Monroe County, FL Homes

/41
$875,000
- 2 Beds
- 2 Baths
- 1,176 Sq Ft
1901 S Roosevelt Blvd Unit 104, Key West, FL 33040

Coastal Living at Its Finest - 2-Bedroom Condo at La Brisa ! Wake up to ocean breezes in this beautifully appointed 2-bedroom, 2-bathroom condo located just steps from Smathers beach. Situated directly across the street from the shoreline, this bright and airy residence offers the perfect blend of comfort, convenience, and coastal charm. Inside, you'll find a spacious open-concept living and

Terrance Sullivan

Ocean Sotheby's International Realty

(786) 982-8761

1901 S Roosevelt Blvd Unit 104, Key West, FL 33040
/16
$3,900 per month
- 3 Beds
- 2 Baths
- 1,722 Sq Ft
- Condo for Rent
164 Ocean Bay Dr Unit 3-C, Key Largo, FL 33037

Gorgeous Key Largo Townhome centrally located with ocean access. Enjoy your wonderful place of retreat, relaxation, tennis, swimming and breathtaking nature. Walking distance from great dining and shopping. Come and create Wonderful memories and enjoy the Key Largo Experience! Stunning Ocean/Sunset view from private balcony condo. Gorgeous Key Largo Townhome centrally located with ocean access.

Shannon Pettiford Amazing SoFLo Properties Inc.

164 Ocean Bay Dr Unit 3-C, Key Largo, FL 33037
/25
$685,000 Sold Jun 10, 2025

2601 S Roosevelt Blvd Unit 603 A, Key West, FL 33040
- 1 Bed
- 1 Bath
- 754 Sq Ft
- Built 1967
Last Sold Summary
- 10% Below List Price
- $908/SF
- 25 Days On Market
Current Estimated Value $659,730

Last Listing Agent Tom Mclaughlin Coldwell Banker Schmitt Real Estate Co. (KW)

2601 S Roosevelt Blvd Unit 603 A, Key West, FL 33040

/48
Est $584,282 Not Listed For Sale

10877 Overseas Hwy Unit 104, Marathon, FL 33050
- 1 Bed
- 1.5 Baths
- 850 Sq Ft
- Built 2022
10877 Overseas Hwy Unit 104, Marathon, FL 33050

Last Sold Summary
- 2% Below List Price
- $705/SF
- 69 Days On Market
Last Sold Price $599,000

Last Listing Agent Frank Griffiths Lokation Real Estate

/39
$485,000
- 1 Bed
- 1 Bath
- 754 Sq Ft
701 Spanish Main Dr Unit 182, Cudjoe Key, FL 33042

Oceanfront Paradise Awaits!Unit 182 in Venture OutExperience the epitome of Florida living in this charming one-bedroom, one-bathroom mobile home with Florida Room nestled within an exclusive gated community.This beautifully maintained home boasts:* Prime Canal front Location: Enjoy breathtaking ocean views and direct access to the water from your private 35 ft seawall.* Community Boat Ramp and

Ian Calderwood

Bluescape Real Estate

(786) 551-4336

701 Spanish Main Dr Unit 182, Cudjoe Key, FL 33042
/20

$2,950 - $3,650 per month

Tarpon Harbour

2 - 3 Beds

6973 Overseas Hwy, Marathon, FL 33050

Call Today to Book Your Appointment, we are eager to connect with you in Person!Tarpon Harbour is located in Monroe County, the 33050 ZIP Code, and the Monroe attendance zone.

6973 Overseas Hwy, Marathon, FL 33050
/34
$1,550,000 Sold Jun 02, 2025

1400 Virginia St, Key West, FL 33040
- 2 Beds
- 2 Baths
- 1,336 Sq Ft
- Built 1923
Last Sold Summary
- 3% Below List Price
- $1,160/SF
- 124 Days On Market
Current Estimated Value $1,604,827

Last Listing Agent Sean Farrer Coldwell Banker Schmitt Real E

1400 Virginia St, Key West, FL 33040

/40
Est $827,944 Not Listed For Sale

17236 Keystone Rd, Summerland Key, FL 33042
- 2 Beds
- 2 Baths
- 1,155 Sq Ft
- Built 1974
17236 Keystone Rd, Summerland Key, FL 33042

