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5435 5th Ave, Key West
$735,000
3 Beds ⋅ 3 Baths ⋅ 621643 MLS
Welcome to your dream oasis, perfectly situated directly across from a beautiful park with rare dual-street accessibility. This exceptional property blends spacious design with incredible versatility, featuring a 3-bedroom, 3-bathroom main residence, a fully detached private guest cottage, and entrances from two different streets at the front and back. As you step into the main home, you are immediately greeted by soaring, high ceilings and abundant natural light that amplify the open and airy layout. The floor plan flows effortlessly into the outdoor living spaces, featuring beautifully crafted brick-layered patios--perfect for dining alfresco, entertaining guests, or simply enjoying the peaceful breeze. Security and convenience meet at the rear of the property, which boasts off-street gated parking accessed securely from the back street. The separate backyard cottage provides the ultimate flexibility, making it an ideal space for a private home office, an artist's studio. Combined with the serene park views right out your front door and premium dual-access convenience, this unique property offers the perfect balance of community connection and private retreat.

5435 5th Ave, Key West
811 Olivia St, Key West
$2,250,000
5 Beds ⋅ 4 Baths ⋅ 621640 MLS
Historic Old Town Charm Meets Modern Luxury. Situated next to the iconic Key West Cemetery, this legal duplex sits proudly on the island's highest point, offering an unbeatable location with unmatched peace of mind. With the original Conch House built in the late 1800s, this historic estate captures the classic romance of classic island architecture while providing a passive income opportunity. It is the ultimate configuration for a buyer looking to live the island dream in a beautiful residence while utilizing the separate unit as a legal rental to offset living costs. The main house is a spacious sanctuary featuring 4 bedrooms and 3 bathrooms. Every room blends historic character with modern comfort, offering an airy layout perfect for relaxation or entertainment. Steps away, the independent unit is a beautifully efficient studio apartment. This legal secondary unit serves as a desirable rental asset, an independent guest suite, or a private home office, adding incredible flexibility and value in a market where legal duplexes are highly coveted. While the property retains its rich late-19th-century soul, it also functions with the reliability of new construction. The entire property underwent a meticulous top-to-bottom renovation from 2022 to 2025, modernizing every major component. Upgrades include a new roof (2022), all new plumbing (2024), fully updated electrical systems (2024), attic insulation (2025), and a brand-new HVAC system (2024). Calling this property home means enjoying a quiet backdrop and unique neighborhood charm. You are just a short walk or bike ride away from world-class dining, vibrant nightlife, and pristine beaches. The driveway provides off-street parking for 1 vehicle.

811 Olivia St, Key West
1116 Eaton St, Key West
$889,000
2 Beds ⋅ 1 Baths ⋅ 621609 MLS
Charming Old Town Key West Cottage with Private Pool & Rooftop Deck Welcome to 1116 Eaton Street, Key West, Florida 33040--a charming 2-bedroom, 1-bathroom single-family cottage in the heart of Old Town Key West. This beautifully maintained 749 sq. ft. home combines classic island character with comfortable living and exceptional outdoor spaces, including a private heated pool and rooftop deck. Inside, the efficient floor plan is filled with natural light and features inviting living spaces and two bedrooms positioned for privacy. The kitchen and living area flow naturally together, creating a comfortable setting for everyday living or entertaining. Step outside to enjoy your private pool and multiple outdoor living spaces. The heated pool provides a refreshing place to relax, while the rooftop deck offers an elevated setting for morning coffee, sunset drinks, dining, or entertaining. The location is exceptionally walkable, with convenient access to Duval Street, historic architecture, restaurants, galleries, shopping, nightlife, the Key West Seaport, and other Old Town destinations. Enjoy the privacy of a residential cottage while remaining close to the energy and attractions that make Key West so desirable. Whether you're searching for a full-time residence, second home, or investment property, this **Key West home with a private pool** offers a rare combination of location, outdoor living, and Old Town charm. Highlights: 2 bedrooms | 1 bathroom | 749 sq. ft. | Private heated pool | Rooftop deck | Multiple outdoor living spaces | Single-family home | Highly walkable Old Town location | Under $1 million. Experience the charm and convenience of Old Town Key West at 1116 Eaton Street.

