The Meadows Homes for Sale

In Key West, Florida, on the northwest side of Old Town, you’ll find the spectacular Meadows neighborhood. The Meadows epitomizes Key West charm with its peaceful streets lined with colorful homes and lush landscaping. This upper-end neighborhood has an ideal central location in walking distance to Downtown Key West. The Meadows is a quick ride to the area’s best shopping venues and you can bicycle to the beach. There is ample parking and for all of these reasons and more, The Meadows is one of Key West’s most desirable neighborhoods in which to buy a home.

The Meadows neighborhood is approximately twenty-four blocks in size and is comprised of a series of parallel one-way streets. The main streets of this family-friendly neighborhood are Olivia, Pine, Petronia, and Newtown and you’ll find them lined with gorgeous Mahogany, Royal Poinciana, and palms. Unlike the hustle and bustle you’ll find on Duval, the charming streets in The Meadows are a perfect escape. That said, they are all within walking distance of the area’s great shopping, dining, entertainment, and recreation.

This quiet residential area was developed primarily in the early 1900s and most of the original homes are still standing with all their historic charm intact, and have been meticulously maintained or renovated. Homes for sale in The Meadows of Key West include a wide variety of architectural styles such as grand waterfront estates, bohemian style bungalows and a multitude of traditional conch homes. Whether you are looking for the perfect vacation home or a new primary residence, you would be remiss not to consider the exceptional real estate of The Meadows. If you would like to learn more about the homes for sale in The Meadows of Key West, Florida, please allow us to assist you and contact us today.

The Meadows Newest Listings

1407 Petronia St, Key West $1,875,000

Wonderful Old Town Meadows home with 4 Bedrooms, 3 Baths, on a nearly 5000 sq ft lot, this property has a separate Guest Cottage, wrap around front porch, lap- pool, ...

4 Beds
3 Baths
620682 MLS

901 Eisenhower Dr, Key West $4,750,000

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 histo...

6 Beds
5 Baths
620662 MLS

901 Eisenhower Dr, Key West $4,750,000

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 histo...

7 Beds
5 Baths
620661 MLS

1105 Olivia St, Key West $849,000 ▼

This elegant historic Old Town cottage is a rare offering paired with a highly competitive price. Sparkling, gallery-like, and filled with natural light, this beautif...

1 Beds
1 Baths
620379 MLS

1402 Olivia St Unit 2, Key West $639,000

Discover your ideal pied-à-terre in the heart of Key West! This charming 1-bedroom, 1-bathroom apartment on Olivia Street offers a perfect blend of comfort and convenienc...

1 Beds
1 Baths
620158 MLS

Rat, Key West $850,000

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 bu...

2 Baths
619620 MLS

1212 Olivia St, Key West $2,475,000 ▼

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 Beds
2 Baths
619515 MLS

1319 Newton St, Key West $1,750,000

Discreetly tucked within the storybook streets of the coveted Meadows, this enchanting Key West residence is a rare expression of timeless elegance and island sophisticat...

3 Beds
2 Baths
619504 MLS

1317 Newton St, Key West $1,100,000 ▼

Charming 2BD/2.5BA Key West cottage nestled in the sought-after Meadows neighborhood. Recently refreshed inside and out, this home features newer stainless steel applianc...

2 Beds
3 Baths
619283 MLS

815 Pearl St Unit 2, Key West $575,000 ▼

Quaint Key West Condominium - Discover 815 Pearl Street Unit 2, a charming 1-bedroom, 1-bath residence in the heart of Old Town. Light fills the open-concept living area,...

1 Beds
1 Baths
618227 MLS

817 Pearl St, Key West $875,000 ▼

Charming Home in the Meadows, Old Town, Key West. This beautiful completely renovated one bedroom cottage on Pearl Street is move in ready, and is being sold furnished. ...

1 Beds
1 Baths
618771 MLS

1513 Pine St, Key West $1,899,000

Located on a corner lot in the highly sought-after Meadows neighborhood, this beautifully crafted Key West home offers exceptional design, privacy, and outdoor living. Bu...

2 Beds
3 Baths
618826 MLS

1203 Newton St Unit 1, Key West $699,000

Picture perfect condo located in 1 of 2 historic buildings totaling 8 units with a generous sized shared pool and lounging area. This setup is ideal for 1-2 people lookin...