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101201 Overseas Hwy, Key Largo
$1,295,000
616397 MLS
Looking for the perfect commercial building lot opportunity, this is it. Why wait years dealing with Monroe County, when the owner has already spent over two years working with Monroe County to get this far, an approved site plan for a 2,500 sq. ft. commercial building. There are multiple uses for this property. ZONING -SUBURBAN COMMERCIAL.. F.L.U.M. -MIXED USE/COMMERCIAL You can build and run almost any business you want here of course with Monroe County approval. The Seller is submitting the building plans to engineering then to Monroe County to keep the process moving forward to get the building permit. This is the perfect location to run a new or existing business from Key Largo to Key West. Do not miss this opportunity!!!! This commercial property is located across the street from Friendship Park and next to Tradewinds Shopping Center. YOU cannot beat this location!!!

101201 Overseas Hwy, Key Largo

29678 Enterprise Ave, Big Pine
$1,295,000
4 Beds ⋅ 2 Baths ⋅ 617564 MLS
Discover an outstanding opportunity in Big Pine Key with this canal-front, stilted duplex featuring two spacious 2 bedroom 1 bath residences and deep-water boating access. This is an exceptional boater's duplex in Pine Channel Estates where you can enjoy income and lifestyle in one place. Enjoy 75 feet of concrete dockage with a convenient step-down and retaining wall, all situated on a clean, wide canal that delivers you to the ocean or the bay within minutes. Recent upgrades include a brand-new metal roof for peace of mind. One unit has been beautifully updated with modern finishes, while the second unit is rented annually—ideal for buyers looking to live in one home and generate immediate income from the other. Solid construction, excellent water quality, and a prime location in one of the most desirable boating neighborhoods in the Lower Keys make this property truly stand out. Come see for yourself!

29678 Enterprise Ave, Big Pine

702 Florida St, Key West
$1,290,000
2 Beds ⋅ 2 Baths ⋅ 622047 MLS
Where Island Charm Meets Tranquility Tucked away in the highly sought-after Meadows neighborhood, this charming Key West retreat offers the perfect blend of privacy, tropical beauty, and indoor-outdoor living. Situated on an oversized corner lot, this 2-bedroom, 2-bathroom home is surrounded by lush tropical landscaping, creating a peaceful oasis in one of Key West's most desirable and quiet neighborhoods. Designed to embrace the island lifestyle, the home features a spacious, private primary suite and generously sized second bedroom. Each of the bedrooms have access to their own outdoor sitting area. A large screened-in patio extends from the living room, offering the perfect setting for entertaining, relaxing, or simply enjoying views of the beautiful tropical garden. Additional highlights include a new roof, off-street parking, and a covered carport--valuable conveniences in the heart of Key West. With its generous lot size, multiple outdoor living spaces, and sought-after Meadows location, 702 Florida Street presents a rare opportunity to enjoy the best of island living in a truly tranquil setting.

702 Florida St, Key West

251 Azalea St, Tavernier
$1,290,000
2 Beds ⋅ 2 Baths ⋅ 621754 MLS
Unpack, launch the boat, and start living the Keys life. This turnkey, ground-level concrete canal home in Plantation Key Colony is ready for you. The big projects are done: a brand new metal roof, impact windows and doors, a new sewer line, fresh paint inside and out, new interior doors, and energy-efficient appliances. Even the tiki hut was just re-thatched. The 2 bed, 2 bath home is clean, bright and easy to care for. The boating setup is hard to beat. You have 50 ft of dockage on the canal and a boat slip with a ramp that runs through the pull-through garage. A new fish cleaning station with water and electric is ready for the day's catch. Run out Tavernier Creek to the ocean side, or head straight into Florida Bay. The garage has been refreshed too, with new door rollers, new lock hardware, and upgraded floors and walls. Plantation Key Colony has a voluntary HOA and a bayfront park with a boat ramp, a small beach and a picnic area. Islamorada's marinas, waterfront restaurants and world-class fishing are just minutes away!

