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Windy Pointe Houses Sold

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Ultra Luxury — Above $1,000 per SqFt
High-End — $650 - $1,000 per SqFt
Mid-Tier — $400 - $650 per SqFt
Premium — $300 - $400 per SqFt
Entry-Level — Below $300 per SqFt
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Results 29 of 91
Sold - Aug 17, 2026
Windy Pointe, 21553 SW 87th Ct #102, Cutler Bay, Florida 33189, image 1
$177,500
  • 1 Beds
  • 1 Baths
  • 770 SqFt
  • $231/SqFt
  • $633/mo HOA
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Condo sold in Windy Pointe
21553 SW 87th Ct #102, Cutler Bay, FL 33189
Listing Courtesy Of: 1Houzz, LLC.
Sold - Aug 11, 2026
Windy Pointe, 21525 SW 87th Ct, Cutler Bay, Florida 33189, image 1
$330,000
  • 2 Beds
  • 2 Baths
  • 1,082 SqFt
  • $305/SqFt
  • $172/mo HOA
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Townhouse sold in Windy Pointe
21525 SW 87th Ct, Cutler Bay, FL 33189
Listing Courtesy Of: Fathom Realty FL, LLC
Sold - May 11, 2026
Windy Pointe, 8858 SW 214th St, Cutler Bay, Florida 33189, image 1
$545,000
  • 3 Beds
  • 2 Baths
  • 1,394 SqFt
  • $391/SqFt
  • $120/mo HOA
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House sold in Windy Pointe
8858 SW 214th St, Cutler Bay, FL 33189
Listing Courtesy Of: Luxe Properties
Sold - Mar 27, 2026
Windy Pointe, 8740 SW 214th Ter, Cutler Bay, Florida 33189, image 1
$570,000$25K
  • 4 Beds
  • 21/2 Baths
  • 1,824 SqFt
  • $313/SqFt
  • $187/mo HOA
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House sold in Windy Pointe
8740 SW 214th Ter, Cutler Bay, FL 33189
Listing Courtesy Of: 7 Group Realty, Inc
Sold - Jan 2, 2026
Windy Pointe, 21472 SW 87th Pl, Cutler Bay, Florida 33189, image 1
$480,000
  • 3 Beds
  • 2 Baths
  • 1,258 SqFt
  • $382/SqFt
  • $198/mo HOA
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House sold in Windy Pointe
21472 SW 87th Pl, Cutler Bay, FL 33189
Listing Courtesy Of: Luxe Properties
Sold - Sep 12, 2025
Windy Pointe, 8711 SW 214th St, Cutler Bay, Florida 33189, image 1
$525,000
  • 3 Beds
  • 3 Baths
  • 1,388 SqFt
  • $378/SqFt
  • $213/mo HOA
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House for sale in Windy Pointe
8711 SW 214th St, Cutler Bay, FL 33189
Listing Courtesy Of: Keller Williams Legacy
Sold - Aug 22, 2025
Windy Pointe, 21479 SW 87th Ct, Cutler Bay, Florida 33189, image 1
$405,000$10K
  • 3 Beds
  • 2 Baths
  • 1,401 SqFt
  • $289/SqFt
  • $155/mo HOA
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House for sale in Windy Pointe
21479 SW 87th Ct, Cutler Bay, FL 33189
Listing Courtesy Of: Residenzea LLC
Sold - Aug 4, 2025
Windy Pointe, 21496 SW 87th Pl, Cutler Bay, Florida 33189, image 1
$495,000$55K
  • 3 Beds
  • 2 Baths
  • 1,258 SqFt
  • $393/SqFt
  • $198/mo HOA
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House for sale in Windy Pointe
21496 SW 87th Pl, Cutler Bay, FL 33189
Listing Courtesy Of: Lifestyle International Realty
Sold - Jul 3, 2025
Windy Pointe, 21532 SW 88th Pl, Cutler Bay, Florida 33189, image 1
$495,000$55K
  • 3 Beds
  • 2 Baths
  • 1,394 SqFt
  • $355/SqFt
  • $140/mo HOA
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House for sale in Windy Pointe
21532 SW 88th Pl, Cutler Bay, FL 33189
Listing Courtesy Of: The Keyes Company
Sold - Mar 28, 2025
