Vintage homes for sale & real estate in Monroe County, FL

221 homes

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3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Monroe County, FL:
Situated along one of Old Town's most storied corridors, residence #6 at 616 Caroline Street offers a refined Keys lifestyle just steps from the Historic Seaport, Duval Street dining, galleries, and marinas. Tucked within a boutique setting, this private upstairs home balances character and comfort with a bright, welcoming living area and an efficient layout that makes everyday living—and easy lock-and-leave ownership—simple. Offered turnkey, the residence conveys fully furnished, allowing you to settle in immediately and enjoy the space from day one. The kitchen and downstairs bath are thoughtfully arranged to maximize storage and function, while the ensuite bedroom retreat pro

$799,000

1 bed2 baths650 sq ft

616 Caroline St #6, Key West, FL 33040

Efficient layout • Historic seaport • Turnkey

ABOUT THIS HOME
Vintage Home for sale in Monroe County, FL:
STUNNING OPEN CONCEPT 2 BEDROOM -1 BATH BEING OFFERED FURNISHED OR UNFURNISHED! NO HOA OR CONDO FEES!! Dock your boat in your own Deep Water Dockage that can accommodate a 40+ foot Plus Vessel! Direct Ocean Access in less than 5 minutes with No Bridges. Spectacular bone-fish bay Water Views! Large master bedroom with King Size bed accompanied by a large dresser nightstand tables and a 75 inch smart TV. Second bedroom equipped with top and bottom full-size bunk beds and a pull out twin size bed. Freshly updated Interior and new stucco/painted exterior. All New gutters. All Hurricane Impact windows and doors. Renovated Kitchen, Quartz Counter Tops, huge 4x8 foot island. All New Stainless Stee

$769,000

2 beds1 bath960 sq ft

5 Sadowski, Key Col Bch, FL 33051

Deep water dockage • Renovated kitchen • Quartz counter tops

ABOUT THIS HOME
Vintage Home for sale in Monroe County, FL:
Transient receiver site - Truly a diamond in the rough. Great location, behind the Hemingway House between Duval and Whitehead Street. Lot backs up to Whalton Lane (off Duval) with room for parking and a pool. Bring your contractor and a transient license to the property and she will truly shine like the Hope Diamond with happiness and prosperity. Buyers should do their own due diligence to determine transient license receivership requirements prior to making an offer. Probate is required.

$1,200,000

3 beds1 bath920 sq ft

418 Olivia St, Key West, FL 33040

Room for a pool • Room for parking • 3,034 sq ft lot

ABOUT THIS HOME
Vintage Home for sale in Monroe County, FL:
AUCTION. This affordable gem offers 3 beds, 2 baths, an attached carport and covered porch. Home is in close proximity to beaches, dining, and shops—walk or bike everywhere. Don't miss your opportunity to experience this Old Key West gem. Property is sold as-is with NO interior photos, NO lease in place, NO property disclosure or inspection report, NO ACCESS - - the seller does not represent or guarantee occupancy status. Please DO NOT DISTURB the occupant. "As is" CASH ONLY sale with no contingencies or inspections. Buyer will be responsible for obtaining possession of the property upon closing.

$903,800

3 beds2 baths1,760 sq ft

1019 Packer St, Key West, FL 33040

2,439 sq ft lot • 2 parking spots • Built 1933

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Monroe County, FL:
Motivated seller — Quick Close! Welcome to 908 Catherine Street - a delightful blend of historic charm and modern comfort tucked in the heart of Old Town Key West. This beautifully renovated home boasts 3 bedrooms and 3.5 baths, offering a rare opportunity to enjoy relaxed island living in the coveted ''X'' flood zone of Key West. Step inside and you'll find original Dade County pine cathedral ceilings with exposed beams and warm oak flooring that echo classic Keys style. The interiors are anchored by calming, neutral palettes and finished with high-end elements like Calcutta marble baths, quartz countertops, crown molding, and Bosch appliances. Every system has been thoughtfully upda

