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
/10
$3,750 per month
- 1 Bed
- 1 Bath
- 475 Sq Ft
- Property for Rent
621 Whitehead St, Key West, FL 33040

Charming 1-Bedroom Home in Old Town with Bonus Loft Space! Fully renovated 1-bedroom, 1-bathroom rental home in the heart of Old Key West, featuring a bonus loft, one off-street parking space and a washer/dryer inside. Fully furnished, the property includes a cozy sitting room, a well-equipped kitchen, large bedroom, and updated bathroom with new shower. Relax on the porch, surrounded by lush

Damian Vantriglia

Berkshire Hathaway HomeServices Knight & Gardner Realty

(786) 882-1353

621 Whitehead St, Key West, FL 33040
/33
$2,620,000 Sold Jan 29, 2025

17279 Pinetree Ln, Summerland Key, FL 33042
- 2 Beds
- 2 Baths
- 1,016 Sq Ft
- Built 1956
Last Sold Summary
- 11% Below List Price
- $2,579/SF
- 288 Days On Market
Current Estimated Value $2,546,875

Last Listing Agent Dan Serban Key West Luxury Real Estate Inc (KW)

17279 Pinetree Ln, Summerland Key, FL 33042

/4
Not Listed For Sale
- 2 Beds
- 1 Bath
- 1,392 Sq Ft
97 Avenue B, Key Largo, FL 33037

97 Avenue B, Key Largo, FL 33037

/30
$679,000
- 2 Beds
- 2.5 Baths
- 1,362 Sq Ft
349 Mahogany Dr, Key Largo, FL 33037

This spacious 2BR/2.5BA CBS home on a double lot (10,700 sq. ft) is your chance to own in paradise without breaking the bank. Located off Mile Marker 102 Ocean Side. You'll love the updated interior with modern upgrades, tile floors throughout, hurricane impact windows for peace of mind and large screened patio surrounded by lush tropical landscaping perfect for relaxing after a day on the water.

Nancy Rodriguez Gadinsky

Coldwell Banker Realty - Coral Gables

(786) 982-7718

349 Mahogany Dr, Key Largo, FL 33037
/2
$3,000 per month
- 2 Beds
- 1 Bath
- 1,380 Sq Ft
- House for Rent
50 Orange Dr Unit B, Key Largo, FL 33037

Newer beautiful corner 2 bedroom 1 bath on ground level of single family home. No stairs. tiled throughout. Impact windows and doors. Nice backyard. Electric and water included up to $225 per month. Private homeowners park with beach, picnic area, tiki and boat ramp close by. Located at mile marker 100. Very quiet area near schools, shopping, restaurants and more.

Zachary Tranten

Keys Gate Realty, Inc.

(888) 835-6430

50 Orange Dr Unit B, Key Largo, FL 33037
/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 $1,267,736

Last Listing Agent Jo Ann Cook Ocean Sotheby's International

104 Buttonwood Ln, Long Key, FL 33001

/51
Not Listed For Sale
- 2 Beds
- 2 Baths
- 864 Sq Ft
701 Spanish Main Dr Unit 167, Cudjoe Key, FL 33042

701 Spanish Main Dr Unit 167, Cudjoe Key, FL 33042

/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
$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 $3,257,997

Last Listing Agent Paul Brooks Compass Florida, LLC

1122 Seminary St, Key West, FL 33040

/22
Est $837,654 Not Listed For Sale
- 2 Beds
- 1 Bath
- 580 Sq Ft
620 Thomas St Unit 286, Key West, FL 33040

620 Thomas St Unit 286, Key West, FL 33040

/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
/52
$8,500 per month
- 3 Beds
- 3 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

/35
Not Listed For Sale
- 2 Beds
- 2 Baths
- 813 Sq Ft
65821 Overseas Hwy, Long Key, FL 33001

65821 Overseas Hwy, Long Key, FL 33001

/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
/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
/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 $736,126

Last Listing Agent Caroline Bauer Key West Sales, LLC

27438 Haiti Ln, Summerland Key, FL 33042

/49
Est $1,749,632 Not Listed For Sale
- 2 Beds
- 2 Baths
- 2,126 Sq Ft
520 12th St, Key Colony Beach, FL 33051

520 12th St, Key Colony Beach, FL 33051

/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
/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
/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 $637,295

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

9842 Leeward Ave, Key Largo, FL 33037

/47
Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,809 Sq Ft
1302 Calder Rd, Key Largo, FL 33037

1302 Calder Rd, Key Largo, FL 33037

/91
$3,200,000
- 3 Beds
- 4.5 Baths
- 2,608 Sq Ft
16 North Dr, Key Largo, FL 33037

