Monroe County, FL Homes

/35
$199,000
- Land
55 Boca Chica Rd Unit 53, Key West, FL 33040

Welcome to Seaside Resort, a gated waterfront community just 10 minutes from the heart of Key West. This RV lot offers the perfect option for a full time setup or a seasonal home base between travels, with the added flexibility to generate rental income when not in use. The property features a beautifully landscaped courtyard that creates a private outdoor retreat, ideal for relaxing evenings

Lisa Ferringo

Coldwell Banker Schmitt Lower Keys (KW)

(645) 218-6631

55 Boca Chica Rd Unit 53, Key West, FL 33040
/24
$5,500 per month
- 2 Beds
- 3 Baths
- Property for Rent
25 Kingfisher Ln, Key West, FL 33040

Beautiful 2 bed 2 bath ensuite home available in the gated community of the Key West Colf Club in Key West. Fully furnished. Half bath and laundry located on the first floor. Spectacular views of the golf course with covered wrap around porches and plenty of parking. Located on a cul-de-sac. Community pools and fitness room located on-site.

Michael Petro Expert Realty LLC (HQ)

25 Kingfisher Ln, Key West, FL 33040
/45
$1,550,000 Sold Jan 30, 2026

28538 John Silver Rd, Summerland Key, FL 33042
- 3 Beds
- 2 Baths
- 1,248 Sq Ft
- Built 1981
Last Sold Summary
- 3% Below List Price
- $1,242/SF
- 164 Days On Market
Last Listing Agent Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

28538 John Silver Rd, Summerland Key, FL 33042

/66
Est $3,389,726 Not Listed For Sale
- 4 Beds
- 4 Baths
- 2,057 Sq Ft
28 Aster Terrace, Key West, FL 33040

28 Aster Terrace, Key West, FL 33040

/63
$4,450,000
- 4 Beds
- 3.5 Baths
- 3,479 Sq Ft
362 E Seaview Dr, Marathon, FL 33050

If you're searching for the look, feel, and scent of brand-new construction--complete with soaring vaulted ceilings--on exclusive Duck Key, this is the one.This solid concrete waterfront home has been completely reimagined from top to bottom by the current owner, with no expense spared and uncompromising attention to detail throughout. Every major system and finish is brand new, including

Shane Wilson

Cypress Realty, Inc.

(305) 770-6567

362 E Seaview Dr, Marathon, FL 33050
/38
$7,200 per month
- 2 Beds
- 3 Baths
- 1,345 Sq Ft
- Condo for Rent
629 Elizabeth St Unit ID1297833P, Key West, FL 33040

Casa Azul is a luxurious modern cottage featuring an open-concept living area that is bathed in natural sunlight. Enjoy a dip in the heated saltwater plunge pool with a waterfall feature and night lighting. Located in Old Town Key West, just two blocks from Duval Street, this pet-friendly home offers private parking and is perfect for your next extended stay.Casa Azul perfectly blends comfort

629 Elizabeth St Unit ID1297833P, Key West, FL 33040
/44
$630,000 Sold Jun 16, 2025

130 Ocean View Dr, Tavernier, FL 33070
- 3 Beds
- 1 Bath
- 1,312 Sq Ft
- Built 1984
Last Sold Summary
- 13% Below List Price
- $480/SF
- 158 Days On Market
Current Estimated Value $670,899

Last Listing Agent Taylor Engel Coldwell Banker Schmitt R.E.

130 Ocean View Dr, Tavernier, FL 33070

/22
Est $641,875 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,080 Sq Ft
30876 Malaga Ln, Big Pine Key, FL 33043

30876 Malaga Ln, Big Pine Key, FL 33043

/49
$1,499,000 Pending
- 4 Beds
- 4 Baths
- 3,298 Sq Ft
132 N Indies Dr, Marathon, FL 33050

Experience the best of the Florida Keys in this beautifully designed 4-bedroom, 4-bath home in the sought-after Duck Key community. This waterfront property boasts an open floor plan, seamlessly blending indoor and outdoor living. The spacious kitchen features ample counter space, perfect for entertaining.Enjoy breathtaking canal views from the covered balcony, or step outside to your private

