Monroe County, FL Homes

/69
$1,499,999
- 3 Beds
- 3 Baths
- 1,786 Sq Ft
126 Columbus Dr, Islamorada, FL 33036

Florida Keys waterfront home, offered fully furnished, 1,786 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 & elevated in 2021. Boaters paradise w/75FT of dockage, under 5 minute ride to open ocean + easy access to bay as well, plenty of space to install a boat lift.

Jessica Wolf

Luxe Properties, LLC.

(786) 981-3256

126 Columbus Dr, Islamorada, FL 33036
/13
$4,550 per month
- 3 Beds
- 2 Baths
- 1,290 Sq Ft
- Property for Rent
2635 Koehns Ave, Big Pine Key, FL 33043

Discover this charming 3-bedroom, 2-bathroom furnished home.2-year lease preferred but negotiable.The spacious, open floor plan features a gourmet kitchen with white quartz countertops and sleek, stainless-steel Bertazzoni appliances imported from Italy.Relax in the dining area, overlooking a screened-in patio with stunning views of the heated saltwater pool. The lush backyard is a tropical

Karen Liskey

Key Colony Beach Realty

(866) 729-5076

2635 Koehns Ave, Big Pine Key, FL 33043
/88
$700,000 Sold Dec 31, 2025

104500 Overseas Hwy Unit C301, Key Largo, FL 33037
- 3 Beds
- 2 Baths
- 1,577 Sq Ft
- Built 1981
Last Sold Summary
- 11% Below List Price
- $444/SF
- 1 Day On Market
Last Listing Agent Strain-Pabotoy T Coldwell Banker Schmitt Coldwell Banker Schmitt Key Largo

104500 Overseas Hwy Unit C301, Key Largo, FL 33037

/8
Est $358,003 Not Listed For Sale
- 1 Bed
- 45 Sq Ft
1550 Ocean Bay Dr Unit 42, Key Largo, FL 33037

1550 Ocean Bay Dr Unit 42, Key Largo, FL 33037

/48
$2,250,000
- 3 Beds
- 2 Baths
- 1,710 Sq Ft
415 Sombrero Beach Rd, Marathon, FL 33050

Discover an extraordinary waterfront oasis in the heart of the Florida Keys. Located just moments from the pristine sands of Sombrero Beach, this elegant estate blends modern sophistication with the relaxed charm of coastal living. Designed for the discerning buyer, every detail of this property reflects luxury, comfort, and an unparalleled boating lifestyle. Elevated foundation - permitted for

Tyler Weant

Keller Williams Key West Compass Realty

(833) 262-4161

415 Sombrero Beach Rd, Marathon, FL 33050
/39
$2,850 per month
- 2 Beds
- 1.5 Baths
- 981 Sq Ft
- Townhouse for Rent
87465 Old Hwy Unit 224, Islamorada, FL 33036

LONG TERM RENTAL in desirable Islamorada at Plantation By The Sea Condominiums. 6 Mos and 1 day ; 1 year; or 2 years. See below for details. Ocean front complex. During your free time lounge by the pool and gaze at the Atlantic Ocean or walk out on the long pier and catch your dinner! Wonderful two-story townhouse style condo completely furnished. Linens, dishes, pots and pans - everything,

Andrea (Andi) Saylor

Paradise Florida Keys Real Estate, a Luxury Brand

(888) 430-3847

87465 Old Hwy Unit 224, Islamorada, FL 33036
/49
$1,230,000 Sold May 07, 2025

104 Buttonwood Ln, Long Key, FL 33001
- 3 Beds
- 2.5 Baths
- 1,607 Sq Ft
- Built 1990
Last Sold Summary
- 11% Below List Price
- $765/SF
- 77 Days On Market
Current Estimated Value $1,267,187

Last Listing Agent Jo Ann Cook Ocean Sotheby's International

104 Buttonwood Ln, Long Key, FL 33001

/26
Est $363,367 Not Listed For Sale
- 2 Beds
- 2 Baths
- 400 Sq Ft
84961 Old Hwy Unit 9, Islamorada, FL 33036

84961 Old Hwy Unit 9, Islamorada, FL 33036

/45
$1,995,000 Pending
- 3 Beds
- 2 Baths
- 1,928 Sq Ft
96000 Overseas Hwy Unit EE1, Key Largo, FL 33037

