Summerland Key, FL Homes

/85
$5,999,000
- 4 Beds
- 4 Baths
- 4,315 Sq Ft
4500 Filer Cove Rd, Summerland Key, FL 33042

Picture perfect Sunset Views over the open water at this 12-Acre waterfront compound located on Big Torch Key, a coastal community of large private estates located just 30 minutes outside of Key West. Driving down the gated 300' scenic driveway balmy breezes and tropical landscape lead you to the 4,315 sq. ft. open water residence. Once here you will enjoy world-class fishing and diving just

Lisa Ferringo

Coldwell Banker Schmitt Lower Keys (KW)

(786) 998-2623

4500 Filer Cove Rd, Summerland Key, FL 33042
Selling your home? Sell it faster and for more with a Homes.com Boost.
Learn More
/20

$3,950 - $4,200 per month

Little Torch Cottages

2 Beds

28501 Channel View Dr, Little Torch Key, FL 33042

In Little Torch Key, near Mile Marker 28 on US Highway 1, Little Torch Cottages features 48 homes for those looking for something special. This beautiful property has 400 feet of open water views on Pine Channel, and also offers 22 foot boat slips at a discounted monthly rate for community residents. You will also be able to enjoy a community Clubhouse, park, BBQ areas, Paddle Board and Kayak

28501 Channel View Dr, Little Torch Key, FL 33042
/13
$24,500 Sold Jul 02, 2025
- Land
- 198 Days On Market
LOT 8 Little Knockemdown Key Unit AKA Parcel 23, Summerland Key, FL 33042

Adventure offshore island 4 acre lot in the heart of the Great White Heron Wildlife refuge is suitable for temporary camping and exploration. World class flats fishing for bonefish, tarpon, permit and redfish nearby. Located on South West end of Little Knockemdown Key. Accessible by kayak, paddle board and shallow draft vessels. Privacy and nature are the norm out here on Little Knockemdown Key

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

LOT 8 Little Knockemdown Key Unit AKA Parcel 23, Summerland Key, FL 33042

/63
Est $1,937,068 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,366 Sq Ft
17057 Bonita Ln W, Sugarloaf Key, FL 33042

17057 Bonita Ln W, Sugarloaf Key, FL 33042

/30
$975,000
- 3 Beds
- 3 Baths
- 1,492 Sq Ft
31490 Avenue F, Big Pine Key, FL 33043

This all-concrete, meticulously designed 3-bedroom, 2.5-bath home offers both luxury and functionality. Featuring impact windows and doors and a durable metal roof, this home provides peace of mind and protection for years to come. The open-concept living area is perfect for both relaxation and entertaining, with a modern kitchen boasting quartz countertops and stainless steel appliances. The

Coby Taylor

Expert Realty LLC (HQ)

(833) 691-1620

31490 Avenue F, Big Pine Key, FL 33043
/36
$5,000 per month
- 3 Beds
- 1 Bath
- 1,116 Sq Ft
- House for Rent
27316 Cayman Ln Unit 1, Summerland Key, FL 33042

Presenting Villa Marquesa — the perfect opportunity to lease a charming private villa in the heart of Ramrod Key, located in the picturesque Lower Keys. This fully furnished 3-bedroom, 1-bath tropical retreat offers stylish South Florida beach decor, a fully equipped kitchen, and two spacious living areas for ultimate comfort. Ideal for tenants seeking privacy, relaxation, and a resort-style

Gilbert Garcia Proxy Realty Group LLC

27316 Cayman Ln Unit 1, Summerland Key, FL 33042
/40
$900,000 Sold Jul 01, 2025
- 992 Sq Ft
- $907/SF
- 137 Days On Market
- 2 Beds
- 2 Baths
- Built 1983
1342 Ocean Dr, Summerland Key, FL 33042

Renovated Waterfront Gem! Welcome to your dream coastal retreat! This beautifully updated 2-bedroom, 2-bath home offers a 60-ft concrete dock along a 60-ft wide canal, providing the perfect setup for all your boating and water adventures. The property includes covered parking and a garage, ensuring convenience and plenty of storage for your vehicles and gear.Step inside to a bright and inviting

Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

1342 Ocean Dr, Summerland Key, FL 33042

/9
Not Listed For Sale
Lot 8 Overseas Hwy, Summerland Key, FL 33042

Lot 8 Overseas Hwy, Summerland Key, FL 33042

/28
$980,000
- 4 Beds
- 3 Baths
- 1,457 Sq Ft
31441 Avenue F, Big Pine Key, FL 33043

