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

3 Beds ⋅ 4 Baths ⋅ 603814 MLS

1509 Pine is absolutely divine... With several years of vacation rental history and confirmed reservations from now through April, which will generate $77k in gross income, this lovely 3 bedroom, 3.5 bath home is being offered completely TURNKEY. Just beyond the white picket fence, on a quiet one-way street in the Meadows, this grand home offers classic Key West architecture complete with Bahama shutters, upstairs balcony and a large front porch, both with dual ceiling fans. Upstairs features hardwood floors and is where you'll find the spacious master suite with vaulted ceiling, which includes a private balcony and walk-in closet; two guest suites with vaulted tray ceilings; and the washer and dryer. Downstairs you're greeted with 11 ft. ceilings that completely open up the living room space which features all impact windows, 8 ft. impact sliding glass doors, all with security sensors, travertine tile floors, half bath, wet bar with standalone wine refrigerator and Uline ice maker, and new hot water heater. The gourmet kitchen boasts granite counters and beautiful cabinetry, and the high-end stainless appliances including SubZero refrigerator, JennAir oven and convection oven, and Bosch dishwasher add an air of luxury. The sliding glass doors open out to the private outdoor oasis that offers tropical palms, heated pool with water feature, new pool heater, spa, remote controlled retractable awning covering the patio, security cameras, and access to the private carport and storage closet. Private driveway to the carport is accessible through secured electric gates off Eisenhower Drive or Pearl Street. All pool functions (heat, spa, water feature, pool lights & cleaning mode) can be controlled through an iPad in the house or remotely through an app on your phone. This lovely home has everything you need to enjoy the keys lifestyle and is just a short bike ride away from the famous Duval Street and the Historic Seaport.

1509 Pine, Key West

2 Beds ⋅ 2 Baths ⋅ 603597 MLS

Closest living to OLD TOWN with a boat slip!! Peace and quiet and a boaters delight! This small 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 an assigned 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

3 Beds ⋅ 2 Baths ⋅ 603560 MLS

Duplex in the Meadows known as the Artists House! 2 fully licensed, residential units in this highly desirable Old Town neighborhood. Solid monthly rental property with stable income. Downstairs apartment has 2bd/1ba and upstairs is 1bd/1ba. Potential for monthly Airbnb rentals. Or as a fixer upper, renovation needed to convert to a single-family conversion with income from another apartment. Good size 2,255 sf. lot with back deck & yard with room for pool. There is an existing, unused cistern at rear of property may help qualify for potential pool setback waivers. At the front of the house is a small yard & white picket fence. Existing one off-street parking space. Also there is an additional 5.29' x 74' Hiatus strip of land adjoining property on E side that is recorded and surveyed. Owner has filed an Adverse Possession claim on this Hiatus strip of land. Good size open decks up and down & screened front porch. Two Electric, Water and Sewer accounts. Each apartment has W/D hookups. Hurricane storm panels for windows & doors included. Nice residential neighborhood & Petronia St. is a one way street coming into town. Same owner for nearly 20 years. Survey of property and Hiatus strip & an Elevation Certificate on file.

1420 Petronia, Key West

1 Beds ⋅ 1 Baths ⋅ 603391 MLS

The perfect Meadows location with almost 900 square feet of outdoor space for true Key West living. Renovated 1 bedroom condo with separate 108 sq. ft cottage not included in the square footage serving as a 2nd bedroom. Open and inviting, there's a spacious and well designed kitchen with butcher block counters, a renovated bath, and a separate laundry room with built in cabinetry for additional storage. With a covered porch for outdoor seating and lush landscaping to provide privacy, you'll find an outdoor wonderland complete with shower and hot tub. And offered furnished and ready for move in or rental,

707 Florida, Key West

3 Beds ⋅ 2 Baths ⋅ 603361 MLS

Truly classic turn of the century Conch House with good bones and in need of some fixing. The Meadows corner location and a lovely garden area with room for a pool make this an even more desirable find. There are wood walls and high ceilings throughout the home, a sweet front porch and second floor rear balcony.

1225 Olivia, Key West

4 Beds ⋅ 4 Baths ⋅ 603126 MLS

Welcome to the Meadows. 823 Georgia Street is a beautifully updated Conch home with over 2,400 square feet of indoor living. First, you are invited in to the home on a grand, wrapping front porch which is a great place for book, beverage, or to sit a watch the day go by. The property provides plenty of space to stretch out with 4 bedrooms, a large loft, 3.5 baths, and an outdoor shower. Cathedral ceilings, first floor master suite, bathroom access to every bedroom and off-street parking are just a few features. The open floor plan overlooks the pool, spa, and large outdoor deck space within the beautifully landscaped property complete with lighting for after the sun sets. In the front yard lives one of the largest known boxwood trees in the country. A modern, u shaped kitchen with custom cabinetry, HVAC upgrades, Class A hurricane protection, decorative shutters, oak floors, hidden storage and laundry are details not overlooked. The current owner has established a successful vacation rental history, making it a perfect income producing property if you so desire. Just a short walk or bike ride into town and close to Garrison Bight as well. This home is ready for you to start making memories with your family and friends!

823 Georgia, Key West

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, chef's kitchen, rheostat lights and mature tropical landscape. This property has an additional 660 square feet of finished attic storage which also can double as a sleep room for children. This property is currently licensed for monthly vacation rentals and is becoming a favorite with Guests.

1417 Pine, Key West

6 Beds ⋅ 5 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

2 Beds ⋅ 3 Baths ⋅ 599796 MLS

Wonderful 2BD/2.5 BA Key West cottage in the desirable Meadows neighborhood. Freshly painted both inside and out, all new stainless steel appliances, new granite counters in both kitchen and bath, new tile bathroom upgrades plus much more! Enjoy a sun filled great room with French doors that open on to a very private pool area, hot tub and gazebo. The choice is yours, a first floor master bedroom or a second floor bedroom & bath. Conveniently located to everything Old Town & New Town have to offer, come see all the wonderful renovations just completed!

1317 Newton, Key West

6 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