Monroe County, FL Homes

/71
$1,499,999
- 3 Beds
- 3 Baths
- 1,786 Sq Ft
126 Columbus Dr, Islamorada, FL 33036

Seller will consider seller financing. Florida Keys waterfront home, offered fully furnished, no homeowners association, 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

Jessica Wolf

Luxe Properties, LLC.

(786) 981-3256

126 Columbus Dr, Islamorada, FL 33036
/17
$4,000 per month
- 1 Bed
- 1 Bath
- 609 Sq Ft
- Property for Rent
828 Fleming St, Key West, FL 33040

Available now, this brand-new Old Town renovation offers a rare blend of style, comfort, and location on one of the Historic District's most premier blocks. Thoughtfully redesigned with beautiful rattan ceilings, white oak hardwood floors, and a bright, refined interior, the home brings a fresh, elevated feel to classic Key West living. A private patio extends the living space outdoors, while a

Damian Vantriglia

Berkshire Hathaway HomeServices Knight & Gardner Realty

(786) 772-3147

828 Fleming St, Key West, FL 33040
/69
$725,000 Sold Feb 17, 2026

16 Jewfish Ave, Key Largo, FL 33037
- 3 Beds
- 2 Baths
- 1,469 Sq Ft
- Built 2018
Last Sold Summary
- 6% Below List Price
- $494/SF
- 153 Days On Market
Current Estimated Value $745,894

Last Listing Agent Silvestri Team Jeanette & Janessa Silves Coldwell Banker Schmitt Key Largo

16 Jewfish Ave, Key Largo, FL 33037

/25
Not Listed For Sale

145 Westminster Dr, Tavernier, FL 33070
- 3 Beds
- 2 Baths
- 1,579 Sq Ft
- Built 1976
145 Westminster Dr, Tavernier, FL 33070

Last Sold Summary
- $665/SF
- 20 Days On Market
Last Sold Price $1,050,000

Last Listing Agent Jan Keller Coldwell Banker Schmitt Islamorada

/48
$2,100,000
- 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
/18
$7,500 per month
- 2 Beds
- 3 Baths
- 1,304 Sq Ft
- Property for Rent
6 Calle Dos, Key West, FL 33040

The Rockland Key Resort is an amazing waterfront home only minutes from Key West. This beautifully renovated home is the perfect Keys oasis. Private fenced yard with mature landscape, new artificial turf, lanai, pool, and covered outdoor space. Ideal open floor plan with light-filled spaces overlooking the canal and pool. The kitchen offers stainless steel appliances, granite counters, &

Dan Serban

Key West Luxury Real Estate Inc (KW)

(645) 300-1139

6 Calle Dos, Key West, FL 33040
/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
Current Estimated Value $718,988

Last Listing Agent Strain-Pabotoy T Coldwell Banker Schmitt Coldwell Banker Schmitt Key Largo

104500 Overseas Hwy Unit C301, Key Largo, FL 33037

/44
Est $843,610 Not Listed For Sale

6800 Maloney Ave Unit 8, Stock Island, FL 33040
- 2 Beds
- 2 Baths
- 960 Sq Ft
- Built 2014
6800 Maloney Ave Unit 8, Stock Island, FL 33040

Last Sold Summary
- 12% Above List Price
- $781/SF
- 43 Days On Market
Last Sold Price $750,000

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

/42
$899,000 Open Sat 10AM - 2PM
- 4 Beds
- 3 Baths
- 1,666 Sq Ft
87 Marina Ave, Key Largo, FL 33037

Watch fireworks from your rooftop deck, relax by your heated and chilled pool, and keep your boat ready to launch just down the street.Welcome to this beautifully maintained 4-bedroom, 3-bathroom home in the highly sought-after Port Largo neighborhood of Key Largo. Offering 1,666 sq ft of bright living space, soaring ceilings, skylights, and a private one-bedroom guest apartment above flood

Philip Kravitz

Coldwell Banker Schmitt Key Largo

(645) 231-3902

87 Marina Ave, Key Largo, FL 33037
/17
$3,750 per month
- 3 Beds
- 2 Baths
- 1,217 Sq Ft
- Property for Rent
3930 S Roosevelt Blvd Unit S110, Key West, FL 33040

Available on the 1st of April, 3 bed and 2 bath, the largest unit in Las Salinas, no pets, $3,750.00 per month and its F/L/D to get in.Renters pay all utilities and must pass a background check and it can be done at the property manager's office.

