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Montego Bay Houses Sold

Entry-Level
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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Selling Speed
Fast
29
Inventory Supply
Balanced
3.45
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Results 29 of 102
Sold - Oct 13, 2026
Montego Bay, 22101 SW 100th Pl, Cutler Bay, Florida 33190, image 1
$335,000
  • 2 Beds
  • 2 Baths
  • 1,136 SqFt
  • $295/SqFt
  • $119/mo HOA
Entry-Level
House sold in Montego Bay
22101 SW 100th Pl, Cutler Bay, FL 33190
Listing Courtesy Of: EXP Realty LLC
Sold - Sep 8, 2026
Montego Bay, 10001 SW 218th St, Cutler Bay, Florida 33190, image 1
$465,500
  • 3 Beds
  • 2 Baths
  • 1,425 SqFt
  • $327/SqFt
  • $339/mo HOA
Entry-Level
House sold in Montego Bay
10001 SW 218th St, Cutler Bay, FL 33190
Listing Courtesy Of: Urbaniza Realty
Sold - Jul 9, 2026
Montego Bay, 21839 SW 100th Pl, Cutler Bay, Florida 33190, image 1
$479,800$101K
  • 3 Beds
  • 2 Baths
  • 1,650 SqFt
  • $291/SqFt
  • $155/mo HOA
Entry-Level
House sold in Montego Bay
21839 SW 100th Pl, Cutler Bay, FL 33190
Listing Courtesy Of: EXP Realty, LLC
Sold - Jun 5, 2026
Montego Bay, 9928 SW 218th Ter, Cutler Bay, Florida 33190, image 1
$575,000
  • 3 Beds
  • 2 Baths
  • 1,425 SqFt
  • $404/SqFt
  • $152/mo HOA
Entry-Level
House sold in Montego Bay
9928 SW 218th Ter, Cutler Bay, FL 33190
Listing Courtesy Of: Equity Real Property and Mgt.
Sold - Mar 9, 2026
Montego Bay, 9928 SW 218th Ter, Cutler Bay, Florida 33190, image 1
$405,000$15K
  • 3 Beds
  • 2 Baths
  • 1,425 SqFt
  • $284/SqFt
  • $130/mo HOA
Entry-Level
House sold in Montego Bay
9928 SW 218th Ter, Cutler Bay, FL 33190
Listing Courtesy Of: Mainstay Brokerage LLC
Sold - Feb 12, 2026
Montego Bay, 21808 SW 99th Ave, Cutler Bay, Florida 33190, image 1
$390,000$120K
  • 3 Beds
  • 21/2 Baths
  • 1,650 SqFt
  • $236/SqFt
  • $89/mo HOA
Entry-Level
House sold in Montego Bay
21808 SW 99th Ave, Cutler Bay, FL 33190
Listing Courtesy Of: Coldwell Banker Realty
Sold - Feb 9, 2026
Montego Bay, 10013 SW 218th St, Cutler Bay, Florida 33190, image 1
$453,000$47K
  • 3 Beds
  • 2 Baths
  • 1,558 SqFt
  • $291/SqFt
  • $150/mo HOA
Entry-Level
House sold in Montego Bay
10013 SW 218th St, Cutler Bay, FL 33190
Listing Courtesy Of: Trexy International Realty, Inc
Sold - Dec 22, 2025
Montego Bay, 10042 SW 220th St, Cutler Bay, Florida 33190, image 1
$443,500
  • 2 Beds
  • 2 Baths
  • 1,136 SqFt
  • $390/SqFt
  • $157/mo HOA
Entry-Level
House sold in Montego Bay
10042 SW 220th St, Cutler Bay, FL 33190
Listing Courtesy Of: Lifestyle International Realty
Sold - Sep 30, 2025
Montego Bay, 9916 SW 218th Ter, Cutler Bay, Florida 33190, image 1
$620,000
  • 4 Beds
  • 21/2 Baths
  • 1,808 SqFt
  • $343/SqFt
  • $105/mo HOA
Entry-Level
House for sale in Montego Bay
9916 SW 218th Ter, Cutler Bay, FL 33190
Listing Courtesy Of: Real Estate TeamMates LLC
Sold - Sep 15, 2025
Montego Bay, 9951 SW 218th Ter, Cutler Bay, Florida 33190, image 1
$505,000$45K
  • 3 Beds
  • 2 Baths
  • 1,425 SqFt
  • $354/SqFt
  • $161/mo HOA
Entry-Level
House for sale in Montego Bay
9951 SW 218th Ter, Cutler Bay, FL 33190
Listing Courtesy Of: Grand Beach Realty LLC
Sold - Aug 19, 2025
Montego Bay, 21760 SW 99th Pl, Cutler Bay, Florida 33190, image 1