Stunning bayfront retreat in a sought-after subdivision of Key Largo, MM105.5, offering privacy, abundant natural light, and a refined Florida Keys lifestyle with convenient access to Miami. This contemporary waterfront residence features an open, airy layout with 3 bedrooms and 4 bathrooms, spacious studio and in-laws quarter- both its own entrance designed for comfort and relaxation. The sleek,

Catherine Pineda

Coldwell Banker Realty

(888) 357-4344

16 North Dr, Key Largo, FL 33037
/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
/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 $836,765

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

27417 Cayman Ln, Summerland Key, FL 33042

/76
Est $2,814,409 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,955 Sq Ft
31 Seagate Blvd, Key Largo, FL 33037

31 Seagate Blvd, Key Largo, FL 33037

/42
$1,094,000
- 3 Beds
- 3 Baths
- 1,203 Sq Ft
60 Golf Club Dr, Key West, FL 33040

Welcome to 60 Golf Club Drive, Key West, FL - A Fully Furnished Tropical Retreat with Private Pool and Turnkey Rental OpportunityStep into island living at its finest in this beautifully appointed 3-bedroom, 2.5-bath home with well appointed den / office (could function as 4th bedroom) located in the sought-after Key West Golf Club community. This charming residence offers the perfect blend of

Matthew Sheehan

Ocean Sotheby's International Realty

(786) 882-1587

60 Golf Club Dr, Key West, FL 33040
/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
/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 $3,510,444

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

716 Duval St, Key West, FL 33040

/35
Est $1,897,369 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,644 Sq Ft
1430 Thompson St, Key West, FL 33040

1430 Thompson St, Key West, FL 33040

/9
$550,000
- Land
5950 Peninsular Ave Unit 629, Key West, FL 33040

A beautiful 50' live aboard slip at Oceanside Marina (Oceans Edge Resort). Direct deep water access to the Atlantic Ocean make this a perfect Key West getaway for a passionate boater, vacation or permanent Key West home on a boat, or for a charter boat captain. Owners have full access to the resort facilities at Oceans Edge Resort, including six pools, a fitness center, full bath house with

Cardenas & Krug Team

Ocean Sotheby's International Realty

(786) 876-8545

5950 Peninsular Ave Unit 629, Key West, FL 33040
/17
$5,500 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

(645) 654-9292

30 Jean la Fitte Dr, Key Largo, FL 33037
/40
$522,500 Sold Oct 10, 2025

1115 Sombrero Blvd Unit 101A, Marathon, FL 33050
- 2 Beds
- 2 Baths
- 1,096 Sq Ft
- Built 1975
Last Sold Summary
- 5% Below List Price
- $477/SF
- 228 Days On Market
Last Listing Agent Ally Kelley Ocean Sotheby's International

1115 Sombrero Blvd Unit 101A, Marathon, FL 33050

/69
Est $1,584,576 Not Listed For Sale
- 3 Beds
- 4 Baths
- 2,160 Sq Ft
121 Grassy Rd, Key Largo, FL 33037

121 Grassy Rd, Key Largo, FL 33037

/103
$5,750,000
- 5 Beds
- 4 Baths
- 3,580 Sq Ft
230 15th Cir, Key Colony Beach, FL 33051

Brand new 2025 waterfront masterpiece. 5 bed, 4 bath, 3,580 sf on a 9,720 sf lot. Built 100% CBS with impact glass and metal roof.Luxurious finishes include Calacatta Viola, travertine and coral stone, Thermador 48' gas range, marble hood, Brizo fixtures, wine cellar, expansive walk-in closets, and private office.Resort-style outdoors: 10x28 pool with sun shelf, summer kitchen, brand-new

Joseph Suarez

Trustpoint Realty, LLC

(786) 837-5756

230 15th Cir, Key Colony Beach, FL 33051
/39
$2,950 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

(888) 430-3847

87465 Old Hwy Unit 224, Islamorada, FL 33036
/7
$1,056,000 Sold Jul 21, 2025

972 Shaw Dr, Key Largo, FL 33037
- Land
Last Sold Summary
- 12% Below List Price
- 54 Days On Market
Current Estimated Value $1,062,773

Last Listing Agent Betsy Perez LoKation Real Estate

972 Shaw Dr, Key Largo, FL 33037

/54
Est $1,014,627 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,024 Sq Ft
97501 Overseas Hwy Unit 401, Key Largo, FL 33037

97501 Overseas Hwy Unit 401, Key Largo, FL 33037

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