Sugarloaf Key, FL Homes

/2
Est $199,913

Not Listed For Sale

825 Hawksbill Ln, Sugarloaf Key, FL 33042
- Studio
825 Hawksbill Ln, Sugarloaf Key, FL 33042

/12
$630,000

$20K PRICE DROP
- 2 Beds
- 2 Baths
- 1,010 Sq Ft
4 Shore Dr, Key West, FL 33040

Million dollar views! Ocean and Gulf views make this an affordable waterfront gem. Situated in the quiet and peaceful Bay Point neighborhood, this home is only 17 miles from Key West allowing quick city access and return to waterfront bliss. This Keys-style fish camp offers a waterfront manufactured home with 2 bedrooms and 2 baths. The side yard is a leafy oasis or reconfigured for parking.

4 Shore Dr, Key West, FL 33040
/33
$1,075,000

Sold Feb 20, 2026

17226 Jamaica Ln, Summerland Key, FL 33042
- 3 Beds
- 2 Baths
- 1,248 Sq Ft
- Built 1998
Last Sold Summary
- 10% Below List Price
- $861/SF
- 32 Days On Market
Current Estimated Value $1,100,713

Last Listing Agent Stephen Hachey Flat Fee MLS Realty

17226 Jamaica Ln, Summerland Key, FL 33042

/10
Not Listed For Sale

19 Palm Dr, Saddlebunch, FL 33040
19 Palm Dr, Saddlebunch, FL 33040

Last Sold Summary
- 67 Days On Market
Last Listing Agent Karl Helbig Sunreal Estate Inc.

/12
$599,000
- Land
- 11,950 Sq Ft
- $2,183,468 per Acre
16841 Driftwood Ln, Sugarloaf Shores, FL 33042

**Tier III Beautiful Buildable Canal Front Lot in Sugarloaf Shores!**Discover an exceptional opportunity in the prestigious Sugarloaf Shores neighborhood with this oversized canal front lot, boasting 11,950 square feet. This prime piece of real estate offers quick boating access to both the Gulf of Mexico and the Atlantic Ocean.Key features include:- **Unparalleled Location:** Just 14 miles from

Daiane Sardinas Carvalho Centennial Realty Group, LLC

16841 Driftwood Ln, Sugarloaf Shores, FL 33042
/60
$2,512,500

Sold Oct 31, 2025

1260 Sugarloaf Blvd, Summerland Key, FL 33042
- 4 Beds
- 3 Baths
- 2,886 Sq Ft
- Built 1991
Last Sold Summary
- 3% Below List Price
- $871/SF
- 60 Days On Market
Current Estimated Value $2,448,936

Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

1260 Sugarloaf Blvd, Summerland Key, FL 33042

/2
Est $2,296,535

Not Listed For Sale

305 S Point Dr, Summerland Key, FL 33042
- 3 Beds
- 2 Baths
- 2,360 Sq Ft
- Built 1986
305 S Point Dr, Summerland Key, FL 33042

/45
$1,649,000

$26K PRICE DROP
- 3 Beds
- 3 Baths
- 1,589 Sq Ft
6 Shore Dr, Key West, FL 33040

Breathtaking sunset views! Million-dollar views set the tone for this beautifully crafted 3-bedroom, 3-bath home in Saddlebunch Key, just minutes from Key West. Designed for true Keys living, the home features three levels of balconies and porches, each offering sweeping panoramic water views and unforgettable sunsets. Inside, you'll find a fully turnkey residence with thoughtful updates and

Holly Burger RE/MAX Keys Connection (KW)

6 Shore Dr, Key West, FL 33040
/25
$1,249,000

Sold Apr 28, 2026

17170 Amberjack Ln, Summerland Key, FL 33042
- 2 Beds
- 2 Baths
- 1,056 Sq Ft
- Built 1989
Last Sold Summary
- $1,183/SF
- 0 Days On Market
Current Estimated Value $1,243,030

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

17170 Amberjack Ln, Summerland Key, FL 33042

/23
Not Listed For Sale

17295 Keystone Rd, Sugarloaf Shores, FL 33042
17295 Keystone Rd, Sugarloaf Shores, FL 33042

Last Sold Summary
- 8 Days On Market
Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.

