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102 Pine St, Crumpton
$339,900
3 Beds ⋅ 2 Baths
Open House Saturday May 30th 11am -1pm — Stop In and Take a Tour! New Price Alert!! Experience the simple pleasures of one-level living in this stylish rancher on a spacious 1/2 acre corner lot. Built just four years ago!! From morning coffee on the front porch to sunset boat rides on the Chester River (just a couple blocks away!), this home is designed for comfort and convenience. Step inside and you will see the well-designed open floor layout with beautiful LVP flooring, a sleek white kitchen boasting SS appliancNew Price Alert!!!es and granite countertops, a spacious living room and an adjoining dining area adorned with tons of natural light. The sleeping zone features a primary bedroom with an ensuite bathroom. there's also two additional bedrooms with a shared full bathroom and a separate laundry room. You’ll love the designer lighting, sun-drenched rooms, and the privacy of a fenced backyard. Within close proximity to shopping, dining and the delights of downtown Chestertown... Easy access to Route 301...20 minutes to Delaware...30 minutes to Bay Bridge...Why wait to build when you can own this nearly new and perfectly priced home?? Some images have been virtually staged and digitally enhanced.

102 Pine St, Crumpton

Listing courtesy of Clark & Co Realty, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

34 Queen Anne Way Unit F, Chester
$338,000
1 Beds ⋅ 1 Baths
Rare Opportunity in Queen’s Landing with Stunning Chester River Views Welcome to one of the few oversized one-bedroom condos in the highly desirable Queen’s Landing community. Immaculately maintained and thoughtfully designed, this larger-than-average unit offers gorgeous views of the Chester River and the added benefit of expanded living space rarely found in one-bedroom layouts. The larger floor plan provides an oversized patio perfect for relaxing or entertaining, along with additional storage both inside the unit and outside. Inside, the spacious layout allows for comfortable seating in the living room, a more functional kitchen with extra usable space, and a walk-in closet off the primary bedroom, making everyday living feel effortless and organized. Properties of this size in Queen’s Landing rarely come available, making this an exceptional opportunity whether you're searching for a weekend getaway, investment property, or low-maintenance year-round residence. For ease of mind, all appliances and HVAC system are less than 5 years old. Residents enjoy access to a variety of resort-style amenities including: • The Queen’s Landing Clubhouse • Outdoor pool and pickleball courts • Marina and kayak launch area • Scenic jogging and walking trails • Restaurants and waterfront dining within walking distance Located on Kent Island, this property offers the perfect blend of relaxation and convenience. Enjoy easy access to shopping, entertainment, and outdoor recreation, all just minutes from the Bay Bridge for a convenient commute to Annapolis, Baltimore, or Washington, D.C. Don’t miss this rare opportunity to own one of Queen’s Landing’s larger one-bedroom units with breathtaking water views and an easy, coastal lifestyle.

34 Queen Anne Way Unit F, Chester

Listing courtesy of Cross Street Realtors LLC. Contact:

Selling Office: Corner House Realty.

209 3rd St, Crumpton
$337,500
3 Beds ⋅ 2 Baths
Motivated Seller!!! Loan is assumable for a qualified veteran. Opportunity to own a beautiful rancher on 0.46 ac in the town of Crumpton. This home was built in 2021. It has been maintained, and kept meticulously. It compares nicely to new construction. The front porch welcomes you to a well-designed open concept 3 BR, 2 full bathrooms home. Natural light illuminates the living space. There is no shortage of amenities: an updated, modern kitchen with SS appliances, under cabinet lighting, granite countertops, whole house sprinkler system. The laundry room adjoins the kitchen. This home offers plenty of room for all of your outdoor activities. It's two blocks to the boat ramp (Chester River). Easy commute to Route 301, Chestertown, Middletown, and the Bay Bridge. This is a one of a kind listing. Don't wait. Schedule your showings today!

209 3rd St, Crumpton

Listing courtesy of EXP Realty, LLC. Contact:

Selling Office: Long & Foster Real Estate, Inc..

