Monroe County, FL Homes

/15
$320,000
- Land
27345 Guadaloupe Ln, Ramrod Key, FL 33042

Oceanside canal front lot with direct bridge free water access. Easy ride out to some of the Keys best fishing. Situated close to US 1 between Key West and Marathon. Restaurants, shopping and mini golf all nearby. Lot is currently in ROGO and the sewer meter is in place. Purchase a building right and start your dream home now or gather ROGO points and begin later. No HOA. Lot has been approved

Scott Brisson

KeyIsle Realty

(786) 983-9662

27345 Guadaloupe Ln, Ramrod Key, FL 33042
/12
$3,000 per month
- 2 Beds
- 1 Bath
- 700 Sq Ft
- Condo for Rent
1504 Flagler Ave Unit 1#, Key West, FL 33040

We are family oriented here at this property, we make our tenants feel at home like family.Partners allowed. Two single roommates. Pets allowed with deposit and referral letter from vet - shots are up to date. Owner will maintain jacuzzi 2x a month. One on-property parking spot allowed per unit. Smoke free property.

1504 Flagler Ave Unit 1#, Key West, FL 33040
/40
$6,500,000 Sold Aug 26, 2025
- 3,860 Sq Ft
- $1,684/SF
- 49 Days On Market
- 4 Beds
- 4.5 Baths
- Built 2025
128 Sunrise Dr, Marathon, FL 33050

' Completed August 2025 ' Nestled on the exclusive, gated island of Sunrise Isles in Marathon, Florida Keys, this magnificent new construction oceanfront estate redefines luxury living. With only 20 residences on this private island, you'll experience a rare blend of privacy and community, surrounded by the serene beauty of the Keys. This exquisite 4-Bedroom, 5-Bathroom residence spans 3,900

Placido Rodriguez LoKation Real Estate

128 Sunrise Dr, Marathon, FL 33050

/2
Not Listed For Sale
- 2 Beds
- 2 Baths
- 960 Sq Ft
808 Oakwood Ave, Key Largo, FL 33037

808 Oakwood Ave, Key Largo, FL 33037

/44
$1,699,000
- 3 Beds
- 2 Baths
- 1,666 Sq Ft
27314 Saint Lucie Ln, Ramrod Key, FL 33042

Brand new concrete waterfront pool home on a corner canal lot with an exceptional 204' of water frontage, including the main canal, and just moments from open ocean access! This stunning home is built to withstand 180 mph winds, featuring impact-rated doors and windows, a metal roof, and solid concrete construction.Enjoy Florida Keys boating with a 40' concrete dock, 15,000 lb boat lift, and

Lisa Ferringo

Coldwell Banker Schmitt Lower Keys (KW)

(786) 783-4784

27314 Saint Lucie Ln, Ramrod Key, FL 33042
/26
$4,000 per month
- 2 Beds
- 2 Baths
- Townhouse for Rent
182 Paradise Way, Islamorada, FL 33036

Now available for an annual rental at Sun Outdoors! This beautifully furnished 2 bedroom, 2 bath stilted home offers resort-style living right on Plantation Key. Enjoy a balcony off the living room with ocean views, a fully equipped kitchen, and inviting living spaces. Community amenities include a residents-only pool, fitness center, and tiki hut overlooking the water. A boat slip is included

Courtney Jeffers Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

182 Paradise Way, Islamorada, FL 33036
/29
$875,000 Sold Aug 26, 2025
- 1,038 Sq Ft
- $843/SF
- 234 Days On Market
- 2 Beds
- 2 Baths
- Built 1955
11282 2nd Avenue Ocean, Marathon, FL 33050

New Roof being installed! Waterfront Sanctuary in Marathon, FL - 11282 2nd Ave OceanWelcome to your coastal paradise--a fully remodeled 2-bedroom waterfront retreat designed for both relaxation and adventure.This property boasts an impressive 160-foot dock with a 17,000 lb. boat lift, providing direct access to world-class fishing and diving. Reach the Atlantic in just 2 minutes and the Gulf in 5

Sam Williams Coldwell Banker Schmitt Real Estate Co.