This solid all-concrete home, situated on a generous 10,000 sq ft double lot, offers the perfect blend of comfort and style for a growing family. Step into the open-concept living area with vaulted ceilings, creating an airy, welcoming atmosphere. The chef-inspired kitchen features beautiful quartz countertops and stainless steel appliances, perfect for cooking and entertaining. Tile floors

Coby Taylor

Expert Realty LLC (HQ)

(844) 559-1544

31441 Avenue F, Big Pine Key, FL 33043
/13
$2,400 per month
- 1 Bed
- 1 Bath
- 528 Sq Ft
- House for Rent
31020 Avenue B, Big Pine Key, FL 33043

Property Id: 2011041Cozy 1 Bedroom, 1 Bath Mobile HomeThis well-maintained mobile home features laminate flooring, a screened-in back porch, and a small fenced side and backyard. It includes washer/dryer hookups and an on-demand water heater. The home is unfurnished, and utilities are not included.Lease Terms:Maximum 2 people $2,400.00/ per month

31020 Avenue B, Big Pine Key, FL 33043
/41
$650,000 Sold Jul 01, 2025
- 1,120 Sq Ft
- $580/SF
- 81 Days On Market
- 2 Beds
- 2 Baths
- Built 1984
22882 Buccaneer Ln, Summerland Key, FL 33042

Coastal Paradise: 2-Bedroom, 2-Bath Canal-Front Home with Direct Ocean AccessThis stunning 2-bedroom, 2-bath home offers the ultimate canal-front lifestyle, minutes from open water with no bridges to navigate, perfect for boating enthusiasts. Located on the coveted Oceanside, the property features a spacious 60-foot dock ready for your vessel, offering convenient and quick access to the

Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

22882 Buccaneer Ln, Summerland Key, FL 33042

/2
Not Listed For Sale
0000 Watson Blvd, Big Pine Key, FL 33043

0000 Watson Blvd, Big Pine Key, FL 33043

/36
$1,189,000
- 4 Beds
- 3 Baths
- 1,896 Sq Ft
31569 Avenue D, Big Pine Key, FL 33043

Welcome to your Florida Keys fortress! This newly constructed 4-bedroom, 3-bath concrete home offers unmatched durability, modern finishes, and gorgeous open water views from porches on both levels. Just a few hundred feet from deep water boating, this property provides the closest boat access to the world-famous Bahia Honda Bridge of any neighborhood in the Lower Keys, navigating to the ocean or

Coby Taylor

Expert Realty LLC (HQ)

(855) 699-7204

31569 Avenue D, Big Pine Key, FL 33043
/65
$10,995 per month
- 4 Beds
- 3 Baths
- 3,116 Sq Ft
- House for Rent
30825 Ortega Ln, Big Pine Key, FL 33043

Welcome to your slice of paradise in Big Pine Key! This stunning property offers peace and privacy on a quiet street,just minutes from world class fishing, boating, and the natural beauty of Bahia Honda State Park. This charminghome comes fully furnished and features an open-concept layout, modern updates, and coastal finishes throughout. relax on the coveredporch, entertain on the spacious deck,

Walter Vargas Cervera Real Estate Inc.

30825 Ortega Ln, Big Pine Key, FL 33043
/44
$650,000 Sold Jun 30, 2025
- 828 Sq Ft
- $785/SF
- 8 Days On Market
- 2 Beds
- 2 Baths
- Built 2002
701 Spanish Main Dr Unit 390, Cudjoe Key, FL 33042

Turnkey Waterfront Vacation Rental with Ocean Views in Venture Out.Welcome to your Florida Keys escape--a fully furnished, income-producing 2-bedroom, 2-bath home ideally positioned on a wide canal with stunning ocean views and 35 feet of concrete seawall dockage. Located in the vibrant, gated community of Venture Out on Cudjoe Key, this well-maintained property is not just a serene coastal

Kelly Gardner Bluescape Real Estate

701 Spanish Main Dr Unit 390, Cudjoe Key, FL 33042

/5
Est $1,327,282 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,881 Sq Ft
354 Airport Dr S, Summerland Key, FL 33042