251 Azalea St, Tavernier

11250 5th Avenue Gulf Ave, Marathon
$1,290,000
5 Beds ⋅ 3 Baths ⋅ 616064 MLS
FLORIDA KEYS WATERFRONT VALUE 5 BEDROOMS • DIRECT GULF ACCESS • TWO-STORY LAYOUT Located in Marathon, this spacious two-story waterfront property has direct Gulf access, flexible living space, and future rooftop deck potential with possible bay views from upper-level enhancements. The home is functional and move-in ready, with prior updates already completed and major systems operational. Natural light, multiple living areas, and the flexible layout provide opportunities for full-time living, seasonal use, guest space, boating lifestyle, or future personalization over time. Expansive outdoor deck space and waterfront positioning create room to enjoy boating, fishing, water activities, and relaxed Florida Keys living. The property layout also allows flexibility for future outdoor enhancements, tropical landscaping, shaded entertaining areas, or additional outdoor living concepts. With l waterfront inventory in the Florida Keys, this property presents a chance to secure a larger waterfront home in Marathon with long-term flexibility and future potential. Property is being sold as it is, allowing the next owner flexibility to personalize and update over time.

11250 5th Avenue Gulf Ave, Marathon

174 Tortuga Ln, Cudjoe
$1,270,000
3 Beds ⋅ 2 Baths ⋅ 620186 MLS
Florida Keys Living at Its Best! Welcome to 174 Tortuga Lane, a beautifully maintained waterfront home in the heart of Cudjoe Key, where world-class fishing, boating, and island living are in your backyard. With 37 feet of dockage, you'll have quick access to the Atlantic, backcountry waters, and some of the best fishing the Florida Keys has to offer. Built in 2020 for peace of mind and low-maintenance ownership, this 3-bedroom, 2-bath home features impact windows and doors, HardiePlank siding, Trex decking, aluminum railings, and a 180-mph wind rating. Inside, you'll find a bright, coastal-inspired interior with 9-foot ceilings, luxury vinyl plank flooring, an open-concept living area, spacious eat-in kitchen, pantry, separate laundry room, and a comfortable primary suite with walk-in closet and oversized bath. The fabulous outdoor space is where this property shines. Since the home was built, a stunning concrete pool was added in 2022, creating the perfect place to cool off after a day on the water. Relax under the new tiki hut, rinse off in the outdoor shower, challenge friends and family on the putting green, or simply enjoy the constant ocean breezes and beautiful open water views across the street. The oversized fenced lot offers plenty of room to spread out, while the covered front porch and legal downstairs storage provide additional functionality. There's even 50-amp service for an RV or electric vehicle charger. Whether you're looking for a full-time residence, vacation home, or Keys getaway, 174 Tortuga Lane delivers the boating lifestyle, outdoor amenities, and island charm that make the Florida Keys so special. *Boat lift to be installed with list price offer*

174 Tortuga Ln, Cudjoe

30851 Baileys Ln, Big Pine
$1,260,000
3 Beds ⋅ 2 Baths ⋅ 621133 MLS
Built in 2024 and ready for island living! Welcome to 30851 Baileys Lane, a beautifully designed 3-bedroom, 2-bath waterfront home offering 1,120 sq. ft. of modern coastal living in the heart of Big Pine Key. Bright, open and inviting, the home features a thoughtfully designed floor plan filled with natural light and an easy indoor-outdoor flow. Step outside and enjoy the lifestyle people come to the Florida Keys for--boating, fishing, kayaking and relaxing by the water, all right from your own piece of paradise. The elevated design provides valuable covered space below for parking, storage, boats and all your Keys toys. Built in 2024, this home offers the advantage of newer construction so you can spend more time enjoying the islands and less time worrying about maintenance. Tucked away in the laid-back surroundings of Big Pine Key, yet conveniently located between Key West and Marathon, this is an ideal full-time residence, weekend getaway or Florida Keys retreat. Newer construction. Waterfront living. Your Keys lifestyle starts here.

