Homes for Sale Near Winter Park High in Winter Park - 206 homes

Remarks: This exceptional Winter Park residence offers a floor plan rarely found in the area, with nearly all living spaces thoughtfully positioned on a single level for effortless everyday living. Completely rebuilt in 2018 by renowned custom builder Posada Homes, a member of the elite Master Custom Builders Council, the home blends modern design, crisp architectural lines, and timeless elegance across an expansive 0.39-acre lot along one of Winter Park’s most picturesque tree-lined streets. The home immediately captivates with its refined architecture and beautifully manicured grounds. Inside, sunlight streams through expansive windows, illuminating hardwood flooring, intricate millwork, and thoughtfully curated finishes that reflect the craftsmanship of a true custom build. Just off the foyer, a hidden wine room provides a sophisticated surprise, perfect for those who love to entertain. At the center of the home is the chef’s kitchen designed for both beauty and functionality. Outfitted with premium Thermador appliances, sleek quartz countertops, a generous center island, and custom cabinetry, the kitchen flows effortlessly into the expansive great room where high ceilings, designer lighting, and elegant architectural details create an atmosphere that is both inviting and refined. Tucked away for privacy, the primary suite is positioned just off a luxurious family room featuring custom built-ins and a gas fireplace. The primary suite itself is a true sanctuary, complete with a sitting area, private coffee bar, and a spa-inspired bath featuring dual vanities, a soaking tub, and an oversized walk-in shower. Rarely found in Winter Park, all bedrooms are conveniently located on one level, including two primary suites, allowing the home to deliver seamless livability without sacrificing architectural interest or sophistication. Upstairs, a private office, half bath, and bonus room provide the perfect space for work, media, recreation, or relaxation. Outdoors, the home transforms into a private resort-style retreat. A covered lanai overlooks the sparkling pool and expansive grounds, creating the ideal setting for entertaining or quiet evenings at home. Adding even more flexibility, a 252-square-foot detached studio currently functions as a gym but could easily become a summer kitchen cabana, guest retreat, or art studio. Located within walking distance of Park Avenue’s boutiques, restaurants, and cafés, and just moments from Rollins College and the Winter Park Chain of Lakes, this residence embodies luxury living at its finest. Don’t miss this rare opportunity to own one of Winter Park’s most outstanding homes. The current flooring offers a rich look, and for those who prefer a lighter palette, the seller is open to providing a credit toward flooring updates and coordinating the installation of new flooring if desired.

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

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

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

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

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

Remarks: Under contract-accepting backup offers. Welcome to The Cloisters, one of Winter Park’s established lakefront communities, ideally between Park Avenue and Lake Osceola. This top-floor residence, rarely available in the building, offers a turnkey lifestyle with exceptional updates and peaceful water views. The home’s oversized screened balcony, complete with a custom awning, creates an uncommon open-air retreat that overlooks the community’s heated pool, putting green, manicured gardens and Lake Osceola. Unlike many residences in the community, this property retains its original open balcony design, offering outdoor living rarely found in this floor plan. Inside, every surface has been thoughtfully remodeled. The kitchen features solid wood cabinetry, granite countertops and refined finishes. Both baths are fully updated, including a new tub with glass enclosure in the guest bath and a walk-in shower with frameless glass in the primary suite. Tile flooring, custom vanities and designer fixtures complete each space. Engineered hardwood flooring runs throughout the main living areas, with plush carpet in the bedrooms for added comfort. The primary suite includes custom built-ins, dual closets and a built-in desk with additional cabinetry, delivering elegance and function. The second bedroom offers flexibility as a guest room or study and features optional shared access from the primary suite for additional privacy. Additional highlights include a covered and assigned parking space equipped with one of the building’s few electric vehicle charging stations, ample guest parking and access to a community dock with boat slips available through a resident lottery system. The Cloisters has successfully completed all required Milestone Inspections and the Structural Integrity Reserve Study, ensuring peace of mind for future residents and affirming the association’s commitment to long-term stewardship. Amenities include two fitness centers with dry saunas and a newly renovated clubhouse with kitchen and a partial bath for use as a powder room, ideal for hosting private events. Ideally positioned just steps from the dining, shopping and cultural energy of Park Avenue and in proximity to Rollins College, this original-owner residence offers a compelling blend of lifestyle, location and enduring design.

