Monroe County, FL Homes

/106
$9,999,000
- 5 Beds
- 4.5 Baths
- 4,622 Sq Ft
87 Cannon Royal Dr, Key West, FL 33040

Introducing an extraordinary and completely custom Polynesian-inspired estate designed by the owner with finishes imported from all over the world. Perfectly positioned on the most premier lot within the exclusive gated enclave of Shark Key, offering an exceptional blend of privacy and waterfront luxury. Set on a sprawling 1.56-acre lot with an impressive 850 feet of water frontage, this custom

Lisa Ferringo

Coldwell Banker Schmitt Real Estate Co

(786) 751-3198

87 Cannon Royal Dr, Key West, FL 33040
/7
$2,600 Per Month
- 2 Beds
- 1 Bath
- 1,380 Sq Ft
- Townhouse for Rent
50 Orange Dr Unit B, Key Largo, FL 33037

PARTIALLY FURNISHED 2 BEDROOM, 1 BATH DOWNSTAIRS UNIT OF SINGLE FAMILY HOME AVAILABLE NOW. WATER AND ELECTRICITY UP TO $145 INCLUDED IN RENT. LANDLORD ALSO INCLUDING WIFI/INTERNET. FRESHLY PAINTED, ALL TILE, IMPACT WINDOWS AND DOORS, NICE BACKYARD. PRIVATE HOMEOWNERS PARK WITH BEACH, PICNIC AREA, TIKI AND BOAT RAMP CLOSE BY. LOCATED AT MILE MARKER 100. VERY QUIET AND NEAR SCHOOLS, SHOPPING AND

Zachary Tranten

Keys Gate Realty, Inc.

(786) 947-5493

50 Orange Dr Unit B, Key Largo, FL 33037
/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 $739,115

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

16 Jewfish Ave, Key Largo, FL 33037

/47
Not Listed For Sale

88 2nd Ct, Key Largo, FL 33037
- 2 Beds
- 1.5 Baths
- 984 Sq Ft
- Built 1968
88 2nd Ct, Key Largo, FL 33037

Last Sold Summary
- 16 Days On Market

/45
$2,499,000

$300K PRICE DROP
- 2 Beds
- 2.5 Baths
- 2,124 Sq Ft
156 Sea Ln, Key West, FL 33040

Welcome to 156 Sea Lane, a residence that stands as a testament to architectural integrity and the vibrant history of the Florida Keys. This home was conceived and brought to life by its original owner, the legendary Reese Palley, who envisioned a sanctuary that combined the permanence of a fortress with the soul of an adventurer. Unlike the standard construction found throughout the islands, 156

Lisa Ferringo

Coldwell Banker Schmitt Real Estate Co

(855) 361-0652

156 Sea Ln, Key West, FL 33040
/29
Starting at $2,500 Per Month
- 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.

Coco Palms

(786) 640-1903

21585 Overseas Hwy, Cudjoe Key, FL 33042
/3
$2,600,000

Sold Mar 26, 2026

152 Giardino Dr, Islamorada, FL 33036
- 2 Beds
- 3 Baths
- 1,832 Sq Ft
- Built 1989
Last Sold Summary
- $1,419/SF
- 0 Days On Market
Current Estimated Value $2,612,152

Last Listing Agent Carolyn Ambler American Caribbean Real Estate, Christie's International Real Estate

152 Giardino Dr, Islamorada, FL 33036

/10
Est $174,975

Not Listed For Sale

23 Bonita Ave, Key Largo, FL 33037
23 Bonita Ave, Key Largo, FL 33037

Last Sold Summary
- 61 Days On Market

/55
$2,859,000

$40K PRICE DROP
- 3 Beds
- 3.5 Baths
- 2,286 Sq Ft
814 Ashe St, Key West, FL 33040

Built in 2008, this stunning 3-bedroom, 3.5-bath pool home perfectly blends the timeless character of classic Key West architecture with the comfort and convenience of modern construction. Ideally located just a short stroll from shops, restaurants, bars, and the world-famous Duval Street, this home offers the best of island living. Step inside to a bright, open-concept main living space with a