354 Airport Dr S, Summerland Key, FL 33042

/34
$1,789,000
- 4 Beds
- 3 Baths
- 2,323 Sq Ft
31450 Avenue G, Big Pine Key, FL 33043

This expansive 4 bedroom, 3 bathroom home offers over 2,300 sq ft of solid concrete construction, built in 2023 with hurricane impact windows/doors and a metal roof for total peace of mind.Step inside to a bright, open-concept floor plan with sleek tile flooring throughout. Prepare your Keys Fresh Catch in your Chef's Kitchen with custom cabinets and quartz countertops. The massive master suite

Coby Taylor

Expert Realty LLC (HQ)

(866) 372-6249

31450 Avenue G, Big Pine Key, FL 33043
/13
$3,200 per month
- 3 Beds
- 2 Baths
- 1,528 Sq Ft
- House for Rent
31167 Ave G, Big Pine Key, FL 33043

Property Id: 1827061If your between homes, or construction, or here for a shorter period, here is a fully furnished home. Available now, 6mos + few days rental. Nice spacious, furnished home on a double lot, with fenced back yard. Utilities not included. Above ground pool. Close to local amenities. 3bd/2bth 1528 sq. ft. home with laundry room. Central AC & Heat. Monthly yard care

31167 Ave G, Big Pine Key, FL 33043
/22
$500,000 Sold Jun 30, 2025
- 988 Sq Ft
- $506/SF
- 41 Days On Market
- 3 Beds
- 1 Bath
- Built 1958
31232 Ave d, Big Pine Key, FL 33043

Whether you're looking for a place to call HOME or a GET AWAY to retreat to. Charming 3-bedroom home with open floor plan on a double lot 50 X 200 (10,000 sq. ft.) in Big Pine Key. Front lot is fenced, no neighbor on one side. Has a front covered porch. Back patio deck. Back lot has no neighbor on either side. Home is move in ready and can close quickly. New appliances in the home. Ductless ac.

Rose Dell Keller Williams Key West Compass Realty

31232 Ave d, Big Pine Key, FL 33043

/2
Est $293,208 Not Listed For Sale
- Studio
701 Spanish Main Dr Unit 40, Cudjoe Key, FL 33042

701 Spanish Main Dr Unit 40, Cudjoe Key, FL 33042

/43
$1,799,000
- 3 Beds
- 3 Baths
- 1,998 Sq Ft
17094 Coral Dr, Summerland Key, FL 33042

This beautifully appointed home is located in prestigious Sugarloaf Shores, an upscale coastal community of waterfront homes just 15 miles from the magic of Key West. As you enter the 3 Bedroom 2 Bath 2,000 sq. ft. home a massive Great Room greets you highlighted by a true chef's Kitchen offering lots of custom cabinetry, stainless appliances, 2 wine coolers and large center island for friends

Lisa Ferringo

Coldwell Banker Schmitt Lower Keys (KW)

(786) 244-7125

17094 Coral Dr, Summerland Key, FL 33042
/8
$4,500 per month
- 2 Beds
- 2 Baths
- 948 Sq Ft
- House for Rent
24317 Caribbean Dr W, Summerland Key, FL 33042

Welcome to Casa Caribe, a long-term rental, comfortable 2 bed, 2 bath vacation home on Summerland Key. Located on one of the best canals on the island, and conveniently across the canal from the Summerland Marina, this home provides quick boating to the blue water as well as the prime diving areas of the Gulf and Looe Key National Marine Sanctuary out front. Large boats will tie up easily at

Mary Conklin Action Keys Realty of the Lower FL Keys LLC

24317 Caribbean Dr W, Summerland Key, FL 33042
/26
$239,000 Sold Jun 30, 2025
- Land
- 74 Days On Market
701 Spanish Main Dr Unit 6, Cudjoe Key, FL 33042

Embrace the island lifestyle with this prime RV lot in Venture Out, a premier gated community on Cudjoe Key! Nestled in a quiet section of the park, this lot offers peak-a-boo ocean views and stunning sunsets from the rear of the property, making it the perfect tropical retreat. Whether you're looking for a personal getaway or a smart investment, this lot is a rare find--Venture Out is one of the

Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

701 Spanish Main Dr Unit 6, Cudjoe Key, FL 33042

/2
Est $576,763 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,232 Sq Ft
27188 Dolphin Rd, Ramrod Key, FL 33042