Matthew Sheehan

Ocean Sotheby's International Realty

(786) 981-5471

132 N Indies Dr, Marathon, FL 33050
/22
$3,600 per month
- 2 Beds
- 2 Baths
- 1,056 Sq Ft
- House for Rent
201 Cutthroat Dr, Summerland Key, FL 33042

LONG TERM RENTAL AVAILABLESpacious and well maintained unfurnished 2-BD, 2-BTH Stilted home for rent in Cudjoe Key. It has stainless steel appliances (stove/oven is brand new), and the Main Bedroom has it's own porch.A large deck overlooks the canal and is perfect for an evening adult beverage. This property is situated at the corner of Cutthroat Dr. and Blackbeard Ln. and has a large concrete

Mark Peterson

201 Cutthroat Dr, Summerland Key, FL 33042
/26
$295,000 Sold Jan 08, 2026

6099 Overseas Hwy Unit 13E, Marathon, FL 33050
- 1 Bed
- 1 Bath
- 650 Sq Ft
- Built 1976
Last Sold Summary
- 15% Below List Price
- $454/SF
- 90 Days On Market
Last Listing Agent Casey Elliott Key Colony Beach Realty

6099 Overseas Hwy Unit 13E, Marathon, FL 33050

/52
Est $1,163,203 Not Listed For Sale
- 2 Beds
- 3 Baths
- 930 Sq Ft
1348 Ocean Dr, Summerland Key, FL 33042

1348 Ocean Dr, Summerland Key, FL 33042

/27
$987,500
- 4 Beds
- 2 Baths
- 1,536 Sq Ft
3962 No Name Rd, Big Pine Key, FL 33043

Waterfront DUPLEX ~ CBS Construction 4BD/2BA with 2BD|1BA on each side. Property features, excellent boating access, full 70' concrete seawall, covered porch for both units, tile flooring, accordion shutters, separate utility/laundry rooms on each side, 2 central AC units and 2 electric meters. Newer metal roof within 2 years. Fenced yard with room to park your boat trailer. Great investment

Stacy Shahan

Island Real Estate Company Florida Keys

(888) 275-1086

3962 No Name Rd, Big Pine Key, FL 33043
/14
$4,000 per month
- 2 Beds
- 1 Bath
- 612 Sq Ft
- Condo for Rent
2513 Staples Ave Unit B, Key West, FL 33040

Property Id: 1836419This is the rear unit in a super cute ground level duplex in midtown. 2 bed/1 bath. One off-street parking spot. Shared yard. In unit laundry. Updated appliances. Clean and easy to maintain. Utilities and exterior maintenance included. Great for roommates or small families. Current renters are active military and are being redeployed elsewhere.

2513 Staples Ave Unit B, Key West, FL 33040
/64
$3,000,000 Sold May 16, 2025

51 Sunset Key Dr, Key West, FL 33040
- 3 Beds
- 3 Baths
- 1,920 Sq Ft
- Built 2005
Last Sold Summary
- 19% Below List Price
- $1,562/SF
- 254 Days On Market
Current Estimated Value $3,276,904

Last Listing Agent Cardenas & Krug Team Coastal Collection Real Estate Inc.

51 Sunset Key Dr, Key West, FL 33040

/22
Est $558,086 Not Listed For Sale
- 2 Beds
- 1 Bath
- 1,594 Sq Ft
1133 Division St, Big Pine Key, FL 33043

1133 Division St, Big Pine Key, FL 33043

/47
$1,099,000
- 3 Beds
- 3 Baths
- 1,344 Sq Ft
29051 Magnolia Ln, Big Pine Key, FL 33043

Welcome to 29051 Magnolia Ln, Big Pine Key, FL! This home offers a 2-bedroom, 2-bath main area and a pre-FIRM permitted 480 sq. ft. studio/MIL suite with a full bath. Nestled on a 5,100 sq. ft. lot, this concrete home is ideal for island living. The chef's kitchen features stainless steel appliances, premium counters, and breakfast bar. Enjoy a screened porch overlooking the canal, complete with

