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$1,079,000
4 Beds ⋅ 2 Baths ⋅ 616878 MLS
Welcome to 2926 Flagler Avenue! This single-family home has four bedrooms and two baths, a swimming pool and is nestled on a 6,360 square foot lot located in a wonderful New Town central location. The spacious interior affords you the opportunity to entertain family, friends, and truly relax in comfort. Having been well maintained throughout the years, this CBS home has a v-crimp metal roof, impact rated windows and doors throughout plus accordion shutters providing an additional layer of peace of mind protection. The open layout features a flexible living atmosphere that leads to the possibility of one bedroom being a lockout with its own exterior entrance or an ideal multigenerational living arrangement. The low maintenance backyard is perfect for entertaining, and the swimming pool is sure to bring joy to those who yearn for living the Key West lifestyle. A fully fenced yard offers privacy and security. Located within minutes of shopping, the beaches, and many wonderful dining venues that Key West has to offer. This property is the one that checks off many of the boxes and is competitively price to sell. Please call me today to view your future home!

2926 Flagler Ave, Key West
$1,050,000
3 Beds ⋅ 2 Baths ⋅ 621237 MLS
Tucked away on a quiet lane just off Frances Street, this charming historic cottage offers the character and location that make Old Town Key West so special. This three-bedroom, two-bath home features cathedral ceilings, stained glass windows, and plenty of historic charm. The first-floor bedroom offers added convenience and flexibility, while two additional bedrooms upstairs provide comfortable separation for family or guests. Beautiful porches and a private deck create inviting spaces for outdoor dining and relaxing. Ideally located in Old Town, you are just minutes from Duval Street, local restaurants, galleries, shops, and everything that makes Key West such a unique place to live and enjoy. The property is in the X-Zone.

614 Roberts Ln, Key West
$1,049,000
3 Beds ⋅ 3 Baths ⋅ 620351 MLS
Welcome to an incredible opportunity to enjoy an exceptional amount of home and land in the Lower Keys. This beautifully updated 3-bedroom, 2.5-bath waterfront home sits on a rare 12,000 sq. ft. double lot in the heart of Big Pine Key, offering generous space both inside and out without sacrificing the relaxed Keys lifestyle. Thoughtfully renovated throughout, the home features a bright, spacious living room, versatile office/den, and an updated kitchen and dining area ideal for everyday living and entertaining. Boaters will appreciate canal access to Pine Channel, with quick access to both Atlantic and Gulf waters. The screened porch overlooking the canal is the perfect spot to relax, dine outdoors, or take in the peaceful waterfront setting. Outside, the expansive double lot offers ample room for parking, pets, and outdoor activities, with plenty of space to add a pool and create your own backyard retreat. The open area beneath the home provides incredible flexibility for storage, a workshop, recreational space, or outdoor living. With its generous home size, rare double-lot setting, waterfront access, and versatile lower-level space, this property offers exceptional value in the Lower Keys. Located in a desirable, family-friendly neighborhood, this home captures the best of Big Pine Key living--peaceful surroundings, abundant space, and easy access to the water.

1615 Fern Ave, Big Pine
$1,029,000
4 Beds ⋅ 2 Baths ⋅ 621054 MLS
2809 Flagler Ave -2,274 Square Feet of Space, Priced to Move Rarely does a home this size come up in Key West at this price point. At 2,274 square feet, this 4-bedroom, 2-bathroom residence offers significantly more room than the typical Old Town or Mid Town property -- and it's priced well below what comparable square footage commands elsewhere in the 33040 zip code. Originally built in 1953, the home received a two-story addition in 2002 that expanded both living space and functionality, giving it a layout that feels far more generous than its neighbors. Inside, 3/4-inch red oak flooring runs throughout, and every bedroom includes its own closet for real storage -- not an afterthought. A spacious office/flex room adds even more usable square footage, ideal as a home office, guest space, or additional living area. A dedicated laundry room and a large pantry/storage area off the carport round out the practical extras that are hard to find in homes half this size.