$1,799,900

3 beds3.5 baths1,572 sq ft

908 Catherine St, Key West, FL 33040

Oak flooring • Exposed beams • High and dry lot

Property at 2809 Flagler Ave, Key West, FL 33040, 4 beds, 2 baths

$1,199,000

4 beds2 baths2,274 sq ft

2809 Flagler Ave, Key West, FL 33040

Property at 1824 Fogarty Ave, Key West, FL 33040, 6 beds, 7 baths

$1,400,000

6 beds7 baths1,306 sq ft

1824 Fogarty Ave, Key West, FL 33040

Property at 1706 Seminary St, Key West, FL 33040, 3 beds, 3 baths

$2,249,000

3 beds3 baths1,938 sq ft

1706 Seminary St, Key West, FL 33040

Property at 2119 Flagler Ave, Key West, FL 33040, 2 beds, 2 baths

$789,000

2 beds2 baths1,030 sq ft

2119 Flagler Ave, Key West, FL 33040

Property at 1018 Georgia St, Key West, FL 33040, 3 beds, 2 baths

$1,150,000

3 beds2 baths1,452 sq ft

1018 Georgia St, Key West, FL 33040

Property at 1022 Fleming St, Key West, FL 33040, 4 beds, 2 baths

$1,999,990

4 beds2 baths2,016 sq ft

1022 Fleming St, Key West, FL 33040

Property at 1320 Eliza St, Key West, FL 33040, 4 beds, 3 baths

$2,599,000

4 beds3 baths1,854 sq ft

1320 Eliza St, Key West, FL 33040

Property at 129 Pirates Dr, Key Largo, FL 33037, 2 beds, 2 baths

$1,199,000

2 beds2 baths1,315 sq ft

129 Pirates Dr, Key Largo, FL 33037

(954) 545-5583

Property at 1719 Laird St, Key West, FL 33040, 4 beds, 3 baths

$2,188,000

4 beds3 baths2,276 sq ft

1719 Laird St, Key West, FL 33040

Property at 705 Chapman Ln, Key West, FL 33040, 3 beds, 1 bath

$1,350,000

3 beds1 bath1,231 sq ft

705 Chapman Ln, Key West, FL 33040

Property at 91865 Overseas Hwy #107, Tavernier, FL 33070, 1 bath

$1,850

0 beds1 bath400 sq ft

91865 Overseas Hwy #107, Tavernier, FL 33070

Property at 2211 Staples Ave, Key West, FL 33040, 4 beds, 3.5 baths

$1,499,000

4 beds3.5 baths1,912 sq ft

2211 Staples Ave, Key West, FL 33040

Property at 1830 Fogarty Ave #4, Key West, FL 33040, 1 bed, 1 bath

$485,000

1 bed1 bath388 sq ft

1830 Fogarty Ave #4, Key West, FL 33040

Property at 1916 Seidenberg Ave, Key West, FL 33040, 6 beds, 2 baths

$1,068,000

6 beds2 baths1,694 sq ft

1916 Seidenberg Ave, Key West, FL 33040

Property at 1231 Washington St, Key West, FL 33040, 3 beds, 3.5 baths

$2,550,000

3 beds3.5 baths1,818 sq ft

1231 Washington St, Key West, FL 33040

Property at 1420 White St, Key West, FL 33040, 5 beds, 3 baths

$3,299,000

5 beds3 baths2,608 sq ft

1420 White St, Key West, FL 33040

Property at 1118 Eaton St, Key West, FL 33040, 3 beds, 2.5 baths

$1,199,000

3 beds2.5 baths1,300 sq ft

1118 Eaton St, Key West, FL 33040

Property at 709 Chapman Ln, Key West, FL 33040, 2 beds, 1.5 baths

$1,249,000

2 beds1.5 baths1,109 sq ft

709 Chapman Ln, Key West, FL 33040

Property at 1006-1008 Fleming St, Key West, FL 33040, 4 beds, 4.5 baths

$5,595,000

4 beds4.5 baths3,336 sq ft

1006-1008 Fleming St, Key West, FL 33040

Property at 11250 5Th Avenue Gulf Ave, Marathon, FL 33050, 5 beds, 3 baths

$1,291,000

5 beds3 baths1,904 sq ft

11250 5Th Avenue Gulf Ave, Marathon, FL 33050

Property at 140 Tavern Dr, Tavernier, FL 33070, 1 bed, 1 bath

$525,000

1 bed1 bath506 sq ft

140 Tavern Dr, Tavernier, FL 33070

Property at 2800 Staples Ave, Key West, FL 33040, 4 beds, 3.5 baths

$1,649,000

4 beds3.5 baths2,058 sq ft

2800 Staples Ave, Key West, FL 33040

Property at 1501 White St, Key West, FL 33040, 4 beds, 3 baths

$3,399,000

4 beds3 baths1,734 sq ft

1501 White St, Key West, FL 33040

Property at 1014 Truman Ave #3, Key West, FL 33040, 2 beds, 2 baths

$799,900

2 beds2 baths1,017 sq ft

1014 Truman Ave #3, Key West, FL 33040

Property at 1625 Patricia St, Key West, FL 33040, 3 beds, 2.5 baths

$2,050,000

3 beds2.5 baths1,839 sq ft

1625 Patricia St, Key West, FL 33040

Property at 422 Amelia St Unit L6, Key West, FL 33040, 1 bed, 1 bath

$1,475,000

1 bed1 bath405 sq ft

422 Amelia St Unit L6, Key West, FL 33040

Property at 1606 Flagler Ave, Key West, FL 33040, 2 beds, 2 baths

$1,035,000

2 beds2 baths1,118 sq ft

1606 Flagler Ave, Key West, FL 33040

Property at 31525 Avenue A, Big Pine Key, FL 33043, 3 beds, 2 baths

$525,000

3 beds2 baths1,278 sq ft

31525 Avenue A, Big Pine Key, FL 33043

Property at 1612 Washington St, Key West, FL 33040, 4 beds, 2 baths

$1,575,000

4 beds2 baths1,760 sq ft

1612 Washington St, Key West, FL 33040

Property at 915 Washington St, Key West, FL 33040, 2 beds, 2 baths

$1,795,000

2 beds2 baths1,193 sq ft

915 Washington St, Key West, FL 33040

Property at 644 26Th Street Ocean, Marathon, FL 33050, 2 beds, 2 baths

$775,000

2 beds2 baths1,293 sq ft

644 26Th Street Ocean, Marathon, FL 33050

Property at 251 Azalea St, Tavernier, FL 33070, 2 beds, 2 baths

$1,495,000

2 beds2 baths1,279 sq ft

251 Azalea St, Tavernier, FL 33070

Property at 963 69th Street Ocean, Marathon, FL 33050, 3 beds, 2 baths

$599,000

3 beds2 baths1,345 sq ft

963 69th Street Ocean, Marathon, FL 33050

Property at 11401 1st Ave, Marathon, FL 33050, 2 beds, 1 bath

$435,000

2 beds1 bath875 sq ft

11401 1st Ave, Marathon, FL 33050

Property at 1718 United St, Key West, FL 33040, 3 beds, 2.5 baths

$1,449,000

3 beds2.5 baths1,477 sq ft

1718 United St, Key West, FL 33040

Property at 2827 Staples Ave, Key West, FL 33040, 4 beds, 2 baths

$1,400,000

4 beds2 baths1,741 sq ft

2827 Staples Ave, Key West, FL 33040

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Based on information submitted to the MLS GRID as of Mon Dec 01 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Vintage Homes for Sale in Monroe County

There are currently 221 vintage homes for sale in Monroe County at a median listing price of $1.2M. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Monroe County stay on the market for 151 days. This map is refreshed with the newest listings in Monroe County every 15 minutes.

In the past month, 135 homes have been sold in Monroe County. In addition to houses in Monroe County, there were also 255 condos, 145 townhouses, and 57 multi-family units for sale in Monroe County last month. Find your dream home in Monroe County 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 Monroe County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Monroe County. If you're looking to sell your home in the Monroe County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Monroe County with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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