104 Walnut St, Church Hill
$335,000
4 Beds ⋅ 2 Baths
Some homes simply have a feeling you can't recreate, and this is one of them. Rich in character and timeless craftsmanship, this beautifully maintained home blends historic charm with thoughtful updates, creating a warm and inviting place you'll love coming home to. Original hardwood floors, glass doorknobs, skeleton keys, classic swinging doors, and elegant architectural details tell the story of a home built to stand the test of time, while an updated bathroom and refreshed kitchen provide the comforts of everyday living. Designed with both gathering and quiet moments in mind, the spacious layout offers generously sized rooms filled with natural light. The oversized screened porch is the perfect extension of the home, inviting you to enjoy morning coffee, evening conversations, or simply unwind while overlooking the expansive backyard with plenty of room for gardening, entertaining, pets, or play. A full unfinished basement offers abundant storage and room for future possibilities. Located in the heart of Church Hill, this is more than just a house. It's an opportunity to own a home filled with warmth, history, and character that's becoming increasingly difficult to find.

104 Walnut St, Church Hill

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: Chesapeake Real Estate Associates, LLC.

103 Oregon Rd, Stevensville
$334,900
2 Beds ⋅ 1 Baths
Welcome home to this charming two-bedroom cottage in the water-privileged community of Kent Island Estates, where affordability meets coastal charm! Enjoy a relaxed lifestyle with nearby water access, community amenities, and all the comforts of a cozy home. Featuring beautiful Pine and Red Oak flooring, a cozy pellet stove, and a custom-milled barn door (BR), this home is full of warmth and character. Step outside to an inviting outdoor living space with a fenced backyard, spacious patio and two storage sheds for extra storage. A rare opportunity to own an affordable slice of waterfront community living, whether you're seeking a full-time residence, weekend getaway, or investment property. Outdoor enthusiasts will appreciate being just steps from the South Island Trail, a scenic 7-mile trail stretching from Matapeake State Park to the Romancoke Fishing Pier, offering endless opportunities for walking, running, and biking. Conveniently located just minutes from Blue Heron Golf Course, waterfront dining, marinas, and all that Kent Island has to offer. Paid members of Kent Island Estates enjoy access to two private waterfront parks and a community beach along the Chesapeake Bay, perfect for soaking in stunning sunsets, fishing, kayaking, or simply embracing the waterfront lifestyle. Kent Island Estates has a Voluntary HOA $30/year and Beach/Recreation Fee $40/year. Mandatory Fee is $10 /Year for Roads Maintenance Don't miss your chance to enjoy the best of Eastern Shore living at an exceptional value!

103 Oregon Rd, Stevensville

Listing courtesy of Rosendale Realty. Contact:

Selling Office: Redfin Corp.

204 Ringneck Ct, Chester
$326,000
3 Beds ⋅ 4 Baths
Price improvement just in time for the spring market! Come see all of amazing amenities this water privileged community has! Enjoy the boating, pool, restaurants and Cross Island trail all within walking distance of this great home! Lovely 3 level townhome in the water oriented community of Bayside Marina offering 2/3 bedrooms and 3 full and one half baths. This multifunctional unit can be two bedrooms up and one down or use the downstairs room with a full bath as a tv or relaxing/entertaining area. Walk out to the patio and enjoy views of the community pond or walk to the pool, community clubhouse or gym. The current owners upgraded the kitchen in 2022 with quartz countertops, new lighting and new gas stove and refrigerator. The dishwasher is brand new/never used. The roof was replaced in 2023 and most of the unit has just been painted and professionally cleaned. Carefree living on the island. It doesn’t get any better than this!

204 Ringneck Ct, Chester

Listing courtesy of Cummings & Co. Realtors. Contact:

Selling Office: Redfin Corp.

