Monroe County, FL Homes

/23
$499,000 Pending
- 4 Beds
- 3 Baths
- 1,488 Sq Ft
41G Miriam St, Stock Island, FL 33040

Stock Island opportunity! This mobile home is a 4 bedroom 3 bathroom -it is divided into several lock out rooms that are currently rented If you are looking for housing for employees or good income potential call for more info. Cute front porch, 4 off street parking spaces, fenced yard, shared laundry. The structure has T1-11 siding and frame around the original mobile home in good condition.

Sandra Tuttle

Island Welcome Real Estate

(786) 889-4082

41G Miriam St, Stock Island, FL 33040
/19
$4,900 per month
- 2 Beds
- 2 Baths
- 884 Sq Ft
- House for Rent
27346 Martinique Ln, Summerland Key, FL 33042

Welcome to your private slice of paradise in the Florida Keys. This fully remodeled, exquisitely furnished 2-bedroom, 1-bathroom waterfront home is a true island escape. Where turquoise waters, swaying palms, and golden sunsets become your everyday view. Enjoy direct ocean access from your private dock, no bridges to slow you down. Lounge by the heated pool, dine under the stars, and feel the

Alicia Rufino Island Living Realty, LLC

27346 Martinique Ln, Summerland Key, FL 33042
/45
$630,000 Sold Dec 08, 2025

22970 Sharp Ln, Summerland Key, FL 33042
- 1 Bed
- 1 Bath
- 576 Sq Ft
- Built 1985
Last Sold Summary
- 10% Below List Price
- $1,094/SF
- 4 Days On Market
Last Listing Agent Nick Boumerhi Meyer and Boumerhi Realty LLC

22970 Sharp Ln, Summerland Key, FL 33042

/20
Est $687,742 Not Listed For Sale
- 2 Beds
- 3 Baths
- 1,131 Sq Ft
29132 Tulip Ln, Big Pine Key, FL 33043

29132 Tulip Ln, Big Pine Key, FL 33043

/47
$374,000
- 2 Beds
- 1 Bath
- 885 Sq Ft
55 Boca Chica Rd Unit 85, Key West, FL 33040

Updated and ready for you. This 2 Br/1 Bath unit is spacious and now looks like a million dollars! Fresh paint throughout, new floors in DR, Kitchen, bedrooms & bath, new plumbing and water heater, new bath vanity. The spacious Florida Room is the place to be, it invites you to relax, get comfortable and enjoy the day or evening. Check the Document Tab above and see much more information. Unit

Margarita Villoch

Island Group Realty (KW)

(305) 889-7849

55 Boca Chica Rd Unit 85, Key West, FL 33040
/20
$5,250 per month
- 3 Beds
- 3 Baths
- 1,945 Sq Ft
- Townhouse for Rent
96 Ave C, Marathon, FL 33050

Property Id: 1257805This is a long-term rental 12 months or longer. Furnishing optional.Beautiful fully-furnished (furnishing optional) townhome in Bonefish Yacht Club next to Bonefish Marina. The home overlooks the marina, this 3-story townhome, end unit has been thoughtfully updated and curated for a tranquil living experience with all the comforts of home. 3 bedrooms

96 Ave C, Marathon, FL 33050
/55
$3,210,000 Sold Jun 18, 2025

128 W Plaza Del Sol, Islamorada, FL 33036
- 6 Beds
- 3.5 Baths
- 2,843 Sq Ft
- Built 1986
Last Sold Summary
- 7% Below List Price
- $1,129/SF
- 61 Days On Market
Current Estimated Value $3,320,187

Last Listing Agent Jessica Pinder

128 W Plaza Del Sol, Islamorada, FL 33036

/72
Est $709,354 Not Listed For Sale
- 2 Beds
- 2 Baths
- 836 Sq Ft
29 Spoonbill Way, Key West, FL 33040

29 Spoonbill Way, Key West, FL 33040

/44
$1,495,000
- 3 Beds
- 3 Baths
- 1,284 Sq Ft
1211 Knowles Ln, Key West, FL 33040

