Monroe County, FL Homes

/29
$695,000 Pending
- 3 Beds
- 2 Baths
- 1,359 Sq Ft
3729 Paula Ave, Key West, FL 33040

Unlock the potential of this prime property located in the highly sought-after New Town Key West. Situated on a spacious 5,500 sq ft lot, this single-level home offers over 1,300 sq ft of air-conditioned living space, including three bedrooms and a versatile sunroom that can serve as a fourth bedroom. With ample room for an in-ground pool, a full bath, and a half guest bath, this property is

Matthew Carlson

Realty ONE Group Destination

(786) 957-8965

3729 Paula Ave, Key West, FL 33040
/6
$4,000 per month
- 2 Beds
- 2 Baths
- 3,364 Sq Ft
- Apartment for Rent
26 S Exuma Rd Unit B, Key Largo, FL 33037

***Key Largo***Gorgeous and conveniently located, 2 BD/2BA with a private home feel. Unit located on 3rd floor. Only two apartments. Enjoy your morning coffee in the screened in balcony. Then head out on your boat with easy ocean access. 30' dock space. No cats allowed. More pictures to come.

Lizette Martin London Foster Realty

26 S Exuma Rd Unit B, Key Largo, FL 33037
/57
$796,200 Sold Mar 11, 2025

88500 Overseas Hwy Unit 502, Tavernier, FL 33070
- 3 Beds
- 2 Baths
- 1,567 Sq Ft
- Built 1976
Last Sold Summary
- 16% Below List Price
- $508/SF
- 208 Days On Market
Current Estimated Value $837,634

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

88500 Overseas Hwy Unit 502, Tavernier, FL 33070

/3
Not Listed For Sale
1008-1010 Gibraltar Rd, Key Largo, FL 33037

1008-1010 Gibraltar Rd, Key Largo, FL 33037

/35
$1,600,000
- 3 Beds
- 2 Baths
- 1,482 Sq Ft
204 La Paloma Rd, Key Largo, FL 33037

Charming, Private & Beautiful Canal-Front Pool Home! Your dream of owning a piece of paradise in the Florida Keys can become a reality.This fully remodeled gem features 3 bedrooms and 2 baths, (2/1 up 1/1 down) solid CBS construction including the roof, impact-resistant windows, a modern quartz-countertop kitchen with stainless steel appliances, and an inviting open living area and balcony

Terry Canto

American Caribbean Real Estate, Christie's International Real Estate

(786) 882-8132

204 La Paloma Rd, Key Largo, FL 33037
/27
$35,000 per month
- 4 Beds
- 4.5 Baths
- 5,348 Sq Ft
- House for Rent
133 Severino Dr, Islamorada, FL 33036

Experience luxury living at its finest in this completely renovated four-bedroom, four-bathroom home nestled in one of the most prestigious neighborhoods in the upper Keys. This stunning residence showcases exceptional craftsmanship by a renowned local builder, creating an extraordinary retreat where sophisticated design meets tropical paradise. The home features two separate living areas and

Pete Riveiro The Firm Realty Group

133 Severino Dr, Islamorada, FL 33036
/20
$1,200,000 Sold Apr 23, 2025

411 + 415 1st St, Big Coppitt, FL 33040
- 5 Beds
- 5 Baths
- 2,377 Sq Ft
- Built 1996
Last Sold Summary
- 7% Below List Price
- $505/SF
- 111 Days On Market
Last Listing Agent Christopher Scott,PA Expert Realty LLC (HQ)

411 + 415 1st St, Big Coppitt, FL 33040

/17
Not Listed For Sale
Lot 9 Avenida Primiceria, Marathon, FL 33050

Lot 9 Avenida Primiceria, Marathon, FL 33050

/72
$1,999,000
- 3 Beds
- 4 Baths
- 2,110 Sq Ft
1104 South St, Key West, FL 33040

ELEVATE YOUR QUALITY OF LIFE. Positioned within the highly sought-after Casa Marina district with unique design 1104 South St will appeal to those who demand the best in quality design, finishes, and lifestyle. The indoor-outdoor spaces are seamlessly connected by stack-away sliding-glass doors, promoting a flawless integration of outdoor/indoor living with architectural detailing that adds a

Tommy Mack

Coastal Collection Real Estate Inc.

(786) 207-1091

1104 South St, Key West, FL 33040
/36
$1,500 per month
- 1 Bed
- 1 Bath
- 450 Sq Ft
- Apartment for Rent
195 Gardenia St Unit 4, Tavernier, FL 33070

Great unit part of a unique canal front property in the heart of the Florida Keys, nestled in the sought-after Plantation Key Colony neighborhood. There is 30ft of dock space available for an additional monthly fee. The unit comes unfurnished. Water/Sewer/Trash are included. Coin Washer/Dryer on premises. Located just minutes from marinas, dining, and shopping. Sorry no pets.