1116 Eaton St, Key West
138 Golf Club Dr, Key West
$580,000
2 Beds ⋅ 2 Baths ⋅ 621596 MLS
VALUE now is even SWEETER! Adjusted Price! Welcome to 138 GC Dr. in the highly sought-after Key West Golf Club residential community. Surrounded by acres of open space, Rees-Jones designed 18-hole Championship Golf Course. INVITING, Ready for Immediate Occupancy, ''Fresh as a Daisy,'' Townhome. Waiting for you! Beautifully maintained home offers the perfect blend of island living, resort-style amenities. Featuring low maintenance ceramic tile downstairs, new Berber carpet upstairs, freshly painted interior/exterior, charming picket fence, abundant natural light, 4 VERANDAS! Ideal for full-time residents, those seeking a relaxing vacation retreat, or utilize your new home intermittently while enjoying 30-day vacation rentals to supplement expenses. Ideal for long-term income producing rental home, as housing demand is great for the hardworking ''locals,'' all while you await retirement. So many options. This home is a short stroll to Golf Pro Shop, Community Center Building w/Fitness Room is just down the lane, a hop-skip-and jump to the beautiful, large lagoon-shaped pool w/tropical waterfalls. There is a real ''spirit of community!'' Peaceful ambiance in end-unit location, providing that extra breathing room. Easy to navigate kitchen has white appliances and Formica countertops. Private outdoor veranda directly off the living room is perfect for entertaining/relaxing. Primary Bedroom has 2 closets and large adjacent private veranda, which overlooks scenic Spoonbill Way. Guest Bedroom has adjacent cozy veranda overlooking the mature tree-lined streetscape w/old fashioned street lanterns. KWGC has gated entry, 24-hr. Resident Serv, 2 fabulous pools, Fitness Rm., Butterfly Garden, so much more. Just minutes from Old Town KW, beaches, marinas, shopping, and vibrant dining options, this home offers the tranquility of a private community, easy access to the excitement KW has to offer. Enjoy picturesque views, gentle tropical breezes w/the unique charm of island living.

138 Golf Club Dr, Key West
1500 Seminary St Unit APT 2D, Key West
$515,000
1 Beds ⋅ 1 Baths ⋅ 621586 MLS
Close to Duval Street but away from the hubbub, this immaculately presented one bedroom condo is just a few blocks from Smathers Beach and vibrant White Street with its restaurants, cafes, gourmet food store, galleries and fitness studios and just a walkable, rideable, half mile from the Atlantic and a mile from the Historic Seaport District and Gulf.......The condo is part of a very well run and maintained six-unit association in a highly desirable location that is peaceful and quiet. Adorable ''Sandbar Cottage'' is one of four condos located in the beautiful old 1928 yellow house part of the compound on the corner of Seminary St and Leon St.......The large windows, glass impact front door and high ceilings make this condo feel bright and spacious, giving it an abundance of natural light. The historical charm of the kitchen, main living area and bedroom are balanced by a beautifully remodeled bathroom featuring built-in cabinetry with Louisville tile in the walk-in shower and floor. All four rooms have ceiling fans.......Enjoy solitude inside or join the vibrant island life on your own 9'x 12' newly added deck built around a mature frangipani tree. The six units also share a garden area with a variety of native specimens.......The monthly condo dues cover the flood, windstorm and general liability insurances as well as yard maintenance, exterior painting and repairs.

1500 Seminary St Unit APT 2D, Key West
1318 Duncan St Unit APT 3, Key West
$539,900
1 Beds ⋅ 1 Baths ⋅ 621579 MLS
Great opportunity to own your own home or have an excellent source of rental income. Currently the least expensive detached residence in Key West. Freshly painted interior and new AC. This renovated one bedroom condo cottage overlooking the large communal pool is just one block to vibrant White St with its cafes and restaurants, gourmet food stores, galleries and yoga studios. A short walk or bike ride to the beaches and the heart of Old Town, the Historic Seaport and Duval Street.....The compound has a large pool shared with only 3 other condos. There are lovely landscaped communal areas with fruit trees, sun decks, lounge chairs and outdoor dining areas.....Recent improvements to the home include a metal roof, impact windows plus additional storm shutters. The condo has one bedroom, a full bath with shower above, full kitchen and double doors leading to the pool and patio area.

1318 Duncan St Unit APT 3, Key West
1011 Whitehead St, Key West
$3,795,000
3 Beds ⋅ 5 Baths ⋅ 621561 MLS
Rare Old Town mixed-use opportunity at 1011 Whitehead Street, just steps from Duval Street, the Key West Lighthouse and the Hemingway Home. This historic property features three beautifully updated, furnished one-bedroom residences, each with its own kitchen and transient rental license, allowing the units to be rented individually or together. Private patios and balconies add classic Key West charm, while a street-level commercial storefront provides an additional income-producing component. With three valuable transient licenses, flexible use and an iconic walkable location, this is a unique opportunity to own a distinctive piece of Key West.

