more. Schedule your showing today.

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

Listing Agent: Ahmad Hassan, Pa (718-641-9358)

Remarks: Built in 2018, this beautifully designed 4-bedroom, 3.5-bath home offers 2,843 square feet of refined living in a prime Winter Park location, walking distance to Park Avenue and the renowned Winter Park 9 golf course. Thoughtful architectural details set it apart, including shiplap ceilings in the living room and kitchen, decorative ceiling finishes in the bedrooms, and a striking tile staircase wall enhanced by natural light. The open-concept layout centers around a chef’s kitchen with Wolf and Sub-Zero appliances, custom cabinetry, and Kohler fixtures—perfect for everyday living and entertaining. The primary suite features a spa-inspired bath with a marble shower, while secondary baths include Kohler and Rohl fixtures. An upstairs bonus room adds flexible living space. Enjoy a private pool, oversized two-car garage with storage, and an extended driveway for ample guest parking. Additional features include dual Carrier HVAC systems, custom window treatments, and elegant Bevolo gas lanterns that create a warm, upscale presence at night. This home offers a rare combination of style, comfort, and walkable convenience in one of Winter Park’s most desirable areas.

Listing is courtesy of: FLORIDA CAPITAL REALTY (786-953-5870)

Listing Agent: Jacob Theisen (407-908-1735)

Remarks: Rare opportunity in the heart of 32789 — priced under $500K, this 3-bedroom, 2-bathroom Winter Park home delivers the location, lot, and bones that buyers in this zip code rarely find at this price point. Zoned for Dommerich Elementary and Winter Park High School and situated on a generous 0.23-acre lot, this is the one worth moving quickly on. Upon entry, a sun-drenched living room leads to a formal dining room, which connects to a secondary living area perfect for entertaining. The open kitchen features granite countertops, stainless steel appliances, and a casual eat-in area, while refinished terrazzo floors run throughout the home adding character and easy-care durability that's quintessentially Florida. 2021 roof and HVAC mean the big-ticket items are already done. Step outside to a large screened-in patio overlooking a spacious backyard with plenty of room to add a pool or expand. Minutes from Park Avenue and Downtown Winter Park's incredible restaurants and fantastic shopping, Rollins College, UCF, AdventHealth Winter Park, Downtown Orlando, and more. At $460,000 in 32789, this one won't last.

Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)

Listing Agent: Caroline Fiore (407-538-2381)

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: Welcome to this beautifully designed and thoughtfully upgraded home that perfectly blends comfort, style, and location. From the moment you step inside, you’ll feel the difference, this is more than a home, it’s an experience. Featuring VAULTED CEILINGS THROUGHOUT, the space feels open, airy, and expansive in a way that’s both inviting and unexpected. Natural light pours in from multiple SKYLIGHTS WITH SOLAR-POWERED BLINDS, creating a warm and uplifting atmosphere from morning to evening while allowing you to set the mood with ease. The heart of the home is the FULLY REMODELED EUROPEAN-INSPIRED KITCHEN, showcasing clean lines, intentional design, and LUXURIOUS CAMBRIA QUARTZ COUNTERTOPS, perfect for both everyday living and entertaining. Enjoy peace of mind with recent upgrades including a 2024 SILENT AMANA AC UNIT, 2025 REFRIGERATOR, 2024 DISHWASHER, and 2023 MICROWAVE, offering modern convenience and efficiency. The home also features DOUBLE PANE WINDOWS, enhancing energy efficiency and comfort year-round, along with ceiling fans in the living room, all bedrooms, and patio for added airflow and ease. Step outside and experience a seamless indoor-outdoor flow, ideal for relaxing or entertaining in your own private retreat. All of this, perfectly positioned in a PRIME LOCATION NEAR SHOPPING, DINING, AND MAJOR HIGHWAYS, while still offering a sense of calm and privacy. This is more than a home… it’s a feeling. Move with Zen. SCHEDULE YOUR SHOWING TODAY!

