Monroe County, FL Homes

/41
$899,000
- 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
/50
$4,100 per month
- 2 Beds
- 2 Baths
- 1,288 Sq Ft
- Property for Rent
240 Taylor Dr, Key Largo, FL 33037

Beautifull and charming 2BD/2BA waterfront home on a spacious 6,660 sqft lot. Featuring a 60ft dock, boat lift, fish cleaning station, and storage sheds. Perfect for boat enthusiasts. Close to Adams Cut, North & South Channel. Spacious patio, perfect for family gatherings and relaxing. Easy access to grocery stores, restaurants and establishments. 1hr from Miami Airport. Voluntary HOA with boat

Catherine Fox Luxe Properties, LLC.

240 Taylor Dr, Key Largo, FL 33037
/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 $1,614,928

Last Listing Agent Sean Farrer Coldwell Banker Schmitt Real E

1400 Virginia St, Key West, FL 33040

/3
Est $1,395,229 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 1,746 Sq Ft
292 Woods Ave, Tavernier, FL 33070

292 Woods Ave, Tavernier, FL 33070

/39
$495,000
- 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
$3,525 per month
- 2 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 2-bedroom, 2-bath home featuring an extra bedroom, open floor plan and vaulted ceilings for a bright, airy feel. The living room and master bedroom each open through French doors onto a balcony, while the bonus bedroom offers its own private sliding door access. Central A/C and heat keep the home comfortable year-round. Relax

29822 Frostproof Rd, Big Pine Key, FL 33043
/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

/15
Est $773,048 Not Listed For Sale
Unlisted Address

Unlisted Address

/20
$224,500
- 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
/41
$3,750 per month
- 3 Beds
- 2 Baths
- 1,040 Sq Ft
- House for Rent
139 N Bay Harbor Dr, Key Largo, FL 33037

Heaven on earth. Great energy!!! Peaceful, quiet, & invigorating Fully Furnished 3 br, 2 bth home with access to a private beach and marina, with a tiki and picnic area (one minute walk) including a boat ramp. Highly desired quiet neighborhood on the bayside. Home is furnished. Open floor plan with cathedral ceilings. New appliances, refrigerator and oven with air fryer mode. Also full size

Richard Capote Capote Global Realty LLC

139 N Bay Harbor Dr, Key Largo, FL 33037
/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 Lower Keys (KW)

6099 Overseas Hwy Unit 107W, Marathon, FL 33050

/27
Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,360 Sq Ft
115 Long Key Rd, Key Largo, FL 33037

115 Long Key Rd, Key Largo, FL 33037

/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
$5,528 per month
- 3 Beds
- 3 Baths
- 1,991 Sq Ft
- Condo for Rent
12400 Overseas Hwy Unit ID1269391P, Marathon, FL 33050

Welcome to Rooftop Bliss, the ultimate family getaway in Marathon, FL! This spacious 3-bedroom, 3-bathroom villa is perfect for making memories together, with a private rooftop deck, resort-style pool, and a safe, gated community. Close to beaches, fishing spots, and fun island attractions, it's your home away from home in the Florida Keys.This beautiful three-level villa has everything your

12400 Overseas Hwy Unit ID1269391P, Marathon, FL 33050
/30
$710,000 Sold Jan 24, 2025

982 81st St, Marathon, FL 33050
- 2 Beds
- 3 Baths
- 1,080 Sq Ft
- Built 1986
Last Sold Summary
- 11% Below List Price
- $657/SF
- 26 Days On Market
Last Listing Agent Peter Schwarz-Top Producer LoKation Real Estate

982 81st St, Marathon, FL 33050

/57
Est $5,590,147 Not Listed For Sale
- 5 Beds
- 5.5 Baths
- 5,200 Sq Ft
124 Sunrise Dr, Marathon, FL 33050

124 Sunrise Dr, Marathon, FL 33050

/25
$749,000
- Land
6000 Peninsular Ave Unit LU28, Stock Island, FL 33040

This 80-foot boat slip at Stock Island Marina offers a rare combination of premium location, full-service amenities, and exceptional value. With direct deepwater access to the Atlantic, you can be on the oceanside of Key West in just seconds--perfect for serious boaters and weekend cruisers alike.The slip features floating docks on both sides, making boarding and disembarking smooth and

Cardenas & Krug Team

Ocean Sotheby's International Realty

(786) 876-7466

6000 Peninsular Ave Unit LU28, Stock Island, FL 33040
/24
$4,000 per month
- 3 Beds
- 2 Baths
- House for Rent
793 Oceana Ave, Key Largo, FL 33037

Warm & InvitingEnjoy this brand-new 3-bedroom, 2-bath upstairs residence, fully furnished and move-in ready. The home features stainless steel appliances, including a dishwasher, microwave, oven range, refrigerator, and washer and dryer. Situated on Oceana Avenue, a peaceful dead-end street that leads to Largo Sound. Ideally located just one hour from Miami and minutes from dining, shopping, and

Ralph Sam Real Estate Sales Force, Inc.

