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29580 Kent Ave, Easton
$462,000
2 Beds ⋅ 2 Baths
Welcome to this beautifully appointed 2 bedroom, 2 bathroom single-level home in the sought-after Easton Club East community, offering natural light throughout. A welcoming foyer sets the tone, with an office/library on the right and dining room on the left, and the living room straight ahead, which impresses with a tray ceiling, crown molding, and classic wainscoting, creating an ideal space for entertaining. The spacious main living area features a vaulted ceiling, cozy gas fireplace, and direct access to the patio, seamlessly blending indoor and outdoor living. The stunning designer kitchen is a true centerpiece, showcasing upgraded quartz countertops, white cabinetry, stainless appliances, and a large center island with designer pendant lighting and counter seating—perfect for casual dining and gathering. The primary suite offers plush carpeting, a generous walk-in closet, and French doors leading to a luxurious ensuite bath complete with a corner soaking tub framed by windows, separate vanities, a step-in shower, and a private water closet. Additional highlights include a 2-car rear-entry garage and a fenced backyard for added privacy and outdoor enjoyment. New roof 2025, kitchen flooring new 2026 as well as new carpeting in the bedrooms and hallway. Residents of Easton Club East enjoy exceptional amenities, including a clubhouse with a ballroom, game room, and fitness center, as well as tennis and pickleball courts and a refreshing outdoor pool. Special note: this property is exempt from the 55++ requirement for residents. Ideally located just minutes from Route 50 and all that Maryland’s Eastern Shore has to offer, this home combines relaxed coastal living with everyday convenience.

29580 Kent Ave, Easton

Listing courtesy of Compass. Contact:

Selling Office: The KW Collective.

29830 Hillary Ave, Easton
$462,000
3 Beds ⋅ 3 Baths
Nestled in the serene Easton Club East/Chesapeake by Del Webb community, this exquisite 3-bedroom, 2.5-bathroom residence is designed for those seeking a refined lifestyle. With a minimum age requirement of 55, this vibrant community offers a perfect blend of comfort and luxury. Step inside to discover a spacious 3,052 sq. ft. layout adorned with elegant crown moldings and wood flooring. The gourmet kitchen, featuring upgraded countertops and stainless steel appliances, invites culinary creativity, while the cozy family room with gas fireplace off the kitchen provides a warm gathering space. Enjoy the convenience of a main-floor laundry and a primary suite complete with bath and walk-in closet. The exterior boasts charming brick and vinyl siding, complemented by an underground lawn sprinkler system. Relax on your private patio or take a leisurely stroll along the community's scenic jog/walk paths. 55+ age-restricted section. The community amenities feature Clubhouse, exercise rooms, ballroom, meeting rooms, library, card and craft rooms, outdoor pool, tennis and pickleball courts, bocce ball, horse shoes, exercise paths, picnic areas and putting green, perfect for socializing or unwinding. With an attached rear-entry garage and a concrete driveway, convenience is at your fingertips. Experience the exclusive lifestyle that awaits in this remarkable home, where every detail has been thoughtfully curated for your comfort and enjoyment. PRIME LOCATION, just minutes to downtown Easton shopping, restaurants, churches and medical facilities. Only 30 minutes to the Bay Bridge, 1.5 hours to Maryland/Delaware beaches and within 1-1.5 hours to Annapolis, Baltimore, Washington DC and international airports.