The Ultimate in Luxurious Waterfront Living.Step into this exquisite residence and be instantly captivated by panoramic bay views framed by floor-to-ceiling glass doors, flowing seamlessly to the paver patio and sunset martini dock beyond. One of only three ground-floor, three-bedroom bayfront condos, this is a rare opportunity to own among Buttonwood Bay Club's most exclusive homes.Beautifully

Karol Marsden

Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

(786) 481-1534

96000 Overseas Hwy Unit EE1, Key Largo, FL 33037
/39
$4,000 per month
- 2 Beds
- 2 Baths
- 1,008 Sq Ft
- Property for Rent
136 Sable Palm Ln, Tavernier, FL 33070

AVAILABLE NOVEMBER - APRIL Welcome to 136 Sable Palm in Tavernier a cozy waterfront retreat offering the ultimate Florida Keys lifestyle! This charming 2-bedroom, 2-bathroom home is nestled on a finger canal with direct access to the open water. Spacious Outdoor Living - Ideal for entertaining or relaxing by the water. Whether you're a boating enthusiast or looking for a peaceful escape, this

Ashley Kettner

Tolliver Prince Realty

(844) 628-8162

136 Sable Palm Ln, Tavernier, FL 33070
/64
$3,243,000 Sold Apr 18, 2025

1122 Seminary St, Key West, FL 33040
- 4 Beds
- 5 Baths
- 2,650 Sq Ft
- Built 1938
Last Sold Summary
- 10% Below List Price
- $1,224/SF
- 152 Days On Market
Current Estimated Value $3,316,384

Last Listing Agent Paul Brooks Compass Florida, LLC

1122 Seminary St, Key West, FL 33040

/44
Est $1,093,128 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,028 Sq Ft
302 Anglers Dr N Unit A, Marathon, FL 33050

302 Anglers Dr N Unit A, Marathon, FL 33050

/31
$795,000
- 3 Beds
- 1 Bath
- 1,562 Sq Ft
360 W Shore Dr, Summerland Key, FL 33042

Discover island living in this charming 3-bedroom, 1-bath canal-front home located in desirable Summerland Key, featuring fabulous sunset views. Set on a 60-foot-wide deep canal with approximately 10 minutes of boating access to the open ocean, this property is ideal for avid boaters and water lovers.The open living area flows seamlessly into an enclosed porch, creating a versatile space perfect

Brenda Thomas

Island Welcome Real Estate

(786) 949-3594

360 W Shore Dr, Summerland Key, FL 33042
/52
$7,500 per month
- 3 Beds
- 2 Baths
- House for Rent
317 E Seaview Cir, 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) 982-0453

317 E Seaview Cir, Duck Key, FL 33050
/60
$1,022,500 Sold Dec 01, 2025

29490 Ranger Ave, Big Pine Key, FL 33043
- 3 Beds
- 2 Baths
- 1,346 Sq Ft
- Built 2018
Last Sold Summary
- 6% Below List Price
- $760/SF
- 46 Days On Market
Last Listing Agent Jennifer Sylvia Keller Williams Key West Compass Realty

29490 Ranger Ave, Big Pine Key, FL 33043

/12
Est $269,307 Not Listed For Sale
- 1 Bed
- 45 Sq Ft
96 Madeira Rd Unit 26, Islamorada, FL 33036

96 Madeira Rd Unit 26, Islamorada, FL 33036

/35
$1,375,000
- 2 Beds
- 2 Baths
- 1,278 Sq Ft
96000 Overseas Hwy Unit EE33, Key Largo, FL 33037

Amazing Location in Buttonwood Bay Club. Experience breathtaking open water views the moment you step into this top-floor condo. This beautifully updated and furnished two-bedroom, two-bath condo is like new. It features large format tile floors, new kitchen, new bathrooms, updated doors, custom built-ins, newer appliances, and impact-resistant windows and doors throughout. Highest-end finishes

Karol Marsden

Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

(844) 840-0820

96000 Overseas Hwy Unit EE33, Key Largo, FL 33037
/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
/55
$1,850,000 Sold Jan 30, 2026