Yvette Toledo-Baste

Compass Florida, LLC

(866) 971-5749

29051 Magnolia Ln, Big Pine Key, FL 33043
/18
$3,350 per month
- 2 Beds
- 1.5 Baths
- 976 Sq Ft
- House for Rent
2 Bonefish Ave, Key Largo, FL 33037

PERFECTION in Key Largo. Designer finishes , include oversized porcelain tile and engineered hardwood cherry flooring, granite counter tops & stainless steel appliances, European style white kitchen cabinetry , plantation shutter window treatments, French doors, impact windows, Full-size front loader washer and dryer, Expansive paved driveway fits 3 cars plus, large side space with sun canopy

Sophia Lima Limar Realty, LLC

2 Bonefish Ave, Key Largo, FL 33037
/24
$735,000 Sold Jul 02, 2025

19 Whistling Duck Ln, Key West, FL 33040
- 3 Beds
- 3 Baths
- 1,060 Sq Ft
- Built 1995
Last Sold Summary
- 18% Below List Price
- $693/SF
- 98 Days On Market
Current Estimated Value $771,752

Last Listing Agent Kelli Houze Berkshire Hathaway HomeServices Knight & Gardner Realty

19 Whistling Duck Ln, Key West, FL 33040

/41
Est $2,267,652 Not Listed For Sale
- 3 Beds
- 4 Baths
- 3,056 Sq Ft
20864 4th Ave W, Summerland Key, FL 33042

20864 4th Ave W, Summerland Key, FL 33042

/50
$689,000
- 3 Beds
- 2 Baths
- 1,593 Sq Ft
88181 Old Hwy Unit G21, Islamorada, FL 33036

Enjoy resort-style living in this spacious, fully furnished 3-bedroom, 2-bath condominium located in the exclusive Coral Harbour Club. This residence features an open and airy floor plan where the kitchen, dining, and living areas blend seamlessly, creating an inviting space ideal for both relaxing and entertaining.The primary suite offers privacy and comfort with a modern en-suite bathroom

Pierre Bellion

Ocean Sotheby's International Realty

(866) 764-5429

88181 Old Hwy Unit G21, Islamorada, FL 33036
/20
$28,733 per month
- 5 Beds
- 5.5 Baths
- 2,992 Sq Ft
- Condo for Rent
247 Pescayo Ave Unit ID1325585P, Marathon, FL 33050

Feel at home in this luxurious 5-bedroom, 5.5-bath waterfront getaway in Marathon, FL. This brand-new home offers an elevator for easy access to all floors.This home features an open-concept living area, a fully equipped indoor kitchen and an outdoor kitchen, high-speed Wi-Fi, and a 70-foot dock. The living room offers a comfortable leather sectional with cup holders, pillows, throw blankets,

247 Pescayo Ave Unit ID1325585P, Marathon, FL 33050
/43
$735,000 Sold Jan 05, 2026

1 Orange Dr, Key Largo, FL 33037
- 4 Beds
- 3 Baths
- 1,652 Sq Ft
- Built 2025
Last Sold Summary
- 3% Below List Price
- $445/SF
- 2 Days On Market
Last Listing Agent Terry Canto American Caribbean Real Estate, Christie's International Real Estate

1 Orange Dr, Key Largo, FL 33037

/69
Est $2,008,965 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 1,494 Sq Ft
1017 Eaton St, Key West, FL 33040

1017 Eaton St, Key West, FL 33040

/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
/26
$5,000 per month
- 3 Beds
- 2 Baths
- 912 Sq Ft
- Property for Rent
2401 Patterson Ave Unit 101, Key West, FL 33040

Spacious 3BD/2BA - Renovated First-Floor Duplex in MidtownThis fully renovated 3-bedroom, 2-bath apartment offers everything you need for comfortable long-term living in Key West's Midtown neighborhood. Located on the first floor of a freshly updated duplex, this home features a large open-concept living area and kitchen with all new appliances and high-end finishes. The unit includes a brand-new

Jody Clark Key West Luxury Real Estate Inc (KW)

2401 Patterson Ave Unit 101, Key West, FL 33040
/20
$190,000 Sold Feb 27, 2025

28597 Peg Leg Rd, Little Torch Key, FL 33042
- Land
Last Sold Summary
- 5% Below List Price
- 80 Days On Market
Last Listing Agent Tylon Fraley Southeast Realty Equities, Inc

