Homes For Sale in Winter Park 32792 - 194 homes

Remarks: Welcome to easy, light-filled living in this beautifully maintained 3-bedroom, 2.5-bath corner townhome in the gated Grayson Square community. Freshly painted and designed for comfort, the open living and dining spaces feel bright and inviting, flowing effortlessly to a covered lanai—perfect for relaxing evenings or casual gatherings. The kitchen offers a clean, modern look with stainless steel appliances, quartz countertops, and plenty of cabinet space for storage and organization. Upstairs, the owner’s suite provides a private retreat with a walk-in closet and a spacious ensuite bath featuring dual vanities and a glass-enclosed shower. A two-car garage with epoxy flooring and an in-unit washer and dryer add everyday convenience. Residents also enjoy access to a resort-style pool with cabana, along with high-speed fiber-optic internet and streaming services included. Located just minutes from downtown Winter Park, with easy access to major roadways, shopping, dining, and everyday essentials, this home offers a great balance of comfort, convenience, and low-maintenance living.HABLO ESPANOL

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

Listing Agent: Denise Del Castillo (321-960-3110)

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: 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. 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: 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: One of the best patio views in this community. Enjoy easy living in this cozy, open-concept first-floor condo located in a desirable Winter Park community. Step out onto your newly screened-in patio and take in the peaceful, park-like setting — a relaxing extension of your living space and the perfect spot for morning coffee or evening unwinding. Recent 2025 improvements include a new A/C system, water heater, freshly painted interior, new screened porch, and new toilet — giving you move-in-ready comfort and peace of mind. The kitchen comes fully equipped with range, dishwasher, refrigerator, and microwave. A stackable washer and dryer are conveniently located in the bedroom, and an additional community laundry room with two washers and dryers is available free of charge. Stratford residents enjoy an amenity-rich lifestyle including: • Two sparkling pools • Tennis courts • 24/7 fitness center • Clubhouse available for private gatherings • Pet station *Planned social events for residents. The HOA adds tremendous value by covering water, trash removal, internet, pest control, exterior maintenance, grounds care, and common areas — simplifying ownership and monthly budgeting. Located in a prime Winter Park area with easy access to 408, Semoran Blvd., 417, I-4, and State Road 50. Just minutes from shopping, dining, grocery stores, and within 20 minutes of UCF, Full Sail University, Rollins College, and Park Avenue. With its thoughtful updates, first-floor convenience, and exceptional community amenities, this condo offers more than just a home — it delivers an above-average lifestyle in one of Central Florida’s most desirable locations.

Listing is courtesy of: WATSON REALTY CORP (407-332-6000)

Listing Agent: Barbara Coy (407-497-1777)

Remarks: Winter Park Clean, updated condo in Move In Condition - The newest condo's year built are located on the last street in the complex where this unit is located which features more contemporary open floor plans and high ceilings. Enjoy the One story living. No apartment living with noisy neighbors. Another BONUS is *** NO condo neighbors across the street from you - private!!** This unit is second to the end of a Quiet Dead End Street. Step into a bright and airy condo featuring laminate and tile floors. Newer painted pastel colors throughout. The updated contemporary kitchen has newer Pecan colored cabinets and newer granite counter tops with stylish designer tile back splash. Both bathrooms have newer vanities and granite counter tops. The second bath features a designer Pedestal vanity with granite top. Many upgraded finishes and fixtures throughout. Features a split bedroom floor plan that provides privacy, both bedrooms have spacious walk-in closets. *** Open living area shines with natural sun light and is open to a screened porch, providing access to the private, fenced back courtyard. This condo has a New (December 2024) High efficiency RHEEM 15.3 SEER AC unit with Heat Pump that helps keep utility costs lower, New Roof (2021), New 6 panel Front entry door January (2025), New carpet in both bedrooms installed January (2025), Replumbed with New PEX plumbing pipes, New Refrigerator (2025) New light fixtures throughout. Features an open eat in kitchen and a large breakfast bar open to living room. As a resident, you'll have access to the community pool and the convenience of being close to the Cross Seminole Trail and Cady Way Trail, Winter Park Village, UCF and Full Sail. This location offers easy access to major roadways, shopping, and dining and is served by the reputable Seminole County Schools. Complete with fenced backyard! Community has swimming pool & bathrooms. ** Exterior of the building is scheduled to be painted. ** Professionally cleaned for new owners. Never smoked in.

