Summerland Key, FL Homes for Sale

/45
$1,775,000
- 3 Beds
- 2 Baths
- 1,460 Sq Ft
31253 Hibiscus Dr, Big Pine Key, FL 33043

Experience the quintessential Florida Keys waterfront lifestyle from this open-water, 3-bedroom, 2-bathroom concrete home nestled along Big Pine Key's scenic Bogie Channel. This property boasts exceptional boating amenities, including two dedicated boat lifts and a convenient boat basin, ensuring effortless access to your vessels. Enjoy swift journeys, reaching the Atlantic in just two minutes or

Lara Hanousek Platinum Purpose Real Estate, LLC

31253 Hibiscus Dr, Big Pine Key, FL 33043
/57
$1,900,000
- 4 Beds
- 3 Baths
- 1,964 Sq Ft
27385 Saint Lucie Ln, Summerland Key, FL 33042

Tropical Keys Oasis -- Waterfront Luxury LivingCome experience this one-of-a-kind tropical oasis that feels like living at a Keys resort. Surrounded by lush landscaping, vibrant grass is the backdrop for nine coconut palms, five banana trees, two mango trees, and an avocado tree, this property bursts with natural beauty. Vibrant bougainvillea archways create a stunning entry to one of the most

Amedeo Belmonte William Raveis Florida LLC

27385 Saint Lucie Ln, Summerland Key, FL 33042
/35
$1,199,000
- 2 Beds
- 2 Baths
- 1,024 Sq Ft
29662 Independence Ave, Big Pine Key, FL 33043

Embrace the serene beauty of island living with this delightful 2-bedroom, 2-bathroom home nestled on a double-fenced lot in Big Pine Key. Perfectly positioned along a scenic canal, this property offers Southern charm, with an inviting wraparound porch to enjoy the gentle breeze and picturesque views. This home is ideal for both relaxation and entertaining.Step outside to a seawall that leads

Halley Haack Coldwell Banker Schmitt RE Co.

29662 Independence Ave, Big Pine Key, FL 33043
/21
$459,000
- 1 Bed
- 1 Bath
- 668 Sq Ft
701 Spanish Main Dr Unit 246, Cudjoe Key, FL 33042

Ocean-View Retreat in Gated Waterfront Community on Cudjoe Key!NIGHTLY RENTALS ALLOWEDWelcome to your slice of paradise in the heart of the Florida Keys. This well-maintained 1-bedroom, 1-bathroom waterfront home is located inside the highly desirable, gated community of Venture Out, offering ocean views, direct boating access, and a plethora of amenities just steps away.The home features

Lanny Gardner Bluescape Real Estate

701 Spanish Main Dr Unit 246, Cudjoe Key, FL 33042
/26
$1,595,000
- 3 Beds
- 3 Baths
- 2,022 Sq Ft
887 Bay Dr, Summerland Key, FL 33042

This 3-bedroom, 3-bath concrete fortress on a deep water canal (5' draft) is located in the highly sought-after Summerland Cove with quick access to both the Gulf and Atlantic--just a 15-minute boat ride to open ocean--this home is a true boater's paradise. Additionally, enjoy Airstrip rights as part of the Summerland Airport community. Set on a generous 75' x 100' corner lot, the property offers

Amy Hanson Realty Executives Florida Keys Summerland Branch

887 Bay Dr, Summerland Key, FL 33042
/11
$650,000
- Land
775 Pirates Rd, Summerland Key, FL 33042

Rare opportunity in Jolly Roger Estates on Little Torch Key. This 6,000 sq. ft. cleared and build-ready lot comes with two ROGO exemptions, allowing for immediate construction. The property features 60 feet of east-facing waterfront with a concrete dock, step-down, and davits already in place. Central sewer is connected. Located on a clean, deep canal (approx. 3 ft. control depth) with quick open

Melissa Gibbins Expert Realty LLC (HQ)

775 Pirates Rd, Summerland Key, FL 33042
/38
$999,000
- 3 Beds
- 2 Baths
- 1,144 Sq Ft
288 Spanish Main Dr, Summerland Key, FL 33042

