Monroe County, FL Homes

/19
$1,299,000
- 7 Beds
- 4 Baths
- 2,699 Sq Ft
1614 Dennis St, Key West, FL 33040

Investment Opportunity - Income-Producing Triplex!Don't miss this excellent income-producing triplex located in a convenient, high-demand area close to schools, shopping, dining, parks, and just minutes from downtown Key West. Whether you're looking to expand your investment portfolio or occupy one unit while generating rental income from the others, this property offers outstanding

Matthew Sheehan

Ocean Sotheby's International Realty

1614 Dennis St, Key West, FL 33040
/56
$18,000 Per Month
- 4 Beds
- 2 Baths
- 1,935 Sq Ft
- House for Rent
57967 Morton St, Marathon, FL 33050

Welcome to ''Casa Azul Villa'', a beautifully renovated Gulf-front retreat available as a fully furnished, turn-key long-term rental in the peaceful enclave of Grassy Key.Privately tucked away on quiet Morton Street, this waterfront home offers sweeping open water Gulf views, exceptional boating access, and the relaxed coastal lifestyle the Florida Keys are known for. With no highway noise and a

Melissa Gibbins Expert Realty LLC (HQ)

57967 Morton St, Marathon, FL 33050
/15
$562,500

Sold May 22, 2026

712 Galveston Ln Unit 1, Key West, FL 33040
- 1 Bed
- 1 Bath
- 526 Sq Ft
- Built 1981
Last Sold Summary
- 2% Below List Price
- $1,069/SF
- 9 Days On Market
Current Estimated Value $571,199

Last Listing Agent Sean Farrer Coldwell Banker Schmitt RE Co

712 Galveston Ln Unit 1, Key West, FL 33040

/16
Not Listed For Sale

108 Caribbean Ave, Key Largo, FL 33037
- 4 Beds
- 2 Baths
- 1,686 Sq Ft
- Built 1980
108 Caribbean Ave, Key Largo, FL 33037

Last Sold Summary
- 66 Days On Market

/63
$1,095,000

$100K PRICE DROP
- 3 Beds
- 2 Baths
- 1,720 Sq Ft
2309 Flagler Ave, Key West, FL 33040

Nestled within a private tropical oasis on a 7,500-square-foot lot, this charming Mid-Century Modern home offers the perfect blend of architectural character and island living. Approximately 64 feet of floor-to-ceiling sliders and windows fill the home with natural light and frame lush garden views from nearly every room.The three-bedroom, two-bath floor plan features clean modern lines,

Jennifer Newman

Truman & Co. (KW)

2309 Flagler Ave, Key West, FL 33040
/31
$2,150 Per Month
- 1 Bed
- 1 Bath
- 649 Sq Ft
- House for Rent
4 Transylvania Ave Unit B, Key Largo, FL 33037

Available immediately! Your Key Largo pet friendly and boat friendly retreat awaits! Offered unfurnished but can also be furnished. Freshly painted 1-bedroom, 1-bath single-family home located in a desirable neighborhood with access to a private homeowner's park featuring a boat ramp and beach within walking distance. Amazing location walking distance to wonderful oceanfront restaurants. Updated

Lina Carrera Carrera Consulting Group Inter

4 Transylvania Ave Unit B, Key Largo, FL 33037
/4
$160,000

Sold Jul 08, 2026

Dock Dock Harbor Village Dr Unit SLIP 18, Duck Key, FL 33050
- Built 2000
Last Sold Summary
- 11% Below List Price
- 0 Days On Market
Last Listing Agent Margaret Crowley Florida Keys Realty Group LLC

Dock Dock Harbor Village Dr Unit SLIP 18, Duck Key, FL 33050

/2
Est $732,214

Not Listed For Sale

7600 Ocean Terrace, Marathon, FL 33050
- 3 Beds
- 2 Baths
- 1,170 Sq Ft
- Built 2003
7600 Ocean Terrace, Marathon, FL 33050

Last Sold Summary
- 41 Days On Market

/22
$619,000
- 1 Bed
- 1 Bath
- 640 Sq Ft
804 South St Unit 3, Key West, FL 33040

This is a must see unique and airy tropical second story condo in the Southpark Condominium Association. Lush vegetation surrounds the property and the private pool area located in the beautiful Casa Marina neighborhood. This upstairs one Bedroom/ one Bathroom condo offers relaxation on either the front covered porch or the rear private deck with a motorized awning for your comfort and

J. Michael Caron

Keller Williams Key West Compass Realty

804 South St Unit 3, Key West, FL 33040
/21
$2,200 Per Month
- 2 Beds
- 1.5 Baths
- 950 Sq Ft
- Condo for Rent
92550 Overseas Hwy Unit 202, Tavernier, FL 33070

