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WINDWARD SQUARE Condos For Sale

More Details about MLS # O6357934 : 2401 ANTILLES DRIVE MLS # O6357934
Active Listing
Asking Price is $320,000

More Details about MLS # O6394406 : 2400 DOMINICA RUN MLS # O6394406
Active Listing
Asking Price is $225,000

More Details about MLS # O6392291 : 2519 WINDWARD WAY MLS # O6392291
Pending Listing
Asking Price is $279,500

Currently, there are 2 active listings in WINDWARD SQUARE priced from $225,000 to $320,000. Over the last 180 days there has been only 1 reported sale in WINDWARD SQUARE. A 2 bedroom, 1 bath Condo sold for $250,000.


  • Min List Price: $225,000
  • Max List Price: $320,000
  • Active Listings: 2
  • WINTER PARK, FL 32792
  • Gated/Security
  • Pool
  • Exercise Room
  • One Story
  • Assigned Parking
  • Year Built: 1979

Looking to buy?

WINTER PARK > WINDWARD SQUARE > MLS #: O6357934

2401 ANTILLES DRIVE WINTER PARK FL 32792
Status: ACTIVE   List Price: $320,000   3 Bedrooms   2 Baths   1719 Sq Ft    1977 Year

MLS: O6357934
Primary Photo for MLS#: O6357934

2401 ANTILLES DRIVE
WINTER PARK FL 32792
Community: WINDWARD SQUARE
Status: ACTIVEList Price: $320,000
3 Bedrooms2 Baths
1719 Sq Ft 1977 Year

Primary Photo for MLS#: O6357934MLS: O6357934

Fantastic end unit with enclosed Florida Room in the sought after Windward Square! This 3/2 features several updates including a, updated kitchen with 42" wood cabinets, granite counters and a center island! Most rooms have upgraded ceiling fans from Dan”s Fans with a lifetime guarantee. The home has newer A/C, high impact windows and the home has been re-piped for your peace of mind. This is a wonderful space and great to prep for a dinner party! Open floor concept with dining room and ...

Listing Courtesy of KELLER WILLIAMS REALTY AT THE PARKS

WINTER PARK > WINDWARD SQUARE > MLS #: O6394406

2400 DOMINICA RUN WINTER PARK FL 32792
Status: ACTIVE   List Price: $225,000   2 Bedrooms   1 Bath   854 Sq Ft    1979 Year

MLS: O6394406
Primary Photo for MLS#: O6394406

2400 DOMINICA RUN
WINTER PARK FL 32792
Community: WINDWARD SQUARE
Status: ACTIVEList Price: $225,000
2 Bedrooms1 Bath
854 Sq Ft 1979 Year

Primary Photo for MLS#: O6394406MLS: O6394406

CHARMING 2/1 MOVE IN READY TOWNHOME in highly sought-after Windward Square community of Winter Park! NEWER Roof 2025! Spacious floor plan with soaring ceilings! Inviting entertainment space with dining/living combo off kitchen. Ample natural light fills this home with double glass sliders and multiple skylights all in living area! Relaxing views of back park like green space! Convenient location near major highways, the Orlando International Airport, shopping, dining, universities and ...

Listing Courtesy of FLORIDA HOME TEAM REALTY LLC

Active WINDWARD SQUARE Condos for Sale

MLSAddressList Price Beds Baths Sq Ft Year
O63579342401 ANTILLES DRIVE $320,000 3 2 1719 1977
O63944062400 DOMINICA RUN $225,000 2 1 854 1979

Pending: WINDWARD SQUARE Condos for Sale

MLSAddressList Price Beds Baths Sq Ft Year
O63922912519 WINDWARD WAY $279,500 2 2 1105 1976
O63809072530 LEEWARD WAY $265,000 2 2 1199 1976

Condo Mania Agent:
Anna Lohr

Featured Real Estate Agent Anna Lohr

Urbanista
Davich Lohr Team
Phone: 321-277-4797

Contact Anna

Featured Real Estate Agent Anna Lohr

Condo Mania Agent:
Anna Lohr
Urbanista
Davich Lohr Team
Phone: 321-277-4797

Contact Anna

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Listing Locations

Recently Sold Condos in WINDWARD SQUARE

Over the last 180 days there has been only 1 reported sale in WINDWARD SQUARE. A 2 bedroom, 1 bath Condo sold for $250,000.
Address COE Date Sold Price $/SQFT Beds Baths
2399 ANTILLES DRIVE 2025-11-03 $250,000 $293 2 1
2462 HARBOUR WAY 2025-10-22 $285,000 $196 3 2
2517 WINDWARD WAY 2025-09-02 $272,500 $255 2 2
2426 WINDWARD WAY 2025-08-28 $270,000 $290 2 2
2398 DOMINICA RUN 2025-08-21 $255,000 $198 2 2
2541 LEEWARD WAY 2025-07-14 $290,000 $284 2 2
2464 HARBOUR WAY 2025-06-13 $265,000 $204 2 2
2539 ANTILLES DRIVE 2025-05-23 $284,000 $249 3 2
2529 LEEWARD WAY 2025-04-29 $235,000 $258 2 1
2337 ANTILLES DRIVE 2025-03-27 $249,900 $294 2 1


Detailed Analysis of Recently Sold Condos in WINDWARD SQUARE

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All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified.

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Information Deemed Reliable But Not Guaranteed. The information being 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 information, including square footage, while not guaranteed, has been acquired from sources believed to be reliable.

Last Updated: 2026-04-29 03:09:25