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
/32
$4,250 per month
- 2 Beds
- 2 Baths
- 1,220 Sq Ft
- Property for Rent
14 S Exuma Rd, Key Largo, FL 33037

MODERN PRIVATE TROPICAL RESORT WITH A PRIVATE BEACH AND CANAL FRONTAGE WITH DOCKAGE UP TO 100FT. TAKE A STROLL DOWN TO BUZZARDS ROOST OR SHIPWRECKS ONE OF TWO NEIGHBORHOOD WATERFRONT RESTAURANT/LOUNGE AND ENJOY A FRESH CATCH, A COCKTAIL AND SOME LIVE MUSIC. LOCATED DIRECTLY ON SALTWATER CANAL TO ATLANTIC OCEAN. WHERE YOU WILL ENJOY JOHN PENNEKAMP CORAL REEF STATE PARK ONE OF THE BEST REEF SYSTEMS

Karl Helbig Sunreal Estate Inc.

14 S Exuma Rd, Key Largo, FL 33037
/44
$2,595,000 Sold Nov 13, 2025

628 William St, Key West, FL 33040
- 3 Beds
- 3 Baths
- 1,524 Sq Ft
- Built 1928
Last Sold Summary
- 12% Below List Price
- $1,703/SF
- 9 Days On Market
Last Listing Agent Paige Bethel Island Home Realty Inc.

628 William St, Key West, FL 33040

/34
Est $671,404 Not Listed For Sale
- 2 Beds
- 2 Baths
- 900 Sq Ft
25 Sadowski Causeway, Key Colony Beach, FL 33051

25 Sadowski Causeway, Key Colony Beach, FL 33051

/47
$6,995,000 Under Contract
- 5 Beds
- 6 Baths
- 4,279 Sq Ft
326 Caroline St, Key West, FL 33040

GRAND KEY OASIS is the epitome of luxurious island living, featuring two separate homes connected by a covered pavilion. This fabulous compound is being offered fully furnished with the main house just completely redecorated at a cost of over $100,000. The interior design will leave you marveling at the attention to detail and the sheer luxury of every room. You'll notice from the moment you

Christopher Santry

Last Key Realty, Inc (KW)

(645) 600-8939

326 Caroline St, Key West, FL 33040
/38
$3,600 per month
- 3 Beds
- 2 Baths
- 1,478 Sq Ft
- House for Rent
23 Jenny Ln, Key Largo, FL 33037

Utilities Included! LONG TERM/ANNUAL RENTAL. Unfurnished, 2nd Floor CBS Single Family House, Built 2021, Located @ mm 102/Ocean Side. 3 Spacious Bedroom, 2 Ample Bathrooms, Laundry Room w/Washer & Dryer. Open Concept Living Area with Spacious Kitchen. (Internet & Cable Not Included in Monthly Rent) Move-In Requirements: 1st MO + 2 MO Security Deposit, Complete Landlord's Application, Background &

Alfredo Perez Realty Plus, LLC

23 Jenny Ln, Key Largo, FL 33037
/51
$1,600,000 Sold Apr 08, 2025

174 Westminster Dr, Tavernier, FL 33070
- 3 Beds
- 2 Baths
- 1,648 Sq Ft
- Built 1974
Last Sold Summary
- 7% Below List Price
- $971/SF
- 62 Days On Market
Last Listing Agent Lorie Leal American Caribbean Real Estate, Christie's International Real Estate

174 Westminster Dr, Tavernier, FL 33070

/2
Est $1,121,334 Not Listed For Sale
- 2 Beds
- 3 Baths
- 1,700 Sq Ft
300 El Capitan Dr Unit 2, Islamorada, FL 33036

300 El Capitan Dr Unit 2, Islamorada, FL 33036

/43
$715,000 Pending
- 2 Beds
- 2 Baths
- 841 Sq Ft
500 Burton Dr Unit 5203, Tavernier, FL 33070

Two Oceanfront Balconies comes with this updated 2/2 Condo looking over the Marina & the Atlantic Ocean. U kitchen design with Granite countertops, Stainless Steel appliances & LED dimmer lights. Newer AC under 2 years old with an on demand water heater. Matching tile floors throughout with updated Bathrooms and professionally textured ceilings. Impact sliders and doors. Very Well Kept !! Direct