1011 Whitehead St, Key West
1311 Truman Ave, Key West
$6,449,000
7 Beds ⋅ 8 Baths ⋅ 621544 MLS
Some Key West homes are historic because they are old. 1311 Truman Avenue is historic because of who built it, who gathered within its walls, and who saved it. Its front door came from the Old Southernmost House. Past it, Dade County pine flows through every room, chandeliers light high ceilings on both floors, and the original staircase still rises where it has stood for more than a century. A second staircase toward the rear, also original to the house, recalls the scale on which it was built. Outside, sweeping double-story porches wrap the Victorian-influenced home, set on a third of an acre. The house was built at the turn of the twentieth century by Benjamin Douglas Trevor and his wife, Mary Fogarty Trevor. Mr. Trevor founded Key West's first Steam Laundry and in 1903 became Mayor of Key West. In the decades that followed, the house became home to the Key West Woman's Club and later served as a church. In 1975 two prominent local antique dealers purchased it and returned it to its original glory, and their work received the first award for an excellent restoration given by the Old Island Restoration Foundation. That restoration still defines the house. The original windows remain, along with the moldings and trim, and verandas open to the grounds from both floors. A large covered porch offers room for both dining and living, with views over the refinished pool and the guest cottage. Over the past decade, the current owners have carried that stewardship forward. A magnificent tropical garden and a stunning pool now grace the 14,490-square-foot lot. Every bathroom has been updated and finished in a fine selection of marble, granite, and quartz, and the kitchen and appliances have been updated, bringing modern comfort to a house whose history remains its defining feature. Built by a mayor, gathered in by the Woman's Club, and saved by the restoration that set the standard for Old Town, 1311 Truman Avenue is ready for the next chapter of its story.

1311 Truman Ave, Key West
1501 Truman Ave, Key West
$3,750,000
4 Beds ⋅ 4 Baths ⋅ 621522 MLS
Exceptional Key West Investment Opportunity with 3 Transient Licenses. The property consists of four private one bedrooms, one bath units, each featuring its own kitchen, living area, bedroom, and full bathroom. Most importantly, three of the four units benefit from transient rental licenses allowing nightly rentals, an increasingly rare and valuable asset in the Key West market. The fourth unit is currently rented monthly. Guests enjoy a shared private courtyard with a swimming pool, creating an inviting tropical setting and a desirable amenity for vacation renters. The property also offers three parking spaces, an added convenience in Key West. Renovated in 2018, the units blend classic Key West character with modern updates. Features include Dade County pine, engineered wood flooring, granite countertops, updated kitchen cabinetry and appliances, along with updated plumbing and electrical systems. Each unit is designed to operate independently, making the property well suited for continued use as an income producing investment.

1501 Truman Ave, Key West
1010 Olivia St, Key West
$3,750,000
3 Beds ⋅ 4 Baths ⋅ 621485 MLS
New construction, Elevated 3BD/3.5BA with heated pool and gated off-street parking on coveted Olivia Street. The Twins on Olivia is a Key West landmark reborn. The original structures, known locally as 'Olivia's Twins' and documented on the 1892 Sanborn maps, were condemned by the city and demolished. In their place, Kanga Construction has built an all-new 2,421 sq ft home on a 2,773 sq ft lot, designed with extensive guidance from Key West's HARC to honor the original twins in form and spirit. That history lives on in two separate staircases, a nod to the original pair of homes that also gives guests or family their own side of the house. All three bedrooms have ensuite baths and built-in closets, and dual-zone A/C with two whole-house dehumidifiers keeps every room comfortable year-round. French oak floors run throughout bright, open living spaces. The kitchen pairs Viking appliances, including a gas range and ice maker, with custom Hansel & Bringle cabinetry and quartz countertops. Impact-rated windows and doors, among them a custom mahogany front door with matching mahogany entry and lattice details, combine island craftsmanship with hurricane protection. Outside, ipe decking surrounds a heated pool with waterfall, set within private tropical landscaping. Off-street parking sits behind an electric gate. The home is offered fully turnkey, with a curated furniture package by local designer David Smith valued at over $150,000 plus plantation shutters throughout, all steps from Old Town's best restaurants, galleries and landmarks. Historic Key West character, built new.

