Central Florida Real Estate Search

Winter Park Homes for Sale

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Winter Park

About Winter Park, Florida

Winter Park is a city unlike any other in Central Florida. Between the upscale shopping and dining experiences, festivals, and old-world charm, it's easy to see why Winter Park calls itself the "city of arts and culture." Winter Park is home to Rollins College, the first recognized college in the State of Florida. Every Saturday, downtown Winter Park hosts a farmer's market where visitors can pick up fresh produce, coffee beans, or an early morning treat. If you need a break from shopping, take a stroll through the 47-acres of Mead Botanical Garden where visitors are invited to explore the grounds for free.

Our website features the best Winter Park real estate search for homes, condos, land and foreclosure properties available. It is the only site you will ever need! It is easy-to-use and updated by the official REALTOR®’s database every 15 minutes. 

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Newest Winter Park Homes for Sale

$3,295,000
4 Beds 3.5 Baths Killarney Point SubDv. 32789 Zip Code
Lakefront luxury on the beautiful shores of Lake Killarney! Custom built with attention paid to every detail, this Mediterranean oasis delivers 4 spacious bedrooms, 3 full and 1 half baths, a library, theater room, climate controlled wine room, infinity edge pool and sweeping water views! 100’ of private lake frontage, 4 fireplaces, fiber optic lighting and a full Summer kitchen make this home an entertainer’s paradise. Step inside the grand front entry doors and be greeted by a panoramic view of Lake Killarney through the floor to ceiling windows. The custom 20’ stone fireplace is a striking feature of this open floor plan in addition to the travertine tile floors, and elegant floating staircase. Follow the natural flow into a chef’s dream kitchen featuring a hidden sub-zero refrigerator, Wolf gas range in the cooking island with granite counters throughout, and a comfortable casual breakfast nook with French door access outside and tons of natural light. The 3-sided stacked stone fireplace adds ambiance to the kitchen as well as a gorgeous custom-built library, and the beautiful living area, where 2-story windows complete with remote-controlled window treatments overlook Lake Killarney. The main floor features the 3 guest bedrooms, one with an en-suite bathroom. The staircase is a work of art and brings you to your personal retreat in the Owner’s suite, which features stunning lake views, a dual sided fireplace, sitting area, mini bar, oversized walk-in closet and a large private balcony! The en-suite bath features an expansive dual sink vanity for space and storage, jetted tub with lake views and a huge shower with dual shower heads and seamless glass doors. Also on the second floor is a bonus room which would make a great nursery, home office or gym, as well as a fully equipped and furnished media room. The backyard of this home is thoughtfully designed and one of a kind for the family that likes to entertain, offering a well equipped Summer kitchen with bar seating, fireplace, and a heated infinity pool with a zero edge spillover spa, colored lighting, and fire bowls. Bring your boat - the covered dock features a lift with electrical and a deck for watching the sunset over the lake! Call today and schedule your private tour of this lakefront sanctuary!

2138 Lake Drive, Winter Park

$1,895,000
4 Beds 4 Baths Fontainebleau SubDv. 32789 Zip Code
An elegant custom home, designed & built by FG Shaub, is tucked away on a large corner lot on a pristine oak-lined street, offering incredible privacy. This home offers transitional design and modern function with a perfect neutral palette as a backdrop to easily blend with your own design. A welcoming foyer invites you into this 4-bedroom 4 full bath 3-way split plan features a downstairs master as well as additional main floor guest or mother-in-law suite with dedicated bath and 2 ensuite bedrooms upstairs and a massive bonus space, which a section of it could be converted to a 5th bedroom. Thoughtful design with entertaining at the forefront, with an open kitchen family, dining, gathering plan with banks of doors across the back that spill out onto the outdoor covered porch with views to the outdoor gas firepit. This dream kitchen is spacious with 42” custom wood cabinetry featuring undermount lighting and an expansive island with seating and a lighted display cabinet adding to its character. Granite counters with lots of workspace, closet pantry, stainless appliances that include an induction cooktop, which all add to ease in the kitchen. The back of the house “drop zone” and workspace is adjacent to oversized laundry room with great storage to keep everything organized. The main gathering space boasts volume ceilings, a dedicated bar/buffet or coffee/morning station which showcases glass cabinetry for display, undermount lighting a beverage refrigerator and spacious counter to serve from. The owner’s retreat is private with tray ceilings, a spacious fully customized walk-in closet, large shower and bath, His and Her vanities and floor to ceiling custom storage cabinets. The upstairs game or bonus room is a great multi-function space to meet your needs. The outdoor lifestyle abounds and is captured with a covered porch with a wood tongue and groove ceiling & phantom screens, recessed lighting & fans, neutral pavers which blend into the screened patio with an outdoor firepit to enjoy cool breezes under the stars. Other features include; wood floors & volume ceilings on both floors, tall base boards & crown molding, plantation shutters, LED recessed lighting throughout, lighted stairs, solid doors, upgraded hardware, whole house water filter & water softener, Security cameras, main living and outdoor speaker system, mature landscaping, pest guard system, thoughtful storage throughout and additional upstairs dedicated walk in storage room. This home is meticulous with so many details considered. Fantastic schools zoned for Dommerich, Maitland and Winter Park High and close to everything Winter Park Offers. This is a special street and one you will love.

