Summerland Key, FL Homes

/4
$100,000

Pending
- Land
- 1.01 Acres
- $99,010 per Acre
0 Acosta Trail Unit MFRS5141973, Sugarloaf Key, FL 33042

Vacant 1.01-acre parcel on Acosta Trail in Upper Sugarloaf Key, Monroe County, FL. Approx. 20 miles to Key West, 10 miles to Big Pine Key, and 5 miles to Cudjoe Key. Unimproved land offering future development or investment potential in the Lower Florida Keys. Additional 1.01-acre lot on Mira Rd (behind subject property) also available for sale. Buyer to verify zoning, ROGO status, flood zone,

Eugenia Hernandez PREMIUM PROPERTIES R.E SERVICE

0 Acosta Trail Unit MFRS5141973, Sugarloaf Key, FL 33042
/57
$1,550,000

Sold Mar 02, 2026

270 Airport Dr S, Summerland Key, FL 33042
- 3 Beds
- 3 Baths
- 1,275 Sq Ft
- Built 1980
Last Sold Summary
- 30% Below List Price
- $1,216/SF
- 63 Days On Market
Current Estimated Value $1,539,691

Last Listing Agent Solaris Gregory Expert Realty LLC (HQ)

270 Airport Dr S, Summerland Key, FL 33042

/45
Est $1,178,267

Not Listed For Sale

23058 Sailfish Ln, Summerland Key, FL 33042
- 3 Beds
- 3 Baths
- 1,280 Sq Ft
- Built 1980
23058 Sailfish Ln, Summerland Key, FL 33042

Last Sold Summary
- 145 Days On Market
Last Listing Agent Jan Fritz Coldwell Banker Schmitt RE Co.

/38
$1,270,000

$120K PRICE DROP
- 3 Beds
- 2 Baths
- 1,320 Sq Ft
174 Tortuga Ln, Cudjoe Key, FL 33042

Florida Keys Living at Its Best! Welcome to 174 Tortuga Lane, a beautifully maintained waterfront home in the heart of Cudjoe Key, where world-class fishing, boating, and island living are in your backyard. With 37 feet of dockage, you'll have quick access to the Atlantic, backcountry waters, and some of the best fishing the Florida Keys has to offer. Built in 2020 for peace of mind and

Sarah Bixby eXp Realty LLC

174 Tortuga Ln, Cudjoe Key, FL 33042
/60
$930,000

Sold May 01, 2026

29182 Orchid Ln, Big Pine Key, FL 33043
- 4 Beds
- 3 Baths
- 2,056 Sq Ft
- Built 1988
Last Sold Summary
- 6% Below List Price
- $452/SF
- 41 Days On Market
Current Estimated Value $939,090

Last Listing Agent Dawn Gonet Berkshire Hathaway HomeServices Knight & Gardner Realty

29182 Orchid Ln, Big Pine Key, FL 33043

/16
Est $1,927,453

Not Listed For Sale

23076 Tarpon Ln, Summerland Key, FL 33042
- 2 Beds
- 2 Baths
- 1,122 Sq Ft
- Built 1975
23076 Tarpon Ln, Summerland Key, FL 33042

Last Sold Summary
- 82 Days On Market
Last Listing Agent Lisa Lennon Berkshire Hathaway HomeServices Knight & Gardner Realty

/28
$520,000

$5K PRICE DROP
- 2 Beds
- 1 Bath
- 812 Sq Ft
29284 Coconut Palm Dr, Big Pine Key, FL 33043

Escape to your own private tropical oasis in the heart of Big Pine Key. Hidden behind lush mature landscaping and swaying palms, this charming 2-bedroom, 1-bath home offers the privacy, tranquility, and island lifestyle that make the Lower Keys so desirable. The flood policy is $977 and assumable!! Situated on a 6,000-square-foot lot in the sought-after Eden Pines neighborhood, this concrete home

Jaime Caballero Key West Vacation Properties & Realty, LLC (KW)