30851 Baileys Ln, Big Pine

1422 Boca Chica Rd, Geiger
$1,259,000
3 Beds ⋅ 2 Baths ⋅ 621454 MLS
A Private Waterfront Sanctuary on Geiger Key, AKA ''The Backside of Paradise''. *** Just 15 minutes from Key West, this extraordinary waterfront retreat offers something almost unheard of in the Florida Keys: Privacy and unobstructed open water views with not a neighboring home in sight. *** Surrounded by acres of Government-owned sanctuary land, the setting delivers a rare sense of seclusion--like owning your own private island, without the island price. *** This extensively renovated 3BD/2BA home features a refined Zen Contemporary / Tropical Modern design with a NEW: roof, impact windows and doors, A/C, siding, decks, and beautifully updated interiors--all built to meet or exceed current storm-resilient standards. *** The open-concept living, dining, and chef's kitchen are designed for entertaining, with quartz countertops, contemporary cabinetry, and a wet bar with dual wine coolers. The primary suite is wrapped in windows overlooking a tranquil private lagoon--your own natural swimming retreat. *** Outdoor living shines with expansive decks offering space for dining, lounging, and a gas firepit and BBQ area (w gas lines). Enjoy a large dock/deck and a heated pool (swim spa with swimming jets) for a year-round resort experience. *** Enjoy shallow draft boating access (vessels up to ~20-22 ft are best) from the backyard canal, along with close proximity to the Big Coppitt boat ramp for convenient deep-water navigability., *** Additional features include a full-footprint storage level, + a 1.5-car garage, ample parking, and RV storage with hook-ups. Insurance is favorable at approx. $8,500/year. *** A rare opportunity at this price point--where most homes offer only canal views and close neighbors--this property delivers unmatched privacy, views, and lifestyle. Seller is a Florida Licensed Realtor.

1422 Boca Chica Rd, Geiger

96000 Overseas Hwy Unit B8, Key Largo
$1,250,000
2 Beds ⋅ 3 Baths ⋅ 622018 MLS
Beautifully renovated and impeccably appointed, this 2-bedroom, 2.5-bath townhome is ideally situated within the prestigious Buttonwood Bay Club, just steps from the clubhouse, pools, and resort-style amenities. The 36-foot boat slip is one of the largest available and is conveniently located directly behind the residence. The interior showcases elegant coastal finishes, custom built-ins, and a thoughtfully designed gourmet kitchen featuring expansive white quartz countertops, premium stainless steel appliances, classic white backsplash, and timeless cabinetry. Additional features include electric blinds, impact-rated windows and doors, and an electric patio awning that creates the perfect shaded retreat for outdoor relaxation. At the heart of Buttonwood Bay is an exceptional deep-water marina with outstanding boating amenities, including an on-site Ship's Store offering provisions, bait, ice, and fuel, as well as a boat ramp and designated trailer parking. This gated, 24-hour secured community offers an unparalleled resort lifestyle with 12 pickleball courts, tennis courts, three heated and chilled swimming pools, a state-of-the-art fitness center overlooking the marina, saunas, basketball court, and an elegant clubhouse with a full kitchen for entertaining. Eight waterfront martini docks provide the perfect setting for sunset gatherings, while a sandy beach completes the quintessential Florida Keys experience. Buttonwood Bay is more than a place to call home, it's a lifestyle defined by waterfront living, exceptional amenities, natural beauty, and effortless coastal luxury.

96000 Overseas Hwy Unit B8, Key Largo

189 Carroll St, Islamorada
$1,250,000
3 Beds ⋅ 3 Baths ⋅ 621912 MLS
Newly Remodeled 3-Bed, 3-Bath Home in the Heart of Islamorada This beautifully remodeled 3-bedroom, 3-bath home is located on Upper Matecumbe in the heart of Islamorada, offering the perfect combination of luxury, comfort, and island style--all on one level. The open-concept floor plan features a spacious living area ideal for entertaining, a modern kitchen with stainless steel appliances and granite countertops, and three generous bedrooms each with its own bathroom. Built with solid concrete construction, impact windows, and elevated above flood, this home provides durability and peace of mind. Enjoy modern finishes throughout and a large outdoor deck perfect for relaxing or hosting gatherings. Situated on a quiet street with beach access at the end of the road, this home offers both convenience and tranquility. Close to world-class dining, shopping, and some of the best fishing and diving in the Florida Keys. Excellent rental potential--buy one or both adjoining homes for added investment opportunity. 'The adjacent residence offers a rare opportunity to expand into a multi-residence estate or income-producing property.' 'The neighboring home may be acquired to create an exceptional multi-home setting ideal for extended family living or rental income.' 'Purchasing the nearby residence allows for a flexible use property, suitable for private family living or investment purposes.' 'The adjoining property presents a unique opportunity to establish a private multi-home arrangement or enhance rental potential.' 'With the option to acquire the neighboring home, buyers can create a distinctive residential setting with income potential.'Buy both homes and get a $25,000 reduction. Rental Available longterm $6,000 per month

