Monroe County, FL Homes

/58
$3,750,000
- 3 Beds
- 2 Baths
- 1,851 Sq Ft
755 & 744 Sawyer Dr, Cudjoe Key, FL 33042

In prestigious Cudjoe Gardens, this fully renovated Keys retreat feels more like a private sanctuary than a house. The main oceanfront lot is wrapped in lush, mature landscaping -- buttonwoods in the back, banyan trees along the side, orchids everywhere, irrigation, and low-voltage lighting that makes the property glow at night. It's the kind of tropical setting people move to the Keys

Terrance Sullivan

Ocean Sotheby's International Realty

(786) 465-7217

755 & 744 Sawyer Dr, Cudjoe Key, FL 33042
/33
$4,950 per month
- 4 Beds
- 2 Baths
- 1,998 Sq Ft
- House for Rent
235 Anne Bonny Dr, Key Largo, FL 33037

Stunning Bay & Wide Canal Views Surround This 4 Bedroom 2 Bathroom With 2 Separate Entrances Exceptional Waterfront Home!!! With a 50 Ft. Concrete Dock!!! Upstairs: 2 Bedrooms 1 Bathroom, Kitchen, Laundry 1000 ft.2 Downstairs: 2 Bedrooms 1 Bathroom, Kitchen, Laundry 1000 ft.2 Enjoy this beautiful home on a deep wide canal with gorgeous bay views in the prestigious Pirates Cove neighborhood, share

Milena Wood Barrios and Associates Realty

235 Anne Bonny Dr, Key Largo, FL 33037
/39
$200,000 Sold Nov 25, 2025

1466 Overseas Hwy Unit 5, Marathon, FL 33050
- Built 1975
Last Sold Summary
- 11% Below List Price
- 223 Days On Market
Last Listing Agent Joshua Mothner Coldwell Banker Schmitt Real Estate Co.

1466 Overseas Hwy Unit 5, 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

/51
$1,250,000 Open Sun 11AM - 1PM
- 4 Beds
- 3 Baths
- 2,166 Sq Ft
30985 Hibiscus Dr, Big Pine Key, FL 33043

CBS POOL HOME OFFERS 133 ft. along the 50 ft. wide canal, boat davits, a fish cleaning station and quick access to Bogie Channel, the Atlantic and back country. Dock multiple boats along the 60 ft. concrete seawall with the possibility of adding more dockage. The fenced 19,762 sq. ft. double lot provides a private, park-like setting featuring an inviting, heated pool, outdoor shower, grilling

Patti Nickless

Coldwell Banker Schmitt Lower Keys (KW)

(888) 284-4668

30985 Hibiscus Dr, Big Pine Key, FL 33043
/10
$2,800 per month
- 2 Beds
- 1 Bath
- 710 Sq Ft
- Condo for Rent
1220 3rd St Unit UP, Key West, FL 33040

Discover your perfect living space in the heart of new-town Key West. This charming 2-bedroom, 1-bathroom apartment in a quaint 4-plex offers both comfort and convenience. Situated on the upper level, this unit boasts a brand-new deck, perfect for enjoying warm island breezes and outdoor relaxation.Step inside to a spacious living room adorned with high ceilings that create an open and

1220 3rd St Unit UP, Key West, FL 33040
/5
$3,100,000 Sold Feb 14, 2025

1326 W 79th St, Marathon, FL 33050
- 3 Beds
- 2.5 Baths
- 3,613 Sq Ft
- Built 2021
Last Sold Summary
- $858/SF
- 0 Days On Market
Current Estimated Value $3,219,341

Last Listing Agent Kenneth Herzbrun Lokation Real Estate

1326 W 79th St, Marathon, FL 33050

/57
Est $5,591,760 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

/11
$2,950,000
- Land
- 0.5 Acre
- $5,895,128 per Acre
246 & 248 Pescayo Ave, Marathon, FL 33050

Ready to Build Your Dream Florida Keys Estate? This rare opportunity includes two large adjacent, cleared parcels, totaling 21,798 sq ft, in the heart of Marathon, already vested with a City of Marathon Market Rate Transferable Building Right, (TBR) -- meaning no wait, no red tape - start building immediately! Positioned on a deepwater canal with 7.9' controlling depth, this location is ideal for

Joshua Mothner

Coldwell Banker Schmitt Real Estate Co.

