Homes For Sale in Winter Park 32792 - 179 homes

Remarks: You'll fall in love with this charming one-story Winter Park condo located in the back of Cedarwood Village where it is quit and traffic free. You can tell how meticulous the owners are as soon as you walk in. This beautiful home has an updated kitchen with granite countertops. Bathrooms and the wet bar in the dining room have also been updated with the same cabinets and granite as the kitchen. There is an eat-in kitchen area with slider access to the private patio. Washer and Dryer closet is adjacent to the kitchen. Tile floors in the main living area are tile and the bedrooms are wood floors. Split floor plan. The home has been completely painted inside. The large dining room and living boast high vaulted ceilings with skylights to add more natural lighting. There is a wood burning fireplace in the living room. French doors from the living room open up to the 27-foot tiled and enclosed lanai, under roof. The guest bedroom has access to the guest bathroom. The primary bedroom has sliders for access to the lanai. Primary bedroom has a tub and a shower. Plumbing updated. AC 2008. New duct work installed in 2023. Sellers are providing a $4,500 Credit at Closing to Buyers for a new AC. Roof 2018. Tired of weekly yard work? Your worries are over at Cedarwood Village because the lawn maintenance is included in your HOA. There are two assigned parking spaces in front of your home. Cedarwood Village amenities include a pool and tennis courts. Great School District. Great Location. Tenants will be moving out May 31, 2026.

Listing is courtesy of: WEICHERT REALTORS HALLMARK PROPERTIES (407-644-5385)

Listing Agent: Jeff Stewart (407-247-9762)

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

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

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

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

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

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

Remarks: Welcome to this fantastic home on beautiful Lake Florence in a great Winter Park location off of Howell Branch Road in Seminole County! This spacious 3-Bedroom, 2-Bathroom house features vaulted ceilings, wood burning fireplace, ceiling fans, and wonderful outdoor areas. The Living Room, Dining Room and Great Room make this home feel large. The main living areas, hallways and one bedroom have engineered hardwood flooring, wet areas have tile flooring and there is carpet in the primary bedroom and bedroom 3. There is also a small nook that would be perfect for a craft area, office or library and it opens to the side courtyard which is fully fenced and a good size storage shed for your convenience. The Kitchen has all standard appliances including refrigerator, range, dishwasher and disposal. There is also a cozy eat in breakfast nook. The Primary Bedroom is located in the back of the home and has a nice walk-in closet with en-suite bath. There are sliding glass doors that open to the huge screened-in patio with optimal views of the lake! You will love to wake up to the gorgeous view! There are two additional Bedrooms and Full Hall Bathroom. Each bedroom has direct access to the screened in porch. This home has a finished two car garage with opener and washer/dryer hookups. Enjoy coffee in your hammock while watching the ski boats inside the screened patio that runs the full rear length of the home, providing the amazing view to the lake and is perfect for entertaining or enjoying an evening cocktail. Close to most major roadways, this home will not last long!

Listing is courtesy of: COLDWELL BANKER VANGUARD EDGE (800-948-0938)

Listing Agent: Jodie Ma (407-221-0775)

Remarks: Under contract-accepting backup offers. Recently Improved to $259,900 - One of the BEST Values in Winter Park !! Welcome home to this spacious two-story Winter Park condo located in the sought-after Cedarwood Village community. Tucked away among mature landscaping yet close to everything, this residence offers a comfortable blend of privacy, architectural character, and convenience in a prime Central Florida location. The main living area features soaring 16.5-foot vaulted ceilings, a wood-burning fireplace, and sliding glass doors that lead to a screened rear porch, creating a seamless indoor-outdoor connection. Two skylights and a second-story loft overlooking the living room add architectural interest and flexible space ideal for a home office, reading nook, or guest retreat. The thoughtfully designed split floor plan enhances functionality and privacy. Additional highlights include a spacious kitchen with breakfast bar and island, a primary suite on the main level, and a screened back porch perfect for relaxing or entertaining. Community amenities include a swimming pool and tennis courts, supporting a low-maintenance, active lifestyle. Located just minutes from Rollins College, with convenient access to local retail shopping, dining, and everyday conveniences, this home is also a short drive to downtown Orlando, offering easy access to museums, theaters, and a variety of local events—combining the charm of Winter Park with excellent city connectivity. All measurements and information should be verified.

Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)

Listing Agent: Sarah Doyer (386-490-7677)

Remarks: Welcome home to this beautiful starter home or perfect student housing in Winter Park! Two story townhouse style condo with 2 bedrooms each with private full ensuite bathroom and an extra half bath on the main floor. Renovated with stone counters and all luxury plank flooring- no carpet! New appliances and a nice open kitchen with breakfast bar- very unusual in this development. Washer and dryer in unit. Private fenced back patio with outdoor storage and small front garden for your green thumb. Only 15 min to UCF, 5 min to Full Sail and near all major shopping and dining including COSTCO, Target, Publix and more. Winter Park schools.

Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)

Listing Agent: Steven Koleno (804-656-5007)

Remarks: ***WINTER PARK **** 4 BEDROOMS ****3 BATHROOM **** PAID OFF SOLAR ***** WILL HELP BUYER****METAL ROOF ***1/3 ACRE*** Welcome to 1923 Linden Rd, Winter Park—a well-maintained single-story residence offering space, character, and an exceptional location. Built in 1955, this solid masonry and concrete block home features 4 bedrooms, 3 full bathrooms, and approximately 2,117 heated square feet, with 2,281 total building square feet. Located in the highly desirable area of Winter Park, the home provides convenient access to shopping, dining, parks, and top-rated schools, as well as nearby Park Avenue and downtown Orlando. The interior offers a functional layout with multiple living areas, ideal for both everyday living and entertaining. Original character elements such as plaster interior walls and two fireplaces add warmth and timeless appeal. The centrally located kitchen provides ample workspace and flows seamlessly into the main living areas. Situated on a generous 0.315-acre lot (13,717 sq ft) with approximately 117 feet of frontage and 114 feet of depth, the property offers plenty of room for outdoor enjoyment, future enhancements, or expansion. Additional features include Metal Roof that allows for 20 degrees cool, continuous footing foundation, and package cooling system. A strong opportunity for buyers seeking a well-built home with character, space, and long-term value in a prime location.

Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)

Listing Agent: Milton James (407-572-4458)

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: One or more photo(s) has been virtually staged. Move-in ready 3-bedroom, 2-bath townhome in desirable Winter Park featuring recent exterior paint and a clean, modern presentation throughout. BRAND NEW water heater, A/C replaced in 2021, and NEW ROOF (2026). The spacious family room sits beneath dramatic two-story vaulted ceilings highlighted by tongue-and-groove ceiling planks, creating an open and architectural focal point. The functional layout includes a large bedroom and full bath on the main level—ideal for guests, a home office, or multi-generational living. Upstairs, two additional bedrooms share a Jack-and-Jill style bath, offering privacy and efficiency. The kitchen opens to the dining and living areas, making the space well-suited for everyday living and entertaining. Sliding doors lead to a screened-in patio and a private, white PVC-fenced yard—low maintenance and perfect for relaxing or pets. Additional features include wood-look flooring in main living areas, neutral finishes, and abundant natural light. Conveniently located near Winter Park shopping, dining, parks, and major roadways. A strong option for buyers seeking space, location, and low-maintenance townhome living.

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)

Listing Agent: David Fraser (407-920-9749)

Remarks: Priced to sell and move-in ready TODAY. This completely updated 2-bedroom, 2-bathroom, 1,088 sq ft ground-floor condo in the heart of Winter Park is the opportunity buyers and investors have been waiting for. At $105,000 (special assesment to-be-paid by buyer) in the 32792 zip code, it will not last. Step inside to brand-new marble-look porcelain tile flowing through every room, no carpet anywhere. The modern gray paint palette gives the entire unit a clean, contemporary feel. The kitchen features stainless steel appliances including a glass-top range, built-in microwave, refrigerator, and dishwasher, plus bright cabinetry and dark countertops. The spacious master bedroom includes a ceiling fan and sliding glass doors that open to a private patio. The second bedroom boasts a charming bay window that floods the room with natural light, ideal as a guest room or home office. Both bedrooms include generous closet space. Two full bathrooms, each with a walk-in shower and updated fixtures. In-unit stacked washer and dryer included, no shared laundry, no trips outside. Sliding glass doors from the living area open to your own ground-floor patio for true indoor-outdoor Florida living. The community features a resort-style pool, hot tub, and covered pavilion just steps from your front door. Minutes from Park Avenue, Rollins College, Winter Park Village, the SunRail station, and easy access to I-4 and 417. First-time buyer, investor, or snowbird, this is your move. Turnkey, updated, and priced below market. Schedule your showing today or buy with confidence sight unseen.