Last Sold Summary
- 5% Above List Price
- $680/SF
- 184 Days On Market
Last Sold Price $785,000

Last Listing Agent Everett Watkins Keller Williams Key West Compass Realty

/20
$214,500 Pending
- Land
701 Spanish Main Dr Unit 658, Cudjoe Key, FL 33042

RV Lot 658 is located in the exclusive gated community of Venture Out. Oceanfront Paradise Awaits!Experience the epitome of Florida living in beautiful Cudjoe Key, located right in between Key West and Marathon. * Community Boat Ramp and boat washdown station.* Community Amenities: Indulge in a resort-style lifestyle with access to a huge heated pool, spa, clubhouse, pickleball courts, tennis

Ian Calderwood

Bluescape Real Estate

(786) 418-4615

701 Spanish Main Dr Unit 658, Cudjoe Key, FL 33042
/24
$4,100 per month
- 2 Beds
- 3 Baths
- 1,068 Sq Ft
- Property for Rent
49 Coral Way, Key West, FL 33040

Coral Hammock is a wonderful gated community conveniently located within minutes of Key West. This townhome is clean, bright, and a dream for a Tenant. This home has all stainless steel kitchen appliances, gleaming wood floors and a great open floor plan with split bedrooms and baths upstairs, plus a half bath below. Ample covered parking for two vehicles. Convenient to great restaurants, retail

Wade Meyer Real Estate Management of Key West, LLC

49 Coral Way, Key West, FL 33040
/3
$1,090,000 Sold Jul 16, 2025

83 Coco Plum Dr, Marathon, FL 33050
- 6 Beds
- 4 Baths
- 2,072 Sq Ft
- Built 2025
Last Sold Summary
- $526/SF
- 0 Days On Market
Last Listing Agent Kim Show Coldwell Banker Schmitt Real Estate Co.

83 Coco Plum Dr, Marathon, FL 33050

/59
Est $636,551 Not Listed For Sale

97652 Overseas Hwy Unit 9, Key Largo, FL 33037
- 2 Beds
- 2 Baths
- 1,130 Sq Ft
- Built 1975
97652 Overseas Hwy Unit 9, Key Largo, FL 33037

Last Sold Summary
- 6% Above List Price
- $531/SF
- 88 Days On Market
Last Sold Price $600,000

Last Listing Agent Terri Bodker LoKation Real Estate - Pompano Beach

/71
$1,395,000
- 3 Beds
- 3 Baths
- 1,700 Sq Ft
16941 Driftwood Ln, Summerland Key, FL 33042

There are homes that check boxes, and then there are homes that speak to you the moment you step inside. This custom, meticulously crafted 3BR/3BA, 1,700 sq ft CBS masterpiece in the heart of Sugarloaf Shores is the latter, where thoughtful design, quiet elegance, and a touch of whimsy blend into a living experience that feels both luxurious and deeply personal.Set just 19 minutes from Key West,

Coby Taylor

Taylor & Assoc. RE, Inc.

(855) 606-6133

16941 Driftwood Ln, Summerland Key, FL 33042
/20

$2,854 - $3,961 per month

Lofts at Bahama Village

1 - 3 Beds

750 Fort St, Key West, FL 33040

Discover your place in the heart of Key West's most historic and vibrant neighborhood. The Lofts at Bahama Village offers affordable housing options designed for locals, where homeownership and rental opportunities meet the warmth of a close-knit community.Live steps away from iconic Key West landmarks, while enjoying the charm and cultural heritage that make Bahama Village truly one of a

750 Fort St, Key West, FL 33040
/39
$325,000 Sold Jul 11, 2025

6099 Overseas Hwy Unit 107W, Marathon, FL 33050
- 1 Bed
- 1 Bath
- 445 Sq Ft
- Built 2003
Last Sold Summary
- 26% Below List Price
- $730/SF
- 493 Days On Market
Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

6099 Overseas Hwy Unit 107W, Marathon, FL 33050

/29
Est $1,809,439 Not Listed For Sale

807 Washington St Unit 102, Key West, FL 33040
- 3 Beds
- 4 Baths
- 1,876 Sq Ft
- Built 2007
807 Washington St Unit 102, Key West, FL 33040

Last Sold Summary
- 10% Above List Price
- $880/SF
- 120 Days On Market
Last Sold Price $1,650,000

