Key West Sisters

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Key West Sisters Angela McChesney & Jenny Perry both born & raised in Key West and are experts in the Key West real estate market! These girls give 110% to every client.

Trust in the local, born, and raised in the Florida Keys? Angela McChesney and Jenny Sterling Realtors are experts. Buying or selling? Need property management or supervision? Key West, Lower Keys, Big Coppit Key, Key Haven, Bay Point, Sugarloaf Key, Cudjoe Key, Summerland Key, Ramrod Key, Little Torch Key, Big Pine Key, Marathon Florida

Just Listed! 1607 Sunshine Drive $1,929,000Tropical outdoor living meets the comfort of newer construction at 1607 Sunsh...
10/21/2026

Just Listed! 1607 Sunshine Drive $1,929,000

Tropical outdoor living meets the comfort of newer construction at 1607 Sunshine Drive! Built in 2014 this 3 bedroom 3 bath home offers a wonderful combination of privacy, modern features, and a convenient Key West location. The backyard is a true highlight, featuring a heated pool surrounded by tropical landscaping, spacious composite decking, and plenty of room to relax or entertain. Fully fenced with landscape lighting and irrigation this inviting outdoor space is designed to be enjoyed year round. Inside the home offers a comfortable and functional floor plan with a first floor bedroom and full bath ideal for guests or a home office. Upstairs two generously sized bedrooms each feature private bathrooms and their own outdoor decks. The kitchen is complete with quartz countertops brand new stainless steel appliances and a separate beverage pantry. Built with durability to Cat 5 hurricane codes and efficiency in mind the home features impact resistant windows and doors, a metal roof, concrete siding, and elevated construction. Two off street parking spaces provide added convenience. Whether you’re looking for a full time residence or a place to escape to Key West 1607 Sunshine Drive offers an easygoing island lifestyle with all the benefits of a newer home.

Easy to see! Contact us

10/20/2026

Just Listed! 64 Golf Club Drive, Key West, FL
$975,000
This lovely 3 bedroom and 3 full bathroom unit has an updated kitchen, convenient main level full bathroom, great location on golf course which is a very desirable. These opportunities don’t come along often. Easy to see, contact us!

Don’t sleep on this one! 750 Prado CircleWelcome to easy island living in Big Coppitt Key! This 3 bedroom, 2 bath elevat...
10/16/2026

Don’t sleep on this one!

750 Prado Circle

Welcome to easy island living in Big Coppitt Key! This 3 bedroom, 2 bath elevated home sits on a spacious 7,500 square foot corner lot offering plenty of room to enjoy the Florida Keys lifestyle. Featuring a brand new roof, storage, ample parking for your vehicles, boat, and other toys. Many options to add a pool and create your own backyard oasis. Conveniently located near the local park and boat ramp making it easy to get out on the water and enjoy everything the Keys have to offer. With a great location and plenty of outdoor space this home is ready for its next owner to make it their own!

Just Listed! 750 Prado Circle, Big Coppitt Key $795,000Welcome to easy island living in Big Coppitt Key! This 3 bedroom,...
10/16/2026

Just Listed! 750 Prado Circle, Big Coppitt Key
$795,000

Welcome to easy island living in Big Coppitt Key! This 3 bedroom, 2 bath elevated home sits on a spacious 7,500 square foot corner lot offering plenty of room to enjoy the Florida Keys lifestyle. Featuring a brand new roof, storage, ample parking for your vehicles, boat, and other toys. Many options to add a pool and create your own backyard oasis. Conveniently located near the local park and boat ramp making it easy to get out on the water and enjoy everything the Keys have to offer. With a great location and plenty of outdoor space this home is ready for its next owner to make it their own!

Sold! 211 Shore avenue $1,055,000Some things are worth the wait! 🏡After a few years of searching our sweet friends have ...
10/08/2026

Sold! 211 Shore avenue $1,055,000

Some things are worth the wait! 🏡

After a few years of searching our sweet friends have finally found their perfect place to call home! We couldn’t be happier for them and feel so grateful to have been part of their journey. There’s something extra special about helping friends find their home.

Cheers to new beginnings, happy memories and making this house your own! 🥂🔑

Just Listed! 513 Truman Avenue, Key West. $1,850,000 This Commercial Residential mixed use building offers an excellent ...
10/02/2026

Just Listed! 513 Truman Avenue, Key West.
$1,850,000

This Commercial Residential mixed use building offers an excellent investment or owner operator opportunity. A prime location 513 Truman has excellent visibility with heavy foot and vehicular traffic. Downstairs is a large commercial space currently vacant. It could easily accommodate numerous commercial tenants. Upstairs are two apartments including a one bedroom one bath and a large studio. Both residential units have modern finishes including full kitchen, granite counters, stainless appliances, ample closet space and a shared laundry room. Each unit features a private balcony. The original building was renovated and a large two story addition was built in 2010 which included the two apartments and an addition to the commercial space. There is parking for 2/3 cars tandem style on the side of the building. This versitile property is a rare find.

Just Listed! 37 Seaside South Court $1,725,000 🌴 Luxury Coastal Living at Seaside Residences!Enjoy breathtaking Atlanti...
10/01/2026

Just Listed! 37 Seaside South Court
$1,725,000

🌴 Luxury Coastal Living at Seaside Residences!
Enjoy breathtaking Atlantic Ocean views from this beautifully furnished 4-bedroom, 4-bath townhome in an exclusive gated community. Spanning four levels, this exceptional property features a private elevator, six balconies, a rooftop deck, a chef’s kitchen, and an attached garage.
With a private garden patio, outdoor shower, and access to the community pool, this home offers the perfect blend of luxury, comfort, and island living. 🌊
📲 Contact the Key West Sisters for more details or to schedule a private showing!

Just Sold! 1124 Watson Street, Key West $1,150,000 Welcome to Key West! 🌴🏡It all started at an open house and after the...
10/01/2026

Just Sold! 1124 Watson Street, Key West
$1,150,000

Welcome to Key West! 🌴🏡
It all started at an open house and after the house hunting journey we finally found them their own slice of paradise! 🌺
We’re so excited for our buyers and can’t wait to see them enjoy all that Key West has to offer. Cheers to new beginnings and island living! 🥂

Just Listed! 20 Calle Uno $1,100,000Rare opportunity to build new on an oversized waterfront lot in the Florida Keys. Si...
09/23/2026

Just Listed! 20 Calle Uno $1,100,000

Rare opportunity to build new on an oversized waterfront lot in the Florida Keys. Situated on a 10,400 square foot lot the property already has a pool, dock and 10Klb. boat lift in place giving you a great head start on creating your own home on the water. Plans have already been completed for a 3 bedroom 3 bathroom home designed for the property, with renderings available to help bring the vision to life. Build new without having to start completely from scratch while still having the opportunity to select finishes and make the home your own. Permit on hand. With plenty of outdoor space, direct access to the water and boating right from your backyard this is a unique opportunity to create a new waterfront home in the Keys.

Contact us for more information

Think you know Key West? 🌴From historic homes to cigar factories, there’s always something new to discover. How many of ...
09/22/2026

Think you know Key West? 🌴
From historic homes to cigar factories, there’s always something new to discover.
How many of these did you already know? 👀

Address

520 Southard Street
Key West, FL
33040

Telephone

+13053952540

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