2809 Flagler Ave, Key West
$1,024,000
2 Beds ⋅ 2 Baths ⋅ 619409 MLS
Boater's dream waterfront on Ramrod Key with no-bridge ocean access, dual boat lifts, and open Atlantic access in minutes. Offered fully furnished and turnkey, this is Keys living at its best. Welcome to Breezeswept Dockside Retreat, designed for those who want to spend more time on the water. Situated on a 40' wide canal with approximately 3' control depth, you'll enjoy quick access to the Atlantic, Looe Key Reef, world-class fishing, diving, backcountry sandbars, and nearby Picnic Island. A fuel and dive shop are conveniently located at the north end of the canal. Launch from your backyard with 60' of composite dockage (2022), a 14,000-lb and 6,000-lb boat lift, making this property ideal for multiple vessels and serious boating enthusiasts. Inside, the open-concept living area flows onto a full-length covered verandah overlooking the canal. Outside, relax in the private saltwater pool, entertain on the spacious deck, and enjoy tropical landscaping after a day on the water. Property Highlights: • Turnkey, fully furnished • No-bridge ocean access • 60' composite dock (2022) • 14K & 6K boat lifts (2022) • Saltwater pool (2019) • Metal roof (2018) • A/C (2022) • Lower enclosure (2021) • 28-day rentals allowed • Flood Zone AE • Voluntary HOA • Low insurance: under ~$7K wind/homeowners + assumable flood policy (~$520) Rarely does a waterfront home combine immediate boating access, premium dockage, a private pool, and turnkey convenience in one exceptional Lower Keys property.

27416 Cayman Ln, Ramrod
$1,019,000
3 Beds ⋅ 2 Baths ⋅ 619820 MLS
Accessibility elevator! Welcome to your Lower Keys retreat where comfort, and coastal living come together beautifully along with the convenience of an interior elevator. Situated on the desirable boating canal system of Pine Channel Estates, this 3 bedroom, 2 bath home is designed for those who appreciate the water based lifestyle. Inside, soaring vaulted ceilings create an open and airy atmosphere throughout the home, while the interior elevator offers effortless and/or handicap access and convenience. Expansive living spaces flow seamlessly onto a large screened deck and two additional open-air decks off of the canal side bedrooms, all perfectly positioned to capture peaceful canal views. Elevated above flood and built to withstand severe weather conditions with impact resistant windows and metal roof. For boating enthusiasts, this property is truly exceptional. Featuring two boat docks and a 12,000-pound boat lift, you'll enjoy quick and easy access to the ocean and gulf side right from your backyard. Whether you're heading out for a day on the boat, entertaining guests outdoors, or simply relaxing in the coastal breeze, this home delivers the ultimate waterfront lifestyle. **Handicap accessible with interior elevator shaft ~ Sewer assessment is paid in full ~ Fire & Liability (homeowners) insurance $2,318.30**

29555 Enterprise Ave, Big Pine
$1,000,000
3 Beds ⋅ 2 Baths ⋅ 620253 MLS
Mermaid Landing: Investment Opportunity & Coastal Retreat Discover a one-of-a-kind property in the Florida Keys that offers unparalleled flexibility -- Mermaid Landing. This 3-bedroom, 2-bathroom home is perfect for savvy investors or those seeking a personal paradise, featuring rare access to a beach on the Gulf of Mexico. Located just 15 minutes from Key West, the property currently generates income with a long-term tenant while offering the ultimate coastal lifestyle. The 33,000 sqft lot is a treasure trove of potential. A partially fenced yard with a double gate provides ample parking for vehicles, boats, and RVs. This property is as versatile as it is attractive. The true gem? Direct access to a beach that lets you step straight from your artificial turf yard onto the Gulf shoreline, delivering breathtaking water views that most can only dream about. Newly renovated with a spacious primary bedroom and modern kitchen, Mermaid Landing seamlessly transitions between a profitable investment and a personal sanctuary. The existing tenant ensures immediate income potential, while the property's design offers endless possibilities for rental management or personal use. More than just real estate, this is your ticket to Florida Keys magic. Whether you're an investor seeking reliable returns or a buyer wanting a coastal retreat, Mermaid Landing delivers. With its prime location, access to a beach, and incredible versatility, this property is a rare find. Don't miss your chance to own something extraordinary. Schedule an exclusive viewing today and prepare to be captivated by the endless possibilities of Mermaid Landing.