(786) 982-6772

246 & 248 Pescayo Ave, Marathon, FL 33050
/21
$3,250 per month
- 2 Beds
- 2 Baths
- 700 Sq Ft
- Property for Rent
3312 Northside Dr Unit 316, Key West, FL 33040

Freshly painted and clean as a whistle, this two bedroom and two bathroom condo is ready for occupancy. Tile floors throughout, central AC with ceiling fans, balcony, and granite countertops. Building has recently gone thru extensive renovations and there is a pool, tennis courts, and parking. Secured building. Sorry, pets aren't allowed. Washer and dryer located across the hall and an external

Jimmy Lane Island Life Realty Experts

3312 Northside Dr Unit 316, Key West, FL 33040
/16
$500,000 Sold Jul 10, 2025

9 7th St, Key Colony Beach, FL 33051
- 2 Beds
- 2 Baths
- 885 Sq Ft
- Built 1966
Last Sold Summary
- $565/SF
- 0 Days On Market
Current Estimated Value $499,133

Last Listing Agent Karen Raspe, PA Ocean Sotheby's International

9 7th St, Key Colony Beach, FL 33051

/42
Est $2,068,741 Not Listed For Sale
- 4 Beds
- 4 Baths
- 2,800 Sq Ft
106 Tequesta St, Tavernier, FL 33070

106 Tequesta St, Tavernier, FL 33070

/50
$1,975,000 Open Sun 1PM - 3PM
- 4 Beds
- 3 Baths
- 1,738 Sq Ft
1015 Eaton St, Key West, FL 33040

1015 Eaton Street, the art of island elegance, where historic soul meets modern sophistication. Four bedrooms. Updated baths. A new kitchen. Natural light everywhere. And a big, resort-style pool; a true rarity in Old Town! Positioned in the coveted heart of Old Key West, just steps from the Historic Seaport, 1015 Eaton Street is more than a home, it's a statement. A refined yet relaxed retreat

Damian Vantriglia

Berkshire Hathaway HomeServices Knight & Gardner Realty

(305) 745-7597

1015 Eaton St, Key West, FL 33040
/12
$1,950 per month
- 2 Beds
- 1 Bath
- 900 Sq Ft
- House for Rent
917 Red Bird Rd, Key Largo, FL 33037

Property located in a very nice and quiet neighborhood with homes that are well kept. Their is a park that has a small boat ramp. From the park which is walking distance from your new home you can fish, launch your kayak or small boat, use the picnic area or simple enjoy the beautiful sunrise. We have central air conditioner, washer and dryer, large pantry, bedrooms with ample closets, covered

917 Red Bird Rd, Key Largo, FL 33037
/61
$700,000 Sold Jun 12, 2025

202 51st St, Marathon, FL 33050
- 2 Beds
- 1 Bath
- 1,053 Sq Ft
- Built 1971
Last Sold Summary
- 12% Below List Price
- $665/SF
- 29 Days On Market
Last Listing Agent Mykael Marinelli American Caribbean Real Estate, Christie's International Real Estate

202 51st St, Marathon, FL 33050

/68
Est $3,165,986 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

/73
$4,699,000
- 3 Beds
- 5 Baths
- 4,000 Sq Ft
58213 Morton St, Marathon, FL 33050

Nestled on a secluded 2-acre lot in Grassy Key, Marathon, this gated waterfront estate boasts 4,000 sq. ft. and is highlighted with a ton of amenities including two docks, 4 post boat lift, private sandy beach and an infinity-edge elevated pool blending seamlessly with the gulf and featuring a built-in table and chairs for relaxing or entertaining. Expansive covered areas by the pool offer shaded

Lisa Ferringo

Coldwell Banker Schmitt Lower Keys (KW)

(786) 751-7833

58213 Morton St, Marathon, FL 33050
/8
$1,850 per month
- 1 Bed
- 1 Bath
- Apartment for Rent
8 Bowen Dr, Key Largo, FL 33037

Bright and updated 1 bedroom / 1 bath apartment now available! This ground-floor unit offers a clean interior, private entry, and an in-unit washer and dryer. The upstairs level is tenant-occupied. Small pets considered. Available for annual rental.

Courtney Jeffers Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

8 Bowen Dr, Key Largo, FL 33037
/19
$470,000 Sold Apr 07, 2025

133 Sunrise Dr, Tavernier, FL 33070
- 2 Beds
- 1.5 Baths
- 1,368 Sq Ft
- Built 1949
Last Sold Summary
- 21% Below List Price
- $344/SF
- 98 Days On Market
Current Estimated Value $563,075

Last Listing Agent Pierre Bellion Ocean Sotheby's International Realty

133 Sunrise Dr, Tavernier, FL 33070

/10
Est $808,630 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,400 Sq Ft
57434 Gibson St, Marathon, FL 33050

57434 Gibson St, Marathon, FL 33050

/23
$325,000
- 2 Beds
- 2 Baths
- 860 Sq Ft
1129 Pebble Beach Ln Unit 11, Marathon, FL 33050

Discover one of the best-priced properties in the Florida Keys! A beautifully updated 2-bedroom, 2-bathroom top-floor condo on sought-after Duck Key. Offering a flexible layout, tasteful upgrades, and a brand-new air-conditioning system, this home delivers comfort and value in equal measure.The main living area features a renovated kitchen with quartz countertops, stainless steel appliances, and

Coby Taylor

Taylor & Assoc. RE, Inc.