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

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

Remarks: One or more photo(s) has been virtually staged. Set apart from the ordinary, this historic Winter Park residence offers a rare opportunity to own a home rich in character and authenticity. Homes like this, with timeless architectural detail and enduring charm, rarely come to market, especially in such a premier location just steps from the shores of Lake Virginia. Surrounded by multi million dollar estates, this 4 bedroom, 2 bath home blends classic warmth with everyday livability. Original wood floors, a wood burning fireplace, and thoughtfully designed living spaces reflect a level of craftsmanship and character that simply cannot be replicated. The spacious dining room is perfect for hosting memorable family gatherings, while the updated kitchen with wood cabinetry offers both function and charm. Upstairs, a versatile loft space provides flexibility for a media room, office, or play area, complete with peekaboo views of Lake Virginia that create a subtle connection to the surrounding landscape. Adding to the home’s appeal is a detached 20 x 20 studio flooded with natural light and offering endless possibilities, ideal for an artist’s retreat, home office, gym, or guest space.This is more than a home, it is an opportunity to own a piece of Winter Park’s character and history. Set among some of Winter Park’s most distinguished homes, this property delivers an unbeatable lifestyle, walkable to all that Park Avenue has to offer, surrounded by luxury, and full of potential to enjoy, enhance, or reimagine.

Listing is courtesy of: NORDQUIST & COMPANY INC (407-694-0996)

Listing Agent: Elizabeth Nordquist (407-694-0996)

Remarks: One or more photo(s) has been virtually staged. Experience refined living in this exquisitely renovated custom home, positioned on an oversized corner lot in one of the area’s most peaceful and private neighborhoods. Tucked away at the end of a quiet dead-end street, this residence offers an exceptional blend of craftsmanship, sophistication, and modern comfort. Inside, soaring 10-foot ceilings and a stately wood-burning fireplace set a welcoming tone in the family room. The fully reimagined chef’s kitchen is a true showpiece, featuring solid maple cabinetry, quartz countertops, programmable Bosch stainless steel range and refrigerator and a striking brick backsplash—an elevated space designed for both culinary creativity and effortless entertaining. All three bathrooms have been luxuriously renovated, and new carpeting adds a soft, refined touch throughout all four bedrooms. French doors from the master suite, formal living room, and family room open to a breathtaking screened-in pool retreat. Surrounded by lush tropical landscaping, this private oasis has been thoughtfully upgraded with a new pool pump, a conversion to a sparkling saltwater system, and a beautifully refinished pool deck. An outdoor shower with both hot and cold water adds a resort-level convenience, perfect after a swim or a day in the sun. Every major system has been meticulously updated for peace of mind, including a new programmable HVAC system, a complete replumb of the entire home, all new ductwork, and an upgraded water heater. Additional enhancements—such as fresh interior and exterior paint, a new garage door opener in the over-sized garage and refreshed landscaping — ensure a truly turnkey experience. With its luxurious finishes and meticulous improvements, this residence is ready for the next family to make it their own. Just minutes from Winter Park’s boutiques, acclaimed restaurants, and the cultural charm of Park Avenue, this home offers a rare opportunity to enjoy elevated living in a setting that’s both secluded and connected. A truly private sanctuary designed for comfort, style, and the best of Florida living.

Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)

Listing Agent: Kathy Summers (407-832-6986)

Remarks: Rare opportunity to own a beautifully upgraded lakefront property on half acre in one of Winter Park's most desirable locations. This homesite offers the perfect setting to enjoy the current residence or build your future dream home! When you step inside you'll find a thoughtfully updated kitchen featuring high-end appliances, custom cabinetry, and designer finishes. The home boasts new windows that fill the space with natural light and frame serene lake views, as well as a brand new roof and AC offering peace of mind for years to come. Split floor plan with 3 large bedrooms and each has a walk-in closet. Step outside and take in the beautifully landscaped yard, complete with mature trees and plenty of space and privacy. Whether you’re sipping coffee by the water or hosting friends for a sunset BBQ, this home is made for living the good life! Zoned for A rated schools. Situated on a quiet street yet just minutes from Winter Park and Baldwin Park dining, shopping, parks and culture. Call today before it's gone!