189 Carroll St, Islamorada

191 E Carroll St, Islamorada
$1,250,000
3 Beds ⋅ 3 Baths ⋅ 621911 MLS
Newly Remodeled 3-Bed, 3-Bath Home in the Heart of Islamorada This newly remodeled 3-bedroom, 3-bath home is located on Upper Matecumbe in the heart of Islamorada, offering the perfect blend of modern comfort and island living. The unique layout features 1 bedroom and 1 bathroom downstairs, and 2 bedrooms and 2 bathrooms upstairs--ideal for guests or extended family. Built with solid concrete construction and impact windows, this home is elevated above flood and designed for peace of mind. Inside, enjoy an open-concept living area perfect for entertaining, a spacious kitchen with stainless steel appliances and granite countertops, and bright, generously sized bedrooms. Modern finishes and high-quality craftsmanship shine throughout. Step outside to a large deck perfect for soaking up the Florida Keys sunshine. Located on a quiet street with beach access at the end of the road, this property offers convenience and tranquility. Close to world-class restaurants, shops, and some of the best fishing and diving in the world. Excellent rental potential--buy one or both adjoining homes for added opportunity. 'The adjacent residence offers a rare opportunity to expand into a multi-residence estate or income-producing property.' 'The neighboring home may be acquired to create an exceptional multi-home setting ideal for extended family living or rental income.' 'Purchasing the nearby residence allows for a flexible use property, suitable for private family living or investment purposes.' 'The adjoining property presents a unique opportunity to establish a private multi-home arrangement or enhance rental potential.' 'With the option to acquire the neighboring home, buyers can create a distinctive residential setting with income potential. Buy both homes and get a $25,000 reduction. Home currently leased for 1 yr.

191 E Carroll St, Islamorada

94825 Overseas Highway Unit 51, Key Largo
$1,250,000
3 Beds ⋅ 2 Baths ⋅ 621730 MLS
Exceptional quality and superior craftsmanship are evident throughout this beautifully appointed 2023-built residence in Key Largo Ocean Resort. Offering 1,800 square feet of living space, this three-bedroom, two-bath home features concrete block construction, a metal roof, and an elevated design with covered parking and ground-level storage. The interior showcases upscale contemporary finishes, including solid wood cabinetry, elegant granite backsplashes, high-end stainless steel appliances, and a built-in undercounter microwave. Thoughtfully designed architectural lighting includes integrated ambient lighting within the cabinetry and walls, along with illuminated stairways that enhance the home's modern appeal. Upgraded electrical fixtures and a Siemens electrical panel complement the home's quality construction. Additional features include ceramic tile flooring, an upper-level porch, and a finished ground-level utility/storage area. Residents of Key Largo Ocean Resort enjoy community amenities, including a boat ramp, community center, swimming pool, and playground, offering opportunities for boating, recreation, and relaxation. Built with attention to detail, this residence combines quality materials, modern design, and functional living spaces with the enjoyment of the Florida Keys lifestyle.

94825 Overseas Highway Unit 51, Key Largo

124 Peace Ave, Tavernier
$1,250,000
4 Beds ⋅ 3 Baths ⋅ 621320 MLS
Brand New Home under Construction. 4 bedrooms 3 bath 2256 Sq Ft. Be the 1st to live here. Make this your Dream Home in The Keys. Elevated Tri-level home with storage and carport below. Main living level on the 2nd floor with an open great room, kitchen and1 guest bedroom and bath. Continue to the 3rd floor for an additional 2 guest bedrooms and bath plus Primary suite and bath. Construction features include Cistern, Solar Panels. A Tavernier location between Key Largo and Islamorada that puts the Florida Keys lifestyle at your fingertips. Set in the established Dove Creek neighborhood offers the freedom of a single-family home with no mandatory HOA, while keeping you close to boating, fishing, diving, waterfront dining and all the attractions of Key Largo, Tavernier and Islamorada. Enjoy the Keys lifestyle without the waterfront price tag, then come home to a brand-new residence designed for today's island living. Close to Snappers Restaurant, Boat ramp and beach in nearby Mike Forster Park, Harry Harris and John Pennekamp. 'NEW CONSTRUCTION. KEYS LIFESTYLE. NO HOA.'

