Search for Homes in The Meadows

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

$1,800,000
3 Beds ⋅ 2 Baths ⋅ 601673 MLS
The Robert's House is an 120 year old three story double porch Greek Revival Classic Home located in The Meadows, one of the most coveted neighborhoods in Key West. An easy walk/ bike ride to the restaurants, bars, local beaches and attractions in Old Key West, yet the home is located in a very quiet tranquil setting, perfect for taking moonlight strolls under the palms. This fully upgraded 3/2 Home has abundant outdoor living spaces, private plunge pool, chefs kitchen, rheostat lights and mature tropical landscape.

1417 Pine, Key West

Listing courtesy of Berkshire Hathaway Knight & Gardner Realty.

$1,300,000
2 Beds ⋅ 2 Baths ⋅ 601590 MLS
Peace and quiet and a boaters delight! This small eight-unit condo complex located in the beautiful Meadows neighborhood has an ordinance against vacation rentals which ensures consistent tranquility with a virtually private pool. One of the only properties close to Old Town where you can keep your boat in the water with a deeded boat slip. With the rising cost of boat slips and marina rates, the slip can save you upwards of a $1000 per month. This third floor 2BR/2BA unit allows for panoramic views of the marina and Key West. The property has had many upgrades during this ownership including new decorative floors with a coastal feel, an upgraded bathroom, new AC, washer and dryer, and some appliances. Enjoy entering a cool car with the covered parking, a rare find in The Meadows. Large private exterior storage space is included. The views are a must see!

833 Eisenhower Unit 303, Key West

Listing courtesy of Keys Atlantic Realty.

$1,175,000
2 Beds ⋅ 2 Baths ⋅ 601536 MLS
This condominium is perfect for island life! Amazing water views from your covered porch, comes with a boat slip, parking, and a spacious floor plan. Elevated condo with access from stairs or elevator. Centrally located in The Meadows of Key West this home features views of the Garrison Bight Marina. Primary bedroom offers bath en suite, second bedroom has attached bath. Updated kitchen with laundry in unit, light filled dining and living area. Enjoy relaxing on the covered porch with plenty of room for entertaining and outdoor dining. BOAT SLIP! POOL! PARKING! STORAGE!

833 Eisenhower Unit 101, Key West

Listing courtesy of Bascom Grooms Real Estate (Kw).

$4,999,000
5 Beds ⋅ 4 Baths ⋅ 601372 MLS
WATERFRONT KEY WEST INVESTMENT OPPORTUNITY!!! Once in a lifetime chance to restore and or redevelop a commercial waterfront property located on the edge of Old Town, Key West. Built prior to 1912 and owned by the same family for over 100 years, 901 Eisenhower Drive is well-sited on an expansive 15,609SF lot and is zoned General Commercial offering endless investment potential. Conditional uses include a restaurant, hotel, or marina.The property is currently set up as a legal five-unit multi-family rental with two structures consisting of a historic main home and a separate cottage. The main residence has 4 units including 5 bedrooms and 4 bathrooms while the separate cottage includes 2 bedrooms and 1 bathroom. Located on Garrison Bight and just a half a block away from Bayview Park, Tennis Courts, and biking distance to the island's best beaches and amenities.Buyer to verify restoration and or development rights. Tenant Occupied/48 hours notice to show - we may not be able to all units on the same day.

901 Eisenhower, Key West

Listing courtesy of Truman & Co. (Kw).

$3,900,000
4 Beds ⋅ 4 Baths ⋅ 601346 MLS
Beautifully renovated, Bayview House is a hotel with 4 units out of which 3 have daily transient licenses. Great investment opportunity, each unit is a suit, has a full kitchen and private bathroom and they all share a pool. Total payouts in Airbnb and VRBO for the last 365 days together with the 3,000 a month non transient are just under $450k. The buyers will receive both -the VRBO and the AIRBNB account -with the purchase. Let's take a look and make this happen!

1501 Truman, Key West

Listing courtesy of Key West Luxury Real Estate Inc (Kw).

$3,699,999
3 Beds ⋅ 3 Baths ⋅ 600958 MLS
What lies behind the gates on a nearly 5,000sf lot in the Meadows is nothing short of exquisite! Here you will find the perfect indoor/outdoor living experience with an ambiance of elegance and privacy. This charming Key West home has a total of 3 Bedrooms/2.5 Baths and just over 2,000sf of living space. The main living area, with vaulted ceilings, has three sets of French doors opening to a covered outdoor dining area with a 300sf pool. The entire property is surrounded by lush tropical landscaping. Inside, the kitchen is a Chef's dream, with quartz counter tops, Viking (induction) & Wolf Stainless steel appliances, custom built cabinetry, a butler's pantry, and full built-in wet bar. Located on the first floor, there is an expansive, light filled master suite with double French doors, crown molding, custom built-in shelving, a separate office & a rare walk-in closet. Upstairs there are two additional guest bedrooms, each having their own in-room vanity basins and an additional shared bathroom. The entire home is wrapped with 2,000sf of IPE decking. Just a short distance to Duval Street and the Historic Seaport in one direction, and easily accessible to all New Town services in the other, this is the perfect Old Town Key West home. *Sellers prefer to negotiate & add acceptable terms by both the buyers & sellers for a 6 month post occupancy agreement. Such terms shall be added to the sales contract & the post occupancy agreement with agreed upon terms shall be executed at time of closing. Minimum 24 Hours Notice To Show.

1414 Angela, Key West

Listing courtesy of Truman & Co. (Kw).

$1,499,000
2 Beds ⋅ 3 Baths ⋅ 599796 MLS
Blink and you'll miss it! A wonderful Key West cottage in the Meadows with 2 bedrooms, 2.5 baths & a pool! The home has a much desired first floor primary bedroom with the second bedroom and bath being upstairs. Enjoy an open concept kitchen & living room at the the rear of the home with a wall of French doors opening up to the pool, hot tub and covered lounge area. Cathedral ceilings, Mexican tile floors, front porch & rear deck. Lounge by the pool or relax under your entertaining gazebo, sipping your pleasure.....all in the peace of your own private paradise.

1317 Newton, Key West

Listing courtesy of Truman & Co. (Kw).

$4,999,000
7 Beds ⋅ 5 Baths ⋅ 598681 MLS
KEY WEST WATERFRONT INVESTMENT OPPORTUNITY!!! Once in a lifetime chance to restore and/or redevelop a commercial waterfront property located on the edge of Old Town, Key West. Built prior to 1912 and owned by the same family for over 100 years, 901 Eisenhower Drive is well-sited on an expansive 15,609SF lot and zoned as General Commercial offering endless investment potential. Conditional uses include a restaurant, hotel, or marina.The property is currently set up as a legal five-unit multi-family rental with two structures consisting of a historic main home and a separate cottage. The main residence has 4 units including 5 bedrooms and 4 bathrooms while the separate cottage includes 2 bedrooms and 1 bathroom. Located on Garrison Bight and just a half a block away from Bayview Park, Tennis Courts, and biking distance to the island's best beaches and amenities. Buyer to verify restoration and or development rights. Tenant Occupied/48 hours notice to show - we may not be able to all units on the same day.

901 Eisenhower, Key West

Listing courtesy of Truman & Co. (Kw).