Listing is courtesy of: TAL BUSIDAN PA (407-227-3001)

Listing Agent: Tal Busidan (407-227-3001)

Remarks: Rarely does a property of this caliber grace the Winter Park market. Nestled along the coveted Venetian Canal with 95 feet of pristine waterfrontage, this magnificent masonry estate is the pinnacle of refined Florida living — offering 6,396 square feet of meticulously crafted space, a private boathouse, resort-style grounds, and an address mere steps from the best of Park Avenue. From the moment you arrive, the circular driveway, porte-cochère, and motor court signal that something extraordinary awaits. Solid brick construction and lush, manicured landscaping frame a grand entrance that sets the tone for every detail within. Step through the dramatic grand foyer into a home defined by elevated ceilings, rich hardwood floors, and exquisite crown moldings throughout. The formal living and dining rooms offer elegant spaces for entertaining, while a beautifully appointed wine room with stunning glass doors adds an unmistakable touch of sophistication. A chef's kitchen that truly inspires — outfitted with professional WOLF, Sub-Zero, and Miele appliances, dual islands with breathtaking countertops, a prep sink, built-in nugget ice machine, and a butler's hallway with floor-to-ceiling storage — flows effortlessly into the warm and inviting family room (complete with fireplace) and informal dining area. Bright, sun-drenched interiors and French doors open to a spectacular covered outdoor kitchen and a beautifully landscaped turf backyard, where a stunning saltwater pool and spa invite you to unwind in style. The first-floor primary suite is a sanctuary unto itself — featuring a private office, den, or sitting room anchored by a stunning double-sided fireplace, and a spa-caliber en suite with double vanities, jetted soaking tub, walk-in shower, and an oversized custom-built walk-in closet. A true retreat from the world. Upstairs, four generously sized bedrooms offer comfort and privacy for family and guests alike. One bedroom enjoys its own private en suite and a delightful secret bonus room — a magical hideaway perfect for children. Two bedrooms share a beautifully appointed Jack-and-Jill bath, each with its own private vanity area, and the fourth bedroom is spacious and well-served by the hall bath. The pièce de résistance of the upper level is a state-of-the-art home theater, complete with projector and screen, ceiling surround sound speakers, and a built-in dry bar with wine fridge — the ultimate in at-home entertainment. A detached guest casita with a full bath and wet bar provides ideal accommodations for visitors, while a detached three-car garage offers ample space for vehicles and storage. Two laundry rooms — one per floor — add everyday convenience, and custom storage solutions are found throughout. The whole-house Lutron lighting system and full-house generator ensure comfort, security, and seamless living at every turn. And then there is the water. The private boathouse along the Venetian Canal, with 95 feet of serene waterfront, offers a lifestyle that simply cannot be replicated — direct access to Winter Park's legendary chain of lakes, all from your own backyard. Located just a short stroll to the boutiques and dining of Park Avenue, the beauty of Kraft Azalea Gardens, and the Winter Park Racquet Club, this estate offers not just a home — but a way of life that the most discerning buyers have only dreamed of.

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

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

Remarks: Offering WELL BELOW appraised value!! Buyer financing fell through, act quickly this one wont last long. In one of Winter Parks most sought after neighborhoods, take a look at this exceptional 3-bedroom, 2-bathroom pool home with an additional bonus space. Completely reimagined with a designer’s eye, this residence blends high-end aesthetic with the ultimate peace of mind—with a newer roof, A/C, and water heater. Step inside to a Sun-filled sanctuary featuring new luxury vinyl plank flooring and gorgeous tile. The heart of the home is the brand-new chef’s kitchen, featuring custom white oak wood cabinetry, rare Taj Mahal quartzite countertops, and elegant champagne bronze finishes throughout. The kitchen flows seamlessly into the living areas, where new tile work elevates the wet areas for a cohesive, upscale feel. Work from home in style in the dedicated bonus room, an ideal footprint for a private office or creative studio. This home features true functionally for a family to live in everyday. This one of a kind home features a custom in home laundry room, custom vanities, a fireplace made to enhance the homes aesthetic & custom doors through the entire home. Beyond the interior, your private Florida lifestyle awaits. Retreat to the expansive screened-in pool, patio and large backyard. Located just steps from the Winter Park Pines Golf Course and the scenic Cady Way Trail, this home offers more than just a renovation—it offers a lifestyle. Enjoy easy access to the clubhouse for dining, top-rated schools, and the vibrant culture of downtown Winter Park. With every detail thoughtfully curated and major systems already updated, this is the turnkey masterpiece you’ve been waiting for.

