Buying a Home on Maryland's Eastern Shore

Whether you are after a waterfront home on the Chester River, a historic house in downtown Chestertown, a farm in Kent County or a weekend place in Rock Hall, buying on the Shore is different from buying anywhere else. I have spent my whole life here, and my job is to help you find the right property and get it to the closing table without surprises.

Why buyers work with me

  • Local knowledge you can't find online. I grew up on the banks of the Chester River and know the towns, the creeks and the back roads in between, from Rock Hall and Chestertown to Centreville, Easton and St. Michaels.
  • A legal background on your side. I am a licensed attorney and a former law clerk for the Circuit Court of Kent County. Contracts, disclosures and title questions get careful attention, and I explain them in plain English.
  • Waterfront, farms, land and in-town homes. Each comes with its own questions, and I know which ones to ask before you make an offer.
  • A trusted local team. I will connect you with lenders, home inspectors, well and septic inspectors, surveyors and title companies who know the Shore.

What to know before you buy here

  • Waterfront property: Water depth at the pier, shoreline condition and Chesapeake Bay Critical Area rules can all affect how you use the property and what you can build near the water. We look at these early, before you fall in love with a view.
  • Well and septic: Many homes outside town limits run on a private well and septic system, so those inspections matter as much as the home inspection.
  • Farms and land: Zoning, perc tests and any agricultural preservation easements shape what a property can be used for and what it is worth.
  • Older and historic homes: Many of the Shore's best homes are a century old or more. We plan inspections accordingly, and in a historic district we check what review applies before you plan exterior changes.

How it works

  1. We talk about your goals - where, what kind of property, your timeline and budget.
  2. You get pre-approved so your offer is taken seriously. I can introduce you to local lenders.
  3. We search and tour - including homes that fit your criteria the moment they hit the market.
  4. We write a strong offer backed by recent comparable sales.
  5. Inspections and negotiation - I coordinate inspections and negotiate repairs or credits on your behalf.
  6. Closing - I stay on top of the lender, title company and paperwork until you have the keys.

"He is kind, courteous, and knowledgeable about the Eastern Shore." - Christopher, buyer

Ready to start looking?

Use the search on this page to browse homes for sale, or create a custom market report to see what is active, under contract and sold in the area you are considering.

Contact me or call (410) 708-3924 and let's talk about what you are looking for.

Header photo: Shore Studios

Newest Homes for Sale in Kent County

305 Roosevelt Dr, Chestertown
$40,000
Level and cleared building lot in an established community. Public water and sewer available. Law Firm of Shaw and Crowson P.A. in Salisbury preferred for settlement.

305 Roosevelt Dr, Chestertown

Listing courtesy of Taylor Properties. Contact:

104 Maple Ave, Chestertown
$595,000
GUIDED TOUR: MONDAY, NOVEMBER 30, 2026 BEGINNING PROMPTLY AT 11:30 AM List price is opening bid at online auction to be conducted on auctioneer's website. Online Auction Only! Bidding begins Saturday, November 28 and ends Thursday, December 3, 2026 at 1:00 PM. Exceptional Multi-Family Investment Opportunity in Chestertown! Introducing 104 Maple Avenue, a 6-unit apartment building ideally located in Kent County's desirable Chestertown area. This income-producing property seamlessly blends modern finishes with practical functionality, making it an outstanding addition to any investment portfolio. Building is fully Rented (per seller) (rental information forthcoming) Making this an exceptional opportunity for investors seeking strong cash flow and long-term appreciation. Conveniently situated near Washington College, University of Maryland Medical Center, & downtown Chestertown's restaurants, shops, waterfront, and local amenities, the location further enhances its desirability for tenants. Whether you're expanding your real estate portfolio or acquiring a high-performing multi-family asset, 104 Maple Avenue represents a rare opportunity to own a updated six-unit building in one of Kent County's most charming and sought-after communities. Features and Highlights: • (6) Apartments • Thoughtfully Updated & Well Maintained Building • Units refreshed as new tenants are placed. • Stabilized Asset in a Prime Location • 7 Electric Meters • 7 Electric Panels • 3 Forced Hot Air Units • 7,296± SF Building • 8± Onsite Parking Spaces Property Breakdown: Main Level -Central A/C -Forced Hot Air Heat Unit 1 3 Bedrooms, 2 Full Bathrooms Unit 2 2 Bedrooms, 1 Full Bathroom Second Level -Mini Split A/C & Heating System(s) Unit 3 2 Bedrooms, 1 Full Bathroom Unit 4 2 Bedrooms, 1 Full Bathroom Third Level -Central A/C -Forced Hot Air Heat Unit 5 2 Bedrooms, 1 Full Bathroom Unit 6 2 Bedrooms, 2 Full Bathrooms Lower Level Unfinished Basement housing utilities & storage space. The information contained herein was obtained from sources deemed to be reliable, but is offered for informational purposes only. Neither the auctioneer or the owner make any representations or warranties with respect to the accuracy of information. Note: Photos of Unit 4 and Unit 6 were taken prior to tenant move-in date. Currently, 6 out of 6 units are occupied. Rental information forthcoming Diligence Package: A copy of the purchase and sale agreement, lead certificates and assorted addenda are located in the documents section. In order to gain access, you must create a free account as well as accept a non-disclosure agreement.

