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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.

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866 Via Lugano Winter Park FL 32789

Price$7,895,000

Est. Mortgage: $/month

Pending

MLS Number O5750241

  • Single Family Residential
  • Area 32789 - Winter Park
  • Address 866 Via Lugano
  • Square Feet 10,613
  • Year Built 2015

Listing Courtesy of PREMIER SOTHEBYS INTL. REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 4.12% last updated on Apr 11, 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.

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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
  • Year Built 2009

Listing Courtesy of KELLY PRICE & COMPANY LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 4.12% last updated on Apr 11, 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.

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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.

Listing Courtesy of STOCKWORTH REALTY GROUP

$
$
%
$/month over payments
Federal 30-year interest rate: 4.12% last updated on Apr 11, 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.

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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.

Listing Courtesy of CHARLES RUTENBERG REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 4.12% last updated on Apr 11, 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.

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1821 Pinetree Road Winter Park FL 32789

Price$4,950,000

Est. Mortgage: $/month

MLS Number O5772377

  • Single Family Residential
  • Area 32789 - Winter Park
  • Address 1821 Pinetree Road
  • Square Feet 5,006
  • Year Built 2018

Listing Courtesy of KELLER WILLIAMS WINTER PARK

$
$
%
$/month over payments
Federal 30-year interest rate: 4.12% last updated on Apr 11, 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.

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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
  • Year Built 2008

Listing Courtesy of KELLER WILLIAMS WINTER PARK

$
$
%
$/month over payments
Federal 30-year interest rate: 4.12% last updated on Apr 11, 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.

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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
  • Year Built 1989

Listing Courtesy of REGAL R.E. PROFESSIONALS LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 4.12% last updated on Apr 11, 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.

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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
  • Year Built 2006

Listing Courtesy of COLDWELL BANKER RESIDENTIAL RE

$
$
%
$/month over payments
Federal 30-year interest rate: 4.12% last updated on Apr 11, 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.

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1013 Temple Grove Winter Park FL 32789

Price$3,995,000

Est. Mortgage: $/month

MLS Number O5766961

  • Single Family Residential
  • Area 32789 - Winter Park
  • Address 1013 Temple Grove
  • Square Feet 5,797
  • Year Built 1979

Listing Courtesy of PREMIER SOTHEBYS INTL. REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 4.12% last updated on Apr 11, 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.

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1400 Green Cove Road Winter Park FL 32789

Price$3,675,000

Est. Mortgage: $/month

MLS Number O5750309

  • Single Family Residential
  • Area 32789 - Winter Park
  • Address 1400 Green Cove Road
  • Square Feet 6,384
  • Year Built 1995

Listing Courtesy of FANNIE HILLMAN & ASSOCIATES

$
$
%
$/month over payments
Federal 30-year interest rate: 4.12% last updated on Apr 11, 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.

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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
  • Year Built 1925

Listing Courtesy of PREMIER SOTHEBYS INTL. REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 4.12% last updated on Apr 11, 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.

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409 Genius Drive Winter Park FL 32789

Price$3,450,000

Est. Mortgage: $/month

MLS Number O5775449

  • Single Family Residential
  • Area 32789 - Winter Park
  • Address 409 Genius Drive
  • Square Feet 7,433
  • Year Built 2007

Listing Courtesy of PREMIER SOTHEBYS INTL. REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 4.12% last updated on Apr 11, 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