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

Listing Agent: Tom Bercini (407-925-4760)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Beautifully renovated pool home in the highly desirable Eastbrook community of Winter Park, featuring major recent upgrades including a new AC system, windows, doors, and flooring throughout the home. This move-in ready 3-bedroom, 2-bath residence sits on an oversized 0.30-acre corner lot in a quiet cul-de-sac with no HOA. The home offers a bright open-concept layout with abundant natural light and a seamless flow between the living, dining, and kitchen areas—ideal for both everyday living and entertaining. The updated kitchen features modern cabinetry, stainless steel appliances, and generous counter space. Both bathrooms have been tastefully renovated, and the spacious bedrooms provide comfort and flexibility. Step outside to a private backyard with a sparkling pool and plenty of outdoor space perfect for relaxing or hosting gatherings. Additional highlights include a 1-car garage, roof replaced in 2016, updated electrical, and a newer water heater (2021). Located within the top-rated Seminole County school district and just minutes from Park Avenue, Rollins College, shopping, dining, museums, and Winter Park Hospital. A fantastic opportunity to own a beautifully updated home in one of Central Florida’s most desirable locations.

Listing is courtesy of: SERHANT (786-296-8626)

Listing Agent: Julimar Barreiro Pastrana (407-590-8604)

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)

Remarks: Situated in an established Winter Park neighborhood, this single-family residence offers a functional layout with generous living space designed for everyday comfort. The home features multiple living areas that provide flexibility for daily living, entertaining, or work-from-home needs. Conveniently located near major roadways, public transit, shopping, dining, and surrounding Central Florida destinations, this property offers a balanced blend of accessibility and neighborhood appeal within Seminole County.

Listing is courtesy of: MAINSTAY BROKERAGE LLC (800-583-2914)

Listing Agent: Raquel Littlejohn (470-279-6333)

Remarks: Short Sale. Short Sale – Subject to Lender Approval. Exceptional investment opportunity in the desirable Winter Park area. This property offers strong potential for value-add through renovation or repositioning. Located in an established community with no HOA, the home sits on a generously sized lot, providing flexibility for improvements and long-term upside. The current layout presents a solid starting point for updates, making it suitable for rental income, resale, or portfolio expansion. Conveniently positioned near shopping, dining, parks, and major roadways, with access to highly regarded schools and surrounding amenities. Winter Park continues to experience steady demand, supporting long-term investment potential. Property is being sold as-is. Buyer to verify all measurements, condition, and intended use. Don’t miss this opportunity to secure a property with upside in a sought-after Central Florida location. Highest and Best due April 17th

Listing is courtesy of: DREAM HOME REALTY GROUP AND ASSOCIATES LLC (407-504-7282)

Listing Agent: Latisha Smith (407-504-7282)

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: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. You’ve just found a Gem! Immaculate, move-in ready, and so conveniently located, you’ll love this turn-key home. Just painted inside and out, featuring brand new contemporary flooring, a 2025 AC, a newer tankless hot water heater, a brand new kitchen cooktop, all new light fixtures, switches, ceiling fans, and door hardware. A new roof was added in 2018, new plumbing in 2024, and new electrical panels added in recent years. You’ll enjoy ample cabinet storage and counter space for cooking in this open kitchen, plus room for casual or formal dining. A comfortable family room area offers plenty of space for streaming shows, watching your favorite sporting event or gaming with friends. And when the weather beckons, you can start the day with a quiet morning coffee on your screened patio, or relax with your favorite drink after work as you heat up the grill to barbecue. Want to toss a frisbee with your four-legged buddy? There’s lots of room in this big backyard. Conveniently located near major employers, shopping, restaurants, medical facilities and hospitals, UCF, access to downtown and airports. Served by desirable Winter Park and Maitland schools. Attractively priced and move-in ready, this home is a winner! Come take a look and make it yours today!

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

Listing Agent: Jane Pedigree (407-782-9598)

Remarks: Welcome home! You've found it, a spacious end unit townhome style condo with private 1 car garage with extra storage space. Open floorplan first floor, when you walk in the front door you walk into a huge living room/dining room combination room with views out the back of your private screened patio overlooking a pond. The kitchen features lots of counter space, breakfast bar on the kitchen island and all appliances included! upstairs you will find a HUGE master suite with walk-in closet and ensuite bathroom with dual vanities, separate water closet and shower. Down the hall you have your indoor laundry closet, as well as two additional bedrooms with view of the pond. Easy commute to Downtown, Baldwin Park, Winter Park with quick access to the 408 and 417!