813 2nd St, Big Coppitt
$999,000
3 Beds ⋅ 2 Baths ⋅ 620987 MLS
Charming Historic Old Town Key West Home, Ready for Its Next Chapter! Here's an opportunity for the buyer who sees possibility where others see a project. This 3-bedroom, 1.5-bath historic Key West home is tucked into the heart of Old Town, just minutes from the Historic Seaport, downtown, restaurants, shopping, and everything that makes island living so special. With classic Key West architecture, a welcoming front porch, hardwood floors, vintage windows, and plenty of original character, the home offers a wonderful starting point for a thoughtful renovation. The interior has been freshly painted, but this is a property that will require renovation and is best suited for a buyer ready to take on a true restoration project. Currently tenant occupied, the property also offers the advantage of existing rental income while a new owner makes plans, lines up contractors, or prepares for a future renovation or move-in. The existing floor plan includes generous living space, three bedrooms, a full bath downstairs, a half bath upstairs, and a private backyard with the potential to become a lush tropical retreat. For the right buyer, the appeal is undeniable: an authentic Old Town home, a highly desirable location, existing income, and the opportunity to restore, reimagine, and create something truly special. Bring your contractor, your creativity, and your vision. This one isn't pretending to be turnkey, but it just might be worth the work. *some photos digitally enhanced only to remove personal belongings

506 Grinnell St, Key West
$999,000
4 Beds ⋅ 3 Baths ⋅ 620041 MLS
This newly built 2026 home on Stock Island delivers what buyers rarely find in the Florida Keys: true new construction, built to current code, with a fully legal guest suite and insurance costs designed to be as manageable as possible -- all priced under $1M. The main residence offers 3 bedrooms, 2 bathrooms, and over 1,500 square feet of thoughtfully designed living space elevated 18 feet above grade. Interiors feature waterproof and scratch-proof luxury vinyl plank flooring, quartz countertops, stainless steel appliances, and in-unit washer and dryer. HardiePlank siding, impact-rated doors and windows, and a metal roof complete a build package engineered for Keys living. Central air conditioning keeps the main home comfortable year-round. The elevated guest suite -- positioned at 9 feet with its own private entrance below the main home -- adds one bedroom, one bathroom, and approximately 500 square feet of additional living space, complete with quartz countertops, stainless steel appliances, in-unit laundry, and a mini-split system. Live in one, rent the other, or house extended family with total privacy. Similar properties are bringing in over $6500 per month in rent. The fully fenced, rock-covered lot provides covered parking under the home and additional off-street parking out front -- a genuine premium in the Keys. Stock Island puts you one bridge from Old Town Key West, with marinas, restaurants, and the energy of the Keys right at your door.

49g Miriam St, Stock Island
$998,000
3 Beds ⋅ 2 Baths ⋅ 619159 MLS
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, washing boats & vehicles @ approximately 2,500 gallons each tank. Enjoy quick boating access to the Gulf side for premier tarpon, bonefish and permit flats, and close proximity to Sugarloaf Marina for shallow draft outboard vessels. This canal-front property includes a 30' composite dock with fish cleaning station and launching for kayak or paddle board. Additional highlights: detached carport/workshop, storage shed, and large cistern for irrigation and cleaning boats and vehicles etc.. **VA assumable loan @ 2.25% - VA must approve** **VA Assumable Loan @ 2.25% may be a possibility to a qualified VA Buyer** SELLER'S INSURANCES: FLOOD $2,318, WIND $6,683, HOMEOWNERS $2,159.75 **Canal entrance is 3'+/- at low tide**Shallow draft outboard vessels**Buyer to verify if suitable for Buyers' boating needs**

83 Sugarloaf Dr, Sugarloaf
$995,000
3 Beds ⋅ 3 Baths ⋅ 620923 MLS
Get excited about this mid-town oasis. Behind the fence is a charming three-bedroom three bath residence with beautiful grounds, off-street parking, newer roof, impact glass windows and doors, central and ductless air conditioning, storage shed, and much more. The huge kitchen, dining and living rooms are unique. The third bedroom has a separate entrance with private outdoor space, perfect for roommates or mothter-in-law suite. Come see today and make this beautiful property your new home or entry-level investment in Key West.

