Homes for Sale in Winter Park

An excellent townhouse located in Winter Park. This first-floor unit has 2 bedrooms, 2 bathrooms, and a bright living area. It also features a unique loft that can be used as an office, reading space, or an extra sitting room to fit your needs. The kitchen is equipped with granite countertops, light fixtures, wood cabinets, and appliances. Additionally, this property boasts one of the largest backyards in the community. Don't wait, schedule your appointment now as this property won't last long!

Under contract-accepting backup offers. Large two-bedroom two bath one story townhome located in popular Windward Square. Exterior has recently been painted with the new association approved colors. Community pools, clubhouse, playground. putting green, shuffleboard courts, and tennis courts are located behind the home. Private parking for three vehicles. HOA fees are $92.77 monthly. Seller will contribute $5,000 toward buyers closing cost.

Under contract-accepting backup offers. Dreams Do Come True! Welcome to your dream Villa in Winter Park! Bring your FHA, VA or DPA to this charming 2-bedroom, 2-bath, one-story townhome Villa offers recent upgrades like a new roof (2022), water heater (2020), vinyl privacy fence (2020), and a full re-pipe (2020), you can enjoy peace of mind for years to come. Offering the ideal blend of comfort and convenience. Located near Aloma and Semoran, this prime spot puts you within a short drive to vibrant downtown Winter Park, where shopping boutiques, gourmet dining, and Sun Rail access await. You’re also perfectly positioned near Maitland, Altamonte Springs, downtown Orlando, and Orlando International Airport, with Super Wal-Mart, Publix on Howell Branch, and Full Sail University right around the corner. Step inside to find a nicely maintained home featuring tile floors throughout (except in the cozy bedrooms), high-end stainless steel appliances, and a upgraded washer and dryer—all included! The spacious screened lanai is perfect for relaxing with views of the fenced backyard, and the inviting front porch makes an ideal spot for morning coffee or weekend BBQs. With an ultra-low HOA fee of approximately $55 per month, including access to the community pool, this townhome is not only an incredible place to live but also a smart investment opportunity. Hurry on this one.

*Reintroducing* 1920 Woodcrest Drive. Great location in quaint Winter Park in a beautifully manicured community! Low maintenance and worry free, this 2-bed, 2-bath condo features 1,010 square feet of living space. The open layout connects the living, dining, and kitchen areas while both bedrooms have en-suite bathrooms. The primary bathroom was remodeled in 2023. The kitchen has newer appliances and granite countertops. New roof in 2023 and brand new AC and water heater in July 2024 make this move-in ready. The community also features a pool and additional storage. Conveniently located in Winter Park near Baldwin Park and Audubon Park with easy access to dining, shopping, entertainment, and situated across the street from $1mm homes. Properties in this price point and location don't come on the market often. Schedule your showing today!

* Very CLEAN Move In Ready * The homes on the last Street in the community were the last ones built and have newer floor plans which are more open and have vaulted ceilings. All other homes in neighborhood have flat 8' ceilings and older floor plans. Located in the back of small neighborhood which offers quiet and private area on the end of a dead end Street no neighbors across the street. Upgraded unit with newer high end cabinets in kitchen and both baths, Granite counters in kitchen and baths. Custom tiled backsplash. Features a open eat in kitchen area on one end and other has a large granite breakfast bar. Spacious open floor plan with wood laminate floors and ceramic tile in baths. This unit has walk-in closets in both the main bedroom and second bedroom. Open high vaulted ceilings. Very clean condo. Nice screened in porch area with insulated roof. Professionally cleaned top to bottom for new owners. Community has swimming pool. Convenient location to all the shops, restaurants, Full Sail and UCF. Located in a good school district. Property did not have Homestead exemption so with homestead taxes should go down.

Welcome to this enchanting one-story townhome, a rare gem in today's market. Nestled in the coveted Winter Park community of Windward Square, this spacious, open-concept home is perfect for both relaxation and entertaining. A wrought iron gate leads you into the large front courtyard, offering a secluded yet inviting entrance. Inside, abundant natural light floods the home through custom plantation shutters windows, creating a warm and inviting atmosphere. The thoughtfully designed living space with 5inch custom baseboards features ample storage and counter space, making the kitchen ideal for entertaining. Stainless steel appliances, granite countertops, and a stainless steel backsplash add a touch of modern elegance. Both bedrooms open onto a private back courtyard, offering endless possibilities for creating your own outdoor oasis. Additional features include a recently replaced roof 2023 and electrical panel 2023, an inside laundry room, and a utility closet on the covered and screened patio perfect for additional storage. Enjoy the community amenities, including a large pool, clubhouse, tennis court, and playground. Located just moments away from top-rated schools, universities, popular dining, shopping, and transportation options, this townhome offers the perfect combination of comfort, style, and convenience. Don't miss the opportunity to make this delightful home yours!