Lisa Ferringo

Coldwell Banker Schmitt Real Estate Co

(866) 972-3334

814 Ashe St, Key West, FL 33040
/2
$3,650 Per Month
- 3 Beds
- 2 Baths
- 1,380 Sq Ft
- House for Rent
50 Orange Dr Unit A, Key Largo, FL 33037

Beautifully furnised 3 bedroom, 2 bath upstairs unit of a single family home. This remodeled open floorplan is located near mile marker 100 and just a few blocks from the water. Private homeowners park with beach, picnic area, tiki and boat ramp. Owner including electricity and water up to $165 per month and internet/wifi. Downstairs unit also available (2/1) for additional price if larger unit

Zachary Tranten

Keys Gate Realty, Inc.

(786) 839-6008

50 Orange Dr Unit A, Key Largo, FL 33037
/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 $749,787

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

104500 Overseas Hwy Unit C301, Key Largo, FL 33037

/40
Est $1,674,447

Not Listed For Sale

110 Buttonwood Ln, Islamorada, FL 33036
- 3 Beds
- 2 Baths
- 1,290 Sq Ft
- Built 2025
110 Buttonwood Ln, Islamorada, FL 33036

Last Sold Summary
- 66 Days On Market

/62
$5,200,000
- 4 Beds
- 3.5 Baths
- 2,660 Sq Ft
17013 Coral Dr, Sugarloaf Key, FL 33042

Introducing Blue Sky Pointe - the crown jewel of Sugarloaf Key. Perched on a gated 33,750 sq. ft. peninsula with approximately 730 feet of waterfront, this spectacular 4 Bed, 3.5 Bath modern coastal showpiece is surrounded by glistening water and enjoys Keys famous sunset views over Sugarloaf Sound.Fully renovated with premium craftsmanship, the home features a standing seam metal roof, PGT

Lisa Ferringo

Coldwell Banker Schmitt RE Co.

(866) 531-8155

17013 Coral Dr, Sugarloaf Key, FL 33042
/35
Starting at $2,799 Per Month
- 1 - 3 Beds
10 Betty Rose Dr, Key West, FL 33040

Welcome to The Quarry, a residential community in Key West, FL featuring one, two, and three bedroom apartments. Spacious layouts welcome you home, along with exceptional service and an ideal location close to shopping, dining and entertainment.

The Quarry

(786) 933-4302

10 Betty Rose Dr, Key West, FL 33040
/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 $1,064,247

Last Listing Agent Jennifer Sylvia Keller Williams Key West Compass Realty

29490 Ranger Ave, Big Pine Key, FL 33043

/29
Est $680,786

Not Listed For Sale

3314 Northside Dr Unit 53, Key West, FL 33040
- 3 Beds
- 2 Baths
- 1,050 Sq Ft
- Built 1985
3314 Northside Dr Unit 53, Key West, FL 33040

Last Sold Summary
- 1 Day On Market

/76
$4,900,000

Under Contract
- 5 Beds
- 5 Baths
- 4,284 Sq Ft
116 Avenue G, Marathon, FL 33050

Nestled within the coveted Coco Plum neighborhood, this remarkable estate epitomizes luxury waterfront living in the heart of the Florida Keys. Meticulously crafted by D'asign Source, this custom home boasts an unparalleled blend of sophistication, comfort, and functionality while also offering some of the best deep-water boating in the Keys from 110' of canal frontage and rare deeded canal

Lisa Ferringo

Coldwell Banker Schmitt Real Estate Co

(833) 567-3628

116 Avenue G, Marathon, FL 33050
/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.

(786) 783-6791

129 Nautilus Dr, Islamorada, FL 33036
/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 $1,869,532

Last Listing Agent Yvette Doherty Coldwell Banker Schmitt Key Largo

272 Lower Matecumbe Rd, Key Largo, FL 33037

/37
Est $782,632

Not Listed For Sale

273 Hibiscus St, Tavernier, FL 33070
- 3 Beds
- 2 Baths
- 1,305 Sq Ft
- Built 1992
273 Hibiscus St, Tavernier, FL 33070

Last Sold Summary
- 140 Days On Market

/57
$3,295,000

$55K PRICE DROP Under Contract
- 4 Beds
- 4 Baths
- 2,649 Sq Ft
1240 Coury Dr, Key Colony Beach, FL 33051