1010 Olivia St, Key West
2911 Seidenberg Ave, Key West
$1,100,000
3 Beds ⋅ 2 Baths ⋅ 621482 MLS
Welcome to your dream home in the heart of Key West's MidTown! This beautifully updated 3-bedroom, 2-bathroom residence blends modern comfort with island charm. Step inside to a spacious, open-concept living area designed for both relaxing and entertaining. The true highlight is the private backyard oasis -- featuring a sparkling pool surrounded by fresh tropical landscaping, an expansive deck, and plenty of room for outdoor dining and lounging. Whether hosting guests or enjoying a quiet evening under the palms, this outdoor retreat feels like your own private paradise. Recent renovations provide peace of mind, including new impact windows and doors, Hardie board siding, and other thoughtful upgrades. Off-street parking adds everyday convenience. Perfectly located in the desirable MidTown neighborhood, this home keeps you close to shopping, dining, and all the best of Key West living. Don't miss this opportunity to own a beautifully updated slice of paradise in Key West -- schedule your private showing today!

2911 Seidenberg Ave, Key West
927 Thomas St Unit 1, Key West
$1,133,000
2 Beds ⋅ 3 Baths ⋅ 621479 MLS
Your Old Town Key West dream can start now -- with income built in. This exceptional 2-bedroom, 2.5-bath, townhouse-style condo offers a rare combination of Old Town lifestyle, flexible living space, and income-producing potential. Currently configured with a lock-off 1-bedroom apartment, the property offers an ideal opportunity for the future Key West homeowner: enjoy the larger 1 Bedroom, 1.5 Bath unit with private garden/patio as your own Key West retreat while the lock-off apartment provides substantial annual rental income. When the time comes to make Key West your full-time home, the property can be easily converted back to its original spacious 2-bedroom townhouse-style layout. A private gated entry opens to your own generous outdoor oasis, complete with a waterfall pond, large patio, and charming ''she-shed'' -- perfect for storage, an art studio, or entertaining. Inside, you'll find high ceilings, abundant natural light, generous storage, in-unit washer/dryers, and newer stainless-steel appliances. Just two blocks from Duval Street in the heart of Old Town's vibrant Bahama Village, you're surrounded by restaurants, galleries, shops, nightlife, and countless Key West attractions -- all within easy walking distance. Whether you're ready for a Key West home now or envision making the island your full-time home in the future, this is a rare opportunity to own your piece of Old Town, enjoy income along the way, and ultimately create the spacious Key West home you've been dreaming of. Some seller financing considered. Seller is a Florida Licensed Realtor. Photos 10-17 show Original Layout, 18=FloorPlan, 19-37 show Back Unit, 38-49 show Front Lock-Off Apt.

927 Thomas St Unit 1, Key West
317 Whitehead St, Key West
$6,895,000
6 Beds ⋅ 7 Baths ⋅ 621466 MLS
The Autograph House is a newly built, architect-designed luxury property in the heart of Old Town Key West, ideally positioned just one block from Duval Street and the island's most celebrated attractions. Blending refined modern design with the relaxed elegance of Key West, this exceptional property offers a rare combination of sophistication, privacy and walkable convenience. The home encompasses a stunning two-story Main Residence with four private bedroom suites, each featuring an en-suite bath with custom millwork, along with a beautifully appointed two-bedroom, two-bath Guest Cottage. Together, the residences create an exceptional six-bedroom, six-bathroom estate ideal for multi-generational living, extended stays, or entertaining. The Main Residence features an expansive open-concept living, dining, and chef's kitchen with premium Miele appliances, Fisher & Paykel column refrigeration, custom cabinetry, and a generous island. Floor-to-ceiling impact-rated sliding glass doors open seamlessly to a covered outdoor living and entertaining area, complete with lounge seating, a fully equipped outdoor kitchen, grill, beverage refrigerator, and dining space. Lush tropical landscaping surrounds a private heated pool and separate hot tub. The Main Residence pool features a waterfall and built-in bench seating, while the Guest Cottage offers its own private spa hot tub. An outdoor shower and secluded garden spaces further enhance the resort-like setting. Throughout the property, custom finishes, beautiful furnishings, Sonos audio, and full-size laundry facilities reflect an exceptional level of comfort and attention to detail. Perfectly situated in Old Town's X-Flood Zone, this home places Duval Street, Mallory Square, world-class dining, galleries, shopping, beaches, and iconic Key West landmarks just moments away. A rare opportunity to own a turnkey luxury compound in one of Key West's most coveted locations. Call today for a showing!