109 Parma Rd, Chestertown
$325,000
3 Beds ⋅ 2 Baths
Welcome to 109 Parma Road in family-friendly Chester Harbor. This well-maintained home is located on a quiet street and has three generously sized bedrooms with hardwood flooring and 2 full bathrooms. An upgraded kitchen featuries granite countertops, SS appliances, and solid wood cabinets with quiet-close drawers. Spacious living room off the kitchen and dining room combo. Spacious and private backyard is perfect for dogs and children. Mature oak trees provide lots of cool shade. Recent upgrades include: bathroom vanities, ceilings fans, light fixtures, microwave, interior paint, driveway crushed run. Chester Harbor is a quiet community with water access to the Chester River for just $15 per year and NO HOA. 5 minutes to downtown Historic Chestertown. Founded in 1706, Chestertown sits on the banks of the Chester and is home to Washington College. Enjoy the historic homes, local shopping, restaurants, art galleries, and waterfront parks. Chestertown is home to many festivals, an award-winning weekly Farmer's Market. Enjoy country living on the Eastern Shore. Less than one hour to Annapolis. Much more info and professional photos coming soon. Stay tuned!

109 Parma Rd, Chestertown

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

Selling Office: Coldwell Banker Realty.

640 Main St, Church Hill
$320,000
3 Beds ⋅ 2 Baths
Modern updates. Timeless character. The best of both worlds awaits at 640 Main Street in the heart of Church Hill. Beautifully updated and move-in ready, this charming home offers the warmth, character, and craftsmanship buyers love, paired with the modern finishes and functionality they need. From the moment you step inside, you'll appreciate the bright, inviting spaces, gorgeous hardwood floors, and thoughtful updates throughout. The renovated kitchen serves as the centerpiece of the home, featuring updated cabinetry, modern finishes, ample storage, and plenty of room to gather with family and friends. Updated bathrooms add style and convenience, while spacious living areas provide the perfect balance of comfort and character. Offering 3 generously sized bedrooms and 2 full bathrooms, this home provides plenty of space for everyday living. The cozy pellet stove creates a warm and welcoming atmosphere, while abundant natural light fills the home throughout the day. Additional features include a versatile mudroom and bonus flex space that can easily serve as a home office, hobby room, playroom, or additional storage area. Outside, you'll find one of the property's most desirable features—a rare half-acre lot right in town. Whether you're entertaining, gardening, relaxing around a fire pit, or simply enjoying the open space, the backyard offers endless possibilities that are difficult to find in today's market. The welcoming front porch adds even more charm and provides the perfect place to enjoy your morning coffee or unwind at the end of the day. Conveniently located just minutes from Route 213, Route 301, Centreville, and Chestertown, you'll enjoy easy access to shopping, dining, marinas, local events, and everything Maryland's Eastern Shore has to offer. Combining modern updates, spacious living, a half-acre lot, and timeless character, 640 Main Street offers a unique opportunity to enjoy the best of small-town living without sacrificing today's comforts.

640 Main St, Church Hill

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: Samson Properties.

54 Queen Caroline Ct, Chester
$319,000
2 Beds ⋅ 3 Baths
DON"T MISS OUT on this super deal!! Owners have lowered the price by $10,000 and are willing to look at offers! Nothing to do but move in! Be in this spring to enjoy all that summer offers on the shore!! This roomy 2 bedroom, 2.5 bathroom end unit has been completely painted in a beautiful neutral shade and has new carpet throughout the living areas and new vinyl flooring in the kitchen. A propane fireplace highlights the great room turning chilly nights into cozy nights! On warm days, enjoy relaxing in the enclosed patio/porch or just being outside. Being an end-unit it offers lots of privacy. Any and all assessments have been paid by the owner, so you are ready to go and enjoy all the amenities that Queens Landing is known for...beautiful waterside pool, the club house with a party room, racquet ball court, exercise room, tennis courts, jogging trail, and more! Close to the cross-island trail, the Matapeake Dog Park, restaurants, schools, library...it is a wonderful place to live! Whether you are looking for a place to use as a vacation or weekend home, or as a year-round residence, this will suit both needs. It's situated in a great location...minutes to the Bay Bridge for any commuters to the western shore, and many airports, and an easy drive to the MD and DE beaches! Note: 4 pictures have been Virtually Enhanced!

54 Queen Caroline Ct, Chester

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

Selling Office: Benson & Mangold, LLC.