104 Maple Ave, Chestertown

Listing courtesy of Alex Cooper Auctioneers, Inc.. Contact:

7570 Muirfield Dr, Chestertown
$895,000
4 Beds ⋅ 3 Baths
Elegant Golf Course Living on Maryland’s Eastern shore. Experience the understated elegance of Eastern Shore living in this beautifully crafted, custom-built residence overlooking the 10th tee and fairway of the Chester River Yacht & Country Club. Set on 1.45 acres of thoughtfully landscaped grounds in the desirable Prestwick community, this exceptional property offers privacy, timeless craftsmanship, and the ease of single-level living. Custom-built by Alton Darling, the approximately 2,500-square-foot home features an inviting, open floor plan with hardwood floors, elegant crown molding, and generously proportioned rooms designed for comfortable everyday living and effortless entertaining. The spacious primary suite provides a peaceful retreat with two walk-in closets and a beautifully appointed bath featuring dual vanities with quartz countertops, an oversized walk-in shower. Two additional bedrooms, thoughtfully situated in a separate wing, offer privacy for family and guests. A formal dining room, breakfast room, and versatile office or 4th bedroom space provide flexibility for today’s lifestyles. The kitchen features granite countertops, updated appliances, and convenient access to the home’s gathering spaces. Freshly painted interiors and numerous system improvements further enhance the property’s appeal. Beyond the interiors, the home’s setting truly distinguishes it. A screened porch overlooks mature landscaping and the picturesque golf course, creating an inviting place to enjoy morning coffee, entertain friends, or simply appreciate the peaceful surroundings. A new hot tub and outdoor gathering area offer additional opportunities for relaxation. An attached two-car garage, generous storage, and extensive mechanical and safety improvements complete this thoughtfully maintained residence. Appliances 2024, washer/dryer 2025 More upgrades in the document section.

7570 Muirfield Dr, Chestertown

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

818 High St, Chestertown
$3,300,000
Prime Commercial Opportunity in Chestertown!! The Brian E. Bainbridge Health Building is a prominent, three-story commercial property offers 23,000 square feet of versatile space perfectly situated on High Street. Known locally as the home of the premier Aqua Fit Health Center, this highly functional multi-floor building features an excellent mix of large-scale operational facilities and multiple private office suites. The ground level boasts extensive infrastructure, including a custom-built aquatic center with a heated saltwater pool, expansive weight/cardio rooms, and physical therapy areas. The upper floors offer a flexible layout of professional office spaces, ideal for medical practices, wellness professionals, or traditional corporate tenants. Complete with an elevator, high-visibility street presence, and a dedicated customer/tenant parking lot, this unique asset is a turnkey opportunity for an investor or an owner-user looking to establish a major presence in Kent County.

818 High St, Chestertown

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

4020 Eastern Neck Rd, Rock Hall
$799,000
4 Beds ⋅ 2 Baths
This charming traditional home, originally built in 1957 was renovated around 2000. It offers a blend of classic appeal and modern comfort. Spanning about 3,300 square feet, the spacious layout invites you to create lasting memories. Wood and ceramic tile flooring throughout provide a cozy atmosphere. The expansive outdoor space offers endless possibilities. Currently in ag use, the 25 acres at the rear of the property could remain in ag use as tilled land and/or be used for hunting or as a horse farm. With ample room to customize, this home is a canvas for your personal touch. Located in Kent County, you'll enjoy a peaceful retreat while still being close to local amenities. This property is not just a house; it's a place where you can truly feel at home. Don't miss the opportunity to make this inviting space your own! This property is being sold as-is.

