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$360,000
3 Beds ⋅ 2 Baths
Welcome to 402 Cherry Street, a beautifully, renovated three or four bedroom, two-full bath, light-filled home located in the charming historic district of Easton. The residence combines modern updates with prime location and offers a low-maintenance lifestyle in the heart of this captivating town. Renovated in 2023 and thoughtfully designed to maximize space and functionality. The attention to detail is evident throughout, with stylish finishes and fixtures that perfectly complement the cozy interior. The floor plan allows for comfortable, everyday living. One of the standout features of this property is the small, private courtyard. This intimate outdoor space provides a private sanctuary where you can relax, unwind, and enjoy the outdoors. With minimal yard maintenance required, you'll have more time to savor the wonderful amenities Easton has to offer. Walking distance to an array of cultural attractions, galleries, boutique shops, and dining establishments. Schedule a private showing today. Off street parking located on N Higgins Street.

402 Cherry St, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$1,685,000
5 Beds ⋅ 5 Baths
UNIQUE PROPERTY RIGHT OUTSIDE OF HISTORIC ST MICHAELS TOWN LIMITS ACROSS THE LINK AT PERRY CABIN. THIS FABULOUS HOME OFFERS SPACE FOR GATHERINGS WITH FAMILY OR FRIENDS BUT ALSO FEELS COZY FOR EMPTY NESTERS THAT LOVE TO ENTERTAIN. THERE ARE NO RESTRICTIONS THAT PROHIBIT VACATION RENTAL, THERE SHOULD BE SPACE FOR AN INGROUND POOL . ORIGINALLY BUILD IN 1973 THE CURRENT OWNER GUTTED THE HOME, ALL SYSTEMS, ELECTRICAL, WINDOWS, FLOORS ETC ARE NEW- JUST MOVE IN AND ENJOY. FROM NATURAL OAK FLOORS TO MARBLE BATHROOMS, WHITE SPACIOUS KITCHEN WITH GLEAMING GRANITE AND SOAP STONE COUNTERTOPS. EXTENSIVE OUTDOOR LIGHTENING , SPEAKERS, LIGHTENING UNDER THE EVES TURN THIS INTO A MAGICAL PLACE IN THE EVENING. GATHER BY THE HUGE FIREPIT AND ENJOY OUTDOOR LIVING , COOKING AND DINING ON THE VARIOUS PATIOS OR WRAP AROUND DECK. MAINTENANCE EASY MATERIALS HAVE BEEN USED FOR THE DECKING, SIDING AND ROOFING, ATTENTION WAS PAID TO GUTTER SYSTEMS AND GRADING. THE DRIVEWAY IS FRAMED BY BELGIAN COBBLESTONE, STONE COLUMNS GREET YOU WHEN YOU ENTER THE PROPERTY. THIS IS A RARE OPPORTUNITY FOR A TURN KEY PROPERTY IN ST MICHAELS WITHOUT THE TOWN PROPERTY TAXES AND RESTRICTIONS.

9180 Saint Michaels, Saint Michaels

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 4107450283
$515,000
2 Beds ⋅ 2 Baths
Just 12 miles from St Michaels, this house is in a quiet community of 60+ homes at the end of a lovely peninsula. A public landing is at the end of Bozman Neavitt Road, and a community center and park are in the heart of the village. This property has been renovated and updated from the studs out. Features now include 2-3 Bedrooms 2 Full baths Living room with built-ins Light-filled kitchen with cathedral ceiling Large landscaped lot with patio A Short-term Rental application is underway. Ask owner for details. Some furniture conveys

6394 Bozman Neavitt Rd, Neavitt

Listing courtesy of TTR Sotheby's International Realty. Contact:

$450,000
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:

$2,500,000
Discover one of Talbot County’s rare farms that combines productive farmland, waterfront, and exceptional recreational opportunities. This 105.72-acre agricultural property features approximately 80± acres of tillable ground and is well suited for continued farming, income production, or long-term land investment. The open farmland is framed by wooded perimeter lines with a mixture of mature hardwoods and softwoods, including pine and oak, providing privacy, scenic beauty, and excellent wildlife habitat. The property is zoned agricultural, offering flexibility for farming, recreation, or investment use. The tillable acreage carries an overall NCCPI rating of approximately 57.3, indicating solid, productive ground suitable for row crops, small grains, and conservation programs. The farm boasts over 2,500 feet of water frontage on Miles Creek, offering excellent duck and goose hunting opportunities. The property is located on a known migratory flyway for ducks and geese along the Chesapeake Bay, making it a proven waterfowl destination. A network of trails through the wooded areas leads to a cleared waterfront area on Miles Creek featuring a dock and picnic table, ideal for family activities, swimming, and fishing. A small point along the creek includes a strategically placed booby blind, positioned for effective duck and goose hunting. Additional amenities include multiple duck blinds on Miles Creek and a goose pit. The historic two-story farmhouse, dating to the early 1900s, offers five bedrooms and one full bathroom and features a new roof and siding. Beginning with the main floor, the home offers a large living room, dining room, kitchen, and the first of five bedrooms. The second floor includes four large bedrooms and a full bath. The residence is accessed by a private driveway off Saulsbury Road, providing convenient access while maintaining a high level of privacy. A small shed next to the home provides additional storage. This property is income-producing, with revenue potential from farming operations, CRP enrollment, and hunting leases, making it a versatile investment opportunity, productive farm, or private recreational retreat with waterfront access. Property is being offered in cooperation with Casey Kennedy and Whitetail Properties.