29830 Hillary Ave, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

29380 Moore Ave, Trappe
$460,000
3 Beds ⋅ 4 Baths
Welcome to 29380 Moore Avenue in Trappe — a charming two-story Cape Cod offering the perfect blend of comfort, versatility, and exceptional workspace/storage opportunities. Inside, the home features an updated kitchen with modern countertops and stainless steel appliances, plus a sliding glass door leading directly to the patio for easy indoor-outdoor living. The spacious main-level primary suite provides convenience and privacy, while an additional full bathroom is located just off the living room for guests. Upstairs, you’ll find two additional bedrooms, a full bath, and a cozy landing area complete with an electric fireplace — ideal as a reading nook, office, or bonus living space. Outside is where this property truly shines. The oversized pole barn garage offers incredible flexibility for hobbyists, collectors, workshop space, or extensive storage needs. Equipped with its own heat pump and central A/C, Rinnai water heater, half bathroom, kitchen area with gas stove/range, refrigerator, and utility sink, the space is ready for a wide range of uses. An additional garage bay features built-in professional kennels with indoor/outdoor access and convenient quick-fill rotating feeders. A huge detached carport provides excellent covered parking for RVs, boats, trailers, or additional vehicles, while the separate shed offers even more storage or potential recreation/hobby space. Conveniently located with quick access to Route 50, this property offers an easy commute to Easton, Cambridge, and surrounding areas while delivering the flexibility and functionality that are hard to find.

29380 Moore Ave, Trappe

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Meredith Fine Properties.

9829 Bantry Rd, Easton
$452,500
3 Beds ⋅ 3 Baths
PROPERTY REDUCED 65,000, since first under contract. Drive down a country lane surrounded by farmland & woods to the lovely neighborhood of Bantry. Enjoy your own 5+acres with a circular driveway & scenic surroundings. Welcome to your single level home w/ full front porch, lots of decking & a warm interior. Gather around the fireplace or enjoy a window filled great room w/ wood burning stove & access to extensive decking which overlooks the landscaped yard, beautiful gardens & trees. Gather around the breakfast counter or sit at the dining room table. Take refuge in one of the 3 bedrooms, including a primary suite with walk-in closet & in suite full bath. Laundry room w/ commode, sink built-ins & closet. Grab your boat, kayak or paddle board & venture down to the community boat ramp & pier. Or walk or bike down & enjoy the views. Downtown Easton, Easton Airport, stores, the new hospital, Rte 50 & the Bay Bridge are just a short ride away.

9829 Bantry Rd, Easton

Listing courtesy of RE/MAX One. Contact:

Selling Office: Meredith Fine Properties.

7220 Fir St, Easton
$452,500
4 Beds ⋅ 3 Baths
Welcome in! Discover the charm of this Colonial home nestled in the desirable Woods at Stoney Ridge. Spanning 2,388 sq. ft., this residence boasts four spacious bedrooms and 2.5 baths, perfect for both relaxation and entertaining. Family room with super efficient pellet stove, formal dining room and living room, powder room, private office/study and centrally located, inviting kitchen present comfortable living.. The kitchen offers, upgraded countertops, a convenient island, and a cozy breakfast area that adjoins family room and overlooks backyard. Stunning entry stairway brings you to the second floor. The primary suite offers generous room space, a soaking tub, walk-in shower and double sinks in the attached bath complemented by ample closet space. Three additional bedrooms, all nicely sized with great natural light and convenient laundry room complete the second floor. Sliding doors from kitchen / family room open to an expansive deck and privacy fenced yard containing hot tub area, children's play area, shop with electric / shelving, additional storage shed and metal gazebo easily covered to provide shade. The backyard overlooks open space highlighting a sense of privacy. Two car attached garage with added storage and easy entry to house. Located on a well elevated lot in a desirable community, with sidewalks and street lights, this home is just minutes from local amenities, parks, and shopping. Roof recently replaced. Don't miss your chance to make it yours!

7220 Fir St, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Douglas Realty LLC.

8737 Harper Way, Easton
$452,500
3 Beds ⋅ 2 Baths
**Red Tag Sales Event now through May 3, 2026! Was $469,990 Now: $464,990! Home must close on or before 6/26/2026.** Check out 8737 Harper Way in Easton, MD, a new ranch home on a corner homesite in Gannon Range. This Azalea home offers three bedrooms, two bathrooms, 9' ceilings and a two-car garage. The welcoming foyer has two coat closets and separates to afford privacy to the two spacious guest bedrooms with closets and the secondary bathroom. The open floorplan features a well-designed gourmet kitchen complete with beautiful quartz countertops, an oversized island, a pantry closet, and stainless-steel appliances. The kitchen is open to the breakfast nook, dining area, and great room making it easy to spend time with friends and family. The large laundry room, tucked between the kitchen and the two-car garage, also features an additional coat closet. The private owner’s suite is a retreat in the back of the home with a spacious bathroom with a luxury shower and a large walk-in closet. Enjoy the private covered porch overlooking the back of the home and the fully sodded and irrigated lawn. This home includes white window treatments and the exclusive Smart Home® package. Pictures, artist renderings, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Image representative of plan only and may vary as built. Images are of model home and include custom design features that may not be available in other homes. Furnishings and decorative items not included with home purchase.

