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

Remarks: Set on an approximately one-quarter-acre homesite in a desirable Winter Park location, this property presents an exceptional opportunity to build a custom residence in one of Central Florida’s most sought-after communities. The existing property features a one-story pool home offering approximately 2,723 heated square feet with four bedrooms and three baths; however, the value is primarily in the land. A brick-paver circular driveway enhances the property’s curb appeal, while the generous lot size provides ample space to create a beautifully tailored new construction home. Ideally located just minutes from the vibrant shopping, dining and community events of downtown Winter Park and Park Avenue, the property also offers convenient access to downtown Orlando, major area hospitals, Orlando Executive Airport and Orlando International Airport. Zoned for highly regarded Audubon K-8 and Winter Park High School.

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. 3 bedrooms PLUS an office (or 4th bedroom) AND a "flex space". Easy access to all of Winter Park, UCF, and south Seminole County from this convenient, central location! If you've been searching for a spacious pool home with plenty of space for playing, entertaining, or even working from home -- you've found it here! When you walk in, you'll appreciate the intuitive flow of living space into the kitchen, with built-in eating space. Off of the kitchen, you'll find a bonus space (perfect for an office or home gym) as well as a large indoor laundry room/mudroom, and the converted garage which is ideal for a playroom or secondary living space. On the other side of the home, 2 secondary bedrooms, an oversized hall bathroom, and a primary with en suite bath. There are additional touches that go a long way, too, including the custom plantation shutters throughout the home and updated countertops in the kitchen. Much of your time will be spent in the backyard, enjoying a fenced in pool, screened porch, new custom shed (2025), and fully fenced yard with turf play area. Systems in the home have been well maintained: roof (2017), HVAC (2017), tankless gas water heater (2018), and brand new electrical updates (2026). The home was also re-plumbed in 2008.

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

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

Remarks: This stunning new contemporary residence, a five-bedroom, five-and-a-half bath home by the renowned Rex-Tibbs Development, a custom builder for over 40 years, continues to set the standard for luxury living. Perfectly situated on a premium, quiet, charming brick street, the home blends clean architectural lines with timeless finishes and thoughtful design details. An elegant foyer immediately introduces the home’s refined aesthetic, offering a direct line of sight to the gorgeous herringbone white oak floors in the great room and the sparkling pool just beyond the full glass doors. Anchored by a sleek linear gas fireplace with custom built-ins and floating shelves, the great room provides an inviting yet sophisticated gathering space. The open-concept chef’s kitchen is a showpiece in both form and function. Outfitted with Wolf and Sub-Zero appliances, it boasts an eight-burner range with one-and-a-half ovens, an oversized Sub-Zero French door refrigerator with a freezer drawer, a built-in microwave drawer, and a walk-in pantry featuring a wine and beverage tower. Marble counters in all baths continue the home’s commitment to refined finishes. The main level primary suite is a serene retreat with a spa-inspired bath featuring a large glass-enclosed shower, separate soaking tub framed by dramatic four-by-ten-foot porcelain slabs, a custom walk-in closet, and a private water closet. A flexible fifth bedroom with an ensuite bath offers the perfect option for an office or den. A striking glass-railed staircase leads to the second level, where a spacious lounge area opens to a private covered patio. Three additional ensuite bedrooms, each with custom closet systems, complete the upstairs living quarters. Designed for indoor-outdoor living, the expansive covered lanai includes a summer kitchen with a grill, hood vent, refrigerator, sink, and a dedicated half bath. Overlooking lush landscaping with tropical Clusia hedges and Foxtail palms, the brand-new pool is finished with designer tile that lends a stylish, resort-quality flair. Additional highlights include a spacious storage closet under the staircase, oversized two-car garage, 500-gallon propane tank for easy generator connection, stone paver driveway and durable metal roof. Wonderfully located in a picturesque neighborhood, the property is just minutes from the boutiques and dining of Park Avenue, top-rated public and private schools and offers convenient access to downtown Orlando, the attractions, as well as area airports. A rare opportunity to own a newly constructed home of such quality and craftsmanship in one of Winter Park’s most sought-after neighborhoods.