$440,000
  • 2 Beds
  • 2 Baths
  • 1,136 SqFt
  • $387/SqFt
  • $147/mo HOA
Entry-Level
House for sale in Montego Bay
21760 SW 99th Pl, Cutler Bay, FL 33190
Listing Courtesy Of: Cutler Realty, Inc.
Sold - Jul 14, 2025
Montego Bay, 21820 SW 98th Pl, Cutler Bay, Florida 33190, image 1
$560,000
  • 4 Beds
  • 21/2 Baths
  • 1,506 SqFt
  • $372/SqFt
  • $152/mo HOA
Entry-Level
House for sale in Montego Bay
21820 SW 98th Pl, Cutler Bay, FL 33190
Listing Courtesy Of: Keller Williams Capital Realty
Sold - May 30, 2025
Montego Bay, 21664 SW 98th Pl, Cutler Bay, Florida 33190, image 1
$499,900$30K
  • 4 Beds
  • 3 Baths
  • 1,808 SqFt
  • $276/SqFt
  • $157/mo HOA
Entry-Level
House for sale in Montego Bay
21664 SW 98th Pl, Cutler Bay, FL 33190
Listing Courtesy Of: The Keyes Company
Sold - Apr 28, 2025
Montego Bay, 9921 SW 218th Ter, Cutler Bay, Florida 33190, image 1
$525,000$25K
  • 3 Beds
  • 2 Baths
  • 1,425 SqFt
  • $368/SqFt
  • $275/mo HOA
Entry-Level
Townhouse for sale in Montego Bay
9921 SW 218th Ter, Cutler Bay, FL 33190
Listing Courtesy Of: Realty Golden Group PA
Sold - Feb 28, 2025
Montego Bay, 9971 SW 218th Ter, Cutler Bay, Florida 33190, image 1
$515,000$515K
  • 3 Beds
  • 2 Baths
  • 1,425 SqFt
  • $361/SqFt
  • $157/mo HOA
Entry-Level
House for sale in Montego Bay
9971 SW 218th Ter, Cutler Bay, FL 33190
Listing Courtesy Of: London Foster Realty
Sold - Feb 13, 2025
Montego Bay, 21806 SW 98th Pl, Cutler Bay, Florida 33190, image 1
$449,000$21K
  • 2 Beds
  • 2 Baths
  • 1,136 SqFt
  • $395/SqFt
  • $79/mo HOA
Entry-Level
House for sale in Montego Bay
21806 SW 98th Pl, Cutler Bay, FL 33190
Listing Courtesy Of: Skyline Trust Realty, Inc
Sold - Oct 30, 2024
Montego Bay, 21736 SW 99th Ave, Cutler Bay, Florida 33190, image 1
$510,000
  • 3 Beds
  • 2 Baths
  • 1,425 SqFt
  • $358/SqFt
  • $157/mo HOA
Entry-Level
House for sale in Montego Bay
21736 SW 99th Ave, Cutler Bay, FL 33190
Listing Courtesy Of: Florida Capital Realty
Sold - Oct 21, 2024
Montego Bay, 9908 SW 218th Ter, Cutler Bay, Florida 33190, image 1
$710,000$49K
  • 4 Beds
  • 31/2 Baths
  • 1,888 SqFt
  • $376/SqFt
  • $127/mo HOA
Entry-Level
House for sale in Montego Bay
9908 SW 218th Ter, Cutler Bay, FL 33190
Listing Courtesy Of: RE/MAX Advance Realty II
Sold - Sep 26, 2024
Montego Bay, 21732 SW 99th Ave, Cutler Bay, Florida 33190, image 1
$440,000
  • 2 Beds
  • 2 Baths
  • 1,136 SqFt
  • $387/SqFt
  • $119/mo HOA
Entry-Level
House for sale in Montego Bay
21732 SW 99th Ave, Cutler Bay, FL 33190
Listing Courtesy Of: Keller Williams Capital Realty
Sold - Sep 25, 2024
Montego Bay, 22005 SW 100th Pl, Cutler Bay, Florida 33190, image 1
$480,000$50K
  • 3 Beds
  • 21/2 Baths
  • 1,650 SqFt
  • $291/SqFt
  • $157/mo HOA
Entry-Level
House for sale in Montego Bay
22005 SW 100th Pl, Cutler Bay, FL 33190
Listing Courtesy Of: Luxe Properties
Sold - Sep 13, 2024
Montego Bay, 21611 SW 98th Pl, Cutler Bay, Florida 33190, image 1
$470,000
  • 2 Beds
  • 2 Baths
  • 1,136 SqFt
  • $414/SqFt
  • $163/mo HOA
Entry-Level
House for sale in Montego Bay
21611 SW 98th Pl, Cutler Bay, FL 33190
Listing Courtesy Of: The Canero Group
Sold - Aug 27, 2024
Montego Bay, 10045 SW 218th St, Cutler Bay, Florida 33190, image 1
$485,000$65K
  • 3 Beds
  • 21/2 Baths
  • 1,650 SqFt
  • $294/SqFt
