Vintage homes for sale & real estate in Cutler Bay, FL

40 homes

Sort:

Recommended

ABOUT THIS HOME
Vintage Home for sale in Cutler Bay, FL:
Quaint and well-maintained 3-Bedroom 2-Bath home just one block from beautiful Whispering Pines Lake. This charming residence features a newer roof, accordion shutters, and brand new vinyl flooring throughout most of the home, along with a newer A/C with brand new ducts. Enjoy a fenced-in, lushly landscaped private backyard with a screened-in patio, perfect for relaxing or entertaining. Additional highlights include a one-car garage and no association. Located nears parks, top schools, popular Black Point Marina, and minutes from Downtown Cutler Bay. Our community has many family events like golf cart parades, chili cook-offs, and much more. Make an offer and start enjoying South Florida li

$589,000

3 beds2 baths1,404 sq ft

19700 Whispering Pines Rd, Cutler Bay, FL 33157

Vinyl flooring • Newer roof • Accordion shutters

(305) 238-6453

ABOUT THIS HOME
Vintage Home for sale in Cutler Bay, FL:
Picture your family thriving in this beautifully renovated 5-bedroom, 2-bathroom home. Enjoy new impact windows, kitchen appliances, water heater, and air conditioning. The pool boasts new equipment and has been replastered. Featuring a 2016 shingle roof and a 2025 sealed flat roof. Situated on a corner lot, you have the added convenience of a quick walk or golf cart ride to Gulfstream Elementary, just two blocks away. This property was recently appraised for $655,000, providing instant equity.

$635,000

5 beds2 baths1,376 sq ft

9915 SW 212th St, Cutler Bay, FL 33189

New air conditioning • New water heater • New pool equipment

(305) 695-6300

ABOUT THIS HOME
Vintage Home for sale in Cutler Bay, FL:
This bright and spacious 4-bedroom, 2-bath home offers 2,000 SQFT of modern living with a flexible open floorplan filled with natural light. Enjoy peace of mind with a NEW roof, updated electrical, plumbing, and AC systems. Recently remodeled in 2025, the home features a NEW kitchen with sleek cabinets, a large island with quartz countertops, and stainless steel appliances. Additional upgrades include NEW oakwood vinyl plank flooring, LED lighting, NEW interior doors, moldings, and fresh paint inside & out. The fenced yard boasts fruit trees, a covered terrace, and ROOM FOR A POOL OR FUTURE EXPANSION. Accordion shutters, impact doors, and a covered carport add comfort and convenience.

$635,000

4 beds2 baths2,006 sq ft

Undisclosed address, Cutler Bay, FL 33157

Updated electrical • New kitchen • Updated ac systems

(786) 499-5497

ABOUT THIS HOME
Vintage Home for sale in Cutler Bay, FL:
Classic construction! This 1954 built 3 bedroom 2 bath single family home offers nearly 1600 square feet of living space, some actually original to the house! Buy and enjoy or update how you like. One car garage includes washer, dryer and water heater and plenty of space to store your fishing gear or toys. Large back yard features a huge concrete slab perfect for parking boats, trailers or RV's. Easy access to anywhere via nearby US1 and Florida Turnpike. No HOA so live your life hassle free! Newer roof so getting insurance will be no issue.

$575,000

3 beds2 baths1,741 sq ft

9750 Dominican Dr, Cutler Bay, FL 33189

Easy access • Huge concrete slab • Large back yard

(305) 235-3131

OPEN SAT, 11AM TO 2PM

ABOUT THIS HOME
Vintage Home for sale in Cutler Bay, FL:
Welcome to your dream home in Cutler Bay's sought-after Whispering Pines community! This home has had a new roof installed in 2021 & cast iron pipes replaced in 2024, ensuring peace of mind. Located just steps from the picturesque Whispering Pines Lake, embrace an active lifestyle with morning jogs along the scenic loop. Families will love the close proximity to Whispering Pines Elementary and the vibrant neighborhood events, including festive golf cart parades. Just 4.2 miles from Black Point Marina, enjoy easy access to Biscayne Bay. Inside, natural light enhances the open layout leading to a spacious screened patio - perfect for entertaining. Outside, find ample parking and a concr