317 Whitehead St, Key West
1212 Olivia St, Key West
$2,475,000
3 Beds ⋅ 2 Baths ⋅ 621462 MLS
Discover the charm of what was once a carriage house and now a single-level home nestled in the highly desirable Meadows neighborhood of Old Town Key West. This inviting 3-bedroom, 2-bath residence blends historic character with modern updates, offering the quintessential island lifestyle. Effortless indoor-outdoor living defines this home, which features an open, airy feel that flows seamlessly to a private backyard oasis. The renovated kitchen features quartz countertops, modern finishes perfect for entertaining or everyday living. A versatile bonus loft provides the ideal space for a home office. Step outside to your own tropical retreat, complete with a sparkling pool surrounded by a spacious brick patio, cabana bar, fabulous outdoor shower and mature landscaping that creates privacy and a lush island ambiance. Topped off with off-street parking, whole house generator, x flood zone and close proximity to everything that makes Key West living so special, while still providing a peaceful neighborhood setting. This is truly a gem waiting to become your tropical island home!

1212 Olivia St, Key West
723 Eaton St, Key West
$6,450,000
7 Beds ⋅ 9 Baths ⋅ 621458 MLS
A rare opportunity in the heart of Old Town Key West's coveted Seaport neighborhood, this exceptional multi-residence property combines the charm and architectural character of historic Key West with the comfort, quality and convenience of newly constructed living. Thoughtfully designed to retain the home's traditional aesthetic, the property offers remarkable flexibility as a private compound, multigenerational residence or sophisticated investment property, with beautifully finished interiors, resort-style outdoor spaces and exceptional parking for the neighborhood. The main residence is a legal triplex, with each home offering its own privacy and character and 3 off street parking spaces. At the front of the property, a charming 1-bedroom, 1-bath residence occupies the first floor and opens to a generous covered porch and private yard. A separate side entrance leads to a distinctive three-story, 2-bedroom, 2.5-bath residence with its own side porch and upper levels overlooking the front of the property. Occupying the rear portion of the main house is the largest residence, a spacious 3-bedroom, 3.5-bath home arranged entirely on the main living level. Beautifully finished interiors open to a lush tropical retreat with a private pool, fountains, expansive patios, outdoor dining and multiple lounging areas. An unfinished basement offers exceptional potential for a wine cellar, tasting room or collection space. A landscaped walkway leads to a separate 1-bedroom, 1-bath cottage fronting Peacon Lane, with a private rear deck, outdoor dining area and two-car off-street parking. Importantly, the Peacon Lane residence sits on its own separate legal parcel, providing the rare flexibility for it to be owned or sold independently from the main property should a future owner ever choose to do so. Just beyond the gates, the waterfront, restaurants, galleries, shops and historic sites are all within an easy walk in one of Old Town Key West's most desirable neighborhoods.

723 Eaton St, Key West
3200 Harriet Ave, Key West
$665,000
2 Beds ⋅ 2 Baths ⋅ 621434 MLS
3200 Harriet Avenue | Key West, FL Tucked away on a desirable corner lot, this spacious 2-bedroom, 1.5-bath townhouse offers 1,332 square feet of comfortable living and one of the largest floor plans in the community. Combining privacy, generous living space, and exceptional outdoor amenities, this home is a rare find in Key West. One of the property's most appealing features is the absence of HOA fees, allowing you to enjoy all the benefits of homeownership without monthly association dues or restrictive community fees. It's a rare opportunity to own a spacious townhouse with the freedom and flexibility typically associated with a single-family home. Step outside to your own private pool, creating the perfect setting for entertaining, relaxing, or enjoying the tropical island lifestyle year-round. The corner-lot location provides added privacy and outdoor space, making this home feel even more secluded. Inside, the well-designed floor plan offers bright, inviting living spaces with plenty of room to gather, work from home, or simply unwind after a day on the water. Conveniently located in New Town, 3200 Harriet Avenue is just minutes from shopping, dining, schools, beaches, and all that Old Town Key West has to offer. Whether you're looking for a primary residence, vacation home, or investment property, this home delivers an outstanding combination of space, privacy, and the quintessential Key West lifestyle.

