Monroe County, FL Homes

/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

814 Ashe St, Key West, FL 33040
/34
$5,000 Per Month
- 3 Beds
- 3 Baths
- 1,380 Sq Ft
- House for Rent
37 Palm Dr, Key West, FL 33040

Turnkey Waterfront Living in Saddlebunch Key - $5,500/monthThis fully furnished 3 bed, 3 bath canal-front home offers the ultimate Keys lifestyle just behind Baby's Coffee. Enjoy quick access to open water with your own boat lift, perfect for fishing or sunset cruising. Spacious open-concept living, updated kitchen, and outdoor entertaining areas make this a perfect getaway or full-time

Dan Serban

Key West Luxury Real Estate Inc (KW)

37 Palm Dr, Key West, FL 33040
/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 $900,212

Last Listing Agent Gregory Sullivan BYOWNER.COM

185 Gardenia St, Tavernier, FL 33070

/48
Est $1,603,151

Not Listed For Sale

820 Carsten Ln, Key West, FL 33040
- 2 Beds
- 2 Baths
- 860 Sq Ft
- Built 1908
820 Carsten Ln, Key West, FL 33040

Last Sold Summary
- 102 Days On Market
Last Listing Agent Dina Schoneck Berkshire Hathaway HomeServices Knight & Gardner Realty

/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 Real Estate Co

17013 Coral Dr, Sugarloaf Key, FL 33042
/18
Starting at $3,200 Per Month
- 2 Beds
5555 College Rd, Key West, FL 33040

Sunset Marina Apts

5555 College Rd, Key West, FL 33040
/53
$715,000

Sold Jun 22, 2026

40 Transylvania Ave, Key Largo, FL 33037
- 3 Beds
- 2 Baths
- 1,260 Sq Ft
- Built 1978
Last Sold Summary
- $567/SF
- 4 Days On Market
Current Estimated Value $722,404

Last Listing Agent BJ Born Real Estate Sales Force, Inc.

40 Transylvania Ave, Key Largo, FL 33037

/35
Est $1,311,725

Not Listed For Sale

231 Southard St, Key West, FL 33040
- 2 Beds
- 2.5 Baths
- 960 Sq Ft
- Built 1993
231 Southard St, Key West, FL 33040

Last Sold Summary
- 93 Days On Market
Last Listing Agent Mary Readel Florida Keys Real Estate Co. (KW)

/43
$875,000

$124K PRICE DROP
- 3 Beds
- 2 Baths
- 1,036 Sq Ft
420 W Indies Dr, Ramrod Key, FL 33042

Beautifully renovated canal-front home on an oversized corner lot in the heart of Breezeswept Beach Estates on Ramrod Key, ideally located on one of only two flow-through canals in the neighborhood. This exceptional property offers a rare combination of quality construction, thoughtful upgrades, and excellent boating access The owners spared no expense in the renovation, which includes a

Lisa Ferringo

Coldwell Banker Schmitt Real Estate Co

420 W Indies Dr, Ramrod Key, FL 33042
/30
$5,300 Per Month
- 3 Beds
- 2 Baths
- 1,440 Sq Ft
- House for Rent
932 Tropical Ln, Key Largo, FL 33037

Furnished seasonal rental, available October through March. Perched at the tip of its own peninsula in Key Largo's Cross Key Waterways, this 3-bed, 2-bath, 1,440 sq ft canal-front retreat is surrounded by water on nearly every side. Boats dock steps from the door, and even the kitchen sink looks out over palm trees and passing boats — do the dishes with a view you won't want to look away from. A

Ashley Kettner

Compass Florida LLC

932 Tropical Ln, 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 $4,293,928

Last Listing Agent Brenda Torrella Berkshire Hathaway HomeServices Keys Real Estate

78 Tingler Ln, Marathon, FL 33050

/34
Est $794,516

Not Listed For Sale

558 E Shore Dr, Summerland Key, FL 33042
- 2 Beds
- 2 Baths
- 1,392 Sq Ft
- Built 1994
558 E Shore Dr, Summerland Key, FL 33042

Last Sold Summary
- 22 Days On Market
Last Listing Agent Tommy Gomez Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key

/66
$2,099,000
- 4 Beds
- 3.5 Baths
- 2,548 Sq Ft
1106 Thatch Ln, Cudjoe Key, FL 33042