Tom Rodriguez

American Caribbean Real Estate, Christie's International Real Estate

(786) 983-8357

500 Burton Dr Unit 5203, Tavernier, FL 33070
/41
$2,600 per month
- 2 Beds
- 1.5 Baths
- 808 Sq Ft
- House for Rent
423 Mahogany Ave, Key Largo, FL 33037

Rental available now 2 bed 1.5 baths -Upper level of a large home Vacant Easy to show -Your Ideal Residential Rental Property in Key Largo - All new furniture - upgraded-modern-all you need is here !!! live in paradise for an affordable rate - good for a couple or roommates Experience to live in a nice residential quiet area -Bay side Luxury Living in Key Largo Nestled in a charming residential

isabel linowitz Coldwell Banker Schmitt Key Largo

423 Mahogany Ave, Key Largo, FL 33037
/47
$1,100,000 Sold Jun 27, 2025

21014 7th Ave, Summerland Key, FL 33042
- 3 Beds
- 2 Baths
- 1,361 Sq Ft
- Built 1988
Last Sold Summary
- 19% Below List Price
- $808/SF
- 102 Days On Market
Current Estimated Value $1,093,941

Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

21014 7th Ave, Summerland Key, FL 33042

/2
Not Listed For Sale
510 84th St, Marathon, FL 33050

510 84th St, Marathon, FL 33050

/60
$529,000
- 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
/11
$5,500 per month
- 2 Beds
- 2 Baths
- 1,088 Sq Ft
- House for Rent
237 2nd Rd, Key Largo, FL 33037

The house is open concept, spacious and natural light, comfortable for anyone, it has an air queen bed for extra guests. It has EV charger and RV outlet (NEMA 14-50). All amenities in one place for your comfy stay. Large, screened patio offers the tropical 'out of doors and fresh air' living experience. W/D in unit. Free high-speed Wi-Fi. Walking distance to restaurants, beach boat rentals, and

Abel Acosta Entrust Realty Group Corp

237 2nd Rd, Key Largo, FL 33037
/52
$1,130,000 Sold Feb 05, 2025

1348 Ocean Dr, Summerland Key, FL 33042
- 2 Beds
- 3 Baths
- 930 Sq Ft
- Built 1982
Last Sold Summary
- 7% Below List Price
- $1,215/SF
- 64 Days On Market
Current Estimated Value $1,126,960

Last Listing Agent Jennifer Chaney Chaney Homes

1348 Ocean Dr, Summerland Key, FL 33042

/60
Est $905,992 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,178 Sq Ft
88500 Overseas Hwy Unit 506, Tavernier, FL 33070

88500 Overseas Hwy Unit 506, Tavernier, FL 33070

/66
$849,000
- 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
/66
$3,400 per month
- 4 Beds
- 3 Baths
- 1,944 Sq Ft
- Property for Rent
945 Plantation Rd, Key Largo, FL 33037

Beautifully decorated Key Largo rental! Spacious 4 bed, 3 bath manufactured home featuring two primary suites, wood floors, washer/dryer room, and an open layout with multiple living areas. The kitchen offers stainless steel appliances, an eat-in area, and separate dining room. Enjoy a cozy sitting room, nautical decor, and plenty of space for a large family. Outdoor living includes an open patio

Rogelio Lucas Stratwell, LLC

945 Plantation Rd, Key Largo, FL 33037
/32
$700,000 Sold May 14, 2025

226 Newfound Blvd, Big Pine Key, FL 33043
- 2 Beds
- 2 Baths
- 960 Sq Ft
- Built 1990
Last Sold Summary
- 3% Below List Price
- $729/SF
- 17 Days On Market
Current Estimated Value $706,339

Last Listing Agent Madeleine Lowe Expert Realty LLC (HQ)

226 Newfound Blvd, Big Pine Key, FL 33043

/43
Est $642,911 Not Listed For Sale
- 2 Beds
- 2 Baths
- 826 Sq Ft
500 Burton Dr Unit 2212, Tavernier, FL 33070

