Monroe County, FL Homes

/30
$1,275,000
- 3 Beds
- 2 Baths
- 1,826 Sq Ft
1221 20th St, Key West, FL 33040

This spacious 3-bedroom, 2-bathroom home is ideal for entertaining and perfectly suited for large family gatherings. Nestled on an oversized, fully fenced corner lot, this tropical oasis features a sparkling saltwater pool, an enclosed garage, and gated parking in the front. A second gated entrance at the rear provides additional space for extra vehicles, an RV, boat, or trailer. The garage also

Jennifer Newman

Truman & Co. (KW)

(645) 900-1825

1221 20th St, Key West, FL 33040
/12
$2,850 per month
- 2 Beds
- 1 Bath
- 960 Sq Ft
- House for Rent
9 Bonita Ave, Key Largo, FL 33037

Charming 2-bedroom, 1-bath elevated home in Key Largo available for long-term lease starting March 1. The home features in-unit laundry, great parking, and a spacious fenced backyard. Small pets will be considered. Utilities are included in the monthly rent.

Courtney Jeffers Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

9 Bonita Ave, Key Largo, FL 33037
/42
$699,000 Sold Mar 27, 2025

29162 Camellia Ln, Big Pine Key, FL 33043
- 3 Beds
- 2 Baths
- 1,218 Sq Ft
- Built 1990
Last Sold Summary
- $574/SF
- 11 Days On Market
Current Estimated Value $702,368

Last Listing Agent Beata Sharpe Coldwell Banker Vanguard Realty

29162 Camellia Ln, Big Pine Key, FL 33043

/63
Est $2,002,545 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,366 Sq Ft
17057 Bonita Ln W, Sugarloaf Key, FL 33042

17057 Bonita Ln W, Sugarloaf Key, FL 33042

/34
$625,000
- 3 Beds
- 2 Baths
- 1,288 Sq Ft
27940 Lobster Tail Trail, Summerland Key, FL 33042

Discover one of the best waterfront buying opportunities in the Lower Keys! This spacious and well-maintained 3-bedroom, 2-bath manufactured home offers incredible value and lifestyle at just $650,000. Inside, you'll find an open floor plan with updated laminate floors, a bright kitchen, and a large primary suite featuring a big bedroom and a relaxing bath with a soaking tub.Outdoors, enjoy 46

Sandra Tuttle

Island Welcome Real Estate

(645) 218-8749

27940 Lobster Tail Trail, Summerland Key, FL 33042
/12
$2,950 per month
- 1 Bed
- 1 Bath
- 700 Sq Ft
- Condo for Rent
1209 Pearl St Unit upstairs, Key West, FL 33040

Lovely upstairs loft style apartment available now for LONG TERM.Located in upper old town Key West, near Bayview Park. Apartment is completely furnished, private full size W/D, gas range, large tiled shower, and covered deck for tropical outside living! All utilities and internet are included in rent! First and last mo rent required to move in. Property is very well maintained, and

1209 Pearl St Unit upstairs, Key West, FL 33040
/31
$750,000 Sold Oct 03, 2025

1428 Virginia St, Key West, FL 33040
- 4 Beds
- 2 Baths
- 2,236 Sq Ft
- Built 1933
Last Sold Summary
- 16% Below List Price
- $335/SF
- 111 Days On Market
Current Estimated Value $857,369

Last Listing Agent Walt Lee Berkshire Hathaway HomeServices Knight & Gardner Realty

1428 Virginia St, Key West, FL 33040

/2
Est $718,842 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,440 Sq Ft
151 Atlantic Ave, Tavernier, FL 33070

151 Atlantic Ave, Tavernier, FL 33070

/15
$2,899,000
- Land
94 Sunrise Dr, Marathon, FL 33050

Build your dream oceanfront home in the prestigious gated community of Sunrise Isle, a coastal island of just 20 properties located next to beautiful Sombrero Beach in the heart of Marathon. Build anytime you like as the property comes with a deeded City of Marathon Transferrable Building Right subject to the conditions of the City of Marathon. Generous 40,249 sq. ft. ocean and canal front lot (a

Lisa Ferringo

Coldwell Banker Schmitt Lower Keys (KW)

(786) 572-0195

94 Sunrise Dr, Marathon, FL 33050
/68
$7,500 per month
- 4 Beds
- 5 Baths
- 2,432 Sq Ft
- House for Rent
1516 Aqueduct Ln, Key Largo, FL 33037

Discover coastal living at its finest! This exceptional 4-bed, 3.2-bath canal-front home right next to Adams cut offers over 2,400 sq ft of beautifully designed living space with stunning bay views from wrap-around balconies and a rooftop terrace. Thoughtfully appointed with an elevator, indoor and outdoor kitchens, laundry room, and spacious layouts, this residence is ideal for entertaining and

Kristal Rivera Diaz LPT Realty, LLC

1516 Aqueduct Ln, Key Largo, FL 33037
/33
$785,000 Sold Apr 03, 2025

64 Sombrero Beach Rd, Marathon, FL 33050
- Land
Last Sold Summary
- 45% Below List Price
- 183 Days On Market
Current Estimated Value $962,664

Last Listing Agent Monica Barrett Coldwell Banker Schmitt Real Estate Co.

