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

221 homes

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ABOUT THIS HOME
Vintage Home for sale in Monroe County, FL:
New Price, New Improvements, including new dock, deck off dock on jetty, boat lift, channel markers, dredging the channel, raise elevation of rocks on jetty and new landscaping! Entice Your Senses with Unobstructed Ocean Views in Lower Matecumbe! Welcome to this beautifully remodeled and inviting 3-bedroom, 2-bath concrete home offering panoramic Atlantic Ocean views right out your back door! Nestled on an expansive highway-to-oceanfront lot, this home showcases a comfortable open living floor plan, gorgeous kitchen, and a sparkling POOL surrounded by tropical landscaping—perfect for relaxing or entertaining. Step outside to enjoy 50' DOCKAGE and a large peninsula/jetty, ideal for imm

$4,425,000

3 beds2 baths1,331 sq ft

75691 Overseas Hwy, Islamorada, FL 33036

Spacious backyard • Great dockage • 1.01 acre lot

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Monroe County, FL:
Located in the heart of Key West's Historic District, 905 Grinnell Street is a distinctive multi-unit property that blends architectural character with strong investment performance. Originally built as a church, the structure has been thoughtfully converted into four residential units totaling 3,383 square feet. Each unit is individually metered and currently leased, offering a stable and reliable return. The property offers stable, predictable cash flow in one of Florida's most desirable markets, with a central location that places it within walking distance of local shops, dining, and attractions. Whether expanding your portfolio or seeking a turnkey income-producing property, 905 Grinne

$2,095,000

8 beds4 baths3,383 sq ft

905 Grinnell St, Key West, FL 33040

Individually metered • Central location • Historic charm

ABOUT THIS HOME
Vintage Home for sale in Monroe County, FL:
Unique opportunity for a creative buyer to own this 3 residential unit property. Would be a great for business owner looking for employee housing. Update all 3 homes for a family compound. Currently setup as roommate style living with a gross income of $15,000. a month. Don't miss this great location in Bahama Village steps from the Truman Waterfront, Ft. Zach beach, restaurants, galleries, shops and more!

$1,699,000

8 beds10 baths2,432 sq ft

720-726 Emma St, Key West, FL 33040

Ft zach beach • Bahama village • Truman waterfront

ABOUT THIS HOME
Vintage Home for sale in Monroe County, FL:
Welcome to this charming 1-bedroom, 1-bathroom apartment nestled in the heart of Key West. Located on desirable Seminary Street, this cozy yet functional home offers a perfect mix of comfort, character, and convenience. Step inside to find an open living space with hard flooring throughout the living room, office nook, and bedroom, complemented by easy-to-clean tile in the kitchen and bath. Natural light floods the interior through multiple windows and dual French doors that lead to a spacious private balcony — ideal for enjoying the tropical breeze. The thoughtfully designed layout includes a built-in desk and custom storage in the hallway, making great use of every inch of space. Th

$565,000

1 bed1 bath525 sq ft

1500 Seminary St Unit 5A, Key West, FL 33040

Custom storage • Private balcony • Hard flooring

ABOUT THIS HOME
Vintage Home for sale in Monroe County, FL:
Stunning Bayfront Opportunity with Western Sunset Views | Tavernier Positioned on Two 6,975 SqFt, Prime Waterfront Lots, with year-round western exposure, this one-of-a-kind Bayfront Property captures spectacular sunset views and offers a unique combination of existing income potential and future luxury development. Once a full duplex, the northside half has been professionally demolished and offers Approved Plans for a 3,300 SqFt, 3 BED/4 BATH, Three-Story Custom Residence! The architectural plans feature over 2,000 SqFt of covered Bayfront porches and an expansive rooftop deck, all designed to showcase the open water views and embrace the coastal lifestyle. The southside portion of the