Windy Pointe, 21517 SW 87th Ct, Cutler Bay, Florida 33189, image 1
$397,000$3K
  • 2 Beds
  • 2 Baths
  • 1,082 SqFt
  • $367/SqFt
  • $68/mo HOA
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Townhouse for sale in Windy Pointe
21517 SW 87th Ct, Cutler Bay, FL 33189
Listing Courtesy Of: La Familia Real Estate Inc.
Sold - Dec 10, 2024
Windy Pointe, 21451 SW 88th Ave, Cutler Bay, Florida 33189, image 1
$485,000$30K
  • 3 Beds
  • 2 Baths
  • 1,394 SqFt
  • $348/SqFt
  • $140/mo HOA
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House for sale in Windy Pointe
21451 SW 88th Ave, Cutler Bay, FL 33189
Listing Courtesy Of: Ampuero Realty Corp.
Sold - Aug 26, 2024
Windy Pointe, 21442 SW 88th Pl, Cutler Bay, Florida 33189, image 1
$570,000$15K
  • 4 Beds
  • 21/2 Baths
  • 1,862 SqFt
  • $306/SqFt
  • $198/mo HOA
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House for sale in Windy Pointe
21442 SW 88th Pl, Cutler Bay, FL 33189
Listing Courtesy Of: Real Estate Craft, LLC.
Sold - Aug 5, 2024
Windy Pointe, 8795 SW 214th Ter, Cutler Bay, Florida 33189, image 1
$580,000$45K
  • 4 Beds
  • 21/2 Baths
  • 1,839 SqFt
  • $315/SqFt
  • $207/mo HOA
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House for sale in Windy Pointe
8795 SW 214th Ter, Cutler Bay, FL 33189
Listing Courtesy Of: Lifestyle International Realty
Sold - Aug 1, 2024
Windy Pointe, 21416 SW 87th Pl, Cutler Bay, Florida 33189, image 1
$624,000$61K
  • 4 Beds
  • 21/2 Baths
  • 1,824 SqFt
  • $342/SqFt
  • $139/mo HOA
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House for sale in Windy Pointe
21416 SW 87th Pl, Cutler Bay, FL 33189
Listing Courtesy Of: Century 21 World Connection
Sold - Apr 24, 2024
Windy Pointe, 8758 SW 215th Ter 0, Cutler Bay, Florida 33189, image 1
$423,000$2K
  • 3 Beds
  • 21/2 Baths
  • 1,562 SqFt
  • $271/SqFt
  • $165/mo HOA
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Townhouse for sale in Windy Pointe
8758 SW 215th Ter 0, Cutler Bay, FL 33189
Listing Courtesy Of: Coldwell Banker Realty
Sold - Apr 3, 2024
Windy Pointe, 21533 SW 87th Ct #102, Cutler Bay, Florida 33189, image 1
$225,000$22K
  • 1 Beds
  • 1 Baths
  • 770 SqFt
  • $292/SqFt
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Condo for sale in Windy Pointe
21533 SW 87th Ct #102, Cutler Bay, FL 33189
Listing Courtesy Of: EXP Realty, LLC
Sold - Apr 1, 2024
Windy Pointe, 21551 SW 87th Ct #101, Cutler Bay, Florida 33189, image 1
$225,000$13K
  • 1 Beds
  • 1 Baths
  • 680 SqFt
  • $331/SqFt
  • $724/mo HOA
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Condo for sale in Windy Pointe
21551 SW 87th Ct #101, Cutler Bay, FL 33189
Listing Courtesy Of: South Florida Real Estate Grp
Sold - Sep 22, 2023
Windy Pointe, 8797 SW 214th Ln, Cutler Bay, Florida 33189, image 1
$607,000
  • 4 Beds
  • 2 Baths
  • 1,824 SqFt
  • $333/SqFt
  • $110/mo HOA
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House for sale in Windy Pointe
8797 SW 214th Ln, Cutler Bay, FL 33189
Listing Courtesy Of: Luxe Properties
Sold - Aug 30, 2023
Windy Pointe, 8717 SW 213th Ter, Cutler Bay, Florida 33189, image 1
$550,000$20K
  • 3 Beds
  • 2 Baths
  • 1,515 SqFt
  • $363/SqFt
  • $126/mo HOA
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House for sale in Windy Pointe
8717 SW 213th Ter, Cutler Bay, FL 33189
Listing Courtesy Of: Global Luxury Realty LLC
Sold - Aug 23, 2023