1531 Place Picardy, Winter Park

$1,625,000
4 Beds 4.5 Baths Tuscany Island SubDv. 32792 Zip Code
Enjoy the Winter Park lifestyle in this fabulous 4 bedroom, 4.5 bath home, built in 2006 with a clean and well-planned 4625 sqft floorplan. This beautiful Mediterranean style home is nestled among 4 other estate homes in the private cul-de-sac gated community of Tuscany Island. Approach the home with a circular paver driveway that has a beautiful double door entry surrounded by well manicured mature landscaping. The front entryway opens into the formal living room with a gas fireplace with a beautiful view of the pool through the plantation covered windows. To the right, you will find the formal dining room with a coffered double tiered ceiling. To the left of the main entrance is the private office with built in shelves. The private owners' suite has views and entry to the pool area. Enjoy a nice soothing bath in the jetted tub. The large walk-in closet has custom built-ins. Enter into the bright and airy kitchen with light cabinetry and solid surface countertops. Here you will find gas range cooking with a stainless steel hood and upgraded stainless steel appliances. The kitchen opens up into the large great room with voluminous ceilings. Enjoy meals together in the breakfast nook overlooking the pool. Beyond the family room is a newly remodeled custom library with soaring ceilings where you can enjoy many hours of reading or immersing yourself in crafts or concentrate on work from home. You’ll find two bedrooms at the front part of the right wing of the home that share a bathroom. The fouth bedroom in the rear of the home with its' own pool bathroom. This will be a great space for guests to come stay. The flooring was recently updated to remove all carpet from the home. The second floor boasts a bonus room that can be used as a guest suite that has its’ own private bathroom or it can be used as a media room. There is a laundry room equipped with cabinetry for storage and a wash basin. The three car garage is side entry. The outdoor back yard has a beautiful entertaining area equipped with an outdoor kitchen as well as a sitting area with an outdoor fireplace where you can enjoy beautiful nights eating dinner with family and friends. Your guests can take a dip in the refreshing serene pool. This home is conveniently located near major highways and with retail shopping and a variety of eateries and groceries close by. Schedule your private showing today!

4464 Tuscany Island Court, Winter Park

$330,000
3 Beds 2 Baths Howell Branch Woods SubDv. 32792 Zip Code
The golden rule in real estate. Location! Location! Location! A three bedroom, two bath Pool home in Winter Park for under $350,000? Yes, and it is PRICED TO SELL. This gem needs some polish to shine to it's full potential, but with the right touches this home could yield over $400,000 due to the location! It is a prime candidate for a renovation loan if someone would like to take the time to really customize and create their own masterpiece. The pool is original with the house, and they don’t make them like this anymore, extra deep and crystal clear. There is even an outdoor shower plumbed by the pool. There are two sets of sliding doors that lead to a screened patio. There is a living room and dining room in the front of the home, and an additional family room off the kitchen that can be used as an office space, play room, craft room and so much more. The electrical panel has recently been changed out. The home has lots of closet space with a coat closet in the foyer, a pantry closet in the kitchen and a long hall linen closet. There are no known structural issues so the home has good "bones" as they say. The neighborhood is in such a prime location and raved about by the neighbors! You can stand at the end of the driveway and see Eastbrook Elementary down the street. The closest intersection is Tangerine and Howell Branch Road or you can jump on Tangerine Road from Aloma Avenue. The middle school bus stop is in front of this home! There is no HOA but the neighbors keep their homes so tidy and nice. This one will go fast so do not hesitate to make an appointment today!

7001 Jackman Boulevard, Winter Park

$620,000
4 Beds 3.5 Baths Winter Park Pines Rep SubDv. 32792 Zip Code
Stunning 4 Bedroom 3.5 Bathroom Home with two Master Suites in sought after Winter Park is ready for a new owner! From the moment you enter into the foyer, you will be impressed with the beautiful Open Floor Plan with Spacious kitchen, boasting Stainless Steel Appliances, Granite Island with bar seating, Quartz Countertops, and Marble Backsplash not to mention the modern cabinetry. Enjoy the private view from the large glass sliding doors going out to the Large Screened in Lanai. Perfect for Entertaining all of your guests, The formal dining room is open to the kitchen. You will love the wide plank tile flooring in all the living spaces. There is half bath right off of the great room. Speaking of the Great Room it is just a step down from the kitchen with sliding glass doors going out to a Fenced in Private Backyard. The first Master Suite has the wood look wide plank ,a huge closet, including custom shelving and an impressive bathroom with large tile, Granite Counter top and designer features. Down the hall, you will find the second bedroom across from bath 2 with Granite countertop, beautiful tile and a tub and shower combo. On to the Second master suite featuring Wood Flooring, and a large open shower in the bathroom. A fourth bedroom also has wood flooring and a large closet. This Impressive home has been completely remodeled. It has a newer roof 2019 and a two car garage with open and freshly painted floor. All of this and much more so close to downtown Winter Park with all of its shopping, restaurants, and art festivals, UCF, the expressways, and Full Sail University. Hurry!