11282 2nd Avenue Ocean, Marathon, FL 33050

/47
Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,232 Sq Ft
500 Hazel St, Key Largo, FL 33037

500 Hazel St, Key Largo, FL 33037

/60
$3,995,000
- 4 Beds
- 3 Baths
- 4,204 Sq Ft
505 Caribbean Dr, Key Largo, FL 33037

A Waterfront Masterpiece -- 166 feet of pristine canal frontage, resort-style pool, and a massive owner's suite define this one-of-a-kind residence.Beautiful and spacious 3-story waterfront residence offering an impressive 166 feet of canal frontage with direct access to the ocean. Designed for comfort and entertaining, this home blends elegant interiors with resort-style outdoor living.Inside,

Terry Canto

American Caribbean Real Estate, Christie's International Real Estate

(786) 982-0864

505 Caribbean Dr, Key Largo, FL 33037
/18
$4,400 per month
- 2 Beds
- 1 Bath
- 1,000 Sq Ft
- Condo for Rent
1505 White St Unit Two bedroom, Key West, FL 33040

This property at 1505 White two bedrooms and one bathroom, encompassing a total of over 1000 square feet. With over 700 sq ft of outdoor living The unit comes furnished and includes air conditioning for climate control. The smoke-free environment ensures a healthy living space. Exterior amenities include a gated entry for added security, a grill for outdoor cooking, and a deck for relaxation or

1505 White St Unit Two bedroom, Key West, FL 33040
/31
$275,000 Sold Aug 25, 2025
- 1,073 Sq Ft
- $256/SF
- 19 Days On Market
- 2 Beds
- 1 Bath
- Built 1964
22 Atlantic Dr, Key Largo, FL 33037

Opportunity knocks in the heart of Key Largo! This property sits on a 7,500 sq/ft lot just minutes from waterfront dining, shopping, marinas, and Publix. Enjoy nearby parks like John Pennekamp Coral Reef State Park and quick access to U.S.-1 for easy travel throughout the Keys. The home is in need of repair but offers a prime chance to renovate or rebuild in one of the most desirable locations in

Julie Sidorevskaya Julies Realty, LLC

22 Atlantic Dr, Key Largo, FL 33037

/2
Est $1,614,380 Not Listed For Sale
- 4 Beds
Unlisted Address

Unlisted Address

/32
$1,199,000
- 3 Beds
- 2 Baths
- 1,494 Sq Ft
27417 Tobago Ln, Ramrod Key, FL 33042

This custom-built 3-bedroom, 2-bathroom residence on Ramrod Key offers a spacious, split floorplan, 1500 sq ft and is just 27 miles from Key West. The high quality 2010 construction features a hip metal roof, hardi plank siding, impact windows, and doors, ensuring durability and peace of mind. The heart of this home is its large kitchen, designed for both function and style. With an abundance of

Sandra Tuttle

Island Welcome Real Estate

(786) 822-7622

27417 Tobago Ln, Ramrod Key, FL 33042
/9
$3,000 per month
- 2 Beds
- 2 Baths
- 804 Sq Ft
- Property for Rent
3930 S Roosevelt Blvd Unit 109N, Key West, FL 33040

AVAILABLE NOW!! Las Salinas condominium. Two bedrooms and two baths located on the first floor. Its private balcony overlooks the pool.Las Salinas is located on South Roosevelt Blvd across the street from the oceanfront boardwalk perfect for biking, jogging and walking as it curves along the coastline toward Smathers Beach. This unit comes with its own private storage room. In addition to the

Rebecca Cobo Berkshire Hathaway HomeServices Knight & Gardner Realty

3930 S Roosevelt Blvd Unit 109N, Key West, FL 33040
/27
$750,711 Sold Aug 25, 2025
- 1,000 Sq Ft
- $751/SF
- 3 Days On Market
- 2 Beds
- 2 Baths
- Built 1981
81975 Old Hwy, Islamorada, FL 33036

Bright and airy Keys home in the Heart of Islamorada! Old Highway location popular with walkers, runners, and cyclists. You're just a short stroll from 'downtown' Islamorada's best restaurants, shops, and galleries. Step inside to soaring tongue-and-groove ceilings that create an open, airy vibe, complemented by warm wood flooring and abundant natural light throughout. The spacious living and

