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

221 homes

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NEW 28 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Monroe County, FL:
Your Private Slice of Key Largo Paradise Awaits! Escape to a quiet coastal retreat designed for relaxation and adventure. This beautifully updated concrete 1-bedroom, 1-bath home is situated on a corner lot in the heart of Key Largo is just steps from the water and beckons you to embrace the island lifestyle. This is like living on the water without paying the premium price. Bonus: 2 kayaks and bicycles are included. Imagine waking up and using your own two kayaks to explore the Bay or easily launching your boat from the neighborhood ramp right across the street. Boating enthusiasts will love the easy access to the ocean via Adams Cut or Tavernier Creek. Evenings are for unwinding in the ou

$519,900

1 bed1 bath561 sq ft

40 Pirates Dr, Key Largo, FL 33037

Paved patio • Outdoor hot tub • Corner lot

ABOUT THIS HOME
Vintage Home for sale in Monroe County, FL:
Stunning property in Little Venice, fully furnished and located in the heart of the Florida Keys. This 2BD/2BA home, with an additional extra room, is ready for you to make your own piece of paradise! Enjoy an oversized living and dining area for entertaining, complete with plank tile flooring throughout. Both bathrooms feature stylish accented subway tile and matching modern fixtures. The kitchen offers a pass-through bar, sleek stainless-steel appliances, shaker cabinets with under cabinet lighting, and beautiful quartz countertops. The exterior includes accordion shutters and a 5V crimp metal roof. Paved parking provides plenty of room for a boat on this corner lot. Just minutes from Som

$609,000

2 beds2 baths1,220 sq ft

11405 3Rd Avenue Ocean, Marathon, FL 33050

Pass-through bar • Shaker cabinets • Plank tile flooring

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Monroe County, FL:
Gorgeous CONCH home in the ultimate Old Town location - only one block from Duval, in a neighborhood lined with historic homes! Live in the heart of Old Town where charming architecture, iconic streetscapes, and Key West's finest restaurants and shops are right outside your door. This beautifully restored 1889 Conch home has been completely renovated in 2022 to the studs, blending historic character with sophisticated modern upgrades. Currently configured as a single family home, open-concept living area, 10 ft ceilings and restored Dade County Pine throughout. The great room flows into the chef's kitchen featuring high-end Café appliances, gas range, and custom cast-in-place concret

$2,975,000

4 beds3 baths1,800 sq ft

529 Simonton St, Key West, FL 33040

Private porch • Bespoke bar • Old town location

ABOUT THIS HOME
Vintage Home for sale in Monroe County, FL:
Wake up in paradise every day. This waterfront retreat in Marathon Key offers instant ocean access, unforgettable sunsets, and a laid-back coastal lifestyle. Fully renovated and beautifully furnished, every space feels like vacation. Enjoy boating, fishing, and dining al fresco on your private waterfront patio with summer kitchen. With zoning allowing daily rentals, this is both the perfect escape and a high-income opportunity. Your piece of the Florida Keys is here -- just bring your boat and your dreams.

$1,200,000

2 beds2 baths1,056 sq ft

798 96th Street Ocean St, Marathon, FL 33050

Summer kitchen • Waterfront retreat • Instant ocean access

ABOUT THIS HOME
Vintage Home for sale in Monroe County, FL:
Close to the Historic Seaport, restaurants, art galleries, and more!. Recently renovated, this 2 bedroom, 1 bath condo has high impact windows and door, washer/ dryer, tankless hot water heater, new flooring, kitchen, mini splits, appliances, and is being sold furnished! Prime Old Town location, walk or bike to everything! This is easy island living- close to everything, and no need for a car.