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

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

Remarks: PRICED BELOW APPRAISAL, CUSTOM BAREFOOT BROTHERS HOME IN WINTER PARK. Finding a truly CUSTOM-BUILT home in Winter Park is rare. Finding one built this recently—with this level of craftsmanship, infrastructure, and thoughtful design—is even rarer. Built by Barefoot Brothers in 2014 and thoughtfully designed for an active family that values entertaining, work-from-home flexibility, and elevated everyday living, this exceptional 5-bedroom, 3.5-bath residence (currently configured as 4 bedrooms + dedicated office) offers a level of quality that simply cannot be replicated at this price point. Just minutes from Park Avenue, Audubon Park, dining, shopping, and top Winter Park amenities, the location is as compelling as the home itself. This residence delivers the rare combination of TIMELESS ARCHITECTURE + MODERN CONSTRUCTION. Built using INSULATED CONCRETE FORM (ICF) CONSTRUCTION, the home offers exceptional durability, energy efficiency, and a remarkably quiet interior—creating a true retreat from outside noise and Florida heat. Average summer utility bills are approximately $185/month. The exterior was freshly repainted in 2023, further enhancing the home’s curb appeal and long-term maintenance appeal. The floor plan was intentionally designed for real life. The FIRST-FLOOR PRIMARY SUITE serves as a private retreat with an attached office, custom walk-in closet with hidden under-stair storage, and a spa-like bath featuring dual sinks, marble vanity, freestanding cast iron soaking tub, marble floors, and an oversized walk-in shower with dual shower heads. A separate downstairs office easily functions as a fifth bedroom if desired. At the center of the home, the chef’s kitchen was built to perform as beautifully as it looks with MARBLE COUNTERTOPS, WALNUT ISLAND, GE CAFÉ GAS RANGE, BOSCH DISHWASHER, BRAND-NEW SAMSUNG REFRIGERATOR, and an oversized walk-in pantry/butler’s pantry. The adjacent living room is equally impressive with extensive custom built-ins, gas fireplace, library shelving, surround sound wiring, and French doors opening seamlessly to outdoor entertaining spaces. Designed with entertaining in mind, the outdoor spaces feel like an extension of the home with a spacious river rock patio, covered breezeway with tongue-and-groove ceiling, natural gas hookup for grilling, detached rear-entry two-car garage, circular front drive, and additional rear parking—an uncommon luxury in this highly sought-after location. Upstairs, soaring ceilings frame a large bonus/playroom alongside three additional bedrooms and two baths, including a Jack-and-Jill layout. A climate-controlled attic space under AC offers valuable bonus storage not included in the home’s stated square footage. Additional upgrades include NATURAL GAS (range, fireplace, dryer & grill), TANKLESS WATER HEATERS, CAT 6 ETHERNET WIRING, QUANTUM FIBER READINESS, and LOW-E DOUBLE PANE WINDOWS. Every inch of this home was intentionally designed with longevity, comfort, and function in mind. Try building this level of fully custom home in Winter Park today—on this timeline, with these finishes, this infrastructure, and this location—at this price point. It’s nearly impossible. Homes of this caliber rarely become available, especially PRICED BELOW APPRAISAL. Schedule your private showing and experience firsthand what makes this Winter Park home so exceptional.