3200 Harriet Ave, Key West
197 Golf Club Dr, Key West
$1,350,000
3 Beds ⋅ 3 Baths ⋅ 621423 MLS
Welcome to the Sanctuary! This UPDATED/REMODELED gated single family POOL home is located on the 18th hole of the world famous Rees Jones designed Key West Golf Course. 1600 sq ft of living space with 3 bedrooms and 2.5 bathrooms. This 2 story home features an open floor plan with 9 ft ceilings and lots of windows allowing in natural light. An updated half bath is conveniently located on the first floor. The kitchen was updated with Calcutta Quartz countertops, ceramic plank tile backsplash resembling a weathered coastal wood and stainless steel Cafe appliances. Travel up the stairs with new Bamboo flooring to 3 bedrooms and 2 more updated baths. The Primary Suite features a Spa Like Escape bath with waterfall shower. French doors off the Primary Suite open to a screened balcony porch with views of tropical foliage and private pool. The pool was recently resurfaced and the pool pump and pool heater replaced. Sprinkler system also replaced. Freshly painted exterior. 24 hour security, fitness room, additional community pool are just a few of the amenities this property offers. You don't want to miss this beautiful turn key home in one of the most tranquil settings in Key West. It's a true Coastal Charmer!

197 Golf Club Dr, Key West
646 William St, Key West
$1,400,000
3 Beds ⋅ 2 Baths ⋅ 621406 MLS
644 William Street The property being sold is 644 William Street. The current property record/card reflects both 644 and 646 William Street, although the property being conveyed is 644 William Street. The structure at 644 William Street is a two-and-a-half-story home currently configured as a duplex and is in need of renovation. The first floor consists of two bedrooms and two bathrooms. The second floor contains two bedrooms and one bathroom. A stairwell provides access to the third floor, which is currently unfinished and is not completed or configured as living space. In its current condition, the property contains four bedrooms and three bathrooms of finished living area, with additional unfinished space on the third floor. The property is currently being used/configured as a duplex and will require renovation.

646 William St, Key West
3316 Harriet Ave, Key West
$535,000
2 Beds ⋅ 2 Baths ⋅ 621365 MLS
Priced to sell and one of the most affordable opportunities in the popular Key West Estates! 3316 Harriet Avenue is an excellent option for a first-time homebuyer, investor, or workforce housing, offering NO HOA fees, deeded parking, shed, screened in covered porch, air-conditioning, and a private fenced outdoor area complete with landscaping. Conveniently located in New Town near shopping, schools, recreation, and everything Key West has to offer! This property provides a rare opportunity to own in Key West at an approachable price point. Schedule a showing today!

3316 Harriet Ave, Key West
1220 Newton St Unit 5, Key West
$779,000
4 Beds ⋅ 2 Baths ⋅ 621353 MLS
Welcome to 1220 Newton Street, Unit 5, located in the beautiful Meadows neighborhood of Key West's Historic Old Town. For those looking for space and value in Key West, this four-bedroom, two-bathroom home is a rare find. Featuring impressive 10-foot ceilings, original hardwood floors, and plenty of natural light, the residence spans the second and third floors of this classic Conch mansion. Step inside to a bright and comfortable living room with an abundance of natural light. A great space to relax, entertain, or simply enjoy being home. The kitchen is conveniently located just off the main living area. Also on this level is a generously sized bedroom with French doors that could easily serve as a home office, den, or game room. A full bathroom is just around the corner and completes the main level. Upstairs, you'll find three additional bedrooms and a second full bathroom, providing separation and privacy from the main living areas below. This property offers plenty of flexibility as a full-time residence or investment property with the potential for long-term rental income. Call today to schedule your private showing!

1220 Newton St Unit 5, Key West
1216 Packer St, Key West
$1,299,000
2 Beds ⋅ 2 Baths ⋅ 621345 MLS
Experience the charm and ideal location that make Old Town Key West so special. Located in the desirable X Flood Zone, this two-bedroom, two-bath home offers an inviting layout filled with classic island character. A wine refrigerator provides a convenient touch for entertaining or enjoying a chilled bottle at the end of the day. The outdoor space is a true highlight, featuring a spacious 31-by-11-foot saltwater pool equipped with both a heater and chiller for year-round enjoyment. Ideally situated just minutes from Duval Street, restaurants, galleries, and shops, this home provides easy access to everything that makes Key West such a unique place to live and enjoy.

1216 Packer St, Key West
620 Thomas St Unit 149, Key West
$869,000
2 Beds ⋅ 1 Baths ⋅ 621337 MLS
Highly Desirable First-Floor Shipyard Condo in Truman Annex. Experience the best of Key West living in this beautifully refreshed first-floor 2-bedroom, 1-bath condo in the highly sought-after Shipyard Condominiums at Truman Annex. Thoughtfully updated with fresh interior paint, new flooring, updated furnishings, this inviting residence offers a comfortable and stylish setting for enjoying the island lifestyle. The spacious rear deck extends the living space outdoors and provides the perfect spot to relax, dine, or unwind after a day exploring Key West. Fresh landscaping enhances the tropical surroundings and adds to the property's welcoming appeal. Ideally located within Truman Annex, the condo is just a short stroll from Duval Street, the waterfront, restaurants, galleries, shops, and downtown Key West attractions. An assigned parking space adds convenience, a valuable feature in this sought-after location. The property has a non-transient rental license permitting rentals of 28 days or more, offering flexibility for those looking for a Key West retreat with the opportunity for monthly rentals.