$663,900

3 beds2 baths1,799 sq ft

8911 SW 197th St, Cutler Bay, FL 33157

Screened patio • Cast iron pipes • New roof

Property at 20130 SW 106th Ct, Cutler Bay, FL 33189, 3 beds, 2 baths

$714,500

3 beds2 baths1,502 sq ft

20130 SW 106th Ct, Cutler Bay, FL 33189

(786) 888-0198

Property at 9740 Cutler Ridge Dr, Cutler Bay, FL 33157, 4 beds, 2 baths

$689,000

4 beds2 baths2,002 sq ft

9740 Cutler Ridge Dr, Cutler Bay, FL 33157

(305) 298-2352

Property at 9851 Jamaica Dr, Cutler Bay, FL 33189, 3 beds, 2 baths

$750,000

3 beds2 baths1,742 sq ft

9851 Jamaica Dr, Cutler Bay, FL 33189

(305) 697-2904

Property at 9380 Caribbean Blvd, Cutler Bay, FL 33189, 5 beds, 2 baths

$675,000

5 beds2 baths1,972 sq ft

9380 Caribbean Blvd, Cutler Bay, FL 33189

(727) 596-1811

Property at 19550 Belview Dr, Cutler Bay, FL 33157, 4 beds, 2 baths

$650,000

4 beds2 baths1,876 sq ft

19550 Belview Dr, Cutler Bay, FL 33157

(305) 595-2844

Property at 9371 Martinique Dr, Cutler Bay, FL 33189, 4 beds, 3 baths

$699,000

4 beds3 baths1,612 sq ft

9371 Martinique Dr, Cutler Bay, FL 33189

(305) 229-1146

Property at 18690 Belview Dr, Cutler Bay, FL 33157, 4 beds, 2 baths

$600,000

4 beds2 baths2,036 sq ft

18690 Belview Dr, Cutler Bay, FL 33157

(786) 615-6761

Property at 20101 Ranch Rd, Cutler Bay, FL 33189, 3 beds, 2.5 baths

$720,000

3 beds2.5 baths1,650 sq ft

20101 Ranch Rd, Cutler Bay, FL 33189

Property at 10100 Nicaragua Dr, Cutler Bay, FL 33189, 3 beds, 2 baths

$679,000

3 beds2 baths1,174 sq ft

10100 Nicaragua Dr, Cutler Bay, FL 33189

(305) 595-2844

Property at 21310 Old Cutler Rd, Cutler Bay, FL 33189, 2 beds, 1 bath

$479,000

2 beds1 bath1,259 sq ft

21310 Old Cutler Rd, Cutler Bay, FL 33189

(305) 809-8085

Property at 18710 Belmont Dr, Cutler Bay, FL 33157, 4 beds, 2 baths

$599,000

4 beds2 baths1,896 sq ft

18710 Belmont Dr, Cutler Bay, FL 33157

(305) 238-6453

Property at 19341 Holiday Rd, Cutler Bay, FL 33157, 4 beds, 3 baths

$670,000

4 beds3 baths2,133 sq ft

19341 Holiday Rd, Cutler Bay, FL 33157

(305) 251-2127

Property at 9400 Caribbean Blvd, Cutler Bay, FL 33189, 4 beds, 2 baths

$700,000

4 beds2 baths1,720 sq ft

9400 Caribbean Blvd, Cutler Bay, FL 33189

(305) 251-4044

Property at 8950 SW 197th St, Cutler Bay, FL 33157, 4 beds, 2 baths

$750,000

4 beds2 baths2,490 sq ft

8950 SW 197th St, Cutler Bay, FL 33157

(305) 229-1146

Property at 10250 Caribbean Blvd, Cutler Bay, FL 33189, 4 beds, 2 baths

$540,000

4 beds2 baths1,429 sq ft

10250 Caribbean Blvd, Cutler Bay, FL 33189

(305) 595-2844

Property at 8821 SW 192nd St, Cutler Bay, FL 33157, 3 beds, 2 baths

$775,000

3 beds2 baths1,755 sq ft

8821 SW 192nd St, Cutler Bay, FL 33157

(305) 514-0100

Property at 10241 Dominican Dr, Cutler Bay, FL 33189, 3 beds, 2 baths

$605,000

3 beds2 baths1,469 sq ft

10241 Dominican Dr, Cutler Bay, FL 33189

(305) 809-7650

Property at 19201 Flag Dr, Cutler Bay, FL 33157, 4 beds, 2 baths

$669,900

4 beds2 baths1,834 sq ft

19201 Flag Dr, Cutler Bay, FL 33157

(305) 333-0741

Property at 9880 Jamaica Dr, Cutler Bay, FL 33189, 4 beds, 2 baths

$569,900

4 beds2 baths1,487 sq ft

9880 Jamaica Dr, Cutler Bay, FL 33189

(305) 809-7650

Property at 9021 SW 197th St, Cutler Bay, FL 33157, 3 beds, 2 baths

$689,000

3 beds2 baths1,404 sq ft

9021 SW 197th St, Cutler Bay, FL 33157

(305) 514-0100

Property at 10020 Dominican Dr, Cutler Bay, FL 33189, 2 beds, 2 baths

$499,900

2 beds2 baths868 sq ft

10020 Dominican Dr, Cutler Bay, FL 33189

(786) 536-9423

Property at 9620 Jamaica Dr, Cutler Bay, FL 33189, 4 beds, 2 baths

$640,000

4 beds2 baths1,344 sq ft

9620 Jamaica Dr, Cutler Bay, FL 33189

(877) 661-1977

Property at 9340 Martinique Dr, Cutler Bay, FL 33189, 3 beds, 2 baths

$629,000

3 beds2 baths1,504 sq ft