2309 Patterson Ave, Key West
$995,000
3 Beds ⋅ 2 Baths ⋅ 620700 MLS
OWNER FINANCING. 27452 ANGUILA LANE RAMROD KEY FOR RENT. REPAINTED INSIDE AND OUT. ALL NEW FLOORING. 1400 SQFT 180 MPH RATED 3/2 HOME. 300SQFT ENCLOSURE FOR ALL YOUR FISHING NEEDS.40' DOCK ON AN OVERSIZED CORNER LOT WITH LOTS OF ROOM FOR RV AN BOAT PARKING. MINUTES FROM LOOE KEY REEF. 9' CEILINGS, CROWN MOLDING AND CENTRAL AC. FULLY PEA ROCKED YARD FOR LOW MAINTENANCE. NEW METAL ROOF, HURRICANE WINDOWS AND DOORS. GRANITE COUNTERS. RENT IS $4,750 PER MONTH. $4,000 SECURITY. $8,950 AND YOUR IN. CALL FOR PRIVATE SHOWING show contact info . AVAIL NOW. OWNER REALTOR. RIDE BY FIRST AND IF YOU LIKE IT, CALL ERICA. LONG TERM LEASE CONSIDERED.PURCHASE $1,199,000.00, $50,000 DOWN PMT. WILL FINANCE BALANCE FOR 5 YEARS AT 8% NO WIND NO FLOOD INSURANCE REQUIRED. HUGE SAVINGS. HUGE OPPORTUNITY. NEGOTIABLE. OWNER REALTOR. RIDE BY IF YOU LIKE IT CALL FOR SHOWING. APPROX. MONTHLY PMT. $8,800.00

27452 Anguila Ln, Ramrod
$992,000
3 Beds ⋅ 2 Baths ⋅ 620547 MLS
Old Town 'Diamond in the Rough' near Bay View Park with the highly coveted Off-Street parking. Unique opportunity to acquire a corner lot of over 4,500 sq ft in quiet Old Town neighborhood. Good amount of yard space. No active or expired building permits or code cases. Being sold As-Is with no repair & no clean up. Does have an existing fiberglass pool surrounded by a wooden deck. There is an existing concrete pad behind a double fence that could provide secured off street parking. Side yard is 37 Ft from side of house to fence and 49 Ft wide. Back yard with pool and deck is 27 X 27. Lots of potential. Major renovation project. Probably needs cash buyer. Contract requires court approval due to guardianship. Proof of funds must accompany offer. Create your island oasis at 1119 Florida St.

1119 Florida St, Key West
$989,000
3 Beds ⋅ 2 Baths ⋅ 620596 MLS
Elevated Coastal Living in Breezeswept Beach Estates. Skip the typical vacation rentals & step into a home designed specifically for the genuine Florida Keys lifestyle. Situated on a quiet street within Breezeswept Beach Estates, this well-maintained 3-bedroom, 2-bathroom stilt home perfectly balances premier boating access with a peaceful, scenic setting. The property's positioning is truly distinct. While the back of the home centers around a deep-water canal optimized for quick navigation to open water, the front looks out over tranquil salt ponds--treating you to wide-open, mirror-like sunset views without the interruption of forward neighbors. This home has direct ocean side access or easily head out back to the Gulf for some backwater fishing or spending the day at the sandbar via Niles Channel or Pine Channel. This property will stand out as a your own piece of paradise, a pristine basecamp for the serious waterman or anyone seeking an authentic island retreat. Key Features Include: *The heart of the home features a sleek kitchen with stainless steel appliances, complemented by fully updated bathrooms, and fixtures throughout. *Large windows capture the distinct natural light of the lower keys, making the interior feel bright, airy, and connected to the water. Enjoy waterfront views from every room in the house. *Unwind on the expansive, screened back porch overlooking your canal, or catch the evening colors shifting over the salt ponds from the front balcony. *The ground level features a massive, 600 sq. ft. fully enclosed storage enclosure, giving you a secure, dedicated space for dive tanks, fishing gear, and all your workspace needs.

