Homes on Sugarloaf Key are waterfront and non-waterfront which will explain the large range of asking prices. It is close enough to Key West for commuting purposes, yet maintains the "island" feel of the Florida Keys.
Active listings of homes for sale on Sugarloaf Key are shown below. If you are particularly interested in properties on this island, click to view the updated Market Report for Sugarloaf Key (coming soon). You will see all active listings, pending sales (if available), and home sales within the past year.
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Located at the end of a quiet street in Sugarloaf Key, this 2 bedroom, 2 bath canal-front home is only two lots in from open water and offers open water views from the li...
3 bed 2 bath stilt home built in 2018 in sought after Sugarloaf Key. Open concept floor plan, large kitchen with an abundance of large white cabinets, kitchen island over...
Just a short boat ride to popular Lower Keys sandbars, coral heads, and fishing grounds, this Sugarloaf Shores canal-front home is made for the buyer who wants boating, f...
On a quiet dead-end street in the highly sought-after Sugarloaf Shores community, sits this fully renovated tropical retreat thats reminiscent of something straight out o...
Morning Glory - The Dolphin House is one of those rare oceanfront sanctuaries where time softens, stress fades, and every sunrise feels like it was created just for you. ...
Recently updated canal-front home in highly desirable Upper Sugarloaf Key with direct boating access to the world famous Florida Keys back-country and Gulf of America. Lo...
Opportunities like this are hard to find in the Lower Keys--this fully renovated 3-bedroom, 2-bath home sits on a generous half-acre lot in the highly desirable Sugarloaf...
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. ...
Experience the best of waterfront living in this brand-new home on Lower Sugarloaf Key. Thoughtfully designed and meticulously built, this 3-bedroom, 2.5-bath residence o...
This beautifully remodeled waterfront bungalow is nestled in the heart of Sugarloaf Shores ,one of the Lower Florida Keys' most desirable boating communities. Set on an e...
A rare double-parcel waterfront opportunity in Lower Sugarloaf Key - offering a newly constructed home plus an adjacent buildable lot, creating the ultimate private boati...
Botanical Waterfront Compound ~ 3 bedroom/2 bath elevated CBS home on a fenced half-acre, just 20 minutes from Key West and near Sugarloaf schools. Potential for a fourt...
Welcome to your private waterfront retreat in the highly sought-after Southpoint neighborhood of Sugarloaf Key - where space, privacy and effortless access to the open wa...
Build your dream home. Imagine waking up to the natural beauty of the Florida Keys on this 44,431sqft lot. Great location near Sugarloaf school. Easy commute to Key West,...
Charming 2BR/2BA PLUS A LOFT, Keys home on Upper Sugarloaf, the perfect blend of comfort and waterfront living. Built on sturdy concrete pilings with Hardie board sidin...
Rare opportunity to acquire Sugarloaf Lodge & Marina - 10.6± Acre Waterfront Resort Redevelopment Opportunity Near Key West, located on Lower Sugarloaf Key, 15 minutes fr...
Experience elevated waterfront living at this stunning South Point Sugarloaf Key retreat, where open-water serenity meets refined island design. This exceptional five-bed...
Set on over an acre of land, 19267 Hansen Trail is a truly one-of-a-kind property where modern luxury meets refined homestead living. Offering nearly 2,000 square feet...
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 wa...
Renovated Commercial Space - The Alamo Building, Sugarloaf Key (MM 20) Prime, newly updated commercial space available on Sugarloaf Key, directly across from Mangrove Ma...
**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 privac...
Welcome to your slice of Lower Keys paradise--just 17 miles from Key West yet worlds away from the hustle. This elevated 2-bedroom, 2-bath home sits on a generous lot in ...
There are homes that check boxes, and then there are homes that speak to you the moment you step inside. This custom, meticulously crafted 3BR/3BA, 1,700 sq ft CBS master...
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 provid...
Stunning open water views from this fabulous waterfront home! A truly rare and highly coveted 37,139 sqft lot point lot with A massive 362 FT OF WATERFRONTAGE on prestig...
Now only $120,000. Best priced lot in popular Upper Sugarloaf Key and priced for immediate sale! Take advantage of this opportunity to develop this larger 150 x 100 T...
Welcome to the lowest priced waterfront lot with an active building permit on prestigious Sugarloaf Key. This oversized 14,706 sq. ft. canal-front property features no-br...
Masterpiece of Modern Strength & Luxury | Brand-New Concrete Waterfront Estate on Prestigious Sugarloaf Key! This extraordinary new construction stunner is engineered as...
OPEN WATER RESORT STYLE CONCRETE POOL home on sought after Southpoint, Sugarloaf Shores. This exceptional 4-bedroom, 3-bath concrete waterfront residence captures breatht...
Introducing Blue Water Lagoon Estate! Experience unmatched privacy and exceptional waterfront living at this gated 2.33-acre oceanfront estate in exclusive Sugarloaf Beac...
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 ...
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...
**Tier III Beautiful Buildable Canal Front Lot in Sugarloaf Shores!** Discover an exceptional opportunity in the prestigious Sugarloaf Shores neighborhood with this ov...
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 s...
Experience breathtaking sunsets over Sugarloaf Sound from this 2-story CBS open water estate offering 3 bedrooms, 2 baths, and 2,170 sq ft of elevated coastal living just...
Positioned on a rare west facing point lot with 270 ft of sparkling open water frontage on Sugarloaf Sound, this fully reimagined 3 Bedroom 3 Bathroom estate captures bre...

Jim Signor: 305-394-4449