272 Lower Matecumbe Rd, Key Largo, FL 33037
- 4 Beds
- 3 Baths
- 2,262 Sq Ft
- Built 2025
Last Sold Summary
- 31% Below List Price
- $818/SF
- 267 Days On Market
Last Listing Agent Yvette Doherty Coldwell Banker Schmitt Key Largo

272 Lower Matecumbe Rd, Key Largo, FL 33037

/46
Est $812,148 Not Listed For Sale
- 6 Beds
- 4 Baths
- 2,240 Sq Ft
163 Jo-Jean Way Unit Duplex, Tavernier, FL 33070

163 Jo-Jean Way Unit Duplex, Tavernier, FL 33070

/32
$939,000
- 3 Beds
- 2 Baths
- 1,144 Sq Ft
31343 Avenue I, Big Pine Key, FL 33043

Welcome to a boater's dream on Big Pine Key. Built in 2020 and still feels brand new, this beautifully maintained 3-bedroom, 2-bath home is offered fully furnished and ready to enjoy or generate rental income. A 75-foot concrete dock delivers outstanding boating access, placing you just minutes from premier fishing grounds and offering easy routes to both the Gulf and the Ocean. Designed for

Sandra Tuttle

Island Welcome Real Estate

(877) 346-6985

31343 Avenue I, Big Pine Key, FL 33043
/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.

(305) 788-7183

129 Nautilus Dr, Islamorada, FL 33036
/18
$738,000 Sold Mar 28, 2025

27438 Haiti Ln, Summerland Key, FL 33042
- 2 Beds
- 2 Baths
- 816 Sq Ft
- Built 1987
Last Sold Summary
- 8% Below List Price
- $904/SF
- 146 Days On Market
Current Estimated Value $740,700

Last Listing Agent Caroline Bauer Key West Sales, LLC

27438 Haiti Ln, Summerland Key, FL 33042

/35
Est $221,426 Not Listed For Sale
701 Spanish Main Dr Unit 647, Cudjoe Key, FL 33042

701 Spanish Main Dr Unit 647, Cudjoe Key, FL 33042

/29
$550,000
- 2 Beds
- 2 Baths
- 826 Sq Ft
500 Burton Dr Unit 1202, Tavernier, FL 33070

Turnkey 2BD/2BA Ocean Pointe Condo - Fully Furnished, Short-Term Rentals Allowed!Welcome to paradise! This beautiful 2-bedroom, 2-bathroom condo in the sought-after Ocean Pointe community offers the perfect blend of luxury, convenience, and income potential. With 826 sq ft of thoughtfully designed living space, this fully furnished, turnkey unit is ready for immediate occupancy or short-term

Philip Kravitz

Coldwell Banker Schmitt Key Largo

(786) 686-3080

500 Burton Dr Unit 1202, Tavernier, FL 33070
/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
/40
$584,900 Sold May 14, 2025

9842 Leeward Ave, Key Largo, FL 33037
- 2 Beds
- 2 Baths
- 1,029 Sq Ft
- Built 1988
Last Sold Summary
- 2% Below List Price
- $568/SF
- 3 Days On Market
Current Estimated Value $639,687

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

9842 Leeward Ave, Key Largo, FL 33037

/25
Not Listed For Sale
- 3 Beds
- 3 Baths
- 1,268 Sq Ft
1220 Seminary St, Key West, FL 33040

1220 Seminary St, Key West, FL 33040

/33
$1,299,000
- 2 Beds
- 2.5 Baths
- 1,320 Sq Ft
96000 Overseas Hwy Unit P1, Key Largo, FL 33037

Rare end-unit town home located on the island area of the prestigious Buttonwood Bay Club. This fully furnished, beautifully updated home has granite countertops, high-end finishes, an open-concept living and dining area, and impact glass doors that lead out to your patio where you can grill, entertain or simply relax. This is a true boater's dream, complete with a 32' boat slip in a deep-water,

Karol Marsden

Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

(786) 983-3167

96000 Overseas Hwy Unit P1, Key Largo, FL 33037
/12

$2,700 per month

Coco Palms

2 Beds

21585 Overseas Hwy, Cudjoe Key, FL 33042

Discover our newly constructed community at Coco Palms in Cudjoe Key, Florida. The leasing team will assist you in finding your new place. A selection of amenities are waiting for you: hurricane windows and doors, dishwashers, washers and dryers and convenient on-site parking options. Contact us today to see available floor plans and find your new place at Coco Palms.