28597 Peg Leg Rd, Little Torch Key, FL 33042

/44
Est $3,374,202 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,360 Sq Ft
1221 Johnson St, Key West, FL 33040

1221 Johnson St, Key West, FL 33040

/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
/20
$5,178 per month
- 2 Beds
- 2 Baths
- 1,194 Sq Ft
- Condo for Rent
120 Angela St Unit ID1384034P, Key West, FL 33040

Feel at home in this bright, modern 2-bedroom, 2-bath second-floor condo, ideal for comfortable long-term stays in Key West.Fully renovated in Summer 2024, the condo features an open-concept living area and a modern kitchen with new countertops, stainless steel appliances, and all home cooking essentials. Outside, relax by the shared heated pool or unwind in the grill and lounge area

120 Angela St Unit ID1384034P, Key West, FL 33040
/66
$688,000 Sold Feb 14, 2025

97652 Overseas Hwy Unit 11, Key Largo, FL 33037
- 2 Beds
- 1.5 Baths
- 1,420 Sq Ft
- Built 1975
Last Sold Summary
- 7% Below List Price
- $485/SF
- 115 Days On Market
Last Listing Agent Terri Bodker LoKation Real Estate

97652 Overseas Hwy Unit 11, Key Largo, FL 33037

/48
Est $1,392,568 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,926 Sq Ft
11295 3rd Avenue Gulf, Marathon, FL 33050

11295 3rd Avenue Gulf, 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
/43
$5,300 per month
- 3 Beds
- 2 Baths
- 1,170 Sq Ft
- House for Rent
11 Flamingo Rd, Key Largo, FL 33037

Fully furnished 3-bedroom, 2-bath waterfront home offering easy access to open water via a deep-water canal. Private dock suitable for boat(s), jet skis, kayaks, and water toys. Just 3 minutes to the Gulf and approximately 20 minutes to the Atlantic Ocean by water.Dock accommodates vessels up to 10,000 lbs and no longer than 30 feet. Boat access is subject to owner approval. Tenants with a boat

Flor Mendez Realty One Group Evolution

11 Flamingo Rd, Key Largo, FL 33037
/3
$290,000 Sold Aug 29, 2025

351 46th St, Marathon, FL 33050
- 2 Beds
- 2 Baths
- 768 Sq Ft
- Built 1993
Last Sold Summary
- 23% Below List Price
- $378/SF
- 413 Days On Market
Last Listing Agent Bill Wilkinson RE/MAX Keys To The Key

351 46th St, Marathon, FL 33050

/18
Est $1,685,729 Not Listed For Sale
- 7 Beds
- 4 Baths
- 3,538 Sq Ft
17042 Starfish Ln W, Summerland Key, FL 33042

17042 Starfish Ln W, Summerland Key, FL 33042

/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
/25
$4,540 per month
- 1 Bed
- 1 Bath
- 419 Sq Ft
- Condo for Rent
817 Terry Ln Unit ID1297837P, Key West, FL 33040

"Lil Bit" is a rare find in the historic Bahama Village neighborhood. This classic "conch" home is modern and renovated to have an elevated feel but retains the charm and character of old Key West. Perfect for a couple or visitors looking for a monthly stay, this home is equipped with everything you need. While it is a "Lil Bit," the space feels large, open, and fresh, and is a short walk to Fort

817 Terry Ln Unit ID1297837P, Key West, FL 33040
/2
$978,200 Sold Oct 03, 2025

132 Riviera Dr, Islamorada, FL 33070
- 4 Beds
- 3 Baths
- 1,943 Sq Ft
- Built 2025
Last Sold Summary
- 2% Below List Price
- $503/SF
- 67 Days On Market
Current Estimated Value $991,034

Last Listing Agent Brent Baris COMMERCIAL PROPERTY BROKERS

132 Riviera Dr, Islamorada, FL 33070

/45
Est $803,490 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,408 Sq Ft
461 Barracuda Blvd, Key Largo, FL 33037

461 Barracuda Blvd, Key Largo, FL 33037

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