Monroe County, FL Homes

/69
$1,699,999 Pending
- 3 Beds
- 3 Baths
- 1,827 Sq Ft
126 Columbus Dr, Islamorada, FL 33036

Incoming producing property with future bookings already in place! Beautiful Florida Keys home, 1,827 SqFt living area (larger than tax roll) fully renovated 3 bedroom, 3 bath waterfront property situated in Lower Matecumbe Key with 7,500 SQ FT lot. New seawall was completed and elevated in 2021. Boaters paradise with 75FT of dockage, under 5 minute ride to open ocean + easy access to bay as

Jessica Wolf

Luxe Properties, LLC.

(645) 300-5642

126 Columbus Dr, Islamorada, FL 33036
/79
$11,500 per month
- 4 Beds
- 3 Baths
- 1,800 Sq Ft
- House for Rent
129 Nautilus Dr, Islamorada, FL 33036

Your White Marlin Beach seasonal rental awaits! Sleeps up to 12 guests. This charming two-story home offers a rare layout perfect for multigenerational living. Upstairs you’ll find the main living quarters, while the ground level features a private 2BD/1BA suite with its own kitchenette and entrance. Ideal for hosting guests, creating a private office, or enjoying family retreats. By mid-October,

Victor Ruiz

Move Miami, LLC.

(877) 706-6314

129 Nautilus Dr, Islamorada, FL 33036
/56
$250,000 Sold Sep 19, 2025
- Land
- 33 Days On Market
65821 Overseas Hwy Unit 102, Long Key, FL 33001

Incredible Opportunity in One of the Keys' Most Beloved Communities!Welcome to Lot #102 at 65821 Overseas Hwy, a 1,905 sq ft vacant lot nestled in one of the most sought-after communities in all of the Florida Keys. This rare offering is perfect for those seeking flexibility, community amenities, and an unbeatable location.Residents love living here and for good reason. The community is

Sam Williams Coldwell Banker Schmitt Real Estate Co.

65821 Overseas Hwy Unit 102, Long Key, FL 33001

/60
Est $910,053 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

/34
$890,000 Under Contract
- 2 Beds
- 2 Baths
- 798 Sq Ft
3625 Seaside Dr Unit 312, Key West, FL 33040

Here is a rare opportunity to own a nightly vacation rental condo in Key West with a transient license, allowing for highly profitable short-term rentals. Rental history is available in the documents tab. Located in the sought-after Sunrise Suites Resort, this property offers a long history of consistent rental income. Investors can take over future bookings, ensuring a seamless transition and

Karol Marsden

Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

(305) 876-6371

3625 Seaside Dr Unit 312, Key West, FL 33040
/54
$4,000 per month
- 2 Beds
- 2 Baths
- 850 Sq Ft
- Condo for Rent
10877 Overseas Hwy Unit 38, Marathon, FL 33050

SUMMER SPECIAL! Experience the ultimate FL Keys vacation getaway at this BRAND NEW condo-townhome in the breathtaking community of Ocean Isles Fishing Village! This is the ONLY 2 Bedroom/2 Bathroom in the community that offers complete, comfortable accommodations for up to 6 guests at competitive 1B/1B pricing! Unit 38 is the larger style, two story design. Come into the first floor open

Ganit Arazi

Beachfront Realty Inc

(786) 756-7350

10877 Overseas Hwy Unit 38, Marathon, FL 33050
/42
$749,000 Sold Sep 19, 2025
- 1,008 Sq Ft
- $743/SF
- 88 Days On Market
- 2 Beds
- 2 Baths
- Built 1990
28009 Gulf Blvd, Big Pine Key, FL 33043

Canal-Front Paradise in the Heart of the National Key Deer RefugeBig Pine Key, FloridaWelcome to your serene island escape! Nestled in the heart of the National Key Deer Refuge, this beautifully renovated two-bedroom, two-bath stilt home offers the perfect blend of modern comfort and natural beauty.Property Highlights:Canal-Front Property with ample space for a dock -- ideal for boating

Ian Calderwood Bluescape Real Estate

28009 Gulf Blvd, Big Pine Key, FL 33043

/21
Est $413,096 Not Listed For Sale
- 1 Bed
- 1 Bath
- 467 Sq Ft
1121 W Ocean Dr Unit 10, Key Colony Beach, FL 33051

1121 W Ocean Dr Unit 10, Key Colony Beach, FL 33051

/65
$1,425,000 Under Contract
- 2 Beds
- 2.5 Baths
- 1,252 Sq Ft
96000 Overseas Hwy Unit J5 + 33' boat slip, Key Largo, FL 33037

Presenting an exceptional opportunity to own a premier waterfront townhome in the prestigious Buttonwood Bay Club. Breathtaking bay views stretch across both levels of the home, offering a stunning backdrop of open water views and captivating sunsets. This tastefully updated and impeccably appointed residence boasts a rare 33-foot assigned boat slip--ideal for effortless access to the open bay.

