Monroe County, FL Homes

/89
$4,997,000
- 5 Beds
- 7 Baths
- 3,597 Sq Ft
113 Court Contessa, Islamorada, FL 33036

Introducing one of the most exceptional homes ever offered in prestigious Port Antigua! Casa Contessa is a 2023 modern coastal estate built by the seller for the seller, with every feature intentionally selected to be top-tier. This 5BR/6.5BA, 3,597 sq ft residence is engineered to perfection with full CBS construction, impact windows/doors, and a true concrete roof.Tucked on a quiet cul-de-sac,

Coby Taylor

Taylor & Assoc. RE, Inc.

(645) 238-6287

113 Court Contessa, Islamorada, FL 33036
/6
$4,000 per month
- 2 Beds
- 2 Baths
- 3,364 Sq Ft
- Apartment for Rent
26 S Exuma Rd Unit B, Key Largo, FL 33037

***Key Largo***Gorgeous and conveniently located, 2 BD/2BA with a private home feel. Unit located on 3rd floor. Only two apartments. Enjoy your morning coffee in the screened in balcony. Then head out on your boat with easy ocean access. 30' dock space. No cats allowed. More pictures to come.

Lizette Martin London Foster Realty

26 S Exuma Rd Unit B, Key Largo, FL 33037
/57
$796,200 Sold Mar 11, 2025

88500 Overseas Hwy Unit 502, Tavernier, FL 33070
- 3 Beds
- 2 Baths
- 1,567 Sq Ft
- Built 1976
Last Sold Summary
- 16% Below List Price
- $508/SF
- 208 Days On Market
Current Estimated Value $837,634

Last Listing Agent Terry Canto American Caribbean Real Estate, Christie's International Real Estate

88500 Overseas Hwy Unit 502, Tavernier, FL 33070

/3
Not Listed For Sale
1008-1010 Gibraltar Rd, Key Largo, FL 33037

1008-1010 Gibraltar Rd, Key Largo, FL 33037

/60
$3,350,000
- 4 Beds
- 4 Baths
- 2,649 Sq Ft
1240 Coury Dr, Key Colony Beach, FL 33051

This exquisite 4 Bedroom, 4 Bathroom residence has been completely reimagined into a stunning Coastal Modern masterpiece, designed to offer both serene vacation vibes and cutting-edge comfort. Set on an oversized 12,090 sq ft lot, this property boasts 61 feet of water frontage on a wide 75-foot canal, complete with 50 feet of deep water dockage and quick access to the ocean. The backyard is a

Lisa Ferringo

Coldwell Banker Schmitt Lower Keys (KW)

(645) 230-2678

1240 Coury Dr, Key Colony Beach, FL 33051
/27
$35,000 per month
- 4 Beds
- 4.5 Baths
- 5,348 Sq Ft
- House for Rent
133 Severino Dr, Islamorada, FL 33036

Experience luxury living at its finest in this completely renovated four-bedroom, four-bathroom home nestled in one of the most prestigious neighborhoods in the upper Keys. This stunning residence showcases exceptional craftsmanship by a renowned local builder, creating an extraordinary retreat where sophisticated design meets tropical paradise. The home features two separate living areas and

Pete Riveiro The Firm Realty Group

133 Severino Dr, Islamorada, FL 33036
/20
$1,200,000 Sold Apr 23, 2025

411 + 415 1st St, Big Coppitt, FL 33040
- 5 Beds
- 5 Baths
- 2,377 Sq Ft
- Built 1996
Last Sold Summary
- 7% Below List Price
- $505/SF
- 111 Days On Market
Last Listing Agent Christopher Scott,PA Expert Realty LLC (HQ)

411 + 415 1st St, Big Coppitt, FL 33040

/17
Not Listed For Sale
Lot 9 Avenida Primiceria, Marathon, FL 33050

Lot 9 Avenida Primiceria, Marathon, FL 33050

/98
$23,900,000
- 4 Beds
- 6 Baths
- 6,532 Sq Ft
19 Sunset Key Dr, Key West, FL 33040

A truly one-of-one legacy estate set on Sunset Key, one of the most coveted and private islands in the Florida Keys. Just minutes by boat from Key West, this extraordinary waterfront residence offers unmatched privacy, scale, and architectural distinction.Positioned on nearly an acre and the largest homesite on the island, this classically inspired estate was designed by a renowned Naples-based

Pierre Bellion

Ocean Sotheby's International Realty

(786) 980-9721

19 Sunset Key Dr, Key West, FL 33040
/36
$1,500 per month
- 1 Bed
- 1 Bath
- 450 Sq Ft
- Apartment for Rent
195 Gardenia St Unit 4, Tavernier, FL 33070

Great unit part of a unique canal front property in the heart of the Florida Keys, nestled in the sought-after Plantation Key Colony neighborhood. There is 30ft of dock space available for an additional monthly fee. The unit comes unfurnished. Water/Sewer/Trash are included. Coin Washer/Dryer on premises. Located just minutes from marinas, dining, and shopping. Sorry no pets.

