Monroe County, FL Homes

/53
$629,000 Under Contract
- 2 Beds
- 2 Baths
- 1,336 Sq Ft
29073 Iris Dr, Big Pine Key, FL 33043

Updated and well-maintained, this charming A-frame home offers a surprising amount of space inside with 1336 sq. ft. of living area. Situated on a 50 ft. wide canal, the property features 50 ft. of canal frontage, a concrete seawall, recent 10,000 lb. boat lift, a jet ski launch, and steps down to the canal making it easy to get into a kayak. The 2-story living area is light and bright with an

Patti Nickless

Coldwell Banker Schmitt Lower Keys (KW)

(855) 799-6756

29073 Iris Dr, Big Pine Key, FL 33043
/15
$1,650 per month
- 1 Bath
- 450 Sq Ft
- 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 Venture Realty Group

103365 Overseas Hwy Unit A, Key Largo, FL 33037
/38
$530,000 Sold Apr 25, 2025

21 Orange Dr, Key Largo, FL 33037
- 4 Beds
- 2 Baths
- 1,398 Sq Ft
- Built 1987
Last Sold Summary
- 28% Below List Price
- $379/SF
- 379 Days On Market
Current Estimated Value $562,908

Last Listing Agent April Struhs Coldwell Banker Schmitt Key Largo

21 Orange Dr, Key Largo, FL 33037

/12
Est $273,469 Not Listed For Sale

96 Madeira Rd Unit 26, Islamorada, FL 33036
- 1 Bed
- 45 Sq Ft
- Built 2014
96 Madeira Rd Unit 26, Islamorada, FL 33036

Last Sold Summary
- 1% Above List Price
- $6,000/SF
- 21 Days On Market
Last Sold Price $270,000

Last Listing Agent The Jude Lindback Te Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

/34
$799,000
- 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
/24
$3,200 per month
- 3 Beds
- 2 Baths
- 1,248 Sq Ft
- House for Rent
61 Central Ave, Key Largo, FL 33037

Beautiful stilt home for rent in the heart of Key Largo, located in the highly sought-after Bay Haven community at Mile Marker 99.5. This private and serene property offers 3 bedrooms and 2 bathrooms upstairs, surrounded by mature landscaping and tranquil natural views. A private outdoor shower off the primary bedroom and multiple balconies create the perfect setting to enjoy the Keys lifestyle.

Rodolfo Sardina Seaside Realty, LLC

61 Central Ave, Key Largo, FL 33037
/46
$1,390,000 Sold Aug 26, 2025

229 Caribbean Dr E, Summerland Key, FL 33042
- 3 Beds
- 2 Baths
- 1,152 Sq Ft
- Built 1985
Last Sold Summary
- 1% Below List Price
- $1,207/SF
- 30 Days On Market
Current Estimated Value $1,387,796

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

229 Caribbean Dr E, Summerland Key, FL 33042

/46
Est $813,731 Not Listed For Sale

163 Jo-Jean Way Unit Duplex, Tavernier, FL 33070
- 6 Beds
- 4 Baths
- 2,240 Sq Ft
- Built 1984
163 Jo-Jean Way Unit Duplex, Tavernier, FL 33070

Last Sold Summary
- 3% Above List Price
- $353/SF
- 42 Days On Market
Last Sold Price $790,000

Last Listing Agent Aryl and Pati Robison RE/MAX

/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 4,200 sq

Sandra Tuttle

Island Welcome Real Estate

(645) 300-4633

421 La Fitte Rd, Little Torch Key, FL 33042
/5
$1,650 per month
- 1 Bath
- 450 Sq Ft
- Apartment for Rent
103365 Overseas Hwy Unit B, Key Largo, FL 33037

Newly Remodeled Studio Apartment featuring all New Stainless Steal Appliances. Conveniently located close to shopping, schools, restaurants, and more. Move -In Ready.