29284 Coconut Palm Dr, Big Pine Key, FL 33043
/29
$235,000

Sold Oct 31, 2025

701 Spanish Main Dr Unit 621, Cudjoe Key, FL 33042
- Land
- 2,078 Sq Ft
- $4,926,179 per Acre
Last Sold Summary
- 2% Below List Price
- 76 Days On Market
Current Estimated Value $252,576

Last Listing Agent Kelly Gardner Bluescape Real Estate

701 Spanish Main Dr Unit 621, Cudjoe Key, FL 33042

/27
Est $1,643,523

Not Listed For Sale

23092 Snapper Ln, Summerland Key, FL 33042
- 2 Beds
- 2 Baths
- 1,645 Sq Ft
- Built 1985
23092 Snapper Ln, Summerland Key, FL 33042

Last Sold Summary
- 7 Days On Market
Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

/39
$699,000
- 2 Beds
- 1 Bath
- 672 Sq Ft
30881 Witters Ln, Big Pine Key, FL 33043

This updated concrete cottage with all the necessities you will need to enjoy waterfront living in the Keys. This home has a metal roof, mini split A/c, updated kitchen and bath and is situated on 3 lots giving you plenty of space. It is only a very short boat ride to Boggie Channel, the only market channel to both the Atlantic and Gulf in the Lower Keys. This is a great opportunity for boaters

John Nazzaro Keller Williams Realty Premier Properties - Kendall

30881 Witters Ln, Big Pine Key, FL 33043
/45
$1,300,000

Sold Mar 03, 2026

1185 Hakluyt Ln, Summerland Key, FL 33042
- 2 Beds
- 2 Baths
- 1,152 Sq Ft
- Built 1989
Last Sold Summary
- 7% Below List Price
- $1,128/SF
- 10 Days On Market
Current Estimated Value $1,282,207

Last Listing Agent Greg MacLaren Internet Realty of the Florida Keys

1185 Hakluyt Ln, Summerland Key, FL 33042

/42
Est $1,359,207

Not Listed For Sale

1172 Coates Ln, Summerland Key, FL 33042
- 3 Beds
- 2.5 Baths
- 1,794 Sq Ft
- Built 2002
1172 Coates Ln, Summerland Key, FL 33042

Last Sold Summary
- 138 Days On Market
Last Listing Agent Michele Adams Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

/3
$799,000

$50K PRICE DROP Pending
- Land
- 10 Acres
- $79,900 per Acre
LOT 57 Rocky Rd, Sugarloaf Key, FL 33042

Rare opportunity to acquire approximately 10 acres of vacant residential land in Sugarloaf Key, an area known for its low-density character, natural surroundings, and limited land availability. Large parcels of this size are increasingly scarce in the Lower Florida Keys, positioning this property as a strategic long-term holding or future planning opportunity. On Monroe county records, the

Eugenia Hernandez PREMIUM PROPERTIES R.E SERVICE

LOT 57 Rocky Rd, Sugarloaf Key, FL 33042
/42
$880,000

Sold Jun 25, 2026

27415 Barbuda Ln, Ramrod Key, FL 33042
- 3 Beds
- 2 Baths
- 1,408 Sq Ft
- Built 2008
Last Sold Summary
- 30% Below List Price
- $625/SF
- 375 Days On Market
Current Estimated Value $935,332

Last Listing Agent Lisa Frins Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

27415 Barbuda Ln, Ramrod Key, FL 33042

/55
Est $1,777,885

Not Listed For Sale

22925 John Avery Ln, Summerland Key, FL 33042
- 4 Beds
- 4 Baths
- 2,638 Sq Ft
- Built 1993
22925 John Avery Ln, Summerland Key, FL 33042

Last Sold Summary
- 164 Days On Market
Last Listing Agent Jonathan Minerick Homecoin.com

/9
$12,040

$2K PRICE DROP
- 4 Beds
- 3 Baths
- 2,855 Sq Ft
28502 Channel View Dr, Little Torch Key, FL 33042

This is a 3 story furnished or unfurnished 4 bedroom 3 bathroom home with a water view of the gulf in the Little Torch Cottages community of townhomes. There are 2 heated and chilled community pools, a gym, a sauna, a marina with boat ramp, bbq, exterior yard games and boat slip available for an extra charge. Kayaks and paddle boards are available for community usage.

