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

Winter Park FL Real Estate

Winter Park is a city in Orange County filled with arts and culture. There are more than 70 parks in the area, which are home to year-round events, festivals, and other activities. Park Avenue has many unique shops, fine restaurants, art galleries, and museums. Search below to find the latest Winter Park real estate listings.

Call us at 407.509.3812 or contact us online with any questions or to schedule a private viewing.

Get Ahead - Create an account to save your favorite listings and updates when similar properties hit the market.

866 Via Lugano Winter Park FL 32789

Price$7,895,000

Est. Mortgage: $/month

MLS Number O5750241

  • Single Family Residential
  • Area 32789 - Winter Park
  • Address 866 Via Lugano
  • Square Feet 10,613
  • Parking Spaces 5

Listed by and of Premier Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.35% last updated on Feb 21, 2019
* 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

570 Seminole Drive Winter Park FL 32789

Price$6,500,000

Est. Mortgage: $/month

MLS Number O5439246

  • Land
  • Area 32789 - Winter Park
  • Subdivision Winter Park Old Town
  • High School Winter Park High
  • Junior High Maitland Middle

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.

Listed by and of STOCKWORTH REALTY GROUP

$
$
%
$/month over payments
Federal 30-year interest rate: 4.35% last updated on Feb 21, 2019
* 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

1360 Alabama Dr Winter Park FL 32789

Price$6,500,000

Est. Mortgage: $/month

MLS Number O5749462

  • Single Family Residential
  • Area 32789 - Winter Park
  • Address 1360 Alabama Dr
  • Square Feet 10,600
  • Parking Spaces 4

Listed by and of KELLY PRICE & COMPANY LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 4.35% last updated on Feb 21, 2019
* 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

472-510 W Swoope Avenue Winter Park FL 32789

Price$6,000,000

Est. Mortgage: $/month

MLS Number O5730156

  • Land
  • Area 32789 - Winter Park
  • Subdivision Winter Park
  • High School Winter Park High
  • Junior High Maitland Middle

Attention all developers! Multifamily development site located two blocks to Park Avenue and two blocks to Winter Park Village! This site encompasses 3 contiguous properties totaling 87,500 SF. 1. 472-510 Swoope - Vacant Lot 150 x 250 on Swoope (zoned R3), 2. 435 W. Canton - Vacant Lot 50 x 250 (zoned R3) on Canton, and the 11,000 SF single story modern home on a 150 x 250 lot at 511 W. Canton separately listed as O5756452. This package includes a total land area of 87,500 SF - allowing for 20 townhomes in addition to the house.

Listed by and of CHARLES RUTENBERG REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 4.35% last updated on Feb 21, 2019
* 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

1821 Pinetree Road Winter Park FL 32789

Price$4,995,000

Est. Mortgage: $/month

MLS Number O5724510

  • Single Family Residential
  • Area 32789 - Winter Park
  • Address 1821 Pinetree Road
  • Square Feet 5,006
  • Parking Spaces 2

Listed by and of KELLER WILLIAMS WINTER PARK

$
$
%
$/month over payments
Federal 30-year interest rate: 4.35% last updated on Feb 21, 2019
* 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$4,795,000

Est. Mortgage: $/month

MLS Number O5763783

  • Single Family Residential
  • Area 32789 - Winter Park
  • Address 1941 Legion Drive
  • Square Feet 9,692
  • Parking Spaces 5

Listed by and of KELLER WILLIAMS WINTER PARK

$
$
%
$/month over payments
Federal 30-year interest rate: 4.35% last updated on Feb 21, 2019
* 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$4,750,000

Est. Mortgage: $/month

MLS Number O5734401

  • Single Family Residential
  • Area 32789 - Winter Park
  • Address 115 Palmer Avenue
  • Square Feet 9,838
  • Parking Spaces 3

Listed by and of REGAL R.E. PROFESSIONALS LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 4.35% last updated on Feb 21, 2019
* 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

935 Greentree Drive Winter Park FL 32789

Price$4,300,000

Est. Mortgage: $/month

MLS Number O5761045

  • Single Family Residential
  • Area 32789 - Winter Park
  • Address 935 Greentree Drive
  • Square Feet 4,975
  • Parking Spaces 3

Listed by and of COLDWELL BANKER RESIDENTIAL RE

$
$
%
$/month over payments
Federal 30-year interest rate: 4.35% last updated on Feb 21, 2019
* 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

1400 Green Cove Road Winter Park FL 32789

Price$3,995,000

Est. Mortgage: $/month

MLS Number O5750309

  • Single Family Residential
  • Area 32789 - Winter Park
  • Address 1400 Green Cove Road
  • Square Feet 6,384
  • Parking Spaces 2

Listed by and of FANNIE HILLMAN & ASSOCIATES

$
$
%
$/month over payments
Federal 30-year interest rate: 4.35% last updated on Feb 21, 2019
* 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

472 Henkel Circle Winter Park FL 32789

Price$3,695,000

Est. Mortgage: $/month

MLS Number O5731923

  • Single Family Residential
  • Area 32789 - Winter Park
  • Address 472 Henkel Circle
  • Square Feet 4,686
  • Parking Spaces 3

Listed by and of Sawruk Realty LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 4.35% last updated on Feb 21, 2019
* 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

2170 W Fawsett Road Winter Park FL 32789

Price$3,500,000

Est. Mortgage: $/month

MLS Number O5714430

  • Single Family Residential
  • Area 32789 - Winter Park
  • Address 2170 W Fawsett Road
  • Square Feet 6,589
  • Parking Spaces 2

Listed by and of Premier Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.35% last updated on Feb 21, 2019
* 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

2742 Lake Howell Lane Winter Park FL 32792

Price$3,499,000

Est. Mortgage: $/month

Pending

MLS Number O5755151

  • Single Family Residential
  • Square Feet 7,666
  • Parking Spaces 3
  • Bathroom 8
  • Bedrooms 6

Listed by Wendy Maher of Premier Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.35% last updated on Feb 21, 2019
* 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