Tracey Petrusha Venture Realty Group

103365 Overseas Hwy Unit B, Key Largo, FL 33037
/29
$740,000 Sold Oct 31, 2025

27138 Dolphin Rd, Summerland Key, FL 33042
- 3 Beds
- 2 Baths
- 1,320 Sq Ft
- Built 2022
Last Sold Summary
- 14% Below List Price
- $561/SF
- 181 Days On Market
Current Estimated Value $734,951

Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.

27138 Dolphin Rd, Summerland Key, FL 33042

/18
Est $267,784 Not Listed For Sale

325 Calusa St Unit 122, Key Largo, FL 33037
325 Calusa St Unit 122, Key Largo, FL 33037

Last Sold Summary
- 7% Above List Price
- 51 Days On Market
Last Sold Price $250,000

Last Listing Agent Kelly Randin RE/MAX

/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 Real Estate Co

(786) 744-6884

0 Dominica Ln Unit 615842, Ramrod Key, FL 33042
/83
$18,000 per month
- 4 Beds
- 4 Baths
- 2,300 Sq Ft
- House for Rent
96180 Overseas Hwy Unit 1, Key Largo, FL 33037

UNIQUE KEY LARGO WATERFRONT ESTATE | PRIVATE SANDY BEACH + DOCK | 4BD/4BA | POOL | ~0.90 ACREWelcome to your own slice of the Keys—an exceptional waterfront retreat in Key Largo featuring a private sandy beach, dock, and resort-style outdoor living on approximately 0.90 acres. Designed for effortless coastal living and entertaining, this home offers 4 bedrooms and 4 bathrooms with seamless

Alex Lipzer Key Biscayne Realty Group, Inc

96180 Overseas Hwy Unit 1, Key Largo, FL 33037
/31
$1,550,000 Sold Jun 18, 2025

1401 Grinnell St, Key West, FL 33040
- 2 Beds
- 3 Baths
- 1,008 Sq Ft
- Built 2003
Last Sold Summary
- 6% Below List Price
- $1,538/SF
- 95 Days On Market
Current Estimated Value $1,605,942

Last Listing Agent Brenda Donnelly Brenda Donnelly Real Estate LLC

1401 Grinnell St, Key West, FL 33040

/7
Est $736,432 Not Listed For Sale

2601 S 2601 Roosevelt Blvd Unit 302A, Key West, FL 33040
- 2 Beds
- 1 Bath
- 980 Sq Ft
- Built 1967
2601 S 2601 Roosevelt Blvd Unit 302A, Key West, FL 33040

Last Sold Summary
- $755/SF
- 2 Days On Market
Last Sold Price $740,000

Last Listing Agent Patricia McGrath Keller Williams Key West Compass Realty

/23
$730,000
- 3 Beds
- 3 Baths
- 1,344 Sq Ft
5435 5th Ave, Key West, FL 33040

NEW LISTING! This beautiful 3-bedroom, 3-bath home offers a perfect blend of character and convenience n Stock Island location. With 10ft ceilings and an inviting layout, it feels open and airy, while lush, mature mango trees create a private tropical retreat. A unique feature of this home is its front and back entrances on two separate streets, adding extra accessibility and ease. One of the

The Wesley Group

Bascom Grooms Real Estate (KW)

(786) 386-2131

5435 5th Ave, Key West, FL 33040
/25
$1,800 per month
- 1 Bed
- 1 Bath
- Property for Rent
325 Calusa St Unit 5, Key Largo, FL 33037

Beautifully maintained residence in the heart of Key Largo! This bright and spacious unit offers a comfortable layout with great natural light and a relaxed Florida Keys lifestyle. Conveniently located near restaurants, shops, marinas, and main roads, making daily living and commuting easy. Ideal for tenants looking to enjoy island living while staying close to all essentials. Schedule your

Sandra Alayon Keller Williams Realty International Lifestyles

325 Calusa St Unit 5, Key Largo, FL 33037
/44
$2,595,000 Sold Nov 13, 2025

628 William St, Key West, FL 33040
- 3 Beds
- 3 Baths
- 1,524 Sq Ft
- Built 1928
Last Sold Summary
- 12% Below List Price
- $1,703/SF
- 9 Days On Market
Current Estimated Value $2,588,853

Last Listing Agent Paige Bethel Island Home Realty Inc.