501 Teal Ct, Chester
$310,000
5 Beds ⋅ 4 Baths
Welcome to easy, waterfront-inspired living in the heart of Chester! This beautifully maintained first-floor condo at 501 Teal Ct offers the perfect blend of comfort, style, and convenience—plus peaceful views of the community pond right from your backyard. Step inside to find gorgeous hardwood floors flowing throughout the main living space, anchored by a cozy propane fireplace—perfect for those crisp Shore evenings. The updated kitchen is a true standout, featuring stunning granite countertops, a designer backsplash, and stainless steel appliances, making it as functional as it is eye-catching. Enjoy your morning coffee or unwind at the end of the day with tranquil pond views—no stairs, no hassle, just easy living. Located in the sought-after Bayside community, residents enjoy access to a clubhouse, fitness center, and pool, plus direct proximity to the Cross Island Trail for walking, biking, and soaking in that Kent Island lifestyle. All of this just minutes to local dining, shopping, and the Chesapeake Bay Bridge—making commuting or a quick getaway a breeze. If you’ve been waiting for low-maintenance living with high-impact style… this is it.

501 Teal Ct, Chester

Listing courtesy of Samson Properties. Contact:

Selling Office: Realty Navigator.

302 Merganser Ct Unit A, Chester
$300,000
2 Beds ⋅ 2 Baths
Welcome to coastal living in this beautifully updated first-floor, end-unit condo, offering the perfect blend of comfort, convenience, and resort-style amenities in one of Kent Island's most sought-after communities. With no stairs to navigate and handicap-accessible features, this home provides effortless everyday living while enjoying the added privacy and abundant natural light that only an end unit can offer. The beautifully updated kitchen features new quartz countertops, backsplash, a breakfast bar, newer stainless steel appliances, and abundant cabinetry, making it as functional as it is stylish. The adjoining dining area flows seamlessly to the private deck through sliding glass doors, bringing the outdoors in and making entertaining a breeze. Fresh paint, carpet, kitchen appliances, HVAC and washer/dryer are all less than 4 years old. The spacious primary suite serves as a relaxing retreat with a large walk-in closet and private ensuite bath. A second generously sized bedroom offers exceptional flexibility for guests, a home office, or family visits, while elegant plantation shutters add timeless charm and character to both bedrooms. Life at Bayside is about much more than the home itself. Residents enjoy a truly maintenance-free lifestyle, with exterior maintenance and community upkeep handled by the condominium association, leaving more time to enjoy everything Kent Island has to offer. Community amenities include a clubhouse, swimming pool, fitness center, tennis courts, beautifully landscaped grounds, and Castle Marina just a short walk away. Outdoor enthusiasts will appreciate being only steps from the Cross Island Trail, offering miles of scenic walking and biking paths showcasing the natural beauty of the Chesapeake Bay. Ideally located near waterfront dining, shopping, and local attractions, this home also provides easy access to Route 50 and the Chesapeake Bay Bridge, international airports and coastal beaches, making commuting and travel exceptionally convenient. Where every day feels like a vacation—and the only thing left to maintain is your schedule.

302 Merganser Ct Unit A, Chester

Listing courtesy of Keller Williams Flagship. Contact:

Selling Office: Redfin Corp.

102 Bobbitt Ct, Stevensville
$300,000
2 Beds ⋅ 2 Baths
AGENTS - PLEASE VIEW AGENT REMARKS IN BRIGHT MLS. Just in time for spring! This exquisitely renovated 2-bedroom, 2-bathroom home offers the ideal space to bring your dream lifestyle to life. This property is perfect for the weekend warrior, first time buyer or someone downsizing! Boasting an open-concept design, it features a spacious living room, dining area, and a modern kitchen complete with quartz countertops, stainless steel appliances, and stylish white shaker cabinets. Enjoy brand-new luxury vinyl plank flooring throughout, freshly painted interiors, and a newly constructed front porch deck. With its thoughtful details and inviting layout, this home has everything you need and more. https://homesale.plus/Listing/Details/8269880. Please schedule all showings online via Showing Time. Offers will be accepted through Tuesday, March 24, 2026 at 5:00 pm. AT SELLER'S DISCRETION, AN OFFER MAY BE ACCEPTED AT ANY TIME.