124 Peace Ave, Tavernier

405 Coconut Dr, Key Largo
$1,250,000
4 Beds ⋅ 3 Baths ⋅ 621319 MLS
Brand New Dream Home Under Construction! 4 bedroom 3 bath home with 2256 sq ft. Elevated Ground Level with 1st floor open great room, kitchen and 1 guest bedroom and bath. Continue to interior stairs to the 2nd floor for an additional 2 guest bedrooms and bath plus Primary suite and bath. Construction features include Cistern, Solar Panels. A Key Largo location that puts the Florida Keys lifestyle at your fingertips. Set in the established Seaside neighborhood around Mile Marker 94.5, 405 Coconut Drive offers the freedom of a single-family home with no mandatory HOA, while keeping you close to boating, fishing, diving, waterfront dining and all the attractions of Key Largo, Tavernier and Islamorada. Enjoy the Keys lifestyle without the waterfront price tag, then come home to a brand-new residence designed for today's island living. Close to Snappers Restaurant, Boat ramp and beach in nearby Mike Forster Memorial Park, Harry Harris and John Pennekamp. 'NEW CONSTRUCTION. KEYS LIFESTYLE. NO HOA.'

405 Coconut Dr, Key Largo

96 Ave C, Marathon
$1,250,000
2 Beds ⋅ 3 Baths ⋅ 621219 MLS
Bonefish Yacht Club Townhomes, a Middle Keys premiere boating community cloistered around the 50 slip Bonefish Marina. Resort style living in this sought after oceanfront complex of only 34 homes. This unit can conveys with A-16, a deep water, direct ocean access, 40' liveaboard boat slip. Buyer approval for the boat slip will be required through Bonefish Marina. Other amenities featured are; swimming pool, tiki, meticulously maintained tropical landscaping, tennis and private beach access. Unparalleled views of the marina and Key Colony Channel. Two story townhome with covered parking and secure angler's room on the lower level, kitchen, living, dining on the main level and two spacious bedrooms with full baths on the third floor. Private, open air balconies to enjoy both sunrise and sunset. Concrete construction, impact windows and metal roof. Excellent for a full time residence, Keys fishing getaway or investment property as a income producing weekly rental. A true pleasure to show.

96 Ave C, Marathon

182 Airstream Ln, Tavernier
$1,250,000
2 Beds ⋅ 2 Baths ⋅ 620396 MLS
Welcome to stunning Florida Bay views and breathtaking sunsets in the heart of Plantation Key! This beautifully remodeled and fully furnished modular home offers the perfect blend of comfort, style, and waterfront living. Featuring two spacious bedrooms, two bathrooms and an open-concept living area and kitchen, the home is thoughtfully designed with a light and airy coastal flair throughout. You will appreciate the huge amount of storage downstairs. Step outside to your inviting waterfront patio, where you can relax and take in beautiful open water views. Boaters will appreciate the 45' of concrete dockage and new 16K lb. boat lift, providing effortless access to Florida Bay and nearby Atlantic Ocean access through Snake Creek. Spend your days exploring the Keys by boat, enjoying waterfront dining, world-class fishing and diving. Founder's Park nearby for boat ramp, beach, pool and ball fields. Whether you're looking for a full-time residence, vacation retreat, or investment opportunity, this turnkey waterfront property represents the laid-back Florida Keys lifestyle. Come experience the beauty, boating, and unforgettable sunsets that make Plantation Key one of the most desirable locations in the Florida Keys.

182 Airstream Ln, Tavernier

466 W Shore Dr, Summerland
$1,250,000
2 Beds ⋅ 2 Baths ⋅ 620321 MLS
DOUBLE the Lot. DOUBLE the Waterfront. Endless Possibilities. Positioned on a rare spacious double lot near the Summerland Key airport, this waterfront property is tailor-made for boating enthusiasts and aviation lovers alike. Featuring 120 feet of concrete seawall on a desirable flow-through canal, you'll enjoy quick access to open water and some of the Lower Keys' best fishing, diving, and cruising grounds. Afterwards, sit under the tiki and watch the world go by. The ground-level home exhibits a Keys charm with polished terrazzo floors and a relaxed, welcoming feel. Outside, ample parking provides room for boats, trailers, RVs, and guests. Inside, a unique electric train display serves as a nod to the historic Overseas Railroad that once connected the Keys. A rare opportunity to enjoy the classic Florida Keys lifestyle with room to spread out, easy boating access, and the convenience of nearby aviation amenities. Bring your big boats to this deep water canal - no bridges to the Atlantic Ocean. Plane tie downs are located in the driveway. For additional airport info - see summerlandkeyairport.com. Ask about the assumable VA loan.