9340 Martinique Dr, Cutler Bay, FL 33189

(305) 253-2800

Property at 19711 Whispering Pines Rd, Cutler Bay, FL 33157, 5 beds, 2 baths

$715,000

5 beds2 baths2,130 sq ft

19711 Whispering Pines Rd, Cutler Bay, FL 33157

(305) 238-6453

Property at 9281 Martinique Dr, Cutler Bay, FL 33189, 5 beds, 2 baths

$579,900

5 beds2 baths1,712 sq ft

9281 Martinique Dr, Cutler Bay, FL 33189

Property at 19310 Christmas Rd, Cutler Bay, FL 33157, 3 beds, 1 bath

$550,000

3 beds1 bath1,125 sq ft

19310 Christmas Rd, Cutler Bay, FL 33157

(855) 450-0442

Property at 8720 SW 192nd Ter, Cutler Bay, FL 33157, 4 beds, 3 baths

$750,000

4 beds3 baths2,319 sq ft

8720 SW 192nd Ter, Cutler Bay, FL 33157

(305) 282-6940

Property at 18601 SW 98th Ave, Cutler Bay, FL 33157, 4 beds, 3 baths

$699,000

4 beds3 baths2,176 sq ft

18601 SW 98th Ave, Cutler Bay, FL 33157

(305) 644-8880

Property at 8000 SW 184th St, Cutler Bay, FL 33157, 3 beds, 1.5 baths

$3,000,000

3 beds1.5 baths1,709 sq ft

8000 SW 184th St, Cutler Bay, FL 33157

(305) 662-7325

Property at 10120 Nicaragua Dr, Cutler Bay, FL 33189, 4 beds, 2 baths

$749,000

4 beds2 baths1,800 sq ft

10120 Nicaragua Dr, Cutler Bay, FL 33189

(866) 595-6025

Property at 8711 SW 191st St, Cutler Bay, FL 33157, 3 beds, 2 baths

$715,000

3 beds2 baths1,297 sq ft

8711 SW 191st St, Cutler Bay, FL 33157

(239) 318-4689

Property at 9370 Martinique Dr, Cutler Bay, FL 33189, 3 beds, 2 baths

$799,000

3 beds2 baths1,248 sq ft

9370 Martinique Dr, Cutler Bay, FL 33189

(786) 512-4371

Property at 9365 Jamaica Dr, Cutler Bay, FL 33189, 3 beds, 2 baths

$639,900

3 beds2 baths1,928 sq ft

9365 Jamaica Dr, Cutler Bay, FL 33189

(786) 250-4270

Property at 9761 Bahama Dr, Cutler Bay, FL 33189, 3 beds, 2 baths

$690,000

3 beds2 baths1,395 sq ft

9761 Bahama Dr, Cutler Bay, FL 33189

(305) 726-3651

Property at 18800 Lenaire Dr, Cutler Bay, FL 33157, 4 beds, 4 baths

$765,000

4 beds4 baths1,773 sq ft

18800 Lenaire Dr, Cutler Bay, FL 33157

(786) 447-3600

Viewing page 1 of 1

Vintage Homes for Sale in Cutler Bay

There are currently 40 vintage homes for sale in Cutler Bay at a median listing price of $615K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Cutler Bay stay on the market for 89 days and receive 1 offers. Popular neighborhoods include Cutler Ridge, Bel Aire, Whispering Pines Estates, Cutler Cay, and Saga Bay. This map is refreshed with the newest listings in Cutler Bay every 15 minutes.

In the past month, 42 homes have been sold in Cutler Bay. In addition to houses in Cutler Bay, there were also 46 condos, 47 townhouses, and 2 multi-family units for sale in Cutler Bay last month. Cutler Bay is a minimally walkable city in Miami-Dade County with a Walk Score of 27. Cutler Bay is home to approximately 40,397 people and 7,132 jobs. Find your dream home in Cutler Bay using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Cutler Bay are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Cutler Bay. Our Cutler Bay real estate stats and trends will give you more information about home buying and selling trends in Cutler Bay. If you're looking to sell your home in the Cutler Bay area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Cutler Bay with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

More real estate resources for Cutler Bay, FL

Neighborhoods

Zip Codes

Nearby Cities

Nearby Cities with Vintage Homes

Nearby Neighborhoods with Vintage Homes

More to explore in Cutler Bay, FL

How to buy a house in Cutler Bay, FL

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Popular Markets in Florida

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Why Redfin?

Community Impact

Diversity & Inclusion

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.