673 Indies Rd, Ramrod
$982,600
2 Beds ⋅ 2 Baths ⋅ 621115 MLS
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.

701 Spanish Main Dr Unit 198, Cudjoe
$980,000
3 Beds ⋅ 2 Baths ⋅ 619877 MLS
This three bedroom , two bathroom home sits on an expansive 12,200 square foot piece of property in the highly sought after Breezeswept Beach Estates neighborhood on Ramrod Key. Upstairs there are two bedrooms and one bath, and a large kitchen and living room. Downstairs is a one bedroom, one bathroom bungalow with a complete kitchen! The exterior of the property has several updates, including storage sheds, 90 feet of brand new docks with water, electric and a brand new built in fish cleaning table. A new roof was installed in 2023. Plenty of room to stretch out on this property, lots of parking, room for boat trailers, and totally fenced in for your pets. Excellent location for open water access, short canal ride and a couple minutes to picnic island for a relaxing afternoon and sunset!

750 W Indies Dr, Ramrod
$979,000
4 Beds ⋅ 2 Baths ⋅ 620453 MLS
When value matters, this solid concrete New Town home stands apart with one of the most compelling price-per-square-foot opportunities on the market. Substantial 4-bedroom, 2-bath home featuring a dedicated office, offering an exceptional combination of comfort and functionality. Situated on an expansive 8,448-square-foot corner lot, the property provides 2,111 square feet of living space, two driveways, off-street parking with an attached carport, a Tesla charging station, and ample room to add a pool. Designed for easy living and entertaining, the open-concept kitchen and living area is enhanced by soaring cathedral ceilings with exposed beams and an abundance of large, light-filtering windows that create a bright and inviting atmosphere throughout. A welcoming front porch, set back amongst mature trees, provides the perfect place to relax and unwind. The elevated home features double-pane windows, noise-dampening door improvements, a V-crimp metal roof, and beautiful terrazzo floors that add timeless Key West character. The solid concrete construction offers lasting durability and an excellent foundation to fine-tune and personalize the home to suit your vision. The fully walled property provides privacy and generous outdoor space. With its larger-than-average footprint, oversized corner lot, two driveways, and endless potential for a backyard pool oasis, this home presents an outstanding opportunity to enjoy the very best of Key West living. Whether you're searching for a comfortably sized family home just or a property with the perfect canvas to create your dream home, this opportunity offers exceptional value.

1500 5th St, Key West
$979,000
2 Beds ⋅ 2 Baths ⋅ 620187 MLS
Wonderful Home with a Small Cottage, Salt Water Pool, and Off Street Parking, and 2 Brand New Roofs, on the Main House and the Guest Cottage!. Additionally- there is a New Insurance Mitigation report dated 8/28/2026! Affordable insurance premiums. Currently $13,367.48 a year for flood, windstorm, and homeowners insurance. The Main Home has an open living room with cathedral ceilings, and a loft . The Kitchen has French Doors leading to a large deck, and a private back fenced yard. Chicago brick surrounds the Salt Water Pool and cottage, with lots of additional space. There are plans by Serge with Artibus Designs for an addition added on to the home if desired giving an additional bedroom, bath, dining room, etc. Wonderful property as is or expand for more square footage!

3808 Duck Ave, Key West
$975,000
4 Beds ⋅ 3 Baths ⋅ 621181 MLS
Brand-New Waterfront Home in the Florida Keys Discover the perfect blend of modern luxury and relaxed island living in this stunning brand-new construction home in the Florida Keys. Boasting beautiful canal views, this exceptional property offers the ideal setting to enjoy the tropical lifestyle the Keys are famous for. The home features 4 spacious bedrooms and 3 beautifully appointed bathrooms, providing plenty of room for family, guests, or entertaining. The open and inviting layout is designed to maximize natural light and create seamless connections between the indoor and outdoor living spaces. Enjoy peaceful mornings overlooking the canal and breathtaking sunsets in your own private paradise. With its modern construction, spacious living areas, and desirable waterfront setting, this home is an excellent opportunity for anyone looking to experience the Florida Keys lifestyle in a brand-new residence. Modern design. Spacious living. Waterfront views. Your Florida Keys dream starts here.

