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

🌴 Poolside Paradise... but which one would you choose? 🤔🏖️ Waterfront luxury at 3612 Sunrise Drive with endless water vi...
06/12/2026

🌴 Poolside Paradise... but which one would you choose? 🤔

🏖️ Waterfront luxury at 3612 Sunrise Drive with endless water views and a resort-style pool?

OR

🌺 Tropical retreat vibes at 2412 Linda Avenue with a stunning outdoor living space designed for entertaining and island living?

Both homes are available now in Key West, and both offer incredible outdoor spaces that make every day feel like a vacation.

👇 Tell us in the comments:
🌊 Team Sunrise Drive
or
🌴 Team Linda Avenue

Which pool would you be spending your summer in?

Just Listed!  1613 Josephine Street $925,000 Furnished and move in ready, this beautifully appointed Midtown Key West ha...
06/05/2026

Just Listed!

1613 Josephine Street $925,000

Furnished and move in ready, this beautifully appointed Midtown Key West half townhouse offers the perfect blend of comfort and island living. The open floor plan features high ceilings, abundant natural light, and a spacious living, dining, and kitchen area, along with a convenient half bath on the main level. Upstairs the private bedroom suites provide comfortable accommodations and separation from the living space. Enjoy plenty of room for outdoor entertaining, relaxing, and dining al fresco, along with ample off street parking ...a rare Key West convenience. Centrally located near beaches, restaurants, shopping and all that Key West has to offer this property is ideal as a primary residence, vacation home or investment opportunity.

06/01/2026
SOLD for $13,500,000 🎉This iconic Key West property has always been a vibe: filled with great music, unforgettable memor...
05/31/2026

SOLD for $13,500,000 🎉

This iconic Key West property has always been a vibe: filled with great music, unforgettable memories, and the energy that makes our island so special.

We’re excited to see the next chapter unfold as Smokin’ Tuna takes the helm.

The vibes aren’t going anywhere... they’re just getting turned up a notch. 🎶🍹🌴

Congratulations to everyone involved in this exciting transition. Stay tuned, Key West... the best is yet to come.

SOLD ✨ 1708 Laird St. closed at $1,870,000 in just 56 days.A beautifully turnkey Key West home that captured attention w...
05/26/2026

SOLD ✨ 1708 Laird St. closed at $1,870,000 in just 56 days.

A beautifully turnkey Key West home that captured attention with its quality, furnishings, and move-in-ready appeal. Congratulations to our sellers and the new owners beginning their next chapter in paradise 🌴

Thinking about buying or selling in Key West? Let’s connect.

05/24/2026

Still living in this night 🥂✨🖤

10+ years of Key West Sisters What a fabulous night filled with so much love, gratitude, laughter, and support. We are i...
05/23/2026

10+ years of Key West Sisters

What a fabulous night filled with so much love, gratitude, laughter, and support. We are incredibly thankful to our family, friends, clients, vendors, and community who have been part of this journey with us.

Angela & Jenny started Key West Sisters over 10 years ago with a focus on relationships, community, and truly caring for the people we work with. A decade later, that mission remains exactly the same and we are so grateful to still be doing what we love with all of you by our side.

Thank you for believing in us, supporting us, and celebrating this milestone together. Cheers to the memories made and the years ahead 🥂

Price Adjustment‼️Now offered at $1,799,999Waterfront, turnkey, and completely private 2412 Linda Avenue delivers the ul...
05/20/2026

Price Adjustment‼️Now offered at $1,799,999

Waterfront, turnkey, and completely private 2412 Linda Avenue delivers the ultimate Key West lifestyle. This fully renovated tropical retreat is designed for effortless indoor outdoor living offering the perfect blend of entertaining space and serene seclusion.The home features 2 bedrooms plus a flexible office/optional third bedroom with a bright open layout and a sunken living and dining area overlooking the pool and water through expansive windows.The primary suite is a standout, featuring a walk in closet and a spa inspired indoor outdoor ensuite with a dual head open air shower surrounded by lush palms. Outside the property lives like a private resort complete with a heated and chilled saltwater pool/spa, outdoor kitchen, and mature tropical landscaping. With direct water frontage you can easily enjoy the natural surroundings right from your backyard. Extensively improved and move in ready this home offers a seamless combination of comfort, style, and functionality.

🏝️ INVESTMENT OPPORTUNITY IN THE HEART OF OLD TOWN 🏝️Introducing 800 Elizabeth St. + 624 Petronia St — a rare triplex op...
05/19/2026

🏝️ INVESTMENT OPPORTUNITY IN THE HEART OF OLD TOWN 🏝️

Introducing 800 Elizabeth St. + 624 Petronia St — a rare triplex opportunity offering 7 bedrooms and 6 bathrooms in one of the most sought-after neighborhoods in Key West.

This unique property is more than just real estate… it’s a solution for local business owners, investors, and anyone looking for flexible island living. Live in one unit while renting the others, create employee housing, or build long-term investment income in Old Town Key West.

✔️ Triplex configuration
✔️ Prime Old Town location
✔️ Ideal for workforce housing
✔️ Income-producing potential
✔️ Rare multi-unit opportunity
✔️ X Flood Zone

With workforce housing becoming one of the biggest challenges in Key West, properties like this are becoming increasingly valuable for restaurant owners, hospitality groups, contractors, marine businesses, and investors alike.

We just featured the FULL BLOG on our website where we break down why this property is such a smart long-term investment opportunity.

👉 Search “Key West Sisters 800 Elizabeth” on Google or visit
KeyWestSisters.com to read the full feature.

MultiFamilyInvestment KeyWestSisters InvestInKeyWest OldTownLiving KeyWestHomes 

05/17/2026

🏡 OPEN HOUSE TODAY | 11AM–1PM
📍3612 Sunrise Dr, Key West

Come tour this waterfront Key West retreat featuring 3 bedrooms, 2 bathrooms, a brand new pool, oversized canal-front lot, and room for your boat 🌴⚓️

Major upgrades are already complete including a new roof, all new windows, updated electrical, fresh paint, and more. Move right in and start enjoying island living.

Offered at $2,590,000

Stop by today and see why this Sunrise Drive property is such a rare opportunity in Key West ☀️

Hosted by the Key West Sisters
Angela & Jenny | Preferred Properties

Address

520 Southard Street
Key West, FL
33040

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