Winter Park FL Homes & Real Estate

Welcome to Winter Park, FL, a treasure trove of enriching experiences that promises an exceptional lifestyle. Embark on the Chain of Lakes Boat Tour, a delightful journey through serene waters that unveils the city's scenic natural beauty. Immerse yourself in the legacy of Rollins College, where the spirit of Mr. Rogers himself once graced the campus. Stroll down the charming brick streets, adorned with Spanish moss and centuries-old trees, creating an enchanting atmosphere. Elevate your family's future with an A-rated school system, ensuring a top-tier education. Embrace the historical charm of a New England-style downtown that keeps timeless traditions alive through holiday parades and High School Homecoming festivities. Delight in the luxury of Park Ave Shopping and Five Star Dining, offering a lifestyle that marries sophistication with comfort. Winter Park invites you to a life enriched by history, culture, education, and the finer things that make every day exceptional.

Included below are homes for sale and real estate in Winter Park, FL. If you would like more information on any of these Winter Park real estate listings, just click on a property to access the full details. From there, you can request more information or schedule a tour. And we'd be happy to provide you with disclosures, past sales history, dates and prices of properties which have recently sold nearby, and more, so just let us know how we can help!

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Winter Park September 22, 2023
172
Listed
69
Avg. DOM
$421.59
Avg. $ / Sq.Ft.
$674,950
Med. List Price
172 Properties
Page 1 of 15
$3,990,000
Neighborhood: Landmark Winter Park Condo
3
Beds
3
Baths
2,143
Sq.Ft.
2008
Year Built
1
Day on Site
O6143278
MLS
COVETED FRONT CORNER PENTHOUSE RESIDENCE NOW AVAILABLE! THE LANDMARK IS AN AWARD WINNING LUXURY CONDO BUILDING IN DOWNTOWN WINTER PARK. AN AMAZING LARGE PRIVATE BALCONY, UNIQUE ONLY TO THE PENTHOUSE...
Open 9/24
2100 Lake Dr Winter Park,  FL 32789
$2,275,000
Neighborhood: Killarney Point
4
Beds
3F11/2
Baths
3,555
Sq.Ft.
1958
Year Built
1
Day on Site
O6143813
MLS
Offered at $2,275,000 - 2100 Lake Drive, Winter Park. Enjoy panoramic lakefront views from the privacy of your own home with this remarkable single-story lakefront residence on Winter Park's private...
$502,790
Neighborhood: Grayson Square
3
Beds
2F11/2
Baths
1,782
Sq.Ft.
2023
Year Built
1
Day on Site
O6144035
MLS
Under Construction. At Pulte, we build our homes with you in mind. Every inch was thoughtfully designed to best meet your needs, making your life better, happier and easier. This gorgeous end unit...
Open 9/23
2464 Firstlight WAY Winter Park,  FL 32792
$479,500
Neighborhood: Enclave At Hawks Crest
3
Beds
2F11/2
Baths
2,308
Sq.Ft.
2020
Year Built
1
Day on Site
O6143947
MLS
Welcome to Winter Park's newest Luxury Resort Townhome Living in the Exclusive Gated Community of the Enclave at Hawk's Crest! This energy-efficient and smart automated 3 bedroom and 2 bath...
Open 9/23
1600 Barcelona Way Winter Park,  FL 32789
$1,600,000
Neighborhood: Sevilla
4
Beds
3F11/2
Baths
3,014
Sq.Ft.
1972
Year Built
1
Day on Site
O6144100
MLS
Located is the established Winter Park neighborhood of Sevilla, this updated 4 bedroom/3 bath, 3,014 sq ft single-story brick home sits on a beautiful .43-acre lot on a quiet cul-de sac. As you...
$215,000
Neighborhood: Parkview Village
2
Beds
2
Baths
1,018
Sq.Ft.
1984
Year Built
1
Day on Site
O6143886
MLS
Presenting an immaculate gem, this stunning 2-bedroom, 2-bathroom corner unit condo boasts an expansive and airy open floor plan on the coveted 2nd floor. Nestled in the highly sought-after Winter...
$499,900
Neighborhood: Albert Lee Ridge First Add
4
Beds
3
Baths
1,809
Sq.Ft.
1957
Year Built
1
Day on Site
O6144082
MLS
LOCATION LOCATION LOCATION! Two minutes to I-4 for easy commute. Gorgeous open concept recently renovated cozy and charming 4 bedroom/3 bath in sought after city of Winter Park. Upgraded modern...
$1,950,000
Neighborhood: Sorensen Heights
4
Beds
3F11/2
Baths
4,257
Sq.Ft.
2004
Year Built
1
Day on Site
O6116410
MLS
A stunning home in Winter Park ready for the next lucky family to move in! This charming four-bedroom, 3.5-bath home has it all. The moment you walk in the front door from the circular drive you will...
Open 9/23
1710 Winter Park Rd Winter Park,  FL 32789
$775,000
Neighborhood: Charmont
3
Beds
2
Baths
1,556
Sq.Ft.
1952
Year Built
2
Days on Site
O6142745
MLS
Move in ready 3 bedroom 2 bath Winter Park home located in the Audubon K-8 and Winter Park High district. This renovated and updated home has beautiful wood flooring, a lovely kitchen with a gas...
$495,000
Neighborhood: Wrenwood Heights Unit 2
5
Beds
3
Baths
2,250
Sq.Ft.
1975
Year Built
2
Days on Site
O6143482
MLS
Excellent primary residence with an income opportunity or two rental units in one! The main home is a spacious 3/2 with recently upgraded bathrooms and partial kitchen upgrade. A cool spiral...
Open 9/23
1405 Green Cove Rd Winter Park,  FL 32789
$2,995,000
Neighborhood: Camwood Sub
4
Beds
3F11/2
Baths
3,772
Sq.Ft.
2020
Year Built
2
Days on Site
O6142723
MLS
This exquisite residence features four spacious bedrooms, three and a half luxurious bathrooms, a convenient 2-car side-entry garage. Renovated from the ground up by Skolfield Homes in 2020, blending...
$850,000
Neighborhood: Lost Creek
5
Beds
3
Baths
2,954
Sq.Ft.
1996
Year Built
2
Days on Site
O6142674
MLS
Extremely rare opportunity to own a fully updated CONTEMPORARY MASTERPIECE in the heart of Seminole County, FL!! Meticulous maintenance and pride of ownership is obvious and gorgeous stylistic...