Winter Park - Sold Listings

257 Results
Property photo for 1333 S DENNING DRIVE, Winter Park, FL
$365,000
Closed
1333 S DENNING DRIVE, Winter Park, FL 32789
2 Bed 1 Bath 702 sq ft
Offered By: KELLER WILLIAMS WINTER PARK Listing from My Florida Regional MLS DBA Stellar MLS as distributed by MLS GRID
MLS attribution image
Property photo for 2881 TEMPLE TRAIL, Winter Park, FL
$560,000
Closed
2881 TEMPLE TRAIL, Winter Park, FL 32789
2 Bed 3 Bath 1,704 sq ft
Offered By: FANNIE HILLMAN & ASSOCIATES Listing from My Florida Regional MLS DBA Stellar MLS as distributed by MLS GRID
MLS attribution image
Property photo for 531 W SWOOPE AVENUE, Winter Park, FL
$595,000
Closed
531 W SWOOPE AVENUE, Winter Park, FL 32789
2 Bed 2 Bath 1,188 sq ft
Offered By: STIRLING INTERNATIONAL REAL ES Listing from My Florida Regional MLS DBA Stellar MLS as distributed by MLS GRID
MLS attribution image
Property photo for 1456 E BROOKSHIRE COURT, Winter Park, FL
$447,000
Closed
1456 E BROOKSHIRE COURT, Winter Park, FL 32792
3 Bed 2 Bath 1,673 sq ft
Offered By: COMPASS FLORIDA LLC Listing from My Florida Regional MLS DBA Stellar MLS as distributed by MLS GRID
MLS attribution image
Property photo for 405 LAKE FAIR LANE, Winter Park, FL
$445,000
Closed
405 LAKE FAIR LANE, Winter Park, FL 32789
3 Bed 2 Bath 1,491 sq ft
Offered By: EXP REALTY LLC Listing from My Florida Regional MLS DBA Stellar MLS as distributed by MLS GRID
MLS attribution image
Property photo for 721 PANSY AVENUE, Winter Park, FL
$1,810,000
Closed
721 PANSY AVENUE, Winter Park, FL 32789
4 Bed 4 Bath 2,653 sq ft
Offered By: PREMIER SOTHEBY'S INTL. REALTY Listing from My Florida Regional MLS DBA Stellar MLS as distributed by MLS GRID
MLS attribution image
Property photo for 1870 WALKER AVENUE, Winter Park, FL
$1,035,000
Closed
1870 WALKER AVENUE, Winter Park, FL 32789
3 Bed 3 Bath 2,046 sq ft
Offered By: PREMIER SOTHEBY'S INTL. REALTY Listing from My Florida Regional MLS DBA Stellar MLS as distributed by MLS GRID
MLS attribution image
Property photo for 2653 CAYMAN WAY, Winter Park, FL
$284,000
Closed
2653 CAYMAN WAY, Winter Park, FL 32792
3 Bed 2 Bath 1,284 sq ft
Offered By: RE/MAX TOWN & COUNTRY REALTY Listing from My Florida Regional MLS DBA Stellar MLS as distributed by MLS GRID
MLS attribution image
Property photo for 758 WARRENTON ROAD, Winter Park, FL
$315,000
Closed
758 WARRENTON ROAD, Winter Park, FL 32792
3 Bed 2 Bath 1,196 sq ft
Offered By: SUN PROPERTIES, INC. Listing from My Florida Regional MLS DBA Stellar MLS as distributed by MLS GRID
MLS attribution image
Property photo for 3019 ANTIQUE OAKS CIRCLE, #124, Winter Park, FL
$132,500
Closed
3019 ANTIQUE OAKS CIRCLE, #124, Winter Park, FL 32792
1 Bed 1 Bath 749 sq ft
Offered By: COLDWELL BANKER REALTY Listing from My Florida Regional MLS DBA Stellar MLS as distributed by MLS GRID
MLS attribution image
Property photo for 3014 ANTIQUE OAKS CIRCLE, #120, Winter Park, FL
$145,000
Closed
3014 ANTIQUE OAKS CIRCLE, #120, Winter Park, FL 32792
1 Bed 1 Bath 749 sq ft
Offered By: DON ASHER & ASSOCIATES, INC. Listing from My Florida Regional MLS DBA Stellar MLS as distributed by MLS GRID
MLS attribution image
Property photo for 913 CAMELLIA AVENUE, Winter Park, FL
$647,500
Closed
913 CAMELLIA AVENUE, Winter Park, FL 32789
3 Bed 3 Bath 1,389 sq ft
Offered By: PREMIER SOTHEBY'S INTL. REALTY Listing from My Florida Regional MLS DBA Stellar MLS as distributed by MLS GRID
MLS attribution image
Property photo for 228 RIPPLING LANE, Winter Park, FL
$580,000
Closed
228 RIPPLING LANE, Winter Park, FL 32789
3 Bed 2 Bath 1,618 sq ft
Offered By: GATE PROPERTIES & MANAGEMENT INC Listing from My Florida Regional MLS DBA Stellar MLS as distributed by MLS GRID
MLS attribution image
Property photo for 4437 GLENMOOR COURT, Winter Park, FL
$523,500
Closed
4437 GLENMOOR COURT, Winter Park, FL 32792
3 Bed 2 Bath 2,633 sq ft
Offered By: TAL BUSIDAN PA Listing from My Florida Regional MLS DBA Stellar MLS as distributed by MLS GRID
MLS attribution image
Property photo for 1750 WALNUT AVENUE, Winter Park, FL
$1,950,000
Closed
1750 WALNUT AVENUE, Winter Park, FL 32789
4 Bed 5 Bath 3,691 sq ft
