Bridge across calm water at sunset, viewed from a rocky shoreline.

October 2026 Newsletter

Chesapeake Real Estate Associates, LLC

DISCOVERING WHERE YOU BELONG - LET US HELP YOU FIND YOUR DREAM HOME!


Offices in Queen Anne's, Talbot and Kent Counties

Sunset over calm water, with a long bridge on the horizon and rocky shoreline.

FEATURED LISTINGS

Two-story brick and siding home with a front-facing garage, landscaped lawn, and covered entry.

1717 Harbor Drive

Chester, MD 21619


$1,250,000

Discover exceptional waterfront living on picturesque Cox Creek. Beautifully renovated approximately four years ago, this move-in-ready home combines modern updates with the timeless appeal of Maryland's Eastern Shore. Offering 3 bedrooms, 2.5 baths, and a highly desirable main-level primary suite, the thoughtfully designed layout provides both comfort and functionality.


Yellow colonial-style house with green shutters and a red door behind a white picket fence.

106 Queen Street S

Chestertown, MD 21620


$799.900


Currently operating as one of the most successful Airbnbs in the area with a strong rental history ($32K in bookings last year!), this property offers the best of both worlds--an ideal vacation home and a turn-key income-producing investment. Furniture is negotiable.115 Congressional Drive

Stevensville, MD 21666

COMING SOON

Aerial view of a large yellow house with a wraparound porch, swimming pool, and wooded grounds.

403 Chesterfield Avenue

Centreville, MD 21617


$699,000

Step into a piece of Centreville's history with this distinctive Victorian, originally built in 1875, where timeless architectural charm meets thoughtful modern updates! Situated on approximately half an acre in the heart of town, this one-of-a-kind property welcomes you with a massive wraparound front porch and charming porch swing, the perfect place to relax and take in the beauty of your surroundings.

Aerial view of a home and red outbuilding surrounded by open lawn and woodland.

132 Deep Shore Road

Denton, MD 21629


$629,000


Welcome to 132 Deep Shore Rd--an inviting homestead set on more than 3 acres of beautifully maintained gardens, thoughtfully designed outdoor spaces, and versatile outbuildings. From greenhouse and herb beds to a dedicated drying room and casual nooks for lounging, every corner invites you to savor the seasons.

White two-story home with dormer windows, broad lawn, and mature autumn trees.

201 Winchester Drive

Centreville, MD 21617


$609,900


Welcome to this spacious Cape Cod situated on a generous corner lot in Centreville's Hunters Ridge neighborhood. Offering four bedrooms, two full and two half baths, and multiple living spaces, this home provides a flexible layout with plenty of room to gather, entertain, work from home, or spread out.

Two-story beige home with a covered porch, broad lawn, and detached garage.

329 Union Church Road

Chestertown, MD 21620


$549,900


Situated on just over an acre, this 4-bedroom, 2.5-bath home offers 2,464 square feet of living space, a paved driveway, attached garage, and a large detached pole barn with loft--providing plenty of room for storage, hobbies, a workshop, or all the extras.


Two-story light-sided home with blue shutters, a covered porch, and a broad green lawn.

7884 Laurel Lane

Denton, MD 21629


$549.900


Offered for the first time, this custom-built home is nestled on 2 private acres in the highly sought-after water access community of Forest Landing, conveniently located between historic downtown Denton and Easton. Beautifully updated and move-in ready, this property offers 3 bedrooms, 2.5 baths, and a finished bonus room, providing flexible space for a home office, gym, playroom, or guest accommodations.


Two-story brick house with a red front door, broad green lawn, and mature trees.

161 Greenwood Creek Road

Queenstown, MD 21658


$519,000


TWO LOTS FOR SALE with two different tax Ids/addresses. The home sits on 1.16 arces and the additional adjacent lot sits on 1.10 acres which was graded as a Par 3 golf course. The second lots tax ID:1805020174, address is 165 Greenwood Creek Rd, Queenstown, MD 21658.


Aerial view of a two-story white house with an attached garage, surrounded by mature trees.

225 Autumn Lane

Centreville, MD 21617


$499,000


Welcome to this lovely 4-bedroom, 2.5-bath home tucked away on a quiet cul-de-sac in the private community of Heritage, right in the heart of Centreville! Inside, you'll find beautiful hardwood floors throughout much of the main living area, along with carpeting that is only 1 year old. 

Gray two-story house with a covered porch, front lawn, and concrete walkway.