Karol Marsden

Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

(786) 745-7320

96000 Overseas Hwy Unit J5 + 33' boat slip, Key Largo, FL 33037
/52
$9,000 per month
- 3 Beds
- 3 Baths
- House for Rent
317 E Seaview Cir Unit 1, Duck Key, FL 33050

Welcome to the secure and luxurious island of Duck Key. This 3-story, 4-bedroom, 3-bathroom home is perfect for any family. Duck Key features pristine blue waters and excellent dining options, with a yearly rental period that keeps the island tranquil. Enjoy Florida's perks: no state income tax, an average of 230 sunny days per year, stunning beaches, and top-rated public, private, and charter

Joseph Suarez

Trustpoint Realty, LLC

(786) 791-2987

317 E Seaview Cir Unit 1, Duck Key, FL 33050
/52
$845,000 Sold Sep 19, 2025
- 1,352 Sq Ft
- $625/SF
- 114 Days On Market
- 2 Beds
- 2.5 Baths
- Built 1989
12690 Overseas Hwy Unit 411, Marathon, FL 33050

This beautifully updated and professionally decorated two-story townhome offers 2 spacious bedrooms, 2.5 baths, and breathtaking Gulf views from nearly every room!Step out onto the lovely wraparound balcony and soak in the peaceful water views and ocean breeze.Inside, you will find a bright, airy layout with soft coastal tones, a smart, functional kitchen, and upstairs bedrooms for added privacy.

Alyson Bainbridge Coldwell Banker Schmitt Real Estate Co.

12690 Overseas Hwy Unit 411, Marathon, FL 33050

/85
Est $880,296 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,180 Sq Ft
307 Sound Dr, Key Largo, FL 33037

307 Sound Dr, Key Largo, FL 33037

/48
$1,499,000 Pending
- 5 Beds
- 3 Baths
- 2,816 Sq Ft
1427 Boca Chica Rd, Key West, FL 33040

Tons of privacy and fantastic open water views from this 6 Bedroom concrete home surrounded by government land on Geiger Key, a small coastal community of waterfront homes just minutes to the magic of Key West. Perfect for large families or a vacation retreat the 2-story home boasts picture perfect water views from the 4 Bedroom 2nd floor owners residence. Guests will appreciate the 2 Bedroom

Lisa Ferringo

Coldwell Banker Schmitt Lower Keys (KW)

(786) 981-3156

1427 Boca Chica Rd, Key West, FL 33040
/23
$6,000 per month
- 3 Beds
- 2 Baths
- 1,496 Sq Ft
- House for Rent
30 Jean la Fitte Dr, Key Largo, FL 33037

This UNIQUE and rarely to be found property is 1,496 SF living space, 3bed/2baths, waterfront direct bay access, private concrete dock for a 30 FT boat with amazing views of the sun rise on the bay, completely renovated, beautiful kitchen, SS appliances, granite countertop, two bedroom in the first floor and master bedroom in second floor with canal from view, washer & dryer. No Pets

Alma Gonzalez

Blueshore Realty, LLC

(786) 949-3594

30 Jean la Fitte Dr, Key Largo, FL 33037
/43
$675,000 Sold Sep 19, 2025
- 1,162 Sq Ft
- $581/SF
- 118 Days On Market
- 3 Beds
- 1 Bath
- Built 1978
10 W Cook, Cook Island Key, FL 33043

Welcome to Cook Island, a semi-private pristine barrier island offering one of the most beautiful beaches in the Florida Keys. Cook Island is home to just 11 residences and 10W is one of the few offering dockage accessible at low tide . This self-sustaining beach-front property sprawls over 3/4 of an acre and features a 2 Bedroom main house plus a detached beach-front studio with sleeping loft

Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

10 W Cook, Cook Island Key, FL 33043

/6
Est $798,626 Not Listed For Sale
- 1 Bed
- 1 Bath
- 726 Sq Ft
612 Petronia St Unit Rear, Key West, FL 33040