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

Listing Agent: Alex Cheikh-Khalil (407-849-8967)

Remarks: Fantastic end unit with enclosed Florida Room in the sought after Windward Square! This 3/2 features several updates including a, updated kitchen with 42" wood cabinets, granite counters and a center island! Most rooms have upgraded ceiling fans from Dan”s Fans with a lifetime guarantee. The home has newer A/C, high impact windows and the home has been re-piped for your peace of mind. This is a wonderful space and great to prep for a dinner party! Open floor concept with dining room and family room. Enclosed Florida room with high impact windows is great extra living space marking this home just over 1700sf. Master bedroom is a good size with walk in closet. Secondary rooms are spacious and full 2nd bath. You have a wonderful front fenced courtyard and a nice sized fenced back yard. End unit and 2 assigned car parking spaces. Community features low HOA and community pool, gated back entrance for easy access to Semoran, tennis courts and club house. Zoned for great Seminole County schools and minutes to shopping/dining, Altamonte Springs Mall, Downtown Winter Park, Full Sail University and to UCF. This is a great one level townhome with very reasonable HOA.

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

Listing Agent: George Freelove (407-408-5167)

Remarks: Under contract-accepting backup offers. Welcome home to this darling, move-in-ready Winter Park gem! Perfectly suited as a starter home or investment opportunity, this beautifully remodeled 3-bedroom, 1-bath residence features laminate flooring throughout, a fully remodeled bathroom, and an updated kitchen with granite countertops and stainless steel appliances. Updated plumbing completed in 2014 and a 2017 AC system offer added peace of mind, and tasteful window treatments are already in place. Step outside to a large, fully fenced backyard complete with a fire pit and shed—perfect for entertaining, relaxing, or enjoying Florida evenings. Ideally located in a great area of Winter Park, close to shops, dining, and approximately 30 minutes to everything you want to enjoy in Orlando. One of the best-priced remodeled homes in the area—this charming property is a must-see! NO HOA! Tour this home at

Listing is courtesy of: BHHS FLORIDA REALTY (407-876-2090)

Listing Agent: Catherine Lambert Pa (407-908-2525)

Remarks: Beautiful, move-in ready townhouse located in the highly desirable area of Winter Park. This well-maintained home offers comfort, convenience and a versatile layout perfect for modern living. Featuring a spacious 2 car garage and a flexible 4the room on the first floor, ideal for a home office, guest bedroom or additional living space. Enjoy being just minutes from shopping, dining and everyday essentials, all while living in a quiet and attractive community. This home is the perfect blend of style, functionality and location. Ready for its next owner.

Listing is courtesy of: TRANSCONTINENTAL REALTY GROUP, (407-401-8522)

Listing Agent: Sylvia Marchese (407-401-8522)

Remarks: You'll love this single-owner gem in Winter Park! Step inside to a traditional foyer, which welcomes you into a formal living room with excellent natural light and great flow into the dining room. Adjacent, you'll find the centrally located, spacious kitchen which overlooks your family room! A true split plan, the primary bedroom and oversized suite are on one side of the home and the two secondary bedrooms and hall bathroom are on the other. Out back, the real "heart of the home" is the generously sized back porch overlooking an original swimming pool! Solidly built block construction on a slab foundation, this 70s home will have you saying "they just don't make them like this anymore"! The major systems have been carefully updated over the years and the next owner will appreciate the peace of mind that a 2019 roof and 2018 HVAC system provide. The laundry is located in the two-car garage.

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

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

Remarks: Under contract-accepting backup offers. CALLING FOR HIGHEST AND BEST OFFERS BY MONDAY, APRIL 20th at 9:00 AM. Tucked away on a quiet street in the heart of Winter Park, this fully renovated 4-bedroom, 2.5-bath pool home—enhanced by fully owned solar panels—offers a rare blend of privacy, thoughtful design, and effortless indoor-outdoor living. Set on a generous ¼-acre lot, every detail has been curated to create a home that feels both elevated and family-friendly. Inside, the home opens to a flowing layout ideal for both everyday living and entertaining. Wide-plank luxury vinyl flooring, designer tile, and a soothing, modern palette create a cohesive sense of calm throughout. The kitchen is both a statement and a gathering place, featuring an oversized island wrapped in Taj Mahal quartzite, stainless steel appliances, and a custom wine bar—designed for connection, conversation, and celebration. Adjacent to the kitchen, the sunroom is a showstopper bathed in natural light and enhanced with custom built-ins, this versatile space effortlessly transforms into a home office, playroom, or entertainment lounge. This is where this home comes alive; perfect for large gatherings. The primary suite offers a serene retreat, highlighted by a fully remodeled spa-inspired bathroom with a soaking tub and a sleek, modern shower; inviting you to slow down and unwind. Outside, the newly added 800-square-foot turf play area, side yard, and green space surrounding the pool create room to play, entertain, and relax. The cul de sac and backyard feel exceptionally private, quiet, and peaceful. Just minutes from Park Avenue, you are surrounded by boutique shopping, acclaimed dining, lakeside strolls, and a lifestyle that feels both vibrant and relaxed. From morning coffee runs to evening walks under oak-lined streets, this is the essence of Winter Park living. This home is more than move-in ready—it’s a place to gather, grow and live. ROOF (OCT. 2022) HVAC (2017) WATER HEATER (2016) PLUMBING (2020) ELECTRICAL (UPDATED 2026) POOL PUMP/MOTOR (2020), POOL RESURFACED (2017) DRAIN SYSTEM: FRENCH DRAINS, SUMP PUMPS, GUTTERS (2024)