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

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

Remarks: Remodeled pool home located in the highly sought after desirable Winter Park school district. This property has a.27 acre corner lot with room to expand and a pool/spa perfect for relaxing or entertaining guest.Inside the living room features vaulted ceilings that create a bright open feeling and a huge screened in patio for outdoor entertaining. The bathrooms have been beautifully remodeled, there are new windows, new electric outlets throughout, new light fixtures, roof replaced in 2022,kitchen beautifully redone 2020 with new cabinets and Granite counter tops. Additional upgrades throughout the home include new luxury vinyl flooring, new vanity in master bath, new enhanced pool liner, new robot pool vacuum, new garage door house has been painted inside and out. The location is close to shopping, Costco and other stores also located near by. Full Sale, Rollins College and downtown Winter Park to the west and UCF to the East within close proximity. This is a must see. Owner is realtor.Buyer to verify room measurements.

Listing is courtesy of: JC FLORIDA REALTY LLC (407-257-8265)

Listing Agent: Eva Firios (321-662-1501)

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: 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. Introducing one of Winter Park's most extraordinary offerings — a meticulously designed transitional masterpiece by the acclaimed Winter Park Custom Homes, set on a rare 0.34-acre corner lot in one of the city's most coveted neighborhoods. From the moment you arrive at the circular front drive and step onto the marble-tiled covered front porch, it's clear this home is in a class of its own. Inside, soaring beamed ceilings and wide-plank engineered wood floors set an elevated tone throughout. The grand living room features a gas fireplace and dramatic accordion glass doors that dissolve the boundary between indoors and out, opening to the resort-style backyard with ease. The chef's kitchen is a true work of art: anchored by a massive island with wraparound seating, Thermador gas range and oven, built-in refrigerator and microwave, marble countertops, and a generous walk-in pantry — all complemented by stunning herringbone hardwood floors that make this space feel straight out of the pages of a design magazine. A butler's hallway and charming brick-floored cozy reading room add warmth and character to the everyday. Also on the main level, a full en-suite office — easily serving as a 6th bedroom — offers flexible living for guests or multi-generational needs, while a separate powder room is thoughtfully reserved for guest use. The primary suite is a sanctuary unto itself: a private vestibule entry leads to a spacious bedroom retreat with accordion-style doors that open directly to stepping stones leading into your personal spa. The spa-inspired primary bath showcases marble countertops and inlay floors, separate sink vanities, a freestanding soaking tub, a walk-in shower, and a custom-built walk-in closet that rivals any boutique. Upstairs, four generously sized en-suite bedrooms — each with walk-in closets — surround a spectacular bonus room complete with a wet bar, perfect for entertaining or movie nights. The third floor is a true Winter Park rarity — an expansive additional living level with a dedicated gym area and playroom ideal for home theater, creative pursuits, or whatever your lifestyle demands. Built-in speakers complete the experience. Step outside to your own private resort. A heated pool and spa with a sun shelf, fire bowl, and serene stepping stones are framed by lush artificial turf and elegant marble-inlaid pavers. The covered back patio with tongue-and-groove ceiling and fireplace creates an al fresco living room, while the outdoor grill with prep sink makes entertaining effortless. Natural gas throughout, a full-house generator, sauna, and an epoxy-floored two-car side garage round out this exceptional property — all seamlessly controlled through a whole-home Control4 automation system that puts lighting, climate, audio, security, and more at your fingertips. Zoned for A-rated Winter Park schools and just minutes from Park Maitland School (K–6), Park Avenue's world-class dining and boutiques, and all that Central Florida has to offer. Homes of this caliber, at this scale, in this location simply do not come available often. This is not just a home — it's a lifestyle.