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

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

Remarks: Experience timeless elegance and deliberate craftsmanship in the heart of prestigious Winter Park. This one-of- a-kind exceptional estate offers more than 7,300 square feet across three beautifully designed levels, blending refined luxury with modern comfort. Rich architectural details include solid red oak flooring with a walnut finish, nearly 10-foot ceilings, stacked crown moldings, custom ironwork, designer lighting, and extensive millwork throughout. The gourmet kitchen is thoughtfully appointed with Viking and GE Monogram appliances, custom Busby cabinetry, an oversized island, and a butler’s pantry. It also includes multiple filtered water and ice zones designed for effortless entertaining. The spacious primary suite offers a true retreat with spa-inspired marble finishes, an oversized walk-in shower, a jetted soaking tub, and exceptional custom closet space. Additional features include a private elevator, Control4 automation, integrated audio/video/security systems, five HVAC systems, a central vacuum system, and a Generac whole-home generator. A fully finished and expansive basement level serves as a unique and exceptional extension of the home’s living and entertaining space. Designed for both relaxation and recreation, it features a game and arcade room, a full beverage center with a dishwasher, microwave, and Scotsman ice machine, a fitness area with a sauna and steam room, an additional laundry room, a creative storage center, and a private 4K theater with seating for multiple guests. Outdoors, resort-style living awaits with a saltwater pool and spa, a summer kitchen with a custom copper hood, an electric gated entry, landscape lighting, lush cascading bougainvillea, and ten mature magnolia trees creating exceptional beauty and privacy. The property also features a dog run with artificial turf. Three ventless gas fireplaces, including one on the private covered porch, add warmth and ambiance throughout the home. This home also features a whole-house water softener system. Top-rated A+ public schools are within a short walk or bike ride. Nearby highly regarded private schools include Park Maitland School, The Christ School, The First Academy, Trinity Preparatory School, Lake Highland Preparatory School, and Bishop Moore Catholic High School. Perfectly positioned within walking distance of the boutiques and dining of Park Avenue, and just minutes from the Winter Park Golf Course, Rollins College, and Advent Health Winter Park, this is a rare opportunity to own an exceptional custom estate in one of Central Florida’s most sought-after communities.

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

Listing Agent: Vonda Fields (321-438-6906)

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

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

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

Remarks: Repositioned at $2,850,000, 151 Oakwood Way is one of the strongest newer luxury opportunities under $3M in Winter Park. Built by LunDev Custom Homes in 2023, this 4,129-square-foot residence sits on a quiet brick street in Charmont and offers a private pool, spa, covered lanai, summer kitchen, automatic screens, and a rare under-$700/sf position for newer luxury construction in 32789. Inside, the home features wide-plank wood flooring, high ceilings, quartz surfaces, Thermador appliances, custom built-ins, a wet bar, walk-in closets, and an open kitchen, dining, and living layout filled with natural light. The main living areas connect directly to the outdoor entertaining space, creating the indoor-outdoor flow buyers want in Winter Park. The floor plan includes 4 bedrooms, 4.5 baths, a main-level primary suite, generous secondary spaces, and a large flex room that can function as an office, family room, media room, game room, or future guest suite, with plumbing already in place. Set on a landscaped 0.26-acre lot with no HOA shown publicly, 151 Oakwood offers a compelling combination in 32789: newer LunDev construction, private pool, outdoor kitchen, brick-street setting, and a sub-$3M position close to Winter Park, Baldwin Park, Audubon Park, and Park Avenue.

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

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

Remarks: Under contract-accepting backup offers. Nestled behind gates in the heart of Winter park, this enchanting 1930's residence blends historic charm with many recent upgrades. The beautifully renovated kitchen anchors the home, while the downstairs primary suite offers privacy and comfort with an elegant spa inspired bath. The detached one bedroom guest house is perfect for houseguests, a home office or multi-generational living. The main house has a flexible floor plan that includes four bedrooms and four and one half baths, a sunroom ideal for home office, formal dining room, oversized family room and charming sitting area with fireplace. The kitchen is a chef's delight with six burner gas range, large center island, plentiful l space for gatherings and a separate breakfast room. Other notable features include gleaming wood floors, double pane windows offering abundant natural light, adorable laundry room/mud room. French doors from many rooms open to a classic front porch that is a perfect place for relaxing and enjoying picturesque grounds with towering oaks. Step outside to a private heated pool. Detached garage includes Tesla charging station. This gated compound situated on .42 acres is one block from Lake Osceola and a easy walk to Park Avenue.

