Winter Park
Upscale, modern, and with too many gorgeous homes for sale, Winter Park is a stunning city with lots to offer just minutes from Orlando making it ideal for any family or investor looking for the delights of suburbia with upscale living. Park Ave. or downtown is a beautiful historic area lined with gourmet restaurants, art galleries, wine bars, and a plethora of shopping options.
Fine institutions like Rollins College, the Albin Polasek Museum and Sculpture Garden, and theaters like The Winter Park Playhouse and Enzian provide plenty of excellent entertainment options. The area has a home for every type of buyer whether an investor, flipper, family, or individual.
Located along the I-4 corridor, the town is conveniently located. Although a quiet area but with only a brief drive you have the bright lights and bars of Downtown Orlando. Winter Park is growing and property values are going one way, up. Come explore this fantastic city today.
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Homes for Sale in Winter Park
2827 PARKLAND CIRCLE
WINTER PARK, Florida 32789
Albin Hubscher
4Bedroom(s)
3Bathroom(s)
61Picture(s)
3,714Sqft
Welcome home to this professionally decorated two-story custom French provincial pool home. No space or detail has been overlooked, and with an endless list of upgrades, this home is sure to impress the pickiest of buyers. Located at the end of Parkland Circle cul-de-sac, this home exudes charm and has modern day features to make daily living that much easier.
$1,995,000
1714 WESTCHESTER AVENUE
WINTER PARK, Florida 32789
JJ Mackle
3Bedroom(s)
2Bathroom(s)
30Picture(s)
2,114Sqft
Welcome to Orwin Manor, a timeless Orlando-Winter Park neighborhood established in 1924, offering lifestyle and prime location. Come see this designer dream! Solidly built one-story pool home with three bedrooms, two baths, one half bath (by pool), 2,114 square feet, one-car garage and wood flooring throughout. Situated on a well-manicured 0.
$799,000
1651 MAYFIELD AVENUE
WINTER PARK, Florida 32789
MaryStuart Day
4Bedroom(s)
4Bathroom(s)
42Picture(s)
3,238Sqft
This stunning home, built by LunDev Custom Homes, boasts clean, modern features and an exceptionally designed floorplan, while only steps from Phelps Park, tennis courts, and the YMCA. Since it was completed in 2020, additional upgrades totaling over $100K have transformed this home, providing an extraordinary lifestyle.
$1,950,000
311 MORSE BOULEVARD
WINTER PARK, Florida 32789
Maria Van Warner
2Bedroom(s)
2Bathroom(s)
30Picture(s)
1,682Sqft
Don't miss out on this updated 2 bedroom, 2 bath condominium in the exceptional 55 and over Whispering Waters community located on the Winter Park Chain of lakes. This second floor, 1,682 sq. ft. home features lots of natural lighting with double sliders in the living room providing great views of Lake Osceola.
$640,000
3340 BALSAM DR
WINTER PARK, Florida 32792
Joseph Pacholski
3Bedroom(s)
2Bathroom(s)
54Picture(s)
1,424Sqft
JACKPOT! NEW ROOF AND GUTTERS 2023! HVAC 2021!, Interior completely painted including garage floor 2023! $61,000 in improvements on this home since 2017. Move in ready! This home boasts beautiful low maintenance chiseled travertine in living area and one bedroom and new Carpet in master and extra Bedrooms.
$412,000
202 LONGBRANCH COURT
WINTER PARK, Florida 32792
Alicia Spears
4Bedroom(s)
3Bathroom(s)
64Picture(s)
2,855Sqft
This one of a kind Winter Park 4 bed/3.5 Pool contemporary two-story ranch estate is sure to impress! Sitting on nearly an acre in a secluded cul de sac makes this property a private oasis with endless possibilities.
$850,000
1918 SUMMERFIELD ROAD
WINTER PARK, Florida 32792
Sonia Dublis
5Bedroom(s)
4Bathroom(s)
55Picture(s)
3,269Sqft
BETTER THAN NEW AND READY FOR YOU! BUILT IN 2021!! Designed and built by Winter Park architect and building contractor, Stevens, Inc., this CUSTOM CRAFTSMAN style home brings so much character from the wood and tile floors to the beautiful tongue and groove clear pine ceilings.
$1,300,000
1554 HARRIS CIRCLE
WINTER PARK, Florida 32789
Jennifer Sloan
3Bedroom(s)
2Bathroom(s)
40Picture(s)
2,801Sqft
Pre-inspected. Offered for the first time in over 30 years! Winter Parkâs only original, charming and completely remodeled historical farmhouse. Known as the âHarris-Edison Houseâ, original construction dates back to 1887 as one of the largest and oldest Winter estates.
$1,220,000
150 LEWFIELD CIRCLE
WINTER PARK, Florida 32792
Liza Figueroa
1Bedroom(s)
1Bathroom(s)
30Picture(s)
678Sqft
Located in the Stratford, a well-maintained community in Winter Park between Maitland and Casselberry. The two story brick buildings give it a clean and bright look. The unit is located on the second floor and its open floorplan is a must see. This unit has a spacious bedroom and a bathroom, with a tub/shower combination. There is a stackable washer/dryer in a closet.
$165,000
1740 VIA PALERMO
WINTER PARK, Florida 32789
Mick Night
5Bedroom(s)
5Bathroom(s)
43Picture(s)
5,259Sqft
Nestled near the heart of Winter Park, this modern masterpiece exudes elegance and superb attention to detail throughout. This home was a Parade of Homes collaboration between IBK Construction & Z Properties, Inc. The entrance sequence is a showstopper including a private auto gated drive, motor court and a beautiful floating entryway with dissecting double water features on both sides.
$4,200,000
656 RANDY LANE
WINTER PARK, Florida 32789
Warren Bonett
3Bedroom(s)
2Bathroom(s)
54Picture(s)
2,060Sqft
Located on a quiet, tree lined street in Timberlane, a neighborhood in Winter Park that is known for its beautiful homes and excellent proximity to great schools, amazing shopping, dining and so much more, this Mid-Century Modern home has been beautifully updated and ready for the next chapter in a new owner(s) life.
$795,000
1270 GLADIOLAS DRIVE
WINTER PARK, Florida 32792
Thomas Noelke
3Bedroom(s)
2Bathroom(s)
66Picture(s)
1,644Sqft
Located in the picturesque Winter Park area of Florida, this stunning home boasts an UNPARALLED LAKEVIEW and is surrounded by lush tropical forest landscaping, providing a sense of privacy and tranquility.rnAs you step inside, you'll be greeted by an open floor plan that allows for seamless flow between the living, dining, and kitchen areas.
$530,000