Ada Rodriguez Better Homes and Gardens Real Estate Destinations

195 Gardenia St Unit 4, Tavernier, FL 33070
/27
$300,000 Sold Nov 26, 2025

27983 Snapper Ln, Little Torch Key, FL 33042
- 2 Beds
- 1 Bath
- 672 Sq Ft
- Built 1987
Last Sold Summary
- 9% Below List Price
- $446/SF
- 60 Days On Market
Last Listing Agent Sandra Dolowy KeyIsle Realty

27983 Snapper Ln, Little Torch Key, FL 33042

/2
Not Listed For Sale
Lot 8 Avenida Primiceria, Marathon, FL 33050

Lot 8 Avenida Primiceria, Marathon, FL 33050

/30
$769,000
- 3 Beds
- 3 Baths
- 1,596 Sq Ft
148 Sunrise Dr, Tavernier, FL 33070

Ideally located in the heart of Tavernier, this solid CBS home offers peace of mind with a concrete roof and impact windows. The permitted lower-level enclosure provides additional flexibility, while the main living area features a large, open-concept living, dining, and kitchen space, ideal for everyday living and entertaining. Step outside to a spacious, cleared backyard offering privacy with

Lorie LaLonde

American Caribbean Real Estate, Christie's International Real Estate

(833) 976-3186

148 Sunrise Dr, Tavernier, FL 33070
/27
$4,900 per month
- 3 Beds
- 2.5 Baths
- 1,804 Sq Ft
- House for Rent
94825 Overseas Hwy Unit 237, Key Largo, FL 33037

Only at Key Largo Ocean Resort can you be close to the bay and minutes from all. Your 1800+ ft luxury vacation property has been meticulously and elegantly presented with dramatic large living spaces, fabulous Chef’s kitchen, tile floors thru-out with lux master and spa bath. All-inclusive and fully equipped in every way imaginable with the best of everything to enjoy true resort style living.

Gustavo Lopez Village Realty of S. Florida

94825 Overseas Hwy Unit 237, Key Largo, FL 33037
/61
$2,550,000 Sold Jan 30, 2026

3620 Sunrise Dr, Key West, FL 33040
- 3 Beds
- 2 Baths
- 1,841 Sq Ft
- Built 1963
Last Sold Summary
- 4% Below List Price
- $1,385/SF
- 17 Days On Market
Last Listing Agent Zainya Zimmerer Berkshire Hathaway HomeServices Knight & Gardner Realty

3620 Sunrise Dr, Key West, FL 33040

/22
Est $1,408,238 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,550 Sq Ft
800 Fleming St Unit C1, Key West, FL 33040

800 Fleming St Unit C1, Key West, FL 33040

/39
$849,000 Under Contract
- 4 Beds
- 3 Baths
- 1,320 Sq Ft
11 Kestral Way, Key West, FL 33040

This updated 4-bedroom, 3-bathroom townhome in the gated Key West Golf Club community is a prime investment opportunity and active vacation rental. Offering privacy, comfort, and resort-style living, it's just minutes from downtown Key West, beaches, and world-class dining.Inside, an open, light-filled floor plan features crown molding, neutral tile flooring, and refined finishes. The

Austin Kimbler

Expert Realty LLC (HQ)

(833) 669-1452

11 Kestral Way, Key West, FL 33040
/42
$3,500 per month
- 2 Beds
- 2 Baths
- 726 Sq Ft
- House for Rent
325 Calusa St Unit 320, Key Largo, FL 33037

Key Largo Waterfront Paradise Awaits!Step into your dream escape with this stunning 2-bedroom, 2-bath, canal-front gem in the coveted Calusa subdivision. Panoramic open water views and direct access to the Florida Keys Bay. This community is your gateway to endless adventure and relaxation with activities like children playground, tennis & basketball court, pool and boat ramp & dock. The

Jose Vigo RE/MAX All Keys Real Estate

325 Calusa St Unit 320, Key Largo, FL 33037
/23
$650,000 Sold Dec 30, 2025

129 S Rd, Upper Matecumbe Key Islamorada, FL 33036
- 2 Beds
- 1 Bath
- 882 Sq Ft
- Built 1958
Last Sold Summary
- 27% Below List Price
- $737/SF
- 118 Days On Market
Last Listing Agent Wiebke Westedt LoKation Real Estate

129 S Rd, Upper Matecumbe Key Islamorada, FL 33036

/2
Est $515,116 Not Listed For Sale
- 2 Beds
- 2 Baths
- 804 Sq Ft
3930 S Roosevelt Blvd Unit W410, Key West, FL 33040