$2,650,000

2 beds1 bath776 sq ft

190 & 192 Harborview Dr, Tavernier, FL 33070

Approved plans • Waterfront lots • Bayfront opportunity

Property at 230 Jolly Roger Dr, Key Largo, FL 33037, 3 beds, 2 baths

$1,425,000

3 beds2 baths1,736 sq ft

230 Jolly Roger Dr, Key Largo, FL 33037

(305) 809-8085

Property at 15 Seaside Ave, Key Largo, FL 33037, 3 beds, 3 baths

$749,000

3 beds3 baths1,800 sq ft

15 Seaside Ave, Key Largo, FL 33037

Property at 690 79th Street Ocean, Marathon, FL 33050, 2 beds, 2 baths

$699,000

2 beds2 baths1,446 sq ft

690 79th Street Ocean, Marathon, FL 33050

Property at 58704 Overseas Hwy, Marathon, FL 33050, 2 beds, 1 bath

$629,000

2 beds1 bath1,160 sq ft

58704 Overseas Hwy, Marathon, FL 33050

Property at 1124 Seminary St, Key West, FL 33040, 3 beds, 3.5 baths

$2,650,000

3 beds3.5 baths1,970 sq ft

1124 Seminary St, Key West, FL 33040

Property at 28 Tarpon Ave, Key Largo, FL 33037, 2 beds, 2 baths

$685,000

2 beds2 baths1,080 sq ft

28 Tarpon Ave, Key Largo, FL 33037

Property at 1704 Duncan St, Key West, FL 33040, 3 beds, 1 bath

$725,000

3 beds1 bath1,154 sq ft

1704 Duncan St, Key West, FL 33040

Property at 1151 Sugarloaf Blvd, Summerland Key, FL 33042, 3 beds, 2 baths

$1,689,000

3 beds2 baths2,144 sq ft

1151 Sugarloaf Blvd, Summerland Key, FL 33042

Property at 522 William St, Key West, FL 33040, 5 beds, 2 baths

$1,985,000

5 beds2 baths2,196 sq ft

522 William St, Key West, FL 33040

Property at 817 Eaton St #1, Key West, FL 33040, 1 bed, 1 bath

$850,000

1 bed1 bath740 sq ft

817 Eaton St #1, Key West, FL 33040

Property at 511 Tabby Ln, Key West, FL 33040, 3 beds, 1 bath

$1,900,000

3 beds1 bath1,368 sq ft

511 Tabby Ln, Key West, FL 33040

Property at 806 Southard St, Key West, FL 33040, 2 beds, 3 baths

$3,295,000

2 beds3 baths1,650 sq ft

806 Southard St, Key West, FL 33040

Property at 185 Gardenia St, Tavernier, FL 33070, 2 beds, 1 bath

$895,000

2 beds1 bath891 sq ft

185 Gardenia St, Tavernier, FL 33070

(267) 765-2080

Property at 11050 5Th Avenue Ocean, Marathon, FL 33050, 3 beds, 2 baths

$654,900

3 beds2 baths1,246 sq ft

11050 5Th Avenue Ocean, Marathon, FL 33050

Property at 75691-71 Overseas Hwy, Islamorada, FL 33036, 3 beds, 2 baths

$5,750,000

3 beds2 baths1,331 sq ft

75691-71 Overseas Hwy, Islamorada, FL 33036

Property at 719 Elizabeth St, Key West, FL 33040, 3 beds, 1 bath

$1,299,000

3 beds1 bath943 sq ft

719 Elizabeth St, Key West, FL 33040

Property at 2109 Seidenberg Ave, Key West, FL 33040, 4 beds, 3 baths

$1,250,000

4 beds3 baths1,554 sq ft

2109 Seidenberg Ave, Key West, FL 33040

Property at 2007 Flagler Ave, Key West, FL 33040, 6 beds, 5 baths

$1,275,000

6 beds5 baths2,102 sq ft

2007 Flagler Ave, Key West, FL 33040

Property at 1311 Grinnell St, Key West, FL 33040, 5 beds, 6 baths

$4,250,000

5 beds6 baths2,681 sq ft

1311 Grinnell St, Key West, FL 33040

Property at 2 Lime St, Key Largo, FL 33037

$1,900,000

— beds— baths5,198 sq ft

2 Lime St, Key Largo, FL 33037

Property at 1211 Catherine St, Key West, FL 33040, 3 beds, 2 baths

$1,680,000

3 beds2 baths1,463 sq ft

1211 Catherine St, Key West, FL 33040

Property at 1523 Patricia St, Key West, FL 33040, 4 beds, 3 baths

$4,650,000

4 beds3 baths3,154 sq ft

1523 Patricia St, Key West, FL 33040

Property at 80151 Overseas Hwy, Islamorada, FL 33036, 2 beds, 2 baths

$3,499,000

2 beds2 baths1,578 sq ft

80151 Overseas Hwy, Islamorada, FL 33036

Property at Undisclosed address, Key Largo, FL 33037, 1 bed, 1 bath

$495,000

1 bed1 bath480 sq ft

Undisclosed address, Key Largo, FL 33037

(305) 451-4078

Property at 1409 Truman Ave, Key West, FL 33040, 3 beds, 3.5 baths

$1,299,000

3 beds3.5 baths1,932 sq ft

1409 Truman Ave, Key West, FL 33040

Property at 13755 Overseas Hwy, Marathon, FL 33050, 4 beds, 4 baths

$1,800,000

4 beds4 baths3,017 sq ft

13755 Overseas Hwy, Marathon, FL 33050

Property at 901 Eisenhower Dr, Key West, FL 33040, 6 beds, 5 baths

$4,750,000

6 beds5 baths3,788 sq ft

901 Eisenhower Dr, Key West, FL 33040

Property at 508 Grinnell St, Key West, FL 33040, 3 beds, 3 baths

$2,800,000

3 beds3 baths2,049 sq ft

508 Grinnell St, Key West, FL 33040

Property at 625 73Rd Street Ocean St Unit A-B, Marathon, FL 33050, 4 beds, 3 baths

$595,000

4 beds3 baths1,203 sq ft

625 73Rd Street Ocean St Unit A-B, Marathon, FL 33050

Property at 1519 Johnson St, Key West, FL 33040, 5 beds, 4 baths

$2,290,000

5 beds4 baths2,366 sq ft

1519 Johnson St, Key West, FL 33040

Property at 11339 5Th Avenue Ocean, Marathon, FL 33050, 2 beds, 1 bath

$574,995

2 beds1 bath1,096 sq ft

11339 5Th Avenue Ocean, Marathon, FL 33050

Property at 1209 Truman Ave #2, Key West, FL 33040, 1 bed, 1.5 baths

$698,000

1 bed1.5 baths836 sq ft

1209 Truman Ave #2, Key West, FL 33040

Property at 21540 21470 Overseas Hwy, Summerland Key, FL 33042, 31 beds, 19 baths

$12,999,999

31 beds19 baths— sq ft

21540 21470 Overseas Hwy, Summerland Key, FL 33042

Property at 1703 South St, Key West, FL 33040, 3 beds, 2 baths

$1,749,000

3 beds2 baths1,785 sq ft

1703 South St, Key West, FL 33040

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

$2,795,000

4 beds3 baths1,931 sq ft

1501 Florida St, Key West, FL 33040

Property at 198 Lowe St, Tavernier, FL 33070, 5 beds, 4.5 baths

$8,490,000

5 beds4.5 baths4,170 sq ft

198 Lowe St, Tavernier, FL 33070

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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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