102 Bobbitt Ct, Stevensville

Listing courtesy of Keller Williams Legacy. Contact:

Selling Office: Douglas Realty LLC.

154 Longfellow Dr, Chestertown
$300,000
3 Beds ⋅ 1 Baths
Located in the water-oriented community of Chester Harbor just outside of historic Chestertown, 154 Longfellow Drive offers the ideal blend of convenience and Eastern Shore living. This single-level home is situated on a cleared and fenced 0.34 acre-parcel and a voluntary HOA fee provides access to the community boat ramp and waterfront park. Less than a mile and a half from Route 213, enjoy efficient commuting and quick access to Chestertown, Church Hill, Centreville, Easton, and Kent Island. Inside the home, enjoy an updated full bath, a new HVAC system and well pump, a six year old septic system (flushed in 2025), as well as a large, partially finished basement - perfect for storage.

154 Longfellow Dr, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

Selling Office: CR Realty.

550 Bolton Woods Rd, Sudlersville
$300,000
3 Beds ⋅ 2 Baths
Welcome to 550 Bolton Woods Road in Sudlersville, Maryland — a stunning new construction rancher that perfectly blends modern comfort with peaceful country charm. This beautifully built home features 3 spacious bedrooms, 2 full bathrooms, and an attached 1-car garage, offering both functionality and style. Step inside to an open floor plan filled with natural light and luxury vinyl plank flooring throughout, creating a seamless flow from room to room. Whether you're hosting guests or enjoying a quiet evening in, the layout is designed for effortless living. The large front porch sets the tone for relaxed mornings and rocking chair evenings, all with a serene farm backdrop that truly captures the essence of rural living. Set on a quiet country road, this property delivers the tranquility you crave with the convenience of brand-new construction. If you’ve been searching for space, simplicity, and style all in one place — this is your moment.

550 Bolton Woods Rd, Sudlersville

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: Chaney Homes, LLC.

102 Merganser Ct Unit 102, Chester
$297,000
2 Beds ⋅ 2 Baths
Island living anyone? Make a splash in the community pool, fitness center & tennis- just steps from your door! Spacious, GROUND/MAIN-LEVEL coastal inspired condo in coveted Bayside on Kent Island. This 2 BR/2 Bath home is greeted with sunny patio area overlooking a lush lawn and water views. Inside you will notice plenty of windows, abundance of natural light, and an open-concept design that creates the perfect mood for that "laid back" coastal lifestyle you crave. This home features a well designed kitchen with granite counter tops and eating bar. There is plenty of space for entertaining! Relax in the large living/family room with a cozy fireplace and spacious dining area that opens to a private balcony. The large, primary bedroom suite features a spacious walk-in closet and full bath. The second bedroom is bright with light conveniently located next to the second full, hall bath. There is so much to do living the Bayside lifestyle! Your new community offers a beautiful pool, clubhouse, fitness center, and tennis courts, all just a few steps from your door...and stay healthy, happy, and fit taking your morning walk along the Cross Island Trail, offering miles of nature's beauty along the pathways.

102 Merganser Ct Unit 102, Chester

Listing courtesy of Chaney Homes, LLC. Contact:

Selling Office: Real Broker, LLC - Chester.

240 Round Top Rd, Chestertown
$295,000
3 Beds ⋅ 2 Baths
Welcome home...spacious rancher nestled on a beautiful, private 1-acre lot. This home offers 3 bedrooms, 2 full bathrooms, a cozy light filled living room, and an eat-in kitchen perfect for everyday living. The full unfinished basement provides endless possibilities for additional living space, a workshop, or extra storage. Step outside to enjoy the peaceful backyard, featuring a privacy-fenced yard and a paved driveway. The roof, siding, and windows were replaced approximately 10 years ago, offering added value and peace of mind. Stay warm and keep utility costs down during the colder months with both a pellet stove in the living room and a wood-burning stove in the basement. With just a little TLC and updating, this home could be everything you've been looking for. Offering privacy, space, and endless potential, it's a great opportunity to make it your own. Located just minutes from the historic waterfront town of Chestertown, you’ll enjoy charming boutiques, local restaurants, seasonal festivals, the popular Farmers Market, and plenty of ways to experience the scenic beauty of the Chester River. The area perfectly captures the charm and lifestyle of Maryland’s Beautiful Eastern Shore. NOTE: Virtually staged/digitally enhanced photos. Images are for illustrative purposes and may not represent the property's current condition or actual furnishings.