Dan Serban

Key West Luxury Real Estate Inc (KW)

(645) 239-2670

3930 S Roosevelt Blvd Unit S110, Key West, FL 33040
/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 $3,220,397

Last Listing Agent Paul Brooks Compass Florida, LLC

1122 Seminary St, Key West, FL 33040

/21
Est $878,916 Not Listed For Sale

81801 Overseas Hwy Unit 208, Islamorada, FL 33036
- 1 Bed
- 1 Bath
- 840 Sq Ft
- Built 2010
81801 Overseas Hwy Unit 208, Islamorada, FL 33036

Last Sold Summary
- 5% Above List Price
- $1,000/SF
- 117 Days On Market
Last Sold Price $840,000

Last Listing Agent Lisa Frins Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

/31
$749,500
- 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
/33
$6,000 per month
- 2 Beds
- 2 Baths
- 999 Sq Ft
- Property for Rent
32 Beach Dr, Key West, FL 33040

Available April 1st 2026.Stunning open water views from this beautiful oceanfront home. You can enjoy quiet mornings and spectacular sunsets.The home features 2 bedrooms 2 bathrooms and the main bedroom has a king and an en-suite. The guest bedroom is furnished with a queen size bed. Second bathroom can be accessed from the main living/kitchen area, as well as from the guest bedroom hallway. Pets

Dan Serban

Key West Luxury Real Estate Inc (KW)

(645) 225-2492

32 Beach Dr, Key West, FL 33040
/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 $1,245,118

Last Listing Agent Jo Ann Cook Ocean Sotheby's International Realty

104 Buttonwood Ln, Long Key, FL 33001

/18
Est $433,157 Not Listed For Sale

3930 S Roosevelt Blvd Unit S202, Key West, FL 33040
- 1 Bed
- 1 Bath
- 522 Sq Ft
- Built 1991
3930 S Roosevelt Blvd Unit S202, Key West, FL 33040

Last Sold Summary
- 6% Below List Price
- $881/SF
- 112 Days On Market
Last Sold Price $460,000

Last Listing Agent Letisia Powell Robert Slack LLC

/41
$625,000
- 2 Beds
- 1.5 Baths
- 947 Sq Ft
104350 Overseas Hwy Unit A204, Key Largo, FL 33037

Turnkey Florida Keys Condo with Weekly Rentals Allowed - Fully Furnished in Moon BayThis fully furnished 2BR / 1.5BA condo plus den (3rd sleeping area) in Moon Bay offers 947 sq ft of bright, comfortable living space and is ready for immediate enjoyment or rental income.The unit features stainless steel appliances, impact windows and doors, spacious bedrooms, a private balcony, in-unit washer &

Philip Kravitz

Coldwell Banker Schmitt Key Largo

(645) 215-6463

104350 Overseas Hwy Unit A204, Key Largo, FL 33037
/50
$3,750 per month
- 2 Beds
- 1.5 Baths
- 1,056 Sq Ft
- Townhouse for Rent
96000 Overseas Hwy Unit S8, Key Largo, FL 33037

Annual rental available in this beautiful townhome with a 24' boat slip in 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 24' boat slip in a

Karol Marsden

Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

(305) 676-8117

96000 Overseas Hwy Unit S8, Key Largo, FL 33037
/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
Current Estimated Value $1,041,220

Last Listing Agent Jennifer Sylvia Keller Williams Key West Compass Realty

29490 Ranger Ave, Big Pine Key, FL 33043

/28
Est $507,074 Not Listed For Sale

200 Wrenn St Unit 406, Tavernier, FL 33070
- 2 Beds
- 2 Baths
- 1,179 Sq Ft
- Built 1975
200 Wrenn St Unit 406, Tavernier, FL 33070

Last Sold Summary
- 9% Above List Price
- $394/SF
- 158 Days On Market
Last Sold Price $465,000

Last Listing Agent Brandi Horton Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

/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
/18
$4,400 per month
- 2 Beds
- 1 Bath
- 950 Sq Ft
- Property for Rent
1916 Staples Ave, Key West, FL 33040

ANNUAL RENTAL! Available JUNE 1st. The perfect Key West classic cottage with all the modern features! Perfectly located just short bike ride to Old Town or distance to the island's major shopping centers. Gated entry and fenced in. Large storage area in backyard, Gas BBQ grill for cookouts and sundeck. Has Washer/dryer in rear utility room. Nicely appointed interior fully furnished with a coastal

Christian Loffreno

Loffreno Real Estate

(786) 244-6868

1916 Staples Ave, Key West, FL 33040
/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
Current Estimated Value $1,856,259