Joseph Danieli AKT Realty LLC

28502 Channel View Dr, Little Torch Key, FL 33042
/7
$3,500

Sold May 24, 2026

19525 Date Palm Dr, Summerland Key, FL 33042
- 3 Beds
- 2 Baths
- 1,200 Sq Ft
- Built 2006
Last Sold Summary
- 9% Below List Price
- $3/SF
- 20 Days On Market
Current Estimated Value $793,317

Last Listing Agent Cliff Glansen FlatFee.com

19525 Date Palm Dr, Summerland Key, FL 33042

/2
Est $1,256,374

Not Listed For Sale

22943 Dirk Ln, Summerland Key, FL 33042
- 3 Beds
- 2 Baths
- 1,598 Sq Ft
- Built 1998
22943 Dirk Ln, Summerland Key, FL 33042

/12
$460,000

$35K PRICE DROP
- Land
- 2,178 Sq Ft
- $9,200,000 per Acre
701 Spanish Main Dr Unit 84, Cudjoe Key, FL 33042

Rare opportunity to own a transient (1-day minimum) rental RV lot in the Lower Keys. Located in a quiet, well-kept community, this buildable lot is perfect for your RV or for building a custom Keys getaway HomeThe property includes a 35-foot concrete seawall, dock posts, fishing cleaning station, swim ladder, Brand new concrete slab and full hookups with water, sewer, and 30, 50, and 110-amp

Anay Ramos Miami New Realty

701 Spanish Main Dr Unit 84, Cudjoe Key, FL 33042
/2
$75,000

Sold Jun 29, 2026

Lot 16 Date Palm Dr, Sugarloaf Key, FL 33042
- Land
- 14,810 Sq Ft
- $220,588 per Acre
Last Sold Summary
- 83% Below List Price
- 346 Days On Market
Last Listing Agent Pamela Stangler Expert Realty LLC

Lot 16 Date Palm Dr, Sugarloaf Key, FL 33042

/44
Est $770,907

Not Listed For Sale

22903 Jolly Roger Dr, Summerland Key, FL 33042
- 3 Beds
- 1.5 Baths
- 1,152 Sq Ft
- Built 1972
22903 Jolly Roger Dr, Summerland Key, FL 33042

Last Sold Summary
- 108 Days On Market
Last Listing Agent Monique Thiel Sunshine State Realty Services

/8
$595,000
- Land
- 6,098 Sq Ft
- $4,250,000 per Acre
28587 Peg Leg Rd, Little Torch Key, FL 33042

Canal-front vacant land with a building permit already in process -- Permit #SFDUP-2025-0096, holding 41.5 ROGO points, buy and build later. Plans are drawn for a 3,497 square-foot, four-bedroom, three-bathroom residence with a rooftop terrace offering open ocean views. Dock and full architectural plans are included. A local builder is ready to build to the buyer's specifications, with price and

Claudette Mell Century 21 Circle- Islamorada

28587 Peg Leg Rd, Little Torch Key, FL 33042
/61
$3,900,000

Sold Feb 27, 2026

16200 Old State Rd Unit 4A, Sugarloaf Key, FL 33042
- 3 Beds
- 2 Baths
- 1,964 Sq Ft
- Built 2024
Last Sold Summary
- 2% Below List Price
- $1,986/SF
- 25 Days On Market
Current Estimated Value $3,861,398

Last Listing Agent Madeleine Young Island Welcome Real Estate LLC

16200 Old State Rd Unit 4A, Sugarloaf Key, FL 33042

/70
Est $791,208

Not Listed For Sale

22933 Buccaneer Ln, Summerland Key, FL 33042
- 2 Beds
- 2 Baths
- 1,088 Sq Ft
- Built 1995
22933 Buccaneer Ln, Summerland Key, FL 33042