612 Petronia St Unit Rear, Key West, FL 33040

/41
$1,199,000 Pending
- 2 Beds
- 1 Bath
- 1,144 Sq Ft
237 La Fitte Rd, Summerland Key, FL 33042

Located in Little Torch Key, this 2-Bedroom, 1144 sq ft waterfront home boasts breathtaking open water views offering a front-row seat to mesmerizing sunrises and tranquil ocean breezes. Enter into the bright and airy Great Room where a wall of impact glass windows look out to picture perfect water views. The open Kitchen features top-grade appliances, sleek wood and granite countertops, ample

Lisa Ferringo

Coldwell Banker Schmitt Lower Keys (KW)

(786) 937-0738

237 La Fitte Rd, Summerland Key, FL 33042
/70
$12,500 per month
- 4 Beds
- 4 Baths
- 2,952 Sq Ft
- Property for Rent
21640 Overseas Hwy, Summerland Key, FL 33042

Waterfront Paradise in Cudjoe KeyWelcome to 21640 Overseas Highway, Cudjoe Key, FL 33042--a spectacular 4-bedroom, 4-bathroom waterfront sanctuary offering panoramic open-water views and the ultimate Florida Keys lifestyle.Inside, the home features a beautifully updated kitchen with modern finishes, spacious living areas designed for comfort and entertaining, and a huge master suite overlooking

Dan Serban

Key West Luxury Real Estate Inc (KW)

(786) 442-3255

21640 Overseas Hwy, Summerland Key, FL 33042
/35
$600,000 Sold Sep 19, 2025
- 1,296 Sq Ft
- $463/SF
- 247 Days On Market
- 3 Beds
- 2 Baths
- Built 1975
97 Marina Ave, Key Largo, FL 33037

Nearly the lowest price per square foot on the market for similar homes, this is the Deal of the Day in Key Largo. Port Largo 3-bedroom home in one of Key Largo's most desirable neighborhoods at an extra-competitive price. As a resident of Port Largo, you may join the Homeowners Association and have access to the Port Largo Homeowners Park, featuring a private boat ramp and swimming area. The

Jim Signor LoKation Real Estate

97 Marina Ave, Key Largo, FL 33037

/2
Est $961,322 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,499 Sq Ft
85 Henry Morgan Dr, Key Largo, FL 33037

85 Henry Morgan Dr, Key Largo, FL 33037

/40
$645,000 Pending
- 2 Beds
- 1 Bath
- 510 Sq Ft
62900 Overseas Hwy Unit 17, Conch Key, FL 33050

Oceanside Conch Key opportunity! Located on the boat basin with 40 ft. of concrete seawall in Coral Key Village, this prime site provides protected dockage and extremely quick boat access to the Atlantic and back country. Your boat can be launched and docked or trailered in minutes from the free boat ramp for residents; the island also has a convenient boat/trailer storage area, private beach

Patti Nickless

Coldwell Banker Schmitt Lower Keys (KW)

(786) 829-1638

62900 Overseas Hwy Unit 17, Conch Key, FL 33050
/54
$4,000 per month
- 2 Beds
- 2 Baths
- Condo for Rent
96000 Overseas Hwy Unit W44, Key Largo, FL 33037

Stunning fully furnished condo with 31' boat slip. Such a rare find with high-end finishes, stainless appliances, granite countertops, beautifully decorated with marina and partial bay views. Enjoy your coffee on the expansive screened balcony in the morning and then marvel at the spectacular sunsets in the evening. This is a true boater's dream, complete with a 31' boat slip in a deep-water,

Karol Marsden

Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

(786) 807-9668

96000 Overseas Hwy Unit W44, Key Largo, FL 33037
/20
$3,150,000 Sold Sep 19, 2025
- 2,100 Sq Ft
- $1,500/SF
- 257 Days On Market
- 3 Beds
- 3 Baths
- Built 1924
728 Love Ln, Key West, FL 33040

Located in Old Town Key West, and on one of the most sought after tranquil lanes, sits this perfectly updated home in the X zone. Upon entering, the foyer seamlessly flows into an open-concept living room and kitchen. You're welcomed by a breathtaking cathedral ceiling that enhances the sense of space, while large pocket doors draw your gaze to the outdoors. An expansive lanai extends the living

Key West Luxury Finders Preferred Properties (KW)