Beautifully renovated canalfront home on Cudjoe Key offering the perfect blend of modern upgrades and classic Florida Keys charm. This 3-bedroom, 2-bath stilted home has been completely updated for serene, worry-free living.Inside, you'll find a beautiful kitchen with stainless steel appliances and quartz countertops, along with a comfortable living area. Step outside to enjoy spacious covered

Richard Haskins Buy The Keys

288 Spanish Main Dr, Summerland Key, FL 33042
/71
$1,094,900
- 3 Beds
- 2 Baths
- 1,272 Sq Ft
19881 Date Palm Dr, Summerland Key, FL 33042

Escape to your own private paradise at 19881 Date Palm Drive in Sugarloaf Key! This beautifully updated single-family home is tucked away in a quiet, secluded location and offers 100 feet of pristine canal frontage with a cut-in boat slip--perfect for boating enthusiasts with no neighbors across the canal!Step inside to find rich Brazilian hardwood floors, custom wood cabinetry, and sleek

Jimmy Lane Island Life Realty Experts

19881 Date Palm Dr, Summerland Key, FL 33042
/26
$899,000
- Land
- 5 Acres
- $179,800 per Acre
2231 Middle Torch Rd, Summerland Key, FL 33042

Opportunities like this are few and far between. This extraordinary offering includes two adjoining 2.5-acre parcels, totaling 5 acres of land -- Truly a rare find in the Florida Keys. Each lot measures 110 x 990 feet, offering an abundance of space, privacy, and potential. The property currently features two dwellings -- a single-family residence and a manufactured dwelling on the other -- each

Stephany Duvall Engel & Volkers Marathon

2231 Middle Torch Rd, Summerland Key, FL 33042
/42
$750,000
- 3 Beds
- 1.5 Baths
- 1,008 Sq Ft
31033 Hibiscus Dr, Big Pine Key, FL 33043

Nestled in the heart of Big Pine Key, this charming A-frame home offers classic Florida Keys character on an oversized DOUBLE LOT with canal frontage and excellent boating access to Bogie Channel. Built in 1973 and constructed with metal beams, this just-over-1,000-square-foot home blends durability with coastal charm. Additional highlights include an on-demand hot water heater, a seawall, and

Karen Haack Coldwell Banker Schmitt RE Co.

31033 Hibiscus Dr, Big Pine Key, FL 33043
/49
$1,550,000
- 3 Beds
- 2 Baths
- 1,396 Sq Ft
29635 Saratoga Ave, Big Pine Key, FL 33043

Welcome to your slice of island paradise in Pine Channel Estates in Big Pine Key! This beautifully built 3bedroom, 2bath CBS home offers the perfect blend of durability, comfort, and laid-back Keys living. Constructed with poured concrete floors and designed for peace of mind, the home features a tiled interior, a tiled roof, and convenient accordion shutters throughout. Step outside and embrace

Karen Haack Coldwell Banker Schmitt RE Co.

29635 Saratoga Ave, Big Pine Key, FL 33043
/7
$4,375,000 New Construction
- 5 Beds
- 5.5 Baths
- 3,119 Sq Ft
231 E Shore Dr Unit 6, Summerland Key, FL 33042

Introducing Seven Palms Cove, a one-of-a-kind new construction community redefining luxury island living in the Florida Keys. With only seven exclusive oceanfront residences starting at $4M, this private, gated enclave offers an extraordinary opportunity to own a slice of paradise just minutes from Key West.Each home spans over 4,000 sq. ft. with 5 bedrooms, 5.5 bathrooms, and open-concept

Stephanie Marinucci Serhant Florida LLC - Delray Beach Office

231 E Shore Dr Unit 6, Summerland Key, FL 33042
/18
$3,999,999
- 5 Beds
- 5 Baths
- 3,700 Sq Ft
17229 Oleander Ln, Summerland Key, FL 33042

Modern luxury seamlessly blends with relaxed tropical living in this oversized, brand-new construction home located on Sugarloaf Key. This elevated three-story residence features 5 bedrooms and 5 bathrooms all en suite, offering approximately 3,700 square feet of thoughtfully designed living space on a 10,000-square-foot lot. Designed with both lifestyle and functionality in mind, the home