27188 Dolphin Rd, Ramrod Key, FL 33042

/51
$1,099,000
- 3 Beds
- 3 Baths
- 1,920 Sq Ft
22841 Buccaneer Ln, Summerland Key, FL 33042

Welcome to ''Cayo Casa Cudjoe,'' a tropical haven where the island lifestyle seamlessly blends with world-class fishing. Nestled on a beautifully landscaped triple lot, this waterfront gem offers the ultimate escape. The heart of this angler's paradise are the 2 covered boat slips, each equipped with their own lift; your gateway to the best fishing, diving and boating in the Florida Keys. Whether

Lisa Ferringo

Coldwell Banker Schmitt Lower Keys (KW)

(786) 244-8373

22841 Buccaneer Ln, Summerland Key, FL 33042
/21
$3,000 per month
- 3 Beds
- 2 Baths
- 741 Sq Ft
- Property for Rent
30925 Mercedes Rd, Big Pine Key, FL 33043

July Move-in rental ready manufactured home with new flooring, kitchen appliances, AC units, and tankless water heater. The lot has storage units and space to park your boat/trailer. Unit has 3 bedrooms and 2 bathrooms to accommodate a small family. Close vicinity to local parks and boat ramps at Bahia Honda. F/L/S Application & Background Check Required.

Paulette Thompson PA Ocean Sotheby's International

30925 Mercedes Rd, Big Pine Key, FL 33043
/13
$265,000 Sold Jun 30, 2025
- Land
- 103 Days On Market
31014 Avenue E, Big Pine Key, FL 33043

BUILD A NEW HOME, SKIP THE ROGO PROCESS! ROGO-exemption letter is in hand for this 10,000 sq. ft. double lot located on the corner of Sands Rd. and Avenue E. The undeveloped lots on the north side of Avenue E are state-owned; Monroe County owns multiple adjacent lots to the east. The convenient location is within walking and biking distance of the Big Pine Community Park where you'll find

Patti Nickless Coldwell Banker Schmitt RE Co. Lower Keys Office

31014 Avenue E, Big Pine Key, FL 33043

/14
Not Listed For Sale
12, 13, 14 Cook Island, Cook Island Key, FL 33043

12, 13, 14 Cook Island, Cook Island Key, FL 33043

/44
$718,000
- 2 Beds
- 1 Bath
- 1,497 Sq Ft
30416 Coconut Hwy, Big Pine Key, FL 33043

OVER ONE-HALF ACRE, lovingly cared for ... welcome to your sanctuary in the Keys! The large, fenced area of this 25,000 sq. ft. property provides wonderful privacy with a mature mango tree, starfruit tree, multiple banana plants, frangipanis, and ample space for planting a garden. Step inside the 1497 sq. ft. CBS home and you'll feel the old Keys charm mixed with the new. Your eyes are drawn to

Patti Nickless

Coldwell Banker Schmitt RE Co. Lower Keys Office

(866) 646-1176

30416 Coconut Hwy, Big Pine Key, FL 33043
/18
$3,600 per month
- 2 Beds
- 1 Bath
- 774 Sq Ft
- Property for Rent
Unlisted Address

Wonderful renovated waterfront 1/2 Duplex for rent! This one is the left side of duplex and has spacious 2 bedrooms and 1 full bath with open floor plan for living. Completely renovated and gorgeous inside! Beautiful Quartz countertops and stainless appliances in kitchen, all new fixtures and flooring thru-out. Stylish barn doors in both bedrooms with ample closet space. Screened in back porch

Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

Unlisted Address
/2
$52,000 Sold Jun 30, 2025
- Land
- 0.27 Acre
- $189,391 per Acre
- 218 Days On Market
State Road 4a _ Rogo Dedication Lot, Little Torch Key, FL 33042

Property has letter for the point determination from the County for 2 points. NOT ROGO EXEMPT LOT.