  • $157/mo HOA
Entry-Level
House for sale in Montego Bay
10045 SW 218th St, Cutler Bay, FL 33190
Listing Courtesy Of: EXP Realty LLC
Sold - Aug 19, 2024
Montego Bay, 21654 SW 98th Pl, Cutler Bay, Florida 33190, image 1
$500,000
  • 3 Beds
  • 2 Baths
  • 1,425 SqFt
  • $351/SqFt
  • $160/mo HOA
Entry-Level
House for sale in Montego Bay
21654 SW 98th Pl, Cutler Bay, FL 33190
Listing Courtesy Of: Pronto Realty LLC
Sold - May 28, 2024
Montego Bay, 9908 SW 218th Ter, Cutler Bay, Florida 33190, image 1
$450,000$25K
  • 4 Beds
  • 31/2 Baths
  • 1,888 SqFt
  • $238/SqFt
  • $127/mo HOA
Entry-Level
House for sale in Montego Bay
9908 SW 218th Ter, Cutler Bay, FL 33190
Listing Courtesy Of: RE/MAX Advance Realty II
Sold - Jan 26, 2024
Montego Bay, 22020 SW 100th Pl, Cutler Bay, Florida 33190, image 1
$545,000$5K
  • 4 Beds
  • 3 Baths
  • 1,925 SqFt
  • $283/SqFt
  • $100/mo HOA
Entry-Level
House for sale in Montego Bay
22020 SW 100th Pl, Cutler Bay, FL 33190
Listing Courtesy Of: Coldwell Banker Realty
Sold - Jan 24, 2024
Montego Bay, 10015 SW 218th St, Cutler Bay, Florida 33190, image 1
$510,000
  • 3 Beds
  • 2 Baths
  • 1,650 SqFt
  • $309/SqFt
  • $100/mo HOA
Entry-Level
House for sale in Montego Bay
10015 SW 218th St, Cutler Bay, FL 33190
Listing Courtesy Of: BZG International, LLC
Sold - Jan 5, 2024
Montego Bay, 9901 SW 218th Ter, Cutler Bay, Florida 33190, image 1
$525,000$5K
  • 3 Beds
  • 2 Baths
  • 1,425 SqFt
  • $368/SqFt
  • $132/mo HOA
Entry-Level
House for sale in Montego Bay
9901 SW 218th Ter, Cutler Bay, FL 33190
Listing Courtesy Of: The Keyes Company
Sold - Jan 4, 2024
Montego Bay, 9971 SW 218th Ter, Cutler Bay, Florida 33190, image 1
$515,000
  • 3 Beds
  • 2 Baths
  • 1,425 SqFt
  • $361/SqFt
  • $132/mo HOA
Entry-Level
House for sale in Montego Bay
9971 SW 218th Ter, Cutler Bay, FL 33190
Listing Courtesy Of: LoKation
Sold - Oct 23, 2023
Montego Bay, 21814 SW 98th Pl, Cutler Bay, Florida 33190, image 1
$434,500
  • 2 Beds
  • 2 Baths
  • 1,306 SqFt
  • $333/SqFt
  • $118/mo HOA
Entry-Level
House for sale in Montego Bay
21814 SW 98th Pl, Cutler Bay, FL 33190
Listing Courtesy Of: Redfin Corporation
1 - 29 of 102 Results

Subdivision Amenities

Clubhouse
Maintenance
Pool

HOA Cost Benchmark

$0.09 / Sq.Ft.

Monthly ownership cost
↑80%above peers
↓31%below city avg
This Community
$0.09
Comparable Premium Avg
$0.05
Cutler Bay, FL Avg
$0.13
$0.00
$0.08
$0.15
Higher than peers, lower than the city average
Peer Set · 9 comparable communities
See Cost Context

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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

Entry-Level
0.05 miles
Entry-Level
0.32 miles
Premium
0.32 miles
For Sale (1)
$695K - $695K
Premium
0.34 miles
Premium
0.36 miles
For Sale (3)
$490K - $520K
For Rent (2)
$3K - $3K

Schools

Scores

Walk Score®
Car-Dependent. Almost all errands require a car
15

100
Transit Score®
Some Transit. A few nearby public transportation options
33

100
Bike Score®
Bikeable. Some bike infrastructure
53

100
Sound Score®
Bearable noise
75

100
Airport Score
Close to airports. Noticeable airport activity
0

100
Traffic Score
Congested area. Frequent traffic delays
32

100
Local Score
Limited local amenities nearby
0

100

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