8737 Harper Way, Easton

Listing courtesy of D.R. Horton Realty of Virginia, LLC. Contact:

Selling Office: Non Subscribing Office.

105 Pier, Oxford
$450,000
3 Beds ⋅ 2 Baths
Oxford Retreat with Coastal Appeal! This lovely, bright and airy 3-bedroom, 2- full bath home is located only a block from public beach access. Perfect as a second home or a cozy year-round residence, this charming property offers a warm, inviting atmosphere with solid, 5-inch wide, pine, hardwood floors, sun-filled rooms, and 10-foot ceilings in living room and the private, primary bedroom with en-suite bathroom and walk-in closet. Spacious, fenced lot with mature Oaks providing some shade, backs to Oxford Community Park with sports fields, walking trail, tennis court and EV charging station. Fabulous sunroom and large, composite, rear deck overlooking the park serves as an ideal space for night-time star gazing or entertaining. Located across the street from the wonderful Community Garden and Oxford dog park. There is also an inviting, covered front porch - perfect for relaxing or catching up with neighbors. Just outside of Historic District and close to all town amenities including restaurants, boating, marinas, parks, beaches and Oxford's famous ice-cream shop. Plenty of off-street parking. Detached shed, ideal for storing those kayaks, beach cruisers and beach toys.

105 Pier, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

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

22539 Indian Point Rd, Bozman
$450,000
4 Beds ⋅ 2 Baths
Welcome to 22539 Indian Point Road, a charming Cape Cod set on 2 private acres in the peaceful waterfront community of Bozman. Offering over 1,800 square feet of living space, this 4-bedroom, 2-bath home blends classic Eastern Shore character with versatile indoor and outdoor living. From the moment you arrive, you’ll appreciate the serene setting and timeless curb appeal, complete with a detached barn featuring heat, electric, and a loft—perfect for a workshop, hobby space, storage, or potential studio. Surrounded by nature and open space, this property offers the privacy and flexibility so many buyers are seeking. Inside, the home features a traditional yet functional Cape Cod layout with a warm and inviting feel throughout. The main level offers comfortable living spaces filled with natural light, including a bright sunroom at the rear of the home—an ideal place to relax and take in the peaceful surroundings. Two bedrooms and a full bathroom on this level provide convenience for everyday living or guest accommodations. The kitchen and dining areas flow seamlessly, making the home well-suited for both daily life and entertaining. Upstairs, you’ll find two additional bedrooms and a full bathroom, offering flexible space for family, guests, or a home office. Each room provides a cozy retreat while maintaining the home’s light and airy feel. Step outside and enjoy the beauty of the Eastern Shore, where wide-open spaces create a true sense of escape. The community enhances the lifestyle with a fishing and crabbing pier, as well as a small boat ramp—perfect for enjoying everything the surrounding waterways have to offer. Located just minutes from St. Michaels, marinas, waterfront dining, and local shops, this property presents a wonderful opportunity for a full-time residence, weekend getaway, or investment property. A rare combination of space, charm, and lifestyle—this is Eastern Shore living at its finest!

22539 Indian Point Rd, Bozman

Listing courtesy of Keller Williams Flagship. Contact:

Selling Office: Thyme Real Estate Co LLC.