Last Listing Agent Kelli Houze Berkshire Hathaway HomeServices Knight & Gardner Realty

/49
$945,000 Open Sat 10AM - 12PM
- 2 Beds
- 2 Baths
- 960 Sq Ft
683 Blackbeard Rd, Summerland Key, FL 33042

Located near a canal 'T', this oceanside property offers easy docking for larger boats and sailboats in the 50 ft. wide, flow-through canal, putting the Atlantic and back-country within easy reach. The rooftop deck is a wonderful vantage point for panoramic neighborhood and water views. Nestled in mature vegetation, the one-owner, custom-built, board and batten cedar home has been well-maintained

Patti Nickless

Coldwell Banker Schmitt Lower Keys (KW)

(833) 982-0551

683 Blackbeard Rd, Summerland Key, FL 33042
/38
$6,500 per month
- 3 Beds
- 2 Baths
- 1,462 Sq Ft
- Property for Rent
506 Geiger Cir, Key Largo, FL 33037

Turnkey Key Largo waterfront living! Beautifully updated and fully furnished, this canal-front home offers quick ocean access--perfect for boaters. Enjoy a true Keys lifestyle with a tiki hut, fish cleaning station, outdoor shower, and private fenced yard for pets. Close to everything, yet feels like your own tropical escape.Owner covers landscaping, pest control, internet, and provides a $250

Isabella Medlin Keller Williams Key West Compass Realty

506 Geiger Cir, Key Largo, FL 33037
/4
$2,315,000 Sold Feb 20, 2026

1309 Petronia St, Key West, FL 33040
- 3 Beds
- 3 Baths
- 1,675 Sq Ft
- Built 1938
Last Sold Summary
- 2% Below List Price
- $1,382/SF
- 30 Days On Market
Current Estimated Value $2,308,080

Last Listing Agent Bobby Coe RE/MAX Keys Connection (KW)

1309 Petronia St, Key West, FL 33040

/17
Est $528,175 Not Listed For Sale

524 Margaret St Unit 101, Key West, FL 33040
- 1 Bed
- 1 Bath
- 370 Sq Ft
- Built 1938
524 Margaret St Unit 101, Key West, FL 33040

Last Sold Summary
- 5% Below List Price
- $1,505/SF
- 32 Days On Market
Last Sold Price $557,000

Last Listing Agent Joe Bracciale Select Properties of NWFL

/16
$250,000
- Land
- 0.02 Acre
- $12,500,000 per Acre
1801 N Roosevelt Blvd, Key West, FL 33040

LIVE IN PARADISE AFFORDABLE LIVEABOARD Houseboat & Slip (Package) at Garrison Bight Marina (Houseboat Row). It's a Leasehold to the City of Key West and with the Transfer of Title to your name. NO RENTALS, VRBO/AIRBNB! This community is Historic. It's a TRUE KEY WEST LIFESTYLE... POF CASH ONLY! If your ready to enjoy life and have a crash pad in the Florida Keys, then come and see this one.

Annie Rivera

Berkshire Hathaway Florida Realty

(645) 220-0406

1801 N Roosevelt Blvd, Key West, FL 33040
/20
$3,300 per month
- 3 Beds
- 2 Baths
- 1,100 Sq Ft
- House for Rent
29822 Frostproof Rd, Big Pine Key, FL 33043

Property Id: 2218567Enjoy comfort and privacy in this elevated 3-bedroom, 2-bath home, open floor plan and vaulted ceilings lots of windows and french doors. Furnished except for the smallest room. Make it your office or hobby room or guest room. The living room and master bedroom each open through French doors onto a balcony, Relax or entertain outdoors on the balcony/patio, and enjoy

29822 Frostproof Rd, Big Pine Key, FL 33043
/2
$1,030,000 Sold Nov 19, 2025

22521 Jolly Roger Dr, Cudjoe Key, FL 33042
- 4 Beds
- 3 Baths
- 1,728 Sq Ft
- Built 2010
Last Sold Summary
- $596/SF
- 0 Days On Market
Current Estimated Value $1,041,505

Last Listing Agent Patti Nickless Coldwell Banker Schmitt Lower Keys (KW)

22521 Jolly Roger Dr, Cudjoe Key, FL 33042

/43
Est $1,304,013 Not Listed For Sale

1050 Gulf Dr, Summerland Key, FL 33042
- 2 Beds
- 2 Baths
- 1,171 Sq Ft
- Built 1985
1050 Gulf Dr, Summerland Key, FL 33042

