Winter Park, FL Homes & Real Estate for Sale

Page 16 of 22
424 listings
1981 BLUE RIDGE ROAD, Winter Park, FL 32789
Single-Family Home

$1,150,000

  • 4 bed |
  • 2 bath |
  • 2,750 sqft |
  • 0.33 acre lot
1981 BLUE RIDGE ROAD Winter Park, FL 32789

#O6402961 - COMPASS FLORIDA LLC

726/720 N PENNSYLVANIA AVENUE, Winter Park, FL 32789
Duplex For Sale

$1,185,999

  • 6 bed |
  • 4 bath |
  • 2,282 sqft |
726/720 N PENNSYLVANIA AVENUE Winter Park, FL 32789

#O6402984 - COMPASS FLORIDA LLC

1900 WINTER PARK ROAD, Winter Park, FL 32789
Single-Family Home

$799,000

  • 4 bed |
  • 2 bath |
  • 1,511 sqft |
1900 WINTER PARK ROAD Winter Park, FL 32789

#O6402566 - RE/MAX ASSURED

3440 ALLSTON LANE, Winter Park, FL 32792
Single-Family Home For Sale

$405,000

  • 3 bed |
  • 3 bath |
  • 1,533 sqft |
3440 ALLSTON LANE Winter Park, FL 32792

#O6401731 - EXIT GLOBAL REALTY

1287 VERDANT GLADE PLACE, Winter Park, FL 32792
Single-Family Home For Sale

$775,000

  • 4 bed |
  • 4 bath |
  • 3,020 sqft |
1287 VERDANT GLADE PLACE Winter Park, FL 32792

#O6400331 - KELLER WILLIAMS REALTY AT THE PARKS

2838 WRIGHT AVENUE, Winter Park, FL 32789
Single-Family Home For Sale

$2,399,000

  • 5 bed |
  • 5 bath |
  • 3,479 sqft |
2838 WRIGHT AVENUE Winter Park, FL 32789

#O6399931 - PREMIER SOTHEBY'S INTL. REALTY

446 MELROSE AVENUE, Winter Park, FL 32789
Single-Family Home For Sale

$1,625,000

  • 4 bed |
  • 2 bath |
  • 2,640 sqft |
446 MELROSE AVENUE Winter Park, FL 32789

#O6402113 - PREMIER SOTHEBY'S INTL. REALTY

2383 SUN VALLEY CIRCLE 2383, Winter Park, FL 32792
Condominium For Sale

$245,000

  • 2 bed |
  • 2 bath |
  • 1,295 sqft |
2383 SUN VALLEY CIRCLE 2383 Winter Park, FL 32792

#O6400674 - WEICHERT REALTORS HALLMARK PROPERTIES

802 HAMILTON PLACE COURT, Winter Park, FL 32789
Single-Family Home For Sale

$1,295,000

  • 4 bed |
  • 4 bath |
  • 2,843 sqft |
802 HAMILTON PLACE COURT Winter Park, FL 32789

#O6398373 - FLORIDA CAPITAL REALTY

2317 SUN VALLEY CIRCLE 2317, Winter Park, FL 32792
Condominium For Sale

$267,000

  • 2 bed |
  • 2 bath |
  • 1,295 sqft |
2317 SUN VALLEY CIRCLE 2317 Winter Park, FL 32792