7854 Ward Brothers Cir, Easton
$449,990
2 Beds ⋅ 2 Baths
Welcome to the Spring Lake II, a beautifully designed home that pairs an open-concept layout with timeless Loft elements. Offering 2 bedrooms, 2 baths, and a 2-car garage, this home provides both elegance and everyday functionality. Just off the foyer, a formal dining room creates the perfect setting for hosting holidays and special gatherings. The spacious kitchen is both stunning and practical, featuring a large island and walk-in pantry to support effortless entertaining and daily living. The open and airy great room impresses with a vaulted ceiling, optional beams, and a sliding door leading to the covered patio, seamlessly blending indoor and outdoor living. A cozy fireplace with mantel and hearth adds warmth and character to the space, while the screened-in patio offers another inviting area to relax. The luxurious primary suite is a true retreat, highlighted by triple windows for abundant natural light and a gorgeous primary bath with an optional freestanding tub and walk-in closet. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

7854 Ward Brothers Cir, Easton

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact:

Selling Office: Unrepresented.

505 Decatur Pl, Easton
$445,000
3 Beds ⋅ 2 Baths
Classic Cape Cod charm meets thoughtful updates at 505 Decatur Place! Situated on a spacious approximately one-third-acre lot in a quiet Easton neighborhood near the high school, this 3-bedroom, 2-bath home offers a convenient location and a versatile layout. A beautifully updated kitchen and original hardwood floors throughout the first floor bring warmth and character, while the main-level primary suite adds everyday convenience. Upstairs, two spacious bedrooms share a Jack-and-Jill bathroom. Attractive, manageable landscaping adds curb appeal, and the screened-in porch and large backyard provide plenty of room to spread out, relax, and entertain. The two-car garage offers ample extra storage, while the generous driveway and street parking in front accommodate additional vehicles. Enjoy the space of a large in-town lot just minutes from Easton’s shopping, dining, and local amenities. Priced to sell, this inviting home is ready for its next chapter!

505 Decatur Pl, Easton

Listing courtesy of Taylor Properties. Contact:

Selling Office: Meredith Fine Properties.

7453 Jeffreys Way, Easton
$445,000
2 Beds ⋅ 2 Baths
Welcome to 7453 Jeffreys Way in the desirable Easton Club East community — This is a meticulously maintained one-level home offering approximately 1,955+/- square feet of comfortable living space with vaulted ceilings, natural gas fireplace, gleaming hardwood flooring, and an inviting floor plan designed for both everyday living and entertaining. This 2-bedroom, 2-bath residence offers spacious living and dining areas filled with natural light, a bright sunroom perfect for morning coffee, reading, or quiet relaxation, and a well-designed kitchen that flows seamlessly into the main living spaces. Vaulted ceilings create an airy feel throughout much of the home, while warm hardwood flooring adds character and continuity. The generously sized primary suite features ample closet space and a private spa-like bath, while the second bedroom and additional full bath provide comfortable accommodations for family or guests. An oversized two-car garage offers excellent storage and functionality. Recent updates include a newer roof installed October 2020 and a newer 2025 hot water heater. Residents of Easton Club East enjoy community amenities including a clubhouse, pool, tennis courts, walking paths, and beautifully maintained common grounds. The home is serviced by Easton Utilities for natural gas, electric and high-speed internet with municipal water and sewer, trash and recycling services through Town of Easton. Lawn maintenance is included, further enhancing the ease and low maintenance lifestyle this community offers, all conveniently located near historic downtown Easton’s restaurants, shopping, medical facilities, and cultural attractions. Easy access to Route 50 provides convenient travel to Annapolis, the Bay Bridge, Washington D.C., and Maryland and Delaware beaches. This move-in ready home offers low-maintenance living in one of Easton’s most sought-after active adult communities.

7453 Jeffreys Way, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

504 Bainbridge Pl, Easton
$444,000
3 Beds ⋅ 3 Baths
Welcome to 504 Bainbridge Place in Easton, ideally located near Route 50, Easton High School, and the Elks Club. This sought-after location offers both convenience and community. The property is improved with a well-maintained 3-bedroom split-level home featuring numerous upgrades, including renovated bathrooms, updated AC, and mini-split systems throughout for added comfort and efficiency. Additional highlights include a detached two-bay garage with overhead storage, alley access, and an elevator making it easy to send your items upstairs. Relax year-round in the sunroom overlooking the large, fully fenced rear yard — perfect for entertaining, pets, or outdoor enjoyment. Priced at current appraisal!