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

Listing Agent: Rene Droz, Iii (407-484-8786)

Remarks: One or more photo(s) has been virtually staged. Experience luxury living in this stunning, fully remodeled single-family home located in the heart of Winter Park, where modern sophistication meets exceptional functionality. This spectacular residence features a total of 4 spacious bedrooms and 3 modern bathrooms, boasting sleek laminate flooring throughout and a chef-inspired kitchen fully equipped with premium stainless steel appliances. A standout feature of this property is its versatile layout: one bedroom and one bathroom are completely separate from the main living area, offering the perfect solution for guest privacy, a multi-generational suite, or an opportunity to generate additional rental income. Outside, the massive backyard and sparkling pool provide an ideal setting for family gatherings and outdoor entertainment, all while being nestled in a prime location just minutes from the iconic Park Avenue shopping district, the Winter Park Farmer’s Market, and convenient access to the 436. This home is the ultimate choice for those seeking the perfect blend of suburban tranquility and urban convenience in the very best of Central Florida living.

Listing is courtesy of: MY REALTY GROUP, LLC. (786-847-7421)

Listing Agent: Maria Gomez Arevalo, Pa (407-705-7203)

Remarks: Located in highly desirable Lugano Terrace just steps from the shores of Lake Knowles, this stunning all new interiors, 5-bedroom, 3.5-bath brick home effortlessly blends timeless charm with extensive modern updates. Set on a beautifully oversized landscaped lot with a roundabout driveway. Winter Park’s most sought-after neighborhoods adjacent to the Vias, Winter Park Racquet Club and Dommerich Elementary. Inside, wide-plank engineered white pine flooring flows throughout, complementing vaulted ceilings, wood-burning fireplace in the living room, and a spacious open layout ideal for entertaining. The informal dining room overlooks the private backyard and resurfaced PebbleTec pool, while the chef’s kitchen impresses with dual islands, quartz countertops and full-height quartz backsplash, custom hood, Thermador appliances including a 48” six-burner gas range and French door refrigerator. The gorgeous, light filled family room showcases gas fireplace and a built-in bar with wine fridge. The expansive upstairs primary suite is a luxurious retreat, featuring a spa-like bath with a dual-entry shower with Infrared sauna, soaking tub, dual vanities with LED mirrors, expanded closets, and a sitting area. Also upstairs is a flexible loft or library space, an office/nursery with a private balcony, and a bonus exercise room or third closet. Three spacious bedrooms are located downstairs, including a second primary or guest suite with its own en-suite bath and pool access. Notable upgrades include a new roof (2021), PEX plumbing and water heater (2025), updated electrical panels, new propane tank, new AC supply grills and a new second AC system (2025). Additional features include Level 4 smooth drywall, custom trim and moldings, 8’ metal front and double back doors, custom wood interior doors, upgraded light switches and plugs, all-new designer light fixtures ( Regina Andrew, Visual Comfort, etc. ), fireplace surrounds, and custom metal and wood staircase. Black interior and exterior Anderson windows: Dual Pane Low-E Smart Sun Standard Argon Fill Simulated Divided Light (SDL). Outside, enjoy a fully fenced and gated backyard with turf and paver landscaping, updated pool coping, and a covered porch ideal for entertaining, new exterior paint and gas lanterns. The 2-car garage includes custom paneled doors, painted floor and workshop area. Located within walking distance to top-rated Dommerich Elementary, Maitland Middle, and Winter Park High, and just minutes from Park Avenue and the Winter Park Racquet Club and Interlachen Country Club, this home offers exceptional quality, location, and lifestyle. NEW April 2026 Black Steel doors windows with low e-dual pane glass ($150k value!).