31441 Ave F, Big Pine
$975,000
2 Beds ⋅ 2 Baths ⋅ 619692 MLS
Peaceful serenity found on this 22,077 square foot property with a cozy two bedroom one and one-half bath. Open concept large kitchen and living room leading out to the expansive deck overlooking the canal. Both bedrooms also have doors leading to the wrap around deck! The cathedral ceilings and wood trims give this home beach cottage character! The lower level has an amazing amount of storage with built in shelving. The canal side of the property boasts both a new 40 ft dock with a 10,000 lb. boat lift and a seawall. Easy access to open water! You won't believe the size of this property, plenty of space to park your boat trailers or put in a huge inground pool. Eden Pines is truly a sought after neighborhood, with lots of wildlife everywhere including your daily key deer visitors!

29131 Watson Blvd, Big Pine
$964,999
3 Beds ⋅ 2 Baths ⋅ 618556 MLS
Welcome to island living in Big Pine Key. Situated on a desirable corner lot, this beautifully remodeled 3-bedroom, 2-bathroom home offers 70 feet of dockage with davits, providing excellent boating access and true waterfront Keys living. The home has been fully updated, featuring a newer roof, updated windows, modern flooring, renovated kitchen and bathrooms, and upgraded lighting throughout. The property also features a large garage and ample storage space, ideal for boating gear, tools, or recreational equipment. Enjoy privacy, outdoor living, and easy access to open water, nearby parks, and local amenities. A fantastic opportunity for a full-time residence, vacation retreat, or investment property in the Lower Keys.

30368 Killdeer Ln, Big Pine
$950,000
3 Beds ⋅ 3 Baths ⋅ 621180 MLS
Brand-New Waterfront Home in the Florida Keys Discover the ultimate Florida Keys lifestyle in this stunning brand-new construction, perfectly designed for those who love boating, waterfront living, and the beauty of the Gulf. This exceptional property features 3 spacious bedrooms, 2.5 bathrooms, and a private boat dock, providing direct access to the Gulf for unforgettable days on the water. The home offers generous parking space and is being sold fully furnished, allowing you to move in and immediately enjoy everything the Keys have to offer. From the modern finishes and comfortable living spaces to the incredible waterfront setting, every detail was designed for relaxation and enjoyment. Step outside and enjoy your own private waterfront paradise, with your boat just steps from your door and direct access to the Gulf. Whether you're looking for a luxurious primary residence, a vacation retreat, or an exceptional investment opportunity, this property offers the perfect combination of new construction, boating access, comfort, and the laid-back Florida Keys lifestyle. Your dream home on the water is ready to welcome you home.

31490 Ave F Unit Avenue F, Big Pine
$950,000
3 Beds ⋅ 2 Baths ⋅ 619875 MLS
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 of a secret garden. Set on an oversized, gated and partially fenced parcel spanning over a quarter acre, this rare non-waterfront property offers the kind of lush green space that's nearly impossible to find in the Florida Keys. Towering old-growth foliage, vibrant established plantings, fresh new landscaping, and newly laid sod create a private, enchanted oasis where every corner invites you to slow down and stay awhile. Built in 1981 of solid concrete block construction and elevated on slab, this beautifully reimagined 3-bedroom, 2-bathroom home offers 1,548 square feet of airy, light-filled living space with bright neutral finishes and thoughtful details throughout. Every inch has been meticulously renovated, blending modern comfort with effortless island charm. Designed to embrace indoor-outdoor living, the property features multiple lanais and entertaining spaces perfect for morning coffee beneath the palms, sunset dinners with friends, or quiet afternoons surrounded by tropical serenity. The expansive lot offers endless opportunity for future enhancements -- envision a resort-style pool and tiki hut, a greenhouse, outdoor kitchen, play space for the kids, or all of the above. There's room here to truly create your dream Keys compound. Downstairs, nearly 400 additional square feet of enclosed storage and utility space adds incredible flexibility, while the paved 3-car carport with lighting and built-in workspace could easily be transformed into the ultimate outdoor entertaining kitchen or hobby space. Beloved Sugarloaf Shores provides peaceful island living with a scenic miles-long paved path, a laid-back Lower Keys atmosphere, and sought-after school district -- all just 15 minutes from exciting Key West. Rare Keys privacy, greenery, and possibility you may never want to leave.