Set along a peaceful canal on Cudjoe Key, this 2016 residence pairs solid CBS construction with an unmistakably elevated sense of island living. This 4 bedroom, 3.5 bath home features impact windows and doors and a standing seam metal roof, speaking to a level of craftsmanship built to endure, while 2,548 square feet of living space and roughly 1,370 square feet of balconies invite the

Lisa Ferringo

Coldwell Banker Schmitt Real Estate Co

1106 Thatch Ln, Cudjoe Key, FL 33042
/20
Starting at $2,275 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

106003 Overseas Hwy, Key Largo, FL 33037
/18
$1,550,000

Sold Jul 14, 2026

56185 Overseas Hwy, Marathon, FL 33050
- Land
- 10 Acres
- $155,000 per Acre
Last Sold Summary
- 69% Below List Price
- 239 Days On Market
Current Estimated Value $2,391,111

Last Listing Agent Sam Williams Coldwell Banker Schmitt Real Estate Co.

56185 Overseas Hwy, Marathon, FL 33050

/40
Est $1,145,533

Not Listed For Sale

28552 Maracaibo Rd, Summerland Key, FL 33042
- 2 Beds
- 2 Baths
- 988 Sq Ft
- Built 1989
28552 Maracaibo Rd, Summerland Key, FL 33042

Last Sold Summary
- 8 Days On Market
Last Listing Agent Teri Hiller Coldwell Banker Schmitt Real Estate Co.

/61
$1,399,000

$50K PRICE DROP
- 2 Beds
- 2 Baths
- 1,372 Sq Ft
21012 6th Ave, Cudjoe Key, FL 33042

Island living becomes effortless at this beautifully maintained waterfront retreat in the heart of Cudjoe Gardens. Located on a deep-water canal with quick ocean access, this CBS pool home offers the rare combination of ground-level convenience while above the flood plain. From the moment you arrive the property feels inviting and relaxed. Tropical landscaping and manicured grounds create a

Lisa Ferringo

Coldwell Banker Schmitt Real Estate Co

21012 6th Ave, Cudjoe Key, FL 33042
/39
$5,000 Per Month
- 3 Beds
- 2 Baths
- 1,598 Sq Ft
- House for Rent
9 Blue Water Dr, Key West, FL 33040

Spacious 3 bedroom and 2 bathroom home for long term rental. High and dry Single family residence with extraordinary water views. This lot has ample off street parking, storage, a workshop, enclosed garage, Laundry room, and flex spaces. There is a large air conditioned shed in the back yard, perfect for an office or art studio.Landscaping and garbage service included.Applicants are

Dustan Carpenter

Berkshire Hathaway HomeServices Knight & Gardner Realty

9 Blue Water Dr, Key West, FL 33040
/45
$2,900,000

Sold Jan 09, 2026

1224 Florida St, Key West, FL 33040
- 5 Beds
- 5.5 Baths
- 2,760 Sq Ft
- Built 2006
Last Sold Summary
- 9% Below List Price
- $1,051/SF
- 56 Days On Market
Current Estimated Value $2,926,199

Last Listing Agent Brenda Donnelly Brenda Donnelly Real Estate LLC

1224 Florida St, Key West, FL 33040

/21
Est $1,031,815

Not Listed For Sale

419 Blackbeard Rd, Summerland Key, FL 33042
- 2 Beds
- 2 Baths
- 1,050 Sq Ft
- Built 1988
419 Blackbeard Rd, Summerland Key, FL 33042

Last Sold Summary
- 250 Days On Market
Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.

/44
$59,900

$9K PRICE DROP
- 2 Beds
- 2 Baths
- 1,120 Sq Ft
617 Front St Unit C54 Penthaus Wk36, Key West, FL 33040

Experience premium waterfront ownership with this deeded timeshare week 36 in the highly coveted Building C at the Galleon Resort. This PENTHOUSE, end-corner unit offers one of the most desirable locations in the resort, featuring unobstructed, straight-on views of the Gulf of Mexico. The residence boasts soaring vaulted ceilings, additional windows for abundant natural light, and multiple

Stephanie Herrmann

Truman & Co. Real Estate

617 Front St Unit C54 Penthaus Wk36, Key West, FL 33040
/20
Starting at $3,110 Per Month
- 2 - 3 Beds
6973 Overseas Hwy, Marathon, FL 33050

Call Today to Book Your Appointment, we are eager to connect with you in Person!Tarpon Harbour is located in Monroe County, the 33050 ZIP Code, and the Monroe attendance zone.