466 W Shore Dr, Summerland

5 Stillwright Way, Key Largo
$1,250,000
620304 MLS
ACTIVE BUILDING PERMIT IN HAND! Don't miss this rare opportunity to build your waterfront dream home in the highly desirable Stillwright Point community of Key Largo. This spacious 50' x 150' waterfront lot is ideally situated on a wide 70' canal and offers deep-water dockage with immediate access to Florida Bay. Boaters will appreciate the quick and convenient access to the Atlantic Ocean through nearby Adams Cut, providing the best of both worlds for offshore and backcountry adventures. Whether you're envisioning a luxury waterfront retreat or a full-time residence, this property is ready for your vision with an active building permit already in place. Enjoy the laid-back Florida Keys lifestyle with world-class fishing, diving, boating, waterfront dining, and breathtaking sunsets right at your doorstep. Build now and start living the Keys dream in one of Key Largo's most sought-after waterfront neighborhoods.

5 Stillwright Way, Key Largo

1911 Seidenberg Ave, Key West
$1,250,000
2 Beds ⋅ 2 Baths ⋅ 620075 MLS
With only two owners in its history, this well-maintained two-story property presents a rare investment opportunity in Key West. Configured as a legal duplex with two separately metered 1-bedroom, 1-bath units, it offers exceptional flexibility--ideal for investors seeking strong rental potential, business owners looking for employee housing, or owner-occupants wanting to offset costs by renting one unit while living in the other. Set on a 5,000 sq ft lot, the property is surrounded by lush, mature tropical landscaping with a wide variety of plants and palms, creating a private, shaded, treehouse-like setting filled with natural light. Two large screened porches and additional open-air spaces provide ideal indoor-outdoor living, while an outdoor shower enhances the island lifestyle. The home has been thoughtfully updated and well cared for, featuring Mitsubishi mini-split A/C systems in both units, a new hot water heater, new ceiling fans, impact windows upstairs, new gutters, updated appliances, and soft-close cabinetry. Interior finishes include a mix of pine, vinyl, and concrete flooring, along with stainless, Formica, and butcher block countertops. Both units offer full bathrooms with tubs. Additional highlights include two off-street parking spaces, low-maintenance grounds, and multiple windows throughout for abundant natural light and airflow. Located in desirable Midtown East, just minutes from everything Key West has to offer, this is a versatile, income-producing property with strong upside potential.

1911 Seidenberg Ave, Key West

4049 Egret Ln, Big Torch
$1,250,000
5 Beds ⋅ 5 Baths ⋅ 619914 MLS
Waterfront living meets comfort and functionality in this move-in ready canal front home. Offering 120 feet of concrete dockage in a deep water canal. Quick boating access to Niles Channel. Designed for the ultimate Florida Keys lifestyle, this property combines spacious indoor living with exceptional outdoor entertaining areas. The main home features 2 bedrooms and 2 bathrooms with an open-concept floor plan ideal for entertaining. The modern kitchen is equipped with quartz countertops, stainless steel appliances, and plenty of space for gathering with family and friends. An additional guest wing offers 3 separate bedrooms, each with its own ensuite bathroom, providing privacy and flexibility for guests or extended family. Enjoy seamless indoor-outdoor living from the large screened-in porch breezeway -- the perfect place for morning coffee, evening dinners, or relaxation. Outside, the concrete swimming pool creates a true tropical retreat, while the spacious outdoor areas offer plenty of room for entertaining. The ground level includes an expansive enclosed garage with room for multiple vehicles, storage, and all your boating and fishing gear. The fully fenced property offers abundant parking for cars, boats, RVs, and trailers, making it ideal for full-time living or a Keys getaway. Located in a quiet neighborhood, this property delivers the best of waterfront living with easy boating access, generous space, and move-in ready convenience.

4049 Egret Ln, Big Torch

1911 Seidenberg Ave, Key West
$1,250,000
2 Beds ⋅ 2 Baths ⋅ 619758 MLS
With only two owners in its history, this well-maintained two-story property presents a rare investment opportunity in Key West. Configured as a legal duplex with two separately metered 1-bedroom, 1-bath units, it offers exceptional flexibility--ideal for investors seeking strong rental potential, business owners looking for employee housing, or owner-occupants wanting to offset costs by renting one unit while living in the other. Set on a 5,000 sq ft lot, the property is surrounded by lush, mature tropical landscaping with a wide variety of plants and palms, creating a private, shaded, treehouse-like setting filled with natural light. Two large screened porches and additional open-air spaces provide ideal indoor-outdoor living, while an outdoor shower enhances the island lifestyle. The home has been thoughtfully updated and well cared for, featuring Mitsubishi mini-split A/C systems in both units, a new hot water heater, new ceiling fans, impact windows upstairs, new gutters, updated appliances, and soft-close cabinetry. Interior finishes include a mix of pine, vinyl, and concrete flooring, along with stainless, Formica, and butcher block countertops. Both units offer full bathrooms with tubs. Additional highlights include two off-street parking spaces, low-maintenance grounds, and multiple windows throughout for abundant natural light and airflow. Located in desirable Midtown East, just minutes from everything Key West has to offer, this is a versatile, income-producing property with strong upside potential.