123 Venetian Way, Sugarloaf
$950,000
3 Beds ⋅ 2 Baths ⋅ 619269 MLS
This move-in ready property offers the perfect blend of comfort, functionality, and island charm. Thoughtfully updated, the home features durable vinyl flooring throughout and energy-efficient mini-split systems in every room, providing individualized climate control and lower utility costs. The spacious layout is ideal for both full-time living and investment potential. A private driveway offers convenient off-street parking, while the fully fenced backyard creates a private outdoor retreat--perfect for entertaining, relaxing, or accommodating pets. Additional highlights include in-unit laundry and a clean, modern interior that makes this home truly turnkey. Located in a desirable New Town neighborhood, you're just minutes from shopping, dining, schools, and all that Key West has to offer. Whether you're looking for a primary residence, second home, or investment opportunity, 3700 Northside Drive checks all the boxes.

3700 Northside Dr, Key West
$950,000
3 Beds ⋅ 2 Baths ⋅ 617590 MLS
Hard to find a home in a Park like setting with a boat ramp right out the back door! 3 bedrooms 2 full baths and open living space. Summerland key cove is just 25 miles from Key West. Great place to raise a family or to retire. Be it you're a boater, pilot, fisherman or just want the open space to walk and enjoy privacy of the park. This quit Island neighborhood offers rare access to the laid-back Florida Keys. There is a possibility of being able to convert the lower level into an in-law apartment. This home has deeded reserved exclusive rights to the Park, Boat ramp and Pond PLEASE NOTE! OWNER FINANCING POSSIBLE!

24840 Park Dr, Summerland
$949,000
3 Beds ⋅ 2 Baths ⋅ 620535 MLS
Welcome to 342 Spanish Main Drive, a beautiful canal-front home in the heart of Cudjoe Key, offering the perfect combination of waterfront living, modern comfort, and laid-back Florida Keys charm. This two-story residence features 3 bedrooms and 2 full bathrooms, thoughtfully designed for both everyday living and relaxing island escapes. The bright, open interior is move-in ready and includes a stylish eat-in kitchen with stainless-steel appliances, comfortable living spaces, and plenty of natural light throughout. Enjoy the Florida Keys lifestyle from the spacious covered porches on both levels, where you can sip your morning coffee, unwind with an evening cocktail, or simply take in the peaceful canal views. Large sliding glass doors open to the upper porch, creating a seamless indoor-outdoor living experience that's perfect for entertaining family and friends. Boaters will appreciate the canal-front location with dockage directly behind the home, offering plenty of space for your boat and easy access to both the Gulf and Atlantic. Spend your days fishing, diving, exploring sandbars, or cruising the beautiful Lower Keys waters right from your backyard. Additional features include two garages--a rare find in the Keys--along with ample parking for vehicles, trailers, and guests. Conveniently located just 30 minutes from Key West and within walking distance of the iconic Square Grouper Bar & Grill, this property offers the ideal balance of tranquility and accessibility. 342 Spanish Main Drive is an exceptional opportunity as a full-time residence, vacation home, or waterfront investment property. Come experience the boating lifestyle and island living you've been dreaming about.