64 Sombrero Beach Rd, Marathon, FL 33050

/6
Est $2,222,715 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,154 Sq Ft
241 Pueblo St, Tavernier, FL 33070

241 Pueblo St, Tavernier, FL 33070

/25
$979,900
- 4 Beds
- 2 Baths
- 1,943 Sq Ft
160 Ridge St, Tavernier, FL 33070

Beautiful corner-lot CBS home in the heart of Plantation Key. This 4-bedroom, 2-bath residence offers 1,964 sq. ft. of living space and is located in the desirable X flood zone. Notable features include impact windows and doors, a spacious open floor plan, and a bonus family room ideal for entertaining or additional living space.The bright interior is filled with natural light, with a functional

Sandra Spaulding

Coldwell Banker Schmitt Islamorada

(877) 837-0467

160 Ridge St, Tavernier, FL 33070
/7
$2,200 per month
- Studio
- 1 Bath
- 1,000 Sq Ft
- Condo for Rent
1505 White St Unit Efficiency, Key West, FL 33040

This unit is unique at 1505 White large one bedroom and one bathroom, with private mini deck & outdoor bar sink & grillLocated two blocks from ocean 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

1505 White St Unit Efficiency, Key West, FL 33040
/43
$1,300,000 Sold Mar 14, 2025

1050 Gulf Dr, Summerland Key, FL 33042
- 2 Beds
- 2 Baths
- 1,171 Sq Ft
- Built 1985
Last Sold Summary
- 4% Below List Price
- $1,110/SF
- 24 Days On Market
Current Estimated Value $1,323,845

Last Listing Agent Michelle Howerton Brenda Donnelly Real Estate LLC

1050 Gulf Dr, Summerland Key, FL 33042

/42
Est $2,844,828 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 3,139 Sq Ft
80639 Old Hwy Unit 403, Islamorada, FL 33036

80639 Old Hwy Unit 403, Islamorada, FL 33036

/34
$1,595,000
- 3 Beds
- 2 Baths
- 1,667 Sq Ft
22865 Redfish Ln, Summerland Key, FL 33042

The Best Boating Access in the Lower Keys, hands down!!! The 'Island Life' awaits you in this stunning well thought out custom designed canal front property. This solid CBS home, nestled in lush tropical landscaping, features 3 bedrooms and 2 baths on an oversized 10,200 sq.ft. lot located in the tranquil setting of sought after Cudjoe Ocean Shores. This subdivision is extremely desirable due to

Anneliese Dietrick

Coldwell Banker Schmitt Lower Keys (KW)

(645) 241-6029

22865 Redfish Ln, Summerland Key, FL 33042
/6
$1,900 per month
- 1 Bath
- 450 Sq Ft
- Apartment for Rent
103365 Overseas Hwy Unit C, Key Largo, FL 33037

End Unit C Newly Remodeled Studio Apartment featuring all Brand New Black Appliances. Conveniently located close to shopping, schools, restaurants, and more. Move -In Ready.

Tracey Petrusha Venture Realty Group

103365 Overseas Hwy Unit C, Key Largo, FL 33037
/35
$1,675,000 Sold Jun 02, 2025

1075 Duval St Unit 1, Key West, FL 33040
- 2 Beds
- 2.5 Baths
- 1,225 Sq Ft
- Built 1987
Last Sold Summary
- $1,367/SF
- 4 Days On Market
Current Estimated Value $1,676,540

Last Listing Agent Richard Haskins Buy The Keys

1075 Duval St Unit 1, Key West, FL 33040

/3
Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,152 Sq Ft
33 Judy Place, Key Largo, FL 33037

33 Judy Place, Key Largo, FL 33037

/40
$1,300,000 Under Contract
- 3 Beds
- 2 Baths
- 1,422 Sq Ft
537 Heck Ave, Summerland Key, FL 33042