/45
$3,995,900

New Construction $254K PRICE DROP Pending
- 5 Beds
- 5.5 Baths
- 4,103 Sq Ft
231 E Shore Dr Unit 1, Key West, FL 33040

Introducing Seven Palms Cove, a one-of-a-kind new construction community that redefines luxury island living. With only seven exclusive residences available—each starting at $4 million—this private enclave offers a rare opportunity to own a slice of paradise just minutes from the heart of Key West. Each state-of-the-art home spans over 4,000 square feet and features 5 spacious bedrooms, 5.5

Christian Prakas Serhant

231 E Shore Dr Unit 1, Key West, FL 33040
/44
$1,550,000

Sold Feb 27, 2026

17094 Coral Dr, Summerland Key, FL 33042
- 3 Beds
- 3 Baths
- 1,998 Sq Ft
- Built 1982
Last Sold Summary
- 14% Below List Price
- $776/SF
- 265 Days On Market
Current Estimated Value $1,582,281

Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

17094 Coral Dr, Summerland Key, FL 33042

/6
Est $203,229

Not Listed For Sale

13 Beach Dr, Key West, FL 33040
13 Beach Dr, Key West, FL 33040

Last Sold Summary
- 149 Days On Market
Last Listing Agent Natallie Liz Island Welcome Real Estate LLC

/21
$1,050,000
- 3 Beds
- 2 Baths
- 1,296 Sq Ft
17 E Circle Dr Unit A, Key West, FL 33040

This is a single family detached, turn key home on the open water facing Sugarloaf Key. Featuring 3 bedrooms, 2 bathrooms, granite countertops, upgraded porcelain plank tile floor, solid wood cabinets, hardiboard siding, low maintenance yard, tankless water heater, energy efficient appliances and AC, large master suite, and a nice deck overlooking the bay. Full concrete slab under the home with a

Jessica Prescott Coastal Collection Real Estate Inc.

17 E Circle Dr Unit A, Key West, FL 33040
/40
$950,000

Sold Sep 17, 2025

17126 Wahoo Ln W, Sugarloaf Shores, FL 33042
- 3 Beds
- 2 Baths
- 1,152 Sq Ft
- Built 1977
Last Sold Summary
- 16% Below List Price
- $825/SF
- 85 Days On Market
Current Estimated Value $1,025,643

Last Listing Agent Sandra Tuttle Island Welcome Real Estate

17126 Wahoo Ln W, Sugarloaf Shores, FL 33042

/21
Not Listed For Sale

2950 Overseas Hwy Unit 28, Key West, FL 33040
2950 Overseas Hwy Unit 28, Key West, FL 33040

Last Sold Summary
- 115 Days On Market
Last Listing Agent Oleksandr Khiznichenko Keller Williams Key West Compass Realty

/43
$4,375,000

New Construction $4M PRICE INCREASE Pending
- 5 Beds
- 5.5 Baths
- 4,103 Sq Ft
231 E Shore Dr Unit 4, Key West, FL 33040

Introducing Seven Palms Cove, a one-of-a-kind new construction community that redefines luxury island living. With only seven exclusive residences available—each starting at $4 million—this private enclave offers a rare opportunity to own a slice of paradise just minutes from the heart of Key West. Each state-of-the-art home spans over 4,000 square feet and features 5 spacious bedrooms, 5.5

Christian Prakas Serhant

231 E Shore Dr Unit 4, Key West, FL 33040
/45
$4,325,000

Sold May 27, 2026

231 E Shore Dr Unit 3, Key West, FL 33040
- 5 Beds
- 5.5 Baths
- 4,103 Sq Ft
- Built 2025
Last Sold Summary
- 5% Above List Price
- $1,054/SF
- 266 Days On Market
Last Listing Agent Stephanie Marinucci Serhant

231 E Shore Dr Unit 3, Key West, FL 33040

/2
Not Listed For Sale

42 Beach Dr, Key West, FL 33040
- 2 Beds
- 2 Baths
- 1,110 Sq Ft
- Built 1977
42 Beach Dr, Key West, FL 33040

/10
$699,000

$26K PRICE DROP
- Land
- 8,276 Sq Ft
- $3,678,947 per Acre
17220 Angelfish Ln, Sugarloaf Shores, FL 33042

Build Your Dream Home in Sugarloaf Shores! Discover the rare opportunity to develop your very own piece of paradise in the exclusive Sugarloaf Shores! This 8,165 sq. ft. waterfront lot is high, dry, and cleared, offering a perfect blank slate for your dream home in the Florida Keys. With a full 70' concrete seawall, this property is a boater's paradise, providing direct access to both the

The Spottswood Team Truman & Co. (KW)

17220 Angelfish Ln, Sugarloaf Shores, FL 33042
/3
$225,000

Sold Nov 14, 2025

1A Palm Dr, Other Florida, FL 33040
- Land
- 2,670 Sq Ft
- $3,669,412 per Acre
Last Sold Summary
- 18% Below List Price
- 79 Days On Market
Last Listing Agent Roger Cousineau Keller Williams Key West Compass Realty