Christy Hughes Coldwell Banker Schmitt Islamorada

81975 Old Hwy, Islamorada, FL 33036

/37
Est $2,271,432 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,581 Sq Ft
1701 Laird St, Key West, FL 33040

1701 Laird St, Key West, FL 33040

/16
$675,000
- Land
17215 Keystone Rd, Sugarloaf Shores, FL 33042

Cleared canal-front lot in Sugarloaf Shores with building permit in place and first inspection not due until December 2026! Positioned on the desirable no-bridge side, this expansive 27,716 sq. ft. residential parcel is surrounded by multi-million-dollar homes and offers easy access to the open water where days are enjoyed paddling and kayaking through mangrove-line creeks or heading out to

Lisa Ferringo

Coldwell Banker Schmitt Lower Keys (KW)

(786) 957-7959

17215 Keystone Rd, Sugarloaf Shores, FL 33042
/19
$4,000 per month
- 2 Beds
- 2.5 Baths
- 842 Sq Ft
- Townhouse for Rent
63 Seaside Ct N, Key West, FL 33040

Seaside Key West Residents is a fully gated Community divided in two sections. This townhouse has the feel of tropical living and add to that a garage with storage, rear yard, a clubhouse, gym and a pool for each side. Manager on site, security gate/cameras provide privacy with the Atlantic Ocean just across S. Roosevelt Boulevard. Sturdy concrete construction, impact resistant windows &

63 Seaside Ct N, Key West, FL 33040
/51
$900,000 Sold Aug 25, 2025
- 1,463 Sq Ft
- $615/SF
- 37 Days On Market
- 2 Beds
- 2 Baths
- Built 1930
318 Margaret St, Key West, FL 33040

Historic charm meets modern comfort in this beautifully preserved 1930 Conch cottage nestled in Key West's sought-after Historic Seaport district. This two-story, 2-bedroom, 2-bath home (approximately 1,463 sq ft) boasts classic Key West architecture - wood siding and a metal roof - along with inviting outdoor spaces including an open front porch and a private backyard oasis. Inside, airy living

Jose Wenzel, PA Preferred Properties (KW)

318 Margaret St, Key West, FL 33040

/9
Est $2,561,818 Not Listed For Sale
- 3 Beds
234 Pescayo Ave, Marathon, FL 33050

234 Pescayo Ave, Marathon, FL 33050

/9
$499,000
- 2 Beds
- 1 Bath
- 460 Sq Ft
6 Beach Dr, Key West, FL 33040

Rare ROGO EXEMPT property on the open water with boating access located in the Saddlebunch Keys, just 10 minutes from all of the superior dining and nightlife of Key West, Florida. Build your dream home now, and enjoy beautiful open water sunset views forever. ROGO EXEMPT LETTER IN HAND, no waiting for a building right, this property comes with it. Complete renovation or replacement of

Anneliese Dietrick

Coldwell Banker Schmitt Lower Keys (KW)

(786) 756-8747

6 Beach Dr, Key West, FL 33040
/3
$2,500 per month
- 2 Beds
- 1 Bath
- 800 Sq Ft
- Property for Rent
7 Sunset Rd Unit 4, Key Largo, FL 33037

Welcome to Paradise!!! enjoy living in this fully renovated 2/1 Unit. This unit is located in a great neighborhood in Key Largo close to great schools and shopping and fantastic restaurants. This unit offers brand new A/C units custom kitchen including Quartz countertops and new S/S appliances. large Fully renovated Bathroom with all modern fixtures. This unit also offers impact windows and new

Germain Garcia, PA Lifestyle International Realty

7 Sunset Rd Unit 4, Key Largo, FL 33037
/30
$786,000 Sold Aug 25, 2025
- 1,188 Sq Ft
- $662/SF
- 95 Days On Market
- 2 Beds
- 2 Baths
- Built 1993
1530 Ocean Bay Dr Unit 509, Key Largo, FL 33037

Top-Floor Oceanfront Condo | STR Rentals Approved | Income-ProducingInvestor alert! This stunning top-floor 2BD/2BA condo in Kawama Tower offers breathtaking panoramic ocean views and is fully approved for short-term rentals--making it a rare and highly desirable income-producing property in Key Largo.Turn-key and rental-ready, the unit features impact windows and doors, an updated kitchen, new