Last Sold Summary
- $1,110/SF
- 24 Days On Market
Last Sold Price $1,300,000

Last Listing Agent Michelle Howerton Brenda Donnelly Real Estate LLC

/60
$3,575,000
- 5 Beds
- 6 Baths
- 2,033 Sq Ft
1230 South St, Key West, FL 33040

1230 South Street stands as one of the most exquisite historic renovations ever completed in Key West. This five-bedroom, five-and-a-half-bath estate is a celebration of historical accuracy and modern luxury. Every detail, from the extensive use of original Dade County Pine to the rich ipe decking that frames the outdoor living spaces with warmth and durability, reflects reverence for the past

Damian Vantriglia

Berkshire Hathaway HomeServices Knight & Gardner Realty

(786) 840-2961

1230 South St, Key West, FL 33040
/20
$4,000 per month
- 2 Beds
- 2 Baths
- 1,080 Sq Ft
- House for Rent
142 Airstream Ln, Tavernier, FL 33070

Keep your boat right behind the house(up to 36') on a beautiful bayside canal full of life with manatees, turtles and tarpon. Seconds to open water and easy access to all the beautiful reefs, sandbars and fishing spots Islamorada has to offer.This recently built 2 bedroom, 2 bathroom home is spacious and being offered. furnished. Outside you have a beautiful outdoor living space made for enjoying

Megan Jones, LLC Coldwell Banker Schmitt Islamorada

142 Airstream Ln, Tavernier, FL 33070
/20
$1,500,000 Sold Jul 31, 2025

9922 Aviation Blvd, Marathon, FL 33050
- 4 Beds
- 4 Baths
- 1,666 Sq Ft
- Built 1980
Last Sold Summary
- 20% Below List Price
- $900/SF
- 137 Days On Market
Current Estimated Value $1,527,187

Last Listing Agent Stanley Rosen The Keyes Company

9922 Aviation Blvd, Marathon, FL 33050

/71
Est $5,741,988 Not Listed For Sale

522 Simonton St, Key West, FL 33040
- 5 Beds
- 6 Baths
- 3,342 Sq Ft
- Built 1869
522 Simonton St, Key West, FL 33040

Last Sold Summary
- 1% Above List Price
- $1,706/SF
- 115 Days On Market
Last Sold Price $5,700,000

Last Listing Agent Lisa Swanson The Agency Florida Keys

/44
$1,199,000
- 3 Beds
- 3 Baths
- 1,300 Sq Ft
1118 Eaton St, Key West, FL 33040

Step outside to your own slice of paradise - a private oasis that beckons you to unwind and rejuvenate. The sparkling pool, adorned with stunning blue mosaic tiles, creates a mesmerizing focal point, while the soothing sound of its waterfall feature transports you to a world of tranquility. Surrounding the pool, a spacious deck provides the perfect setting for sunbathing, alfresco dining, or

Matthew Carlson

Realty ONE Group Destination

(786) 788-8481

1118 Eaton St, Key West, FL 33040
/32
$3,252 per month
- 3 Beds
- 3 Baths
- 1,991 Sq Ft
- Condo for Rent
12400 Overseas Hwy Unit SI ID1269391P, Marathon, FL 33050

The advertised rate of $3,253/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 22, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

12400 Overseas Hwy Unit SI ID1269391P, Marathon, FL 33050
/40
$1,100,000 Sold Apr 25, 2025

88540 Overseas and Boat Slip 37 Hwy Unit 727, Plantation Key, FL 33070
- 2 Beds
- 2.5 Baths
- 1,298 Sq Ft
- Built 1985
Last Sold Summary
- 26% Below List Price
- $847/SF
- 157 Days On Market
Last Listing Agent Brett Newman Coldwell Banker Schmitt Islamorada

88540 Overseas and Boat Slip 37 Hwy Unit 727, Plantation Key, FL 33070

/22
Est $716,502 Not Listed For Sale

1627 George St, Key West, FL 33040
- 3 Beds
- 2 Baths
- 1,236 Sq Ft
- Built 1955
1627 George St, Key West, FL 33040

Last Sold Summary
- 2% Above List Price
- $566/SF
- 33 Days On Market
Last Sold Price $700,000