504 Bainbridge Pl, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

8724 Harper Way, Easton
$443,990
4 Beds ⋅ 2 Baths
**Red Tag Sales Event through August 2, 2026! Was $448,990 Now: $443,990!** Introducing 8724 Harper Way, a new home beginning construction in the Gannon Range community of Easton, MD. The Cali is a sizeable single-story home optimizing every bit of its 1,774 square feet with four bedrooms, two full baths, a covered back patio, and a two-car garage. As you enter the home, a guest bathroom sits conveniently between two secondary bedrooms. Continuing down the hallway, you will find the garage located across from the laundry room, and a third guest bedroom tucked away privately. The living space is open with the kitchen overlooking the living area and dining room. The functional kitchen comes with a large center island, classic white cabinets, stainless steel appliances, granite countertops, and a large corner pantry. The owner's suite is located at the back of the home for privacy and offers an ample en-suite bathroom with a double vanity, custom shower, and a spacious walk-in closet. You will enjoy a fully sodded, irrigated, and landscaped lawn with this home along with white window treatments and the exclusive America’s Smart Home® package. Pictures, artist renderings, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Image representative of plan only and may vary as built. Images are of model home and include custom design features that may not be available in other homes. Furnishings and decorative items not included with home purchase.

8724 Harper Way, Easton

Listing courtesy of D.R. Horton Realty of Virginia, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

8658 Cummings Rd, Wittman
$435,000
3 Beds ⋅ 2 Baths
Enjoy the ease of one-level living in this well-maintained rancher, built in 2002 and situated on 2+/- acres in the quaint village of Wittman. Offering 1,662+/- sqft, this 3-bedroom, 2-bath home provides comfortable living with plenty of room to enjoy both inside and out. Hardwood flooring welcomes you into the foyer, which opens to a spacious living room. The kitchen features ample cabinetry, generous table space and overlooks the backyard, creating the perfect setting for everyday meals or entertaining. The spacious primary bedroom features a large walk-in closet. A convenient side entry leads to the laundry room and a separate full bath. Outside, the open yard offers endless possibilities with plenty of space for gardening, recreation or simply enjoying the outdoors. The oversized detached garage provides abundant room for vehicles, a workshop, hobbies and additional storage, while the blacktop driveway adds convenience and curb appeal. A recently installed 3-ton HVAC system provides added comfort and peace of mind. Located less than ¾ of a mile from the Wittman boat landing, you'll have easy access to Cummings Creek, the Chesapeake Bay, and surrounding tributaries for boating, fishing, crabbing, kayaking, and waterfront dining. Conveniently situated between Tilghman Island and Historic downtown St. Michaels, this property offers the perfect opportunity to enjoy the relaxed lifestyle and natural beauty of Maryland's Eastern Shore.

8658 Cummings Rd, Wittman

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

100 Division, E St, Oxford
$435,000
3 Beds ⋅ 2 Baths
Fantastic summer getaway or full-time residence just minutes from all of Oxford's amenities which include famous restaurants, marinas, tennis/pickle ball courts, the Oxford Museum, the active Community Center and wonderful nature trails. Located only one block from a public access sitting area overlooking Town Creek. The standout features include all new flooring throughout, the fabulous screened porch, the open floor plan, many windows offering lots of natural light, plenty of off street parking, the primary bedroom with en-suite bathroom and two additional bedrooms share a second full bathroom, making it a great option for hosting guests. Tour this renovated and updated home before it's too late.

100 Division, E St, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Coldwell Banker Realty.

29009 Information Ln, Easton
$435,000
3.11 Acres of land available for purchase in the Easton Technology Park. Due to the property's close proximity to Route 50, it's location creates an ideal and central hub with easy mobility to the Bay Bridge, Salisbury, and Seaford, DE. Other nearby points of interest include the Easton Airport and the new UMMS Shore Regional Health Medical Center, which is anticipating a 2028 opening. The new hospital will be 280,000 SF with potential access via rear of Easton Technology Park. - Utilities at the curb. - Natural Gas. - Park is adjacent to new 260,000 UMMS Hospital, to be delivered 2028. With potential access. - Prime Development opportunity for Medical Office, Light Industrial, and Flex Space.