Discover the timeless charm of this beautifully remodeled historic home located in Old Town, Key West. This fully furnished 3 bedroom, 2.5 bath property boasts lovingly restored Dade County Pine, and combines classic craftsmanship with modern comforts. 1211 Knowles Ln features a 300 sq.ft. loft currently used as a 3rd bedroom, office and storage ! Both front and side porches invite you to relax

Emily Lombard

Ocean Sotheby's International Realty

(786) 788-0660

1211 Knowles Ln, Key West, FL 33040
/43
$3,500 per month
- 3 Beds
- 2 Baths
- 1,372 Sq Ft
- House for Rent
67 Jewfish Ave, Key Largo, FL 33037

BRING YOUR BOATS AND YOUR MOTORIZED TOYS! NO MANDATORY HOA! REMODELED SINGLE-FAMILY HOME FOR RENT ON DESIRABLE JEWFISH AVE, LOCATED OCEANSIDE JUST ONE BLOCK FROM THE OCEAN AND ENJOY THE HIGHLY SOUGHT AFTER ACCESS TO LARGO SOUND HOMEOWNERS PARK WHICH IS OPEN TO RENTERS WITH ONLY A $250.00 ANNUAL MEMBERSHIP FEE. THIS HOMEOWNERS PARK HAS A BOAT LAUNCH AND PRIVATE BEACH FOR MEMBERS ONLY. TURNKEY

Anthony Garcia The Keyes Company

67 Jewfish Ave, Key Largo, FL 33037
/35
$1,499,900 Sold May 27, 2025

1082 Bay Dr, Summerland Key, FL 33042
- 4 Beds
- 2.5 Baths
- 1,440 Sq Ft
- Built 1980
Last Sold Summary
- 25% Below List Price
- $1,042/SF
- 602 Days On Market
Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

1082 Bay Dr, Summerland Key, FL 33042

/29
Est $1,607,996 Not Listed For Sale
- 3 Beds
- 3 Baths
- 1,040 Sq Ft
624 Catholic Ln, Key West, FL 33040

624 Catholic Ln, Key West, FL 33040

/33
$399,900 Under Contract
- 1 Bed
- 1.5 Baths
- 827 Sq Ft
79901 Overseas Hwy Unit 218, Islamorada, FL 33036

LET'S MAKE A DEAL! Seller has just reduced this condo by $50,000. At this price, this updated 1BR/1.5BA condo is the largest one bedroom condo available for sale in the Upper Keys. Located at The Palms of Islamorada, Mile Marker 79.9, this is one of the area's premier ocean front complexes. Jump on this opportunity now. Grab this unit before someone else does. The Palms of Islamorada oceanfront

Andrea (Andi) Saylor

Paradise Florida Keys Real Estate, a Luxury Brand

(786) 938-6229

79901 Overseas Hwy Unit 218, Islamorada, FL 33036
/9
$3,000 per month
- 3 Beds
- 2 Baths
- 1,000 Sq Ft
- House for Rent
30965 Mercedes Rd, Big Pine Key, FL 33043

Property Id: 15316113 br/ 2 ba house in the Avenues area of Big Pine Key. GREAT neighborhood. Updated kitchen and baths. Freshly painted. Vinyl plank and ceramic flooring throughout. Large yard (5000 sf) has enough room for cars and boat. New central air system works great. It is not a mobile home. It is a well built modular home Please have verifiable employment history,

30965 Mercedes Rd, Big Pine Key, FL 33043
/3
$765,000 Sold Mar 10, 2025

3366 Pearl Ave, Key West, FL 33040
- 2 Beds
- 2 Baths
- 1,305 Sq Ft
- Built 1980
Last Sold Summary
- 3% Below List Price
- $586/SF
- 65 Days On Market
Current Estimated Value $775,432

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

3366 Pearl Ave, Key West, FL 33040

/28
Est $3,658,621 Not Listed For Sale
- 4 Beds
- 4 Baths
- 1,828 Sq Ft
522 Olivia St, Key West, FL 33040