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

Listing Agent: Nicole Seybold (407-808-9374)

Remarks: Under contract-accepting backup offers. Set on an oversized 1/3-acre lot in the heart of Winter Park, this one-owner home was custom built in 1997 and has been meticulously maintained ever since. Solid block construction, timeless stone accents, and mature landscaping give it great curb appeal from the moment you arrive. Step inside to a spacious foyer with hardwood floors that carry through most of the main living areas. To the right, the living room features built-in shelving and a bay window that fills the space with natural light. It flows into the formal dining room, also with hardwood floors, plantation shutters, and plenty of room to host. A conveniently located powder bath serves this side of the home. To the left is the heart of the house - a generously sized kitchen with abundant white cabinetry, stone countertops, a center island, double ovens, a built-in pantry with pull-out storage, and a breakfast bar. The separate eat-in area overlooks the backyard and opens to the screened porch through French doors. The kitchen connects to a large family room with coffered ceilings, a gas fireplace, built-ins, and additional French doors leading outside. The home offers a three-way split floor plan for privacy. The primary suite sits on its own wing and is very spacious, featuring crown molding, a bay window, and French doors to the patio. The en-suite bath includes double vanities, large "His & Hers" walk-in closets with custom closet systems, a soaking tub, separate shower, and private water closet. On the opposite side of the home, you’ll find a generously sized secondary bedroom with its own en-suite bathroom and walk-in closet. Toward the back of the house is a third bedroom with a built-in desk, French doors to the exterior, and an en-suite Jack-and-Jill bath that also serves the family room. The first floor also includes an indoor laundry room with ample cabinetry and a utility sink. Upstairs, a huge bonus room offers incredible flexibility - game room, media room, office, or potential fourth bedroom. There is also space to add a bathroom if desired. Out back, a large screened porch with high ceilings overlooks a peaceful, lushly landscaped yard with plenty of room to enjoy Florida living. Additional features include plantation shutters throughout, a spacious two-car garage, and an unbeatable location just minutes from Park Avenue’s shopping and dining. Zoned for highly rated Dommerich Elementary, Maitland Middle, and Winter Park High. Call today to schedule your private showing!

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

Listing Agent: Maria Van Warner (407-256-8066)

Remarks: Under contract-accepting backup offers. 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)

Remarks: ? FULLY REMODELED WINTER PARK POOL HOME NEAR BALDWIN PARK! ? Welcome to 1946 Strathaven Road — a beautifully updated 4-bedroom, 3-bath home with a dedicated office, ideally located near both Winter Park and the highly sought-after Baldwin Park community, known for its lakeside dining, walkability, parks, boutiques, and vibrant neighborhood atmosphere. ? This move-in ready home features an open and light-filled layout with designer finishes throughout, including updated flooring, custom cabinetry, modern lighting, and beautifully remodeled bathrooms and kitchen with premium appliances and upscale countertops. Major upgrades include a NEW roof (2023), windows (2023), water heater (2023), electrical panel (2023), plus updated plumbing and electrical throughout for true peace of mind. Enjoy spacious living areas, a luxurious primary suite, and a private backyard perfect for relaxing or entertaining. Conveniently located near top-rated schools, parks, shopping, dining, Park Avenue, and everything Winter Park living has to offer, this home combines modern updates with an unbeatable Central Florida location.

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

Listing Agent: Youbel Montesino (954-608-4838)

Remarks: Under contract-accepting backup offers. 1871 Bryan Avenue presents a rare opportunity to own in one of Winter Park’s most desirable pockets without the million-dollar price tag. Located in the heart of 32789 on a 50x127 lot, this charming home offers 1,210 square feet with an efficient layout ideal for a first-time buyer, downsizing homeowner, or investor looking for long-term upside in a prime location. Just minutes from Park Avenue, Winter Park Village, popular restaurants, shopping, and everyday conveniences, the lifestyle and walkability are hard to beat. Major updates include roof (2020), water heater (2026), and HVAC (2009), offering peace of mind for the next owner. Whether you’re looking to move right in, renovate over time, or secure a foothold in the Winter Park market, this property delivers exceptional potential in an unbeatable location.

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

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

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: 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)