Search for Homes in The Meadows

The Meadows

Lovely, charming and quiet.

The Meadows is a lovely, charming, and quiet area located just to the west of Bayview Park. It is bounded by Eisenhower Drive, White Street, Truman Avenue, and Angela Street. The majority of the architecture in this neighborhood are the classic Conch homes that are quintessential Key West. Homes in this neighborhood date back to the late 1800’s. Most have been restored and are meticulously maintained while only a handful remain for restoration, making this a highly desirable area within Old Town Key West. You will find a mix of year-round and seasonal residents in this neighborhood, but it has always maintained its charm where neighbors know one another.

Newton and Olivia Streets are one-way in the South-North direction. Pine and Petronia Streets are one-way in the North-South direction. Albury and Angela Streets are two-way but typically have very light traffic. All cross streets are two-way.

The proximity of Bayview Park is simply wonderful. This park features 5 tennis courts, plus private and group lessons taught by the Findlay family of Island City Tennis for over 30 years; a basketball court, a softball field, and playground. There are many events each month such as the weekly Key West Green Market held most every Thursday and the Bayview Park Free Movie Series.

The Meadows are within Old Town, but you are still walking and biking distance to Duval Street, The Historic Seaport District and the shops and restaurants of White Street. Fausto’s grocery is just on the other side of the park if you need a few items and our larger grocery stores are a mere 5 minutes away driving North on the Boulevard.

On a personal note, Derek's in-laws have owned a home in this neighborhood for over 30 years, so he knows this area very well.

New Listings in The Meadows

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

1105 Olivia St, Key West
$789,000
1 Beds ⋅ 1 Baths ⋅ 621059 MLS
Your Key West escape awaits! Trade cold winter days for sunshine, tropical breezes, and the laid-back charm of island living. This darling Conch house is beautifully renovated, completely turnkey, and perfectly suited as a winter retreat or seasonal getaway. Simply arrive, unpack, and embrace the island lifestyle! Sparkling, gallery-like, and filled with natural light, this charming Old Town cottage blends historic character with modern luxury. Tucked along a quiet one-way street, it's just a short stroll to Key West's beloved boutiques, bakeries, galleries, restaurants, and gourmet markets. Renovated down to the studs, the home features soaring vaulted ceilings and an inviting open-concept design, seamlessly connecting the gourmet kitchen, entertainment bar, and living area. Expansive sliding glass doors open to a private tropical oasis surrounded by lush fig vines, Spanish lime trees, swaying palms, and a majestic Royal Poinciana. Imagine morning coffee, afternoon cocktails, and evenings under the stars in your own secluded paradise. Upscale finishes include solid teak flooring, granite countertops, and a stunning Calacatta marble bath. Extensive improvements include updated electrical and plumbing, a tankless water heater, metal roof, impact-rated windows, and opening protections. Additional highlights include room for off-street golf cart parking, potential for a small pool, no HOA fees, and a desirable X Flood Zone location. Once home to a local cigar maker, this enchanting cottage carries a piece of Key West's rich history while offering all the comforts of modern island living. A rare opportunity to own your own slice of paradise in the heart of Old Town!

1105 Olivia St, Key West

901 Eisenhower Dr, Key West
$4,750,000
6 Beds ⋅ 5 Baths ⋅ 620662 MLS
TRANSIENT LICENSE TRANSFER RECEIVER ZONE!!!! A rare opportunity to own one of Key West's most captivating waterfront properties, where history, character, and endless potential come together. Nestled along the historic Trumbo Point waterfront, this remarkable estate has remained in the same family for generations and reflects a rich connection to one of the island's most significant maritime neighborhoods. Thought to have origins dating back to the early 20th century, the property showcases timeless Old Key West charm while offering the space and flexibility rarely found today. The main residence is complemented by a separate guest cottage on an oversized waterfront parcel, creating endless possibilities for multigenerational living, a private family compound, or an exceptional investment opportunity. Located in an area once shaped by the island's cigar industry, railroad expansion, and later the development of the Naval Air Station and Coast Guard facilities, this home sits within a neighborhood that tells the story of Key West's evolution through more than a century of history. From the moment you arrive, you'll appreciate the mature tropical landscape, water access, and the feeling of stepping into a piece of Old Key West. Whether you choose to preserve its historic character, thoughtfully enhance the existing structures, or create your own legacy estate, opportunities like this are exceptionally rare. Waterfront properties with this combination of history, location, size, and family ownership seldom become available. 901 Eisenhower Drive is more than a home--it's an opportunity to own a meaningful piece of Key West's past while creating its next chapter.