Listing is courtesy of: COMPLETE FLORIDA REALTY LLC (407-222-7281)

Listing Agent: Greg Traub (407-222-7281)

Remarks: Under contract-accepting backup offers. Under Construction. A rare opportunity to own brand-new construction in desirable Brookshire Heights, this thoughtfully designed residence blends timeless finishes with modern functionality. Featuring 5 bedrooms, a dedicated office, and a spacious bonus room, the floor plan is both highly livable and exceptionally functional—ideal for everyday living and entertaining alike. All bedrooms are ensuite, offering comfort and privacy throughout, while hardwood floors run seamlessly across the entire home. Thoughtful architectural details, including custom ceiling treatments and built-ins, add depth and character throughout. The first-floor primary suite serves as a true retreat, complete with dual shower heads and a rain shower for a spa-like experience. In addition to the primary, the secondary bedrooms and office are all conveniently located on the first floor—providing a layout that lives comfortably day-to-day. Upstairs, you’ll find three spacious bedrooms, each with its own full bath, along with a generous bonus room and a large laundry room—offering flexibility for guests, family, or additional living space. Perfectly positioned within steps to Brookshire Elementary, the home is also just moments from the Cady Way Trail, Little League fields, parks with covered pavilions, and nearby medical facilities. Shopping, dining, and everyday essentials are just minutes away, with Park Avenue’s renowned restaurants and boutiques a short drive from your doorstep. A seamless blend of location, thoughtful design, and livability, this home offers an exceptional opportunity in one of Winter Park’s most established neighborhoods.

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

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

Remarks: One or more photo(s) has been virtually staged. Welcome to this inviting 2-bedroom, 2-bathroom condo located in the desirable Lancelot at Winter Park community, offering the perfect blend of comfort and convenience for investors, first-time buyers, or anyone seeking low-maintenance living. This well-appointed unit features an open and airy layout with abundant natural light, seamlessly connecting the living and dining areas to create an ideal space for both relaxing and entertaining. The modern kitchen provides a functional workspace designed for everyday ease. Residents will also enjoy access to a community pool, perfect for unwinding or hosting guests, along with professionally maintained common areas that enhance the overall appeal of the neighborhood. Ideally situated, this condo offers close proximity to UCF and Full Sail University, making it an excellent option for rental potential, as well as convenient access to major shopping centers, dining options, and key highways including I-4 for easy commuting. Whether you're searching for a primary residence, a second home, or a strong investment opportunity, this property delivers exceptional value in a prime location. The property was previously leased at $1,625 per month.

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

Listing Agent: Christina Munkberg Bianca (407-340-1308)

Remarks: **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Nestled in the heart of Winter Park, 2224 Shadowland Loop offers a beautiful blend of comfort, style, and low-maintenance living in this spacious 3-bedroom, 3-bathroom townhouse. The interior features an inviting open layout with high ceilings, modern finishes, and tile and carpet flooring all throughout. The well-appointed kitchen flows effortlessly into the main living and dining areas, creating a seamless environment for entertaining or everyday living. All three bedrooms include generous walk-in closets, while the primary suite offers a peaceful retreat with its own private bathroom and serene ambiance. A versatile loft on the second floor adds valuable flex space that is ideal for a home office, media area, or playroom. Outside, the home offers a cozy enclosed rear patio perfect for relaxing, dining outdoors, or enjoying your morning coffee in privacy. A spacious two-car garage provides convenience and additional storage. The community surrounding Shadowland Loop is quiet, welcoming, and beautifully maintained, with tree-lined streets and easy access to the best of Winter Park. Residents enjoy proximity to top-rated schools, charming parks, boutique shopping, vibrant dining spots, and the area’s beloved lakes and recreation. With its thoughtful design, modern amenities, and exceptional location, this townhouse delivers the ideal Winter Park lifestyle.

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

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

Remarks: One or more photo(s) has been virtually staged. **This property qualifies for a closing cost credit up to $3,300 through the Seller’s preferred lender.** Welcome to this updated 2-bedroom, 2-bath first-floor condo in the heart of Winter Park. Tucked away at the back right corner of the building, this bright unit features hardwood floors throughout and an open living room with sliding glass doors leading to the community green space that is a tropical oasis. The adjacent dining area includes a stackable washer/dryer and flows into a modern kitchen with floor-to-ceiling cabinetry, granite countertops, and stainless steel appliances. Both spacious bedrooms sit near the entry, with the primary suite offering a walk-in closet and a sleek ensuite bath with a glass-front shower and floating vanity—mirrored in the newly updated guest bath as well. Enjoy low-maintenance living with access to resort-style community amenities including two pools, tennis courts, and a gym—all in a prime location! Schedule your private showing today!

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

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

Remarks: LOCATION! LOCATION! LOCATION! Beautiful 2nd floor corner condo in desirable Winter Park, featuring 1 bed/1 bath, open concept living/dining area and balcony. Move-in ready and conveniently located near UCF, Rollins College, Valencia College, Park Avenue, and Downtown Orlando. Residents enjoy resort-style amenities including two pools, tennis court, a fitness center, and clubhouse available for rental for gathering or events. The unit includes a fully equipped kitchen, stackable washer and dryer in the bedroom, and access to free community laundry. HOA covers water, trash removal, internet, pest control, exterior maintenance, and grounds care. Close to shopping, dining, and major highways for easy access across the area.

Listing is courtesy of: KELLER WILLIAMS HERITAGE REALTY (407-862-9700)

Listing Agent: Sandra Da Silva (407-840-8500)