620 Thomas St Unit 149, Key West
806 Florida St Unit APT 5, Key West
$649,000
1 Beds ⋅ 1 Baths ⋅ 621325 MLS
1 bedrooms and 1 bathrooms, you are going to enjoy the 626 sqft that composes this Condominium. Nested in an enjoyable neighborhood (the Meadows), and minutes from local attractions, restaurants, the waterfront, and public park. New central A/C, new washer/dryer, new ceiling fans, high ceilings, stainless steel appliances, tile floors, and an entry deck with hurricane-proof French doors. Plus a large, shared courtyard, grill, and 10' X 25' heated pool.

806 Florida St Unit APT 5, Key West
3314 Northside Dr Unit 55, Key West
$599,900
3 Beds ⋅ 2 Baths ⋅ 621290 MLS
Exceptional Family Home or Investment Opportunity in Solana Village! Beautifully updated elevated 3-bedroom, 2-bath home featuring impact-resistant doors and windows, a renovated kitchen, a 4-year-old roof with remaining warranty, and a 4-year-old AC. Bright, open living spaces are filled with natural light, while the spacious porch offers the perfect place to relax and enjoy the Florida lifestyle. Located in desirable Solana Village, this home offers low HOA fees of just $1,500 per year and access to a large community pool. Ideal as a primary residence, vacation home, or investment property. Property owned by listing agent.

3314 Northside Dr Unit 55, Key West
611 Grinnell St Unit 6, Key West
$950,000
2 Beds ⋅ 1 Baths ⋅ 621278 MLS
Grinnell Street is often said to be one of the best streets to live on in Old Town, and this charming 2-bedroom home makes it easy to see why. Tucked away in a small, quiet association of just seven residences, the property offers a peaceful setting right in the heart of Old Town, Key West. Inside, the home is bright and beautifully updated, with plenty of natural light throughout. The kitchen has been tastefully updated with crisp white cabinetry, quartz countertops and stainless steel appliances. The spacious primary bedroom is filled with natural light, while the second bedroom is perfect for guests, a home office, or both. A beautifully renovated bathroom and new A/C units complete the interior. One of the best parts of this home is the outdoor space. There are several private areas to lounge and unwind, along with your own outdoor dining space for enjoying morning coffee or dinner outside. A grill on site makes it easy to cook and entertain without ever having to leave home. The association also features a large heated swimming pool surrounded by beautiful landscaping, perfect for cooling off after a bike ride through Old Town. The home is being offered fully furnished and has future bookings already in place should the new owner wish to continue renting. Walk to neighborhood coffee shops, some of Key West's best restaurants and shops, the Historic Seaport and everything Old Town has to offer. Quiet, charming and incredibly well located, this is an easy Key West home to fall in love with.

611 Grinnell St Unit 6, Key West
418 Appelrouth Ln, Key West
$1,200,000
1 Baths ⋅ 621247 MLS
Located off the 500 block of Duval Street. High traffic location on Appelrouth Lane between Duval Street and Whitehead Street. This is real estate only. Business is not for sale. Second floor is currently unused. PROPERTY IS IN THE TRANSIENT LICENSE ZONE. Do not disturb business.