(786) 442-3513

1129 Pebble Beach Ln Unit 11, Marathon, FL 33050
/8
$3,950 per month
- 3 Beds
- 2 Baths
- 1,072 Sq Ft
- Condo for Rent
3930 S Roosevelt Blvd Unit N204, Key West, FL 33040

3 BED/ 2BA LAS SALINAS. Long Term Rental 12 mo. With option to renew.UNFURNISHED RENTAL. Photos reflect the home of current tenants who are moving.Open floor plan with pool view. Many updates to the unit. Primary bedroom en-suite.Tenant occupied so a courtesy of 24 hr notice to view property requested.Sorry, no pets per HOA

3930 S Roosevelt Blvd Unit N204, Key West, FL 33040
/30
$930,000 Sold Aug 01, 2025

608 Roberts Ln, Key West, FL 33040
- 2 Beds
- 2 Baths
- 1,700 Sq Ft
- Built 1933
Last Sold Summary
- 41% Below List Price
- $547/SF
- 189 Days On Market
Current Estimated Value $1,276,271

Last Listing Agent Bascom Grooms Bascom Grooms Real Estate (KW)

608 Roberts Ln, Key West, FL 33040

/2
Est $3,151,610 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

/67
$2,395,000
- 4 Beds
- 4 Baths
- 2,390 Sq Ft
3605 Eagle Ave, Key West, FL 33040

3605 Eagle Avenue | Key WestSituated on one of Key West's most desirable streets, this private compound on Eagle Avenue offers a rare combination of space, privacy, and refined island living. Set on a double corner lot totaling 12,000 sq ft, the property is fully enclosed, offering enhanced privacy and a tranquil, resort-like setting.The main residence features 3 bedrooms, 2.5 baths, and

Terrance Sullivan

Ocean Sotheby's International Realty

(786) 981-4184

3605 Eagle Ave, Key West, FL 33040
/56
$5,200 per month
- 2 Beds
- 2.5 Baths
- 1,792 Sq Ft
- Townhouse for Rent
94220 Overseas Hwy Unit 1D, Key Largo, FL 33037

BAYFRONT UNIT - 2 BEDROOM + BOAT SLIP | ANNUAL LEASESunset Hammock is a bayfront Gated community located on Buttonwood Sound, offering a peaceful Florida Keys lifestyle. Building A opens directly onto the bay with no obstructed views and faces due west, delivering some of the most spectacular nightly sunsets you'll find.This well-appointed 2-bedroom 2.5 bath residence is ideal for anyone seeking

Yvette Doherty Coldwell Banker Schmitt Key Largo

94220 Overseas Hwy Unit 1D, Key Largo, FL 33037
/6
$600,000 Sold Dec 01, 2025

101551 Overseas Hwy Unit 57, Key Largo, FL 33037
- Land
Last Sold Summary
- 5% Below List Price
- 8 Days On Market
Last Listing Agent Kelly Randin RE/MAX All Keys Real Estate

101551 Overseas Hwy Unit 57, Key Largo, FL 33037

/53
Est $2,107,715 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

/30
$800,000
- 3 Beds
- 2 Baths
- 1,062 Sq Ft
630 Barry Ave, Summerland Key, FL 33042

Set on a rare 0.68-acre property spanning four lots, this private canal-front home offers exceptional space, water access, and tranquility. With 204.5 feet of canal frontage, a 40-foot wood dock, and less than a 5-minute boat ride to Pine Channel, this location is ideal for boating enthusiasts. The 3-bedroom, 2-bath residence features a roof-covered deck perfect for entertaining friends and

Brenda Thomas

Island Welcome Real Estate

(786) 822-8419

630 Barry Ave, Summerland Key, FL 33042
/14
$2,745 per month
- 2 Beds
- 1 Bath
- 850 Sq Ft
- House for Rent
701 124th Street Gulf, Marathon, FL 33050

GREAT LOCATION IN MARATHONCLEAN CONCRETE GROUND LEVEL HOMEBRIGHT – LIGHT – FRESHLY PAINTED2 BEDROOMS – 1 TILED BATH WITH FULL SIZE TUBEAT IN KITCHEN INCLUDES 2 LARGE SCREEN TV for your useAIR CONDITIONERS PLUS CEILING FANS IN EACH ROOM PARK AT YOUR FRONT DOOR, NO STAIRSPRIVATE ROAD – PRIVATE FENCED YARDACCORDIAN HURRICANE PROTECTIONPRIVATE LAUNDRY ROOMS