500 Burton Dr Unit 2212, Tavernier, FL 33070

/55
$1,500,000
- 3 Beds
- 2 Baths
- 1,467 Sq Ft
21865 Spain Blvd, Summerland 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

(645) 215-8837

21865 Spain Blvd, Summerland Key, FL 33042
/28
$4,700 per month
- 2 Beds
- 2 Baths
- 1,768 Sq Ft
- House for Rent
314 Loeb Ave, Key Largo, FL 33037

Light and Bright, this home has a modern open floor plan. Located on a clean canal with easy boating access. Inside the home features 2 bedroom, 2 full baths and a den, which can be used as either an office/study or as an additional bedroom. Wood floors run throughout the living room and hallway, with tile flooring in the kitchen and plush carpeting in the bedrooms. The master suite has a

Linda Gaunaurd Century 21 Circle- Islamorada

314 Loeb Ave, Key Largo, FL 33037
/54
$950,000 Sold Aug 01, 2025

65821 Overseas Hwy #287 & 288, Long Key, FL 33001
- Land
- 0.04 Acre
- $21,590,909 per Acre
Last Sold Summary
- 40% Below List Price
- 58 Days On Market
Last Listing Agent Sam Fugina Marlin Realty Inc

65821 Overseas Hwy #287 & 288, Long Key, FL 33001

/19
Est $610,641 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,070 Sq Ft
3930 S Roosevelt Blvd Unit S208, Key West, FL 33040

3930 S Roosevelt Blvd Unit S208, 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,

Terrance Sullivan

Ocean Sotheby's International Realty

(786) 656-0924

2911 Seidenberg Ave, Key West, FL 33040
/38
$2,850 per month
- 3 Beds
- 2 Baths
- 1,791 Sq Ft
- Property for Rent
922 S Silver Cir, Key Largo, FL 33037

''SUPER SPACIOUS'' AND IN READY TO MOVE IN CONDITION. THIS 3/2 HOME LOCATED IN SILVER SHORES AN ''OVER 55'' FULLY GATED COMMUNITY. YOU WILL BE AMAZED AT THE SIZE OF THIS HOME WITH PLENTY OF STORAGE AND AN INDOORS LAUNDRY ROOM FOR YOUR CONVENIENCE... UPDATED TO INCLUDE KITCHEN, FLOORS, BATHROOMS AND MORE. HOME IS LOCATED NEAR THE END OF A VERY QUIET STREET. SILVER SHORES COMMUNITY OFFERS A

Alicia Lozano Lokation Real Estate - Tavernier

922 S Silver Cir, Key Largo, FL 33037
/47
$1,400,000 Sold Feb 20, 2025

87851 Old Hwy Unit K36, Islamorada, FL 33036
- 3 Beds
- 2 Baths
- 1,813 Sq Ft
- Built 1989
Last Sold Summary
- 6% Below List Price
- $772/SF
- 66 Days On Market
Current Estimated Value $1,439,029

Last Listing Agent Cynthia Hughes Ocean Sotheby's International Realty

87851 Old Hwy Unit K36, Islamorada, FL 33036

/32
Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,650 Sq Ft
1998 Overseas Hwy Unit A1, Marathon, FL 33050

1998 Overseas Hwy Unit A1, Marathon, FL 33050

/37
$998,000 Open Fri 12PM - 3PM
- 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
/18
$2,600 per month
- 2 Beds
- 1 Bath
- 768 Sq Ft
- House for Rent
333 Bay View Ave, Key Largo, FL 33037

This recently remodeled single-family home features a spacious open-concept layout with 2 bedrooms and 1 bathroom. As a long-term tenant, you may have the opportunity to become a member of the homeowner's park—offering access to a private beach, boat ramp, and dock, perfect for enjoying serene waterfront living and breathtaking sunsets.

