Homes for Sale Near Winter Park High in Winter Park - 172 homes

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)

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: Come home to this gorgeous 3 Bed/3 Bath Winter Park masterpiece on a premier corner lot at the intersection of the coveted Alabama Drive and Palmer Avenue. FULLY RENOVATED DOWN TO THE STUDS IN 2020. Located in one of Winter Park’s most highly sought-after areas, the property is beautifully framed by the iconic tree-lined brick streets of the Chain of Lakes district and surrounded by historic estate homes. The Lifestyle: Central Florida's Premier Luxury Destination Living at 1110 Alabama Drive means immersing yourself in the rich culture and timeless elegance of Winter Park. This historic city is celebrated for its deep canopy oak trees, world-class amenities, and a laid-back atmosphere. A Walker's & Boater's Paradise: You are just a short, scenic stroll from the exclusive boutiques, acclaimed sidewalk cafes, and Michelin-starred dining lining Park Avenue. Spend your weekends grabbing fresh produce at the famous local farmers' market or launching a boat onto the stunning interconnected freshwater Chain of Lakes. Surrounded by Beauty: This home places you moments from the breathtaking, massive cypress trees and vibrant blooms of Kraft Azalea Gardens, as well as the private, historic Winter Park Racquet Club. The Residence: Fully Renovated & Refined No detail has been spared in this total home transformation, seamlessly blending a classic, highly coveted location with cutting-edge modern amenities. Gourmet Kitchen: Discover a massive chef’s footprint appointed with premium granite countertops and high-end finishes, making it the focal point for both daily living and grand entertaining. Designer Upgrades: Rich hardwood flooring flows effortlessly throughout the home, beautifully complemented by high-efficiency upgraded Pella windows that provide enhanced aesthetics and excellent energy savings. Modern Infrastructure: Enjoy total peace of mind with meticulously updated systems, including a 5-year-old tankless water heater, a custom-designed garage door, and a well-maintained 12-year-old roof. The Ultimate Outdoor Oasis Designed intentionally for the true Florida lifestyle, the exterior of this property serves as a completely private sanctuary. Signature Screened Porch: Step out into an expansive outdoor living space anchored by a cozy gas fireplace—serving as the ultimate venue for year-round entertaining. The Grounds: Relax by the private, open-air pool surrounded by lush, tropical landscaping and a fully irrigated lot, capturing resort-style living in your own backyard. Whether you are searching for a turnkey luxury residence or looking to secure a rare, premier canvas in Central Florida’s most coveted zip code, this estate has it all.

Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)

Listing Agent: Omar Albaba (813-951-7475)

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 151 Oakwood Way, a beautifully executed residence by LunDev Custom Homes, set on a quiet, tree-lined street in the heart of Winter Park. Blending timeless architecture with a clean transitional aesthetic, this newer pool home offers sophisticated design, comfortable livability, and the kind of indoor-outdoor flow today’s buyers are looking for. Inside, the home is filled with natural light and thoughtfully designed for both everyday living and entertaining. Wide-plank engineered hardwood flooring, quartz surfaces, premium Thermador appliances, and well-selected finishes create a refined, elevated feel throughout. The open-concept layout lives effortlessly, with inviting spaces that feel both polished and welcoming. The outdoor setting is a true highlight. A covered lanai with a summer kitchen and automatic screens opens to a beautiful saltwater pool and separate spa, creating a private, resort-style backdrop for relaxing or hosting year-round. A spacious flex room adds valuable versatility and can easily function as an office, game room, media space, or potential future guest suite, with plumbing already in place for added flexibility. Thoughtfully designed and exceptionally well located, 151 Oakwood Way presents a rare opportunity to own a newer luxury home in one of Winter Park’s most desirable settings.

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

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

Remarks: One or more photo(s) has been virtually staged. Welcome to 1036 Aragon Avenue, a charming Winter Park bungalow perfectly positioned in one of Central Florida’s most sought-after locations. Nestled along picturesque cobblestone roads and surrounded by mature, tree-lined streets, this move-in ready home captures the character and warmth that make Winter Park real estate so desirable. Located just one mile from Park Avenue, SunRail, and Rollins College, and only half a mile from Hannibal Square, local parks, and the Winter Park Library, this property offers an unbeatable blend of convenience, walkability, and lifestyle. As you step inside, you are greeted by a modern open floor plan enhanced with luxury vinyl plank flooring that flows seamlessly throughout the home. The spacious living and dining areas create an inviting environment ideal for both everyday living and entertaining. The updated kitchen serves as the heart of the home, featuring stainless steel appliances, granite countertops, and timeless white shaker cabinetry. Its thoughtful layout allows for easy conversation and connection while preparing meals, making it as functional as it is stylish. The oversized great room provides flexibility for relaxing, hosting guests, or creating a dedicated workspace. Both bedrooms are generously sized, offering comfort and versatility. The owner’s bedroom is especially appealing, complete with a custom closet organizer and direct access to a private paver patio—an ideal setting to enjoy Florida’s year-round sunshine. The bathroom has been tastefully updated with granite countertops and a shower/tub combination accented by classic white subway tile, creating a clean and timeless aesthetic. Outdoors, the secluded backyard offers privacy and future potential, with room to expand or customize according to your vision. Whether you are searching for a primary residence, a downsizing opportunity, or an investment in the heart of Winter Park, this property presents a rare chance to own a beautifully updated home in a prime location. Experience the charm, convenience, and lifestyle that 1036 Aragon Avenue has to offer. Schedule your private showing today.