Windy Pointe, 8713 SW 214th St, Cutler Bay, Florida 33189, image 1
$560,000$15K
  • 4 Beds
  • 2 Baths
  • 1,839 SqFt
  • $305/SqFt
  • $173/mo HOA
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House for sale in Windy Pointe
8713 SW 214th St, Cutler Bay, FL 33189
Listing Courtesy Of: M-Sec Realty, LLC
Sold - Aug 15, 2023
Windy Pointe, 8725 SW 213th Ter, Cutler Bay, Florida 33189, image 1
$525,000
  • 3 Beds
  • 2 Baths
  • 1,388 SqFt
  • $378/SqFt
  • $266/mo HOA
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House for sale in Windy Pointe
8725 SW 213th Ter, Cutler Bay, FL 33189
Listing Courtesy Of: Brown Harris Stevens
Sold - Jul 31, 2023
Windy Pointe, 8705 SW 214th St, Cutler Bay, Florida 33189, image 1
$550,000
  • 4 Beds
  • 2 Baths
  • 1,839 SqFt
  • $299/SqFt
  • $110/mo HOA
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House for sale in Windy Pointe
8705 SW 214th St, Cutler Bay, FL 33189
Listing Courtesy Of: Compass Florida, LLC.
Sold - Jul 13, 2023
Windy Pointe, 21521 SW 87th Ct, Cutler Bay, Florida 33189, image 1
$415,000
  • 3 Beds
  • 2 Baths
  • 1,125 SqFt
  • $369/SqFt
  • $148/mo HOA
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Townhouse for sale in Windy Pointe
21521 SW 87th Ct, Cutler Bay, FL 33189
Listing Courtesy Of: Keller Williams Capital Realty
Sold - Jun 9, 2023
Windy Pointe, 8754 SW 215th Ter #8754, Cutler Bay, Florida 33189, image 1
$345,000
  • 2 Beds
  • 2 Baths
  • 1,172 SqFt
  • $294/SqFt
  • $148/mo HOA
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Townhouse for sale in Windy Pointe
8754 SW 215th Ter #8754, Cutler Bay, FL 33189
Listing Courtesy Of: Luxe Properties
Sold - May 16, 2023
Windy Pointe, 21442 SW 88th Pl, Cutler Bay, Florida 33189, image 1
$500,000
  • 4 Beds
  • 21/2 Baths
  • 1,862 SqFt
  • $269/SqFt
  • $175/mo HOA
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House for sale in Windy Pointe
21442 SW 88th Pl, Cutler Bay, FL 33189
Listing Courtesy Of: Canvas Real Estate
Sold - May 11, 2023
Windy Pointe, 21395 SW 87th Ct, Cutler Bay, Florida 33189, image 1
$528,000
  • 4 Beds
  • 2 Baths
  • 1,839 SqFt
  • $287/SqFt
  • $110/mo HOA
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House for sale in Windy Pointe
21395 SW 87th Ct, Cutler Bay, FL 33189
Listing Courtesy Of: Vanguard Group Realty LLC
Sold - Apr 25, 2023
Windy Pointe, 8749 SW 214th Ln, Cutler Bay, Florida 33189, image 1
$500,000
  • 4 Beds
  • 21/2 Baths
  • 1,824 SqFt
  • $274/SqFt
  • $110/mo HOA
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House for sale in Windy Pointe
8749 SW 214th Ln, Cutler Bay, FL 33189
Listing Courtesy Of: United Real Estate Advisors
Sold - Mar 31, 2023
Windy Pointe, 8707 SW 214th St, Cutler Bay, Florida 33189, image 1
$465,000
  • 3 Beds
  • 2 Baths
  • 1,388 SqFt
  • $335/SqFt
  • $125/mo HOA
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House for sale in Windy Pointe
8707 SW 214th St, Cutler Bay, FL 33189
Listing Courtesy Of: Florida Platinum Group, LLC
Sold - Nov 16, 2022
Windy Pointe, 8795 SW 214th Ter, Cutler Bay, Florida 33189, image 1
$490,000$9K
  • 4 Beds
  • 21/2 Baths
  • 1,839 SqFt
  • $266/SqFt
  • $149/mo HOA
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House for sale in Windy Pointe
8795 SW 214th Ter, Cutler Bay, FL 33189
Listing Courtesy Of: Real Estate Craft, LLC.
1 - 29 of 91 Results