522 Olivia St, Key West, FL 33040

/50
$2,750,000
- 6 Beds
- 4 Baths
- 3,248 Sq Ft
581 10th St, Key Colony Beach, FL 33051

Fantastic 6 Bedroom, 4 Bath 3,248 sq. ft. waterfront pool home in Key Colony Beach, an upscale coastal community of waterfront homes that allows weekly rentals and offers a plethora of amenities including gorgeous beaches, a beach club, golf, tennis, pickleball, restaurants, parks, shopping and more! World-class fishing and diving are just minutes from your 75' concrete dock on a 100' wide

Lisa Ferringo

Coldwell Banker Schmitt Lower Keys (KW)

(786) 661-3798

581 10th St, Key Colony Beach, FL 33051
/16
$5,500 per month
- 2 Beds
- 2 Baths
- 1,016 Sq Ft
- House for Rent
87455 Old Hwy 229 Hwy Unit 87455, Plantation Key, FL 33036

Beautifully maintained 2-bedroom, 2-bath townhouse-style condo located oceanside in the heart of Islamorada. This fully turn-key residence offers effortless island living—just arrive and enjoy. Featuring a newer A/C system (2022), updated appliances (2024), and fully replaced air ducts (2024) for optimal comfort and efficiency. Impact windows provide peace of mind, while electric blackout blinds

Jose Medina Main Assets Corp

87455 Old Hwy 229 Hwy Unit 87455, Plantation Key, FL 33036
/60
$1,850,000 Sold Oct 27, 2025

1015 Adams Dr, Key Largo, FL 33037
- 3 Beds
- 2.5 Baths
- 2,380 Sq Ft
- Built 1999
Last Sold Summary
- 16% Below List Price
- $777/SF
- 156 Days On Market
Current Estimated Value $1,839,062

Last Listing Agent Brooke Vega American Caribbean Real Estate, Christie's International Real Estate

1015 Adams Dr, Key Largo, FL 33037

/19
Est $714,422 Not Listed For Sale
- 2 Beds
- 1 Bath
- 648 Sq Ft
905 Pohalski St, Key West, FL 33040

905 Pohalski St, Key West, FL 33040

/10
$499,000
- Land
63 Sugarloaf Dr, Sugarloaf Shores, FL 33042

Welcome to the lowest priced waterfront lot with an active building permit on prestigious Sugarloaf Key. This oversized 14,706 sq. ft. canal-front property features no-bridge ocean access, granting you instant entry to world-class fishing, diving, and boating. Located in the premier residential enclave of the Sugarloaf Shores, this lot includes an active building permit for a custom 2,120 sq.

Lisa Ferringo

Coldwell Banker Schmitt Lower Keys (KW)

(305) 834-4054

63 Sugarloaf Dr, Sugarloaf Shores, FL 33042
/20
$9,487 per month
- 4 Beds
- 3.5 Baths
- 1,797 Sq Ft
- Condo for Rent
1315 Whitehead St Unit ID1297834P, Key West, FL 33040

Southernmost View is a modern and luxurious waterfront home located in a private seven-home gated community, just steps from the beach and the Southernmost Point of the continental USA. Enjoy turquoise blue waters from the rooftop sundeck, perfect for tanning, reading, and sipping your morning coffee. Relax under the southernmost stars or watch the sunset over the horizon.This upscale beach

1315 Whitehead St Unit ID1297834P, Key West, FL 33040
/35
$295,000 Sold Jul 02, 2025

439 83rd Street Ocean, Marathon, FL 33050
- 2 Beds
- 2 Baths
- 1,018 Sq Ft
- Built 1961
Last Sold Summary
- 1% Below List Price
- $290/SF
- 20 Days On Market
Last Listing Agent Mallory Pinto Keys Ocean Realty Inc.