342 Spanish Main Dr, Cudjoe
$949,000
3 Beds ⋅ 2 Baths ⋅ 620276 MLS
Discover the laid-back waterfront lifestyle you've been dreaming of at this charming canal-front home in Breezeswept Beach Estates on Ramrod Key. Perfectly situated with water on 2 sides this property offers 150' of waterfront including a deep water basin, excellent dockage and easy access for boating, fishing, kayaking, or paddle boarding right from your backyard. Offering a flexible floor plan with separate living spaces on each level, this property is ideal as a full-time residence, vacation getaway, or investment opportunity. Upstairs, you'll be welcomed into a bright and inviting Great Room that serves as the heart of the home, with sliding doors leading to a screened lanai overlooking the canal where you can enjoy the island breezes. The functional kitchen offers plenty of space for everyday living and effortless entertaining, while the spacious primary bedroom and full bathroom provide a comfortable retreat. Downstairs offers two additional bedrooms, a full bath, laundry room, and a separate living area, providing plenty of space for guests or extended family. Storm ready with CBS construction, impact windows and doors and metal roof. Outdoor living takes center stage with an expansive yard and outdoor shed for convenient storage for all your boating and fishing gear. With quick ocean access from the canal, boaters can be on the water in no time, enjoying world-class fishing diving, Looe Key and endless adventures throughout the Florida Keys. Conveniently located on Ramrod Key, home to two popular outdoor restaurants with live entertainment, miniature golf and convenience store just a quick bike ride away, marina with boat ramp, and just a short drive from Key West, this waterfront retreat captures everything people love about life in the Florida Keys.

27358 Jamaica Ln, Ramrod
$949,000
2 Beds ⋅ 2 Baths ⋅ 620242 MLS
Welcome to this bright and modern 2-bedroom, 2-bath home located in the desirable Breezeswept Beach Estates on Ramrod Key. Completed in 2024 by the builder with high-quality features including a metal roof, impact windows, new A/C, and durable Hardi board siding. This home was later purchased and further upgraded by the current owner, who is also the first to live in the home. Since purchasing, the owner has thoughtfully renovated the kitchen and bathrooms, added custom closets, and installed a fully fenced backyard that creates a private, cozy outdoor space perfect for relaxing or entertaining. Enjoy peaceful sunset views over the salt ponds with no neighbors across the street with open sky and quiet surroundings. The property also features easy access to open water, no bridges to navigate, making it ideal for boating, sunset cruises, or trips to nearby waterfront restaurants. Located on Ramrod Key, you're close to dining, shopping, and grocery stores, all while enjoying the laid-back lifestyle of one of the Lower Keys' most loved neighborhoods. This move-in ready home blends quality construction with stylish upgrades and unbeatable access to the best of island living.

273 Indies Rd, Ramrod
$949,000
3 Beds ⋅ 2 Baths ⋅ 619680 MLS
Where boating lifestyle and modern coastal design align, this fully renovated 3-bedroom, 2-bathroom home in Cudjoe Key delivers exceptional waterfront living. This completely reimagined residence is ideally positioned on a premier corner canal lot, offering approximately 190 feet of concrete seawall and dockage along two waterways, an exceptional setting for boating and waterfront enjoyment. Thoughtfully renovated throughout, the home showcases a clean coastal-modern design with new impact windows and doors, an elevated interior finish, and a beautifully updated kitchen featuring sleek cabinetry, premium surfaces, and an open layout ideal for entertaining. Light-filled living spaces flow seamlessly onto the newly replaced covered rear porch, where tranquil canal views create the perfect backdrop for relaxed indoor/outdoor living. The exterior stairs have also been recently replaced, complementing the home's refreshed and well-maintained feel. Boating enthusiasts will appreciate the 10,000 lb boat lift, expansive seawall/dockage, and quick access to open water via Cudjoe Bay. Downstairs, a large enclosure provides abundant storage space for tools, fishing gear, and boating equipment, an invaluable feature for Keys living. Located on a quiet street in an established neighborhood, this property offers a rare combination of modern updates and generous waterfront in the Lower Florida Keys.

22953 John Silver Ln, Cudjoe
$949,000
3 Beds ⋅ 3 Baths ⋅ 618708 MLS
Unique opportunity to renovate this historic Old Town eyebrow home on a quiet, one-way, block of Elizabeth Street. Situated on a 3038 Sq.ft. lot there is ample space for off-street parking, a pool and 5 bedrooms with a renovation. Please note that advanced notice is required to arrange showings.

818 Elizabeth St Unit Front, Key West