Monroe County, FL Homes

/41
$550,000
- 3 Beds
- 1 Bath
- 988 Sq Ft
30372 Palm Dr, Big Pine Key, FL 33043

Well-priced Keys living starts here! This 12,500 sq. ft. double lot offers ample parking and room to add a pool, garage, tiki hut, or more. In 2022, the current owner added a metal roof, impact-resistant windows and doors, and Mitsubishi mini-split A/C units. Inside, the home features a spacious great room, three bedrooms, one updated bath, and tile floors throughout. Outside, you'll find a solar

Patti Nickless

Coldwell Banker Schmitt RE Co.

(888) 376-2422

30372 Palm Dr, Big Pine Key, FL 33043
/2
$3,200 Per Month
- 2 Beds
- 1 Bath
- 816 Sq Ft
- 717 Emma - B
717 Emma St Unit 717-B Emma, Key West, FL 33040

Super cute 2 bed, 1 bath available soon.

717 Emma St Unit 717-B Emma, Key West, FL 33040
/16
$500,000

Sold Jul 10, 2025

9 7th St, Key Colony Beach, FL 33051
- 2 Beds
- 2 Baths
- 885 Sq Ft
- Built 1966
Last Sold Summary
- $565/SF
- 0 Days On Market
Current Estimated Value $571,059

Last Listing Agent Karen Raspe, PA Ocean Sotheby's International

9 7th St, Key Colony Beach, FL 33051

/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

/34
$749,900
- 3 Beds
- 2 Baths
- 1,431 Sq Ft
28110 Dorothy Ave, Little Torch Key, FL 33042

Island living comes easy here, with a free community boat ramp, nearby waterfront basin, and natural Lower Keys scenery all close to home. Set on a large 7,814 sq. ft. corner lot along State Road 4A in Ladies Acre, this 3 bedroom, 2 bath property offers 1,431 sq. ft. of comfortable living space surrounded by mature tropical greenery that adds privacy and natural beauty. Inside, the open living,

Lisa Ferringo

Coldwell Banker Schmitt Real Estate Co

(645) 220-1204

28110 Dorothy Ave, Little Torch Key, FL 33042
/12
$5,000 Per Month
- 3 Beds
- 2 Baths
- 1,580 Sq Ft
- House for Rent
94825 Overseas Hwy Unit 8, Key Largo, FL 33037

Benson Charles Help You Save Realty

94825 Overseas Hwy Unit 8, Key Largo, FL 33037
/6
$1,937,500

Sold Jun 05, 2026

1058 Buttonwood Dr E, Summerland Key, FL 33042
- 3 Beds
- 2 Baths
- 1,767 Sq Ft
- Built 2001
Last Sold Summary
- $1,096/SF
- 0 Days On Market
Current Estimated Value $1,592,238

Last Listing Agent Lisa Swanson Berkshire Hathaway HomeServices Knight & Gardner Realty

1058 Buttonwood Dr E, Summerland Key, FL 33042

/6
Est $316,560

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

/25
$445,000

$50K PRICE DROP
- 1 Bed
- 1 Bath
- 620 Sq Ft
140 Gumbo Limbo Dr, Key Largo, FL 33037

The Perfect Getaway in the Florida Keys! This adorable and quaint vintage cottage is tucked between beautiful trees on 10,500 sq ft. Two oversized corner lots offer privacy and a ton of room to spread out, unwind, and enjoy the island lifestyle The cozy 1/1 bungalow comes fully furnished and full of personality--indoor tiki bar, open kitchen with granite and oak cabinets, custom oak flooring in

Terry Canto

American Caribbean Real Estate, Christie's International Real Estate

(866) 856-2911

140 Gumbo Limbo Dr, Key Largo, FL 33037
/27
$2,500 Per Month
- 1 Bed
- 1 Bath
- 610 Sq Ft
- Furnished 1 bedroom 1 Bathroom in Old Town
327 Margaret St, Key West, FL 33040

This second floor one bedroom apartment has one of the most desirable walking locations in Historic Old Town. Located only 1.5 blocks from the Historic Seaport and 4.5 blocks from Duval Street. One bedroom one bath floor plan maximizes the space in this sunny and airy tree top apartment. Comfortable Queen size bed will inspire sweet dreams. Beautiful new furnishings throughout include the

327 Margaret St, Key West, FL 33040
/61
$700,000

Sold Jun 12, 2025

202 51st St, Marathon, FL 33050
- 2 Beds
- 1 Bath
- 1,053 Sq Ft
- Built 1971
Last Sold Summary
- 12% Below List Price
- $665/SF
- 29 Days On Market
Last Listing Agent Mykael Marinelli American Caribbean Real Estate, Christie's International Real Estate