Offered By: PALMANO GROUP RE BROKERAGE LLC Listing from My Florida Regional MLS DBA Stellar MLS as distributed by MLS GRID
MLS attribution image
Property photo for 7509 GLENMOOR LANE, Winter Park, FL
$485,000
Closed
7509 GLENMOOR LANE, Winter Park, FL 32792
3 Bed 2 Bath 2,067 sq ft
Offered By: RE/MAX PRIME PROPERTIES Listing from My Florida Regional MLS DBA Stellar MLS as distributed by MLS GRID
MLS attribution image
Property photo for 291 LEWFIELD CIRCLE, #291, Winter Park, FL
$130,000
Closed
291 LEWFIELD CIRCLE, #291, Winter Park, FL 32792
1 Bed 1 Bath 678 sq ft
Offered By: WATSON REALTY CORP Listing from My Florida Regional MLS DBA Stellar MLS as distributed by MLS GRID
MLS attribution image
Property photo for 2052 LEANNE COURT, Winter Park, FL
$440,000
Closed
2052 LEANNE COURT, Winter Park, FL 32792
4 Bed 2 Bath 2,264 sq ft
Offered By: OPENDOOR BROKERAGE LLC Listing from My Florida Regional MLS DBA Stellar MLS as distributed by MLS GRID
MLS attribution image
Property photo for 2500 LEE ROAD, #208, Winter Park, FL
$160,000
Closed
2500 LEE ROAD, #208, Winter Park, FL 32789
2 Bed 2 Bath 956 sq ft
Offered By: KELLER WILLIAMS REALTY AT THE PARKS Listing from My Florida Regional MLS DBA Stellar MLS as distributed by MLS GRID
MLS attribution image
Property photo for 5444 PEACO PLACE, Winter Park, FL
$245,000
Closed
5444 PEACO PLACE, Winter Park, FL 32792
2 Bed 2 Bath 924 sq ft
Offered By: KELLER WILLIAMS ADVANTAGE 2 REALTY Listing from My Florida Regional MLS DBA Stellar MLS as distributed by MLS GRID
MLS attribution image
Property photo for 2323 DEVON COURT, Winter Park, FL
$407,000
Closed
2323 DEVON COURT, Winter Park, FL 32789
4 Bed 2 Bath 2,403 sq ft
Offered By: CREEGAN GROUP Listing from My Florida Regional MLS DBA Stellar MLS as distributed by MLS GRID
MLS attribution image
Property photo for 2824 WOODSIDE AVENUE, Winter Park, FL
$536,500
Closed
2824 WOODSIDE AVENUE, Winter Park, FL 32789
2 Bed 2 Bath 912 sq ft
Offered By: PARKSIDE PROPERTIES, LLC Listing from My Florida Regional MLS DBA Stellar MLS as distributed by MLS GRID
MLS attribution image
Property photo for 241 W LAKE SUE AVENUE, Winter Park, FL
$960,375
Closed
241 W LAKE SUE AVENUE, Winter Park, FL 32789
3 Bed 3 Bath 2,304 sq ft
Offered By: COLDWELL BANKER REALTY Listing from My Florida Regional MLS DBA Stellar MLS as distributed by MLS GRID
MLS attribution image
Property photo for 2025 SUMMERLAND AVENUE, Winter Park, FL
$5,410,000
Closed
2025 SUMMERLAND AVENUE, Winter Park, FL 32789
5 Bed 5 Bath 4,432 sq ft
Offered By: PREMIER SOTHEBY'S INTL. REALTY Listing from My Florida Regional MLS DBA Stellar MLS as distributed by MLS GRID
MLS attribution image
Scroll for more

Copyright 2026 My Florida Regional MLS DBA Stellar MLS. All rights reserved. Information deemed reliable but is not guaranteed. The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of My Florida Regional MLS DBA Stellar MLS. Real estate listings held by brokerage firms other than the owner of this page include the name of the listing broker. Information provided is for consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. This site will be monitored for 'scraping' and any use of search facilities of data on the site other than by a consumer looking to purchase real estate is prohibited. Listing broker has attempted to offer accurate data, but buyers are advised to confirm all items. Information last updated on October 21, 2026 02:49 AM - ET

My Florida Regional MLS DBA Stellar MLS Logo

Based on information submitted to the MLS GRID as of October 21, 2026 02:49 AM - ET. 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. Properties displayed may be listed or sold by various participants in the MLS. Some listings have been excluded from this website.

IDX information is provided exclusively for consumers’ personal noncommercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, that the data is deemed reliable but is not guaranteed by MLS GRID, and that the use of the MLS GRID Data may be subject to an end user license agreement prescribed by the Member Participant’s applicable MLS if any and as amended from time to time.


View Map