240 Round Top Rd, Chestertown

Listing courtesy of Clark & Co Realty, LLC. Contact:

Selling Office: Long & Foster Real Estate, Inc..

313 Oak St, Centreville
$293,000
2 Beds ⋅ 1 Baths
Discover the charm of this delightful bungalow nestled in the heart of Centreville Heights. This beautifully maintained 2-bedroom, 1-bathroom home boasts hardwood floors that flow seamlessly throughout, creating a warm and inviting atmosphere. The eat-in kitchen is perfect for those early morning coffees or evening cocktails, including a cooktop, wall oven, dishwasher, and refrigerator, perfect for culinary enthusiasts. Step outside to enjoy your private deck, ideal for enjoy those beatiful mornings or evening gatherings. The spacious lot offers ample outdoor space, complemented by street lights that enhance the neighborhood's inviting ambiance. A convenient shed provides additional storage for your gardening tools or outdoor equipment. The interior features include an attic for extra storage, a cozy dining area, and energy-efficient double-hung windows that fill the home with natural light. The basement, equipped with a drainage system and sump pump, offers potential for additional living space or a workshop. Located in a vibrant community, this home is just minutes away from local parks, providing endless opportunities for outdoor activities and relaxation. The neighborhood is known for its friendly atmosphere and accessibility to essential public services. This property is not just a house; it's a place to create lasting memories. Embrace the lifestyle you've always wanted in Centreville Heights!

313 Oak St, Centreville

Listing courtesy of Cummings & Co. Realtors. Contact:

Selling Office: Eastern Shore Real Estate, LLC.

509 Tal Ct Unit E, Chester
$290,000
2 Beds ⋅ 2 Baths
Welcome to your perfect island retreat in the sought-after waterfront community of Bayside! This beautifully positioned end-unit condominium offers the ideal blend of comfort, convenience, and breathtaking scenery. Enjoy tranquil pond views with a charming fountain, along with glimpses of the Chester River and marina—all from the privacy of your own deck. Whether you're sipping your morning coffee or unwinding at sunset, this peaceful setting is one you'll love coming home to. Inside, you'll find a spacious open floor plan enhanced by soaring cathedral ceilings, creating a bright and airy atmosphere. Featuring two generously sized bedrooms and two full bathrooms, this home is designed for easy, comfortable living. The fully equipped kitchen flows seamlessly into the living and dining areas, making it perfect for entertaining or simply enjoying everyday life. Best of all, low-maintenance living means more time to enjoy everything this exceptional community has to offer. Take a leisurely stroll to nearby restaurants, keep your boat at the marina just moments away, or explore scenic bike trails and experience the relaxed charm of island living. Bayside residents also enjoy outstanding amenities, including a clubhouse with a fitness center, party room, two expansive balconies overlooking the resort-style pool, and tennis courts. This is your opportunity to own a piece of paradise on the island. Schedule your private showing today—this exceptional home won't last long!

509 Tal Ct Unit E, Chester

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: Realty Navigator.

517 Round Top Rd, Chestertown
$289,000
3 Beds ⋅ 1 Baths
An exceptional opportunity to own this Single Level 3 bedroom 1 full bathrooms Ranch Style Home at a GREAT price nestled on an adorable lot. No need to worry about climbing stairs, everything is located on one floor. the interior showcases contemporary finishes and a thoughtful layout that maximizes both style and functionality. The bathroom has been tastefully refreshed, the home has been freshly painted with LPV flooring and carpet throughout. This home offers the ultimate in conveniences local public and private golf courses outlets Close Proximity to the Chester River, fine dining and easy access to major highways. Don't miss out on the chance to create your dream space in this prime Chestertown location! NEW HVAC SYSTEM TO BE INSTALLED

517 Round Top Rd, Chestertown

Listing courtesy of Keller Williams Flagship. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