Welcome to island living at its finest. This stunning 3-bedroom, 2-bath canal-front home is packed with every bell and whistle you could want in a Florida Keys retreat. Designed for both comfort and entertaining, the property features a private pool, tiki hut, 3 screened in porches boat lift with direct canal access and close to open water with no bridges. Perfect for days on the water and

Michelle Howerton

Brenda Donnelly Real Estate LLC

(786) 410-6602

537 Heck Ave, Summerland Key, FL 33042
/14
$12,000 per month
- 4 Beds
- 2 Baths
- 2,000 Sq Ft
- House for Rent
309 Calzada de Bougainville, Marathon, FL 33050

4/2 +dock+Pool+tiki bar. State of the art remodeled kitchen features include fully stocked tools. Private pool heater/chiller. Ample parking for cars and boat trailer just steps to Sombrero Beach, Florida. Dock can accommodate large boat 35-45 ft parallel to dock. New full size washer and dryer, new linens, new pillows and upgraded details throughout Home features high speed internet and

309 Calzada de Bougainville, Marathon, FL 33050
/2
$510,000 Sold Sep 08, 2025

Unlisted Address
- 3 Beds
- 2 Baths
- 972 Sq Ft
- Built 1989
Last Sold Summary
- $525/SF
Current Estimated Value $507,857

Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

Unlisted Address

/24
Est $1,845,396 Not Listed For Sale
- 4 Beds
108 S Bahama Dr, Marathon, FL 33050

108 S Bahama Dr, Marathon, FL 33050

/44
$999,000
- 3 Beds
- 3 Baths
- 1,548 Sq Ft
108 Jamaica St, Marathon, FL 33050

Looking for your Florida Keys dream home with space to spread out, soak up the sun, and maybe even tinker with a classic car or two? Welcome to 108 Jamaica Street on Duck Key, a tropical paradise on a double lot with a custom-built CBS home, screened pool, guest house, cistern for watering plants and washing cars, and epic garage. This place was built with love by the current owner and it shows.

Lisa Ferringo

Coldwell Banker Schmitt Lower Keys (KW)

(786) 882-8610

108 Jamaica St, Marathon, FL 33050
/25
$3,500 per month
- 3 Beds
- 3 Baths
- House for Rent
124 S Bay Harbor Dr, Key Largo, FL 33037

Annual Rental - Beautiful 3 Bedroom / 3 Bathroom Elegantly remodeled and fully updated! This charming home comes fully furnished and tastefully decorated, featuring a Above ground decked pool and ample parking & access to private Beach & Boat Ramp. Move-in ready — just bring your toothbrush! Conveniently located close to shopping, schools, restaurants, and more. Perfect for anyone looking for

Tracey Petrusha LoKation

124 S Bay Harbor Dr, Key Largo, FL 33037
/54
$660,000 Sold Nov 12, 2025

500 Burton Dr Unit 4402, Tavernier, FL 33070
- 2 Beds
- 2 Baths
- 826 Sq Ft
- Built 1991
Last Sold Summary
- 8% Below List Price
- $799/SF
- 93 Days On Market
Last Listing Agent Tom Rodriguez American Caribbean Real Estate, Christie's International Real Estate

500 Burton Dr Unit 4402, Tavernier, FL 33070

/30
Not Listed For Sale
- 2 Beds
- 1 Bath
- 470 Sq Ft
81 Tarpon Basin Dr, Key Largo, FL 33037

81 Tarpon Basin Dr, Key Largo, FL 33037

/41
$999,000
- 3 Beds
- 2 Baths
- 1,400 Sq Ft
22954 Buccaneer Ln, Summerland Key, FL 33042

Welcome to 22954 Buccaneer Ln, a quintessential Florida Keys waterfront escape. Perfectly positioned on a rare corner canal lot, this property offers 191 feet of concrete dockage with quick, unobstructed access to open water--ideal for serious boaters. The exterior's inviting Keys-style cedar siding blends seamlessly with lush tropical landscaping, creating a relaxed island vibe from the moment

Lisa Ferringo

Coldwell Banker Schmitt Lower Keys (KW)

(645) 230-1509

22954 Buccaneer Ln, Summerland Key, FL 33042
/18
$5,900 per month
- 2 Beds
- 1.5 Baths
- 850 Sq Ft
- Townhouse for Rent
634 Louisa St, Key West, FL 33040

Newly Renovated Townhome in Prime Old Town Key West located just 3 blocks from the beach! Experience the best of island living in this beautifully renovated 2-bedroom, 1.5-bath end-unit townhouse, perfectly situated in one of Key West's most sought-after neighborhoods. Features include a stunning new kitchen with quartz countertops, custom cabinetry, stainless steel appliances, and a handcrafted