Available for annual lease, this unfurnished 2-bedroom, 1.5-bath second-floor condo is located in a bayfront community at MM 92 in Tavernier. The unit features a full kitchen, open living and dining area, and two porches with bay views. Community amenities include a bayfront beach area (dockage is not available), on-site coin-operated laundry, and first-come, first-served parking. Tenant is

Natalie Bevis Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

92550 Overseas Hwy Unit 202, Tavernier, FL 33070
/125
$5,000,000

Sold Jun 18, 2026

24200 Overseas Hwy, Summerland Key, FL 33042
- 5 Beds
- 5.5 Baths
- 3,000 Sq Ft
- Built 1977
Last Sold Summary
- 19% Below List Price
- $1,667/SF
- 106 Days On Market
Current Estimated Value $4,618,358

Last Listing Agent Sylvia Werling Keller Williams Key West Compass Realty

24200 Overseas Hwy, Summerland Key, FL 33042

/40
Est $1,681,196

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

/22
$685,000

$29K PRICE DROP Under Contract
- 2 Beds
- 1 Bath
- 768 Sq Ft
4039 Egret Ln, Summerland Key, FL 33042

Charming 2 bed, 1 bath home in Big Torch Key featuring hardiplank siding, impact windows throughout, and a metal roof. The 12,000 sq ft lot offers 120 ft of waterfront, including 60 ft along the canal cleared for dockage. The spacious yard provides room to add a pool, tiki hut, outdoor entertaining areas, and still have ample space for boat, trailer or RV parking. Located on a deep-water canal

Sandra Tuttle

Island Welcome Real Estate

4039 Egret Ln, Summerland Key, FL 33042
/6
$1,650 Per Month
- 1 Bath
- Apartment for Rent
103365 Overseas Hwy Unit C, Key Largo, FL 33037

End Unit C Newly Remodeled Studio Apartment featuring all Brand-New Black Appliances. Conveniently located close to shopping, schools, restaurants, and more. Move -In Ready.

Tracey Petrusha LoKation

103365 Overseas Hwy Unit C, Key Largo, FL 33037
/29
$377,500

Sold Nov 20, 2025

119 Cortez Dr Unit 1G, Islamorada, FL 33036
- 1 Bed
- 1 Bath
- 518 Sq Ft
- Built 1980
Last Sold Summary
- 2% Below List Price
- $729/SF
- 24 Days On Market
Last Listing Agent Krissy Carnahan Paradise Florida Keys Real Estate, a Luxury Brand

119 Cortez Dr Unit 1G, Islamorada, FL 33036

/46
Not Listed For Sale

701 Spanish Main Dr Unit 415, Cudjoe Key, FL 33042
- 2 Beds
- 2 Baths
- 754 Sq Ft
- Built 1989
701 Spanish Main Dr Unit 415, Cudjoe Key, FL 33042

Last Sold Summary
- 72 Days On Market

/46
$785,000

$10K PRICE DROP
- 2 Beds
- 1 Bath
- 864 Sq Ft
29034 Rose Dr, Big Pine Key, FL 33043

Experience the laid-back Florida Keys lifestyle in this beautifully updated, turn-key canal-front retreat, nestled in the quiet Eden Pines neighborhood among the roaming Key Deer. Situated on a 50-foot concrete seawall with step-down access, fish cleaning station, and a new boat lift, this property offers excellent boating access to both the ocean and bay. Inside, the open concept living area is

Ryan Gernaat

Coldwell Banker Schmitt Lower Keys (KW)

29034 Rose Dr, Big Pine Key, FL 33043
/47
$5,300 Per Month
- 2 Beds
- 2 Baths
- 1,311 Sq Ft
- Condo for Rent
1800 Atlantic Blvd, Key West, FL 33040

Isabella Braswell Key West Luxury Real Estate Inc (KW)

1800 Atlantic Blvd, Key West, FL 33040
/43
$2,595,000

Sold Aug 13, 2025

412 122nd Street Gulf, Marathon, FL 33050
- 3 Beds
- 2.5 Baths
- 2,391 Sq Ft
- Built 2008
Last Sold Summary
- 6% Below List Price
- $1,085/SF
- 100 Days On Market
Current Estimated Value $2,716,605

Last Listing Agent Natalie Ardis Coldwell Banker Schmitt Real Estate Co.

