Summerland Key FL Real Estate & Homes for Sale

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Beds:
2
Baths:
2.00
Sq.Ft.:
770
Status:
NEW LISTING
MLS#:
621327
Type:
Mobile Home
Subdivision:
Venture Out (23.0)
Lot size:
0.04 Acres
Year built:
1992
Courtesy: Berkshire Hathaway HomeServices Keys Real Estate 305-743-7636
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ADDITIONAL INFORMATION

YOUR FLORIDA KEYS ESCAPE AWAITS! Welcome to your own slice of paradise in the highly sought-after gated community of Venture Out on Cudjoe Key. This beautifully furnished 2-bedroom, 2-bath home combines water views, exceptional boating access, comfortable island living, and resort-style amenities just seconds from open water. Situated on a wide 60' canal, boaters will love the 35' concrete dockage with dock posts, cleats, swim ladder, and fish-cleaning table--perfect for days spent fishing, diving, cruising, or exploring the Keys. Inside, the bright and inviting living space opens onto a covered porch, creating the perfect place to relax after a day on the water. The home has been extensively updated, including a new kitchen in 2026, new flooring in 2022, A/C in 2020, and a new roof, siding, windows, doors, insulation, and hot water heater in 2019. A beautiful tongue-and-groove ceiling adds to the relaxed island feel. The primary suite features a king-size bed, ample storage, and private ensuite bath, while the guest bedroom offers a queen-size bed and access to the second full bath. Venture Out offers an incredible resort lifestyle with a heated pool, hot tub, marina, fuel dock, boat ramps, tennis, pickleball, bocce, basketball, playground, recreation hall, pavilion, 24-hour gated security, and more. Nightly rentals are permitted, and the home generated approximately $84,000 in gross rental revenue, providing an attractive added benefit when you're not enjoying it yourself. Seller financing may also be considered with acceptable terms. Beautifully furnished and ready to enjoy, this is your opportunity to experience the Florida Keys lifestyle from day one.

Beds:
4
Baths:
6.00
Sq.Ft.:
3,224
Status:
NEW LISTING
MLS#:
621324
Type:
Single Family
Subdivision:
Breezeswept Bch Est (27.5)
Lot size:
0.24 Acres
Year built:
1999
Courtesy: Internet Realty of the Florida Keys 305-745-9088
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ADDITIONAL INFORMATION

Spectacular sunset views from this custom-built, fully furnished 4-5 bedroom, 5½ bath oceanside home in beautiful Breeze Swept Beach Estates. Situated on an oversized 10,500 sq. ft. fenced lot, the property offers plenty of parking for boats, RV's, and jet skis. This custom home features 3,224 sq. ft. under air and an additional 1,276 sq. ft. of sunset and sunrise viewing decks, including a panoramic 360° view from the rooftop widow's walk. The expansive open-concept living, dining, and kitchen area features cathedral ceilings, creating a bright and inviting space. The updated kitchen boasts quartz countertops with a counter-to-ceiling quartz backsplash, stainless steel appliances including a gas range, and a whole-house maintenance-free Allini water purification system. Enjoy the custom indoor/outdoor sound system, 85' flat-screen TV, and private bathrooms in every bedroom. The office can easily be converted into a fifth bedroom, as it already includes its own full bath. Additional features include front and rear access stairs, covered porches overlooking the new custom pool with heater and chiller, PebbleTec pool finish, and a custom paver pool deck. The property is well-equipped for both comfort and boating with an elevated whole-house Kohler propane generator, garage, large storage area, custom rod racks, ice machine, outdoor shower, 9' x 60' concrete dock, 15,000 lb boat lift, shaded fish cleaning station, and an in-ground 1,000-gallon propane tank for all your propane needs. Other highlights include impact windows and doors, a fenced yard with multiple gates, covered parking, a covered outdoor bar and entertainment area, and a gas hookup for the BBQ grill. Enjoy direct deep-draft Atlantic Ocean access for the perfect day on the water. This stunning home is completely turnkey--just bring your T-shirts, shorts, and toothbrush and start enjoying the Keys lifestyle. Come see this exceptional property before it's gone. Easy and a pleasure

Beds:
2
Baths:
2.00
Sq.Ft.:
828
Status:
Active
MLS#:
621307
Type:
Mobile Home
Subdivision:
Venture Out (23.0)
Lot size:
0.04 Acres
Year built:
2003
Courtesy: Berkshire Hathaway HomeServices Keys Real Estate 305-743-7636
View additional info