Listing is courtesy of: WATSON REALTY CORP (407-359-2300)

Listing Agent: Tim Veigle (407-399-0879)

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Remarks: Tucked away on a quiet circle in one of Winter Park's most sought-after neighborhoods, this distinctive pool home offers a rare opportunity. Set on an approximately .26-acre lot, the home features striking architectural lines, soaring wood ceilings with exposed beams, polished concrete flooring, and an abundance of natural light throughout. This is the only home currently for sale in Quail Hollow. Access to top rated schools. The exterior has been comprehensively updated: both the metal and flat roof sections (2022) and dual A/C units (2022) are already behind you, along with fresh interior and exterior paint, refinished ceilings, and new carpet. The backyard is a genuine retreat — the pool deck and fencing were both redone in 2026 — with a fully fenced yard and expansive deck ready for patio furniture, a barbecue, and effortless entertaining. Inside, a flexible and spacious layout offers room to put your own stamp on a truly special property. Practical upgrades round out the package: a Level 2 EV charger in the garage, a second Level 2 EV circuit wired to the driveway, fiber optic internet connectivity, and a recent refrigerator and dishwasher replacement. Conveniently located near Winter Park's best shopping, dining, parks, and major roadways, this home combines an unbeatable location with a strong foundation of recent improvements — and real upside for the buyer ready to make it their own.

Listing is courtesy of: BREC PROPERTIES INC (407-374-9408)

Listing Agent: Caroline Borling (407-694-3871)

Remarks: Welcome to this beautifully maintained 2-bedroom, 2-bathroom condo in the heart of Winter Park! Perfectly positioned for both convenience and lifestyle, this home offers quick access to the 408 Expressway and is just minutes from Downtown Orlando, making daily commutes effortless. Step inside to discover a bright and inviting interior featuring upgraded light fixtures, and an abundance of natural light that enhances the open feel of the space. The thoughtfully designed layout includes generously sized bedrooms and a spacious living area ideal for both relaxing and entertaining. The kitchen is highlighted by a breakfast bar with new granite countertops, creating a functional and stylish focal point. This unit can be sold fully furnished, offering a true turnkey opportunity for homeowners or investors alike. All appliances are included, making for a seamless move-in experience from day one. Location is everything—and this one delivers. Just minutes from Full Sail University, University of Central Florida, and Valencia College, this property is ideally situated for strong rental potential. Plus, enjoy being within easy reach of world-famous attractions like Walt Disney World and the beautiful shores of Cocoa Beach. Whether you’re searching for a primary residence, vacation getaway, or investment property, this Winter Park gem offers the perfect blend of comfort, location, and value.

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

Listing Agent: Uzi Husain (407-719-6576)

Remarks: Price Reduction! READY TO BE SOLD! Accepting great offers. Welcome home! NEWLY RENOVATED BATHROOM on deck. Is Winter Park your destination or desire? Investment Potential, Student Sanctuary or just a long-awaited Life. Centrally located at your fingertips. Location, Lifestyle, Luxurious Zip Code, Friends, Culture and Community. Discover an unparalleled opportunity to own a piece of prime real estate in the heart of Winter Park, Florida. This beautifully appointed condo apartment is located within a vibrant, amenity-rich HOA community offering a perfect blend of convenience and value. Whether you're a first-time buyer, a savvy investor seeking strong rental return, or a student prioritizing location and community, this unit checks every box, all at an exceptional, reasonable price point. The very best luxury boutiques, fine dining, sidewalk cafes, and vibrant art festivals. Instant access to top tier schools and hospitals. A very short commute to Rollins College, Full Sail University, UCF, Valencia College and major medical centers like AdventHealth and Orlando Health facilities, making it ideal for any resident, and or faculty. Transportation is easily accessible to Downtown Orlando where the famous Lake Eola Park is, Winter Springs, Oviedo, The Orlando International Airport, Cady Way Trail, Biking, Hiking, Swimming, Volleyball, Pickleball, Tennis and Painting at The Crealde School Of Art. There's just so much within reach. Explore local gatherings, social events and community connections. For all investors, strong rental income potential and appreciation value. There's low maintenance and worry-free ownership opportunities. Let's build a portfolio together. Don't walk...run!

Listing is courtesy of: COLDWELL BANKER REALTY (407-696-8000)

Listing Agent: Cassandra Kelly Flores (347-723-4649)