439 83rd Street Ocean, Marathon, FL 33050

/33
Est $1,159,679 Not Listed For Sale
- 2 Beds
- 2.5 Baths
- 1,147 Sq Ft
96000 Overseas Hwy Unit H4, Key Largo, FL 33037

96000 Overseas Hwy Unit H4, Key Largo, FL 33037

/42
$655,000
- 2 Beds
- 2 Baths
- 841 Sq Ft
500 Burton Dr Unit 4203, Tavernier, FL 33070

TWO oceanfront balconies comes with this 2/2 Condo with an Oceanfront Cafe & Pool bar !! Marina has direct ocean access and is naturally protected from the elements. Jr. Olympic pool with a 14 person Spa. Lighted Tennis & pickle ball courts. This Condo is being sold fully furnished. Impact windows and sliders !!

Tom Rodriguez

American Caribbean Real Estate, Christie's International Real Estate

(866) 689-4307

500 Burton Dr Unit 4203, Tavernier, FL 33070
/8
$4,800 per month
- 3 Beds
- 1 Bath
- 800 Sq Ft
- Property for Rent
927 Catherine St, Key West, FL 33040

Furnished 2-bedroom plus loft area with one-bath Conch house in the heart of Old Town Key West. Classic island charm with a functional floor plan and bright living spaces. All utilities and internet included for easy, turnkey living. Prime location close to dining, shopping, and entertainment. Available March 1st.

Jessica Celli Berkshire Hathaway HomeServices Knight & Gardner Realty

927 Catherine St, Key West, FL 33040
/44
$1,125,000 Sold Jan 16, 2026

283 Golf Club Dr, Key West, FL 33040
- 3 Beds
- 3 Baths
- 1,600 Sq Ft
- Built 1999
Last Sold Summary
- 13% Below List Price
- $703/SF
- 37 Days On Market
Last Listing Agent Dan Serban Key West Luxury Real Estate Inc (KW)

283 Golf Club Dr, Key West, FL 33040

/33
Est $2,559,800 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,016 Sq Ft
17279 Pinetree Ln, Summerland Key, FL 33042

17279 Pinetree Ln, Summerland Key, FL 33042

/50
$2,400,000
- 3 Beds
- 2.5 Baths
- 3,172 Sq Ft
317 E Seaview Dr, Duck Key, FL 33050

ACROSS THE STREET FROM THE ATLANTIC OCEAN! Rare opportunity to own a prime cleared residential lot (~7,500 sq ft) on the quiet, ocean-side of Duck Key's exclusive Yacht Club Island--the perfect canvas for your Florida Keys dream home! Build stilted for breathtaking potential ocean views, with easy permitting still available in this sought-after community. Enjoy secure, patrolled security and a

Joseph Suarez

Trustpoint Realty, LLC

(786) 414-1029

317 E Seaview Dr, Duck Key, FL 33050
/2
$7,000 per month
- 4 Beds
- 2 Baths
- 1,900 Sq Ft
- House for Rent
1330 3rd St, Key West, FL 33040

Property Id: 2292938Move-in ready Key West living! Close to shopping, schools, beaches and Old Town.Property Highlights•Spacious 4 bedrooms / 2 bathrooms•~1,900 sq ft•Fenced yard with covered porch•Pet-friendly with deposit•Annual lease - $7,000 per month•Utilities not included•Credit/Background Check This home combines comfort, space, and

1330 3rd St, Key West, FL 33040
/31
$585,000 Sold Feb 13, 2025

410 Coconut Dr, Key Largo, FL 33037
- 2 Beds
- 2 Baths
- 912 Sq Ft
- Built 1991
Last Sold Summary
- 15% Below List Price
- $641/SF
- 187 Days On Market
Current Estimated Value $623,404

Last Listing Agent Martha Carter Engel & Volkers Islamorada

410 Coconut Dr, Key Largo, FL 33037

/38
Est $780,056 Not Listed For Sale
- 2 Beds
- 1.5 Baths
- 816 Sq Ft
29154 Cedar Dr, Big Pine Key, FL 33043