728 Love Ln, Key West, FL 33040

/62
Est $4,796,311 Not Listed For Sale
- 5 Beds
- 5 Baths
- 3,421 Sq Ft
1141 Ocean Dr, Summerland Key, FL 33042

1141 Ocean Dr, Summerland Key, FL 33042

/46
$1,050,000 Pending
- 3 Beds
- 3 Baths
- 1,598 Sq Ft
76 Palm Dr, Key West, FL 33040

This 2-story home was built for relaxation and views of the open water and unforgettable sunsets. Watching the sun dip down on the horizon, transforming a brilliant blue sky and white fluffy clouds into soft pinks and oranges is pure delight and good for the soul.The property is in the Lower Florida Keys at Mile Marker #15 in Saddlebunch Key, Bay Point Subdivision. It is only 20 minutes to

Margarita Villoch

Island Group Realty (KW)

(786) 628-0498

76 Palm Dr, Key West, FL 33040
/17
$5,000 per month
- 3 Beds
- 2 Baths
- 1,392 Sq Ft
- Townhouse for Rent
660 11th St, Marathon, FL 33050

Updated 3 bedroom, 2 bath, stilt half-duplex in Key Colony Beach. On a canal with 37' of seawall dock. Available August 1st.

Karen Liskey

Key Colony Beach Realty

(786) 983-6199

660 11th St, Marathon, FL 33050
/44
$1,950,000 Sold Sep 19, 2025
- 3,924 Sq Ft
- $497/SF
- 365 Days On Market
- 4 Beds
- 5 Baths
- Built 1958
2718 Harris Ave, Key West, FL 33040

Living large IS possible in Key West! At 3,924 square feet, 2718 Harris Ave is one of the larger private residences in Key West. Now being offered at under $550/sq ft! This impressive home offers an open and airy layout that is perfect for entertaining indoors and out. Entering through the majestic front door, you'll immediately notice the high-end finishes and just how spacious the home

Rodney Culiver Last Key Realty, Inc (KW)

2718 Harris Ave, Key West, FL 33040

/38
Est $794,492 Not Listed For Sale
- 2 Beds
- 1.5 Baths
- 1,130 Sq Ft
97652 Overseas Hwy Unit 12, Key Largo, FL 33037

97652 Overseas Hwy Unit 12, Key Largo, FL 33037

/35
$650,000 Pending
- 3 Beds
- 2 Baths
- 1,300 Sq Ft
31463 Avenue A, Big Pine Key, FL 33043

Welcome to Hibiscus House, your private island retreat in the heart of the Key Deer Sanctuary. This updated 3-bedroom, 2-bathroom home offers 1,300 sq ft of comfortable living space on a fully fenced 5,000 sq ft lot. Upon entering the home, you are welcomed by abundant natural light, showing off a generous living space, with lofty ceilings and luxury vinyl flooring throughout. The recently

Ryan Gernaat

Coldwell Banker Schmitt Lower Keys (KW)

(855) 578-1681

31463 Avenue A, Big Pine Key, FL 33043
/5
$2,500 per month
- 2,244 Sq Ft
- Property for Rent
2001 Flagler Ave, Key West, FL 33040

Prime 2,244 SQFT Vacant Lot Available for Rent.A rare opportunity to lease a centrally located vacant lot in the heart of New Town! Whether you're looking to advertise your business, operate a food truck, start a new venture, or create a space uniquely your own--this versatile lot offers endless potential. Multiple possible uses (tenant to verify).Please do not walk the property without prior

Everett Watkins

Keller Williams Key West Compass Realty

(786) 244-5194

2001 Flagler Ave, Key West, FL 33040
/50
$485,000 Sold Sep 18, 2025
- 994 Sq Ft
- $488/SF
- 75 Days On Market
- 2 Beds
- 2 Baths
- Built 1975
201 E Ocean Dr Unit 110, Key Colony Beach, FL 33051

Welcome to Casa Clara, where laid-back island living meets everyday comfort. This move-in ready 2-bedroom, 2-bath condo offers ocean views from the living room, primary suite, and private balcony--an inviting setting to relax and recharge. The kitchen and baths were tastefully improved over time and have been well cared for. Spend your days enjoying the 600-foot private white sand beach, swimming

Tracy Chacksfield Berkshire Hathaway HomeServices Keys Real Estate

201 E Ocean Dr Unit 110, Key Colony Beach, FL 33051

/17
Est $344,975 Not Listed For Sale
- 1 Bed
- 1 Bath
- 528 Sq Ft
3312 Northside Dr Unit 214, Key West, FL 33040