Justyn Ewald Expert Realty LLC (HQ)

17229 Oleander Ln, Summerland Key, FL 33042
/72
$595,000
- 2 Beds
- 2 Baths
- 816 Sq Ft
701 Spanish Main Dr Unit 604, Cudjoe Key, FL 33042

Owner says ''Bring All Offers''Charming Coastal Retreat: 2 Bedroom, 2 Bath home with 35' concrete seawall. Nightly Rentals allowed.Welcome to your perfect getaway or investment opportunity! This delightful home built in 1993, offers 816 sq. ft. of comfortable living space, fully furnished and turn-key, making it an ideal choice for both relaxation and income generation. Step inside to discover a

Lanny Gardner Bluescape Real Estate

701 Spanish Main Dr Unit 604, Cudjoe Key, FL 33042
/46
$695,000
- 2 Beds
- 2 Baths
- 1,056 Sq Ft
29172 Rose Dr, Big Pine Key, FL 33043

Remodeled waterfront home! Located in a lovely neighborhood with a boat ramp right around the corner! Exterior of property has open parking as well as covered parking for multiple vehicles. Below home is surrounded by lattice to give additional shade and privacy. So much potential downstairs for outdoor entertainment.The main living area has gone through a full renovation. Kitchen boast sleek

Deni Heintzelman Keyisle Realty

29172 Rose Dr, Big Pine Key, FL 33043
/69
$2,195,000
- 5 Beds
- 3 Baths
- 1,903 Sq Ft
125 Colson Dr, Summerland Key, FL 33042

TRANSIENT LICENSE FOR NIGHTLY RENTALS BRINGING IN 250k+! WITH OPEN WATER VIEWS! ALMOST 2 ACRES TOTAL WITH 4 LOTS! THIS PROPERTY IS A ONE OF A KIND! A TRUE ''UNICORN!'' Turnkey Vacation Rental with 4 bedrooms and 2 baths in Main House which is a charming and OLD FLORIDA KEYS STYLE PROPERTY! Privacy, lush vegetation, stunning Open water views from the balconies from almost every room! Original

Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

125 Colson Dr, Summerland Key, FL 33042
/73
$1,099,000
- 5 Beds
- 2 Baths
- 1,888 Sq Ft
3836 No Name Rd, Big Pine Key, FL 33043

Introducing No Name Retreat - Rare waterfront opportunity with exceptional development potential featuring 140 feet of direct water frontage and expansive 14,420 sq ft lot. The property currently includes a full duplex plus an additional buildable vacant lot, offering endless possibilities for investors, builders, or someone looking for extra room next door. Live on the water while generating

Saara Staten Engel & Volkers Marathon

3836 No Name Rd, Big Pine Key, FL 33043
/2
$79,000
- Land
Lot 7 Hibiscus St, Big Pine Key, FL 33043

One of the cheapest waterfront lots in the Keys with great boating access directly from your property. Located in the beautiful nature preserve area of Big Pine Key, where nature and water actives are paramount. This lot is only 10 houses away from the open water, just minutes to our famous blue waters, fishing, diving and water actives that the Florida Keys are famous for. Many possibilities

Pamela Stangler Expert Realty LLC

Lot 7 Hibiscus St, Big Pine Key, FL 33043
/3
$64,750
- Land
0 Lot 21 Aloha Dr, Little Torch Key, FL 33042

ROGO Lot. Letter on hand from Monroe County granting 2 points

Jenna Stauffer Ocean Sotheby's International Realty

0 Lot 21 Aloha Dr, Little Torch Key, FL 33042
/2
$299,000
- Land
28168 Julia Ave, Little Torch Key, FL 33042

ROGO EXEMPT LOT! Build Now, No Waiting, Water Meter On Site, 6000 SF, Boat Ramp Within Walking Distance, Live The Dream. Single family home next door going on the market soon, buy both!