214 Belvedere Avenue

Centreville, MD 21617


$475,000


Discover the space, convenience, and potential this 4-bedroom, 3-bathroom Centreville home has to offer. Situated on an expansive 0.45-acre lot, this property provides plenty of room to spread out and create a home that fits your lifestyle. 



Wooded single-story home with a detached garage and curving driveway.

11598 Malvern Lane

Cordova, MD 21625


$459,000


Nestled in the serene Chapel Woods subdivision, this charming traditional home offers a perfect blend of comfort and functionality. With four spacious bedrooms and two full bathrooms, this residence is designed to meet your needs for both relaxation and entertaining.

White two-story house with black shutters and an American flag; seller financing available.

305 E Water Street

Centreville, MD 21617


$450,000


Well-established commercial property offering exceptional exposure in a sought-after location. The first floor commercial space features about 1800+ sq' separated between a large retail space, office/kitchen , and storage space. The second floor includes a 2-bedroom, 1-bath apartment--ideal for owner occupancy or rental income.

Aerial view of a rural home beside farmland, with wooded acreage and detached outbuildings.

1010 S 2nd Street

Denton, MD 21629


$375,000


Nestled on the edge of town, 1010 S 2nd Street delivers the convenience of in-town living without in-town taxes. Situated on 1.06 beautifully landscaped acres with mature plantings, this 3-bedroom, 2-bath home offers a spacious feel inside and out. Interior features include hardwood, LVP, and tile flooring, along with a cozy pellet stove fireplace insert for efficient heating, complemented by hot water baseboard heat as backup.

Aerial view of a two-story home with a fenced yard and illuminated windows at dusk.

123 Trafford Drive

Chestertown, MD 21620


$370,000


Space, convenience, and value just minutes from downtown Chestertown! This spacious 4-bedroom, 2.5-bath Colonial in Coventry Farms checks the boxes for buyers looking for room to spread out without giving up convenience.


Brick ranch home with landscaped lawn and flagpoles beneath a vivid sunset.

374 Hurtt Avenue

Millington, MD 21651


$359,000


Discover the charm of this beautifully renovated ranch-style home in the Millington community. With 1,801 sq. ft. of exquisite living space, this residence features an open floor plan that seamlessly connects the living, dining, and kitchen areas, perfect for entertaining. Enjoy upgraded countertops, stainless steel appliances, and elegant wood floors throughout.

UNDER CONTRACT

Single-story gray-sided home with a light metal roof, front lawn, and landscaped shrubs.

15395 Oakland Road

Goldsboro, MD 21636


$355,000


Enjoy the freedom of country living on 2 beautiful acres with **no HOA and no restrictions!** This renovated 3-bedroom, 2-bath rancher offers the convenience of one-level living, a spacious lot, and thoughtful updates that make settling in that much easier. 

Single-story white house with a gravel driveway, attached garage, and brick chimney.

29316 Will Street

Easton, MD 21601


$349,000

Welcome to this adorable, move-in ready rancher that perfectly blends comfort, functionality, and style! Nestled in a convenient Easton location, this well-maintained home shines with thoughtful updates throughout.

Step inside to discover a warm and inviting interior, ideal for everyday living or entertaining. Major improvements include a brand-new roof and newer HVAC system, giving you peace of mind for years to come.


Aerial view of a two-story gray home with lit windows, surrounded by mature trees.

306 Caroline Avenue

Ridgely, MD 21660


$320,000


Charming updated Farmhouse style home with hardwood floors throughout and tiled bathrooms. The open kitchen features quartz countertops, a center island for extra prep space and casual dining, stainless steel appliances, and a tile backsplash. 

Single-story gray-sided home with a red front door, broad lawn, and fenced driveway at dusk.

4306 E Pheasant Drive

Hurlock, MD 21643


$299,900


Welcome home to this move-in-ready, 3-bedroom, 2-bath rancher situated on a spacious .92-acre lot! Offering the convenience of one-level living, this home features a desirable split-bedroom floor plan, with the primary bedroom on one side of the living area and two additional bedrooms and a full bath on the opposite side, providing a little extra privacy. Inside, you'll find a comfortable living room, an eat-in kitchen, and a combination of hardwood and carpet flooring. 

Aerial view of a single-story home with a driveway and recreation courts behind it.

101 Parkland Road

Greensboro, MD 21639


$299,000


Just a few months old and ready for you to move right in! This beautifully maintained 3-bedroom, 2-bath rancher offers the ease of one-level living with a bright, open layout and the benefits of a nearly brand-new home--without the wait.