634 Louisa St, Key West, FL 33040
/18
$750,000 Sold Jun 17, 2025

214 Golf Club Dr, Key West, FL 33040
- 2 Beds
- 3 Baths
- 1,120 Sq Ft
- Built 2000
Last Sold Summary
- 19% Below List Price
- $670/SF
- 376 Days On Market
Current Estimated Value $812,730

Last Listing Agent Jaime Caballero Key West Vacation Properties & Realty, LLC (KW)

214 Golf Club Dr, Key West, FL 33040

/36
Not Listed For Sale
- 2 Beds
- 2 Baths
- 800 Sq Ft
113 1st Ct, Key Largo, FL 33037

113 1st Ct, Key Largo, FL 33037

/38
$899,000
- 3 Beds
- 2 Baths
- 1,203 Sq Ft
153 Peg Leg Ln, Summerland Key, FL 33042

Super quick ocean access and 60' of concrete dockage from this 3 Bedroom 2 Bath canal front home located just 2 canals over from open water! Plenty of room for all your toys in the oversized 2-Car Garage with overhead doors on both sides. Inside you will find an open floor plan leading out to a full-length Porch overlooking the water for morning coffee or evening cocktails with family and

Lisa Ferringo

Coldwell Banker Schmitt Lower Keys (KW)

(833) 853-7147

153 Peg Leg Ln, Summerland Key, FL 33042
/8
$1,900 per month
- 1 Bath
- 450 Sq Ft
- Apartment for Rent
103365 Overseas Hwy Unit A, Key Largo, FL 33037

End Unit A Newly Remodeled Studio Apartment featuring Brand New White Appliances. Conveniently located close to shopping, schools, restaurants, and more. Move -In Ready.

Tracey Petrusha Venture Realty Group

103365 Overseas Hwy Unit A, Key Largo, FL 33037
/55
$3,900,000 Sold Sep 16, 2025

442 Palm Dr, Islamorada, FL 33036
- 4 Beds
- 3 Baths
- 2,058 Sq Ft
- Built 1977
Last Sold Summary
- 11% Below List Price
- $1,895/SF
- 179 Days On Market
Current Estimated Value $3,912,881

Last Listing Agent AJ Vetter Palm House Real Estate

442 Palm Dr, Islamorada, FL 33036

/38
Not Listed For Sale
- 3 Beds
- 3 Baths
- 3,255 Sq Ft
Unlisted Address

Unlisted Address

/37
$3,600,000
- 5 Beds
- 6 Baths
- 3,667 Sq Ft
400 Aronovitz Ln, Key West, FL 33040

Discover a rare investment and lifestyle opportunity at 'Zen Villa,' a prestigious compound anchored in the coveted X-Flood Zone of Old Town, Key West. Spanning a spacious 5,891 SF lot, this unique offering encompasses three distinct residences: the luxurious main estate at 400 Aronovitz Lane and two charming, income-generating cottages at 621 and 623 Whitehead Street.The main residence is a

Damian Vantriglia

Berkshire Hathaway HomeServices Knight & Gardner Realty

(786) 699-6375

400 Aronovitz Ln, Key West, FL 33040
/27
$8,759 per month
- 6 Beds
- 2 Baths
- 1,400 Sq Ft
- Condo for Rent
87200 Overseas Hwy Unit E4, Islamorada, FL 33036

Enjoy your 2026 winter, come immerse your body, mind, and soul in soothing waters that surround our Florida Keys paradise. Amazing sandy beaches, sunset fishing pier, new heated pool, and moderized clubhouse.Best community for fun activities! We offer as is bikes, kayaks, and many more amenities. Semi-private backyard. Sleep in 2.5 separate bedrooms, and loft. Nice bedding & towels. 2

87200 Overseas Hwy Unit E4, Islamorada, FL 33036
/39
$750,000 Sold Apr 07, 2025

104500 Overseas Hwy Unit A104, Key Largo, FL 33037
- 2 Beds
- 2 Baths
- 1,282 Sq Ft
- Built 1981
Last Sold Summary
- 4% Below List Price
- $585/SF
- 119 Days On Market
Current Estimated Value $796,254

Last Listing Agent Jamie Engel Coldwell Banker Schmitt Islamorada

104500 Overseas Hwy Unit A104, Key Largo, FL 33037

/45
Not Listed For Sale
- 2 Beds
- 1.5 Baths
- 1,216 Sq Ft
62900 Overseas Hwy, Marathon, FL 33050

62900 Overseas Hwy, Marathon, FL 33050

Showing Results 321 - 360, Page 9 of 18

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