Doug Addeo Regional Trust Corporation

28168 Julia Ave, Little Torch Key, FL 33042
/40
$790,000
- 3 Beds
- 2 Baths
- 1,560 Sq Ft
22920 Privateer Dr, Summerland Key, FL 33042

Unlock Instant Equity on this Waterfront Gem waiting for restoration! Rare opportunity to own a waterfront escape at an unbeatable price point. This diamond in the rough is priced strictly for its condition, allowing you to build custom equity from day one. With a solid foundation and a backyard leading straight to the water's edge, this is the ultimate project for a savvy investor or visionary

Jeff Shapiro Global Luxury Realty LLC

22920 Privateer Dr, Summerland Key, FL 33042
/45
$519,000
- 2 Beds
- 2 Baths
- 758 Sq Ft
701 Spanish Main Dr Unit 417, Cudjoe Key, FL 33042

MOTIVATED SELLER! Turn-key 2BR/2BA waterfront fully furnished home with 35' concrete dock and patio furniture included, Front door paver patio, impact slider doors and windows, gas stove, and ample storage including outdoor dock box. Enjoy direct, deep-water access to the Ocean & Gulf, perfect for boating, fishing, and breathtaking sunrises & sunsets. Located in Venture Out, a gated, golf

Amanda Taylor Bluescape Real Estate

701 Spanish Main Dr Unit 417, Cudjoe Key, FL 33042
/31
$925,000
- 2 Beds
- 2 Baths
- 1,291 Sq Ft
31364 Avenue J, Big Pine Key, FL 33043

Open Waterfront Double Lot with Protected Boating and Endless PossibilitiesDiscover the best of Florida Keys waterfront living on this spacious double lot located on a quiet street on the open water with 150 feet of protective canal frontage with seawall, this property offers direct boating access to both the backcountry and the Atlantic Ocean and is only one lot in from the mouth of the canal

Tara Thoman-Wood,P.A. Berkshire Hathaway HomeServices Knight & Gardner Realty

31364 Avenue J, Big Pine Key, FL 33043
/4
$675,000
- Land
- 0.31 Acre
- $2,177,419 per Acre
2080 Coral Way, Big Pine Key, FL 33043

Rare opportunity to own a stunning ocean view double lot with 107 feet of canal frontage in sought-after Big Pine Key! Currently #5 in ROGO, this prime property comes with approved building plans—available upon request. The spacious lot offers ample room for your dream home with direct canal access and breathtaking open-water views. Buyers may have the ability to modify the existing plans—please

Kelly Acosta ARGO GROUP PROPERTIES LLC

2080 Coral Way, Big Pine Key, FL 33043
/53
$2,375,000
- 5 Beds
- 4 Baths
- 2,772 Sq Ft
205 S Point Dr, Summerland Key, FL 33042

Experience elevated waterfront living at this stunning South Point Sugarloaf Key retreat, where open-water serenity meets refined island design. This exceptional five-bedroom, four-bathroom residence is thoughtfully designed to host family and guests with ease, featuring a desirable split-floor plan and expansive living spaces framed by endless turquoise views.The primary suite is a private

Dawn McComish Lokation Real Estate

205 S Point Dr, Summerland Key, FL 33042
/41
$899,000
- 2 Beds
- 2 Baths
- 1,277 Sq Ft
29544 Independence Ave, Big Pine Key, FL 33043

Location, Location, Location and Price is The Key to this updated charming, coastal retreat. Featuring 75' canal-frontage, fully furnished, 2 bedrooms, 2 full baths plus an all-season sunroom. Generous and impressive living space is perfect for entertaining and family gatherings. Grab a siesta or your favorite beverage while overlooking the canal from the sunroom or on the covered patio. Pine

Jennifer Sylvia Keller Williams Key West Compass Realty

29544 Independence Ave, Big Pine Key, FL 33043
/94
$3,500,000
- 5 Beds
- 4 Baths
- 3,060 Sq Ft
17249 Bonefish Ln E, Sugarloaf Key, FL 33042