202 51st St, Marathon, FL 33050

/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

/29
$1,199,000

Under Contract
- 3 Beds
- 2 Baths
- 1,125 Sq Ft
104 8th Ln, Key Largo, FL 33037

Private Waterfront Retreat in Winston Waterways!A rare opportunity awaits to own in one of Key Largo's most desirable boating communities. This beautifully maintained stilt home in the highly sought-after Winston Waterways neighborhood offers 3 bedrooms, 2 baths, and the perfect blend of privacy, exceptional boating access, and authentic island living.Sweeping water views stretch from

Philip Kravitz

Coldwell Banker Schmitt Key Largo

(844) 548-2038

104 8th Ln, Key Largo, FL 33037
/52
$18,000 Per Month
- 5 Beds
- 3.5 Baths
- 4,700 Sq Ft
- House for Rent
124 S Indies Dr, Marathon, FL 33050

Available for long term lease beginning April 15th 2026. Short term is 28 day minimum rental. Welcome to paradise! This luxury custom home has it all! Only 1100 feet to the ocean inlet, no fixed bridges, 100' wide crystal clear canal, ocean views from the third-story loft, two 25k boat lifts available for up to 40' boats, double jet ski lift, paddle boards, fishing rods, and golf carts are ready

John DeMarco Re Max/5 Star Realty

124 S Indies Dr, Marathon, FL 33050
/30
$930,000

Sold Aug 01, 2025

608 Roberts Ln, Key West, FL 33040
- 2 Beds
- 2 Baths
- 1,700 Sq Ft
- Built 1933
Last Sold Summary
- 41% Below List Price
- $547/SF
- 189 Days On Market
Current Estimated Value $1,052,990

Last Listing Agent Bascom Grooms Bascom Grooms Real Estate (KW)

608 Roberts Ln, 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

/45
$1,000,000

$190K PRICE DROP Under Contract
- 2 Beds
- 2 Baths
- 1,736 Sq Ft
87851 Old Hwy Unit M32, Islamorada, FL 33036

Welcome to Ocean Harbour Condominiums, one of Islamorada's most sought-after addresses where tropical luxury meets Keys serenity. Built in 1989 and meticulously maintained, this gated oceanfront community is a true hidden gem boasting lush, resort-style grounds with hundreds of swaying palms and panoramic views that stretch endlessly across the caribbean blue Atlantic ocean. This 2-bedroom,

Krissy Carnahan

Realty ONE Group Destination (ISL)

(786) 551-1072

87851 Old Hwy Unit M32, Islamorada, FL 33036
/11
$3,500 Per Month
- 2 Beds
- 2 Baths
- 952 Sq Ft
- Townhouse for Rent
3389 Northside Dr, Key West, FL 33040

This home is in good condition and has been freshly painted throughout. The main level features a comfortable living area, dining space, full bathroom, and kitchen with freshly painted cabinets. The downstairs has almost new vinyl plank flooring, providing a clean, modern feel.Upstairs, you’ll find two bedrooms with plush newer carpeting and another full bath. Sliding glass doors off the

3389 Northside Dr, Key West, FL 33040
/40
$3,500,000

Sold May 06, 2026

59720 Overseas Hwy Unit 13, Marathon, FL 33050
- 5 Beds
- 4.5 Baths
- 3,011 Sq Ft
- Built 2023
Last Sold Summary
- 8% Below List Price
- $1,162/SF
- 835 Days On Market
Last Listing Agent Sabrina Acevedo Internet Realty of the Florida Keys Inc

59720 Overseas Hwy Unit 13, Marathon, FL 33050

/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

/33
$1,199,000
- 3 Beds
- 2 Baths
- 1,554 Sq Ft
2411 Grouper Dr, Marathon, FL 33050

Attention Investors! Owner financing opportunity with no windstorm insurance required. This beautifully maintained 3-bedroom, 2-bathroom ground-level home is perfectly positioned on a desirable flow-through canal, only several houses away from the open waters of the Gulf of Mexico. Inside, you'll find a spacious layout with an updated kitchen featuring modern finishes and stainless steel

Michelle Vanhoose

Coldwell Banker Schmitt Real Estate Co.