Terry Canto American Caribbean Real Estate, Christie's International Real Estate

1530 Ocean Bay Dr Unit 509, Key Largo, FL 33037

/2
Not Listed For Sale
- 8,460 Sq Ft
0 Coconut Dr, Key Largo, FL 33037

0 Coconut Dr, Key Largo, FL 33037

/51
$1,299,000
- 4 Beds
- 3 Baths
- 1,888 Sq Ft
231 Sombrero Beach Rd Unit 1, Marathon, FL 33050

Experience the ultimate in Florida Keys living at this canal front 4-bedroom, 3-bath 1,888 sq. ft. half-duplex pool home located in the heart of Marathon. Ideally located just down the street from stunning Sombrero Beach, this waterfront retreat offers deep water dockage with ocean acces, a private heated pool, and desirable weekly rental zoning with good rental history. Inside, enjoy an

Lisa Ferringo

Coldwell Banker Schmitt Lower Keys (KW)

(786) 475-6930

231 Sombrero Beach Rd Unit 1, Marathon, FL 33050
/13
$1,600 per month
- Studio
- 1 Bath
- 475 Sq Ft
- Condo for Rent
3407 Eagle Ave Unit Eagle Cottage, Key West, FL 33040

Private Studio Cottage includes all utilities, TV, internet/wifi and off street parking parking $1600 monthly

3407 Eagle Ave Unit Eagle Cottage, Key West, FL 33040
/18
$170,000 Sold Aug 25, 2025
- Land
- 0.00 Acre
- 105 Days On Market
1801 N Roosevelt Blvd Unit Wahoo 39, Key West, FL 33040

PERFECT CONDITION 1990 MARINE TRADER AND LIVEABOARD SLIP LEASEHOLD IN THE HEART OD KEY WEST. SILD TOGETHER ONLY. SEAWORTHY VESSEL WITHCAPTAIN'S BERTH, VBERTH, SALON, GALLEY, FLY BRIDGE, TWIN DIESELS. A RARE FIND IN THE HEART OF KEY WEST !

Randy Moss Coldwell Banker Schmitt RE Co

1801 N Roosevelt Blvd Unit Wahoo 39, Key West, FL 33040

/55
Est $2,251,829 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,034 Sq Ft
296 Buttonwood Shores Dr, Key Largo, FL 33037

296 Buttonwood Shores Dr, Key Largo, FL 33037

/30
$829,000
- 4 Beds
- 2 Baths
- 1,456 Sq Ft
26868 Mariposa Rd, Ramrod Key, FL 33042

Presenting a newly built 2023 home on a spacious 12,250 sq. ft. lot in Ramrod Shores, designed with both efficiency and style in mind. This four-bedroom, two-bathroom property features durable construction elements like a metal roof and impact-resistant windows, optimizing insurance costs, with all 3 insurances combined under $5,000 total. The interior boasts an open-concept floor plan with high

Dan Serban

Key West Luxury Real Estate Inc (KW)

(786) 783-4956

26868 Mariposa Rd, Ramrod Key, FL 33042
/25
$2,500 per month
- 1 Bed
- 1 Bath
- 660 Sq Ft
- Townhouse for Rent
10 Clara Blvd, Key Colony Beach, FL 33051

This charming 1 bedroom, 1 bathroom half-duplex offers the perfect blend of comfort and Keys living. Bright and airy with an open floor plan, it features a spacious living area, updated kitchen, brand new AC units, impact windows and doors, and a private outdoor space to enjoy the ocean breeze.Centrally located near shops, dining, and Sunset Park. This property is ideal for those looking to enjoy

Nate Bartlett Berkshire Hathaway HomeServices Keys Real Estate

10 Clara Blvd, Key Colony Beach, FL 33051
/53
$2,290,000 Sold Aug 25, 2025
- 2,028 Sq Ft
- $1,129/SF
- 250 Days On Market
- 4 Beds
- 4 Baths
- Built 2020
831 Georgia St, Key West, FL 33040

Beautiful Meadows Masterpiece located one of Key West's idyllic neighborhoods. Built in 2020 using the finest materials and craftsmanship, this home combines the best of Key West Architecture with modern luxury finishes.Exquisite Nickel-grooved walls and stunning hardwood floors that create a warm and inviting atmosphere. The coffered ceilings, adorned with Dade County Pine add that extra touch