ADDITIONAL INFORMATION

YOUR OCEAN FRONT FLORIDA KEYS ESCAPE AWAITS! Welcome to your own slice of paradise in the highly sought-after gated community of Venture Out on Cudjoe Key. This beautifully maintained 2-bedroom, 2-bath elevated home combines incredible ocean views, exceptional boating access, and resort-style living in one of the Lower Keys' most desirable waterfront communities. Step inside to soaring ceilings, abundant natural light, and expansive windows that bring the beautiful ocean views into the home. Covered outdoor spaces invite you to embrace the Keys lifestyle, from morning coffee overlooking the water to evening cocktails after a day on the boat. The primary suite features a king bed and ensuite bath, while the guest bedroom offers a queen bed and its own private covered porch. Boaters will love the 35' concrete seawall with heavy-duty dock posts, cleats, swim ladder, and two fish-cleaning tables. Below the home, covered parking, generous outdoor living space, and a 12'x12' concrete storage enclosure provide plenty of room for all your boating, fishing, and island gear. Venture Out offers an incredible resort lifestyle with a heated pool, hot tub, marina, fuel dock, boat ramps, pickleball, tennis, bocce, basketball, playground, recreation hall, pavilion, 24-hour gated security, and more. Nightly rentals are permitted, and the home generated approximately $100,000 in gross rental revenue in 2025, providing an attractive added benefit when you're not enjoying it yourself. Sold turnkey and ready to enjoy, this is your opportunity to own a waterfront retreat and experience the Florida Keys lifestyle from day one. Seller financing may also be considered with acceptable terms.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,080
Status:
Active
MLS#:
621295
Type:
Single Family
Subdivision:
Jolly Roger Estates (28.5)
Lot size:
0.16 Acres
Year built:
1978
Courtesy: Coldwell Banker Schmitt Real Estate Co. 305-743-5181
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ADDITIONAL INFORMATION

Your Florida Keys Retirement Retreat--and Investment Opportunity--Minutes from Key West Imagine waking up in the Florida Keys, stepping outside to your boat, and knowing the ocean is just moments away. Welcome to 400 La Fitte Road, a furnished canal-front home in Little Torch Key's desirable Jolly Roger Estates, ideally located on the oceanside at Mile Marker 28.5. Positioned on a spacious corner lot, this approximately 1,080-square-foot home offers two bedrooms, two bathrooms, durable CBS construction, tile flooring, accordion shutters, and a 40-foot concrete dock. Covered parking, garage and storage space, plus room for an RV or boat trailer, make it especially well suited for the relaxed Keys lifestyle. Boaters will appreciate the convenient ocean access, approximately three feet of reported control depth, and the neighborhood's community boat ramp. Why it stands out for retirement or investment: Offered furnished for an easier transition 28-day minimum rentals offering potential monthly income Quieter residential atmosphere without frequent weekly guest turnover Municipal sewer and FKAA water Spacious corner lot with room for recreational vehicles Close to Big Pine Key's shopping, dining, services, and National Key Deer Refuge Approximately 26-27 miles from Key West International Airport--normally about a 38-minute drive, depending on traffic Whether you envision a peaceful retirement retreat, a Florida Keys getaway, or an income-producing investment near Key West, this property offers the flexibility to enjoy it now while keeping future possibilities open. Come furnished. Bring the boat. Start living the Keys lifestyle.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,024
Status:
Active
MLS#:
621174
Type:
Single Family
Subdivision:
Mates Beach (28.5)
Lot size:
0.2 Acres
Year built:
1970
Courtesy: KeyIsle Realty 305-926-8559
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ADDITIONAL INFORMATION

This canal-front home offers the perfect blend of comfort, convenience, and the laid-back Florida Keys lifestyle. Located on a corner lot and built with durable CBS construction. This home features a spacious open floor plan, exceptional outdoor living, and direct boating access to Pine Channel. The outdoor amenities are truly a boater's dream. A brand-new 60-foot dock with boat slip, 17,000-lb. boat lift, and fish cleaning station provides everything you need to enjoy life on the water. The canal is ideal for an afternoon swim or snorkel, and you can watch parrotfish, snappers, and other marine life right from your dock. The Atlantic Ocean is only a two-minute boat ride away, offering quick access to world-class boating and fishing. Back at home, the large chickee hut creates the perfect setting for relaxing, entertaining, and enjoying outdoor BBQs. With the expansive dock and waterfront setting, the indoor/outdoor lifestyle this property offers is hard to beat. Inside, the spacious open floor plan is designed for entertaining and everyday living. Wood-plank ceilings and tile flooring run throughout the home, creating a warm and inviting Keys-inspired feel. The bathrooms have been updated with tile work throughout. For added storm protection and peace of mind, the home features CBS construction, a metal roof, and accordion shutters. Centrally located on Little Torch Key, this property is approximately 28 miles from Key West and 20 miles from Marathon. Just around the corner, Kiki's Sandbar offers food, drinks, and waterfront dining, while a grocery store and public boat ramp are only about five minutes away. Whether you're looking for a full-time residence, vacation getaway, or the perfect home base for enjoying the water, this property delivers the best of Florida Keys living. Call today to schedule your private showing! **Professional Photos Coming Mid September once tenant leaves**

Beds:
2
Baths:
2.00
Sq.Ft.:
864
Status:
Active
MLS#:
621115
Type:
Single Family
Subdivision:
Venture Out (23.0)
Lot size:
0.06 Acres
Year built:
2000
Courtesy: Homecoin.com 888-400-2513
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ADDITIONAL INFORMATION