Experience the ultimate island lifestyle in this breathtaking waterfront residence located in the prestigious Sugarloaf Shores subdivision. Situated on a massive 25,482 sq. ft. lot, this property offers rare privacy with plenty of room to breathe.Built with solid CBS construction, this 5-bedroom, 4-bath home is designed to capture the beauty of its surroundings. The open living space and

Daniel Urban Expert Realty LLC (HQ)

17249 Bonefish Ln E, Sugarloaf Key, FL 33042
/71
$2,069,000
- 3 Beds
- 2 Baths
- 1,849 Sq Ft
1733 Sunrise Dr, Big Pine Key, FL 33043

Beautiful Waterfront Ocean & Canal property 3BD/2BA concrete block (CBS) direct ocean and canal access Property sits at 10 ft. elevation lot and features a durable aluminum roof, impact-resistant windows, and low-maintenance construction built for longevity in the Florida Keys. A 75 ft concrete dock, ideal for larger vessels, water toys, and fishing trips straight to open water. Spacious outdoor

Norman De la Cruz Florida Realty of Miami Corp

1733 Sunrise Dr, Big Pine Key, FL 33043
/7
$4,375,000 New Construction
- 5 Beds
- 5.5 Baths
- 3,119 Sq Ft
231 E Shore Dr Unit 4, Summerland Key, FL 33042

Introducing Seven Palms Cove, a one-of-a-kind new construction community redefining luxury island living in the Florida Keys. With only seven exclusive oceanfront residences starting at $4M, this private, gated enclave offers an extraordinary opportunity to own a slice of paradise just minutes from Key West.Each home spans over 4,000 sq. ft. with 5 bedrooms, 5.5 bathrooms, and open-concept

Stephanie Marinucci Serhant Florida LLC - Delray Beach Office

231 E Shore Dr Unit 4, Summerland Key, FL 33042
/47
$1,200,000
- 2 Beds
- 1.5 Baths
- 1,040 Sq Ft
637 Caribbean Dr E, Summerland Key, FL 33042

Elevated COASTAL LIVING meets clean, modern design in this beautifully remodeled 2BD/2BA stilted home in sought-after Summerland Key. Designed with a striking monochromatic palette, the interiors feel fresh, cohesive, and effortlessly sophisticated--ready for you to start living the Keys lifestyle.Step outside to a relaxing porch overlooking a 60' wide, crystal-clear flow-through canal--perfect

Donna Pezzi Keller Williams Key West Compass Realty

637 Caribbean Dr E, Summerland Key, FL 33042
/4
$179,000
- Land
0 Park Dr Unit Bk 3 Lt 7, Summerland Key, FL 33042

Exceptional corner lot opportunity in a sought-after Florida Keys neighborhood with a private airstrip. This Tier III parcel offers added flexibility in design and access, making it an ideal site for a custom home or strategic investment.PositPrime opportunity to build in one of the Florida Keys' most unique and desirable neighborhoods featuring a private airstrip. This Tier III vacant lot offers

Natallie Liz Expert Realty LLC (HQ)

0 Park Dr Unit Bk 3 Lt 7, Summerland Key, FL 33042
/19
$850,000
- 2 Beds
- 2 Baths
- 1,040 Sq Ft
3922 Gordon Rd, Big Pine Key, FL 33043

Not every canal-front home in the Keys feels like a destination. This one does. 3922 Gordon Road is an elevated 2BR/2BA waterfront retreat in Big Pine Key offering the lifestyle buyers come here for--easy boating, inviting outdoor living, and a home that feels like an escape from the moment you arrive. Bright coastal interiors, an open living/dining/kitchen layout, and a screened porch create a

Dominic Paolillo Jr. Truman & Co. (KW)

3922 Gordon Rd, Big Pine Key, FL 33043
/64
$1,900,000
- 3 Beds
- 2 Baths
- 1,841 Sq Ft
3127 Stewart Rd, Summerland Key, FL 33042

Gorgeous Open Water home that has been beautifully remodeled on 1.65 Acres of private land with handicap accessibilty! Complete remodel done, including the concrete pilings completed by a licensed contractor. Huge downstairs enclosure with a 2-car garage, this is an incredible opportunity to own a piece of nature in the Florida Keys! Privacy abounds on 1.65 acres of beautifully preserved, natural