This exquisite 4 Bedroom, 4 Bathroom residence has been completely reimagined into a stunning Coastal Modern masterpiece, designed to offer both serene vacation vibes and cutting-edge comfort. Set on an oversized 12,090 sq ft lot, this property boasts 61 feet of water frontage on a 75' wide canal, complete with 50 feet of deep water dockage and quick access to the ocean. The backyard is a true

Lisa Ferringo

Coldwell Banker Schmitt Real Estate Co

(833) 366-3885

1240 Coury Dr, Key Colony Beach, FL 33051
/20
Starting at $3,999 Per Month
- 2 Beds
28501 Channel View Dr, Little Torch Key, FL 33042

In Little Torch Key, near Mile Marker 28 on US Highway 1, Little Torch Cottages features 48 homes for those looking for something special. This beautiful property has 400 feet of open water views on Pine Channel, and also offers 22 foot boat slips at a discounted monthly rate for community residents. You will also be able to enjoy a community Clubhouse, park, BBQ areas, Paddle Board and Kayak

Little Torch Cottages

(786) 730-7736

28501 Channel View Dr, Little Torch Key, FL 33042
/21
$440,000

Sold Apr 10, 2026

10818 1st Avenue Gulf, Marathon, FL 33050
- 2 Beds
- 2 Baths
- 810 Sq Ft
- Built 1959
Last Sold Summary
- 2% Above List Price
- $543/SF
- 5 Days On Market
Current Estimated Value $429,430

Last Listing Agent Milly Perez Seafarer Realty LLC

10818 1st Avenue Gulf, Marathon, FL 33050

/3
Not Listed For Sale

Lot 24 Vacant Land, Big Torch Key, FL 33042
Lot 24 Vacant Land, Big Torch Key, FL 33042

Last Sold Summary
- 206 Days On Market

/72
$3,899,000

$100K PRICE DROP
- 3 Beds
- 3 Baths
- 2,096 Sq Ft
17015 Wahoo Ln W, Sugarloaf Key, FL 33042

Positioned on a rare west facing point lot with 270 ft of sparkling open water frontage on Sugarloaf Sound, this fully reimagined 3 Bedroom 3 Bathroom estate captures breathtaking sunset views across endless turquoise waters. Privately set on a gated 17,000 SF lot, the property lives like a private island compound framed by swaying palms, lush tropical landscaping, and the endless blue waters of

Lisa Ferringo

Coldwell Banker Schmitt Real Estate Co

(833) 754-7970

17015 Wahoo Ln W, Sugarloaf Key, FL 33042
/35
Starting at $2,393 Per Month
- Studio - 3 Beds
3900 S Roosevelt Blvd, Key West, FL 33040

Ocean Walk apartments are located on the peaceful Atlantic side of the island, nestled among lush natural vegetation, just steps away from the beach. Ideally located just minutes from the best dining, shopping and entertainment Key West has to offer, Ocean Walk Apartment Homes boast spacious one, two, and three bedroom apartments, spectacular views, and first-rate amenities. Each recently

Ocean Walk

(786) 971-2112

3900 S Roosevelt Blvd, Key West, FL 33040
/47
$811,000

Sold Mar 25, 2026

1254 James Ave, Marathon, FL 33050
- 3 Beds
- 2 Baths
- 1,152 Sq Ft
- Built 1971
Last Sold Summary
- 19% Below List Price
- $704/SF
- 96 Days On Market
Last Listing Agent Daniel Cloud Water Vista Realty, Inc.

1254 James Ave, Marathon, FL 33050

/44
Est $540,698

Not Listed For Sale

1215 97th St Unit 1, Marathon, FL 33050
- 2 Beds
- 2 Baths
- 1,143 Sq Ft
- Built 1967
1215 97th St Unit 1, Marathon, FL 33050

Last Sold Summary
- 284 Days On Market

/71
$1,499,999

$100K PRICE DROP
- 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
/18
Starting at $3,300 Per Month
- 2 Beds
5555 College Rd, Key West, FL 33040