Welcome to Oceanview Serenity, an exceptional, open-water retreat located in the gated community of Venture Out at Cudjoe Key (Mile Marker 23). This completely renovated 2-bedroom, 2-bathroom mid-rise offers rare, unobstructed turquoise ocean views as if you are floating on the water. A true boater's paradise, the property boasts a massive concrete seawall with effortless deep-water access. Critical structural and exterior updates provide unmatched peace of mind and substantial insurance benefits, including a brand-new roof, newly installed heavy-duty tie-down straps, and freshly refurbished, protected under-house support beams. Go inside to a bright, turnkey coastal interior where every detail has been thoughtfully updated, complete with a smart Nest thermostat for effortless climate control and energy efficiency. The main living space is framed by expansive windows that showcase panoramic water views. The heart of the home is a fully upgraded kitchen outfitted w/new appliances, and an oversized central island featuring generous built-in storage and a breakfast bar. The spacious primary suite serves as a luxurious private haven, highlighted by an upgraded ensuite bathroom complete with a double vanity and abundant storage. Outside, the covered deck offers the ultimate vantage point to relax in the ocean breeze and take in breathtaking Florida Keys sunrises over the water. Offered fully furnished and tastefully appointed, this home is 100% move-in ready to enjoy as a primary residence, private tropical getaway, or income-producing investment as a nightly rental. Venture Out is one of the rare communities in the Lower Keys that permits lucrative nightly rentals. Enjoy an incredible lineup of resort-style amenities, featuring a massive oceanfront saltwater swimming pool, an on-site marina store with a fuel dock, boat ramps, lighted tennis and pickleball courts, basketball, bocce, a vibrant recreation hall, and 24/7 gated security.

Beds:
2
Baths:
1.00
Sq.Ft.:
902
Status:
Active
MLS#:
621091
Type:
Single Family
Subdivision:
Summerland Key Cove (25.0)
Lot size:
0.13 Acres
Year built:
1956
Courtesy: Island Real Estate Company Florida Keys 305-395-0696
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ADDITIONAL INFORMATION

Tropical Waterfront Living in the Florida Keys! Welcome to 24923 Park Drive in beautiful Summerland Key, where laid back Florida Keys living meets ultimate waterfront lifestyle. This charming canal-front property offers an opportunity to create your own paradise in one of the Keys' most desirable boating communities. Positioned along a wide protected canal, the property features direct waterfront access to both Ocean & Gulf, 60 ft. concrete seawall, two boat lifts, private dockage. Making it ideal for boating, fishing, kayaking, and enjoying everything the Florida Keys has to offer. The spacious large open grassy yard offers room to personalize the outside space with a pool or outdoor kitchen, tiki, fire-pit or resort style entertaining oasis. This existing home offers a wonderful opportunity for a buyer looking to renovate, expand, or create a custom island retreat. With its metal roof, single level layout, tropical surroundings and exceptional waterfront setting this property provides the perfect foundation for a Florida Keys getaway, full-time residence, or investment opportunity. Bring your vision and transform this waterfront gem into your own private Keys paradise. Florida Keys Heritage trail for biking & walking close by. Summerland Key Private Air strip walking distance away.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,320
Status:
Active
MLS#:
621077
Type:
Single Family
Subdivision:
Jolly Roger Estates (28.5)
Lot size:
0.13 Acres
Year built:
2025
Courtesy: Meyer and Boumerhi Realty LLC 305-587-0268
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ADDITIONAL INFORMATION

Escape to paradise with this incredible waterfront property located on a deep boating canal in the heart of the Lower Florida Keys. Perfectly suited for boating enthusiasts and water lovers, this home offers dockage and a boat lift, and direct, easy access to the open waters of the Atlantic Ocean and Gulf of Mexico, making it a dream come true for those who enjoy fishing, cruising, or simply relaxing by the water. Featuring a spacious layout with multiple outdoor living areas (540 sqft of porches), this property is designed to maximize your waterfront lifestyle. Enjoy breathtaking sunset views over the salt ponds, tranquil breezes, and the peaceful surroundings of this serene neighborhood. Whether you're looking for a weekend getaway or a year-round retreat, this is the ultimate location for enjoying all that the Florida Keys have to offer. Built to the latest building code, this home provides peace of mind with robust construction that makes insurance a breeze - the lowest rates possible - around $8000 annually. 15,000 pound boat lift, perfect for any kind of boating needs! Tenant occupied, notice and pre approval required for showings. Seller is a FL licensed real estate agent.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,800
Status:
Active
MLS#:
620998
Type:
Single Family
Subdivision:
Cutthroat Harbor Est (23.0)
Lot size:
0.14 Acres
Year built:
1958
Courtesy: Internet Realty of the Florida Keys 305-745-9088
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ADDITIONAL INFORMATION

CUDJOE KEY CANALFRONT SPECIAL - LOWEST PRICED HOME IN CUTTHROAT HARBOR ESTATES. ASSUMABLE MORTGAGE AT 2.75% MOTIVATED SELLERS SAY BRING ALL OFFERS!! Situated on over 6,000 Square Feet on a deep water canal - this recently updated property provides easy boating access to both the Gulf and the Atlantic, making it a perfect home base for world class fishing, diving, SANDBARS and enjoying the keys lifestyle. New Upgrades Include - Fully remodeled kitchen All impact doors and windows All new split AC Units New flooring New Tankless Water Heater Upstairs, you'll find the fully remodeled kitchen with island which is perfect for entertaining and walk out to a large deck space. 1 Large bedroom and recently remodeled bathroom. The lower level features two bedrooms with a living room and an office space!!! A simple door and kitchenette could provide an owners lockout dividing both floors. Ample size lot provides room for Boat/RV parking in addition to a lush tropical landscape that provides afternoon shade on the majority of the property. This deal will not last long so do not delay on owning your piece of paradise. CALL LISTING AGENT MIKE KANE DIRECTLY FOR YOUR PRIVATE SHOWING AND SAVE!!!!!