412 122nd Street Gulf, Marathon, FL 33050

/22
Not Listed For Sale

133 Freedom Ln, Big Pine Key, FL 33043
- 2 Beds
- 1.5 Baths
- 720 Sq Ft
- Built 1972
133 Freedom Ln, Big Pine Key, FL 33043

Last Sold Summary
- 49 Days On Market

/52
$599,000
- 3 Beds
- 2 Baths
- 960 Sq Ft
31118 Avenue I, Big Pine Key, FL 33043

Welcome to laid-back island living in this beautifully updated 3-bedroom, 2-bathroom home on Big Pine Key. Recent upgrades include a brand-new kitchen with stainless steel appliances, along with impact-resistant windows and doors throughout. The home also features a large downstairs enclosure offering abundant space for storage, tools, bicycles, kayaks, and other island essentials. Outside, the

Coby Taylor

Expert Realty LLC (HQ)

31118 Avenue I, Big Pine Key, FL 33043
/25
$3,995 Per Month
- 1 Bed
- 1 Bath
- 744 Sq Ft
- Condo for Rent
1215 97th Street Ocean Unit 11, Marathon, FL 33050

Stunning turnkey Atlantic Ocean waterfront condo with dockage, which can fit up to a 24 ft boat! Storm impact windows, sliding glass doors, new kitchen with stainless steel appliances. Quart's countertops, soft close drawers, glass backsplash, under counter lighting. All new bathroom cabinet, large anti-fog mirror cabinet, new tiled shower. All brand-new flooring, paint throughout with coastal

Natalia Boltz PA Power Net Realty.com Inc.

1215 97th Street Ocean Unit 11, Marathon, FL 33050
/69
$899,000

Sold Aug 15, 2025

2212 Fogarty Ave, Key West, FL 33040
- 4 Beds
- 3 Baths
- 1,826 Sq Ft
- Built 1954
Last Sold Summary
- $492/SF
- 5 Days On Market
Current Estimated Value $922,665

Last Listing Agent Bobby Baker Brightwild Real Estate

2212 Fogarty Ave, Key West, FL 33040

/26
Not Listed For Sale

6800 Maloney Ave Unit 103, Stock Island, FL 33040
- 2 Beds
- 2 Baths
- 748 Sq Ft
- Built 1987
6800 Maloney Ave Unit 103, Stock Island, FL 33040

Last Sold Summary
- 109 Days On Market

/85
$1,695,000
- 4 Beds
- 3 Baths
- 2,136 Sq Ft
30363 Flamingo Ln, Big Pine Key, FL 33043

Welcome to the ultimate angler's retreat in Tropical Bay Estates. This elevated concrete waterfront home offers quick access to both the Atlantic and Gulf, putting you in the heart of world-class fishing and diving. Located just a few miles from Bahia Honda State Park, you're ideally positioned for elite tarpon fishing, backcountry action, reef trips, and offshore runs. The dock is built for

Coby Taylor

Expert Realty LLC (HQ)

30363 Flamingo Ln, Big Pine Key, FL 33043
/32
$4,000 Per Month
- 2 Beds
- 2 Baths
- 1,056 Sq Ft
- Townhouse for Rent
138 N Indies Dr Unit B, Marathon, FL 33050

Waterfront Living in Duck Key!Enjoy the Florida Keys lifestyle from this charming 2-bedroom, 2-bath half duplex located on a quiet canal in the highly desirable community of Duck Key. Offering comfortable island living with beautiful waterfront views, this home is perfect for anyone looking to enjoy the relaxed Keys lifestyle.The open living and dining areas provide a bright, inviting

Nate Bartlett Berkshire Hathaway HomeServices Keys Real Estate

138 N Indies Dr Unit B, Marathon, FL 33050
/10
$749,000

Sold Mar 11, 2026

304 Amelia St, Key West, FL 33040
- 3 Beds
- 1 Bath
- 936 Sq Ft
- Built 1938
Last Sold Summary
- $800/SF
- 9 Days On Market
Current Estimated Value $858,517

Last Listing Agent Marilyn Wilbarger Berkshire Hathaway HomeServices Knight & Gardner Realty

304 Amelia St, Key West, FL 33040

/6
Est $337,885

Not Listed For Sale

101551 Overseas Hwy Unit 161, Key Largo, FL 33037
101551 Overseas Hwy Unit 161, Key Largo, FL 33037

Last Sold Summary
- 36 Days On Market

/13
$1,400,000
- 10 Beds
- 5 Baths
- 2,536 Sq Ft
206 12th Street Gulf, Marathon, FL 33050

THIS UNIQUE WATERFRONT PROPERTY HAS5 units on the property and all are long term rentals. There are 5 BUILDING RIGHTS that come with this property (please ask Listing Agents for details.

Lynn Goodwin

Coldwell Banker Schmitt Real Estate Co.

206 12th Street Gulf, Marathon, FL 33050
/32
$1,650 Per Month
- 1 Bath
- Apartment for Rent
103365 Overseas Hwy Unit A, Key Largo, FL 33037

End Unit A Newly Remodeled Studio Apartment featuring Brand New White Appliances. Conveniently located close to shopping, schools, restaurants, and more. Move -In Ready.

