Lisa Raffetto - Coldwell Banker Chesapeake

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Lisa Raffetto - Coldwell Banker Chesapeake Specializing in 18th and 19th century houses, farms and waterfront properties!

Background before real estate, grew up in Baltimore County, graduated from Calvert, Garrison Forest School, and Bennett College. Associate in Applied Arts degree majoring in fashion design and retailing, elementary school teacher, rector’s wife, and two sons.

1989 licensed in real estate with Long and Foster; Associate Broker and GRI with Cooper Barroll, O’Connor Piper and Flynn, Coldwell Banker Residential Brokerage and The Hogans Agency.

1994 Rookie of the year for Kent County Board of Realtors and awarded the GRI certification,

1996 Earned the Associate Brokers designation,

1999 Realtor of the year for BAAR,

2000 Distinguished Sales Associate,

Active in real estate industry matters, including Chairman of the Meals and Programs Committee. Chairman of the Education Committee for 8 years, through the year 2000.

2000 President Bay Area Association of Realtors, serving 3 terms currently on membership committee;

1999-2005 served as a Director of The Maryland Association of Realtors. Served on Fair Housing and Leadership committees

Top Lister and Top Producer for 10 years

Notes like this mean so much to me. Connie, thank you for your kind words and for trusting me over these past three mont...
10/07/2026

Notes like this mean so much to me. Connie, thank you for your kind words and for trusting me over these past three months. It’s been a pleasure working with you, and I’m so grateful you took the time to send this thoughtful note.

10/03/2026

For sale: 2 bed, 2 bath, 1,098 SQFT Condo. Second story, waterfront condo in historic Chestertown... $489,000.

New Listing and Open House TODAY from 11am-1pm.Second story, waterfront condo in historic Chestertown. Comes with a priv...
10/03/2026

New Listing and Open House TODAY from 11am-1pm.

Second story, waterfront condo in historic Chestertown. Comes with a private boat slip at the end of the dock. 2 bedrooms and 2 full baths. Spacious patio with a stunning view of the Chester River. One of the most coveted streets in historic Chestertown!

For sale: 2 bed, 2 bath, 1,098 SQFT Condo. Second story, waterfront condo in historic Chestertown... $489,000.

09/11/2026
06/24/2026

A rare piece of Chestertown history, right in the heart of downtown.

Join Lisa Raffetto for a tour of 407 High Street, also known as Highcroft — a beautifully preserved in-town property built in 1780/1840 with the charm of the Historic District and thoughtful modern updates throughout.

With 3 bedrooms, 4.5 baths, over 3,000 sq. ft., a gourmet kitchen, gorgeous wood floors, curved staircase, off-street parking, a 2-car garage, solar array, and EV charger, this home is truly one of a kind.

Just steps from Chestertown’s restaurants, shops, bars, and the Chester River — this is historic downtown living at its best.

Listing Info: https://lisaraffetto.com/listing/MD/Chestertown/407-High-Street-21620/226985247

📍407 High Street, Chestertown, MD
Listed by Lisa Raffetto, Coldwell Banker Chesapeake Real Estate Company

Reach out to Lisa for more information or to schedule a private showing.

Lisa Raffetto
Coldwell Banker Chesapeake Real Estate Company
114 S. Cross St, Chestertown, MD
Office: 410-778-0330
www.lisaraffetto.com

Thanks for the great review!
06/19/2026

Thanks for the great review!

🏡 Open House in Historic Chestertown!Join Lisa Raffetto this Saturday and tour this beautifully maintained home in the h...
05/29/2026

🏡 Open House in Historic Chestertown!

Join Lisa Raffetto this Saturday and tour this beautifully maintained home in the heart of downtown Chestertown.

📍 407 High Street, Chestertown, MD
📅 Saturday, May 30
⏰ 10:00 AM – 1:00 PM
💰 Offered at $828,000
Listing Link: https://lisaraffetto.com/listing/MD/Chestertown/407-High-Street-21620/226985247

Featuring:
✔️ 3 Bedrooms
✔️ 3.5 Bathrooms
✔️ 3,047 Square Feet

Enjoy the charm of historic Chestertown with spacious living areas, timeless character, and a location that puts you just steps from downtown shops, restaurants, and the waterfront.

Whether you're actively searching for a new home or simply curious about one of Chestertown's beautiful properties, stop by and take a look.

Lisa Raffetto, Realtor
Coldwell Banker Chesapeake Real Estate Company
Multi award winning agent, Associate Broker
GRI (Graduate Real Estate Institute)
Global Luxury Specialist
Direct: 410-708-0174
Office: 410-778-0330
Email: [email protected]
www.lisaraffetto.com

This Memorial Day, we pause to remember and honor the brave men and women who gave everything for our country. Their sac...
05/25/2026

This Memorial Day, we pause to remember and honor the brave men and women who gave everything for our country. Their sacrifice is the reason we enjoy the freedoms we often take for granted.

Today, we remember. 🇺🇸

Stop by before 1pm to see this historic gem on High Street!
05/09/2026

Stop by before 1pm to see this historic gem on High Street!

Join me this Saturday, May 9th from 10 AM to 1 PM for an open house at 407 High Street in Chestertown.

Located in the heart of historic downtown Chestertown, this 3 bedroom, 3.5 bath home offers over 3,000 square feet of living space and timeless Eastern Shore charm.

407 High Street, Chestertown, MD
Offered at $828,000
https://lisaraffetto.com/listing/MD/Chestertown/407-High-Street-21620/226985247

Join me this Saturday, May 9th from 10 AM to 1 PM for an open house at 407 High Street in Chestertown.Located in the hea...
05/06/2026

Join me this Saturday, May 9th from 10 AM to 1 PM for an open house at 407 High Street in Chestertown.

Located in the heart of historic downtown Chestertown, this 3 bedroom, 3.5 bath home offers over 3,000 square feet of living space and timeless Eastern Shore charm.

407 High Street, Chestertown, MD
Offered at $828,000
https://lisaraffetto.com/listing/MD/Chestertown/407-High-Street-21620/226985247

Address

114B S. Cross Street
Chestertown, MD
21620

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