628 William St, Key West, FL 33040

/4
Not Listed For Sale

97 Avenue B, Key Largo, FL 33037
- 2 Beds
- 1 Bath
- 1,392 Sq Ft
- Built 1968
97 Avenue B, Key Largo, FL 33037

Last Sold Summary
- $201/SF
- 6 Days On Market
Last Sold Price $280,000

Last Listing Agent Maryann Warren Coldwell Banker - Ft. Lauderdale

/15
$299,000
- Land
5555 College Rd Unit 4, Key West, FL 33040

Discover your perfect docking solution with this 60 foot boat slip (65 foot LOA) located at the sheltered and protected Sunset Marina in Key West. Positioned on the Gulf side of Key West, this slip provides deep water access, ideal for both large and small vessels. At the entrance to the property owners will find an electric gate providing increased security. Owners will enjoy the exclusive

Cardenas & Krug Team

Coastal Collection Real Estate Inc.

(786) 840-1384

5555 College Rd Unit 4, Key West, FL 33040
/38
$5,500 per month
- 4 Beds
- 3 Baths
- House for Rent
251 Pueblo St, Tavernier, FL 33070

Located in the desirable Indian Waterways neighborhood on Plantation Key. Canal-front home with private dockage and a layout well suited for comfortable long-term living in the Florida Keys. The main living area is on the second level and features an open, light-filled floor plan with large windows and vibrant coastal decor. The primary bedroom includes a queen bed, an ensuite bath, and access to

Jocelyn Marzella Ocean Sotheby's International Realty

251 Pueblo St, Tavernier, FL 33070
/51
$1,600,000 Sold Apr 08, 2025

174 Westminster Dr, Tavernier, FL 33070
- 3 Beds
- 2 Baths
- 1,648 Sq Ft
- Built 1974
Last Sold Summary
- 7% Below List Price
- $971/SF
- 62 Days On Market
Last Listing Agent Lorie Leal American Caribbean Real Estate, Christie's International Real Estate

174 Westminster Dr, Tavernier, FL 33070

/35
Est $235,105 Not Listed For Sale

701 Spanish Main Dr Unit 647, Cudjoe Key, FL 33042
701 Spanish Main Dr Unit 647, Cudjoe Key, FL 33042

Last Sold Summary
- 8% Above List Price
- 22 Days On Market
Last Sold Price $217,000

Last Listing Agent Kelly Gardner Bluescape Real Estate

/22
$679,000
- 2 Beds
- 2 Baths
- 1,040 Sq Ft
19591 Navajo St, Summerland Key, FL 33042

INDIAN MOUNDS SPECIAL!!!! Two balconies with ocean views and a hot tub to enjoy them with!!! Just one block from the private community boat ramp, this elevated 2 bed, 2 bath home sits on a large oversized corner lot. There is plenty of room for parking your toys and a downstairs enclosure for additional storage. Hardibacker siding and a metal roof provide peace of mind.Upon entering, you'll find

Mike Kane

Internet Realty of the Florida Keys

(645) 230-1301

19591 Navajo St, Summerland Key, FL 33042
/37
$15,000 per month
- 4 Beds
- 2 Baths
- 2,000 Sq Ft
- House for Rent
309 Calzada de Bougainvillea, Marathon, FL 33050

4/2 renovated furnished home steps from Sombrero Beach. features pool with new heater/chiller, a private boat dock with new Power Pedestal, a fish cleaning station with water & accommodates up to 50 ft vessels. With only minutes from the Atlantic and steps to the Beach, this is an ideal location. The Light & bright kitchen has been completely remodeled and boasts new state of the art Cafe

