and narrow your search. If you have fewer than 200 results, you can save your search.

Winter Park Homes for Sale

Winter Park, FL is a family friendly, upscale suburban community. The city is located just seven miles northeast of Orlando. Park Avenue has a variety of upscale shops, restaurants, and art galleries. Winter Park Village offers outdoor shopping and restaurants. Popular nightlife attractions include Luma, Prato, Cocina 214, and Boca. Central Park has beautiful fountains, a rose garden, and seasonal events. Homes in Winter Park include condos, townhomes, and single family homes. The city is home to Rollins College, a private coed liberal arts school founded in 1885.

View Winter Park Properties

Explore all properties for sale in Winter Park, FL in the greater Orlando area listed below. As you search through listings please be sure to contact us with any questions or to schedule a viewing.

Search Smarter - Register on the site to save your favorite listings and to receive email notifications when similar listings come to market.

You may also be interested in Lake Mary.

1360 Alabama Dr, Winter Park, FL 32789

Price$7,500,000

Est. Mortgage: $/month

MLS Number O5541737

  • Single Family Residential
  • Area Winter Park
  • Address 1360 Alabama Dr
  • Square Feet 10,600
  • Year Built 2009

Listing Courtesy of KELLY PRICE & COMPANY LLC

{$agent->Name}

Fusilier Realty Group
9145 Narcoossee Road
Orlando FL, 32827
Office: 407-281-8455

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Nov 2, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

324 N Interlachen Avenue, Winter Park, FL 32789
Pending

MLS Number O5528771

  • Single Family Residential
  • Area Winter Park
  • Square Feet 8,738
  • Year Built 1925
  • Parking Spaces 2

Listing Courtesy of COLDWELL BANKER RESIDENTIAL RE

{$agent->Name}

Fusilier Realty Group
9145 Narcoossee Road
Orlando FL, 32827
Office: 407-281-8455

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Nov 2, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

570 Seminole Drive, Winter Park, FL 32789

Price$6,900,000

Est. Mortgage: $/month

MLS Number O5439246

  • Land
  • Subdivision Winter Park Old Town
  • High School Winter Park High
  • Junior High Maitland Middle
  • Acreage 2.25

This 2.25 acre lake front crown jewel is a once-in-a-lifetime offering of one of Old Winter Park’s most prestigious estate lots. Situated high above expansive Lake Osceola and only a short walk from famed Park Avenue, this lot, with its prevailing breezes, towering cypress trees and breathtaking lake view will inspire visions of the most elegant of estate homes. Located down a long oak lined private driveway, just off of quite brick paved Seminole Drive, this lot provides the ultimate in secluded privacy in the heart of Old Winter Park. There is simply nothing else like it.

Listing Courtesy of STOCKWORTH REALTY GROUP

{$agent->Name}

Fusilier Realty Group
9145 Narcoossee Road
Orlando FL, 32827
Office: 407-281-8455

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Nov 2, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

1016 Genius Drive, Winter Park, FL 32789

Price$6,795,000

Est. Mortgage: $/month

MLS Number O5496008

  • Single Family Residential
  • Area Winter Park
  • Address 1016 Genius Drive
  • Square Feet 10,314
  • Year Built 2005

Listing Courtesy of COLDWELL BANKER RESIDENTIAL RE

{$agent->Name}

Fusilier Realty Group
9145 Narcoossee Road
Orlando FL, 32827
Office: 407-281-8455

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Nov 2, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

115 Palmer Avenue, Winter Park, FL 32789

Price$5,750,000

Est. Mortgage: $/month

MLS Number O5547897

  • Single Family Residential
  • Area Winter Park
  • Address 115 Palmer Avenue
  • Square Feet 9,838
  • Year Built 1989

Listing Courtesy of REGAL R.E. PROFESSIONALS LLC

{$agent->Name}

Fusilier Realty Group
9145 Narcoossee Road
Orlando FL, 32827
Office: 407-281-8455

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Nov 2, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

1212 N Park Avenue, Winter Park, FL 32789

Price$4,950,000

Est. Mortgage: $/month

MLS Number O5544700

  • Single Family Residential
  • Area Winter Park
  • Address 1212 N Park Avenue
  • Square Feet 4,681
  • Year Built 1989

Listing Courtesy of FANNIE HILLMAN & ASSOCIATES

{$agent->Name}

Fusilier Realty Group
9145 Narcoossee Road
Orlando FL, 32827
Office: 407-281-8455

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Nov 2, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

1941 Legion Drive, Winter Park, FL 32789

Price$4,895,000

Est. Mortgage: $/month

MLS Number O5484879

  • Single Family Residential
  • Area Winter Park
  • Address 1941 Legion Drive
  • Square Feet 10,493
  • Year Built 2008

Listing Courtesy of FANNIE HILLMAN & ASSOCIATES

{$agent->Name}

Fusilier Realty Group
9145 Narcoossee Road
Orlando FL, 32827
Office: 407-281-8455

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Nov 2, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

147 Virginia Drive, Winter Park, FL 32789

Price$4,595,000

Est. Mortgage: $/month

MLS Number O5493376

  • Single Family Residential
  • Area Winter Park
  • Address 147 Virginia Drive
  • Square Feet 7,224
  • Year Built 1925

Listing Courtesy of COLDWELL BANKER RESIDENTIAL RE

{$agent->Name}

Fusilier Realty Group
9145 Narcoossee Road
Orlando FL, 32827
Office: 407-281-8455

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Nov 2, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

935 Greentree Drive, Winter Park, FL 32789

Price$4,200,000

Est. Mortgage: $/month

MLS Number O5544810

  • Single Family Residential
  • Area Winter Park
  • Address 935 Greentree Drive
  • Square Feet 4,975
  • Year Built 2006

Listing Courtesy of KELLY PRICE & COMPANY LLC

{$agent->Name}

Fusilier Realty Group
9145 Narcoossee Road
Orlando FL, 32827
Office: 407-281-8455

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Nov 2, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

1316 Green Cove Road, Winter Park, FL 32789

Price$3,995,000

Est. Mortgage: $/month

MLS Number O5549098

  • Single Family Residential
  • Area Winter Park
  • Address 1316 Green Cove Road
  • Square Feet 6,763
  • Year Built 1991

Listing Courtesy of KELLY PRICE & COMPANY LLC

{$agent->Name}

Fusilier Realty Group
9145 Narcoossee Road
Orlando FL, 32827
Office: 407-281-8455

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Nov 2, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

645 N Park Avenue, Winter Park, FL 32789

Price$3,800,000

Est. Mortgage: $/month

Pending

MLS Number O5465150

  • Single Family Residential
  • Area Winter Park
  • Address 645 N Park Avenue
  • Square Feet 4,232
  • Year Built 2017

Listing Courtesy of COLDWELL BANKER RESIDENTIAL RE

{$agent->Name}

Fusilier Realty Group
9145 Narcoossee Road
Orlando FL, 32827
Office: 407-281-8455

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Nov 2, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

633 N Park Avenue, Winter Park, FL 32789

Price$3,600,000

Est. Mortgage: $/month

Pending

MLS Number O5451780

  • Single Family Residential
  • Area Winter Park
  • Address 633 N Park Avenue
  • Square Feet 4,236
  • Year Built 2017

Listing Courtesy of COLDWELL BANKER RESIDENTIAL RE

{$agent->Name}

Fusilier Realty Group
9145 Narcoossee Road
Orlando FL, 32827
Office: 407-281-8455

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.03% last updated on Nov 2, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details