Megan McDowell Realtor

10/31/2026

Trick-or-treating in Old Town tonight? Click the link to map your route. 🎃

Old Town's Halloween trick-or-treat map. See which porches are welcoming trick-or-treaters, add your house, map your route.

10/23/2026

10/17/2026

OPEN HOUSE
Saturday, October 17 I 11am-2pm
119 Simonton Street, Key West, FL

Experience modern luxury in the heart of Old Town Key West at 119 Simonton Street-an exceptional end-unit townhome in the exclusive Old Town Villas community.

Step inside to discover:
✔️4 Bedroom / 4 Bathroom
✔️Private elevator servicing all four levels
✔️Custom chef’s kitchen with granite countertops & oversized island
✔️New white oak flooring throughout
✔️Rooftop terrace with sunrise marina views & sunset views toward Mallory Square
✔️Two-car air-conditioned garage
✔️Gated community with a tropical pool & cabana
✔️Just one block from Duval Street, world-class dining, shopping, and the Historic Seaport

Offered at $3,600,000

See you tomorrow!

For more details, or to schedule a private showing:
Megan McDowell
Realtor | Brenda Donnelly Real Estate
305-898-2403
[email protected]

10/04/2026

OPEN HOUSE | Sunday, October 4
12pm-2pm
613 Margaret Street
Old Town Key West, FL

Beyond a classic wooden gate, discover a private island compound where timeless Key West architecture meets beautifully appointed living spaces.

Two distinct residences are connected by lush gardens and winding pathways, with inviting porches, two private heated pools and space to enjoy island life at your own pace. Moments from the Historic Seaport and Duval Street, this property brings together privacy, character and an exceptional Old Town location.

6 Bedrooms | 6.5 Bathrooms
Offered at $5,400,000

Join us this Sunday to explore both residences, stroll the gardens and experience this distinctive property firsthand. No appointment necessary.

Hosted by:
Allison Findlay | 305.395.0615
Megan McDowell | 305.898.2403

Listed by Brenda Donnelly, Broker/Owner
Brenda Donnelly Real Estate

09/25/2026

FOR SALE
1005 Watson St #1 Key West, Florida

Experience the best of Old Town Key West in this beautifully updated 3-bedroom, 2-bath home offering the ease of single-level living.

Inside, you'll find hardwood floors, tall ceilings, French doors, stainless steel appliances, and an inviting open layout filled with natural light. Designed for the Key West lifestyle, the private backyard features a saltwater pool with heater and chiller, outdoor shower, lush tropical landscaping, spacious patio, and two dedicated off-street parking spaces. Offered at $1,575,000

✔ Fully furnished & turnkey
✔ Established monthly vacation rental history
✔ Prime Old Town location
✔ Just minutes to Higgs Beach, Duval Street & the Historic Seaport

Whether you're looking for a successful investment property, a full-time residence, or your own island getaway, this home checks every box. Schedule your private showing today!

Megan McDowell
Realtor |
305-898-2403
[email protected]

09/20/2026

OPEN HOUSE | Sunday, September 20 11AM-1PM
1701 Laird Street
Old Town Key West, FL

A contemporary tropical retreat where lush landscaping, modern architecture and a private pool create your own secluded Key West oasis. This is more than a home; it is a sophisticated, high-design haven just steps from the ocean.

🛏 2 Beds | 🛁 2 Baths
💰 $2,900,000

Hosted by:
Megan McDowell | 305.898.2403

Listed by Brenda Donnelly, Broker/Owner
Brenda Donnelly Real Estate

09/17/2026

OPEN HOUSE | Friday, September 18 12pm-2pm
530 Catherine Street
Key West, FL

Awarded the Florida Keys Preservation Star, this meticulously restored single-family home offers an enchanting blend of historic Key West charm, modern luxury, and high-yield investment potential.

Holding a coveted TRANSIENT LICENSE allowing profitable nightly rentals, this turnkey Old Town sanctuary sits just a half-block from world-famous Duval Street while enjoying a prime position near boutique shops, fine dining, and the Southernmost Point.

3 Bedrooms | 3.5 Bathrooms
Offered at $3,700,000

Whether retained as a high-performing vacation rental with proven revenue projections or enjoyed as a private island getaway, this home offers a rare chance to own a piece of Key West.

Hosted by:
Megan McDowell | 305-898-2403

Listed by Brenda Donnelly, Broker/Owner
Brenda Donnelly Real Estate

09/17/2026

OPEN HOUSE | Friday, September 18 12pm-2pm
530 Catherine Street
Key West, FL

Awarded the Florida Keys Preservation Star, this meticulously restored single-family home offers an enchanting blend of historic Key West charm, modern luxury, and high-yield investment potential. Holding a coveted TRANSIENT LICENSE allowing profitable nightly rentals, this turnkey Old Town sanctuary sits just a half-block from world-famous Duval Street while enjoying a prime position near boutique shops, fine dining, and the Southernmost Point.

3 Bedrooms | 3.5 Bathrooms
Offered at $3,700,000

Whether retained as a high-performing vacation rental with proven revenue projections or enjoyed as a private island getaway, this home offers a rare chance to own a piece of Key West.

Hosted by:
Megan McDowell | 305-898-2403

Listed by Brenda Donnelly, Broker/Owner
Brenda Donnelly Real Estate