Thania Moses Zeff Realty LLC,

309 Calzada de Bougainvillea, Marathon, FL 33050
/47
$1,100,000 Sold Jun 27, 2025

21014 7th Ave, Summerland Key, FL 33042
- 3 Beds
- 2 Baths
- 1,361 Sq Ft
- Built 1988
Last Sold Summary
- 19% Below List Price
- $808/SF
- 102 Days On Market
Current Estimated Value $1,101,593

Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

21014 7th Ave, Summerland Key, FL 33042

/32
Est $1,803,977 Not Listed For Sale

87851 Old Hwy Unit P43, Islamorada, FL 33036
- 4 Beds
- 3 Baths
- 2,668 Sq Ft
- Built 1989
87851 Old Hwy Unit P43, Islamorada, FL 33036

Last Sold Summary
- 10% Below List Price
- $750/SF
- 26 Days On Market
Last Sold Price $2,000,000

Last Listing Agent Alina Davis Coldwell Banker Schmitt Islamorada

/46
$549,000
- 2 Beds
- 3 Baths
- 1,344 Sq Ft
601 W Ocean Dr Unit 105D, Key Colony Beach, FL 33051

Positioned along the sandy shoreline of Key Colony Beach, this beautifully updated 2 Bedroom, 2.5 Bathroom second-floor residence at The Cay offers an exceptional blend of coastal comfort and resort-style living. Nestled within a charming beachfront community on the Atlantic Ocean, the property enjoys direct access to one of the few natural sandy beaches in the Middle Keys along with a relaxed,

Lisa Ferringo

Coldwell Banker Schmitt Real Estate Co

(645) 225-1947

601 W Ocean Dr Unit 105D, Key Colony Beach, FL 33051
/6
$2,000 per month
- 1 Bed
- 1 Bath
- 1,347 Sq Ft
- House for Rent
75 Coral Dr, Key Largo, FL 33037

Beautiful Location in the Heart of Key Largo. Lots of excellent Restaurants and Key Largo Community Park nearby/walking distance. Brand new Appliances include Refrigerator, Range, and Microwave.

Tate Gettinger Florida Realty of Miami Corp

75 Coral Dr, Key Largo, FL 33037
/7
$4,275,000 Sold Mar 04, 2026

231 E Shore Dr Unit 7, Summerland Key, FL 33042
- 5 Beds
- 5.5 Baths
- 3,119 Sq Ft
- Built 2025
Last Sold Summary
- 1% Below List Price
- $1,371/SF
- 114 Days On Market
Last Listing Agent Stephanie Marinucci Serhant Florida LLC - Delray Beach Office

231 E Shore Dr Unit 7, Summerland Key, FL 33042

/43
Est $414,381 Not Listed For Sale

5301 Ocean Terrace Unit 5, Marathon, FL 33050
- 2 Beds
- 1 Bath
- 776 Sq Ft
- Built 1971
5301 Ocean Terrace Unit 5, Marathon, FL 33050

Last Sold Summary
- $535/SF
- 59 Days On Market
Last Sold Price $415,000

Last Listing Agent Ally Kelley Ocean Sotheby's International Realty

/37
$799,000
- 3 Beds
- 2 Baths
- 1,404 Sq Ft
91 Sirius Ln, Key West, FL 33040

Welcome to 91 Sirius Lane, a beautifully remodeled canal-front retreat in the heart of Geiger Key's sought-after Tamarac Park, an established boating community just 15 miles outside of Key West. This 2-bedroom + bonus Den/3rd Bedroom and Florida Room, 2 Bath home offers 1,404 sq ft of updated living space on a 5,850 sq ft lot with 45 feet of concrete dockage. Boaters will love the fantastic deep

