Find a Home

Browse by City for Properties for Sale or Rent

Search over 4.5 Million Real Estate Listings

Ex. "City, State" or "ZIP Code"

Buy ^* Rent
*New: Incl. Foreclosures

Click for More Search Options »

Get free Florida Car Insurance Quotes

Winter Park Homes For Sale

Listings View: Detailed | Photos | Text

1,616 Listings Found (Narrow Search to View all Properties)

Search Results Page 1 of 99

Listings Sort: Highest Prices | Lowest Prices | Newer Listings | Older Listings | Location

For sale listings in winter park,fl, single family homes (Modify Search)

Home For Sale in WINTER PARK, FL

1220 N PARK AVE, WINTER PARK, FL, 32789, USA

Map | View Listing

More Photos

$20,000,000
5 Bedrooms
5 Baths
11931 square ft.

CASA DEL MONDO - HOUSE OF THE WORLD. IMAGINE THE LOOK OF AN ITALIAN MEDITERRANEAN MANSION SET IN A HAWAIIAN RAIN FOREST ON THE SHORES OF A TAHITIAN LAGOON BUT INSTEAD ITS A 1.5 AC GATED ESTATE ON LAKE MAITLAND IN THE HEART OF WINTER PARK. 14931SF. ... MLS# O4989010 Detailed Listing

Property Type: single family

CASA DEL MONDO - HOUSE OF THE WORLD. IMAGINE THE LOOK OF AN ITALIAN MEDITERRANEA

1220 PARK, Winter Park, FL 32789

Map | View Listing

More Photos

$20,000,000
5 Bedrooms
6.5 Baths
11931 square ft.

Property Type: single family

Real Estate Listing Courtesy of: COLDWELL BANKER RESIDENTIAL RE

Home For Sale in WINTER PARK, FL

420 N INTERLACHEN AVE, WINTER PARK, FL, 32789, USA

Map | View Listing

More Photos

$6,995,000
5 Bedrooms
7 Baths
9399 square ft.

Welcome to the Premier home on the Winter Park chain of lakes. Constructed in 1938 in the Italianate style and updated in 1989, this home has the grace of the old combined with the functionality of the new. There are spaces for everyone in the ... MLS# O4949379 Detailed Listing

Property Type: single family

420 N Interlachen Ave, Winter Park

420 N Interlachen Ave, Winter Park, FL, 32789, United States

Map | View Listing

$6,995,000
5 Bedrooms
7 Baths
9399 square ft.

Property Type: single family

Real Estate Listing Courtesy of: Winter Park Land Co

Home For Sale in WINTER PARK, FL

240 TRISMEN TERR, WINTER PARK, FL, 32789, USA

Map | View Listing

More Photos

$6,600,000
7 Bedrooms
8 Baths
8000 square ft.

THIS LAKE FRONT ESTATE HOME IS LOCATED OFF THE BEAUTIFUL LAKE OSCEOLA AND WILL TRULY TAKE YOUR BREATH AWAY! TAKE YOUR BOAT FOR A SPIN OR SIMPLY ENJOY THE BEAUTY FROM YOUR MASTER BEDROOM WINDOW OR WIDOWS TOWER ON THE ROOF OF YOUR HOME. PLAY A GAME OF ... MLS# S4669799 Detailed Listing

Property Type: single family

"Four Winds", the site of James Gamble Rogers' 1929 home on the Isle of Sicily,

3 ISLE OF SICILY, Winter Park, FL 32789

Map | View Listing

More Photos

$5,500,000
4 Bedrooms
5 Baths
7531 square ft.

"Four Winds", the site of James Gamble Rogers' 1929 home on the Isle of Sicily, is available for purchase. This magnificent French Provencial Normandy style home underwent major renovation and additions in 1987 and 1993, and is situated on both the MLS# O4992176 Detailed Listing

Property Type: single family

Real Estate Listing Courtesy of: COLDWELL BANKER RESIDENTIAL RE

Home For Sale in WINTER PARK, FL

3 ISLE OF SICILY, WINTER PARK, FL, 32789, USA

Map | View Listing

More Photos

$5,500,000
4 Bedrooms
4 Baths
7531 square ft.

Four Winds, the site of James Gamble Rogers' 1929 home on the Isle of Sicily, is available for purchase. This magnificent French Provencial Normandy style home underwent major renovation and additions in 1987 and 1993, and is situated on both the ... MLS# O4992176 Detailed Listing

Property Type: single family

Home For Sale in WINTER PARK, FL

WINTER PARK, FL, 32789, USA

Map | View Listing

More Photos

$5,350,000
6 Bedrooms
7 Baths
8653 square ft.

Exquisite luxury yet warm and livable. This privately gated home is surrounded by water on 3 sides and located in the exclusive Estates section of Windsong.From the Brazilian Cherry floors to the Travertine pool deck,every detail has been hand ... MLS# O4978340 Detailed Listing

Property Type: single family

Winter Park

992 Genius Dr, Winter Park, FL, 32789

Map | View Listing

$5,350,000
6 Bedrooms
7 Baths

Privately gated luxury home in the exclusive 'estates' section of Windsong in historical Winter Park. Exquisite detail and pristine landscaping on this 1& acre wterfront homesite. MLS# O4978340 Detailed Listing

Property Type: Residential

Real Estate Listing Courtesy of: Keller Williams Heritage Realty

Home For Sale in WINTER PARK, FL

1250 N PARK AVE, WINTER PARK, FL, 32789, USA

Map | View Listing

More Photos

$5,300,000
5 Bedrooms
5 Baths
8207 square ft.

Exquisite lake front home situated on 157 ft on the shores of Lake Maitland in the heart of Olde Winter Park. Exclusive Winter Park chain of lakes. Amazing 1.5 acre lot is meticulously manicured. This gated estate custom built by Charles Clayton in ... MLS# O4954715 Detailed Listing

Property Type: single family