3312 Northside Dr Unit 214, Key West, FL 33040

/16
$9,198,000 Pending
- Land
721 W Ocean Dr, Key Colony Beach, FL 33051

Fantastic Oceanfront Development Opportunity in the heart of the Florida Keys! 2+ acres of prime oceanfront boasting 225' of beach front with dock permit in Key Colony Beach. A total of 3 lots with endless possibilities. Previous use was a 22 unit condominium. Or look into separating the lots to build 3 new luxury beach homes which are in very hot demand and rare to find. One house on this

Lisa Ferringo

Coldwell Banker Schmitt Lower Keys (KW)

(786) 783-6269

721 W Ocean Dr, Key Colony Beach, FL 33051
/34
$5,750 per month
- 3 Beds
- 3 Baths
- 1,380 Sq Ft
- Property for Rent
59 Palm Dr, Key West, FL 33040

Enjoy the Keys lifestyle in this stunning canal-front 3-bedroom, 3-bathroom elevated modular home, located in the desirable Bay Point neighborhood, just behind Baby's Coffee. Available for $5,900 per month, this 2015-built home offers modern amenities and a spacious layout perfect for comfortable living.The lower level features a bedroom with a full bath, 9-foot ceilings, and access to a covered

Dan Serban

Key West Luxury Real Estate Inc (KW)

(645) 205-0832

59 Palm Dr, Key West, FL 33040
/43
$595,000 Sold Sep 18, 2025
- 912 Sq Ft
- $652/SF
- 114 Days On Market
- 2 Beds
- 2 Baths
- Built 1990
29156 Tulip Ln, Big Pine Key, FL 33043

This home offers privacy with an over-sized grass yard, surrounded by nature with a natural garden and room for all your needs. This double lot property is 10,000SF with room for a pool, tiki and/or an accessory structure. French doors take you to an additional 500+SF screened patio that extends your living space and provides tranquil views over the garden and lush yard. Spend your mornings

Donna Halstead Coldwell Banker Schmitt RE Co.

29156 Tulip Ln, Big Pine Key, FL 33043

/76
Est $1,526,402 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,834 Sq Ft
1063 Avenue A, Big Pine Key, FL 33043

1063 Avenue A, Big Pine Key, FL 33043

/23
$499,000 Pending
- 4 Beds
- 3 Baths
- 1,488 Sq Ft
41G Miriam St, Stock Island, FL 33040

Stock Island opportunity! This mobile home is a 4 bedroom 3 bathroom -it is divided into several lock out rooms that are currently rented If you are looking for housing for employees or good income potential call for more info. Cute front porch, 4 off street parking spaces, fenced yard, shared laundry. The structure has T1-11 siding and frame around the original mobile home in good condition.

Sandra Tuttle

Island Welcome Real Estate

(786) 889-4082

41G Miriam St, Stock Island, FL 33040
/45
$4,000 per month
- 2 Beds
- 1 Bath
- 1,008 Sq Ft
- Property for Rent
136 Sable Palm Ln, Tavernier, FL 33070

Tropical waterfront paradise found! Welcome to 136 Sable Palm Lane -- your slice of island life in the heart of Tavernier! Nestled in the highly sought-after Bluewaters community of Key Largo offering a perfect blend of modern amenities and coastal charm. Enjoy open-concept living with abundant natural light, coastal finishes, and a breezy layout designed for relaxed living. This charming

Sandro Herrera

Three Palms Realty

(844) 628-8162

136 Sable Palm Ln, Tavernier, FL 33070
/40
$750,000 Sold Sep 17, 2025
- 900 Sq Ft
- $833/SF
- 10 Days On Market
- 2 Beds
- 2 Baths
- Built 1960
41 Sadowski Causeway, Key Colony Beach, FL 33051

Welcome to 41 Sadowski Causeway, a beautifully renovated half-duplex in the heart of Key Colony Beach. This turnkey waterfront retreat blends modern upgrades with the classic Florida Keys lifestyle. Inside, you'll find a light and bright living space with brand-new appliances and tasteful finishes throughout. Move-in ready with nothing left to do but enjoy!Step outside to your private 45' deep

Milly Cruz Engel & Volkers Marathon

41 Sadowski Causeway, Key Colony Beach, FL 33051

/2
Est $982,628 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,497 Sq Ft
3738 Eagle Ave, Key West, FL 33040

3738 Eagle Ave, Key West, FL 33040

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