Tarpon Harbour

6973 Overseas Hwy, Marathon, FL 33050
/41
$1,065,000

Sold Jun 26, 2026

325 Pirates Rd, Summerland Key, FL 33042
- 3 Beds
- 2 Baths
- 1,320 Sq Ft
- Built 2025
Last Sold Summary
- 9% Below List Price
- $807/SF
- 148 Days On Market
Current Estimated Value $1,075,879

Last Listing Agent Nick Boumerhi Meyer and Boumerhi Realty LLC

325 Pirates Rd, Summerland Key, FL 33042

/47
Not Listed For Sale

27853 Coral Shores Rd, Little Torch Key, FL 33042
- 2 Beds
- 2 Baths
- 960 Sq Ft
- Built 1979
27853 Coral Shores Rd, Little Torch Key, FL 33042

Last Sold Summary
- 117 Days On Market
Last Listing Agent Leah Scarborough Island Welcome Real Estate

/87
$2,199,000

Under Contract
- 4 Beds
- 4 Baths
- 2,043 Sq Ft
52 Key Haven Rd, Key West, FL 33040

Getting out on the water is simple from this beautifully remodeled 4-bedroom, 4-bath home, and coming home feels just as inviting. Set along a wide canal, the property offers quick access to open water with no fixed bridges. A private pool and inviting indoor-outdoor living spaces make being at home just as enjoyable as a day on the water. Inside, the open layout feels bright, spacious, and

Lisa Ferringo

Coldwell Banker Schmitt Real Estate Co

52 Key Haven Rd, Key West, FL 33040
/37
$6,000 Per Month
- 3 Beds
- 4 Baths
- 2,012 Sq Ft
- House for Rent
129 N Indies Dr, Duck Key, FL 33050

Brand new construction for rent in the heart of Duck Key, FL, between Marathon and Islamorada. This newly built, single story 3 bedroom, 4 bathroom home features a split floor plan and a dedicated pool bathroom, with 10.8 foot ceilings, 8 foot solid doors, impact rated windows and doors, a one car garage, and a gourmet kitchen with marble countertops and premium finishes, plus a heated saltwater

Joseph Suarez

Trustpoint Realty, LLC

129 N Indies Dr, Duck Key, FL 33050
/40
$522,500

Sold Oct 10, 2025

1115 Sombrero Blvd Unit 101A, Marathon, FL 33050
- 2 Beds
- 2 Baths
- 1,096 Sq Ft
- Built 1975
Last Sold Summary
- 5% Below List Price
- $477/SF
- 228 Days On Market
Current Estimated Value $526,743

Last Listing Agent Ally Kelley Ocean Sotheby's International

1115 Sombrero Blvd Unit 101A, Marathon, FL 33050

/43
Est $1,292,268

Not Listed For Sale

630 10th St, Key Colony Beach, FL 33051
- 3 Beds
- 2 Baths
- 1,581 Sq Ft
- Built 2001
630 10th St, Key Colony Beach, FL 33051

Last Sold Summary
- 115 Days On Market
Last Listing Agent Teri Hiller Coldwell Banker Schmitt Real Estate Co.

/40
$1,249,000

$50K PRICE DROP
- 2 Beds
- 2.5 Baths
- 1,320 Sq Ft
96000 Overseas Hwy Unit P1, Key Largo, FL 33037

This is the only end-unit town home located on the island area of the prestigious Buttonwood Bay Club. This fully furnished, beautifully updated home has granite countertops, high-end finishes, an open-concept living and dining area, and impact glass doors that lead out to your patio where you can grill, entertain or simply relax. This end unit has extra light a bonus side patio and is located

Karol Marsden

Freewheeler Realty, Inc.