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

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

Remarks: Welcome to 1981 Blue Ridge Rd in Winter Park, a spacious 4-bedroom, 2-bath home featuring an open floorplan, a generous family room, and a layout designed for both comfortable everyday living and easy entertaining. The home offers a well-connected flow between the main living spaces, creating an inviting setting with room to gather, relax, and spread out. Inside, the living room, dining room, and kitchen are arranged in a way that supports an open and functional feel, making the home especially appealing for hosting and daily routines alike. The family room adds valuable extra living space and creates a natural hub for movie nights, casual gatherings, or a second lounge area. The floorplan also shows a sun room extending off the family room, giving the home even more flexibility for relaxing, hobbies, or enjoying a bright bonus space with views of the backyard. The bedroom layout is thoughtfully separated from the main entertaining areas, offering privacy and comfort. The primary suite is positioned apart from the secondary bedrooms and includes its own bath and closet space, creating a peaceful retreat within the home. Three additional bedrooms provide flexibility for guests, a home office, or changing household needs. Outside, the open patio and private yard add to the home’s lifestyle appeal, creating space to enjoy outdoor dining, weekend get-togethers, gardening, or quiet mornings in the Florida sunshine. Together with the interior layout, these outdoor features help make the home feel both versatile and welcoming. Located in Winter Park, the property is set in a highly desirable area known for its established residential feel, attractive surroundings, and convenient access to shopping, dining, parks, and everyday amenities. The neighborhood adds to the home’s appeal by offering both comfort and accessibility in one of Central Florida’s most sought-after locations. **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.**

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

Listing Agent: Thomas Nickley, Jr (407-629-4420)

Remarks: One or more photo(s) has been virtually staged. Welcome to Park West Condominiums — one of Winter Park’s most coveted and rarely available condominium communities, ideally located just one block from the boutiques, dining, and charm of Park Avenue. This unique 4th floor residence offers an exceptional combination of space, privacy, and potential. Featuring 3 bedrooms and 2 bathrooms, the expansive floor plan has been enlarged by enclosing two patios, creating generous living spaces rarely found in condominium living. Vaulted ceilings, skylights, and abundant natural light enhance the open, airy feel throughout the home, while the top-floor location provides remarkable tranquility and privacy. The spacious kitchen offers ample counter space, a breakfast bar, and excellent cabinet space, while the living area is anchored by a fireplace — another uncommon feature in condo living. Large bedrooms, a sizable in-unit laundry room with extensive storage, and an oversized attic provide an extraordinary amount of storage seldom seen in comparable properties. The primary suite features vaulted ceilings, a walk-in closet, and a spacious bathroom layout. For maximum flexibility, the second bedroom, featuring a bright Sun Room alcove, connects to the primary bedroom so it could also be utilized as a private den. Recent unit improvements include a NEW HVAC system, a NEW Water Heater, and Plumbing updates. A reserved covered parking space is included, along with plentiful guest parking for visitors. Residents of Park West enjoy a secure gated entrance, community pool, tennis court, on-site community manager, and beautifully maintained grounds with extensive recent community improvements completed. Association fees include water, sewer, and trash service, creating a truly low-maintenance “lock-and-leave” lifestyle ideal for travelers or seasonal residents. While this condo presents an exciting opportunity for personalization, the location, floor plan, and features make this an exceptional offering with tremendous potential. Opportunities in Park West are exceedingly rare — this is your chance to create something truly special in the heart of Winter Park.

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

Listing Agent: Erin Baker (407-719-0030)

Remarks: Nestled in one of Winter Park’s most sought-after neighborhoods, this charming and meticulously maintained home offers three bedrooms, two baths, an open floor plan, hardwood floors, and thoughtful updates throughout. Recent improvements include a new AC, new hot water heater, new driveway and walkway pavers, and refreshed front and backyard landscaping featuring a magnolia tree, camellias, gardenias, and more. Just minutes from Park Avenue’s beloved restaurants, cafés, and boutiques, as well as the scenic Winter Park Chain of Lakes, this home offers both character and convenience. With easy access to I-4, SR-417, Orlando International Airport, and top-rated schools, it is a wonderful opportunity to enjoy classic Winter Park charm in a beautifully cared-for home.

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

Listing Agent: Kyle Grafton (203-246-8512)