Subdivision Amenities

Clubhouse
Maintenance
Playground
Pool

HOA Cost Benchmark

$0.11 / Sq.Ft.

Monthly ownership cost
↑120%above peers
↓21%below city avg
This Community
$0.11
Comparable Entry-Level Avg
$0.05
Cutler Bay, FL Avg
$0.14
$0.00
$0.10
$0.20
Higher than peers, lower than the city average
Peer Set · 8 comparable communities
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Preconstruction in Cutler Bay

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Caribbean Isles 2
Caribbean Isles 2
Caribbean Isles 2
Condos
  • Units
    142
  • Stories
    8

Miami-based Caribbean Village LTD., an affiliate of Pinnacle Housing, hopes to get approval for revised plans regarding the second phase of Caribbean Isles.

The first phase, which finished construction in 2019, currently offers 123 units geared toward seniors. The second phase would offer 142 affordable housing units in an eight-story building. This is a 42 percent increase from the initially proposed 100 in 2022.

According to the South Florida Business Journal, plans call for the construction of 90 one-bedroom and 52 two-bedroom units, with communal amenities including a fitness center and club room. There would also be a two-story parking garage featuring 96 parking spots, averaging to less than one per unit. Behar Font & Partners designed the venture.

The second phase would take shape on a 3.23-acre site.

Caribbean Isles’ second phase is slated for 19755 S.W. 110th Court, Miami, FL, 33157, in Miami-Dade County. It’ll be west of the Florida Turnpike in the South Miami Heights neighborhood.

APARTMENT AMENITIES

  • LVT Flooring
  • Over the Range Microwave
  • Quartz Countertops
  • Tile Throughout
  • Energy Efficient Appliances
  • Ceiling Fans
  • Washer & Dryer (available for an additional fee)

COMMUNITY AMENITIES

  • BBQ Area
  • Smoke Free Community
  • Computer Workstations
  • Fitness Center
  • Elevators
  • Parcel Lockers
  • Community Room
  • Yoga Room
  • 24 Hour Maintenance Emergency Services
Details

Nearby Subdivisions

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0.22 miles
For Sale (4)
$595K - $599K
For Rent (1)
$5K - $5K
Premium
0.32 miles
For Sale (4)
$419K - $470K
For Rent (1)
$3K - $3K
Entry-Level
0.33 miles
For Sale (2)
$448K - $455K
For Rent (2)
$3K - $3K
Premium
0.40 miles
For Sale (4)
$499K - $655K
For Rent (4)
$3K - $4K

Schools

Scores

Walk Score®
Car-Dependent. Almost all errands require a car
20

100
Transit Score®
Minimal Transit. It is possible to get on a bus
22

100
Bike Score®
Somewhat Bikeable. Minimal bike infrastructure
49

100
Sound Score®
Very loud
74

100
Airport Score
Close to airports. Noticeable airport activity
0

100
Traffic Score
Congested area. Frequent traffic delays
34

100
Local Score
Limited local amenities nearby
0

100

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