21585 Overseas Hwy, Cudjoe Key, FL 33042
/27
$837,000 Sold Jul 11, 2025

27417 Cayman Ln, Summerland Key, FL 33042
- 2 Beds
- 1 Bath
- 1,085 Sq Ft
- Built 1975
Last Sold Summary
- 14% Below List Price
- $771/SF
- 274 Days On Market
Current Estimated Value $842,095

Last Listing Agent Karen Quist Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key

27417 Cayman Ln, Summerland Key, FL 33042

/34
Not Listed For Sale
23, Marathon, FL 33050

23, Marathon, FL 33050

/20
$329,900
- 2 Beds
- 1.5 Baths
- 1,024 Sq Ft
300 Ocean Dr Unit 22, Key Largo, FL 33037

Discover Key Largo's Hidden Gem - Holiday By the Sea! This solid concrete fortress, nestled in an X-Flood Zone, has been beautifully upgraded with new electrical, air conditioning/heating, hot water tank, doors, flooring, blinds, and fresh paint.Enjoy harbor views from two of your three private balconies and take advantage of this prime location just steps from Key Largo Harbor Marina. Whether

Philip Kravitz

Coldwell Banker Schmitt Key Largo

(786) 833-7005

300 Ocean Dr Unit 22, Key Largo, FL 33037
/45
$5,000 per month
- 2 Beds
- 2 Baths
- 1,408 Sq Ft
- House for Rent
37 Blue Water Dr, Key West, FL 33040

A short drive from Key West, this charming canal-front home is perfect for long-term living! Featuring 2 bedrooms, 2 baths, a spacious master suite with water views, and an open floor plan for easy entertaining. Enjoy a covered deck, bonus loft, laundry room, and plenty of storage. With central AC, impact windows, ample parking, and space for a boat or kayaks, this well-kept home offers peaceful

Justyn Ewald Expert Realty LLC

37 Blue Water Dr, Key West, FL 33040
/33
$3,690,000 Sold Apr 02, 2025

716 Duval St, Key West, FL 33040
- 3 Beds
- 2 Baths
- 1,800 Sq Ft
- Built 1933
Last Sold Summary
- 14% Below List Price
- $2,050/SF
- 14 Days On Market
Current Estimated Value $3,618,077

Last Listing Agent Jennifer Newman Truman & Co. (KW)

716 Duval St, Key West, FL 33040

/17
Not Listed For Sale
201 Ocean Reef Dr, Key Largo, FL 33037

201 Ocean Reef Dr, Key Largo, FL 33037

/33
$845,000
- 2 Beds
- 1.5 Baths
- 947 Sq Ft
104350 Overseas Hwy Unit A402, Key Largo, FL 33037

Stunning Bayfront Condo in Moon Bay - Fully Furnished with Deeded Boat Slip!Experience the best of waterfront living in this beautifully appointed 2-bedroom, 1.5-bath condo in the sought-after Moon Bay community. This fully furnished unit boasts impact windows and doors, offering breathtaking bay views from the living room, patio, and master bedroom.A boater's dream, the property includes a

Philip Kravitz

Coldwell Banker Schmitt Key Largo

(305) 419-2769

104350 Overseas Hwy Unit A402, Key Largo, FL 33037
/2

$2,349 - $2,849 per month

CoCo Vista

1 - 3 Beds

96 Coco Plum Dr, Marathon, FL 33050

96 Coco Plum Dr, Marathon, FL 33050
/45
$2,900,000 Sold Jan 09, 2026

1224 Florida St, Key West, FL 33040
- 5 Beds
- 6 Baths
- 2,760 Sq Ft
- Built 2006
Last Sold Summary
- 9% Below List Price
- $1,051/SF
- 56 Days On Market
Last Listing Agent Brenda Donnelly Brenda Donnelly Real Estate LLC

1224 Florida St, Key West, FL 33040

/38
Est $720,566 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 1,200 Sq Ft
312 2nd Terrace, Key Largo, FL 33037

312 2nd Terrace, Key Largo, FL 33037

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