Pamela Stangler Expert Realty LLC

3127 Stewart Rd, Summerland Key, FL 33042
/3
$300,000
- Land
0 Candice Ave, Little Torch Key, FL 33042

Rare opportunity to acquire a 6-parcel assemblage totaling approx. 13.67 acres on Little Torch Key. Includes five 6,000 sq. ft. Mates Beach lots on Candice Avenue (two Tier 3 Infill) and a 12.97+/- acre tract with 2.61 acres upland and 10.36 acres environmentally sensitive land. Perfect for agricultural or beekeeping use, conservation project, or long-term investment. Located in a desirable Lower

Claude Gardner Berkshire Hathaway HomeServices Knight & Gardner Realty

0 Candice Ave, Little Torch Key, FL 33042
/4
$2,499,000
- 3 Beds
- 1 Bath
- 1,020 Sq Ft
32029 Marginella Dr, Big Pine Key, FL 33043

Rare Waterfront Property on No Name Key: Your Gateway to Natural Florida Keys Living. Are you seeking privacy, breathtaking open water views, and exclusive boat dockage? Look no further than this exceptional offering nestled in the heart of the Natural Florida Keys. Situated on the private and secluded No Name Key, just a stone's throw away from Big Pine Key, this nearly 2-acre property presents

Tara Thoman-Wood,P.A. Berkshire Hathaway HomeServices Knight & Gardner Realty

32029 Marginella Dr, Big Pine Key, FL 33043
/24
$269,999 New Construction
- 1 Bed
- 1 Bath
- 312 Sq Ft
29859 Overseas Hwy Unit 37, Big Pine Key, FL 33043

Welcome to easy island living in this 2021 Skyline Park Model Home located in the desirable Breeze Pines RV Estate. Thoughtfully designed, this 1-bedroom, 1-bath residence with a loft offers comfort, style, and functionality in a welcoming community setting. The home comes fully furnished and features a cozy fireplace, three mini-split A/C units for efficient climate control, and a well-equipped

Halley Haack Coldwell Banker Schmitt RE Co.

29859 Overseas Hwy Unit 37, Big Pine Key, FL 33043
/94
$3,675,000
- 4 Beds
- 4 Baths
- 2,766 Sq Ft
414 Caribbean Dr E, Summerland Key, FL 33042

Discover the Ultimate in Luxury Waterfront Living at This Prime Oceanfront Tropical Gem in Summerland Key.Located in the prestigious community of Summerland Cove--just 30 minutes from Key West--this exceptional deep-water oceanfront estate offers the perfect blend of privacy, beauty, and unparalleled boating access.Completely rebuilt in 2006, this elevated 4BR/3.5BA residence spans 2,766 sq. ft.

Lisa Swanson The Agency Florida Keys

414 Caribbean Dr E, Summerland Key, FL 33042
/31
$1,055,000
- 3 Beds
- 2 Baths
- 1,225 Sq Ft
83 Sugarloaf Dr, Summerland Key, FL 33042

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 fourth (4) bedroom, office, hobby room, etc.. Features a swimming pool with full screened outdoor patio surround, and lush tropical landscaping with palms, orchids, agave, and mature mango trees. Two cistern tanks for watering plants,

Dave Wiley Coldwell Banker Schmitt Real Estate Co. (KW)

83 Sugarloaf Dr, Summerland Key, FL 33042
/4
$100,000
- 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
/47
$1,200,000
- 3 Beds
- 2 Baths
- 1,250 Sq Ft
43 Venetian Way, Summerland Key, FL 33042

Beautifully updated 3 bedroom 2 bath home, with effective build date of 2015 and completely renovated in 2018 including New Electrical, Plumbing, HVAC, Roof, Tankless Water heater, Flooring, Kitchen, Bathrooms, Windows, & Doors, landscaping/sprinkler system, TESLA charging station and an amazing new paved driveway installed in 2021. This is a split floor plan for privacy with amazing screened in

Lori Cameron Buy The Keys

43 Venetian Way, Summerland Key, FL 33042

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