29154 Cedar Dr, Big Pine Key, FL 33043

/37
$1,066,000
- 2 Beds
- 1 Bath
- 749 Sq Ft
1116 Eaton St, Key West, FL 33040

Charming Key West Cottage with Pool, Rooftop Deck & Prime Old Town Location.Discover the ultimate island lifestyle in this lovely Key West cottage located in the vibrant heart of Old Town. Perfectly sized for effortless living, this beautifully maintained home offers all the charm, comfort, and convenience you could dream of--without the hassle of high-maintenance upkeep.From the moment you

Margarita Villoch

Island Group Realty (KW)

(786) 550-6363

1116 Eaton St, Key West, FL 33040
/23
$5,000 per month
- 3 Beds
- 2 Baths
- 1,320 Sq Ft
- Property for Rent
28 Whistling Duck Ln, Key West, FL 33040

Bright and spacious 3-bedroom, 2-bathroom home perfectly situated in the Key West Golf Club community. Overlooking the 9th hole, this property offers a peaceful setting in one of the most desirable parts of the neighborhood, with plenty of parking available.The home is offered unfurnished, with no utilities included, giving you the flexibility to make it your own. One bedroom is downstairs with

Everett Watkins Keller Williams Key West Compass Realty

28 Whistling Duck Ln, Key West, FL 33040
/44
$1,675,000 Sold Jul 30, 2025

2605 Gulfview Dr, Key West, FL 33040
- 3 Beds
- 3 Baths
- 1,320 Sq Ft
- Built 1999
Last Sold Summary
- 7% Below List Price
- $1,269/SF
- 116 Days On Market
Current Estimated Value $1,704,758

Last Listing Agent Paige Bethel Island Home Realty Inc.

2605 Gulfview Dr, Key West, FL 33040

/44
Est $489,398 Not Listed For Sale
- 1 Bed
- 2 Baths
- 792 Sq Ft
2000 Coco Plum Dr Unit 1202, Marathon, FL 33050

2000 Coco Plum Dr Unit 1202, Marathon, FL 33050

/49
$1,790,000
- 3 Beds
- 3 Baths
- 2,034 Sq Ft
159 Iroquois Dr, Islamorada, FL 33036

Discover island living at its finest in this beautifully remodeled 3-bedroom, 3-bath ''Florida Modern'' CBS home, ideally located in the desirable Lower Matecumbe Beach neighborhood of Islamorada.A light-filled open-concept layout seamlessly connects the living, dining, and kitchen areas--perfect for entertaining or relaxed island living. The home features three spacious bedrooms and three full

Pierre Bellion

Ocean Sotheby's International Realty

(645) 600-8447

159 Iroquois Dr, Islamorada, FL 33036
/20
$13,487 per month
- 3 Beds
- 2 Baths
- 1,399 Sq Ft
- Condo for Rent
2026 Seidenberg Ave Unit ID1297830P, Key West, FL 33040

Welcome to Hidden Oasis, a luxurious three-bedroom, two-bathroom home nestled in the heart of Midtown, Key West. This stunning property offers contemporary luxury with an open floor plan, situated on a private fenced-in yard on a corner lot with lush tropical landscaping. Feel at home as you step through French doors to the backyard, featuring a private heated pool, lounge seating, a TV, a grill,

2026 Seidenberg Ave Unit ID1297830P, Key West, FL 33040
/60
$930,000 Sold Jan 23, 2026

27405 Guadaloupe Ln, Summerland Key, FL 33042
- 3 Beds
- 2 Baths
- 1,288 Sq Ft
- Built 2008
Last Sold Summary
- 2% Below List Price
- $722/SF
- 51 Days On Market
Last Listing Agent Mark Gable Engel & Volkers Marathon

27405 Guadaloupe Ln, Summerland Key, FL 33042

/54
Est $6,349,846 Not Listed For Sale
- 4 Beds
- 4.5 Baths
- 3,907 Sq Ft
257 Tollgate Blvd, Islamorada, FL 33036

257 Tollgate Blvd, Islamorada, FL 33036

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