Remarks: Welcome to an incredible opportunity to own a home in one of Central Florida’s most desirable zip codes — Winter Park 32789 — for under $400,000! Surrounded by million-dollar neighborhoods, this 3-bedroom, 2-bath home offers outstanding value, endless potential, and a prime location close to shopping, dining, parks, and everything Winter Park has to offer. Located in a highly sought-after school district featuring Dommerich Elementary School, Maitland Middle School, and Winter Park High School, this property is ideal for homeowners and investors alike. Inside, you’ll find a Great Room floor plan with a separate dining room, split-bedroom layout, neutral interior paint and luxury vinyl plank flooring installed just four years ago throughout the home. The galley kitchen offers functional space and flows easily into the main living areas, while updated vanities and ceiling fans throughout add comfort and style. A large inside laundry room provides additional convenience. Sliding glass doors lead to a screened back porch overlooking the expansive backyard on this .23 acre lot — offering plenty of room to entertain, garden, expand, or create your dream outdoor retreat. Additional features include a 1-car carport and strong long-term investment appeal, as this property has been income-producing for decades. Whether you’re looking to personalize your forever home, secure a valuable investment, or break into Winter Park’s premier 32789 zip code at an exceptional price point, this property is packed with opportunity!

Listing is courtesy of: SUN PROPERTIES, INC. (407-645-5700)

Listing Agent: Andrew Musashe (407-645-5700)

Remarks: Tucked away on a quiet cul-de-sac in highly sought-after Winter Park, this beautifully updated three bedroom, two bathroom duplex offers the perfect blend of comfort, style, and location—just steps from Winter Park Pines Golf Club. Once inside you discover open living spaces featuring warm wood flooring throughout the living areas and bedrooms, complemented by vaulted ceilings in the main areas and ceiling fans that enhance the home’s airy feel. The brand-new kitchen has tile flooring and is not only functional, but beautiful showcasing classic shaker cabinets, sleek quartz countertops, and stainless steel appliances—perfect for both everyday living and entertaining. There are three nice sized bedrooms, all with large closets. The primary bedroom features sliding glass doors that lead directly to the large backyard and open patio. Both bathrooms have been renovated with modern finishes, including new vanities, countertops, tub/showers, plus durable and stylish luxury vinyl plank flooring. Situated on a generously sized corner lot, the property offers plenty of outdoor space to enjoy, along with a charming paver front patio and the convenience of a one-car garage with opener. You will love the privacy of this end unit on the quiet cul-de-sac. Enjoy the ease of walking to nearby schools and being just moments from golf, shopping, dining, and all that Winter Park has to offer. With low HOA dues and located in a top-rated school district, this is an incredible opportunity in one of Central Florida’s most desirable neighborhoods.

Listing is courtesy of: SUN PROPERTIES, INC. (407-645-5700)

Listing Agent: Andrew Musashe (407-645-5700)

Remarks: Welcome to 2708 Lion Heart Rd, where timeless charm meets modern elegance in the heart of Winter Park. This beautifully reimagined home has been thoughtfully renovated from top to bottom, offering a seamless blend of style, comfort, and functionality. Step inside to discover brand-new luxury vinyl plank flooring flowing throughout, creating a warm and cohesive feel in every room. The stunning two-tone kitchen is a true centerpiece, featuring sleek quartz countertops, contemporary finishes, and new appliances to be installed at closing—perfect for both everyday living and entertaining. The upgrades continue in the fully renovated bathrooms, where carefully selected color palettes and high-quality finishes provide a fresh, sophisticated look designed to stand the test of time. Every detail of this home has been meticulously considered, leaving no space untouched. Outdoors, enjoy your private oasis with a newly resurfaced pool—ideal for relaxing weekends or hosting gatherings year-round in Florida’s sunshine. This move-in-ready gem offers the perfect opportunity to own a like-new home in a highly desirable location. Come experience the beauty, quality, and lifestyle that 2708 Lion Heart Rd has to offer—your dream home awaits.

Listing is courtesy of: EQUITYPRO LLC (407-203-6860)

Listing Agent: Navid Rokh (321-900-5977)