White two-story house with a steep roof, covered porch, and American flag.

105 S 5th Avenue

Denton, MD 21629


$290,000


Step into a charming piece of history with this beautiful Colonial home in the desirable Denton area. Built in 1900, this 2,759-square-foot residence offers the character and craftsmanship of a bygone era while providing the space and conveniences today's buyers desire.


White-sided home entrance with a blue awning, small wooden deck, and concrete patio beside a grassy yard.

533 Gay Street

Denton, MD 21629


$270,000


Investment opportunity! This two-unit duplex offers a functional layout with two separate residences, each featuring 2 bedrooms, 1 full bathroom, a kitchen, and in-unit laundry. The property offers separate entrances for each unit, providing privacy and convenience for occupants. With one unit located on the main level and the second unit upstairs, the setup offers flexibility for investors looking to add a multifamily property to their portfolio.




White single-story house with black shutters, a dark roof, and a broad green lawn.

11167 Oak Lane

Worton, MD 21678


$269,900


Welcome to easy Eastern Shore living in this beautifully updated 3-bedroom, 1-bath home that truly feels like new. Recently updated with a new roof, water heater, HVAC system, stainless steel appliances, luxury vinyl plank flooring, carpet, fresh paint, recessed lighting, and a vapor barrier and insulation in the crawlspace. 

Aerial view of a two-story house with a front porch and warmly lit windows at dusk.

216 S 3rd Street

Denton, MD 21679


$250,000


Why rent when you can own and start building equity and an asset of your own? Priced at just $250,000, this charming home in the heart of downtown Denton offers an affordable opportunity to put your personal touches into a home and make it your own. The main level features a spacious living room with updated flooring, kitchen with separate dining area, office/flex space, mudroom, and a full bathroom, while upstairs you'll find three bedrooms and another full bathroom.




Three-story white-sided townhouse with a blue front door, attached garage, and front lawn.

2516 Westwind Blvd.

Unit TH

Cambridge, MD 21613


$239,900


This three-story townhouse features three bedrooms, two full bath, and a half bath. The main level includes a bonus room which walks out to a beautiful TREK deck and an additional half bath ready for final finishes. This home provides plenty of space and an attached one car garage. Located in Cambridge minutes away from local restaurants, stores, parks, and waterfront. Perfect location for a day trip to the beach as well. Come take a look today!

UNDER CONTRACT

Aerial view of attached townhouses beside a tree-lined street and parking lot at sunset.

200 Brant Way

Cambridge, MD 21613


$220,000


Discover the charm of this beautifully renovated townhouse in the Pintail Landing community. This end-unit home, built in 2005 and thoughtfully updated throughout the years, offers a perfect blend of modern comfort and inviting warmth. Step inside to find a spacious layout featuring three cozy bedrooms and two and a half baths.



White two-story house with black shutters and a covered entry.

310 Park Avenue

Federalsburg, MD 21632


$199,000


This charming farmhouse-style home, built in 1904 has undergone a major renovation in 2026. With 812 square feet of thoughtfully designed living space, this delightful residence features two cozy bedrooms and one and a half bathrooms, making it an ideal retreat for those seeking comfort and style. 

Two-story tan house with a covered front porch, centered between neighboring homes and leafy trees.

313 Washington Street

Cambridge, MD 21613


$185,500


Unlock the potential of this duplex located in downtown Cambridge! Whether you're looking to expand your investment portfolio or generate rental income, this property offers plenty of opportunity. The first unit features 3 bedrooms and 1 full bathroom, while the second unit offers 2 bedrooms and 1 full bathroom, providing flexibility for long-term tenants, owner-occupants, or future rental income.


Are you ready to embark on an exciting journey in the world of real estate? At Chesapeake Real Estate Associates, we invite you to discover your true passion and unlock a realm of endless possibilities for success. Our unique agent-owned model fosters a supportive and collaborative environment, where new agents can thrive alongside experienced mentors. Join our friendly, community-oriented team and experience the difference of personalized service that prioritizes trust and client satisfaction. Together, let's explore the dynamic real estate market on Maryland's Eastern Shore and turn your aspirations into achievements. Team up with us and take the first step towards a fulfilling career in real estate!


Chesapeake Real Estate Associates, LLC

Two people shake hands as one presents a small house model in warm sunlight.

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We live in a beautiful area on the Eastern Shore of Maryland, and we want you to experience that lifestyle as well. Call us today and we can get you started.

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