29009 Information Ln, Easton

Listing courtesy of SVN/Miller Commercial Real Estate. Contact:

Selling Office: Benson & Mangold, LLC.

29736 Tallulah Ln, Easton
$431,000
4 Beds ⋅ 3 Baths
Nestled in the serene community of Matthewstown Run, this exquisite Colonial-style residence offers a harmonious blend of elegance and comfort. Built in 2003, this meticulously maintained home spans 1,920 sq ft and is set on a 0.29-acre lot that backs to lush trees, providing a tranquil backdrop for your everyday life. Step inside to discover a warm and inviting interior that boasts an open floor plan, perfect for both entertaining and everyday living. The main level features stunning hardwood floors that flow seamlessly throughout and tile in the kitchen, complemented by plush carpeting in the cozy bedrooms. The heart of the home is the spacious combination kitchen and dining area, where culinary dreams come to life. Equipped with appliances, including a built-in microwave, gas oven/range, dishwasher, and refrigerator, this kitchen is designed for both functionality and style. A charming breakfast area invites you to enjoy your morning coffee while basking in the natural light that pours in through the windows. The primary suite is a true retreat, featuring an en-suite bathroom and a generous walk-in closet, ensuring ample storage for your wardrobe. The convenience of a main-floor laundry area adds to the home's appeal, making daily chores a breeze. Outside, the property features a lovely patio, perfect for al fresco dining or simply unwinding in the fresh air. The attached garage, with space for two vehicles, offers both convenience and security, while the driveway provides additional parking for guests. Enjoy the peace of mind that comes with living in a well-established neighborhood with no HOA, where nature is just outside your door. Whether you're hosting gatherings or enjoying quiet evenings at home, this property offers the perfect setting for creating lasting memories. Experience the luxury of space, comfort, and nature in this beautiful home. It's more than just a place to live; it's a place to thrive.

29736 Tallulah Ln, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Berkshire Hathaway Homeservice Homesale Realty.

635 Elizabeth St, Easton
$429,990
3 Beds ⋅ 2 Baths
Welcome to this beautifully renovated Eastern Shore cottage, tucked away on a lovely, private lot in Easton. Offering the ease of one-level living, this inviting home blends classic cottage charm with thoughtful design and beautifully selected materials throughout. Inside, refinished hardwood floors create a warm and timeless foundation for the spacious, open floor plan. The vaulted kitchen is both beautiful and functional, featuring granite countertops, a classic subway backsplash, and Moroccan limestone flooring that adds natural texture and old-world character. The kitchen flows effortlessly into the adjoining living spaces, making the home equally comfortable for everyday living or entertaining. The primary suite is a true retreat, with a custom-designed bathroom that feels like a work of art. The space pairs Italian marble flooring with exquisite New Ravenna tile and handcrafted Moroccan Zellige tilework on the walls. The distinctive mosaic is waterjet-cut, hand-clipped, and meticulously pieced together by hand, creating a one-of-a-kind composition with remarkable depth, texture, and artistry. The beautifully varied, hand-finished Zellige tile adds an organic quality and subtle dimension to the space, complementing the luminous marble beautifully. A spacious walk-in shower completes this exceptional retreat. Two additional bedrooms are sunny and generously sized, offering comfortable accommodations for family, guests, or a home office. A well-appointed hall bathroom serves these bedrooms. A charming sitting room provides a cozy secondary living space, anchored by a classic fireplace mantle and electric fireplace. From here, step directly outside to the private, fully fenced yard—a wonderful setting for morning coffee, outdoor dining, gardening, pets, or simply enjoying the peace and privacy of your own Eastern Shore retreat. Ideally located in Easton, the home offers easy access to the town’s charming downtown, celebrated restaurants, independent shops, galleries, and the natural beauty of the Chesapeake Bay region. Enjoy the best of Eastern Shore living while coming home to your own private and beautifully appointed retreat. Thoughtfully designed, beautifully crafted, and wonderfully easy to live in—this is an Eastern Shore cottage with a character all its own.