Rodolfo Sardina Seaside Realty LLC

333 Bay View Ave, Key Largo, FL 33037
/40
$1,340,000 Sold Jul 09, 2025

1911 Fogarty Ave, Key West, FL 33040
- 2 Beds
- 2 Baths
- 1,195 Sq Ft
- Built 1953
Last Sold Summary
- 8% Below List Price
- $1,121/SF
- 14 Days On Market
Current Estimated Value $1,319,517

Last Listing Agent Brenda Donnelly Brenda Donnelly Real Estate LLC

1911 Fogarty Ave, Key West, FL 33040

/33
Est $933,344 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,350 Sq Ft
28120 County Rd, Little Torch Key, FL 33042

28120 County Rd, Little Torch Key, FL 33042

/35
$1,348,000
- 3 Beds
- 2 Baths
- 1,536 Sq Ft
415 Big Pine Rd, Key Largo, FL 33037

Island Charm Meets Deep-Water Convenience -- Best-Priced Canal Front Home with 60' of Dock!Discover true Keys tropical living in this beautifully updated 2-bedroom, 2-bath canal-front retreat offering 60 feet of concrete dockage, a boat lift, and instant deep-water access. No long idle zones--just cruise straight out to the open bay for unforgettable sunsets, world-class fishing, and the calm

Terry Canto

American Caribbean Real Estate, Christie's International Real Estate

(645) 231-3174

415 Big Pine Rd, Key Largo, FL 33037
/21
$3,200 per month
- 2 Beds
- 2 Baths
- House for Rent
148 Sunrise Dr, Tavernier, FL 33070

Spacious 2/2 in Tavernier Cove. Close to schools, Tavernier Town Center, and between Key Largo and Islamorada. Fully Furnished turn key property. Landscaping included. Impact windows and doors and cement construction make this home safe and secure! F/L/S for move in. 1 small dog is welcome with owners approval. Background and credit check required for approval. Call now to schedule a showing!

Kenneth Smith American Caribbean Real Estate, Christie's International Real Estate

148 Sunrise Dr, Tavernier, FL 33070
/22
$295,000 Sold Oct 24, 2025

201 Coppitt Rd Unit 102, Key West, FL 33040
- 1 Bed
- 1 Bath
- 536 Sq Ft
- Built 1974
Last Sold Summary
- $550/SF
- 54 Days On Market
Last Listing Agent Jimmy Lane Island Life Realty Experts

201 Coppitt Rd Unit 102, Key West, FL 33040

/2
Est $1,094,432 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,404 Sq Ft
17277 Dolphin St E, Summerland Key, FL 33042

17277 Dolphin St E, Summerland Key, FL 33042

/61
$2,250,000
- 3 Beds
- 2 Baths
- 1,674 Sq Ft
743 Pattison Dr, Summerland Key, FL 33042

Welcome to your slice of paradise in the Florida Keys! This stunning 3-bedroom, 2-bath canal-front home in desirable Cudjoe Gardens celebrates everything we love about island life -- in shades of blue. From the moment you arrive, you'll feel the calm, coastal vibe this home radiates.Beautifully remodeled in 2021 with full permits, this residence offers an open-concept living area with soaring

Sandra Tuttle

Island Welcome Real Estate

(786) 756-9163

743 Pattison Dr, Summerland Key, FL 33042
/23
$5,000 per month
- 3 Beds
- 2 Baths
- 1,320 Sq Ft
- Property for Rent
28 Whistling Duck Ln, Key West, FL 33040

Bright and spacious 3-bedroom, 2-bathroom home perfectly situated in the Key West Golf Club community. Overlooking the 9th hole, this property offers a peaceful setting in one of the most desirable parts of the neighborhood, with plenty of parking available.The home is offered unfurnished, with no utilities included, giving you the flexibility to make it your own. One bedroom is downstairs with

Everett Watkins Keller Williams Key West Compass Realty

28 Whistling Duck Ln, Key West, FL 33040
/15
$226,500 Sold Apr 03, 2025

915 S Emerald Dr, Key Largo, FL 33037
- 2 Beds
- 2 Baths
- 1,316 Sq Ft
- Built 1979
Last Sold Summary
- 43% Below List Price
- $172/SF
- 119 Days On Market
Last Listing Agent Ronda Thompson Coldwell Banker Schmitt Key Largo

915 S Emerald Dr, Key Largo, FL 33037

/53
Est $317,907 Not Listed For Sale
- 2 Beds
- 1 Bath
325 Calusa St Unit 506, Key Largo, FL 33037

325 Calusa St Unit 506, Key Largo, FL 33037

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