Beds:
3
Baths:
3.00
Sq.Ft.:
1,500
Status:
Active
MLS#:
620954
Type:
Single Family
Subdivision:
Breezeswept Bch Est (27.5)
Lot size:
0.13 Acres
Year built:
2026
Courtesy: Meyer and Boumerhi Realty LLC 305-587-0268
View additional info

ADDITIONAL INFORMATION

*Construction process underway. Expected completion November/December 2026 Embrace the ultimate Keys lifestyle in this spacious 1,500 sqft home, ideally situated along a boating canal in the Lower Florida Keys, and close to Key West! Tucked away in a quiet, peaceful neighborhood. Inside, the home features generous living space, providing ample room to stretch out and make it your own. Indoor-outdoor living is at its best here, with a private swimming pool just steps from the back door--perfect for unwinding after a day on the water or enjoying sunny Florida afternoons. For boaters, the canal location offers easy water access, along with the convenience of a 10,000-pound boat lift to safely store your boat out of the water. After a day of fishing, cruising, or exploring, dock your vessel with ease and relax as you take in the beautiful waterfront views. Or stay on the screened in covered porch and enjoy the Keys breeze! The roughly 1100 sqft garage/lower enclosure offers abundant storage space for all your tools, pool toys, and outdoor gear, keeping everything organized and clutter-free. Plus, with a newly built home designed to the latest building codes, you'll benefit from low insurance rates, ensuring peace of mind and minimized risk from tropical weather. This home offers the ideal combination of comfort, convenience, and the laid-back Florida Keys lifestyle. Don't miss the opportunity to make it yours--schedule your private showing today at the model home. Photos are of model home and may not fully depict to be built home. Seller is licensed FL real estate agent.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,240
Status:
Active
MLS#:
620934
Type:
Single Family
Subdivision:
Summerland Key Cove (25.0)
Lot size:
0.14 Acres
Year built:
1982
Courtesy: Keller Williams Key West Compass Realty 305-292-0020
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ADDITIONAL INFORMATION

Summerland Key Cove -- Come by Sea or by Plane A unique opportunity in Summerland Key Cove offering both canal-front living and access to the community's private airport. Whether your Florida Keys lifestyle revolves around boating, flying, fishing, diving, or simply enjoying the water, this property offers a combination that is increasingly hard to find. Built in 1982, this 1,240 sq. ft. concrete block home features 2 bedrooms plus a versatile bonus room that can serve as a guest room, home office, gym, TV room, or additional living space. An approximately 400 sq. ft. screened room overlooking the canal adds substantial outdoor living space. Some major improvements have already been completed, including a 2022 metal roof, 2023 impact windows and doors on the upper level, and updated central A/C in 2020. Connected to central sewer. One of the property's standout features is the approximately 1,240 sq. ft. airplane hangar height of 9ft. Hard-to-find amenity in the Florida Keys--plus approximately 400 sq. ft. of additional storage and a concrete driveway. On the water, the property offers approximately 60 feet of concrete seawall on a 60-foot-wide canal, along with a davit. Two canal exits provide access to Kemp Channel, opening the way to both Atlantic Ocean and Gulf-side boating for fishing, diving, exploring, and enjoying the surrounding Keys waters. Located in an improved subdivision on a Tier III lot in AE-10 flood zone. Fencing is permitted. Access to the Summerland Key Cove airport and marina is available through membership. The home is currently tenant occupied with pets; advance notice is required for showings. NO tresspassing. Rented

Beds:
1
Baths:
1.00
Sq.Ft.:
368
Status:
Active
MLS#:
620746
Type:
Mobile Home
Subdivision:
Venture Out (23.0)
Lot size:
0.06 Acres
Year built:
1978
Courtesy: Bluescape Real Estate 305-203-2537
View additional info

ADDITIONAL INFORMATION

Welcome to Unit 533 in the gated waterfront community of Venture Out on Cudjoe Key! This well-maintained home features a spacious addition that provides extra living space and versatility. The addition includes a comfortable living area and a flex room currently used as additional sleeping space--ideal for guests, a home office, or hobby room. The property is currently occupied by a long-term tenant, offering an opportunity for a buyer seeking immediate rental income. The home offers a functional layout suitable for full-time living, seasonal enjoyment, or future investment use. Venture Out permits transient rentals with no minimum-night requirement, giving owners flexibility in how they choose to use the property. Community amenities include a large heated and chilled saltwater pool, hot tub, swimming lagoon, full-service marina with boat ramp and fuel dock, and convenient boating access to both the Gulf of Mexico and the Atlantic Ocean. Residents and guests also enjoy pickleball, tennis, bocce ball and basketball courts, a playground, two community centers, organized activities, and on-site church services. Looking for a fresh start? The property may also offer the potential to be converted into an RV lot or rebuilt to suit your vision, subject to current building regulations and community requirements. Schedule your private showing and explore the possibilities at Unit 533!