4108 Saulsbury Rd, Trappe

Listing courtesy of VYBE Realty. Contact: 4102204648
$2,500,000
5 Beds ⋅ 1 Baths
Discover one of Talbot County’s rare farms that combines productive farmland, waterfront, and exceptional recreational opportunities. This 105.72-acre agricultural property features approximately 80± acres of tillable ground and is well suited for continued farming, income production, or long-term land investment. The open farmland is framed by wooded perimeter lines with a mixture of mature hardwoods and softwoods, including pine and oak, providing privacy, scenic beauty, and excellent wildlife habitat. The property is zoned agricultural, offering flexibility for farming, recreation, or investment use. Property is being offered in cooperation with Casey Kennedy and Whitetail Properties. The tillable acreage carries an overall NCCPI rating of approximately 57.3, indicating solid, productive ground suitable for row crops, small grains, and conservation programs. The farm boasts over 2,500 feet of water frontage on Miles Creek, offering excellent duck and goose hunting opportunities. The property is located on a known migratory flyway for ducks and geese along the Chesapeake Bay, making it a proven waterfowl destination. A network of trails through the wooded areas leads to a cleared waterfront area on Miles Creek featuring a dock and picnic table, ideal for family activities, swimming, and fishing. A small point along the creek includes a strategically placed booby blind, positioned for effective duck and goose hunting. Additional amenities include multiple duck blinds on Miles Creek and a goose pit. The historic two-story farmhouse, dating to the early 1900s, offers five bedrooms and one full bathroom and features a new roof and siding. Beginning with the main floor, the home offers a large living room, dining room, kitchen, and the first of five bedrooms. The second floor includes four large bedrooms and a full bath. The residence is accessed by a private driveway off Saulsbury Road, providing convenient access while maintaining a high level of privacy. A small shed next to the home provides additional storage. This property is income-producing, with revenue potential from farming operations, CRP enrollment, and hunting leases, making it a versatile investment opportunity, productive farm, or private recreational retreat with waterfront access.

4108 Saulsbury Rd, Trappe

Listing courtesy of VYBE Realty. Contact: 4102204648
$455,000
3 Beds ⋅ 3 Baths
Set within the sought-after Martingham community of Quail Hollow, backing to the top rated golf course The Links at Perry Cabin, this fully updated 3-bedroom, 3-bath townhome offers stylish, low-maintenance living just minutes from downtown St. Michaels. Extensive renovations completed between 2022 and 2024 make this home truly turnkey. The main level welcomes you with beautiful wood floors, a bright and open living area with gas fireplace, custom built-ins, and seamless access to a private rear patio overlooking peaceful common space. The stunning kitchen has been completely transformed with quartz countertops, soft-close cabinetry, and newer stainless steel appliances. A main-level bedroom with its own ensuite bath provides flexible living options for guests or primary use. Upstairs, the spacious owner’s suite features a private balcony, a spa-like bath, and generous closet space, along with a second guest suite offering its own private bath. Additional improvements include fresh interior and exterior paint, a newer HVAC system (within the last five years), updated carpeting, refinished hardwood floors, and recently installed 6” gutters. The property includes a one-car garage with attic storage,plus paved parking. Backing to open common area for added privacy and tranquility, and located near The Links at Perry Cabin with no town taxes, this home delivers comfort, convenience, and exceptional value.

9518 Quail Hollow Unit #702, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415
$449,000
3 Beds ⋅ 2 Baths
No neighbors, private and set back off the road. Beautifully Updated Split-Level Retreat on Nearly an Acre Along Route 50! Set back on a private, wooded lot just under an acre, this beautifully remodeled 3-bedroom, 2.5-bath split-level home offers the perfect blend of comfort, style, and outdoor enjoyment. A long circular driveway welcomes you home, setting the tone for the peaceful setting that surrounds this 2,676 sq. ft. property. Inside, the home has been thoughtfully updated since purchase, including new replacement windows, mini-splits, new paint, new LVP flooring, a fully remodeled bathroom, and a vapor barrier with insulated crawl space—providing both modern comfort and long-term peace of mind. The main level features bright, open living spaces with sliding doors from both the living and dining rooms leading to the screened-in porch. From here, you can relax while overlooking the serene pond and the inviting in-ground pool—an ideal setup for entertaining or unwinding after a long day. The finished lower level expands your living possibilities with a cozy den complete with a bar area, a utility/laundry room, and two bonus rooms that can easily be converted into a large fourth bedroom or additional sleeping quarters. Sliding doors from the den offer direct access to the pool area, creating a seamless indoor-outdoor flow. Additional highlights include a wood-burning stove, ample storage, and the flexibility to add 1–2 more bedrooms if desired. With professional photos coming soon, this move-in-ready home is sure to draw attention quickly. A rare combination of privacy, upgrades, and lifestyle amenities—this one truly won’t last. Pool will be open soon.