Ada Rodriguez Better Homes and Gardens Real Estate Destinations

195 Gardenia St Unit 4, Tavernier, FL 33070
/27
$300,000 Sold Nov 26, 2025

27983 Snapper Ln, Little Torch Key, FL 33042
- 2 Beds
- 1 Bath
- 672 Sq Ft
- Built 1987
Last Sold Summary
- 9% Below List Price
- $446/SF
- 60 Days On Market
Last Listing Agent Sandra Dolowy KeyIsle Realty

27983 Snapper Ln, Little Torch Key, FL 33042

/2
Not Listed For Sale
Lot 8 Avenida Primiceria, Marathon, FL 33050

Lot 8 Avenida Primiceria, Marathon, FL 33050

/94
$1,843,643
- 3 Beds
- 3 Baths
- 2,625 Sq Ft
28 Center Ln, Key Largo, FL 33037

Fall in love with this amazing house that was completely renovated in 2016 with impact windows and doors. Floors throughout premium waterproof plank. Open concept kitchen with island, granite counter tops and SS appliances. 4 bedrooms and 4 baths. (2 masters) This house has plenty, an attic that could be your kids play room. Swim all year round in huge pool with spa and heated Salt Water Pool

Roberto Castillo

Century 21 World Connection

(786) 758-5876

28 Center Ln, Key Largo, FL 33037
/27
$4,900 per month
- 3 Beds
- 2.5 Baths
- 1,804 Sq Ft
- House for Rent
94825 Overseas Hwy Unit 237, Key Largo, FL 33037

Only at Key Largo Ocean Resort can you be close to the bay and minutes from all. Your 1800+ ft luxury vacation property has been meticulously and elegantly presented with dramatic large living spaces, fabulous Chef’s kitchen, tile floors thru-out with lux master and spa bath. All-inclusive and fully equipped in every way imaginable with the best of everything to enjoy true resort style living.

Gustavo Lopez Village Realty of S. Florida

94825 Overseas Hwy Unit 237, Key Largo, FL 33037
/61
$2,550,000 Sold Jan 30, 2026

3620 Sunrise Dr, Key West, FL 33040
- 3 Beds
- 2 Baths
- 1,841 Sq Ft
- Built 1963
Last Sold Summary
- 4% Below List Price
- $1,385/SF
- 17 Days On Market
Last Listing Agent Zainya Zimmerer Berkshire Hathaway HomeServices Knight & Gardner Realty

3620 Sunrise Dr, Key West, FL 33040

/22
Est $1,408,238 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,550 Sq Ft
800 Fleming St Unit C1, Key West, FL 33040

800 Fleming St Unit C1, Key West, FL 33040

/60
$490,000
- 2 Beds
- 1 Bath
- 667 Sq Ft
701 Spanish Main Dr Unit 602, Cudjoe Key, FL 33042

Oceanfront Paradise Awaits!Unit 602 in Venture OutExperience the epitome of Florida living in this charming Two-bedroom, one-bathroom mid-rise mobile home nestled within an exclusive gated community.This beautiful canal front home with ocean views from the backyard home boasts:* Prime Canal front Location: Enjoy breathtaking ocean views and direct access to the water from your private 35 ft

Ian Calderwood

Bluescape Real Estate

(786) 981-9841

701 Spanish Main Dr Unit 602, Cudjoe Key, FL 33042
/42
$3,500 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. Panoramic open water views and direct access to the Florida Keys Bay. This community is your gateway to endless adventure and relaxation with activities like children playground, tennis & basketball court, pool and boat ramp & dock. The

Jose Vigo RE/MAX All Keys Real Estate

325 Calusa St Unit 320, Key Largo, FL 33037
/23
$650,000 Sold Dec 30, 2025

129 S Rd, Upper Matecumbe Key Islamorada, FL 33036
- 2 Beds
- 1 Bath
- 882 Sq Ft
- Built 1958
Last Sold Summary
- 27% Below List Price
- $737/SF
- 118 Days On Market
Last Listing Agent Wiebke Westedt LoKation Real Estate

129 S Rd, Upper Matecumbe Key Islamorada, FL 33036

/2
Est $515,116 Not Listed For Sale
- 2 Beds
- 2 Baths
- 804 Sq Ft
3930 S Roosevelt Blvd Unit W410, Key West, FL 33040

3930 S Roosevelt Blvd Unit W410, Key West, FL 33040

/66
$799,000
- 2 Beds
- 2 Baths
- 842 Sq Ft
701 Spanish Main Dr Unit 172, Cudjoe Key, FL 33042

