Key West Sisters

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

✨ **SOLD!** ✨This one was extra special for us. ❤️ Our seller first came into our lives years ago as a tenant and we’ve ...
09/03/2026

✨ **SOLD!** ✨

This one was extra special for us. ❤️ Our seller first came into our lives years ago as a tenant and we’ve stayed in touch ever since. Fast forward to today and we had the privilege of helping her sell her home and move on to her next chapter.

We’re so grateful for the relationships this business brings us and for clients who continue to trust us through the years. Congratulations to our sellers! 🏡🥂

Ever wonder how Key West’s streets got their names? 🌴🛣️From Duval and Whitehead to Fleming, Eaton and Caroline, the stre...
08/18/2026

Ever wonder how Key West’s streets got their names? 🌴🛣️

From Duval and Whitehead to Fleming, Eaton and Caroline, the streets we walk, bike and drive every day are filled with pieces of Key West history.

Many were named after prominent figures, early residents and families who helped shape the island into the place we know today. 🏡🌺

Next time you’re wandering through Old Town, take a look at the street signs—you might be passing a little piece of Key West history without even realizing it!

Want to learn the stories behind some of Key West’s most familiar street names?

🌴 Read the full blog at KeyWestSisters.com

✨ SOLD | 1613 Josephine Street✨Another Key West property SOLD!🏡🌴We successfully got 1613 Josephine Street SOLD in just 2...
08/17/2026

✨ SOLD | 1613 Josephine Street✨

Another Key West property SOLD!🏡🌴

We successfully got 1613 Josephine Street SOLD in just 29 days for 94% of the asking price, followed by a smooth and quick closing!

In today’s market the right pricing, marketing, and strategy matter. We’re so happy to have helped our sellers get this one across the finish line! 🔑✨

Thinking about selling your Key West property? We’d love to help you put together a strategy that gets results.

Key West Sisters | Preferred Properties

KeyWestHomes SoldInKeyWest PreferredProperties

Not to be dramatic… but we are sooooooo obsessed with this house in Key West. 🌴💗And honestly, can you blame us?📍 2412 Li...
08/14/2026

Not to be dramatic… but we are sooooooo obsessed with this house in Key West. 🌴💗

And honestly, can you blame us?

📍 2412 Linda Avenue is the kind of home that makes you want to cancel your plans and never leave. Completely renovated, totally private, and sitting right on the water, this tropical retreat has all the Key West vibes we love.

✨ 2 bedrooms + office/optional 3rd bedroom
🌊 Direct waterfront
🌴 Lush, private tropical landscaping
💦 Heated & chilled saltwater pool + spa
🍹 Outdoor kitchen made for entertaining
🚿 Dreamy indoor/outdoor primary bath with an open-air shower
🔑 Turnkey + move-in ready

It feels like your own little private resort tucked away in Key West — and yes, we’re obsessed.

Want to see it in person? Send us a DM and we’ll get you inside. 🩷🌴

Key West Sisters | Preferred Properties Key West

✨ PRICE IMPROVEMENT ✨New price, same incredible opportunity! 🏡🔑This property just became even more enticing. Whether you...
08/14/2026

✨ PRICE IMPROVEMENT ✨

New price, same incredible opportunity! 🏡🔑

This property just became even more enticing. Whether you’ve been watching it or you’re seeing it for the first time, now is the perfect time to take another look.

📍 3612 Sunrise Drive
💰 NOW OFFERED AT $2,499,000.

Ready to see it in person? Send us a DM to schedule your private showing! 📲

Multiple Offers. One More Win. 🏆Just listed. Multiple offers. Under contract and closed in just 10 days!Even more specia...
08/13/2026

Multiple Offers. One More Win. 🏆

Just listed. Multiple offers. Under contract and closed in just 10 days!

Even more special: this is the 3rd investment property our client has purchased with us, and their 4th purchase overall. And here’s the part we love most every single investment property has been a multiple offer situation, and we’ve won every time. 🙌🏼

There’s nothing better than earning a client’s trust again and again and helping them build their investment portfolio along the way.

Another one closed. Another win for our client. 🥂

RealEstateInvesting KeysRealEstate

08/07/2026

Some of the best moments in Key West happen outside. 🌺🚿
An outdoor shower after a day on the water, surrounded by tropical blooms, is one of those little luxuries that makes island living so special.
Dreaming of a home with its own private oasis? We’d love to help you find it. 🌴🏡

6 things that mean something when your from Key West 🧐…
07/31/2026

6 things that mean something when your from Key West 🧐…

A rare opportunity to own one of Key West’s most extraordinary historic homes. ✨ 103 Front Street, Key West, FL 33040 $6...
07/28/2026

A rare opportunity to own one of Key West’s most extraordinary historic homes. ✨

103 Front Street, Key West, FL 33040 $6,850,000

Built in the early 1900s and meticulously restored, 103 Front Street blends timeless architecture with modern luxury. Soaring ceilings, custom woodwork, sun-filled living spaces, and a thoughtfully designed floor plan make this home as functional as it is stunning.

Set on two lots in the heart of Old Town, the property features a resort style pool and spa, covered loggia, lush tropical landscaping, and off-street parking perfect for enjoying the ultimate Key West lifestyle.

Historic charm. Exceptional craftsmanship. Unmatched location. This is truly a one-of-a-kind estate.

KeyWestLiving IslandLuxury

From the iconic Hemingway Look-Alike Contest to the spirited Running of the Bulls parade, this beloved annual celebratio...
07/23/2026

From the iconic Hemingway Look-Alike Contest to the spirited Running of the Bulls parade, this beloved annual celebration brings the island’s literary history to life with unforgettable traditions, live entertainment, and community spirit.

Some people travel here for Hemingway Days. Others are fortunate enough to call Key West home.

Thinking about making the island your home? We’d love to help.

Address

520 Southard Street
Key West, FL
33040

Telephone

+13053952540

Website

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