2817 Prince John Road, Winter Park

$128,000
2 Beds 2 Baths Winter Park Woods Condo SubDv. 32792 Zip Code
Resting in quiet Winter Park this can become a home for you and your family or an income-producing condo which is ready for you to add to your network! Close to local colleges and just a short bike ride away from Full Sail University, this two bed two bath unit is perfect for college renters and young families getting established in the area. The community also offers a full suite of amenities with kid's park, pool, and sporting areas. As you step inside you first encounter the kitchen to the right with a decent amount of storage space and a full set of appliances. Next, the floorplan opens up into a spacious living and dining area perfect for relaxing after a long day at work and school! From here the property is arranged in a split floor plan with the first bedroom and bath to the front of the home and the master suite to the rear. The way it's set up is perfect for either a kid's room and guest bath or roommate situation as the guest bath is situated right next to the first bedroom in a way a curtain could be put up to make a pseudo second master. Stepping through the sliding glass doors you'll find a generously sized screened patio with a laundry closet that fits a stacked unit with space to spare for storage. To take a look at this property and learn more about it's income opportunities call today for more information or to schedule a private showing!

243 Scottsdale Square Unit 243, Winter Park

$599,999
3 Beds 2 Baths Kenilworth Shores Sec 07 SubDv. 32792 Zip Code
One or more photo(s) has been virtually staged. One or more photos are virtually staged. Beautifully renovated! This Winter Park family house is located on a quiet, private dead-end street and has been completely re-designed on the inside for the total entertainment of family and friends. From the moment you walk in, large ceramic tile floors throughout, updated flooring in the bedrooms and hallway. The bedrooms are joined by a slate tile bathroom with new shower features. We said entertaining, because the kitchen is like no other. Surrounded by custom made solid wood cabinets, along with all new stainless steel appliances, including double stacked convection/microwave and standard oven, Gas burning stove, stainless steel hood, all surrounded by 2 1/2 bullnose granite countertops accented with Mexican tile backsplash and double tiered bar. Under mounted stainless steel double deep sinks, garbage disposal and dishwasher. All new professional lighting throughout the house. New plumbing, insulation, walls, ceilings, complete air condition overhaul with 4-ton air conditioning unit, water heater, most windows: new double panel. Vacuum sealed double panel rear window tinted for further heat protection. Step outside through French doors to a beautiful paved entertainment tropical backyard landscaping and sprinkler system. Private lake access to enjoy. This Home is close to Baldwin Park, Ward Park, Blue Jacket Park, Cady Way Pool & Lake Berry.

2008 Natalen Road, Winter Park

$406,590
3 Beds 2.5 Baths Grayson Square SubDv. 32792 Zip Code
Under Construction. At Pulte, we build our homes with you in mind. Every inch was thoughtfully designed to best meet your family’s needs, making your life better, happier and easier. This gorgeous move-in ready Springdale II two-story townhome offers 3 bedrooms, 2 full bathrooms, a first-floor powder room, a single-car garage, covered back lanai, window blinds, washer, dryer and a refrigerator. The spacious first floor is ideal for entertaining, featuring an open concept gathering room, café and modern kitchen, powder room and a covered lanai with double sliding glass doors. Upstairs, the Owner's Suite features a spacious walk-in closet and en suite bathroom with a dual sink Blanco Maple quartz-topped double vanity, private water closet and oversized shower. Two additional bedrooms, the second full bathroom and the laundry closet are on the opposite side of the second floor, offering privacy and space for everyone. Professionally curated design selections include Smart Home package, White Ellis Cabinets, Blanco Maple quartz countertops, Boston Perla Ceramic tile flooring throughout the first floor living areas and bathrooms, and stain-resistant Arrendale Turk Ornamental Gate carpet in the bedrooms. This best-selling Springdale II design will not last so visit today! This is the perfect townhome for first-time buyers or investors and offers a transferable home warranty. Grayson Square is an intimate gated luxury townhome community located minutes away from downtown Winter Park, right off Howell Branch Road! This low-maintenance neighborhood will feature gated access, private homesites with pond views and no rear neighbors, a resort-style pool with cabana and 1GB high-speed fiber optic internet, along with 75 streaming cable and music channels – all with no CDD. Boasting an unbeatable location in coveted Winter Park, just one mile to 436, 434, and less than 3 miles from 417, your new home at Grayson Square offers all your daily conveniences, such as Starbucks and Publix, just minutes away! Plus, you’ll have access to quality Seminole County Schools. And when it’s time to change pace, you’ll love your proximity to the famous shopping and dining of Park Avenue.

2029 Canny Cove, Winter Park