Canal Front Oasis w/ Ocean Views & Resort Amenities | Income Producing Gem Escape to your own slice of paradise in the highly sought-after, gated resort community of Venture Out on Cudjoe Key! This stunning 2-bedroom, 2-bathroom high-rise home offers the ultimate Florida Keys lifestyle, combining tranquil canal-front living with breathtaking ocean views and an incredible array of world-class

Ian Calderwood

Bluescape Real Estate

(786) 841-6970

701 Spanish Main Dr Unit 172, Cudjoe Key, FL 33042
/44
$5,800 per month
- 3 Beds
- 3 Baths
- 1,300 Sq Ft
- Property for Rent
228 Orchid St, Tavernier, FL 33070

Introducing a 3/2 home located in the serene Tavernier. this hideaway is situated in a tranquil block with only a few properties providing you with the perfect opportunity to comfort of a home with a fully furnished open plan living area, well-equipped kitchen, the location is unbeatable, the property is walking distance, to the mall, and hospital,all local shops, supermarkets. Make the most

Iliana Hernandez Urban Investments Realty LLC

228 Orchid St, Tavernier, FL 33070
/101
$4,700,000 Sold Feb 21, 2025

29433 Enterprise Ave, Big Pine Key, FL 33043
- 4 Beds
- 5 Baths
- 3,727 Sq Ft
- Built 2007
Last Sold Summary
- 6% Below List Price
- $1,261/SF
- 25 Days On Market
Current Estimated Value $4,750,677

Last Listing Agent Lisa Swanson The Agency Florida Keys

29433 Enterprise Ave, Big Pine Key, FL 33043

/32
Not Listed For Sale
- 3 Beds
- 3 Baths
- 1,680 Sq Ft
84745 Old Hwy Unit 11, Islamorada, FL 33036

84745 Old Hwy Unit 11, Islamorada, FL 33036

/43
$1,950,000
- 2 Beds
- 2 Baths
- 1,244 Sq Ft
1514 Shaw Dr, Key Largo, FL 33037

Welcome to Paradise! this home sits on almost 3/4 of an acre along a direct access canal with 100 ft of waterfront, a turning basin and neighborhood only boat ramp with no HOA! Want to park your RV and Boat under your home, done! Want to build your own luxury oasis, here you go. Want to just enjoy easy access to open water and majestic Sunsets from your private observation deck, got that covered!

Andrew Burr

The Keyes Company

(786) 788-7327

1514 Shaw Dr, Key Largo, FL 33037
/42
$5,490 per month
- 2 Beds
- 2 Baths
- 816 Sq Ft
- House for Rent
31547 Avenue D, Big Pine Key, FL 33043

Come see this immaculate 2 Bedroom 2 Bath Big Pine Key Waterfront home with its Wonderful Water Views! It is available for a seasonal rental, so come on down and enjoy the Florida winter weather! It has a well equipped kitchen for your convenience and is only 5 years old. Please see the attached photos. You'll be glad you did! Only 30 miles to Key West and all of the other Points of Interest in

Philip Vias LoKation

31547 Avenue D, Big Pine Key, FL 33043
/2
$55,000 Sold Oct 22, 2025

Lot 2 Rainbow Beach, Big Torch Key, FL 33042
- Land
Last Sold Summary
- 4% Below List Price
- 2 Days On Market
Last Listing Agent Pamela Stangler Expert Realty LLC

Lot 2 Rainbow Beach, Big Torch Key, FL 33042

/28
Not Listed For Sale
130 Overseas Hwy, Islamorada, FL 33036

130 Overseas Hwy, Islamorada, FL 33036

/55
$1,500,000 Under Contract
- 3 Beds
- 2 Baths
- 1,467 Sq Ft
21855 & 21865 Spain Blvd, Cudjoe Key, FL 33042

Majestically positioned at the end of Spain Blvd, within the Prestigious Cudjoe Acres neighborhood. Discover 21855 & 21865 Spain Blvd. A Property that offers the kind of privacy that's almost impossible to find in the Florida Keys. Set on over 3 acres of land, this one-of-a-kind property is surrounded by naturally occurring native plants, mature trees, and freshwater ponds that encourage local

Matthew Sheehan

Ocean Sotheby's International Realty

(866) 528-5667

21855 & 21865 Spain Blvd, Cudjoe Key, FL 33042
/57
$14,000 per month
- 5 Beds
- 4 Baths
- 6,252 Sq Ft
- Apartment for Rent
112 Avenue D Unit 1, Marathon, FL 33050

Experience coastal living at its finest in this brand-new luxury home in the heart of Marathon, Florida. Blending modern elegance with island charm, this residence offers 110 feet of direct water frontage and immediate ocean access, perfect for boating, fishing, and soaking in the views. Enjoy an open-concept layout with designer finishes, a chef’s kitchen with quartz countertops and premium