4020 Eastern Neck Rd, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

111 Kent St S, Chestertown
$450,000
2 Beds ⋅ 3 Baths
Nestled in the heart of the Chestertown Historic District, this exquisite residence offers a harmonious blend of traditional charm and modern luxury. Built in 2008, this detached home stands as a testament to meticulous craftsmanship and thoughtful design, ensuring an exceptional living experience. Step inside to discover an open floor plan that invites natural light to dance across the spacious interiors. The heart of the home features a cozy gas fireplace, perfect for creating warm, inviting gatherings. The well-appointed kitchen is a culinary enthusiast's dream, equipped with high-end appliances including a built-in range, microwave, and dishwasher, all seamlessly integrated for both functionality and style. The stacked washer and dryer add convenience, making laundry days a breeze. With two generously sized bedrooms and two and a half elegantly designed bathrooms, this home provides ample space for relaxation and rejuvenation. Each bathroom boasts modern fixtures and finishes, ensuring a spa-like experience at home. The attic space while unfinished, has the ability to be finished for additional living space, if desired. The exterior of the property is equally captivating, featuring beautifully maintained sidewalks and exterior lighting that enhances the home's curb appeal. Enjoy serene evenings on the private patio, where you can unwind and soak in the tranquil surroundings. The lot, spanning 1,330 square feet, offers a manageable outdoor space that complements the busy lifestyle of today's homeowner. Located in a vibrant community, this residence is not just a home; it's a lifestyle. The Chestertown Historic District is renowned for its rich history and picturesque streets, providing a unique backdrop for your daily life. Enjoy leisurely strolls through charming neighborhoods, explore local boutiques, or indulge in the culinary delights of nearby restaurants. This property is more than just a dwelling; it's an opportunity to embrace a luxurious lifestyle in a historic setting. With its impeccable condition and high-end features, this home is ready to welcome you into a world of comfort and elegance. Don't miss your chance to own a piece of this exclusive community-schedule your private tour today and experience the allure of this remarkable residence for yourself.

111 Kent St S, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

403 Calvert St, Chestertown
$135,000
3 Beds ⋅ 2 Baths
INVESTOR OPPORTUNITY! Come see this 3-bedroom, 1.5-bath townhome offering great potential to add to your portfolio! Recent improvements include drywall replacement, newly renovated bathrooms, light fixtures, fresh paint, trim, new wall to wall carpet, and LVP flooring. Buyers should independently verify achievable rents, however it should be noted recently rented townhomes in the area have ranged from $1,800-$2,000. Conveniently located near Washington College, Chestertown's shops, restaurants, and local amenities. Independent appraisal on file showing strong ARV potential. Property is being sold strictly as-is.

403 Calvert St, Chestertown

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

201 Garland Way, Chestertown
$375,000
4 Beds ⋅ 3 Baths
Discover a prime investment opportunity in the sought-after Coventry Farms subdivision! This charming Colonial-style home, built in 2010, boasts 2,886 square feet of potential, featuring 4 spacious bedrooms and 2.5 bathrooms. With a good property condition, this residence is a blank canvas ready for your personal touch or strategic upgrades, ensuring a strong return on investment. The property includes a walkout basement with outside entrance, offering additional space that can be transformed into a rental unit or recreational area, significantly increasing its value. The cozy gas fireplace adds warmth and charm, making it an inviting space for future tenants or buyers. Situated on a generous 0.27-acre corner lot, this home provides ample outdoor space for entertaining or future enhancements, such as landscaping or outdoor living areas. The attached garage and driveway parking for four vehicles enhance convenience, appealing to a broad range of potential renters or buyers. With a low association fee covering common area maintenance, you can enjoy hassle-free ownership while benefiting from the community's amenities. The location offers easy access to local attractions, ensuring high demand for rental opportunities. Invest in a property that not only promises comfort and style but also the potential for significant financial returns. This home is a great way to buy low and make it your own. Certainly is not beyond homeowner fixes. Don't miss out on this exceptional opportunity to grow your real estate portfolio in a thriving neighborhood!

201 Garland Way, Chestertown

Listing courtesy of ERA Martin Associates. Contact:

108 N Water St, Chestertown
$1,125,000
5 Beds ⋅ 4 Baths
This 1925 classic colonial, three story residence, with both front and back gardens, is uniquely situated in the center of the favored 100 block of North Water Street, in historic Chestertown. The formal main entry, with dual brick steps approaches a generous landing, faces away from the street. At first a curiosity until you learn that a prominent family discovered the architectural plans for their "dream house" would not fit horizontally to face the prized road. During its' 100-plus years of life, the front porch (or was it the side?) was converted to a remarkable library, with requisite bookcases, and enjoys light from three sides. The formal parlor, with wood-burning fireplace and reclaimed 19th century moldings and mantle, is left of the straight-through center hall with classic black and white porcelain tiles. The intimate, yet well-proportioned dining room enhances the exceptional flow of the first-floor public rooms. A discreetly positioned powder room and butler's pantry with window and original cabinetry is conveniently placed before entering the large and sunny kitchen with premium custom cabinetry, appliances and finishes from a 2012 renovation. Two distinct patios, one screened and accessed from the dining room and the other from kitchen, overlook the large, rear garden with mature trees and landscaping. The center stairs, with a palladium window bathing light onto the steps, takes you to the first of two oversized landings that have served many lifestyle-uses over the years. The water view primary suite was renovated in 2022 by locally acclaimed Taylor Loughry LLC and boasts a timeless, luxurious aesthetic with custom built closets and Waterwork bath fixtures. Two additional bedrooms and refreshed bath with Restoration Hardware finishes, occupy the second floor. The third floor, with its own generous landing gives access to an ensuite bedroom with walk-in windowed closet (perfect for a future cedar lined closet) and a substantial sized fifth bedroom or multi-purpose space facing the Chester River and exquisite neighboring architecture. Rear yard might accommodate a pool.

108 N Water St, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

5705 Walnut St, Rock Hall
$425,000
3 Beds ⋅ 2 Baths
Close to the Beach, Restaurants, and Marinas in Rock Hall This well-loved and nicely cared-for solid brick rancher sits on a quiet street, offering the perfect blend of peaceful living and incredible convenience. The property features excellent curb appeal, mature landscaping, ample parking, and an oversized detached concrete garage built to match the house. It is completely ready for its next owner to move right in and make it their own. Comfortable Living & Layout • Open Kitchen & Dining: The heart of the home features a generous open kitchen and dining area, creating a wonderful space for meals and gathering. • All-Season Room: Located right off the dining area, the sun-filled all-season room expands your living space year-round. • Living Room: A cozy living room features a classic wood-burning fireplace that provides warmth and charm for the fall and winter seasons, along with a roomy bow window that lets in plenty of natural light and offers great space for plant lovers. • Bedrooms & Baths: The single-level floor plan includes three bedrooms, one full bathroom, and one half bath. • Den & Mudroom: A separate den offers flexible space, while a large utility room serves as a functional laundry, mudroom, and extra storage area. • Flooring: Beautiful hardwood floors run throughout most of the home, complemented by durable tile in select areas. Perfect Rock Hall Location Situated on a quiet, low-traffic street, this location is ideal for enjoying everything the area has to offer: • Walking distance to the beach, quaint shops, local restaurants, and marinas. Community pool is only minutes away if you choose to get a quick cool-down. • An easy, flat area for riding bikes and getting your daily walks in. • A spacious yard featuring mature landscaping. Whether you are looking for a full-time residence or a cozy, low-maintenance getaway for weekends and holidays, this solid brick home is a must-see. Additional Note Home is being sold as is. The backyard features an established concrete pool that has been in place for years and well-enjoyed. For informational purposes, the seller has a current estimate for you to repair the concrete pool or, if a pool isn't on your list, an estimate to fill it in.

5705 Walnut St, Rock Hall

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

7545 Quaker Neck Rd, Chestertown
$175,000
3 Beds ⋅ 1 Baths
Needs work. Sold as is

7545 Quaker Neck Rd, Chestertown

Listing courtesy of Thurston Wyatt Real Estate, LLC. Contact:

12035 Galena Rd, Massey
$365,000
3 Beds ⋅ 2 Baths
Enjoy the charm of country living in this 3-bedroom, 2-bath rancher situated on just over an acre in Massey! Offering convenient one-level living, this home has a rustic, cozy feel with vaulted ceilings, distinctive Scotch Pine wood from Finland in the living room, and a pellet stove that creates a warm and inviting atmosphere. Step outside to enjoy the deck and above-ground pool, perfect for relaxing and making the most of your outdoor space. One of the property's standout features is the impressive 24' x 32' insulated pole building/shop, complete with 100-amp electric, a car lift, and built-in office space—ideal for automotive enthusiasts, hobbyists, contractors, or anyone needing extra workspace and storage. The 75-inch TV in the shop and car lift convey with the sale. Additional peace of mind comes from the fully encapsulated crawlspace with a dehumidifier. The living room couches also convey. With room to enjoy the outdoors, a functional workshop, and the convenience of one-level living, this property offers plenty of possibilities. Home also has Starlink for Internet and equipment stays with property/Talkie is also available. Well pump and pressure tank replaced September, 2026. Property is being sold strictly AS IS. Shared driveway and existing right-of-way access for the farm.

12035 Galena Rd, Massey

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

Start Your Search

How much is your home worth?

Get instant property value now!