Remarks: Under contract-accepting backup offers. 2026 PARADE OF HOMES ENTRY! - Positioned on an expansive corner lot in the heart of Winter Park, this extraordinary new masterpiece is a true architectural statement, delivering a level of craftsmanship and detail that is simply unforgettable. Framed by a massive front yard and a canopy of mature trees, the bold modern façade creates an immediate sense of arrival and sets the tone for what lies within. A grand set of double doors opens to a breathtaking two-story entry, where a dramatic marble mosaic feature establishes the home’s elevated design from the moment you step inside. The main living space is nothing short of stunning, anchored by a sleek electric fireplace and custom built-ins with integrated LED underlighting. At the heart of the home, the chef’s kitchen is a true showpiece, outfitted with Dekton Cosentino countertops, a paneled refrigerator, a full suite of Thermador appliances, and a hidden walk-in pantry. The kitchen flows effortlessly into the dining room which is bathed in natural light from an oversized statement window, making it perfect for hosting at any scale. Designed with versatility and luxury in mind, the home features two primary suites, one on each level. The downstairs primary offers soaring 12-foot ceilings and a serene, spa-like bath wrapped in marble mosaic tile. Upstairs, the main primary suite is a true showstopper, defined by its scale and attention to detail. Dual custom closet systems include an expansive hers closet complete with a dedicated makeup vanity, while the bathroom delivers a resort-caliber experience with stunning marble floors, a freestanding soaking tub, and dual vanities. The upper level continues to impress with a spacious loft designed for both relaxation and entertaining, complete with a custom entertainment center, wet bar, wine fridge, and a full bath. Each additional bedroom is ensuite, offering privacy and comfort for family and guests alike. Outdoor living rivals that of a private resort. A massive covered lanai features a fully equipped summer kitchen with tile backsplash, overlooking an expansive lounging area framed by a wall of glass. The heated pool and spa create the ultimate setting for year-round enjoyment, while the oversized front yard (an incredibly rare find in Winter Park), adds an unmatched sense of space and setting rarely found in this market. Additional features further elevate the home, including a sleek metal roof, striking hex LED lighting in the garage, and curated designer lighting fixtures throughout. Perfectly positioned just moments from Lake Chelton and Virginia Heights Park, with easy access to the boutiques and dining of Park Avenue and the charm of Hannibal Square, this residence offers a lifestyle that is as elevated as the home itself.

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

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

Remarks: Under contract-accepting backup offers. Beautiful Windsong custom home completely reimagined with a sophisticated interior design overhaul that now presents as a true Winter Park boutique luxury residence. This stunning 4 bedroom, 3.5 bath home blends timeless elegance, thoughtful craftsmanship, and warm entertaining spaces in one of the area’s most sought-after neighborhoods. Every room feels intentional and refined, showcasing elegant finishes, designer touches, and a fresh, elevated aesthetic throughout. Recently fully repainted and enhanced with gorgeous new quartz countertops and a crisp white pearl subway tile backsplash, the home now feels both current and timeless while maintaining the charm and character buyers love about Winter Park living. At the heart of the home is a spectacular chef’s kitchen featuring top-of-the-line Viking and Bosch stainless steel appliances, including a Viking gas range with griddle, a large center island with counter seating, stunning cabinetry, and a dramatic 10-foot coffered ceiling. The kitchen flows seamlessly into the inviting family room with gas fireplace and custom window seating, creating the perfect setting for both everyday living and upscale entertaining. Triple French doors open to a generous covered lanai complete with a summer kitchen, built-in grilling station, and beautifully designed outdoor spaces beaming with old-world charm rarely found in newer construction homes. The turf backyard offers easy maintenance while creating a warm and private atmosphere for gatherings year-round. The formal dining room is equally impressive with crown molding, wainscoting, abundant natural light from the oversized bay window, and direct access to a convenient butler’s pantry and dry bar, making hosting effortless. Upstairs, the magnificent owner’s retreat offers oversized walk-in closets and a luxurious spa-inspired bathroom adorned with glorious marble tile work and elegant designer finishes. Two additional generously sized bedrooms share a marble bath and the 4th bedroom is currently shown as an office, with adjacent hall full bath. A downstairs powder room outfitted in new england blue theme is great for guests. Additional luxury features include hardwood flooring, plantation shutters, surround sound, tankless gas water heaters, an electric vehicle charger, oversized two-car garage with high ceilings and level 5 drywall finish, and countless thoughtful upgrades throughout. Located within the highly desirable Windsong community, residents enjoy access to incredible amenities including two resort-style pools, lakefront clubhouse, water park, playground, fishing pier, kayaks, paddleboards, and even a residents-only pontoon boat to explore the Winter Park Chain of Lakes. Just minutes from Park Avenue, Baldwin Park, and top-rated Winter Park schools, this is your opportunity to step directly into the Winter Park home of your dreams—fully upgraded, impeccably styled, and ready now.