3930 S Roosevelt Blvd Unit W410, Key West, FL 33040

/34
$819,000
- 4 Beds
- 2 Baths
- 1,496 Sq Ft
102 Harry Harris Dr, Tavernier, FL 33070

Legal Duplex, Two electric meters, Two water meters, with two mailboxes and plenty of parking. Concrete building with metal roof. Both apartments have been nicely updated inside & out. Mini split AC's with tankless water heaters. Each apartment is 748 sq. ft. Downstairs is rented at $2,450.00 Upstairs is vacant to show & sell !! was asking$$2,650.00 per month. Washer & Dryer in Storage building

Tom Rodriguez

American Caribbean Real Estate, Christie's International Real Estate

(877) 630-3394

102 Harry Harris Dr, Tavernier, FL 33070
/44
$5,800 per month
- 3 Beds
- 3 Baths
- 1,300 Sq Ft
- Property for Rent
228 Orchid St, Tavernier, FL 33070

Introducing a 3/2 home located in the serene Tavernier. this hideaway is situated in a tranquil block with only a few properties providing you with the perfect opportunity to comfort of a home with a fully furnished open plan living area, well-equipped kitchen, the location is unbeatable, the property is walking distance, to the mall, and hospital,all local shops, supermarkets. Make the most

Iliana Hernandez Urban Investments Realty LLC

228 Orchid St, Tavernier, FL 33070
/101
$4,700,000 Sold Feb 21, 2025

29433 Enterprise Ave, Big Pine Key, FL 33043
- 4 Beds
- 5 Baths
- 3,727 Sq Ft
- Built 2007
Last Sold Summary
- 6% Below List Price
- $1,261/SF
- 25 Days On Market
Current Estimated Value $4,750,677

Last Listing Agent Lisa Swanson The Agency Florida Keys

29433 Enterprise Ave, Big Pine Key, FL 33043

/32
Not Listed For Sale
- 3 Beds
- 3 Baths
- 1,680 Sq Ft
84745 Old Hwy Unit 11, Islamorada, FL 33036

84745 Old Hwy Unit 11, Islamorada, FL 33036

/75
$4,500,000
- 3 Beds
- 4 Baths
- 4,200 Sq Ft
421 La Fitte Rd, Little Torch Key, FL 33042

An extraordinary waterfront offering in Little Torch Key, representing the highest level of design, construction, and lifestyle in the Lower Florida Keys. Designed and built by premier builder D'Asign Source, this poured-concrete residence is set on a rare double waterfront lot with expansive Pine Channel views and direct access to world-class boating, fishing, and diving. Approximately 4,000 sq

Sandra Tuttle

Island Welcome Real Estate

(305) 923-9161

421 La Fitte Rd, Little Torch Key, FL 33042
/42
$5,490 per month
- 2 Beds
- 2 Baths
- 816 Sq Ft
- House for Rent
31547 Avenue D, Big Pine Key, FL 33043

Come see this immaculate 2 Bedroom 2 Bath Big Pine Key Waterfront home with its Wonderful Water Views! It is available for a seasonal rental, so come on down and enjoy the Florida winter weather! It has a well equipped kitchen for your convenience and is only 5 years old. Please see the attached photos. You'll be glad you did! Only 30 miles to Key West and all of the other Points of Interest in

Philip Vias LoKation

31547 Avenue D, Big Pine Key, FL 33043
/2
$55,000 Sold Oct 22, 2025

Lot 2 Rainbow Beach, Big Torch Key, FL 33042
- Land
Last Sold Summary
- 4% Below List Price
- 2 Days On Market
Last Listing Agent Pamela Stangler Expert Realty LLC

Lot 2 Rainbow Beach, Big Torch Key, FL 33042

/28
Not Listed For Sale
130 Overseas Hwy, Islamorada, FL 33036

130 Overseas Hwy, Islamorada, FL 33036

/43
$1,999,000
- 3 Beds
- 2 Baths
- 1,666 Sq Ft
1659 Long Beach Dr, Big Pine Key, FL 33043

Experience refined coastal living at this newly renovated oceanfront residence on prestigious Long Beach Drive in Big Pine Key. Perfectly positioned along a rare stretch of natural shoreline, this property offers an expansive private sandy beach that feels like your own secluded escape, paired with sweeping sunrise to sunset views over the Atlantic Ocean. This 3 bedroom, 2 bathroom home showcases

Lisa Ferringo

Coldwell Banker Schmitt Lower Keys (KW)

(888) 389-9201

1659 Long Beach Dr, Big Pine Key, FL 33043
/57
$14,000 per month
- 5 Beds
- 4 Baths
- 6,252 Sq Ft
- Apartment for Rent
112 Avenue D Unit 1, Marathon, FL 33050