Beds:
1
Baths:
1.00
Sq.Ft.:
408
Status:
Active
MLS#:
620685
Type:
Mobile Home
Subdivision:
Venture Out (23.0)
Lot size:
0.05 Acres
Year built:
1989
Courtesy: Bluescape Real Estate 305-203-2537
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ADDITIONAL INFORMATION

Ocean-View Waterfront Retreat in Gated Venture Out on Cudjoe Key. NIGHTLY RENTALS ALLOWED Enjoy the Florida Keys lifestyle in this well-maintained 1-bedroom, 1-bathroom waterfront home located in the highly desirable gated community of Venture Out. With ocean views, direct boating access, excellent amenities, and nightly rentals permitted, this property is ideal as a vacation home, income-producing investment, or full-time residence. The home features numerous updates, including a new roof in 2018, air-conditioning system in 2020, and hot water heater in 2025. Additional improvements include newer impact-resistant windows, Bahama shutters, powder-coated storm panels, and updated mobile home tie-downs for added peace of mind. Boaters will appreciate the 35-foot concrete seawall with dock whips and quick access to the backcountry, offshore waters, and Atlantic Ocean. A concrete slab beneath the home provides valuable storage for fishing gear, kayaks, bicycles, and other Keys essentials. Venture Out offers an impressive array of amenities, including a large oceanfront saltwater swimming pool, community marina with fuel station, boat ramp, and boat wash-down area. Residents and guests also enjoy lighted tennis and pickleball courts, basketball and bocce courts, a recreation hall, waterfront pavilion, and regular community activities. The golf-cart-friendly neighborhood makes it easy to enjoy everything the community has to offer. Whether you are searching for a relaxing island escape, strong rental opportunity, or waterfront home in the Lower Keys, this property delivers an exceptional combination of location, boating access, amenities, and investment potential. Schedule your private showing today and experience this special Cudjoe Key property for yourself.

Beds:
1
Baths:
1.00
Sq.Ft.:
820
Status:
Active
MLS#:
620565
Type:
Single Family
Subdivision:
Misc Middle Torch Key (28.0)
Lot size:
2.5 Acres
Year built:
1958
Courtesy: Expert Realty LLC 305-587-7330
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ADDITIONAL INFORMATION

Imagine having the freedom to create your own secluded retreat in the heart of the Lower Florida Keys. This remarkable offering includes two adjacent 2.5-acre parcels, combining for approximately 5 acres--an exceptionally rare amount of land in the Florida Keys. Existing improvements include two separate residences, each offering one bedroom and one bathroom. One parcel is improved with a single-family home, while the other features a manufactured home. Both properties have established electric service and are connected to the sewer system, making them immediately usable while you plan for the future. The parcel at 2231 Middle Torch Road includes a ROGO allocation, creating an outstanding opportunity to construct a new home. Conceptual renderings have already been prepared to showcase one possible vision, but the possibilities are yours to define. Whether your goal is a peaceful island getaway, a private homestead surrounded by nature, or a property designed for generations to enjoy together, the setting provides the space and flexibility to bring those ideas to life. Spend your days boating the turquoise waters of the Lower Keys from a nearby private boat launch, then return home to the quiet beauty of native vegetation, abundant wildlife, and the iconic Key deer that call this area home. Opportunities to own five contiguous acres in the Florida Keys are exceptionally scarce. Combining privacy, natural beauty, and future development potential, this one-of-a-kind property offers the chance to create something truly special in one of the Keys' most unique settings.

Beds:
2
Baths:
3.00
Sq.Ft.:
1,819
Status:
Active
MLS#:
620532
Type:
Single Family
Subdivision:
Summerland Beach (25.0)
Lot size:
0.25 Acres
Year built:
2020
Courtesy: Island Real Estate Company Florida Keys 305-395-0696
View additional info

ADDITIONAL INFORMATION

Beach House Paradise in Summerland Key. Nestled in one of the Lower Keys' most desirable oceanside communities, this exceptional oceanfront retreat offers the perfect blend of luxury, privacy, and island living. A charming thatched-covered lanai and custom bamboo-etched glass doors welcome you into an open-concept floor plan where floor to ceiling windows frame breathtaking Atlantic Ocean views. The spacious living area flows effortlessly to an expansive waterfront terrace overlooking the pool, creating the ultimate indoor-outdoor lifestyle. Designed for entertaining, the lower level features a custom tiki-style bar, outdoor cooking area, hot tub, and multiple gathering spaces. Relax by the resort-style pool, unwind on your private sandy beach beneath the swaying palms, and enjoy the unparalleled beauty of oceanfront living. Located just minutes is Summerland Key's private airstrip, world class boating, fishing, diving and the renowned Looe Key reef, this exceptional property offers the very best of the Florida Keys lifestyle. 361 Avenue D is a rare opportunity to own your own slice of paradise.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,242
Status:
Active
MLS#:
620512
Type:
Single Family
Subdivision:
Dobie's Sub (24.0)
Lot size:
0.14 Acres
Year built:
2022
Courtesy: Island Real Estate Company Florida Keys 305-395-0696
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ADDITIONAL INFORMATION