1911 Seidenberg Ave, Key West

1401 Simonton St Unit # 11, Key West
$1,250,000
2 Beds ⋅ 2 Baths ⋅ 619022 MLS
This two-bedroom, two-bathroom condominium residence at Santa Maria Suites Resort offers both personal use and strong rental income potential. One of the resort's limited single-level units, the property produces nearly $200,000 in annual gross rental income and allows for transient nightly rentals. The floor plan features a generous living and dining area, full kitchen, and two private bedroom suites. Located just steps from iconic Duval Street, the property provides convenient access to Old Town restaurants, shops, and nightlife while maintaining a quiet resort setting. Resort amenities include swimming pool, fitness center, and off-street parking. Planned improvements to the residences, pool, and fitness areas are scheduled for completion in 2027. The current owner has paid the majority of the special assessment associated with these upgrades. Owners may choose their own rental management company or participate in the on-site program. Suitable for buyers seeking an income-producing investment, second home, or a combination of both.

1401 Simonton St Unit # 11, Key West

96000 Overseas Hwy Unit U9, Key Largo
$1,250,000
2 Beds ⋅ 3 Baths ⋅ 617633 MLS
Discover the ultimate in waterfront living at Buttonwood Bay in south Key Largo--a gated, resort-style community built around a deep-water coral rock harbor with direct Florida Bay access.This beautifully remodeled residence includes a 36' boat slip right outside your back door, making it effortless to enjoy the best of Keys boating and fishing. Beautiful corner unit fully remodeled in 2022. New bathrooms, kitchen, plumbing, electrical, and flooring. Sliding doors added to the North side for extra brite downstairs. Instant hot water heater and washer dryer in unit. There's also a sandy beach, boat ramp, trailer storage, Ship's Store with fuel, bait, ice, and snacks--everything a boater needs, right at home. With on-site management, dedicated maintenance, and 24/7 security, you can relax knowing every detail is taken care of

96000 Overseas Hwy Unit U9, Key Largo

27001 Overseas Hwy, Ramrod
$1,250,000
1 Beds ⋅ 3 Baths ⋅ 618580 MLS
Prime Lower Keys Commercial Property for sale on Ramrod Key. 3 Lots total 28,132 sf. or .65 acres with nearly 189' of frontage on Overseas Hwy aka Jimmy Buffett Memorial Hwy.!! Excellent visibility from the highway going both North and Southbound. This is a Corner lot at Coral Ave and Overseas Hwy with additional rear access off Old State Rd. 4A. Three sides with roads give this property ample room for ingress and egress for cars, large trucks and big equipment. Many commercial uses allowed with favorable SC- Suburban Commercial zoning. Perfect for Contractor or many retail uses possible including Marine/Boat/Trailer/RV or Boat dealer, Convenience store, or historically used for a Landscaping business. Lot is completely fenced and many parking spaces within and around the property. There is a shallow water well on the property that can be used for irrigation. On site is an existing 1,434 sf. CBS building. It can be a demo and completely redeveloped or exisitng building could used for offices and possible residential. Historically a homesteaded property, the ROGO currently not recognized by the County but a determination pending. Plus there is a nicely built Tiki Hut, a storage building with half bath for customers, potting shed and another utility building. There is a limited supply of SC zoned commercial lots in the Lower Keys.