901 Chester River Dr, Grasonville
$287,000
2 Beds ⋅ 1 Baths
Come and check out this affordable & charming water view cottage nestled in the sought after water privileged Chester River Beach community. This remodeled & inviting home offers the perfect balance of comfort, convenience & lifestyle with plenty of room to add on or up & expand to capture water views. This property is on public sewer. You’ll love spending relaxing mornings or evenings on the front patio or watch the sun set from the waterfront park/boat launch just steps away. Wonderful location, just minutes away from local parks, marina’s, cross island trail, hospitals, restaurants, shopping, recreational activities & convenient to route 50. Sold As Is at this amazing price.

901 Chester River Dr, Grasonville

Listing courtesy of Taylor Properties. Contact:

Selling Office: Benson & Mangold, LLC.

1905 Bayside Dr, Chester
$285,000
2 Beds ⋅ 2 Baths
INVESTORS!! THIS COULD BE YOUR NEXT PROJECT!! Estate Sale – Peaceful Tranquility on the Eastern Shore There’s something special about living near the water—the smell of the bay, the calm in the air, and the sound of birds all around you. This brick rancher in the desirable Marling Farms community is right in the center of it all. With views of Crab Alley Creek and located within the Chester River watershed, the setting offers the peaceful lifestyle so many seek on the Eastern Shore. While the home needs a little TLC, it’s graciously waiting for its next homeowner to bring their vision to life. The property is being sold AS-IS, and no repairs will be made—BUT- it’s the perfect opportunity to add your own special touches. The home does feature a newer roof.... update to suit your taste-- Highlights include a welcoming front porch, attached two-car garage, and a driveway that accommodates additional parking. Inside, you'll find a spacious living room with a fireplace (ambiance for a snow-fall) and walls of windows that allow natural light to pour in while showcasing the surrounding beauty. .. and a view of the Crab Alley Bay is just across the road-- The home also offers an entrance foyer, an eat-in kitchen, and a four-season sunroom overlooking open green space—perfect for relaxing or gathering with family and friends. Situated on a little over a half-acre lot, the backyard offers a blank canvas to create your own outdoor oasis. The home includes one full and one half bathroom, two bedrooms, and a versatile breezeway bonus room currently set up as a club room with a pool table. This flexible space could easily be converted into additional living space or a bedroom— There is also a laundry closet and ample storage throughout. Marling Farms is a water-oriented community surrounded by natural beauty, offering three beach areas with playgrounds and covered picnic spaces. You don’t have to be a crabber or fisherman—but those hobbies certainly fit right in here! Enjoy nature walks, fishing, or relaxing at the community waterfront. Located just minutes from waterfront restaurants, shopping, and everyday conveniences on Kent Island-- Its the home you’ve always wanted in a water community—You just have to get here

1905 Bayside Dr, Chester

Listing courtesy of Cummings & Co. Realtors. Contact:

Selling Office: RE/MAX Leading Edge.

1025 Dundee Ct, Chester
$280,000
3 Beds ⋅ 3 Baths
Estate Sale! Incredible opportunity to own one of the best values on Kent Island. Priced well below its potential, this 3-bedroom, 2.5-bath Dundee Harbor townhome offers approximately 1,400 square feet with an excellent upside. An updated home in the community sold for $365,000 in 2025, and this property offers outstanding potential for investors, flippers, or buyers looking to build equity. Enjoy relaxing or entertaining on the rear deck, then take advantage of Dundee Harbor's water privileges on Piney Creek, including a private community pier for fishing, kayaking, paddleboarding, crabbing, or simply enjoying the waterfront. Just minutes from Kent Narrows, you'll love the waterfront restaurants, marinas, boat ramps, tiki bars, live entertainment, and Chesapeake Bay lifestyle. Conveniently located near shopping, everyday conveniences, and Route 50, this home offers an easy commute while delivering the relaxed Eastern Shore lifestyle buyers are looking for. Whether you're searching for an investment property, primary residence, or weekend retreat, this Estate Sale is an opportunity you won't want to miss. Schedule your showing today!

1025 Dundee Ct, Chester

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: Douglas Realty LLC.

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