418 Appelrouth Ln, Key West
614 Roberts Ln, Key West
$900,000
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
613 Margaret St, Key West
$5,400,000
6 Beds ⋅ 7 Baths ⋅ 621215 MLS
Step back into timeless Key West soul, where leaf-stamped garden paths, sun-dappled outdoor showers, and the gentle trickle of private pool waterfalls create an unforgettable Old Town sanctuary. Hidden behind a classic wooden gate just moments from the Historic Seaport and Duval Street, this compound offers two private, fully equipped homes on a lush 7,796-sq. ft lot, providing the ultimate luxury island retreat or multi-generational estate. Verdant foliage frames the wrap-around front porch of the front cottage, inviting you to sit back and enjoy quintessential island living. Inside, sky-lit vaulted ceilings with exposed wooden beams pour warm sunshine across white-painted walls and rich wood floors. The light-filled layout centers around an enchanting cottage kitchen filled with warmth and timeless charm that flows seamlessly into the living space and guest half bath. Three bedrooms-each featuring its own private ensuite bath-offer exceptional comfort. Floor-to-ceiling glass draws you out to an outdoor dining area and a sparkling heated pool nestled among vibrant gardens. Wander through the botanical grounds to the rear house, a custom-crafted two-story sanctuary built in 2016. Showcasing exquisite Hickory hardwood floors, whitewashed Cypress interior walls, and slate-tiled baths, this home balances coastal elegance with high-end luxury. The chef's kitchen boasts an elite ILVE range and custom cabinetry, flowing into open living quarters that slide open to the backyard oasis. The main floor offers versatile living with a guest suite that double-functions as a private home office with a built-in Murphy bed. Upstairs, a Craftsman staircase leads to a secondary guest suite with an ensuite bath and a sprawling primary retreat, complete with an oversized spa bath and a private balcony overlooking the second heated waterfall pool. Do not miss this rare chance to own one of Old Town's premier dual-home properties, complete with dedicated off-street parking for two cars.

613 Margaret St, Key West
14 Spoonbill Way, Key West
$1,195,000
3 Beds ⋅ 3 Baths ⋅ 621211 MLS
Welcome to 14 Spoonbill Way, an exceptional single-family home in Key West's sought-after golf club community, offering scenic golf course and lake views alongside a relaxed, resort-style lifestyle. Featuring 3 bedrooms, 2.5 bathrooms, and a spacious bonus room currently configured as a bunk room, this home combines flexible living space, indoor-outdoor entertaining, and desirable community amenities in one inviting Florida Keys property. The main level features an open-concept floor plan connecting the kitchen, dining area, and living room, creating a bright and welcoming space for everyday living and entertaining. Step outside onto the spacious back deck overlooking the golf course and lake, where you can enjoy morning coffee, outdoor dining, or sunset cocktails with peaceful waterfront and fairway views. Upstairs, the private primary suite offers a relaxing retreat with its own deck and walk-in closet--an uncommon and desirable feature within the community. Two additional bedrooms and a full bathroom provide comfortable accommodations for family and guests. Enjoy the benefits of resort-style living in Key West, with community amenities that include two swimming pools, a fitness center, a beautiful butterfly garden, and more. The home's convenient location within the community places it close to the larger resort pool, with nearby guest parking that makes hosting friends and family easy. Whether you're searching for a primary residence, a vacation home in Key West, or a property with golf course views and resort-style amenities, 14 Spoonbill Way offers an appealing combination of comfort, versatility, and island living. Discover the opportunity to enjoy spacious indoor-outdoor living, peaceful golf course and lake views, and desirable community amenities in one of Key West's sought-after residential communities.

14 Spoonbill Way, Key West
516 Elizabeth St, Key West
$1,890,000
2 Beds ⋅ 3 Baths ⋅ 621199 MLS
Nestled in the heart of Old Town Key West, this historic gem boasts an impeccable blend of classic architecture and modern amenities. With a rich history dating back to the late1800's, this captivating residence offers the perfect opportunity to own a piece of Key West's storied past. Listed on the National Register of Historic Places and awarded the Gold Star for Historic Preservations, 516 Elizabeth St. is the perfect example of a Classical Revival Eyebrow House - a style unique to Key West. The roof overhangs over the second floor windows onto classic porch columns giving the suggested appearance of 'eyebrows' providing protection from rain and sun allowing the inside to have fresh air even during the hot summer months. Upon entering the home, original Dade County pine walls, high 10ft ceilings, original double hung wooden windows exude the timeless elegance of a bygone era. While preserving its historic character, this home has been thoughtfully updated with modern amenities. The kitchen features custom wooden cabinets and stainless steel appliances and all bathrooms are beautifully renovated. Enjoy the convenience of contemporary living without compromising on the historic appeal. The primary bedroom and bathroom upstairs provide a tranquil retreat, and the guest bedroom downstairs with it's own bathroom is convenient and comfortable. French doors lead from the formal dining room and kitchen to a sundeck with a covered dining area and extra lounging space to entertain. A Pool with water feature and new decking was just added to the property. This home has a rich history, with tales of past occupants, the Pinder family, and the unique stories of its heritage adding an extra layer of prestige and historical significance to its charm. This historic home is a rare find in a prime location, offering the best of both worlds. The house has some monthly vacation rental history and is sold furnished (some personal pieces & all art work excluded)!

516 Elizabeth St, Key West

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