(645) 300-5936

2411 Grouper Dr, Marathon, FL 33050
/41
$5,865 Per Month
- 3 Beds
- 2 Baths
- 1,593 Sq Ft
- Condo for Rent
88181 Old Hwy Unit A41, Islamorada, FL 33036

Welcome to Sea Breeze 41, a refined island residence in the gated Coral Harbour Club. This spacious 3-bedroom, 2-bath condo offers elegant coastal living with a private 30' boat slip included (fits up to 33') Professionally decorated in a Tropical Modern style, The open-concept layout seamlessly connects the gourmet kitchen with stainless steel appliances and corian counter tops to the living,

Steven Koleno Beycome of Florida, LLC

88181 Old Hwy Unit A41, Islamorada, FL 33036
/6
$600,000

Sold Dec 01, 2025

101551 Overseas Hwy Unit 57, Key Largo, FL 33037
- Land
- 2,085 Sq Ft
- $12,535,252 per Acre
Last Sold Summary
- 5% Below List Price
- 8 Days On Market
Current Estimated Value $608,315

Last Listing Agent Kelly Randin RE/MAX All Keys Real Estate

101551 Overseas Hwy Unit 57, Key Largo, FL 33037

/29
Not Listed For Sale

1693 Bayview Dr, Little Torch Key, FL 33042
- 2 Beds
- 2 Baths
- 917 Sq Ft
- Built 1976
1693 Bayview Dr, Little Torch Key, FL 33042

Last Sold Summary
- 60 Days On Market

/35
$2,640,000

$110K PRICE DROP
- 4 Beds
- 3 Baths
- 1,519 Sq Ft
610 Griffin Ln, Key West, FL 33040

Privacy. Seclusion. Serenity. Tucked away at the end of a quiet lane, 610 Griffin Lane is a rare Old Town retreat--an intimate, multi-structure compound that feels worlds away from the everyday.Set on an oversized lot nearly twice the size of most in the area, the property unfolds like a private estate. The beautifully renovated two-bedroom, two-bath main residence offers effortless comfort

Cardenas & Krug Team

Coastal Collection Real Estate Inc.

(786) 933-8828

610 Griffin Ln, Key West, FL 33040
/30
$3,500 Per Month
- 2 Beds
- 1 Bath
- 826 Sq Ft
- Condo for Rent
55 Boca Chica Rd, Key West, FL 33040

Available immediately on an annual lease, this furnished 2 bedroom, 1.5 bathroom rental is located in a private gated community at the end of a quiet dead-end street. The property offers ocean views, tropical breezes, and a large private wraparound deck.The unit is just steps from one of the community pools, clubhouse, gym, and laundromat. Washer/dryer hookups are available inside the shed on the

55 Boca Chica Rd, Key West, FL 33040
/20
$865,000

Sold Feb 24, 2026

102 Snapper Creek Dr, Layton, FL 33001
- 3 Beds
- 2 Baths
- 1,056 Sq Ft
- Built 2005
Last Sold Summary
- 6% Below List Price
- $819/SF
- 72 Days On Market
Current Estimated Value $868,348

Last Listing Agent Alberto Martinez Keller Williams Capital Realty

102 Snapper Creek Dr, Layton, FL 33001

/2
Not Listed For Sale

735 26th, Marathon, FL 33050
- 2 Beds
- 1 Bath
- 1,091 Sq Ft
- Built 1967
735 26th, Marathon, FL 33050

/51
$849,900

$25K PRICE DROP
- 2 Beds
- 2 Baths
- 1,221 Sq Ft
2601 S Roosevelt Blvd Unit 223C, Key West, FL 33040

Well maintained 2BD/2BA condo that was converted from a 3BD for extra living space. Offering resort style amenities, and strong rental appeal. Unit features open living area, private balcony, impact windows and sliders. Ideal for fulltime residence, second home, or investment opportunity.located in a professionally managed waterfront community with two pools (heated), tennis courts, assigned

Shirley Carey

Berkshire Hathaway HomeServices Knight & Gardner Realty

(645) 225-1691

2601 S Roosevelt Blvd Unit 223C, Key West, FL 33040
/49
$5,800 Per Month
- 3 Beds
- 2 Baths
- 1,200 Sq Ft
- House for Rent
3770 Park Ave, Big Pine Key, FL 33043

Welcome to Caribbean Cove located in Big Pine Key. Located in the lower keys, 30 minutes from Key West. This stunning waterfront three bedroom/two bath home features an open floor plan, with a fully furnished living area and a modern kitchen. The kitchen is a culinary dream, equipped with stainless steel appliances and an oversized quartz island, surrounded by eight comfortable seats, perfect for

Mary Jo Selden DomainRealty.com LLC

3770 Park Ave, Big Pine Key, FL 33043
/22
$1,275,000

Sold Feb 09, 2026

56 Pelican Rd, Marathon, FL 33050
- 2 Beds
- 1 Bath
- 864 Sq Ft
- Built 1968
Last Sold Summary
- 20% Below List Price
- $1,476/SF
- 382 Days On Market
Current Estimated Value $1,734,939