One or more photo(s) has been virtually staged. I’m excited to share an incredible opportunity that you won’t want to miss—a spacious 3-bedroom, 2-bath condo in Winter Park at a fantastic price. Imagine closing on your new home before the Holidays!

This rare find comes with all appliances included, even the washer and dryer, making your move-in seamless. The community is packed with amenities, featuring three pools, tennis courts, laundry rooms, and a pet-friendly environment. Plus, the clubhouse has just been remodeled to include a brand-new fitness room for your convenience.

Four Seasons was designed with you in mind—blending traditional charm with a warm community feel that truly feels like home. Inside the condo, you’ll be impressed by the large rooms and thoughtful details such as remodeled Bathrooms, new windows and sliding door wall, an abundance of closets and even a outdoor storage closet. This quiet first-floor unit boasts great views and a spacious floor plan that invites comfort.

Located within the city limits of Winter Park often referred to as its best-kept secret—you’re just minutes away from downtown Orlando’s vibrant parks, entertainment options, fine dining experiences, and top-notch shopping. Educational institutions like Rollins College, Full Sail University, and UCF are also nearby.

Enjoy casual conversations with neighbors by the pool or simply relax in the serene environment of beautiful Winter Park. With a low HOA fee of only $430 covering water, trash removal, sewer services, pest control, building insurance and more—this is an opportunity you can’t afford to overlook.

Winter Park schools are highly regarded too: Brookshire Elementary School / Glenridge Middle School / Winter Park High School.

Let’s make your dream of owning this wonderful condo come true!

This spacious 2-bedroom, 2-bathroom condo in Cedarwood Village combines versatility and cozy comfort. The open floor plan is enhanced by soaring high ceilings and abundant natural light, creating a spacious and airy atmosphere throughout. Skylights brighten the living areas, making the space feel even more inviting. The kitchen features a separate bar and plenty of storage, seamlessly flowing into the dining and living areas—ideal for entertaining. A second-story loft offers a versatile space for a home office or hobby area. The fully enclosed back porch provides a private, year-round retreat. Additional features include ample storage, updated flooring, and a serene master suite. Perfectly situated in a peaceful community, this condo is the epitome of comfort and functional living. PLEASE NOTE this home is being sold as-is.

One or more photo(s) has been virtually staged. HERE IT IS!! First floor! End unit! 3 Bedrooms/2 Baths! Assigned Covered parking steps away from your new home! Inside Laundry! Adorable home with Luxury Vinyl Plank in living areas & carpet in bedrooms. Crown molding. New stainless steel appliances 2022. Charming screened patio and storage closet. This delightful community offers mature trees, 3 pools, tennis, shuffleboard, clubhouse, fitness center & ON SITE MANAGER! FOUR SEASONS is a serene, centrally located community in Winter Park near Full Sail, Cady Way Trail, Showalter Field, Ward Park, Winter Park Hospital, Wellness Center & YMCA and just a short drive to all the shoppes & restaurants on Park Avenue. WELCOME HOME!

This charming two-story, 2-bedroom, 2.5-bath condo in the highly desirable Winter Park area offers convenience, privacy, and prime location! Featuring an attached covered carport for parking convenience, this home is perfect for those looking for low-maintenance living with modern amenities. The primary bedroom, located on the second floor, includes its own private balcony—an ideal spot for morning coffee or relaxing in the evenings. The condo boasts a fenced-in backyard for added privacy and is set within a community that includes access to a clubhouse and a sparkling pool, perfect for unwinding or entertaining guests. Located just over 5 miles from Winter Park’s renowned Park Ave, you’ll have the area’s best-rated dining spots and boutique shopping at your fingertips. With easy access to SR-417, 408, and SR-50, as well as Full Sail University, you’ve got quick access to just about anywhere you need to go making this an unbeatable location. This home combines convenience, comfort, and a fantastic Winter Park lifestyle. Don’t miss out on this opportunity!

2/2 Condo

One or more photo(s) has been virtually staged. Remodeled 2nd story, end unit, 2-bedroom, 2-bath condo in stunning Winter Park! Enjoy all the charm Winter Park has to offer, just minutes from Park Avenue's shops and restaurants, or take a short bike ride to nearby parks and outdoor venues. This desirable end-unit condo has been upgraded with new kitchen cabinets, granite countertops, and stainless steel appliances. Recent 2023 improvements include a new AC, roof & gutters. The interior has been freshly painted, and the home boasts new outlets, wall switches, and light fixtures throughout. Enjoy new luxury vinyl floors and plush carpeting, as well as all-new door hardware for a polished look. The community offers a pool and an on-site laundry facility. With Mead Gardens right behind the complex, you’ll have access to some of the best walking paths in Winter Park. Conveniently located between Trader Joe's, Winter Park Village, Ivanhoe Row, and Mills restaurants, and just a short distance to Park Avenue, Winter Park Tennis Center, Seven Oaks Park, and Rollins College. With low monthly fees, this is a fantastic opportunity to live affordably in Winter Park!