Winter Park Homes for Sale

Latest Winter Park Homes and Condos for Sale

Must see this beautiful 4 bedroom 3.5 bath 3,606 sqft home on one of the most charming streets in Winter Park nestled between Lk Knowles and Lk Wilbar. This home was exte...

4 Beds
3 Baths
Lake Knowles Terrace SubDv.
32789 Zip Code

1690 Dale Avenue, Winter Park $449,000

Location Location Location. RECENTLY RENOVATED. Updated kitchen cabinets, with stainless steel appliances, updated bathrooms with custom tile work, updated lighting fixtu...

4 Beds
2 Baths
Comstock Park SubDv.
32789 Zip Code

1211 Preserve Point Drive, Winter Park image

1211 Preserve Point Drive, Winter Park $2,415,000

Tuscan inspired custom built pool home located in Windsong offers five or six bedrooms, an open floor plan, home office, media and game room, and a stunning wrap-around s...

6 Beds
5 Baths
Windsong Lookout Landing 43/79 SubDv.
32789 Zip Code

1136 S Pennsylvania Avenue, Winter Park image

1136 S Pennsylvania Avenue, Winter Park — Na $799,000

Stunning Winter Park Georgetown townhome within walking distance to Park Avenue, shops, restaurants, and Rollins College. Urban living at its finest in Virginia Heights- ...

3 Beds
3 Baths
Virginia Heights Rep SubDv.
32789 Zip Code

720 W Webster Avenue, Winter Park $319,000

Location! Location! Location! This adorable three bedroom/2 bathroom + large office, single-story home, is just steps to upscale Park Avenue shopping and dining, Winter P...

3 Beds
2 Baths
Carver Town SubDv.
32789 Zip Code

609 Gallery Drive Unit B205, Winter Park image

609 Gallery Drive Unit B205, Winter Park — 609 $199,000

Tucked away in the heart of Winter Park lies this incredible condo. An end unit in the quiet community of THE GALLERY at Winter Park. This 2 bedroom, 2 bath home features...

2 Beds
2 Baths
Gallery At Winter Park Sec 01 SubDv.
32792 Zip Code

2938 Banchory Road, Winter Park $376,500

Welcome to your new home in Winter Park Pines. This 4 bedroom 2 bath pool home has 2257 sf of living area. The home has a split bedroom plan and a “pool planned bathro...

4 Beds
2 Baths
Winter Park Pines SubDv.
32792 Zip Code

1671 Chestnut Avenue, Winter Park $1,019,000

Located in the highly coveted tree streets of Winter Park, this traditional two-story home features 5 bedrooms, 3.5 bathrooms, and plenty of entertaining space inside and...

5 Beds
3 Baths
Lake Knowles Terrace SubDv.
32789 Zip Code

567 Osceola Avenue, Winter Park $932,000

Award Winning, Winter Park Historic 4 Bed, 3-1/2 Bath Home meticulously restored to Perfection. With Features and Finishes that rival new homes in the area, it will not ...

4 Beds
3 Baths
Osceola Court SubDv.
32789 Zip Code

672 Osceola Avenue Unit 672, Winter Park image

672 Osceola Avenue Unit 672, Winter Park — B $449,000

Just a few blocks from Park Avenue and Rollins College sits a small cluster of luxury condominiums on a piece of property that is part of a larger piece on Lake Virginia....

2 Beds
2 Baths
Villa Del Seis Condo SubDv.
32789 Zip Code

2825 Roxbury Road, Winter Park $269,000

Move in ready! Open floor plan beauty with flex living space. Three bedrooms, one and a half baths. Fantastic 26' x 9' additional living space can be a play area, guest r...

2 Beds
1 Baths
Fairbanks Shores 2nd Add SubDv.
32789 Zip Code

1637 Magnolia Avenue, Winter Park $1,489,000

Welcome to the home of your dreams!! Your brand new 2020 Custom built French Provincial style estate is ready and waiting for your family. The quality craftsmanship and p...

4 Beds
4 Baths
Flora Park 2nd Add SubDv.
32789 Zip Code

1228 Mayfield Avenue, Winter Park $1,740,000

This spectacular Spanish Colonial style home is situated on an oversized lot on a quiet brick street in one of Winter Park’s most sought after neighborhoods. Painstaking...