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

Listing Agent: Rebecca Bininger Junod (407-230-3650)

Remarks: Welcome to 2052 Leanne Ct, a home that exudes warmth and elegance. The living room is graced with a cozy fireplace, perfect for those chilly evenings. The kitchen is a chef's dream, boasting all stainless steel appliances for a sleek, modern look. The primary bedroom is a haven of comfort with double closets for ample storage. The primary bathroom is a sanctuary with double sinks, providing ample space for your morning routine. The fenced-in backyard provides a private outdoor space for relaxation and entertainment. The home has been recently updated with fresh interior and exterior paint, giving it a clean, refreshed look. New flooring throughout the home adds a touch of sophistication and durability. The new appliances ensure efficiency and convenience. Included 100-Day Home Warranty with buyer activation

Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)

Listing Agent: Karen Albright (480-462-5392)

Remarks: This beautifully renovated Winter Park home feels warm, inviting, and easy to love. Bright natural light highlights a brand-new kitchen with modern appliances, a waterfall countertop, and soft wood finishes. Both bathrooms have been transformed with elegant marble look tile and spa style showers. You’ll fall in love with the large private backyard, perfect for summer barbecues, outdoor entertaining, play space, or even adding your own backyard oasis. All of this with no HOA and close to top rated Winter Park schools, popular dining, shopping, and parks. This move-in ready home offers lifestyle, comfort, and value you have to see in person, so schedule your showing today before it’s gone!

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

Listing Agent: Lesly Hijar (321-347-7383)

Remarks: This beautifully updated 4-bedroom, 2-bath bungalow with a 2-car garage sits on a quiet cul-de-sac and underwent a major renovation in 2023. Nearly every big-ticket item has been replaced, including the roof, A/C, water heater, and double-pane windows-giving you peace of mind for years to come. The home also features a fully updated kitchen with new cabinets, countertops, and a complete appliance package—refrigerator, dishwasher, range, range hood, and microwave—along with new carpeting, ceiling fans, and a new front door. Inside, the spacious family room includes custom built-ins, offering an abundance of storage. Both bathrooms have been tastefully remodeled. The primary bath features a beautiful walk-in shower and dual sinks, while the guest bath offers dual sinks, a jetted tub, a linen closet, and convenient access to the pool area. Step outside to an oversized, fully fenced backyard where you’ll find a sparkling screened-in pool and a large covered patio with an extended overhang—perfect for relaxing or entertaining year-round. And best of all…No HOA! Conveniently located minutes from Downtown Winter Park, key highways, shopping and within an hours drive of all the major theme parks and Orlando International Airport. Welcome Home!

Listing is courtesy of: REAL LIVING R E SOLUTIONS (407-253-1377)

Listing Agent: Lynn Roeder (407-758-8565)

Remarks: Under Contract. Backup offers welcome.Welcome to 2814 Sheriff Way, an exceptional residence nestled in the vibrant neighborhood of Winter Park Pines. This remarkable home combines comfort and elegance, offering a tranquil lifestyle with unparalleled convenience. Spanning 1,948 square feet, this property boasts four generously sized bedrooms and two bathrooms (both showers renovated 5/25) perfect for family living or entertaining guests. As you step inside, you'll be welcomed by a spacious living area that effortlessly transitions into the dining space, creating a warm and inviting setting for gatherings and family meals. The kitchen is thoughtfully designed for both functionality and efficiency, ready to cater to all your culinary needs. Additional living areas include a sunroom back porch and a screened-in carport, providing versatile spaces for relaxation or entertainment. The home is perfect for entertaining, with a rear sunroom/porch, pool, offering a personal oasis for unwinding or hosting friends and family. This outdoor retreat is destined to become a favorite spot for relaxation and enjoyment. The 2-car carport with a screen creates another space to entertain. Located just minutes from Cady Way Trail, Ward Park, Cady Way Community Pool, Lake Baldwin Dog Park, Winter Park Pines Golf Club, and the iconic Park Avenue, this home is perfectly positioned for both convenience and leisure.

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

Listing Agent: Angela Carney (407-760-9822)