Bring your water toys & experience island living in this newly built waterfront home in Summerland Key. The residence offers 3 bedrooms 2 bathrooms spacious modern design & trim. A durable metal roof, Hardie-board siding, impact windows and doors. Enjoy relaxing or entertaining on the covered porch, step out on the composite dock and be on the open ocean or Gulf in minutes, perfect for boating, fishing and sunset cruses. Keys biking trail steps away. Great local restaurants, convenient local island grocery store. Private Summerland Key Airstrip. Centrally located between Marathon and Key West, this property combines modern construction, waterfront convenience, low maintenance and easy access to both Keys' amenities. Ideal for a vacation retreat or full time home. Schedule your private showing today.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,587
Status:
Active
MLS#:
620456
Type:
Single Family
Subdivision:
Cutthroat Harbor Est (23.0)
Lot size:
0.24 Acres
Year built:
1982
Courtesy: Coldwell Banker Schmitt Real Estate Co 305-809-1400
View additional info

ADDITIONAL INFORMATION

Welcome to your oceanfront retreat on Cudjoe Key, where panoramic wide open ocean views, exceptional outdoor living, and easy boating access come together to create the quintessential Florida Keys lifestyle. Built on a lot and a half with durable CBS construction, this inviting 2-bedroom, 2-bath, 1,587 sq. ft. home is perfectly positioned to take advantage of its spectacular waterfront setting. The light-filled interior flows effortlessly into the spacious screened porch where you'll enjoy ocean breezes, morning coffee, waterfront dining and unforgettable sunrises and moonlit evenings. Just beyond, an expansive deck provides even more space for entertaining or simply relaxing while overlooking the endless blue waters. Inside, the primary suite serves as a peaceful waterfront sanctuary, featuring a private en-suite bath, walk-in closet, and sliding glass doors that open directly to the deck, allowing you to wake up to breathtaking ocean views each morning. A comfortable guest bedroom offers welcoming accommodations for family and friends. Boaters will appreciate the dock and davits, providing convenient access to the Atlantic for world-class fishing, diving, sandbar adventures and sunset cruises. The lower-level enclosure offers abundant storage for kayaks, paddleboards, fishing gear, and all of your island essentials. Whether you're entertaining guests on the spacious outdoor living areas, heading out for a day on the water, or simply soaking in the tranquil open water views, this Cudjoe Key waterfront home is your opportunity to embrace the relaxed, waterfront lifestyle the Florida Keys are known for.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,596
Status:
Active
MLS#:
620454
Type:
Single Family
Subdivision:
Cudjoe Gardens (21.0)
Lot size:
0.21 Acres
Year built:
2005
Courtesy: Coldwell Banker Schmitt Real Estate Co 305-809-1400
View additional info

ADDITIONAL INFORMATION

Wake up to breathtaking Florida Keys sunrises from this exceptional oceanside waterfront home in Cudjoe Key. Offering 1,596 square feet of living space on an 8,920-square-foot lot, this CBS-built residence features 3 bedrooms and 3 bathrooms, + Office/beddroom,combining durability, comfort, and the relaxed island lifestyle you've been dreaming of. Designed for both everyday living and entertaining, the home offers spacious living areas filled with natural light and beautiful canal views. Step outside to your private tropical retreat where a heated saltwater pebble coated pool overlooks the water, creating the perfect setting for morning coffee, afternoon relaxation, or entertaining family and friends. Built to withstand the Keys environment, the home features solid CBS construction and a metal roof for added peace of mind. The oceanside location provides easy access to world-class fishing, diving, snorkeling, and boating adventures. A marina and waterfront restaurant are conveniently located within walking distance, allowing you to enjoy dining, cocktails, and boating amenities just moments from your front door. Whether you're searching for a full-time residence, vacation getaway, or investment opportunity, this waterfront property offers the ideal blend of boating access, outdoor living, and the laid-back charm of the Florida Keys.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,056
Status:
Active
MLS#:
620463
Type:
Single Family
Subdivision:
Mates Beach (28.5)
Lot size:
0.15 Acres
Year built:
1963
Courtesy: Island Welcome Real Estate 305-923-9161
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ADDITIONAL INFORMATION

A Classic Keys Boating Cottage! Exceptional value for a 3 bedroom 2 bath waterfront home in the Lower Keys! With 60' of seawall, enjoy easy boating access to nearby hot spots in the gulf and ocean side. The State Road 4a boat ramp is just a few doors away which is so convenient to launch your boat. Plenty of parking out front and room for a pool. Featuring laminate floors, a dedicated laundry space, on demand hot water heater and a large pantry storage closet.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,120
Status:
Active
MLS#:
620439
Type:
Single Family
Subdivision:
Misc Summerland Key (25.0)
Year built:
2006
Courtesy: Berkshire Hathaway HomeServices Knight & Gardner Realty 305-294-5155
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ADDITIONAL INFORMATION

Well-maintained 3-bedroom, 2-bath home offering 1,120 square feet of comfortable living space in a small, well-kept community in Summerland Key. This home is in excellent condition, offers ample parking, and provides a wonderful opportunity for affordable homeownership in the Lower Keys. Subject to affordable housing deed restrictions.