4 Beds
3 Baths
Temple Heights SubDv.
32789 Zip Code

1061 Cherokee Avenue, Winter Park $299,900

Hidden gem in the heart of Winter Park! Updated 3/2 block home in a prime location! Zoned for a highly rated Winter Park High School, this home is located within a walkin...

3 Beds
2 Baths
32789 Zip Code

331 Cortland Ave, Winter Park $449,000

Welcome Home to this charming single story 2 bedroom 2 bath home located in desirable Winter Park. Built in 1946, this home exudes charm, boasting original bathrooms and...

2 Beds
2 Baths
Osceola Summit SubDv.
32789 Zip Code

1891 Oglesby Avenue, Winter Park $389,900

Do not miss your opportunity to call this lovely 3 bedroom, 2 bathroom property in Winter Park your NEWLY BUILT HOME!!! The building was brought down to the block and reb...

3 Beds
2 Baths
Olympia Heights SubDv.
32789 Zip Code

2041 Lake Drive, Winter Park $639,000

DESIREABLE LAKE KILLARNEY CLASSIC HOME WITH MODERN UPDATES JUST BEGINS TO DESCRIBE THIS 4 BEDROOM 4 BATH POOL HOME SEATED ON A CORNER LOT IN THE VERY PRIVATE NEIGHBORHOOD...

4 Beds
4 Baths
Lake Killarney Homeowners' Association, Inc. SubDv.
32789 Zip Code

151 N Orlando Avenue Unit 240, Winter Park image

151 N Orlando Avenue Unit 240, Winter Park — 151 $190,000 ▼

Beautiful 2 bedroom 1 bath condo in a cool 2 story mid-century building on Lake Killarny next to Trader Joes. It is totally renovated with granite counter tops, stainless...

2 Beds
1 Baths
Lake Killarney Condo SubDv.
32789 Zip Code

1750 Edwin Boulevard, Winter Park $1,425,000

Discover an exceptional opportunity in the heart of Winter Park. This beautiful custom-built two-story modern home is very bright with southern exposure on the rear of th...

5 Beds
4 Baths
Campo Bello SubDv.
32789 Zip Code

2265 Lee Road Unit 101B, Winter Park image

2265 Lee Road Unit 101B, Winter Park $209,000

Ground floor office condo located on the SW corner of the atrium style office building. Move in ready unit consist of 4 private offices, conference room, waiting room, re...

Zom Lee Office Center 01 Condo SubDv.
32789 Zip Code

820 N Lakemont Avenue, Winter Park image

820 N Lakemont Avenue, Winter Park $790,000

An exceptional opportunity awaits in the heart of Winter Park. This transitional-style custom home is comprised of four bedrooms and three baths over 3,113 square feet of...

4 Beds
3 Baths
Acreage SubDv.
32792 Zip Code

55 Trismen Terrace, Winter Park $6,595,000

Presenting to the market for the first time in 54 years and the first time ever as three properties combined over the years all within footsteps of Park Avenue and situat...

4 Beds
6 Baths
Osceola Shores Sec 01 SubDv.
32789 Zip Code

1641 Winchester Drive, Winter Park image

1641 Winchester Drive, Winter Park $809,000

Absolutely lovely 3-bedroom, 2.5-bath renovated home in highly desirable Timberlane Shores. Split level floor plan with walk out basement to patio and large private fully...

3 Beds
2 Baths
Timberlane Shores SubDv.
32789 Zip Code

2837 Scarlet Road, Winter Park $379,900

Opportunity knocks - ACT FAST!!! This beautiful fully remodeled 3 bedroom, 2 bath home is not going to last! Wood plank tile flooring throughout with rugs in the bedrooms...

3 Beds
2 Baths
Winter Park Pines SubDv.
32792 Zip Code

467 Carolina Avenue, Winter Park $1,195,000

Brand new home. 10 foot ceilings. Front and back porches. Engineered wood floors. Thermidor appliances. Upgraded windows. Huge attic storage. Surrounded by 6 foot block w...