Last Listing Agent Valeria Perez Trust Invest Real Estate Corp

56 Pelican Rd, Marathon, FL 33050

/37
Not Listed For Sale

299 Anglers Dr N Unit A, Marathon, FL 33050
- 2 Beds
- 1 Bath
- 950 Sq Ft
- Built 1980
299 Anglers Dr N Unit A, Marathon, FL 33050

Last Sold Summary
- 83 Days On Market

/43
$1,230,000

$20K PRICE DROP
- 3 Beds
- 2 Baths
- 2,368 Sq Ft
27395 Saint Lucie Ln, Summerland Key, FL 33042

Professional photos coming soon! Welcome to your piece of paradise in Breezeswept Beach Estates, where laid-back island living meets premier canal-frontage. From here, it's an easy cruise to open water--perfect for early morning fishing runs, sunset sails, or spontaneous sandbar days. Inside, this bright and breezy retreat has been thoughtfully updated with stainless steel appliances, sleek

Michelle Vanhoose

Coldwell Banker Schmitt Real Estate Co.

(786) 882-1637

27395 Saint Lucie Ln, Summerland Key, FL 33042
/22
$3,200 Per Month
- 2 Beds
- 2 Baths
- 784 Sq Ft
- Comfortable Island Rental with Outdoor Space, Storage & Flexible Living
6620 Maloney Ave, Key West, FL 33040

Welcome to 6620 Maloney Ave #14 — a versatile and comfortable rental designed for easy island living. This unfurnished home features updated flooring throughout and is perfect for bringing in your own furniture and creating a space that fits your personal style. Enjoy the convenience of an in-unit washer and dryer, wall A/C units in each bedroom for personalized comfort, and parking for two

6620 Maloney Ave, Key West, FL 33040
/53
$3,500,000

Sold Aug 08, 2025

407-415 Olivia St, Key West, FL 33040
- 6 Beds
- 5 Baths
- 3,171 Sq Ft
- Built 1964
Last Sold Summary
- 18% Below List Price
- $1,104/SF
- 134 Days On Market
Current Estimated Value $3,556,263

Last Listing Agent Brenda Donnelly Brenda Donnelly Real Estate LLC

407-415 Olivia St, Key West, FL 33040

/2
Est $852,442

Not Listed For Sale

210 Southard St Unit 9, Key West, FL 33040
- 2 Beds
- 1 Bath
- 680 Sq Ft
- Built 1991
210 Southard St Unit 9, Key West, FL 33040

Last Sold Summary
- 3 Days On Market

/26
$4,750,000
- 6 Beds
- 5 Baths
- 3,788 Sq Ft
901 Eisenhower Dr, Key West, FL 33040

FULL TRANSIENT RECEIVER ZONE with 5 ROGOS. Ahoy, dreamers and visionaries! Step into the pages of Key West lore with this enchanting waterfront property, whispering tales of Old Town charm from its perch on the edge of paradise. Built prior to 1912, and lovingly held by the same family for over a century, this sprawling 15,609 square foot lot, zoned General Commercial, awaits your masterpiece.

Damian Vantriglia

Berkshire Hathaway HomeServices Knight & Gardner Realty

(866) 497-8281

901 Eisenhower Dr, Key West, FL 33040
/7
$2,450 Per Month
- 2 Beds
- 1 Bath
- 800 Sq Ft
- Property for Rent
7 Sunset Rd Unit 5, Key Largo, FL 33037

Welcome to Paradise!!! Enjoy living in this fully renovated 1/1 Unit. This unit is located in a great neighborhood in Key Largo close to great schools and shopping and fantastic restaurants. This unit offers brand new A/C units custom kitchen including Quartz countertops and new S/S appliances. large Fully renovated Bathroom with all modern fixtures. This unit also offers impact windows and new

Germain Garcia, PA Lifestyle International Realty

7 Sunset Rd Unit 5, Key Largo, FL 33037
/31
$750,000

Sold Oct 03, 2025

1428 Virginia St, Key West, FL 33040
- 4 Beds
- 2 Baths
- 2,236 Sq Ft
- Built 1933
Last Sold Summary
- 16% Below List Price
- $335/SF
- 111 Days On Market
Current Estimated Value $809,971

Last Listing Agent Walt Lee Berkshire Hathaway HomeServices Knight & Gardner Realty

1428 Virginia St, Key West, FL 33040

/26
Est $319,745

Not Listed For Sale

21 Sombrero Blvd Unit 323, Marathon, FL 33050
- 1 Bed
- 1 Bath
- 547 Sq Ft
- Built 1986
21 Sombrero Blvd Unit 323, Marathon, FL 33050

Last Sold Summary
- 66 Days On Market

Showing Results 321 - 360, Page 9 of 18

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