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

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

Remarks: Experience refined Winter Park living in Kenilworth Shores, a highly sought after neighborhood near Baldwin Park, Lake Baldwin trails, and the dining and boutiques of Park Avenue. This location places you close to Rollins College, Winter Park High, and the cultural center of Winter Park FL. Inside, natural light moves through open living spaces finished with wide porcelain tile floors. The kitchen stands as a sophisticated gathering space with a large quartz island, custom cabinetry, Bosch appliances, and a walk in pantry. The primary suite offers a peaceful retreat with direct access to the pool and a spa inspired bath. A second ensuite bedroom, dedicated office, and generous flex room provide versatility for daily living. The backyard feels like a private resort with a covered outdoor kitchen and a sparkling pool framed by thoughtful landscaping. This property may qualify for a seller funded permanent rate buydown with a participating lender. Equal Housing Opportunity.

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

Listing Agent: Christina Fata (407-917-8946)

Remarks: Welcome to your dream home! This exceptional 4-bedroom residence features a desirable split floor plan, offering both privacy and functionality. Nestled on a quiet corner lot in the serene Winter Park Pines community, this property is just a few steps away from the scenic Cady Way Trail, perfect for outdoor enthusiasts.This home is surrounded by recreational opportunities, including a refreshing pool, pickleball courts, and miles of trails for jogging, biking, or leisurely strolls. Enjoy the outdoors while being in close proximity to shopping, dining, and the celebrated Winter Park schools.Recent updates make this home truly special. The new A/C system and upgraded electrical panel—complete with room for additional breakers—ensure your comfort and convenience. The manifold system has also been updated, and the roof was newly installed in 2018 for peace of mind.Additionally, half of the windows have been replaced with high-quality Anderson windows, enhancing both energy efficiency and natural light.Don’t miss the opportunity to own this well-maintained home in a vibrant neighborhood that perfectly balances recreation and relaxation. Schedule your showing today!

Listing is courtesy of: VERSALIS REALTY POWERED BY SELLSTATE (407-608-9593)

Listing Agent: Tammy Cuddy (407-608-9593)

Remarks: One of the most coveted neighborhoods in all of Winter Park! This custom-built 5-bedroom, 5.5-bath residence was completed in 2017 and first sold in 2018. Lovingly maintained by the original owner and elevated with high-end designer finishes, the home showcases the impeccable vision of renowned designer Ted Maines, who reimagined much of the interior with timeless sophistication. Perfectly positioned on a prime over-sized corner lot, the home blends transitional architecture with modern elegance. Sunlight fills the open layout through expansive sliding doors, creating effortless indoor-outdoor flow. The main living area seamlessly connects a formal living room and spacious dining area to the gourmet kitchen, complete with custom cabinetry, Carrara marble surfaces, and Sub-Zero and Wolf appliances. A cozy family room with fireplace provides a relaxed yet stylish gathering space. The private downstairs primary suite opens directly to the lanai, saltwater pool and features a spa-style bath. A secondary ground floor bedroom is perfect for guests or multigenerational living. Upstairs, enjoy a spacious loft with custom bar, leading to a versatile media room. Three additional en-suite bedrooms complete the second level. Recent enhancements include a full-house generator, a newly added semi-circular driveway that enhances curb appeal and functionality, and three newer A/C units with re-engineered, high-efficiency ductwork to ensure optimal climate control throughout the home. The outdoor living space is equally impressive, offering a saltwater heated pool and spa with cascading waterfall, elegant stone decking, ambient lighting, and a covered summer kitchen—ideal for year-round entertaining. A rare 3-car garage completes this exceptional home. All just moments from the shops, dining, and charm of downtown Winter Park.