793 Oceana Ave, Key Largo, FL 33037
/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 $1,552,195

Last Listing Agent Stanley Rosen The Keyes Company

9922 Aviation Blvd, Marathon, FL 33050

/42
Est $1,925,143 Not Listed For Sale
- 4 Beds
- 4 Baths
- 2,800 Sq Ft
106 Tequesta St, Tavernier, FL 33070

106 Tequesta St, Tavernier, FL 33070

/43
$1,089,000 Under Contract
- 2 Beds
- 1 Bath
- 1,056 Sq Ft
29039 Cedar Dr, Big Pine Key, FL 33043

100 ft. canal-frontage, 15K boat lift, tiki hut and pool..... this Lower Keys property feels like your own private mini resort along the 50 ft. wide canal. The 10,000 sq. ft. double lot is strategically fenced to allow easy parking for multiple vehicles including boat trailer and RV parking. Picture yourself relaxing under the 12' x 18' poolside tiki or in one of numerous sitting areas amidst the

Patti Nickless

Coldwell Banker Schmitt Lower Keys (KW)

(855) 368-1692

29039 Cedar Dr, Big Pine Key, FL 33043
/20
$8,250 per month
- 3 Beds
- 2 Baths
- 1,431 Sq Ft
- Condo for Rent
886 Loggerhead Ln Unit ID1297829P, Summerland Key, FL 33042

Loggerhead Lagoon is a stunning, tropically themed 3-bedroom 2-bathroom home located on a large private lot that offers covered parking, a boat dock, and direct access to the Gulf of Mexico. This rare find boasts a lush outdoor area full of beautiful palms, sun loungers, and tons of Florida sunshine. Located in Sugarloaf Key, just 19 miles from Key West and the world-famous Duval Street, this

886 Loggerhead Ln Unit ID1297829P, Summerland Key, FL 33042
/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
Last Listing Agent Patti Nickless Coldwell Banker Schmitt Lower Keys (KW)

22521 Jolly Roger Dr, Cudjoe Key, FL 33042

/68
Est $3,115,908 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 3,470 Sq Ft
127 Marina Ave, Key Largo, FL 33037

127 Marina Ave, Key Largo, FL 33037

/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
/9
$2,900 per month
- 2 Beds
- 2 Baths
- 1,072 Sq Ft
- Property for Rent
3930 S Roosevelt Blvd Unit N303, Key West, FL 33040

Large 2/2 with new carpet, assigned covered parking for two autos, hurricane shutters, walkin closets, in unit laundry center. Very large kitchen for the cook! Fitness center available for additional fee, see condo manager. Assigned Storage unit ! No last months rent required for qualified tenants. No pets as per condominium regulations, background required by condominium association

Darlene Thomas Beach Club Brokers (KW)

3930 S Roosevelt Blvd Unit N303, Key West, FL 33040
/8
$3,366,600 Sold Feb 25, 2025

59720 Overseas Hwy, Marathon, FL 33050
- 5 Beds
- 4.5 Baths
- 3,011 Sq Ft
- Built 2023
Last Sold Summary
- 2% Above List Price
- $1,118/SF
- 275 Days On Market
Last Listing Agent Greg MacLaren Internet Realty of the Florida

59720 Overseas Hwy, Marathon, FL 33050

/10
Est $803,016 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,400 Sq Ft
57434 Gibson St, Marathon, FL 33050

57434 Gibson St, Marathon, FL 33050

/35
$875,000 Open House 1/03
- 2 Beds
- 2 Baths
- 1,040 Sq Ft
47 Sadowski, Key Colony, FL 33051

Welcome to Turquoise Lagoon, your stunning 2-bedroom, 2-bath waterfront retreat that captures the essence of Florida Keys living. Perfectly positioned on Bonefish Bay, this turnkey oasis offers spectacular open bay views and two private docks for effortless access to the sea. Stepping inside, you are welcomed by a bright and inviting kitchen featuring granite countertops, a center island with