$675,000

2 beds1 bath643 sq ft

409 Margaret St #202, Key West, FL 33040

New flooring • High impact windows • $755 HOA

Property at 804 South St #1, Key West, FL 33040, 1 bed, 1 bath

$640,000

1 bed1 bath640 sq ft

804 South St #1, Key West, FL 33040

Property at 1020 Fleming St, Key West, FL 33040, 2 beds, 1 bath

$1,442,100

2 beds1 bath759 sq ft

1020 Fleming St, Key West, FL 33040

Property at 11725 3rd Avenue Ocean, Marathon, FL 33050, 2 beds, 2 baths

$960,000

2 beds2 baths900 sq ft

11725 3rd Avenue Ocean, Marathon, FL 33050

Property at 421 United St, Key West, FL 33040, 3 beds, 2.5 baths

$2,100,000

3 beds2.5 baths2,205 sq ft

421 United St, Key West, FL 33040

Property at 625 Whitehead St, Key West, FL 33040, 4 beds, 2 baths

$1,345,000

4 beds2 baths1,660 sq ft

625 Whitehead St, Key West, FL 33040

Property at 799 28Th Street Ocean, Marathon, FL 33050, 3 beds, 2 baths

$1,300,000

3 beds2 baths1,189 sq ft

799 28Th Street Ocean, Marathon, FL 33050

Property at 732 Olivia St, Key West, FL 33040, 1 bed, 1 bath

$825,000

1 bed1 bath510 sq ft

732 Olivia St, Key West, FL 33040

Property at 409 Grinnell St, Key West, FL 33040, 4 beds, 2 baths

$2,499,000

4 beds2 baths1,628 sq ft

409 Grinnell St, Key West, FL 33040

Property at 703 Elizabeth St, Key West, FL 33040, 3 beds, 2 baths

$2,299,000

3 beds2 baths1,404 sq ft

703 Elizabeth St, Key West, FL 33040

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

$1,100,000

1 bed1 bath420 sq ft

817 Terry Ln, Key West, FL 33040

Property at 16750 Old State Road 4A, Summerland Key, FL 33042, 6 beds, 4.5 baths

$9,950,000

6 beds4.5 baths5,208 sq ft

16750 Old State Road 4A, Summerland Key, FL 33042

Property at 524 Southard St, Key West, FL 33040, 3 beds, 3 baths

$3,300,000

3 beds3 baths2,262 sq ft

524 Southard St, Key West, FL 33040

Property at 411 Louisa St, Key West, FL 33040, 5 beds, 4.5 baths

$6,750,000

5 beds4.5 baths3,663 sq ft

411 Louisa St, Key West, FL 33040

Property at 543 74Th St, Marathon, FL 33050, 2 beds, 1 bath

$649,000

2 beds1 bath672 sq ft

543 74Th St, Marathon, FL 33050

Property at 600 Whitehead St #203, Key West, FL 33040, 1 bed

$499,900

1 bed— baths308 sq ft

600 Whitehead St #203, Key West, FL 33040

Property at 119 Poinciana Dr, Key Largo, FL 33037, 3 beds, 1 bath

$605,000

3 beds1 bath1,000 sq ft

119 Poinciana Dr, Key Largo, FL 33037

(305) 247-7221

Property at 1014 Southard St, Key West, FL 33040, 4 beds, 3.5 baths

$4,995,000

4 beds3.5 baths3,026 sq ft

1014 Southard St, Key West, FL 33040

Property at 7501 Gulfstream Blvd, Marathon, FL 33050, 3 beds, 3 baths

$1,825,000

3 beds3 baths2,405 sq ft

7501 Gulfstream Blvd, Marathon, FL 33050

Property at 103 Front St, Key West, FL 33040, 3 beds, 3 baths

$6,850,000

3 beds3 baths4,200 sq ft

103 Front St, Key West, FL 33040

Property at 103 Tree Ln, Tavernier, FL 33070, 2 beds, 2.5 baths

$406,125

2 beds2.5 baths795 sq ft

103 Tree Ln, Tavernier, FL 33070

(305) 451-4422

Property at 140 Gumbo Limbo Dr, Key Largo, FL 33037, 1 bed, 1 bath

$495,000

1 bed1 bath620 sq ft

140 Gumbo Limbo Dr, Key Largo, FL 33037

Property at 1116 Elgin Ln, Key West, FL 33040, 3 beds, 2 baths

$2,299,000

3 beds2 baths1,516 sq ft

1116 Elgin Ln, Key West, FL 33040

Property at 357 23rd St, Marathon, FL 33050, 2 beds, 1 bath

$589,000

2 beds1 bath1,010 sq ft

357 23rd St, Marathon, FL 33050

Property at 1925 Fogarty Ave, Key West, FL 33040, 5 beds, 3.5 baths

$979,000

5 beds3.5 baths1,634 sq ft

1925 Fogarty Ave, Key West, FL 33040

Property at 919-921 Thomas St, Key West, FL 33040, 7 beds, 7.5 baths

$3,995,000

7 beds7.5 baths3,015 sq ft

919-921 Thomas St, Key West, FL 33040

Property at 715 65Th Street Ocean, Marathon, FL 33050, 4 beds, 3 baths

$830,000

4 beds3 baths2,158 sq ft

715 65Th Street Ocean, Marathon, FL 33050

Property at 2105 Fogarty Ave, Key West, FL 33040, 4 beds, 3 baths

$1,495,000

4 beds3 baths1,578 sq ft

2105 Fogarty Ave, Key West, FL 33040

Property at 1510 18Th St, Key West, FL 33040, 3 beds, 2 baths

$1,199,999

3 beds2 baths1,714 sq ft

1510 18Th St, Key West, FL 33040

Property at 11554 5th Avenue Ocean, Marathon, FL 33050, 3 beds, 2 baths

$730,000

3 beds2 baths1,222 sq ft

11554 5th Avenue Ocean, Marathon, FL 33050

(305) 598-5488

Property at 1115 Varela St, Key West, FL 33040, 3 beds, 2 baths

$799,000

3 beds2 baths1,292 sq ft

1115 Varela St, Key West, FL 33040

Property at 626 Margaret St, Key West, FL 33040, 3 beds, 1.5 baths

$1,649,000

3 beds1.5 baths1,392 sq ft

626 Margaret St, Key West, FL 33040

Property at 1527 Von Phister St, Key West, FL 33040, 4 beds, 3 baths

$1,449,000

4 beds3 baths1,767 sq ft

1527 Von Phister St, Key West, FL 33040

Property at 728 Largo Rd, Key Largo, FL 33037, 2 beds, 2 baths

$239,000

2 beds2 baths624 sq ft

728 Largo Rd, Key Largo, FL 33037

Property at 627 Caroline St, Key West, FL 33040, 5 beds, 5.5 baths

$5,000,000

5 beds5.5 baths2,230 sq ft

627 Caroline St, Key West, FL 33040

Property at 132 E Gardenia St, Tavernier, FL 33070, 3 beds, 3 baths

$1,250,000

3 beds3 baths1,360 sq ft

132 E Gardenia St, Tavernier, FL 33070

(239) 776-5194

Property at 50 7Th Ave, Key Colony, FL 33051, 3 beds, 3 baths

$1,589,000

3 beds3 baths1,605 sq ft

50 7Th Ave, Key Colony, FL 33051

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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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