96000 Overseas Hwy Unit P1, Key Largo, FL 33037
/20
Starting at $3,145 Per Month
- 1 - 3 Beds
750 Fort St, Key West, FL 33040

Discover your place in the heart of Key West's most historic and vibrant neighborhood. The Lofts at Bahama Village offers affordable housing options designed for locals, where homeownership and rental opportunities meet the warmth of a close-knit community.Live steps away from iconic Key West landmarks, while enjoying the charm and cultural heritage that make Bahama Village truly one of a

Lofts at Bahama Village

750 Fort St, Key West, FL 33040
/50
$1,632,000

Sold Apr 30, 2026

29678 Constitution Ave, Big Pine Key, FL 33043
- 3 Beds
- 2.5 Baths
- 2,172 Sq Ft
- Built 1972
Last Sold Summary
- 5% Below List Price
- $751/SF
- 62 Days On Market
Current Estimated Value $1,644,840

Last Listing Agent Callie Harris Brenda Donnelly Real Estate LLC

29678 Constitution Ave, Big Pine Key, FL 33043

/2
Not Listed For Sale

115 Long Key Rd, Key Largo, FL 33037
- 2 Beds
- 2 Baths
- 1,360 Sq Ft
- Built 1999
115 Long Key Rd, Key Largo, FL 33037

Last Sold Summary
- 7 Days On Market
Last Listing Agent Sari Shapiro Douglas Elliman

/20
$319,900

$19K PRICE DROP
- 2 Beds
- 1.5 Baths
- 1,024 Sq Ft
300 Ocean Dr Unit 22, Key Largo, FL 33037

Discover Key Largo's Hidden Gem - Holiday By the Sea! This solid concrete fortress, nestled in an X-Flood Zone, has been beautifully upgraded with new electrical, air conditioning/heating, hot water tank, doors, flooring, blinds, and fresh paint.Enjoy harbor views from two of your three private balconies and take advantage of this prime location just steps from Key Largo Harbor Marina.

Philip Kravitz

Coldwell Banker Schmitt Key Largo

300 Ocean Dr Unit 22, Key Largo, FL 33037
/20
Starting at $2,349 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

21 1st Ave, Key Largo, FL 33037
/103
$4,775,000

Sold Jul 28, 2026

230 15th Cir, Key Colony Beach, FL 33051
- 5 Beds
- 4 Baths
- 3,580 Sq Ft
- Built 2025
Last Sold Summary
- 20% Below List Price
- $1,334/SF
- 203 Days On Market
Current Estimated Value $4,079,819

Last Listing Agent Joseph Suarez Trustpoint Realty, LLC

230 15th Cir, Key Colony Beach, FL 33051

/57
Est $5,682,636

Not Listed For Sale

124 Sunrise Dr, Marathon, FL 33050
- 5 Beds
- 5.5 Baths
- 5,200 Sq Ft
- Built 2010
124 Sunrise Dr, Marathon, FL 33050

Last Sold Summary
- 53 Days On Market
Last Listing Agent Tara Graham The Keyes Company

/66
$26,000

$5K PRICE DROP
- 2 Beds
- 2 Baths
- 1,120 Sq Ft
617 Front St Unit D-54 Week 37 Penthou, Key West, FL 33040

Penthouse, top floor, end unit! Experience premium waterfront ownership with this deeded timeshare in the highly coveted building at the Galleon Resort. This unit delivers a truly unforgettable Key West sunset experience, among the finest views in Key West. The residence boasts windows for abundant natural light and a balcony that maximizes the breathtaking waterfront setting. Enjoy front-row

Stephanie Herrmann

Truman & Co. (KW)

617 Front St Unit D-54 Week 37 Penthou, Key West, FL 33040
/20
$3,356

Total Monthly Price
- 4 Beds
- 2 Baths
- 1,377 Sq Ft
- Condo for Rent
210 W 2nd Ct Unit SI FL2-ID1546489P, Key Largo, FL 33037

The advertised rate of $3,357/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 17, 2026. Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can

210 W 2nd Ct Unit SI FL2-ID1546489P, Key Largo, FL 33037
/3
$650,000

Sold Dec 04, 2025

806 Pearl St, Key West, FL 33040
- 4 Beds
- 3 Baths
- 1,504 Sq Ft
- Built 1933
Last Sold Summary
- $432/SF
- 0 Days On Market
Current Estimated Value $769,154

Last Listing Agent Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

806 Pearl St, Key West, FL 33040

/40
Est $2,017,225

Not Listed For Sale

106 Tequesta St, Tavernier, FL 33070
- 4 Beds
- 4 Baths
- 2,800 Sq Ft
- Built 2022
106 Tequesta St, Tavernier, FL 33070

Last Sold Summary
- 160 Days On Market
Last Listing Agent Elsy Gonzalez Golden International Realty Corp

Showing Results 41 - 80, Page 2 of 18

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