Sunset Marina Apts

(786) 751-3820

5555 College Rd, 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 $878,121

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

27417 Cayman Ln, Summerland Key, FL 33042

/83
Est $3,053,956

Not Listed For Sale

230 Pescayo Ave, Marathon, FL 33050
- 4 Beds
- 3.5 Baths
- 2,939 Sq Ft
- Built 2020
230 Pescayo Ave, Marathon, FL 33050

Last Sold Summary
- 116 Days On Market

/101
$7,999,000

$500K PRICE DROP
- 4 Beds
- 4.5 Baths
- 4,888 Sq Ft
205 15th Cir, Key Colony Beach, FL 33051

Located within exclusive Key Colony Beach, nestled on a lushly landscaped, oversized lot, lies a stunning Oceanfront estate of unrivaled opulence. Boasting in-ground saltwater pool and spa, private sandy beach, firepit, built-in outdoor kitchen, and sprawling composite dock with 40K boat lift, this home caters to elevated Florida Keys living, and the 13,659 Sq. Ft. manicured lot across the street

Lisa Ferringo

Coldwell Banker Schmitt Real Estate Co

(877) 362-8411

205 15th Cir, Key Colony Beach, FL 33051
/20
Starting at $2,702 Per Month
- 1 - 2 Beds
21 1st Ave, Key Largo, FL 33037

Live in a tropical oasis where summer never ends at Playa Apartments in Key Largo. Surrounded by Old Florida Keys architecture and the ocean breeze, our community offers open-concept one- and two-bedroom homes with modern features and easy access to sun-soaked beaches and world-famous diving. Enjoy white sands at Harry Harris Park, explore John Pennekamp Coral Reef State Park, or dine along the

Playa Apartments

(844) 210-8152

21 1st Ave, Key Largo, FL 33037
/19
$870,000

Sold Mar 26, 2026

185 Gardenia St, Tavernier, FL 33070
- 2 Beds
- 1 Bath
- 891 Sq Ft
- Built 1959
Last Sold Summary
- 3% Below List Price
- $976/SF
- 14 Days On Market
Current Estimated Value $885,208

Last Listing Agent Gregory Sullivan BYOWNER.COM

185 Gardenia St, Tavernier, FL 33070

/28
Est $2,407,607

Not Listed For Sale

71 W Plaza Del Lago, Islamorada, FL 33036
- 4 Beds
- 3 Baths
- 2,082 Sq Ft
- Built 2011
71 W Plaza Del Lago, Islamorada, FL 33036

Last Sold Summary
- 202 Days On Market

/66
$32,500
- 2 Beds
- 2 Baths
- 1,120 Sq Ft
617 Front St Unit B-51 Penthouse Week, Key West, FL 33040

Top floor unit! Experience premium waterfront ownership with this deeded timeshare in the highly coveted building at the Galleon Resort. This unit offers one of the most beautiful Key West Sunsets at the resort.The residence boasts windows for abundant natural light and a balcony that maximizes the breathtaking waterfront setting. Enjoy front-row views as Coast Guard vessels and iconic pirate

Stephanie Herrmann

Truman & Co. (KW)

(645) 231-3562

617 Front St Unit B-51 Penthouse Week, Key West, FL 33040
/20
Starting at $2,548 Per Month
- 2 - 3 Beds
106003 Overseas Hwy, Key Largo, FL 33037

Whether you're looking to experience the turquoise waters and tropical landscapes that define Key Largo living for a little while or more. Keys Lake Villas welcomes you to a serene, vacation-style community at the gateway to the Florida Keys. Our townhomes offer spacious two or three-bedroom floor plans designed for comfort and pet-friendly living. Enjoy resort-inspired amenities and a relaxed

Keys Lake Villas

(786) 876-7291

106003 Overseas Hwy, Key Largo, FL 33037
/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 $4,349,396

Last Listing Agent Brenda Torrella Berkshire Hathaway HomeServices Keys Real Estate

78 Tingler Ln, Marathon, FL 33050

/26
Est $968,313

Not Listed For Sale

26 Shoreland Dr, Key Largo, FL 33037
- 3 Beds
- 2 Baths
- 832 Sq Ft
- Built 1974
26 Shoreland Dr, Key Largo, FL 33037

Last Sold Summary
- 83 Days On Market

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