Beds:
2
Baths:
3.00
Sq.Ft.:
1,152
Status:
Active
MLS#:
620443
Type:
Single Family
Subdivision:
Mates Beach (28.5)
Lot size:
0.21 Acres
Year built:
1982
Courtesy: Coldwell Banker Schmitt Lower Keys (KW) 305-872-3050
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ADDITIONAL INFORMATION

Are you looking for a canal-front home that could use your TLC? Situated on a 9,375 sq. ft. fenced lot, this 2-bedroom, 3-bath CBS opportunity is about mid-way between the convenient 4A Boat Ramp to the west and Pine Channel to the east. Bright and airy, the extra-large kitchen was updated with new cabinets, stainless steel appliances and granite counters in recent years. The remainder of the house is ready for you to continue with updates. The 2 bedrooms each have walk-in closets and older carpet, the awning windows and sliding glass doors appear to be original, the house is cooled by window/wall unit A/Cs, and there are no shutters. A great bonus is the permitted 3rd bathroom in the downstairs storage. The spacious screened porch upstairs overlooks the huge back yard and canal. Measuring 62.5' x 150', the fenced property offers plenty of room for adding a pool, tiki or whatever options you might want to explore. Metal roof was replaced in 2017. **Do not walk the property without agent.** Various government agencies own most of the environmentally sensitive land across the street to the north.

Beds:
5
Baths:
4.00
Sq.Ft.:
3,352
Status:
Active
MLS#:
620413
Type:
Single Family
Subdivision:
Misc Summerland Key (25.0)
Lot size:
9.69 Acres
Year built:
2015
Courtesy: Coldwell Banker Schmitt Real Estate Co 305-809-1400
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ADDITIONAL INFORMATION

Discover one of the Florida Keys' most extraordinary private island retreats. Encompassing 9.69 acres of pristine tropical landscape, Howell Key offers an unparalleled opportunity to own an off-grid luxury island surrounded by breathtaking open water views from sunrise to sunset. Designed for those who value privacy, adventure, and refined coastal living, the island features miles of groomed trails, resort-style pool, sandy beach, pickleball court, chicken coop, pasture, and expansive barn. At the heart of the island sits a beautifully crafted 5-bedroom, 4-bath residence encompassing 3,352 sq. ft. Cathedral ceilings, elegant coastal interiors, and expansive gathering spaces create a warm yet sophisticated atmosphere, while walls of impact-rated glass invite natural light and panoramic water views throughout the home. The layout is designed to comfortably accommodate family and guests with an attached primary suite serving as a private sanctuary, complete with a generous walk-in closet. A separate guest wing is accessed via a breezeway and features its own living room, breakfast bar, and 2 private bedrooms creating a welcoming retreat while maintaining privacy from the main residence. Beyond the main residence, the island unfolds as a private playground. Wander along groomed walking trails, relax by your saltwater pool, launch your kayaks from your own sandy beach, enjoy pickleball with friends, or watch the sunset from your dock. Built for resilience and efficiency, the home features SIP construction, Hardie Board siding, a standing seam metal roof, impact windows and doors, whole-house reverse osmosis water filtration, and an off-grid solar power system. Elevated approximately 10 feet above base flood elevation, the property offers both sustainability and peace of mind. Island purchase comes with barge, golf cart, tractor, and a private mainland lot for car storage. Howell Key is a private island lifestyle few will every have the opportunity to experienc

Beds:
4
Baths:
4.00
Sq.Ft.:
1,671
Status:
Active
MLS#:
A12042729
Type:
Other
Subdivision:
CUTTHROAT HARBOR ESTS
Lot size:
0.2 Acres
Year built:
2027
Courtesy: MWX Realty, LLC. Merlo-Garzon Joaquin 786-381-2673
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ADDITIONAL INFORMATION

Brand new waterfront in the Keys, built for you from the ground up. This is a preconstruction home in Cutthroat Harbor Estates. You buy now and it gets built for you, delivered turnkey. Picture it: your boat at the private dock on approx. 102 ft of canal seawall, a pool and jacuzzi below, coffee on the rooftop deck. Elevated 4 bed, 4 bath, outdoor kitchen, solar and efficient systems, brand new and low maintenance. And the best part? The permit is already secured, so your home gets built now instead of years from now.

Beds:
3
Baths:
2.00
Sq.Ft.:
960
Status:
Active
MLS#:
620381
Type:
Single Family
Subdivision:
Cutthroat Harbor Est (23.0)
Lot size:
0.18 Acres
Year built:
1991
Courtesy: Keller Williams Key West Compass Realty 305-292-0020
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ADDITIONAL INFORMATION

53 Treasure Chest Drive in Cudjoe Key is more than a home--it's your chance to own a piece of paradise. From the moment you arrive, you'll feel the laid-back island vibe paired with the comfort and security today's buyers demand, including impact windows and doors for year-round peace of mind. Bright, airy, and designed for easy living, this property invites you to slow down, entertain more, and enjoy everything the Florida Keys has to offer. Whether it's morning coffee in the tropical breeze or evenings under the stars, this home delivers the lifestyle people dream about--but rarely find. And the best part? You're just a short drive to Key West, giving you access to world-class dining, nightlife, and boating--while still enjoying your own private escape.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,296
Status:
Active
MLS#:
620391
Type:
Single Family
Subdivision:
Indian Mound Estates (19.5)
Lot size:
0.12 Acres
Year built:
2018
Courtesy: Expert Realty LLC 305-587-7330
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ADDITIONAL INFORMATION

