WINDWARD SQUARE Condos For Sale
Currently, there are 5 active listings in WINDWARD SQUARE
priced from $225,000 to $320,000. Over the last 180 days,
2 Condos have been reported as sold in WINDWARD SQUARE. Final sale price ranged from $250,000 up to $285,000 pending possible revisions. The median sale price was $267,500 with a median Price Per Square Foot of $244.
- Min List Price: $225,000
- Max List Price: $320,000
- Active Listings: 5
- WINTER PARK, FL 32792
- Gated/Security
- Pool
- Exercise Room
- One Story
- Assigned Parking
- Year Built: 1979
Looking to buy?
2401 ANTILLES DRIVE WINTER PARK FL 32792
Status:
ACTIVE List Price:
$320,000 3 Bedrooms 2 Baths 1719 Sq Ft 1977 Year
MLS: O6357934
2401 ANTILLES DRIVE
WINTER PARK FL 32792
Community:
WINDWARD SQUARE| Status: ACTIVE | List Price: $320,000 |
| 3 Bedrooms | 2 Baths |
| 1719 Sq Ft |
1977 Year |
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
2487 HARBOUR WAY WINTER PARK FL 32792
Status:
ACTIVE List Price:
$319,900 3 Bedrooms 3 Baths 1803 Sq Ft 1978 Year
MLS: O6303931
2487 HARBOUR WAY
WINTER PARK FL 32792
Community:
WINDWARD SQUARE| Status: ACTIVE | List Price: $319,900 |
| 3 Bedrooms | 3 Baths |
| 1803 Sq Ft |
1978 Year |
Unmissable opportunity in Winter Park!
Beautiful house for sale with 3 bedrooms and 3 bathrooms, perfect for those seeking comfort, convenience and quality of life.
Located in one of the most sought-after areas of Winter Park, with an excellent location, close to schools, shops, restaurants, parks and much more!
The community offers a complete infrastructure with a swimming pool, playground, sidewalks for walking and a family environment ideal for all ages.
Don't miss this chance ...
Listing Courtesy of WRA BUSINESS & REAL ESTATE
2519 WINDWARD WAY WINTER PARK FL 32792
Status:
ACTIVE List Price:
$292,500 2 Bedrooms 2 Baths 1105 Sq Ft 1976 Year
MLS: O6392291
2519 WINDWARD WAY
WINTER PARK FL 32792
Community:
WINDWARD SQUARE| Status: ACTIVE | List Price: $292,500 |
| 2 Bedrooms | 2 Baths |
| 1105 Sq Ft |
1976 Year |
Welcome to 2519 Windward Way, a beautifully maintained single-story townhome located in the highly sought-after Windward Square community in Winter Park. This move-in ready residence offers 2 bedrooms, 2 bathrooms, plus a versatile office. Step inside to an open-concept floor plan designed for both everyday living and effortless entertaining. The spacious layout flows seamlessly into a well-appointed kitchen featuring gleaming stone countertops, stainless steel appliances, and ample storage ...
Listing Courtesy of NONA LEGACY POWERED BY LA ROSA
2530 LEEWARD WAY WINTER PARK FL 32792
Status:
ACTIVE List Price:
$265,000 2 Bedrooms 2 Baths 1199 Sq Ft 1976 Year
MLS: O6380907
2530 LEEWARD WAY
WINTER PARK FL 32792
Community:
WINDWARD SQUARE| Status: ACTIVE | List Price: $265,000 |
| 2 Bedrooms | 2 Baths |
| 1199 Sq Ft |
1976 Year |
Well-maintained 2-bedroom, 2-bath home with 1,199 sq ft in a desirable Winter Park 32792 location offering a fenced backyard, low HOA, and a flexible bonus space ideal for a home office, study, or hobby area. The functional split-bedroom layout provides privacy, while the open living and dining areas create a comfortable space for everyday living or entertaining. The kitchen offers ample cabinetry and counter space, flowing seamlessly to the main living area plus upgraded appliances. The ...
Listing Courtesy of WEMERT GROUP REALTY LLC
2400 DOMINICA RUN WINTER PARK FL 32792
Status:
ACTIVE List Price:
$225,000 2 Bedrooms 1 Bath 854 Sq Ft 1979 Year
MLS: O6394406
2400 DOMINICA RUN
WINTER PARK FL 32792
Community:
WINDWARD SQUARE| Status: ACTIVE | List Price: $225,000 |
| 2 Bedrooms | 1 Bath |
| 854 Sq Ft |
1979 Year |
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
| MLS | Address | List Price |
Beds |
Baths |
Sq Ft |
Year |
|---|
| O6357934 | 2401 ANTILLES DRIVE | $320,000 |
3 |
2 |
1719 |
1977 |
| O6303931 | 2487 HARBOUR WAY | $319,900 |
3 |
3 |
1803 |
1978 |
| O6392291 | 2519 WINDWARD WAY | $292,500 |
2 |
2 |
1105 |
1976 |
| O6380907 | 2530 LEEWARD WAY | $265,000 |
2 |
2 |
1199 |
1976 |
| O6394406 | 2400 DOMINICA RUN | $225,000 |
2 |
1 |
854 |
1979 |
Pending: WINDWARD SQUARE Condos for Sale
| MLS | Address | List Price |
Beds |
Baths |
Sq Ft |
Year |
|---|
| O6387369 | 2612 EXUMA WAY | $275,000 |
2 |
2 |
1020 |
1978 |
Condo Mania Agent:
Anna Lohr
Urbanista
Davich Lohr Team
Phone: 321-277-4797
Contact Anna
Condo Mania Agent:
Anna Lohr
Urbanista
Davich Lohr Team
Phone: 321-277-4797
Contact Anna
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Recently Sold Condos in WINDWARD SQUARE
Over the last 180 days,
2 Condos have been reported as sold in WINDWARD SQUARE. Final sale price ranged from $250,000 up to $285,000 pending possible revisions. The median sale price was $267,500 with a median Price Per Square Foot of $244.
With currently 5 active listings, the absorption rate for this community is approximately 15 months of inventory. More than four months supply of Condos for sale means it's a buyers market
and some sellers may be motivated.| 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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Last Updated: 2026-03-27 18:11:09
Orlando Condo Mania
MLS # O6357934
MLS # O6303931
MLS # O6392291
MLS: O6380907
MLS: O6394406