Suzanne Moore Suzanne Moore Real Estate

831 Georgia St, Key West, FL 33040

/2
Est $701,133 Not Listed For Sale
- 3 Beds
40 Hibiscus Ln, Key Largo, FL 33037

40 Hibiscus Ln, Key Largo, FL 33037

/27
$1,175,000
- 3 Beds
- 2 Baths
- 1,070 Sq Ft
18 W Circle Dr, Key West, FL 33040

This beautifully remodeled 3-bedroom, 2-bath stilted home sits canal-side behind Baby's Coffee, offering open water views and great opportunity. Built in 2000, it features a durable metal roof, impact windows, and sliding glass doors for comfort and great insurance options. Launch your boat from your own private ramp or use the community ramp nearby, then relax in the sparkling pool or tinker in

Dan Serban

Key West Luxury Real Estate Inc (KW)

(786) 783-6419

18 W Circle Dr, Key West, FL 33040
/6
$2,200 per month
- Studio
- 1 Bath
- 252 Sq Ft
- Condo for Rent
908 Elizabeth St Unit 4, Key West, FL 33040

Very cute little garden studio available Early August. Small but in the very HEART of it all! Walk to everything Old Town has to offer! Tenant pays electric and cable/internet. F/S/S. Sorry No Pets!

908 Elizabeth St Unit 4, Key West, FL 33040
/5
$625,000 Sold Aug 22, 2025
- 810 Sq Ft
- $772/SF
- 0 Days On Market
- 2 Beds
- 1 Bath
- Built 1973
44 Bonefish Ave, Key Largo, FL 33037

Beautifully updated home in Largo Sound subdivision.

Amy Bruggeman American Caribbean Real Estate, Christie's International Real Estate

44 Bonefish Ave, Key Largo, FL 33037

/22
Est $420,461 Not Listed For Sale
- 2 Beds
- 1.5 Baths
- 1,180 Sq Ft
40 High Point Rd Unit B-102, Tavernier, FL 33070

40 High Point Rd Unit B-102, Tavernier, FL 33070

/52
$3,500,000
- 4 Beds
- 3.5 Baths
- 2,700 Sq Ft
Unlisted Address

🌴 Port Largo Waterfront Paradise 🌴Located in one of Key Largo's most desirable neighborhoods, this canal front 4-bedroom, 3.5-bath pool home is truly a boater's dream. Whether you're bringing the whole family or your fishing crew, there's room here for everyone--and all the gear that goes along with all the water sports!Inside, the home welcomes you with light-filled living

Krissy Carnahan

Realty ONE Group Destination (ISL)

(645) 654-8535

Unlisted Address
/34
$5,000 per month
- 2 Beds
- 2 Baths
- 726 Sq Ft
- House for Rent
325 Calusa St Unit 320, Key Largo, FL 33037

Key Largo Waterfront Paradise Awaits Step into your dream escape with this stunning 2-bedroom, 2-bath canal-front gem in the coveted Calusa subdivision. With panoramic open water views and direct access to the Florida Keys' aquatic playground, this home is your gateway to endless adventure and relaxation.

Jose Vigo RE/MAX All Keys Real Estate

325 Calusa St Unit 320, Key Largo, FL 33037
/57
$1,000,000 Sold Aug 22, 2025
- 988 Sq Ft
- $1,012/SF
- 6 Days On Market
- 2 Beds
- 2 Baths
- Built 1960
263 Azalea St, Tavernier, FL 33070

A MUST SEE! Its not only the most affordable CANALFRONT deal in Islamorada! Its also a Conch-Style home in Plantation Key Colony!This adorable ground-level home is nestled in one of the most desirable neighborhoods in the Upper Keys Plantation Key Colony in Islamorada. Known for its friendly, close-knit community, the neighborhood offers easy access to both a top-rated K-8 school and high school,

Kelly Randin RE/MAX All Keys Real Estate

263 Azalea St, Tavernier, FL 33070

/42
Est $1,551,556 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,617 Sq Ft
127 W Avenue A, Key Largo, FL 33037

127 W Avenue A, Key Largo, FL 33037

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