Listing is courtesy of: ORLANDO PROPERTY ADVISORS (407-808-3695)

Listing Agent: Justin Pekarek (407-808-3695)

Remarks: Under contract-accepting backup offers. Offering 25k 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: Under Construction. Step into a world where the timeless charm of Old Winter Park meets the pinnacle of modern luxury designed by Winter Park Design and masterfully crafted by renowned builder Vimaro Homes. Nestled on one of Winter Park’s most coveted tree-lined streets, this stately home immediately commands attention with its double-entry driveway, framed by manicured landscaping and a sense of grandeur like no other. Inside, the home unfolds across more than 3,600 square feet of impeccably designed living space, with every room telling a story of quality, craftsmanship, and comfort. Rich herringbone hardwood floors stretch throughout the residence, complemented by bespoke millwork, and soaring ceilings. At the core of the home, the designer chef’s kitchen is a true showpiece, crafted for culinary excellence and effortless entertaining. Outfitted with top-of-the-line stainless steel appliances, custom cabinetry with designer hardware, and striking quartz countertops, the space is as functional as it is beautiful. A large island provides a natural gathering place, while an adjacent walk-in pantry offers seamless storage and prep. The primary suite is a retreat unto itself; a serene oasis tucked away for ultimate privacy. The spa-inspired en-suite bathroom rivals the finest resorts, featuring a soaking tub, walk-in shower with rainfall fixtures, designer lighting, dual vanities with custom cabinetry, and luxurious stone finishes throughout. A large, custom walk-in closet completes this elegant retreat. Beyond the main living areas, this home offers unique and thoughtfully designed spaces that elevate everyday living including a dedicated home office, a spacious loft, and a grand 3rd floor bonus room. Outdoors, a resort-style pool, covered lanai, and fully equipped summer kitchen create a private haven for year-round entertaining under the Florida sun. For the car enthusiast, this home offers a perfect fusion of elegance and functionality with a stately porte-cochere, a detached garage connected to the home by a breezeway, and an expansive motor court ideal for guest parking or showcasing a prized collection. Every element of this home speaks to impeccable taste and thoughtful design, from the curated finishes and luxury fixtures to the breathtaking architecture and designer lighting. Located just moments from Park Avenue, Rollins College, and Winter Park’s finest shopping and dining, you are truly in the heart of it all. More than a residence, this is a rare architectural masterpiece by Vimaro offering an unmatched lifestyle in the heart of one of Central Florida’s most coveted neighborhoods.

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

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

Remarks: Under contract-accepting backup offers. Discover the perfect canvas for your dream home at 1960 Winter Park Road! With utilities and sewer connected, plus a complete roof replacement in 2019, newer gutters with gutter guards added in 2020, and various new appliances and thoughtful upgrades since, this ¼-acre lot presents the ideal opportunity to either build new, or remodel. Zoned for the highly esteemed Audubon K-8 School, this property offers an ideal location nestled in one of the most coveted pockets of Winter Park. Stroll down the brick-lined street and land at East End market, Kelly’s Homemade Ice Cream, and all the shops and restaurants along the vibrant Corrine Drive corridor; walk around the corner to Blue Jacket Park; or venture North just 2.5 miles to discover the cultural delights of Park Avenue in downtown Winter Park. The existing 1940's home is still bursting with charm and potential. From the moment you arrive, the circular paver driveway and inviting front porch set the tone for a home that balances warmth and functionality. The main residence offers 2 bedrooms and 2 bathrooms across 1,500+ square feet, complemented by a detached 1-bedroom, 1-bath guest cottage. Ideal for extended stays, a private office, hobby space, or flexible living arrangements, the detached cottage presents endless possibilities, with enough space available for creative modifications to suit your needs. A paver 2-car parking pad off the circular drive allows room for temporary or long-term guests, with the added convenience of private entry to the detached dwelling via a paved walkway through the side gate. The main home is well-laid-out, with multiple living & dining spaces to make everyday living and entertaining a breeze, all anchored by hardwood flooring throughout. A spacious, paver side patio and large rear deck offer separate, gated outdoor living areas for versatility and enjoyment, while the rear deck overlooks a private, fenced-in backyard just waiting to be transformed into the perfect Florida oasis. If you are looking to land just a few minutes from downtown Orlando and downtown Winter Park, with easy Access to I-4…this is the location for you!

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

Listing Agent: Marystuart Day (407-620-8683)

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

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

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

Remarks: 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)