Tracey Petrusha LoKation

103365 Overseas Hwy Unit A, Key Largo, FL 33037
/56
$3,850,000

Sold Sep 23, 2025

66 S Andros Rd, Key Largo, FL 33037
- 5 Beds
- 4.5 Baths
- 3,800 Sq Ft
- Built 2018
Last Sold Summary
- 20% Below List Price
- $1,013/SF
- 227 Days On Market
Current Estimated Value $3,895,587

Last Listing Agent Katie Kennett Coastal Realty of the Florida Keys

66 S Andros Rd, Key Largo, FL 33037

/2
Not Listed For Sale

1800 Atlantic Blvd Unit 220C, Key West, FL 33040
- 2 Beds
- 2 Baths
- 1,424 Sq Ft
- Built 1984
1800 Atlantic Blvd Unit 220C, Key West, FL 33040

/43
$1,799,000
- 3 Beds
- 2.5 Baths
- 2,456 Sq Ft
51 Sawyer Dr, Cudjoe Key, FL 33042

Tucked into the sought-after waterfront enclave of Cudjoe Gardens, 51 Sawyer Drive offers the rarest of Florida Keys luxuries: ground-level living above base flood elevation. Built with integrity from solid concrete block and enhanced by Pella windows and a standing seam metal roof, this residence delivers peace of mind and timeless appeal. Boaters will appreciate the 80-foot concrete dock,

Lisa Ferringo

Coldwell Banker Schmitt Real Estate Co

51 Sawyer Dr, Cudjoe Key, FL 33042
/23
$4,000 Per Month
- 3 Beds
- 2 Baths
- 1,050 Sq Ft
- Townhouse for Rent
3314 Northside Dr Unit 55, Key West, FL 33040

Rent - $4,000/Month3BR/2BA Townhome in Solana Village, Key WestRent: $4,000 per monthLease: Long-term preferredPlease note: This townhouse is currently listed for sale. The future tenant must be willing to accommodate reasonable showing requests with advance notice. Every effort will be made to schedule showings at convenient times and to minimize any disruption.For additional

Yulia Vakhtenko Keys Top Realty LLC

3314 Northside Dr Unit 55, Key West, FL 33040
/20
$660,000

Sold Jul 22, 2026

1704 Duncan St, Key West, FL 33040
- 3 Beds
- 1 Bath
- 1,079 Sq Ft
- Built 1953
Last Sold Summary
- 6% Below List Price
- $612/SF
- 39 Days On Market
Current Estimated Value $749,953

Last Listing Agent Justyn Ewald Expert Realty LLC

1704 Duncan St, Key West, FL 33040

/14
Not Listed For Sale

1639 Pine Channel Dr, Little Torch Key, FL 33042
- 2 Beds
- 1 Bath
- 6,725 Sq Ft
- Built 1975
1639 Pine Channel Dr, Little Torch Key, FL 33042

Last Sold Summary
- 7 Days On Market

/47
$1,050,000

Open Fri 11AM - 1PM $50K PRICE DROP
- 3 Beds
- 2.5 Baths
- 1,750 Sq Ft
1133 W Ocean Dr Unit 13, Key Colony Beach, FL 33051

Reduced Quarterly Dues! Coastal Oceanfront 3 bedroom, 2 and a half Bathroom Condo in Key Colony Beach. Welcome to your slice of paradise at the southernmost point of Key Colony Beach! This spacious condo offers breathtaking views of the Atlantic and an unbeatable combination of peace and comfort, with investment potential. Step inside to an open-concept living space filled with natural light and

Michelle Vanhoose

Coldwell Banker Schmitt Real Estate Co.

1133 W Ocean Dr Unit 13, Key Colony Beach, FL 33051
/2
$2,600 Per Month
- 2 Beds
- 1 Bath
- 800 Sq Ft
- Apartment for Rent
710 Barcelona Rd Unit Bottom, Key Largo, FL 33037

WONDERFUL 2/1 ALL UTILITIES INCLUDED NO HOA IN KEY LARGO.

Roger Schaeffler Florida Realty of Miami Corp

710 Barcelona Rd Unit Bottom, Key Largo, FL 33037
/50
$4,250,000

Sold May 28, 2026

1320 Grinnell St, Key West, FL 33040
- 3 Beds
- 3.5 Baths
- 2,833 Sq Ft
- Built 2006
Last Sold Summary
- 1% Below List Price
- $1,500/SF
- 27 Days On Market
Current Estimated Value $4,233,985

Last Listing Agent Elizabeth Chamberlain Truman & Co. (KW)

1320 Grinnell St, Key West, FL 33040

/44
Not Listed For Sale

88540 Overseas Hwy Unit 104 and Boat Slip 46, Tavernier, FL 33070
- 2 Beds
- 2 Baths
- 853 Sq Ft
- Built 1985
88540 Overseas Hwy Unit 104 and Boat Slip 46, Tavernier, FL 33070

Last Sold Summary
- 58 Days On Market

Showing Results 481 - 520, Page 13 of 18

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