635 Elizabeth St, Easton

Listing courtesy of Berkshire Hathaway HomeServices Homesale Realty. Contact:

Selling Office: Benson & Mangold, LLC.

28484 Woods Dr, Easton
$425,000
3 Beds ⋅ 3 Baths
Welcome to 28484 Woods Drive, nestled in the highly sought-after Easton Club community on the desirable west side of Easton, Maryland. This beautifully maintained home offers the perfect blend of elegant, low-maintenance living and exceptional community amenities, creating an ideal Eastern Shore lifestyle. Offering approximately 1,806 square feet, this freshly painted home features 3 bedrooms and 2 full bathrooms. Beautiful wood flooring extends throughout the main living areas, while brand-new carpeting in the upstairs and all bedrooms provides a fresh, comfortable feel. The open-concept floor plan is filled with natural light thanks to generous windows and offers a warm, inviting family room centered around a cozy gas fireplace. Designed for both comfort and convenience, the home also features a highly desirable first-floor primary suite. The quarterly HOA provides outstanding value by covering lawn care, snow removal, and common area maintenance, allowing for easy, carefree living. Residents enjoy access to outstanding neighborhood amenities, including an outdoor community swimming pool, tennis and pickleball courts, and nearby golf courses. Conveniently located just minutes from historic downtown Easton, the Talbot County YMCA, shopping, dining, and the scenic walking trails of Idlewild Park, this home also offers quick access to U.S. Route 50 for an easy commute to the Bay Bridge, Annapolis, and destinations throughout Maryland's Eastern Shore. Move-in ready and ideally located, 28484 Woods Drive is an exceptional opportunity to enjoy comfortable living in one of Easton's most desirable communities. *** Owner will repair or replace the shattered window in the primary bedroom.

28484 Woods Dr, Easton

Listing courtesy of Laurel Murphy Real Estate, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

8953 Treesdale Dr, Easton
$425,000
3 Beds ⋅ 2 Baths
Rare opportunity: Updated ranch-style home offering 3 bedrooms and 2 full baths, including a private primary suite, set on a semi-private property on Maryland’s Eastern Shore. The sale includes an additional separate 1.55-acre lot (Tax ID: 2101039261), providing added space and privacy for a total of 2.41 acres. The upgraded kitchen features updated countertops, cabinetry, appliances, flooring, and modern lighting, while updated flooring extends throughout most of the main level. A wood-burning fireplace anchors the additional living space. The primary suite and second bedroom both include walk-in closets, and both full bathrooms have been tastefully updated. Enjoy year-round comfort and efficiency with a recently replaced HVAC system featuring energy-saving geothermal technology. A large sunroom and exterior deck overlook the wooded backyard, offering the perfect setting to relax and enjoy the natural surroundings. The property also features a 12x24 shed for additional storage, a LeafGuard gutter system with transferable warranty, and a separate forced-air propane furnace in the garage for added comfort during colder months. A 2-car attached garage completes the home’s features. Experience rural living with beautiful mature trees and privacy, all just minutes from Easton’s shopping, dining, and local amenities.

8953 Treesdale Dr, Easton

Listing courtesy of Keller Williams Flagship. Contact:

Selling Office: Samson Properties.

111 Gloria, Saint Michaels
$425,000
2 Beds ⋅ 2 Baths
Essentially a NEW HOME! Extensively, tastefully and professionally renovated 1965 rancher located on a quiet residential street, just 2 blocks from downtown St. Michaels. Nearly everything is brand new, including roof shingles, siding, windows, HVAC system and new deck. New off-street parking area, sized for 2 vehicles. Inside, everything looks (and is) new, including attractive luxury vinyl floors throughout, spacious kitchen w/all-new stainless Whirlpool appliances (range; refrigerator w/ice; dishwasher; built-in microwave oven), separate laundry room w/stacked washer/dryer, powder room, full bath, living room, dining/family room and two bedrooms with good closet space...all on one level! The house is attractive, comfortable and bright inside. Sliding glass doors off the family room lead to a new deck, overlooking the private back yard, where you will see a substantial renovated shed, approximately 20' x 15'...perfect for use as a "He-Shed/She-Shed," workshop and/or garden shed and storage area. "Move-in Ready!"