#O6398500 - SAND DOLLAR REALTY GROUP INC

1319 BESSMOR ROAD, Winter Park, FL 32789
Single-Family Home For Sale

$589,000

  • 3 bed |
  • 2 bath |
  • 1,126 sqft |
1319 BESSMOR ROAD Winter Park, FL 32789

#O6400395 - GALLOWAY REAL ESTATE

2361 MULBRY DRIVE, Winter Park, FL 32789
Single-Family Home

$2,249,000

  • 4 bed |
  • 4 bath |
  • 3,130 sqft |
2361 MULBRY DRIVE Winter Park, FL 32789

#O6396840 - COMPASS FLORIDA LLC

1398 GROVE TERRACE, Winter Park, FL 32789
Single-Family Home For Sale

$1,995,000

  • 4 bed |
  • 4 bath |
  • 3,450 sqft |
1398 GROVE TERRACE Winter Park, FL 32789

#O6399698 - ORANGE SLICE PROPERTIES

814 DENSMORE DR, Winter Park, FL 32792
Single-Family Home For Sale

$425,000

  • 4 bed |
  • 2 bath |
  • 1,610 sqft |
814 DENSMORE DR Winter Park, FL 32792

#O6399773 - ORANGE SLICE PROPERTIES

1741 WESTCHESTER AVENUE, Winter Park, FL 32789
Single-Family Home For Sale

$569,900

  • 3 bed |
  • 2 bath |
  • 1,434 sqft |
1741 WESTCHESTER AVENUE Winter Park, FL 32789

#O6399014 - PREMIER SOTHEBY'S INTL. REALTY

811 OVERSPIN DRIVE, Winter Park, FL 32789
Single-Family Home For Sale

$349,000

  • 2 bed |
  • 1 bath |
  • 749 sqft |
811 OVERSPIN DRIVE Winter Park, FL 32789

#O6400009 - RICK SINGH REAL ESTATE

1441 CARDINAL COURT, Winter Park, FL 32789
Single-Family Home For Sale

$4,285,000

  • 4 bed |
  • 6 bath |
  • 4,066 sqft |
  • 0.36 acre lot
1441 CARDINAL COURT Winter Park, FL 32789

#O6399395 - CHARLES RUTENBERG REALTY ORLANDO

7454 WYNNEWOOD SQUARE 188, Winter Park, FL 32792
Condominium For Sale

$229,000

  • 3 bed |
  • 3 bath |
  • 1,151 sqft |
  • 2.13 acre lot
7454 WYNNEWOOD SQUARE 188 Winter Park, FL 32792

#O6386578 - APPLE REALTY

102 BELL PLACE, Winter Park, FL 32792
Single-Family Home For Sale

$1,349,000

  • 4 bed |
  • 4 bath |
  • 2,459 sqft |
102 BELL PLACE Winter Park, FL 32792

#O6398118 - KELLER WILLIAMS WINTER PARK

1565 FOREST AVENUE, Winter Park, FL 32789
Pending

$1,495,000

  • 4 bed |
  • 2 bath |
  • 2,163 sqft |
1565 FOREST AVENUE Winter Park, FL 32789

#O6398694 - NORDQUIST & COMPANY INC

Presented by - MBA Realty Group, Inc.

Popular Neighborhoods in Winter Park, FL

Popular Zip Codes in Winter Park, FL

Veterans United Homefront
IDX Listings courtesy of Stellar MLS as distributed by MLS GRID. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The use of the MLS GRID Data may be subject to an end user license agreement prescribed by the applicable MLS if any and as amended from time to time

Based on information submitted to the MLS GRID as of date and time noted. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Some IDX listings have been excluded from this website.

The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the “DMCA”) provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to DMCAnotice@MLSGrid.com.

The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner’s behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.

IDX Copyright 2026 My Florida Regional Multiple Listing Service DBA Stellar MLS. The real estate listing data marked with this icon comes from the IDX program of the Stellar MLS system. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Properties displayed may be listed or sold by various participants in the MLS. Data displayed may be a portion of, and not a complete set of all listings published in the MLS.

For questions call 1-833-252-8030

Copyright © 2026 MBA Realty Group, Inc. and Did You Serve, LLC. Homefront.com is NOT affiliated with any government agencies, including the VA. Homefront.com is a service of Did You Serve, LLC. Veterans United and the Veterans United House logo are registered trademarks of Mortgage Research Center, LLC, used under license agreement. Terms of Use.

Connect with an Agent
Get paired with a top VA-friendly agentGet an Agent