Ryan Gernaat

Coldwell Banker Schmitt Lower Keys (KW)

(786) 659-1279

47 Sadowski, Key Colony, FL 33051
/24
$11,977 per month
- 2 Beds
- 2 Baths
- 2,023 Sq Ft
- Condo for Rent
536 Fleming St Unit FL2-ID1297611P, Key West, FL 33040

Experience the allure of this luxurious 2,000+ square foot penthouse, The Maloney, which occupies the entire second story of a historic red brick building at the corner of Fleming and Simonton. Originally constructed in 1908 as Key West's first pharmacy, this building now features two penthouse units and a first-floor boutique. The Maloney is available exclusively for monthly rentals, requiring a

536 Fleming St Unit FL2-ID1297611P, Key West, FL 33040
/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

/2
Est $3,156,849 Not Listed For Sale
- 4 Beds
- 5 Baths
- 2,539 Sq Ft
80639 Old Hwy Unit 203, Islamorada, FL 33036

80639 Old Hwy Unit 203, Islamorada, FL 33036

/53
$2,899,000
- 3 Beds
- 4 Baths
- 2,286 Sq Ft
814 Ashe St, Key West, FL 33040

Built in 2008, this stunning 3-bedroom, 3.5-bath pool home perfectly blends the timeless character of classic Key West architecture with the comfort and convenience of modern construction. Ideally located just a short stroll from shops, restaurants, bars, and the world-famous Duval Street, this home offers the best of island living. Step inside to a bright, open-concept main living space with a

Lisa Ferringo

Coldwell Banker Schmitt Lower Keys (KW)

(786) 981-0872

814 Ashe St, Key West, FL 33040
/19
$5,000 per month
- 2 Beds
- 2 Baths
- 1,068 Sq Ft
- House for Rent
826 Bonito Ln, Key Largo, FL 33037

Oceanside ground level Canalfront gem! This gorgeous 2 bedrooms and 2 bathrooms home has been completely updated. This concrete home offers a concrete dock, clear canal with a boatlift and a boat ramp,fish cleaning area, and above ground pool. Enjoy the ocean breeze from the back terrace that overlooks the clear canal. This home offers a nice big lot in a multi-million dollar neighborhood. This

Roger Schaeffler Florida Realty of Miami Corp

826 Bonito Ln, Key Largo, FL 33037
/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 $829,789

Last Listing Agent Jessica Forsythe eXp Realty LLC

2027 Staples Ave, Key West, FL 33040

/53
Est $2,173,959 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 1,829 Sq Ft
81906 Overseas Hwy, Islamorada, FL 33036

81906 Overseas Hwy, Islamorada, FL 33036

/48
$2,150,000
- 3 Beds
- 2 Baths
- 2,127 Sq Ft
1501 Ocean Bay Dr Unit A1 & 50' Boat Slip, Key Largo, FL 33037

Luxury Ocean Front End Unit. The best views from the complex in this townhome with 50 ft deeded slip and boat lift. Indulge in the vibrant ocean colors of turquoise blues and greens from every room. Awaken to awe-inspiring sunrises accompanied by refreshing ocean breezes. This hidden gem has the best views in the exclusive Key Largo Yacht Club with the boat slip just steps away. Convenience,

Terry Canto

American Caribbean Real Estate, Christie's International Real Estate

(305) 614-8966

1501 Ocean Bay Dr Unit A1 & 50' Boat Slip, Key Largo, FL 33037
/17
$3,500 per month
- 2 Beds
- 2 Baths
- 912 Sq Ft
- House for Rent
30612 23rd Ln, Big Pine Key, FL 33043

Property Id: 2240886Discover the beauty of Big Pine Key from this delightful 2-bedroom house. With a king bed and a queen bed, guests can relax in comfort. Enjoy the convenience of WiFi, AC, and a washing machine during your stay. The 2 bathrooms are equipped with all of the conveniences of home. Located between the Back Bay and the Ocean. Property sits on an acre lot, enjoy the breezy,

30612 23rd Ln, Big Pine Key, FL 33043
/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 $1,670,102

Last Listing Agent Lisa Swanson The Agency Florida Keys

17159 Amberjack Ln, Summerland Key, FL 33042

/2
Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,400 Sq Ft
104000 Overseas Hwy Unit 1, Key Largo, FL 33037

104000 Overseas Hwy Unit 1, Key Largo, FL 33037

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

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

Homes in Nearby Neighborhoods

Homes in Nearby Cities

Homes in Nearby Counties

Homes in Nearby Zip Codes

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