701 124th Street Gulf, Marathon, FL 33050
/39
$1,250,000 Sold Apr 22, 2025

401 Calle Limon, Marathon, FL 33050
- 4 Beds
- 2 Baths
- 1,502 Sq Ft
- Built 1981
Last Sold Summary
- 4% Below List Price
- $832/SF
- 229 Days On Market
Current Estimated Value $1,236,518

Last Listing Agent Lisette Martinez Luxe Properties

401 Calle Limon, Marathon, FL 33050

/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

/47
$2,300,000 Open House 2/20
- 3 Beds
- 3 Baths
- 1,690 Sq Ft
1503 Johnson St, Key West, FL 33040

Welcome to 1503 Johnson St, a luxurious Key West retreat now offered for sale--a turnkey residence that truly embodies style, comfort, and effortless island living. This elegant three-bedroom, three-bathroom furnished home is situated on a fully fenced corner lot, offering exceptional privacy while keeping you close to everything the island has to offer. Located just four blocks from the Atlantic

Leslie Howard

Coldwell Banker Schmitt Real Estate Co. (KW)

(877) 692-1660

1503 Johnson St, Key West, FL 33040
/20
$2,500 per month
- 2 Beds
- 2 Baths
- 918 Sq Ft
- Apartment for Rent
913 Lobster Ln, Key Largo, FL 33037

Absolutely adorable 2 bedroom 2 bath residence showcasing classic Florida Keys architecture with a charming Key West vibe. This upstairs unit features beautiful wood floors and a soaring vaulted ceiling in the great room, creating a bright and airy living space, punctuated by a classic fireplace. This home has been artfully updated with modern finishes and stylishly renovated bathrooms, blending

Sally Stribling Coldwell Banker Schmitt Key Largo

913 Lobster Ln, Key Largo, FL 33037
/53
$3,500,000 Sold Aug 08, 2025

407-415 Olivia St, Key West, FL 33040
- 6 Beds
- 5 Baths
- 3,171 Sq Ft
- Built 1964
Last Sold Summary
- 18% Below List Price
- $1,104/SF
- 134 Days On Market
Current Estimated Value $3,599,975

Last Listing Agent Brenda Donnelly Brenda Donnelly Real Estate LLC

407-415 Olivia St, Key West, FL 33040

/62
Est $5,270,213 Not Listed For Sale
- 4 Beds
- 4.5 Baths
- 3,600 Sq Ft
216 Tide Ave, Tavernier, FL 33070

216 Tide Ave, Tavernier, FL 33070

/50
$799,000 Open Sun 10AM - 12PM
- 2 Beds
- 2 Baths
- 912 Sq Ft
1672 Pandorea Ln, Big Pine Key, FL 33043

Discover canal-front living in Eden Pines Colony where local amenities are within easy reach! The owners have maximized this 8,063 sq. ft. property for outdoor living, from the screened sitting and grilling area below, to the lush gardens surrounding the amazing outdoor shower. The inside is bright and airy featuring a wood-planked cathedral ceiling in the great room, an exceptional upgraded

Patti Nickless

Coldwell Banker Schmitt Lower Keys (KW)

(888) 410-2419

1672 Pandorea Ln, Big Pine Key, FL 33043
/63
$3,200 per month
- 2 Beds
- 2 Baths
- 778 Sq Ft
- Condo for Rent
98202 Windward Ave Unit 202 and Boatslip, Key Largo, FL 33037

CONDO W/ BOATSLIP FOR RENT 2/2KEY LARGOEscape to a bayside retreat with this updated 2-bedroom, 2-bathresidence, privately set on the second floor and only steps from the water's edge. A light-filled interior opens to a screened balcony, the perfect spot to unwind while taking in the tropical breeze. What truly sets this property apart is its 30 ft deeded boat slip--a coveted

98202 Windward Ave Unit 202 and Boatslip, Key Largo, FL 33037
/47
$2,100,000 Sold Apr 01, 2025

237 Atlantic Blvd, Key Largo, FL 33037
- 7 Beds
- 4 Baths
- 3,164 Sq Ft
- Built 1980
Last Sold Summary
- 22% Below List Price
- $664/SF
- 273 Days On Market
Current Estimated Value $2,132,226

Last Listing Agent TEAM Walters Gloria, Rachel and Michae Ocean Sotheby's International Realty

237 Atlantic Blvd, Key Largo, FL 33037

/2
Est $819,239 Not Listed For Sale
- 2 Beds
- 1 Bath
- 651 Sq Ft
51 Riviera Dr, Key West, FL 33040

51 Riviera Dr, Key West, FL 33040

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