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 overlooking living area, stainless steel appliances, light and stylish colors throughout. Wood-look tile plank flooring, crown molding, 9-ft ceilings, recessed lighting and ceiling fans in all bedrooms and living room. Full size laundry room and on-demand hot water heater. Large master bedroom with en-suite bathroom, dual sink vanity and large walk-in closet. 2 guest bedrooms and full guest bathroom. Large covered porch off the main living/kitchen area, fenced on 3 sides. Newer downstairs storage room, room for boat/trailer; boat ramp is one street over and you are less than a mile from Sugarloaf Elementary and Middle school. Quick access to Key West and bases.

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Andrea D. Conner, License # BK3437731, Xome Inc., License CQ1043756, [email protected], 844-400-XOME, 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067

The data relating to the real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Florida Keys Board of Realtors® Florida Keys MLS, Inc. Real Estate listings held by brokerage firms other than the owner of this site are marked with the MLS logo and detailed information about them includes the name of the listing broker's office. Information is provided exclusively for consumers’ personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that data is deemed reliable but is not guaranteed accurate.


Andrea D. Conner, License # BK3437731, Xome Inc., License CQ1043756, [email protected], 844-400-XOME, 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067

The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Use of search facilities of data on the site, other than a consumer looking to purchase real estate, is prohibited. © 2026 MIAMI Association of REALTORS®, all rights reserved.




Summerland Key 33042 Real Estate

Summerland Key is located in Florida. Summerland Key, Florida 33042has a population of 6,609. Summerland Key 33042 is less family-centric than the surrounding county with 17.31% of the households containing married families with children. The county average for households married with children is 20.65%.

The median household income in Summerland Key, Florida 33042 is $95,365. The median household income for the surrounding county is $73,153 compared to the national median of $69,021. The median age of people living in Summerland Key 33042 is 50.4 years.

Summerland Key Weather

The average high temperature in July is 89.4 degrees, with an average low temperature in January of 63.4 degrees. The average rainfall is approximately 44.4 inches per year, with 0 inches of snow per year.

Summerland Key Map

Summerland Key Real Estate Market Conditions

  • Median sales price

    $952,500
    26.6%
    change since last quarter
  • # Active listings

    254
    30-day change

Summerland Key Schools and Demographics

Education near Summerland Key, FL

City County
High School Graduates 96.84 92.07
College Degree - 2 year 7.68 7.93
College Degree - 4 year 41.72 35.69
Graduate Degree 10.7 9.88
Expenditures per Student 20,907 20,907
Students per Teacher 14.7 14.7

Elementary Schools near Summerland Key, FL

Grades Students P/T Ratio ZIP
Big Pine Academy PK - 08 177 12.6 33043
Gerald Adams Elementary School PK - 05 544 13.3 33040
Horace O'Bryant School PK - 08 1,059 14.3 33040
Key Largo School PK - 08 847 14.1 33037
Key West Montessori Charter School KG - 08 149 16.6 33040
Monroe Virtual Instruction Program (District Provided) KG - 05 6 33040
Ocean Studies Charter KG - 05 104 11.2 33070
Plantation Key School PK - 08 435 12.8 33070
Poinciana Elementary School PK - 05 663 15.1 33040
Sigsbee Charter School KG - 08 478 17.1 33040
Stanley Switlik Elementary School PK - 05 566 14.2 33050
Sugarloaf School PK - 08 526 15 33042
Treasure Village Montessori Charter School PK - 08 213 14.2 33036

Middle Schools near Summerland Key, FL

Grades Students P/T Ratio ZIP
Glynn Archer Elementary School PK - 05 394 15.8 33040

High Schools near Summerland Key, FL

Grades Students P/T Ratio ZIP
Coral Shores High School 09 - 12 733 17.4 33070
Key West Collegiate School 09 - 12 78 15.3 33040
Key West High School 09 - 12 1,193 16.8 33040

Ungraded Schools near Summerland Key, FL

Grades Students P/T Ratio ZIP
* Keys Center 08 - 12 11 11 33040
Academic Connections for Excellence 06 - 12 11 33040
Adult/Vocational/Community Education AE - AE 0 33040
Hurricane Island Outward Bound 06 - 12 12 33037
Marathon School 06 - 12 667 18.5 33050
Monroe Virtual Academy (Course Offerings) 06 - 12 0 33040
Monroe Virtual Franchise 06 - 12 4 33040
Monroe Virtual Instruction Program KG - 12 0 33040

Demographics near Summerland Key, FL 33042

Zip Code City
Neighborhood Type Small town
Population 6,609 82,244
Population Density 259 84
Median Age 50.4 48
People per Household 2.4 2.4
Median Household Income 95,365 73,153
Average Income per Capita 61,118 50,050

Real estate near Summerland Key