Last Sold Summary
- 74 Days On Market
Last Listing Agent Bobby Baker Brightwild Real Estate

/10
$1,450,000
- Land
- 6,098 Sq Ft
- $10,357,143 per Acre
00000 Lagoon Dr, Summerland Key, FL 33042

Excellent opportunity to build your dream in paradise. This 6,140 sq foot lot with 70.65 ft. of water frontage has a beautiful open water and ocean view. This is the last lot available in this established subdivision Summerland Cove. Easy access to both the Atlantic Ocean and the Gulf of Mexico.

Marc Ulanowski Equestrian Sotheby's International Realty

00000 Lagoon Dr, Summerland Key, FL 33042
/36
$685,000

Sold Oct 15, 2025

701 Spanish Main Dr Unit 77, Cudjoe Key, FL 33042
- 2 Beds
- 1 Bath
- 864 Sq Ft
- Built 2010
Last Sold Summary
- 16% Below List Price
- $793/SF
- 164 Days On Market
Last Listing Agent Patti Nickless Coldwell Banker Schmitt Lower Keys (KW)

701 Spanish Main Dr Unit 77, Cudjoe Key, FL 33042

/2
Est $820,741

Not Listed For Sale

201 Cutthroat Dr, Summerland Key, FL 33042
- 2 Beds
- 2 Baths
- 1,056 Sq Ft
- Built 1983
201 Cutthroat Dr, Summerland Key, FL 33042

/22
$699,000

$150K PRICE DROP
- 4 Beds
- 2.5 Baths
- 1,924 Sq Ft
1433 Sunset Rd, Big Pine Key, FL 33043

699,000 for 2 units. Great price reduction on income producing CBS duplex in Big Pine Key. Good boating with direct access to Bogie Channel. Large lot with full seawall. Interior is cute and tidy and would be easy to rent or live in one side and generate extra income. Fully furnished.insurance ESTIMATE with owner occupied on 1 unit: 1410 Homeowners, Flood 4000.00windstorm 8530.00.

Cheryl Moses Action Keys Realty of the Lower FL Keys LLC

1433 Sunset Rd, Big Pine Key, FL 33043
/39
$900,000

Sold Jul 02, 2026

21073 7th Ave, Summerland Key, FL 33042
- 3 Beds
- 2 Baths
- 2,198 Sq Ft
- Built 1975
Last Sold Summary
- $409/SF
- 0 Days On Market
Current Estimated Value $1,295,547

Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.

21073 7th Ave, Summerland Key, FL 33042

/47
Est $2,332,246

Not Listed For Sale

22684 Jolly Roger Dr, Summerland Key, FL 33042
- 3 Beds
- 2 Baths
- 1,819 Sq Ft
- Built 1977
22684 Jolly Roger Dr, Summerland Key, FL 33042

Last Sold Summary
- 17 Days On Market
Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

/23
$705,000

$90K PRICE DROP Under Contract
- 3 Beds
- 2 Baths
- 1,232 Sq Ft
180 Sugarloaf Dr, Summerland Key, FL 33042

**BACK ON THE MARKE, BUYERS FINANCING FELL THROUGH **This charming 3 bedroom 2 bath house in Sugarloaf Shores sits on an oversized 12,000 sq ft lot. Fenced for privacy with plenty of room for a pool, park your boat or RV. Outside you have a large paver patio, outdoor shower and lush gardens. Step inside to find a warm inviting interior space, remodeled kitchen and bathroom, bonus HUGE

Jenny Perry Preferred Properties (KW)

180 Sugarloaf Dr, Summerland Key, FL 33042
/2
$675,000

Sold Sep 19, 2025

Unlisted Address
- 3 Beds
- 1 Bath
- 1,162 Sq Ft
- Built 1978
Last Sold Summary
- 16% Below List Price
- $581/SF
- 147 Days On Market
Current Estimated Value $669,000

Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real E

Unlisted Address

/34
Est $799,140

Not Listed For Sale

191 Doubloon Ln, Summerland Key, FL 33042
- 2 Beds
- 2 Baths
- 1,340 Sq Ft
- Built 1963
191 Doubloon Ln, Summerland Key, FL 33042

Last Sold Summary
- 10 Days On Market
Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

/49
$2,450,000

$350K PRICE DROP
- 3 Beds
- 4 Baths
- 2,087 Sq Ft
31473 Warner St, Big Pine Key, FL 33043

Welcome to an exquisite open-water retreat in Big Pine Key, an unparalleled blend of modern luxury and authentic Keys lifestyle. This completely updated and remodeled 3BD/4BA pool home offers panoramic water views from every angle, setting the stage for endless sunrises, sunsets, and starry nights. Designed with sophistication and comfort in mind, each bedroom is an ensuite, ensuring privacy and

Michele Adams Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

31473 Warner St, Big Pine Key, FL 33043
/66
$775,000

Sold Aug 03, 2026

701 Spanish Main Dr Unit 172, Cudjoe Key, FL 33042
- 2 Beds
- 2 Baths
- 842 Sq Ft
- Built 2006
Last Sold Summary
- 9% Below List Price
- $920/SF
- 231 Days On Market
Last Listing Agent Ian Calderwood Bluescape Real Estate- Venture

701 Spanish Main Dr Unit 172, Cudjoe Key, FL 33042

/19
Est $711,433

Not Listed For Sale

134 Tortuga Ln, Summerland Key, FL 33042
- 3 Beds
- 2 Baths
- 1,056 Sq Ft
- Built 1988
134 Tortuga Ln, Summerland Key, FL 33042

Last Sold Summary
- 4 Days On Market
Last Listing Agent Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

/143
$19,750,000
- 6 Beds
- 6.5 Baths
- 4,402 Sq Ft
15760 Old State Road 4a, Summerland Key, FL 33042

Rare Private Sandy Beach - Oceanfront Estate with endless open ocean views, just 30 minutes to Key West! This is a once-in-a-lifetime opportunity to own over 5 acres of sprawling oceanfrontage on exclusive Sugarloaf Beach, with over 500 feet of pristine sandy shoreline. Zoned Sub Urban Residential, this rare estate offers unmatched potential--create a private luxury compound, a boutique resort

Lisa Swanson Berkshire Hathaway HomeServices Knight & Gardner Realty

15760 Old State Road 4a, Summerland Key, FL 33042
/54
$700,000

Sold Aug 03, 2026

701 Spanish Main Dr Unit 97, Cudjoe Key, FL 33042
- 2 Beds
- 2 Baths
- 640 Sq Ft
- Built 2018
Last Sold Summary
- 22% Below List Price
- $1,094/SF
- 152 Days On Market
Last Listing Agent Jan Fritz Coldwell Banker Schmitt RE Co.

701 Spanish Main Dr Unit 97, Cudjoe Key, FL 33042

/77
Est $6,047,259

Not Listed For Sale

200 Erie Dr, Summerland Key, FL 33042
- 4 Beds
- 4 Baths
- 4,514 Sq Ft
- Built 2002
200 Erie Dr, Summerland Key, FL 33042

Last Sold Summary
- 295 Days On Market
Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

/2
$44,000

Pending
- Land
- 21,780 Sq Ft
- $88,000 per Acre
0 Unassigned Unit 620155, No Name Key, FL 33043

ROGO Land Dedication Lot worth 2 points with completed paperwork and Monroe County Letter of Eligibility on file. No hidden costs or additional processing required. Cost effective opportunity to help accelerate your permitting timeline. Parcel is not buildable and is offered for land dedication purposes only.

Cliff Glansen FlatFee.com

0 Unassigned Unit 620155, No Name Key, FL 33043

Showing Results 641 - 680, Page 17 of 18

Florida Monroe County

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Summerland Key, FL Homes

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