Last Listing Agent Bascom Grooms Bascom Grooms Real Estate (KW)

/46
$2,799,000 Open Sat 1PM - 3PM
- 2 Beds
- 3 Baths
- 2,124 Sq Ft
156 Sea Ln, Key West, FL 33040

Welcome to 156 Sea Lane, a residence that stands as a testament to architectural integrity and the vibrant history of the Florida Keys. This home was conceived and brought to life by its original owner, the legendary Reese Palley, who envisioned a sanctuary that combined the permanence of a fortress with the soul of an adventurer. Unlike the standard construction found throughout the islands, 156

Lisa Ferringo

Coldwell Banker Schmitt Real Estate Co

(786) 733-3907

156 Sea Ln, Key West, FL 33040
/27
$4,000 per month
- 3 Beds
- 2 Baths
- 2,201 Sq Ft
- House for Rent
141 Orchid St, Tavernier, FL 33070

Beautiful newer construction home available as an annual rental. Designed for indoor & outdoor entertaining. Located on a oversized lot. This property offers plenty of open parking with ample amount of space for boat and/or RV. 2 car garage for covered parking. House consists of 3 spacious bedrooms & 2 bathrooms. Master sweet has a sitting room, his & her walk in closest with built in shelving,

Hank Pinder Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

141 Orchid St, Tavernier, FL 33070
/36
$665,000 Sold Apr 07, 2025

2027 Staples Ave, Key West, FL 33040
- 2 Beds
- 1 Bath
- 784 Sq Ft
- Built 1958
Last Sold Summary
- $848/SF
- 0 Days On Market
Current Estimated Value $793,030

Last Listing Agent Jessica Forsythe eXp Realty LLC

2027 Staples Ave, Key West, FL 33040

/50
Est $1,503,987 Not Listed For Sale

115 Gulfwinds Ln, Marathon, FL 33050
- 3 Beds
- 2 Baths
- 1,546 Sq Ft
- Built 1995
115 Gulfwinds Ln, Marathon, FL 33050

Last Sold Summary
- 4% Above List Price
- $931/SF
- 28 Days On Market
Last Sold Price $1,440,000

Last Listing Agent Kasey Platt Florida Keys Real Estate Group

/40
$1,575,000
- 3 Beds
- 2 Baths
- 1,395 Sq Ft
1901 S Roosevelt Blvd Unit 401, Key West, FL 33040

Discover the rare opportunity to own a premier developer's unit in one of Key West's most desirable waterfront communities. Perfectly positioned just across the street from world-famous Smathers Beach, this spacious 3-bedroom, 2-bath condo blends coastal luxury with unbeatable island convenience.Inside, expansive living spaces open to large windows and glass doors showcasing ocean views and

Emily Lombard

Ocean Sotheby's International Realty

(786) 952-5592

1901 S Roosevelt Blvd Unit 401, Key West, FL 33040
/24
$18,964 per month
- 2 Beds
- 2 Baths
- 2,023 Sq Ft
- Condo for Rent
536 Fleming St Unit SI FL2-ID1297611P, Key West, FL 33040

The advertised rate of $18,964/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 8, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

536 Fleming St Unit SI FL2-ID1297611P, Key West, FL 33040
/56
$1,725,000 Sold Jul 11, 2025

17159 Amberjack Ln, Summerland Key, FL 33042
- 3 Beds
- 2 Baths
- 1,660 Sq Ft
- Built 1989
Last Sold Summary
- 14% Below List Price
- $1,039/SF
- 258 Days On Market
Current Estimated Value $1,721,652

Last Listing Agent Lisa Swanson The Agency Florida Keys

17159 Amberjack Ln, Summerland Key, FL 33042

/57
Est $938,296 Not Listed For Sale

11300 1st Avenue Gulf, Marathon, FL 33050
- 3 Beds
- 2 Baths
- 1,275 Sq Ft
- Built 1963
11300 1st Avenue Gulf, Marathon, FL 33050

Last Sold Summary
- 7% Above List Price
- $690/SF
- 103 Days On Market
Last Sold Price $880,000

Last Listing Agent Bonnie Sanderson Florida Keys Real Estate Group

Showing Results 121 - 160, Page 4 of 18

Florida Monroe County

How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Monroe County, FL Homes

Real Estate & Homes