1A Palm Dr, Other Florida, FL 33040

/42
Not Listed For Sale

18 Shore Dr, Key West, FL 33040
- 2 Beds
- 2 Baths
- 846 Sq Ft
- Built 1988
18 Shore Dr, Key West, FL 33040

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

/53
$1,710,000

$89K PRICE DROP
- 4 Beds
- 2 Baths
- 2,605 Sq Ft
1481 Sugarloaf Blvd, Summerland Key, FL 33042

Welcome to this spacious canal-front retreat set on an oversized half-acre lot with endless potential. This four-bedroom, 2,605 sq ft home offers a rare combination of water access, outdoor living, and privacy. Enjoy true Florida Keys living with a private concrete boat ramp, a dock, and direct canal access leading to mangrove-lined creeks and open water just minutes away. Whether you're

Jenna Stauffer Ocean Sotheby's International Realty

1481 Sugarloaf Blvd, Summerland Key, FL 33042
/6
$14,500

Sold Sep 29, 2025

0 Vacant Land Unit 616529, Sugarloaf Key, FL 33042
- Land
- 6,098 Sq Ft
- $103,571 per Acre
Last Sold Summary
- 7% Above List Price
- 4 Days On Market
Last Listing Agent Sam Williams Coldwell Banker Schmitt Real Estate Co.

0 Vacant Land Unit 616529, Sugarloaf Key, FL 33042

/46
Est $2,811,256

Not Listed For Sale

661 Sugarloaf Blvd, Summerland Key, FL 33042
- 3 Beds
- 4 Baths
- 2,371 Sq Ft
- Built 1967
661 Sugarloaf Blvd, Summerland Key, FL 33042

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

/84
$3,199,000

$500K PRICE DROP
- 4 Beds
- 3.5 Baths
- 1,744 Sq Ft
17183 Coral Dr, Summerland Key, FL 33042

Nestled within this 280 ft of concrete walled and gated property lies a tropical oasis that epitomizes Keys living. Situated on a huge,12,000 sq ft corner lot that provides an exclusive island vibe with lots of privacy that comes complete with 200' of canal frontage, a 133' concrete dock, a new 10k lb boat lift, fish cleaning station, and travertine steps into the sparkling water for an enjoyable

Jan Fritz Coldwell Banker Schmitt RE Co.

17183 Coral Dr, Summerland Key, FL 33042
/83
$3,299,000

Sold Jul 17, 2026

17042 Starfish Ln W, Summerland Key, FL 33042
- 6 Beds
- 4.5 Baths
- 3,700 Sq Ft
- Built 1982
Last Sold Summary
- $892/SF
- 3 Days On Market
Current Estimated Value $3,216,125

Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

17042 Starfish Ln W, Summerland Key, FL 33042

/2
Est $1,730,438

Not Listed For Sale

1931 Sugarloaf Blvd, Sugarloaf Key, FL 33042
- 3 Beds
- 2 Baths
- 1,300 Sq Ft
- Built 2005
1931 Sugarloaf Blvd, Sugarloaf Key, FL 33042

/15
$644,500
- Land
- 15,200 Sq Ft
- $1,847,001 per Acre
132 Sugarloaf Dr, Summerland Key, FL 33042

Looking for your ROGO exempt slice of paradise. Look no further, build your dream home now. Large lush private lot. access from two streets to drive through. ROGO Exempt letter in hand, no waiting!! Community Marina and Ramp across the road.Great boating access to both Gulf and Atlantic. This beautiful lot awaits you to build your dream home. There is plenty space for Pool, storage, garage,

Heather Mason Coastal Collection Real Estate Inc.

132 Sugarloaf Dr, Summerland Key, FL 33042
/16
$4,330,000

Sold Jul 10, 2026

231 E Shore Dr Unit 5, Key West, FL 33040
- 5 Beds
- 5.5 Baths
- 4,103 Sq Ft
- Built 2025
Last Sold Summary
- 5% Above List Price
- $1,055/SF
- 295 Days On Market
Last Listing Agent Stephanie Marinucci Serhant

231 E Shore Dr Unit 5, Key West, FL 33040

/80
Est $6,911,383

Not Listed For Sale

17279 Oleander Ln, Sugarloaf Key, FL 33042
- 10 Beds
- 11.5 Baths
- 10,607 Sq Ft
- Built 1958
17279 Oleander Ln, Sugarloaf Key, FL 33042

Last Sold Summary
- 36 Days On Market
Last Listing Agent NON-MLS MEMBER MAR NON MLS MEMBER