Listing is courtesy of: SCANLON REALTY GROUP LLC (305-905-0496)

Listing Agent: Brian Scanlon (305-905-0496)

Remarks: This custom home is nestled in an up-and-coming neighborhood in Winter Park. This stunning home redefines modern living. Designed with an open floor plan, it seamlessly blends spaces to create a harmonious flow, perfect for both entertaining and everyday life. The abundance of windows bathes the interiors in natural light, creating a bright and airy ambiance. The office/study is set apart for quiet pursuits. The chef’s kitchen opens naturally to the great room and boasts a large island, top-of-the-line Thermador appliances, complemented by the sleek quartz countertops that offer both style and functionality. Conveniently equipped with two sets of washers and dryers, this home ensures efficiency and ease for the busiest of households. Retreat to the master suite, where luxury meets serenity. A massive walk-in closet provides ample storage, while the spa-like master bath invites relaxation with its elegant design and premium features. The indoor outdoor flow is easy with the huge set of glass sliders leading to the covered porch equipped with drop down screens. Enjoy the summer kitchen and sparkling pool while entertaining family and friends. This home is a true gem that combines thoughtful details with sophisticated style.

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

Listing Agent: Matthew Burks (407-257-5347)

Remarks: Welcome to this spacious and well-maintained 2 story townhome in the heart of Winter Park, located in the highly sought-after Four Seasons community. This 2-bedroom, 1.5-bath unit offers 1,266 square feet of comfortable living space with a functional layout, abundant natural light, and thoughtful updates throughout. Step inside to find a spacious kitchen, renovated in 2016, featuring wood cabinetry, granite countertops, black appliances, and a dishwasher replaced in 2023, perfect for everyday cooking and entertaining. Just off the kitchen, enjoy a dedicated dining area, ideal for hosting dinners or creating a flexible space for a home office or additional seating. The inviting living room provides plenty of space to relax and gather, with sliding glass doors that lead to your private, fully fenced, tree-shaded patio complete with a storage shed - an ideal spot to enjoy your morning coffee or unwind in the evenings. The patio also offers convenient access to your covered, deeded carport space, #49. Both bedrooms are generously sized, with the primary bedroom featuring dual closets and a ceiling fan for added comfort. The home includes a full bathroom and a convenient half bath, both thoughtfully updated with new toilets and upgraded vanities, including a quartz countertop and stylish shiplap accent in the guest bath. Additional interior highlights include custom closet features, a laundry closet with a new stackable washer and dryer(included), ceiling fans and blinds throughout, fresh interior paint (2024), and an HVAC system updated in 2023, providing peace of mind and modern convenience. Residents of Four Seasons enjoy access to a variety of amenities including 3 swimming pools, a clubhouse with fitness center, tennis and shuffleboard courts, all within a quaint, established neighborhood with tree-lined walkways. Ideally located just minutes from Ward Park, Winter Park Pines Golf Club, YMCA, AdventHealth Winter Park, and the Center for Health & Wellbeing. Enjoy easy access to shopping and dining along Aloma Avenue including Publix, Sprouts, and Aldi, as well as being less than 10 minutes from Park Avenue’s renowned restaurants and boutiques. Conveniently located near SR 436 with quick access to 417 and 408, and approximately 25 minutes to Orlando International Airport. Zoned for top-rated schools: Brookshire Elementary, Glenridge Middle, and Winter Park High School. Don’t miss your opportunity to own in one of Winter Park’s most desirable communities—schedule your private showing today!

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

Listing Agent: Amy Turner (407-803-3885)

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: Fabulous Winter Park location. This is a 3 bedroom, 2 bath patio home with a great layout, split bedroom plan, high ceilings in the living room, and an eat in kitchen that is open to the family room. A large primary bedroom which has a walk in closet, two additional closets and french doors leading out to the back yard. There is a screened in patio off of the breakfast / dining area and an interior laundry room. Zoned for Winter Park schools, minutes from downtown Park Ave., Rollins College and Advent Health Winter Park. Property is a gem perfect for a renovation or an opportunity to build new.

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

Listing Agent: Meg Dolan (321-948-0701)