Last Listing Agent Yvette Doherty Coldwell Banker Schmitt Key Largo

272 Lower Matecumbe Rd, Key Largo, FL 33037

/54
Est $2,130,742 Not Listed For Sale

94825 Overseas Hwy Unit 28, Key Largo, FL 33037
- 5 Beds
- 5.5 Baths
- 4,500 Sq Ft
- Built 2024
94825 Overseas Hwy Unit 28, Key Largo, FL 33037

Last Sold Summary
- 1% Above List Price
- $470/SF
- 203 Days On Market
Last Sold Price $2,117,000

Last Listing Agent The Florida Keys Sold Sisters Ocean Sotheby's International Realty

/26
$899,000 Open Fri 11AM - 1PM
- 3 Beds
- 2 Baths
- 1,144 Sq Ft
31343 Avenue I, Big Pine Key, FL 33043

A perfect 1031 exchange property! Active vacation rental with history and future bookings. 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

Sandra Tuttle

Island Welcome Real Estate

(877) 346-6985

31343 Avenue I, Big Pine Key, FL 33043
/13
$4,350 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. ALL UTILITIES ARE INCLUDED. 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 paradise,

Karen Liskey

Key Colony Beach Realty

(866) 729-5076

2635 Koehns Ave, Big Pine Key, FL 33043
/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 $741,502

Last Listing Agent Caroline Bauer Key West Sales, LLC

27438 Haiti Ln, Summerland Key, FL 33042

/80
Est $1,687,029 Not Listed For Sale

162 Sun Ln, Key West, FL 33040
- 3 Beds
- 3 Baths
- 1,920 Sq Ft
- Built 2011
162 Sun Ln, Key West, FL 33040

Last Sold Summary
- 1% Above List Price
- $869/SF
- 126 Days On Market
Last Sold Price $1,669,000

Last Listing Agent Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

/29
$539,000
- 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
/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
/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 $592,835

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

9842 Leeward Ave, Key Largo, FL 33037

/43
Est $1,192,320 Not Listed For Sale

16 Eagle Dr, Key Largo, FL 33037
- 3 Beds
- 2 Baths
- 1,200 Sq Ft
- Built 2016
16 Eagle Dr, Key Largo, FL 33037

Last Sold Summary
- 2% Above List Price
- $975/SF
- 48 Days On Market
Last Sold Price $1,170,000

Last Listing Agent Yvette Doherty Coldwell Banker Schmitt Key Largo

/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
/33
$6,500 per month
- 3 Beds
- 2 Baths
- Property for Rent
18 W Circle Dr, Key West, FL 33040

This beautifully remodeled 3-bedroom, 2-bath stilted home sits canal-side behind Baby's Coffee, offering open water views and great opportunity. Built in 2000, it features a durable metal roof, impact windows, and sliding glass doors for comfort and great insurance options. Launch your boat from your own private ramp or use the community ramp nearby, then relax in the sparkling pool or tinker in

Dan Serban

Key West Luxury Real Estate Inc (KW)

(645) 205-0296

18 W Circle Dr, Key West, FL 33040
/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 $846,677

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

27417 Cayman Ln, Summerland Key, FL 33042

/57
Est $822,631 Not Listed For Sale

88500 Overseas Hwy Unit 502, Tavernier, FL 33070
- 3 Beds
- 2 Baths
- 1,567 Sq Ft
- Built 1976
88500 Overseas Hwy Unit 502, Tavernier, FL 33070

Last Sold Summary
- 3% Above List Price
- $508/SF
- 208 Days On Market
Last Sold Price $796,200

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

/20
$319,900
- 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
/53
$3,000,000 Sold Feb 19, 2026

78 Tingler Ln, Marathon, FL 33050
- 3 Beds
- 2 Baths
- 2,313 Sq Ft
- Built 1954
Last Sold Summary
- 32% Below List Price
- $1,297/SF
- 121 Days On Market
Current Estimated Value $3,869,156

Last Listing Agent Brenda Torrella Berkshire Hathaway HomeServices Keys Real Estate

78 Tingler Ln, Marathon, FL 33050

/32
Est $476,136 Not Listed For Sale

701 Spanish Main Dr Unit 609, Cudjoe Key, FL 33042
- 1 Bed
- Built 1988
701 Spanish Main Dr Unit 609, Cudjoe Key, FL 33042

Last Sold Summary
- 6% Above List Price
- $1,103/SF
- 256 Days On Market
Last Sold Price $450,000

Last Listing Agent Paul Rogers Coldwell Banker Schmitt RE Co.

Showing Results 1 - 40, Page 1 of 18

Florida Monroe County

How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Monroe County, FL Homes

Real Estate & Homes