27001 Overseas Hwy, Ramrod

27001 Overseas Hwy, Ramrod
$1,250,000
1 Beds ⋅ 3 Baths ⋅ 618610 MLS
Prime Lower Keys Commercial Property for sale on Ramrod Key. 3 Lots total 28,132 sf. or .65 acres with nearly 189' of frontage on Overseas Hwy aka Jimmy Buffett Memorial Hwy.!! Excellent visibility from the highway going both North and Southbound. This is a Corner lot at Coral Ave and Overseas Hwy with additional rear access off Old State Rd. 4A. Three sides with roads give this property ample room for ingress and egress for cars, large trucks and big equipment. Many commercial uses allowed with favorable SC- Suburban Commercial zoning. Perfect for Contractor or many retail uses possible including Marine/Boat/Trailer/RV or Boat dealer, Convenience store, or historically used for a Landscaping business. Lot is completely fenced and many parking spaces within and around the property. There is a shallow water well on the property that can be used for irrigation. On site is an existing 1,434 sf. CBS building. It can be a demo and completely redeveloped or exisitng building could used for offices and possible residential. Historically a homesteaded property, the ROGO currently not recognized by the County but a determination pending. Plus there is a nicely built Tiki Hut, a storage building with half bath for customers, potting shed and another utility building. There is a limited supply of SC zoned commercial lots in the Lower Keys.

27001 Overseas Hwy, Ramrod

606 Truman Ave Unit APT 1, Key West
$1,249,000
2 Beds ⋅ 2 Baths ⋅ 621668 MLS
A RARE OLD TOWN FIND -- LOCATION, LIFESTYLE & INVESTMENT POTENTIAL! A MUST-SEE for the savvy investor, seasonal resident, or anyone dreaming of owning a piece of the Key West lifestyle! Tucked inside Windward Park, an intimate gated enclave of just 13 townhomes, this 2BD/2BA residence delivers the kind of winning combination that makes Old Town Key West so irresistible: a coveted downtown address, tropical surroundings, and a sense of privacy just one and a half blocks from the energy of Duval Street. World-class dining, lively bars, charming boutiques, and the unmistakable spirit of Key West are all just moments away. Think location, location, LOCATION -- with a tropical twist! Built in the late 1980s, Windward Park is one of the few small gated communities in the heart of Old Town. Beyond the gated entrance, a sparkling community pool and lush tropical gardens create a private oasis that feels worlds away from the bustle outside. Here, you can enjoy the best of both worlds: the excitement of downtown living and a peaceful retreat to call your own. Positioned as the first townhome on the left as you enter the community, this residence welcomes you with a charming front porch overlooking the pool and gardens. Inside, 1,120 square feet of versatile living space offer two bedrooms and two baths, with a layout that accommodates a variety of lifestyles. The ground-floor bedroom opens to its own sunny private patio -- an inviting setting for al fresco dining, entertaining, or enjoying the laid-back island atmosphere. Its convenient downstairs location also offers flexibility for guests or those who prefer a no-stairs bedroom option. THE OPPORTUNITY? 606 Truman deserves a closer look. Its central location, gated setting, community pool, off street parking spot and turnkey offering make it an appealing candidate for buyers looking to combine personal enjoyment and income potential.

606 Truman Ave Unit APT 1, Key West

5 Mccoy Cir Unit # 5, Key West
$1,249,000
2 Beds ⋅ 3 Baths ⋅ 621523 MLS
BOAT SLIP INCLUDED WITH OWNERSHIP! A standout waterfront opportunity in Key West, 5 McCoy Cir #5 offers the coastal lifestyle you've been looking for: a townhome-style residence with a deeded boat slip, unobstructed open water views, ample parking, and direct sightlines to your boat from the balcony. This 1,387 sq. ft. home features a thoughtfully designed three-level layout with generous storage, covered parking, and multiple outdoor living spaces. The main level offers an open kitchen and living area, convenient half bath, and a spacious balcony overlooking the water, your boat slip, and the open horizon beyond. Upstairs, two bedrooms each feature their own ensuite bathroom, offering comfort and privacy. Below, the covered garage provides ample room for boating gear, fishing equipment, bikes, tools, and everything needed for a day on the water. A private patio adds another outdoor space to relax or prepare for your next adventure. The deeded boat slip is a true highlight, comfortably accommodating a 25-foot boat with dual engines. Walk directly to your boat and enjoy effortless access to the water whenever adventure calls! With dedicated parking, abundant storage, breathtaking water views, and HOA coverage that includes insurance and exterior maintenance, this property combines convenience with the ultimate Key West waterfront lifestyle. An added benefit: Flagler's Landing is not subject to Florida's milestone inspection or Structural Integrity Reserve Study (SIRS) requirements. Come see it by land or by boat! Pull up to the slip and we'll give you a tour!

5 Mccoy Cir Unit # 5, Key West

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