/100
$8,995,000

$955K PRICE DROP
- 6 Beds
- 4.5 Baths
- 5,208 Sq Ft
16750 Old State Road 4a, Summerland Key, FL 33042

Introducing Blue Water Lagoon Estate! Experience unmatched privacy and exceptional waterfront living at this gated 2.33-acre oceanfront estate in exclusive Sugarloaf Beach — a location famously featured in the film ''True Lies''. Designed for the avid boater and those seeking a resort-style lifestyle, this 5,208 sq. ft. residence offers rare amenities and direct access to world-class fishing and

Lisa Swanson Berkshire Hathaway HomeServices Knight & Gardner Realty

16750 Old State Road 4a, Summerland Key, FL 33042
/96
$1,575,000

Sold Mar 23, 2026

17176 Bonita Ln W, Summerland Key, FL 33042
- 4 Beds
- 3 Baths
- 2,353 Sq Ft
- Built 1974
Last Sold Summary
- 7% Below List Price
- $669/SF
- 63 Days On Market
Current Estimated Value $1,637,457

Last Listing Agent Tom Mclaughlin Coldwell Banker Schmitt Real Estate Co. (KW)

17176 Bonita Ln W, Summerland Key, FL 33042

/40
Est $988,679

Not Listed For Sale

93 Venetian Way, Summerland Key, FL 33042
- 3 Beds
- 2 Baths
- 1,632 Sq Ft
- Built 1983
93 Venetian Way, Summerland Key, FL 33042

Last Sold Summary
- 11 Days On Market
Last Listing Agent Heather Mason Coastal Collection Real Estate Inc.

/2
$105,000
- Land
- 6,098 Sq Ft
- $750,000 per Acre
0 Vacant Land Unit 620095, Sugarloaf Key, FL 33042

ROGO Lots - 6 Dedication Points. Three parcels eligible for donation to Monroe County, providing a total of 6 dedication points toward a future building permit within Monroe County. The parcels may be purchased individually or together. Buyer to independently verify the dedication process, eligibility requirements, and point allocation with Monroe County.

Jenna Stauffer Ocean Sotheby's International Realty

0 Vacant Land Unit 620095, Sugarloaf Key, FL 33042
/3
$208,000

Sold Jul 13, 2026

1 Blue Water Dr, Saddlebunch, FL 33040
- Land
- 8,712 Sq Ft
- $1,040,000 per Acre
Last Sold Summary
- 8% Below List Price
- 3 Days On Market
Current Estimated Value $217,860

Last Listing Agent Natallie Liz Island Welcome Real Estate LLC

1 Blue Water Dr, Saddlebunch, FL 33040

/61
Est $1,771,498

Not Listed For Sale

17153 Buttonwood Dr W, Summerland Key, FL 33042
- 3 Beds
- 2 Baths
- 1,426 Sq Ft
- Built 1998
17153 Buttonwood Dr W, Summerland Key, FL 33042

Last Sold Summary
- 30 Days On Market
Last Listing Agent Rhonda Williams 2150

/24
$1,595,000
- 3 Beds
- 3 Baths
- 3,000 Sq Ft
182 Venetian Way, Summerland Key, FL 33042

Experience classic Florida Keys waterfront living in this spacious canal-front retreat on Sugarloaf Key, offering boating access, expansive indoor-outdoor living, and just a short drive to Key West. 3,000 square feet of finished living space including 4 bedrooms and 3 baths. Situated on a wide canal with ample room for a future dock, offering the opportunity to create your own boating paradise.

James Olive LoKation Real Estate

182 Venetian Way, Summerland Key, FL 33042
/62
$2,400,000

Sold Aug 28, 2026

16843 E Point Dr, Summerland Key, FL 33042
- 3 Beds
- 2 Baths
- 2,224 Sq Ft
- Built 2001
Last Sold Summary
- 8% Below List Price
- $1,079/SF
- 148 Days On Market
Current Estimated Value $2,451,728

Last Listing Agent Suzanne Moore Suzanne Moore Real Estate

16843 E Point Dr, Summerland Key, FL 33042

/43
Est $1,108,897

Not Listed For Sale

17055 Kingfish Ln W, Summerland Key, FL 33042
- 2 Beds
- 2 Baths
- 1,184 Sq Ft
- Built 1988
17055 Kingfish Ln W, Summerland Key, FL 33042

Last Sold Summary
- 38 Days On Market
Last Listing Agent Team Kaufelt Truman & Co. (KW)

Showing Results 41 - 80, Page 2 of 18

Florida Monroe County

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Sugarloaf Key, FL Homes

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