Lisa Ferringo

Coldwell Banker Schmitt Real Estate Co

(786) 386-0497

91 Sirius Ln, Key West, FL 33040
/14
$5,900 per month
- 2 Beds
- 2 Baths
- 1,075 Sq Ft
- House for Rent
251 Bougainvillea St, Tavernier, FL 33070

Canal front Plantation Key Colony home offering 40' of dock space with a 6,000lb boat lift, boat ramp and quick access to the bay. Will be available starting April 1st. This 2b/2b updated two-story concrete home is fully fenced, has a screened-in porch, carport, and plenty of space for additional parking. Great location near Coral Shores High School, Plantation Key elementary school, Tavernier

Kenneth Smith American Caribbean Real Estate, Christie's International Real Estate

251 Bougainvillea St, Tavernier, FL 33070
/32
$700,000 Sold May 14, 2025

226 Newfound Blvd, Big Pine Key, FL 33043
- 2 Beds
- 2 Baths
- 960 Sq Ft
- Built 1990
Last Sold Summary
- 3% Below List Price
- $729/SF
- 17 Days On Market
Current Estimated Value $723,248

Last Listing Agent Madeleine Lowe Expert Realty LLC (HQ)

226 Newfound Blvd, Big Pine Key, FL 33043

/44
Est $907,378 Not Listed For Sale

103 Costa Bravo Dr Unit 103, Islamorada, FL 33036
- 2 Beds
- 1.5 Baths
- 1,206 Sq Ft
- Built 1974
103 Costa Bravo Dr Unit 103, Islamorada, FL 33036

Last Sold Summary
- 1% Above List Price
- $746/SF
- 26 Days On Market
Last Sold Price $900,000

Last Listing Agent Rhonda Simonds-Brewer American Caribbean Real Estate, Christie's International Real Estate

/36
$750,000
- Land
- 9.26 Acres
- $80,995 per Acre
0 Niles Rd, Summerland Key, FL 33042

Discover the perfect opportunity to build your dream home in the Lower Keys on this desirable parcel located on Summerland Key, FL. Set within a peaceful residential neighborhood, this property offers an inviting blend of tranquility and convenience—just minutes from US-1, local marinas, boat ramps, dining, beaches, and world-class fishing. Enjoy the relaxed island lifestyle, tropical breezes,

Javier Santana

Sunland Real Estate, LLC.

(786) 504-0768

0 Niles Rd, Summerland Key, FL 33042
/8
$1,900 per month
- 2 Beds
- 1 Bath
- 744 Sq Ft
- Property for Rent
65821 Overseas Hwy Unit 110, Long Key, FL 33001

Escape to the Florida Keys! This charming fully furnished 2BR/1BA manufactured home is available for short-term rental and conveniently located near everything the Keys are known for—sunshine, island vibes, and outdoor adventures. Ready for you to enjoy the most amazing weather, relax, and make memories. Ideal for families or anyone looking for a comfortable, easy getaway in paradise. Utilities

Milena Duenas Chez Realty, LLC.

65821 Overseas Hwy Unit 110, Long Key, FL 33001
/54
$950,000 Sold Aug 01, 2025

65821 Overseas Hwy #287 & 288, Long Key, FL 33001
- Land
- 0.04 Acre
- $21,590,909 per Acre
Last Sold Summary
- 40% Below List Price
- 58 Days On Market
Last Listing Agent Sam Fugina Marlin Realty Inc

65821 Overseas Hwy #287 & 288, Long Key, FL 33001

/51
Not Listed For Sale

701 Spanish Main Dr Unit 167, Cudjoe Key, FL 33042
- 2 Beds
- 2 Baths
- 864 Sq Ft
- Built 2006
701 Spanish Main Dr Unit 167, Cudjoe Key, FL 33042

Last Sold Summary
- $899/SF
- 27 Days On Market
Last Sold Price $777,000

Last Listing Agent Kelly Gardner Bluescape Real Estate

Showing Results 561 - 600, Page 15 of 18

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