901 Eisenhower Dr, Key West

901 Eisenhower Dr, Key West
$4,750,000
7 Beds ⋅ 5 Baths ⋅ 620661 MLS
TRANSIENT LICENSE TRANSFER RECEIVER ZONE!!!! A rare opportunity to own one of Key West's most captivating waterfront properties, where history, character, and endless potential come together. Nestled along the historic Trumbo Point waterfront, this remarkable estate has remained in the same family for generations and reflects a rich connection to one of the island's most significant maritime neighborhoods. Thought to have origins dating back to the early 20th century, the property showcases timeless Old Key West charm while offering the space and flexibility rarely found today. The main residence is complemented by a separate guest cottage on an oversized waterfront parcel, creating endless possibilities for multigenerational living, a private family compound, or an exceptional investment opportunity. Located in an area once shaped by the island's cigar industry, railroad expansion, and later the development of the Naval Air Station and Coast Guard facilities, this home sits within a neighborhood that tells the story of Key West's evolution through more than a century of history. From the moment you arrive, you'll appreciate the mature tropical landscape, water access, and the feeling of stepping into a piece of Old Key West. Whether you choose to preserve its historic character, thoughtfully enhance the existing structures, or create your own legacy estate, opportunities like this are exceptionally rare. Waterfront properties with this combination of history, location, size, and family ownership seldom become available. 901 Eisenhower Drive is more than a home--it's an opportunity to own a meaningful piece of Key West's past while creating its next chapter.

901 Eisenhower Dr, Key West

Rat, Key West
$850,000
2 Baths ⋅ 619620 MLS
FOR SALE: Mellow Ventures LLC - Premier Eco-Tour & Luxury Houseboat Rental Company in the Florida Keys Step into one of the most unique lifestyle and income-producing businesses in the Florida Keys. Mellow Ventures LLC is a turnkey, multi-stream eco-tour and hospitality operation with a proven track record, established brand presence, and rare waterfront assets perfectly positioned for continued growth. Operating out of Key West, this boutique adventure company has built a reputation for intimate, sustainable experiences on the water—guided eco tours, private charters, island excursions, and custom adventures designed to showcase the natural beauty of the Lower Keys. In addition to its successful charter business, the sale includes two custom-built luxury houseboats, currently operating as high-demand short-term rentals. These floating suites offer a one-of-a-kind Airbnb experience that consistently generates strong occupancy and premium nightly rates. Each vessel blends modern comfort with an immersive waterfront setting, providing an unforgettable stay for guests seeking something truly special. Highlights Include: -Well-established eco-tour & charter business with brand recognition in Key West -24' Twin Vee -Two fully custom houseboats designed for nightly rentals -Strong Airbnb track record with exceptional occupancy -Multiple revenue streams: eco tours, private charters, overnight rentals -Turnkey operation with booking systems, media assets, furnishings & equipment -Excellent online reviews and repeat clientele -Ideal opportunity for owner-operator or investor seeking passive/managed income -Rare waterfront lifestyle business in a world-renowned destination This is a unique chance to acquire a thriving, experiential Keys business blending adventure tourism with boutique hospitality—a lifestyle investment that generates real returns.

Rat, Key West

1319 Newton St, Key West
$1,750,000
3 Beds ⋅ 2 Baths ⋅ 619504 MLS
Discreetly tucked within the storybook streets of the coveted Meadows, this enchanting Key West residence is a rare expression of timeless elegance and island sophistication. Rich in history yet effortlessly refined, the home invites you into a world where classic Conch architecture meets curated, modern luxury. From the moment you enter, the ambiance is unmistakable--soaring ceilings, warm Dade County Pine, and bespoke craftsmanship create an atmosphere that is both grand and inviting. Every space has been thoughtfully composed, balancing texture, light, and artistry to deliver a home that feels as beautiful as it is livable. Beyond the interiors, a private tropical sanctuary unfolds. Surrounded by lush greenery and designed for complete seclusion, the poolside setting evokes a boutique resort experience. Whether basking in the sun, enjoying the gentle sound of water, or hosting intimate evenings under the glow of ambient lighting, this outdoor retreat is nothing short of extraordinary. The upper-level primary suite offers a serene escape, complete with its own sitting area and a covered balcony that captures the essence of relaxed island mornings and golden-hour evenings. Guest accommodations are equally inviting, offering comfort, privacy, and flexibility for hosting family or discerning visitors. Offered turnkey, the home presents a seamless opportunity for immediate enjoyment--whether as a private coastal retreat or a high-performing luxury rental. Every detail has been considered to ensure effortless living without compromising character or authenticity. Just moments from the vibrancy of Old Town, yet worlds away in feel, this is a residence that embodies the true spirit of Key West--elegant, intimate, and undeniably captivating.

1319 Newton St, Key West

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