Sandra Dolowy KeyIsle Realty

State Road 4a _ Rogo Dedication Lot, Little Torch Key, FL 33042

/20
Est $670,062 Not Listed For Sale
- 1 Bed
- 1 Bath
- 552 Sq Ft
31342 Avenue I, Big Pine Key, FL 33043

31342 Avenue I, Big Pine Key, FL 33043

/43
$799,000
- 3 Beds
- 1 Bath
- 1,162 Sq Ft
10 W Cook, Cook Island Key, FL 33043

Welcome to Cook Island, a semi-private pristine barrier island accessible by boat only offering one of the most beautiful beaches in the Florida Keys. This self-sustaining beach-front property sprawls over 3/4 of an acre and features a 2 Bedroom main house plus a detached beach-front studio with sleeping loft that could fill the need for a 4th Bedroom. Enjoy balmy breezes and stunning starlit

Lisa Ferringo

Coldwell Banker Schmitt Lower Keys (KW)

(888) 366-9807

10 W Cook, Cook Island Key, FL 33043
/16
$7,500 per month
- 3 Beds
- 2 Baths
- 1,418 Sq Ft
- House for Rent
1540 Lantana Ln, Big Pine Key, FL 33043

FISHERMANS DREAM HOUSEBRING YOUR BOATS TO THIS AMAZING 3/2 HOUSE SECLUDED ON A CORNER LOT WITH 190FT. SEAWALL .BOAT RAMP BLOCKS AWAY.ENJOY THE POOL, COCKTAILS AT THE OUTSIDE BAR AND THE ADORABLE KEY DEER ROAMING THE NEIGHBORHOOD.ICE MAKER AT BAR. SLEEPS 8.MULTIPLE MONTHS AND OFF SEASON MONTHS OFFERED AT DISCOUNT RATES.$7500/mo for April-June

Andrea Lennon Vylla Home

1540 Lantana Ln, Big Pine Key, FL 33043
/42
$1,900,000 Sold Jun 29, 2025
- 1,702 Sq Ft
- $1116/SF
- 17 Days On Market
- 3 Beds
- 2 Baths
- Built 2011
20867 5th Ave W, Cudjoe Key, FL 33042

Enjoy deep draft dockage, 2 Boat Lifts, Garage and Pool plus no steps to climb at this 3 Bedroom 2 Bath home located in Cudjoe Gardens, an upscale waterfront community of CBS constructed Above Flood ground level homes offering a neighborhood full service marina and waterfront restaurant and bar. Enter into the open Great Room where a wall of impact glass doors overlooks the pool and water. The

Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

20867 5th Ave W, Cudjoe Key, FL 33042

/3
Not Listed For Sale
Vacant Lot Diane Rd, Big Pine Key, FL 33043

Vacant Lot Diane Rd, Big Pine Key, FL 33043

/36
$799,000
- 3 Beds
- 2 Baths
- 1,200 Sq Ft
1590 Gardenia Ln, Big Pine Key, FL 33043

Your Keys Getaway is Waiting on Big Pine Key!Tucked away in the peaceful Key Deer National Wildlife Refuge, this adorable canal-front home is ready for new owners to move right in and start living the island dream! Featuring 3 bedrooms, 2 baths, and an open living space with a freshly updated kitchen and new appliances, it's the perfect spot to relax or entertain.The third bedroom has a private

Sandra Tuttle

Island Welcome Real Estate

(877) 813-2468

1590 Gardenia Ln, Big Pine Key, FL 33043
/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 in Big Pine Key! This waterfront getaway is located in the National Key Deer Refuge, just 30 minutes away from Key West. This three-bedroom/two-bath home features an open floor plan, a fully furnished living area, and a modern, fully equipped kitchen. The kitchen is a culinary dream, featuring stainless steel appliances and an oversized quartz island, surrounded by eight

Mary Jo Selden DomainRealty.com LLC

3770 Park Ave, Big Pine Key, FL 33043
/44
$699,900 Sold Jun 27, 2025
- 1,232 Sq Ft
- $568/SF
- 97 Days On Market
- 2 Beds
- 2 Baths
- Built 1990
29853 Frostproof Rd, Big Pine Key, FL 33043

This quintessential home is surrounded by 17 parcels of pristine environmental and conservation land, offering nature, privacy, wildlife, and the best tropical living the Keys has to offer. The full-size screened rear porch faces vacant land with swaying palms, tropical vegetation, with key deer grazing below. Enjoy morning coffee or evening cocktails while tropical breezes provide refreshing

Donna Halstead Coldwell Banker Schmitt RE Co. Lower Keys Office

29853 Frostproof Rd, Big Pine Key, FL 33043

/34
Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,012 Sq Ft
27772 Astrangia Ave, Summerland Key, FL 33042

27772 Astrangia Ave, Summerland Key, FL 33042

Showing Results 1 - 40, Page 1 of 18

Florida Summerland Key

How to Buy a Home How to Finance a Home How to Sell a Home

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage