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

166 homes

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ABOUT THIS HOME
Vintage Home for sale in Monroe County, FL:
Classic Key West charm and sophistication abound, with traditional grace yet modern conveniences, this wasn't just a simple remodel. This was a carefully thought out, complete and careful renovation of this Old Town treasure. A worry free and easily maintained 3 bedroom, 2 and & ½ bath home, master bath ensuite, on one of the most prestigious streets in Key West, this home is constantly photographed, whether it's the location, the style, or the carefully chosen color pallet by the current owners, we're not sure, but regardless, many are drawn to this home and its beautifully tailored look. Whether you want to people watch on the front porch and sip your coffee or cocktail, or w

$3,180,000

3 beds2.5 baths1,373 sq ft

Complete renovation • Private back yard • Master bath ensuite

1019 Whitehead St, Key West, FL 33040

ABOUT THIS HOME
Vintage Home for sale in Monroe County, FL:
Fabulous Find on the Atlantic Side of Key West! Welcome to a truly unique opportunity in the heart of Key West. As the last and only remaining undeveloped property in the Historic Commercial Tourist District (HCT zone), this listing presents a rare and final chance to create something extraordinary. Imagine waking up to breathtaking, unobstructed ocean and beach views every day. Seabirds passing overhead, gentle breezes arriving at your lanai--it's an experience like nowhere else. This is island living at its finest! Permitted HCT uses include: Single-family and two-family residential dwellings, Multiple-family residential dwellings, Restaurant, Business and professional offices, Hotels, Mo

$9,888,000

3 beds2 baths2,071 sq ft

Hct zoning • 8,700 sq ft lot • Built 1953

1430 Vernon Ave, Key West, FL 33040

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Monroe County, FL:
Take this opportunity to own a beautifully updated home on nearly half an acre! Located in the peaceful highly desired neighborhood of Grassy Key. Minutes from the best restaurants, roof top bar, market and water park, it truly is an oasis.

$659,000

3 beds2 baths1,286 sq ft

Updated home • Half an acre • 0.34 acre lot

58110 Ferreire St, Grassy Key, FL 33050

ABOUT THIS HOME
Vintage Home for sale in Monroe County, FL:
Steeped in Key West history and unlike anything else available in Old Town, 511 Tabby Lane presents an opportunity to own one of the island's most extraordinary properties. Hidden away at the end of a charming pedestrian lane with direct access to iconic Duval Street, this remarkably private home offers a level of seclusion and potential that is virtually impossible to replicate. Rich in character and history, the property sits on an exceptionally deep 4,200-square-foot lot, a rarity in Old Town. There is simply no other property currently available that offers this combination of privacy, location, and land. The expansive lot provides endless possibilities, with ample space for a pool, poo

$1,800,000

3 beds1 bath1,368 sq ft

Gated entrance • 4,200 sq ft lot • Built 1913

511 Tabby Ln, Key West, FL 33040

ABOUT THIS HOME
Vintage Home for sale in Monroe County, FL:
TRANSIENT LICENCE RECEIVERSHIP ZONE! Welcome to your slice of paradise in Key West! This charming 2-bedroom, 2-bathroom condo located just steps from Duval Street offers an incredible opportunity. Currently utilized as an income-producing vacation rental, this home presents the perfect blend of comfort and convenience. Nestled in the heart of Key West, this condo boasts proximity to renowned attractions, vibrant restaurants, and the lively energy of Duval Street, ensuring endless entertainment options for residents and guests alike. Just a few blocks away lies Key West's South Beach, where sun-soaked days and breathtaking sunrises await. The interior of this inviting condo features two spac

$750,000

2 beds2 baths712 sq ft

Private balcony • $600 HOA • Built 1933

508 Louisa St #3, Key West, FL 33040

Property at 1511 17Th Ter, Key West, FL 33040, 3 beds, 3 baths

$2,499,000

3 beds3 baths2,502 sq ft

1511 17Th Ter, Key West, FL 33040

Property at 1019 Eaton St, Key West, FL 33040, 3 beds, 2 baths

$1,880,000

3 beds2 baths1,458 sq ft

1019 Eaton St, Key West, FL 33040

Property at 817 Terry Ln, Key West, FL 33040, 1 bed, 1 bath

$935,000

1 bed1 bath420 sq ft

817 Terry Ln, Key West, FL 33040

Property at 8 Poisonwood, Key Largo, FL 33037, 4 beds, 4 baths

$2,950,000

4 beds4 baths3,900 sq ft

8 Poisonwood, Key Largo, FL 33037

(305) 731-0060

Property at 203 Tarpon St, Tavernier, FL 33070, 3 beds, 2 baths

$845,000

3 beds2 baths1,372 sq ft

203 Tarpon St, Tavernier, FL 33070

Property at 60 Ed Swift Rd, Key West, FL 33040, 2 beds, 1 bath

$259,000

2 beds1 bath504 sq ft

60 Ed Swift Rd, Key West, FL 33040

Property at 813 2nd St, Key West, FL 33040, 3 beds, 2 baths

$1,000,000

3 beds2 baths895 sq ft

813 2nd St, Key West, FL 33040

Property at 1218 Packer St, Key West, FL 33040, 2 beds, 1 bath

$784,000

2 beds1 bath568 sq ft

1218 Packer St, Key West, FL 33040

Property at 615 Cuda Ln, Key Largo, FL 33037, 3 beds, 2 baths

$1,349,000

3 beds2 baths1,388 sq ft

615 Cuda Ln, Key Largo, FL 33037

Property at 574 & 576 99th Street Ocean, Marathon, FL 33050, 4 beds, 4 baths

$1,250,000

4 beds4 baths1,854 sq ft

574 & 576 99th Street Ocean, Marathon, FL 33050

Property at 3712 Duck Ave, Key West, FL 33040, 3 beds, 2.5 baths

$849,000

3 beds2.5 baths1,274 sq ft

3712 Duck Ave, Key West, FL 33040

Property at 800 Elizabeth St, Key West, FL 33040, 7 beds, 5 baths

$1,799,000

7 beds5 baths2,349 sq ft

800 Elizabeth St, Key West, FL 33040

Property at 1009 Whitehead St, Key West, FL 33040, 2 beds, 2 baths

$2,800,000

2 beds2 baths809 sq ft

1009 Whitehead St, Key West, FL 33040

Property at 416 Fleming St, Key West, FL 33040, 5 beds, 4.5 baths

$3,500,000

5 beds4.5 baths2,575 sq ft

416 Fleming St, Key West, FL 33040

Property at 3715 Flagler Ave, Key West, FL 33040, 2 beds, 2 baths

$799,000

2 beds2 baths1,216 sq ft

3715 Flagler Ave, Key West, FL 33040

Property at 818 Elizabeth St, Key West, FL 33040, 3 beds, 3 baths

$949,000

3 beds3 baths1,520 sq ft

818 Elizabeth St, Key West, FL 33040

Property at 1109 Stump Ln, Key West, FL 33040, 3 beds, 3 baths

$2,249,000

3 beds3 baths1,724 sq ft

1109 Stump Ln, Key West, FL 33040

Property at 8 Sadowski, Key Col Bch, FL 33051, 3 beds, 3 baths

$1,399,000

3 beds3 baths1,440 sq ft

8 Sadowski, Key Col Bch, FL 33051

Property at 815 Pearl St #2, Key West, FL 33040, 1 bed, 1 bath

$575,000

1 bed1 bath546 sq ft

815 Pearl St #2, Key West, FL 33040

Property at 60 Bird Ln, Key Largo, FL 33037, 3 beds, 2 baths

$579,900

3 beds2 baths910 sq ft

60 Bird Ln, Key Largo, FL 33037

Property at 30 Orange Dr, Key Largo, FL 33037, 1 bed, 1 bath

$494,900

1 bed1 bath722 sq ft

30 Orange Dr, Key Largo, FL 33037

Property at 118 1st Ct, Key Largo, FL 33037, 3 beds, 2 baths

$479,000

3 beds2 baths910 sq ft

118 1st Ct, Key Largo, FL 33037

Property at 1126 Grinnell St, Key West, FL 33040, 2 beds, 2 baths

$1,195,000

2 beds2 baths875 sq ft

1126 Grinnell St, Key West, FL 33040

Property at 846 Olivia St, Key West, FL 33040, 3 beds, 3 baths

$1,249,000

3 beds3 baths1,804 sq ft

846 Olivia St, Key West, FL 33040

Property at 1211 Knowles Ln, Key West, FL 33040, 3 beds, 2.5 baths

$1,475,000

3 beds2.5 baths1,284 sq ft

1211 Knowles Ln, Key West, FL 33040

Property at 1005 Watson St #1, Key West, FL 33040, 3 beds, 2 baths

$1,575,000

3 beds2 baths1,070 sq ft

1005 Watson St #1, Key West, FL 33040

Property at 901 Eisenhower Dr, Key West, FL 33040, 7 beds, 5 baths

$4,750,000

7 beds5 baths3,118 sq ft

901 Eisenhower Dr, Key West, FL 33040

Property at 1505 Johnson St, Key West, FL 33040, 3 beds, 3 baths

$1,474,000

3 beds3 baths1,489 sq ft

1505 Johnson St, Key West, FL 33040

Property at 2240 Yellowtail Dr, Marathon, FL 33050, 3 beds, 2 baths

$1,050,000

3 beds2 baths1,424 sq ft

2240 Yellowtail Dr, Marathon, FL 33050

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

$1,370,000

5 beds3 baths1,904 sq ft

11250 5Th Avenue Gulf Ave, Marathon, FL 33050

Property at 619 Ashe St, Key West, FL 33040, 3 beds, 3 baths

$3,800,000

3 beds3 baths1,933 sq ft

619 Ashe St, Key West, FL 33040

Property at 34 Atlantic Dr, Key Largo, FL 33037, 5 beds, 4 baths

$2,890,000

5 beds4 baths— sq ft

34 Atlantic Dr, Key Largo, FL 33037

(954) 545-5583

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

$2,999,999

4 beds3 baths1,863 sq ft

1501 White St, Key West, FL 33040

Property at 912 James St #2, Key West, FL 33040, 3 beds, 2.5 baths

$1,299,000

3 beds2.5 baths1,020 sq ft

912 James St #2, Key West, FL 33040

Property at 82891 Overseas Hwy, Islamorada, FL 33036, 3 beds, 3.5 baths

$2,100,000

3 beds3.5 baths2,036 sq ft

82891 Overseas Hwy, Islamorada, FL 33036

Property at 10833 2nd Avenue Gulf Ave, Marathon, FL 33050, 5 beds, 3 baths

$979,000

5 beds3 baths2,111 sq ft

10833 2nd Avenue Gulf Ave, Marathon, FL 33050

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Vintage Homes for Sale in Monroe County

There are currently 166 vintage homes for sale in Monroe County at a median listing price of $1.12M. 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 146 days. This map is refreshed with the newest listings in Monroe County every 15 minutes.

In the past month, 134 homes have been sold in Monroe County. In addition to houses in Monroe County, there were also 213 condos, 138 townhouses, and 65 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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