Experience coastal living at its finest in this brand-new luxury home in the heart of Marathon, Florida. Blending modern elegance with island charm, this residence offers 110 feet of direct water frontage and immediate ocean access, perfect for boating, fishing, and soaking in the views. Enjoy an open-concept layout with designer finishes, a chef’s kitchen with quartz countertops and premium

Andres Cepero Element Real Estate Group

112 Avenue D Unit 1, Marathon, FL 33050
/27
$492,000 Sold Mar 03, 2025

115 Harbor Dr, Key Largo, FL 33037
- 2 Beds
- 1 Bath
- 1,046 Sq Ft
- Built 1955
Last Sold Summary
- 9% Below List Price
- $470/SF
- 75 Days On Market
Current Estimated Value $540,076

Last Listing Agent Christy Hughes Coldwell Banker Schmitt Islamorada

115 Harbor Dr, Key Largo, FL 33037

/2
Not Listed For Sale
- 2 Beds
- 1 Bath
- 672 Sq Ft
170 Mars Ln, Key West, FL 33040

170 Mars Ln, Key West, FL 33040

/22
$3,199,000 Open Sun 11:15AM - 1PM
- 4 Beds
- 3 Baths
- 2,334 Sq Ft
158 Bahama Ave, Key Largo, FL 33037

It's Better on Bahama Ave! This stunning 4-bedroom, 3-bath waterfront residence located in the prestigious Port Largo subdivision of Key Largo, offering 75 feet of private dockage with easy boating access to the Atlantic Ocean. Enter through the custom-designed electric gate to discover a fully contained, completely remodeled home with upscale finishes and thoughtful design throughout, capturing

Carolyn Ambler

American Caribbean Real Estate, Christie's International Real Estate

(786) 822-7369

158 Bahama Ave, Key Largo, FL 33037
/9
$2,500 per month
- 2 Beds
- 1 Bath
- 875 Sq Ft
- Apartment for Rent
184 Adobe Casa Court Dr Unit 184, Tavernier, FL 33070

Find your perfect Keys retreat in this fully renovated 2-bedroom, 1-bath home in the heart of Tavernier. Bright, breezy, and beautifully updated, this property offers open living spaces, a modern kitchen, and a fresh contemporary bath. Step outside and enjoy tropical landscaping, nearby water access, and everything the Upper Keys has to offer—great dining, diving, and sunsets just minutes away.

George Daniel Brokers International Realty LLC

184 Adobe Casa Court Dr Unit 184, Tavernier, FL 33070
/19
$315,000 Sold Dec 05, 2025

201 Coppitt Rd Unit 106, Key West, FL 33040
- 1 Bed
- 1 Bath
- 536 Sq Ft
- Built 1974
Last Sold Summary
- 3% Below List Price
- $588/SF
- 14 Days On Market
Last Listing Agent Jaime Caballero Key West Vacation Properties & Realty, LLC (KW)

201 Coppitt Rd Unit 106, 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

/12
$789,900
- Land
0 Dominica Ln Unit 615842, Ramrod Key, FL 33042

Gorgeous Open Ocean location totaling 4 lots, boasting over a quarter acre of land with sheltered canal and private beach; an incredible investment opportunity! Build your dream home in paradise with a transferable building right, which are readily available on the market and provide an easy path to development. This unique opportunity is in the ideal location, on one of the last remaining Open

Lisa Ferringo

Coldwell Banker Schmitt Lower Keys (KW)

(786) 744-6884

0 Dominica Ln Unit 615842, Ramrod Key, FL 33042
/11
$3,000 per month
- 2 Beds
- 2 Baths
- 630 Sq Ft
- Property for Rent
65821 Overseas Hwy Unit 105, Long Key, FL 33001

6+/- Month Rental--Come Fall in Love with this Little Gem nestled in the heart of Outdoor Resort. This vibrant gated community waterfront resort sits on 35 acres and has multiple amenities such as Pool, marina, boat ramp, boat trailer storage, private beach, bocce ball, tennis courts, club house, Laundry Facilities and more! Whether you're seeking relaxation or recreation, this resort has it

Tracey Petrusha Venture Realty Group

65821 Overseas Hwy Unit 105, Long Key, FL 33001
/23
$850,000 Sold Oct 31, 2025

308 Peacon Ln, Key West, FL 33040
- 3 Beds
- 3 Baths
- 1,296 Sq Ft
- Built 1923
Last Sold Summary
- 43% Below List Price
- $656/SF
- 299 Days On Market
Current Estimated Value $856,223

Last Listing Agent Vic Musmanno Coldwell Banker Schmitt Real Estate Co. (KW)

308 Peacon Ln, Key West, FL 33040

/44
Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,232 Sq Ft
81200 Overseas Hwy Unit 5, 6, Islamorada, FL 33036

81200 Overseas Hwy Unit 5, 6, Islamorada, FL 33036

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