111 Gloria, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Chesapeake Real Estate Associates, LLC.

7184 Oxford Rd, Easton
$425,000
3 Beds ⋅ 3 Baths
Back and better than ever — structural repairs made and repairs to septic system. If privacy just minutes from everything is what you want—LOOK NO FURTHER • 3 acres of privacy while staying close to Easton's shopping, dining, schools, and everyday essentials • Fully renovated throughout—everything is done and move-in ready • Main-level primary suite with a sitting room • Large fenced in area perfect for dogs & kids • Outbuilding with electric—ideal for a studio, office, or workshop • Easy Eastern Shore living: minimal traffic, quick errands, quality healthcare, excellent dining, museums, trails, parks, and easy to get to St. Michaels and Annapolis • Move in and enjoy the summer in your new home on Maryland's Eastern Shore!

7184 Oxford Rd, Easton

Listing courtesy of Engel & Volkers Annapolis. Contact:

Selling Office: Chesapeake Real Estate Associates, LLC.

29868 Nicholas Way, Easton
$420,000
2 Beds ⋅ 2 Baths
Professional interior photos to come by 6/3. Welcome to 29868 Nicholas Way in Chesapeake at Easton Club East—an inviting corner-lot home offering the ease of one-level living in one of Easton’s most desirable active adult communities. Thoughtfully designed with comfort and convenience in mind, this beautifully maintained home offers nearly 1,900 square feet of bright and functional living space. The floor plan is ideal for everyday living and entertaining, with two main-level bedrooms including a spacious primary suite featuring a walk-in closet and an ensuite bath designed for accessibility, complete with a roll-in shower and lift system. At the heart of the home is the open kitchen with a center island, Corian countertops, and easy-care luxury vinyl tile flooring, flowing seamlessly into the living room where a gas fireplace creates a warm and welcoming focal point. Just beyond, the sunroom opens to the rear patio and fills the home with natural light, creating the perfect place to relax with a book or enjoy guests year-round. A separate front office or sitting room with custom built-ins adds flexibility and charm. Outside, the setting is just as special. The .25-acre corner lot is framed by a classic white picket fence and backs to peaceful woods, offering privacy and a beautiful natural backdrop. Enjoy outdoor living on the spacious rear paver patio or start your mornings on the full-length front porch. Additional highlights include an oversized two-car garage with attic storage, custom closet systems, central vacuum, alarm system, irrigation, and a Gutter Helmet system for low-maintenance living. Residents of Chesapeake at Easton Club East enjoy an exceptional lifestyle with beautifully maintained grounds and resort-style amenities including a clubhouse, fitness center, ballroom, game and craft rooms, private junior Olympic pool, tennis courts, putting green, horseshoe court, scenic walking trails, and six charming pocket parks with gazebos and ponds. Ideally located just minutes from downtown Easton and within easy reach of Annapolis, BWI, and Washington, DC, this is Eastern Shore living at its best—comfortable, connected, and wonderfully easy.

29868 Nicholas Way, Easton

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

Selling Office: RE/MAX Allegiance.

8388 Colony Cir, Easton
$420,000
4 Beds ⋅ 3 Baths
Welcome to 8388 Colony Circle, a charming Juniper model offering 4 bedrooms, 2.5 bathrooms, and timeless traditional style just minutes from downtown Easton. This well maintained two-story home features a new roof, hardwood floors throughout the main level, a cozy fireplace, and custom built-ins that add warmth and character to the living space. The eat-in kitchen flows seamlessly into a spacious formal dining room, perfect for entertaining, while upstairs you’ll find generously sized bedrooms, including a primary suite with an expansive walk-in closet. Nestled in a quiet, established neighborhood, this property combines comfort, convenience, and space. Easy to show and available for immediate occupancy, this home is ready to welcome its next owner!

8388 Colony Cir, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: RE/MAX Executive.

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