Andres Cepero Element Real Estate Group

112 Avenue D Unit 1, Marathon, FL 33050
/27
$492,000 Sold Mar 03, 2025

115 Harbor Dr, Key Largo, FL 33037
- 2 Beds
- 1 Bath
- 1,046 Sq Ft
- Built 1955
Last Sold Summary
- 9% Below List Price
- $470/SF
- 75 Days On Market
Current Estimated Value $540,076

Last Listing Agent Christy Hughes Coldwell Banker Schmitt Islamorada

115 Harbor Dr, Key Largo, FL 33037

/2
Not Listed For Sale
- 2 Beds
- 1 Bath
- 672 Sq Ft
170 Mars Ln, Key West, FL 33040

170 Mars Ln, Key West, FL 33040

/29
$1,195,000
- 3 Beds
- 2 Baths
- 1,052 Sq Ft
2911 Seidenberg Ave, Key West, FL 33040

Welcome to your dream home in the heart of Key West's MidTown!This beautifully updated 3-bedroom, 2-bathroom residence blends modern comfort with island charm. Step inside to a spacious, open-concept living area designed for both relaxing and entertaining.The true highlight is the private backyard oasis -- featuring a sparkling pool surrounded by fresh tropical landscaping, an expansive deck, and

Terrance Sullivan

Ocean Sotheby's International Realty

(786) 656-0924

2911 Seidenberg Ave, Key West, FL 33040
/9
$2,500 per month
- 2 Beds
- 1 Bath
- 875 Sq Ft
- Apartment for Rent
184 Adobe Casa Court Dr Unit 184, Tavernier, FL 33070

Find your perfect Keys retreat in this fully renovated 2-bedroom, 1-bath home in the heart of Tavernier. Bright, breezy, and beautifully updated, this property offers open living spaces, a modern kitchen, and a fresh contemporary bath. Step outside and enjoy tropical landscaping, nearby water access, and everything the Upper Keys has to offer—great dining, diving, and sunsets just minutes away.

George Daniel Brokers International Realty LLC

184 Adobe Casa Court Dr Unit 184, Tavernier, FL 33070
/19
$315,000 Sold Dec 05, 2025

201 Coppitt Rd Unit 106, Key West, FL 33040
- 1 Bed
- 1 Bath
- 536 Sq Ft
- Built 1974
Last Sold Summary
- 3% Below List Price
- $588/SF
- 14 Days On Market
Last Listing Agent Jaime Caballero Key West Vacation Properties & Realty, LLC (KW)

201 Coppitt Rd Unit 106, Key West, FL 33040

/22
Est $837,654 Not Listed For Sale
- 2 Beds
- 1 Bath
- 580 Sq Ft
620 Thomas St Unit 286, Key West, FL 33040

620 Thomas St Unit 286, Key West, FL 33040

/37
$969,000 Under Contract
- 4 Beds
- 4 Baths
- 2,216 Sq Ft
3357 Flagler Ave, Key West, FL 33040

Experience the essence of island living in this light-filled, 4-bedroom, 4-bath retreat designed for those who love space, connection to the outdoors, and effortless entertaining. The expansive open-concept layout welcomes you with a bright living room surrounded by sliding glass doors that frame views of the private pool and lush tropical landscape -- the perfect backdrop for game days, family

Bernice Schafer

Vested Palm Real Estate and Home Services

(786) 981-9073

3357 Flagler Ave, Key West, FL 33040
/11
$3,000 per month
- 2 Beds
- 2 Baths
- 630 Sq Ft
- Property for Rent
65821 Overseas Hwy Unit 105, Long Key, FL 33001

6+/- Month Rental--Come Fall in Love with this Little Gem nestled in the heart of Outdoor Resort. This vibrant gated community waterfront resort sits on 35 acres and has multiple amenities such as Pool, marina, boat ramp, boat trailer storage, private beach, bocce ball, tennis courts, club house, Laundry Facilities and more! Whether you're seeking relaxation or recreation, this resort has it

Tracey Petrusha Venture Realty Group

65821 Overseas Hwy Unit 105, Long Key, FL 33001
/23
$850,000 Sold Oct 31, 2025

308 Peacon Ln, Key West, FL 33040
- 3 Beds
- 3 Baths
- 1,296 Sq Ft
- Built 1923
Last Sold Summary
- 43% Below List Price
- $656/SF
- 299 Days On Market
Current Estimated Value $856,223

Last Listing Agent Vic Musmanno Coldwell Banker Schmitt Real Estate Co. (KW)

308 Peacon Ln, Key West, FL 33040

/44
Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,232 Sq Ft
81200 Overseas Hwy Unit 5, 6, Islamorada, FL 33036

81200 Overseas Hwy Unit 5, 6, Islamorada, FL 33036

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