7364 Ocean Gtwy, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415
$575,000
4 Beds ⋅ 3 Baths
Spacious Colonial in Charlestown Village - Welcome home to this beautifully cared-for Colonial offering 4 bedrooms, 2.5 baths, and over 2,288 sq. ft. of living space (actual square footage exceeds the tax record). The main level features hardwood flooring and a comfortable flow designed for everyday living and entertaining. At the back of the home, the kitchen with stainless steel appliances and granite countertops opens to a breakfast area and a cozy family room with a gas fireplace, all with easy access to the deck and in-ground pool. The main level also includes a formal dining room and a flexible living room/office. Upstairs, a spacious bonus room over the garage offers the perfect hangout space—or could easily serve as the 4th bedroom. Outside, enjoy a fenced backyard, large storage shed, paved driveway, and an attached 2-car garage. Charlestown Village is a sought-after neighborhood featuring lighted streets, sidewalks, and in-town convenience. This home combines space, comfort, and an ideal location. The owners are currently building a new home.

316 Spring Dr, Easton

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$779,000
3 Beds ⋅ 2 Baths
A rare opportunity to pair a half-acre+ wooded in-town parcel with a thoughtfully designed single-level home concept in the heart of St. Michaels. This Concept A plan illustrates a 3-bedroom, 2-bath residence totaling approximately 1,710 square feet, featuring one-level living and an attached one-car garage. Designed to maximize functionality and flow, the concept offers flexible living spaces that can be tailored to the buyer’s preferences while preserving privacy and connection to the natural setting. Restaurants, shops, seasonal events, waterfront parks, and the character of the historic district are all close at hand, yet the setting feels quiet and tucked away. Approximately three times the size of a typical in-town lot, the parcel allows generous room for outdoor living and thoughtful home placement, with driveway access possible from Miles Avenue, Canton Street, or both, depending on final design. Infrastructure upgrades are already complete, including paved roads, a State-approved gravel extension, town water, county sewer, electric service, and fiber-optic internet—allowing for a smoother path from planning to construction. With the appropriate Town approvals, the parcel also offers future subdivision potential. Adjacent to the scenic Rails-to-Trails corridor and near San Domingo Creek, the Miles River, and multiple neighborhood parks, the location provides access to nature and open space without giving up the benefits of being in town. Architectural concept drawings illustrating one potential approach to the site will convey to the new owner, with the option to continue working with the original architect if desired. A unique chance to create something truly exceptional in one of the Eastern Shore’s most sought-after communities: space, privacy, and the freedom to design a home that reflects your vision. By Vehicle: A portion of Canton St is a one-way and Miles Ave is not a completely through Street from Railroad Ave. It is recommended to head north on Talbot St., turn left on Railroad Ave., then left on Glory Ave (also known as Gloria), and right on Canton St. Proceed a short way to the corner of the lot at Miles Ave. & Canton St.

108 Miles Ave, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$295,000
A rare opportunity in the heart of St. Michaels: this half-acre+ wooded parcel offers the privacy of a tucked-away retreat with the everyday convenience of an in-town location. Restaurants, shops, seasonal events, waterfront parks, and the character of the historic district are all close at hand, yet the setting feels quiet and natural. Approximately three times the size of a typical in-town lot, the property provides remarkable flexibility for home placement, architectural style, and outdoor living spaces. The generous buildable envelope allows for a variety of layouts, and driveway access can be configured from Miles Avenue, Canton Street, or both, depending on the design. Infrastructure upgrades are already complete, including paved roads, a State-approved gravel extension, town water, county sewer, electric service, and fiber-optic internet—allowing for a smoother path from planning to construction. With the appropriate Town approvals, the parcel also offers future subdivision potential. Adjacent to the scenic Rails-to-Trails corridor and near San Domingo Creek, the Miles River, and multiple neighborhood parks, the location provides access to nature and open space without giving up the benefits of being in town. Architectural concept drawings illustrating one potential approach to the site will convey to the new owner, with the option to continue working with the original architect if desired. A unique chance to create something truly exceptional in one of the Eastern Shore’s most sought-after communities: space, privacy, and the freedom to design a home that reflects your vision. By Vehicle: A portion of Canton St is a one-way and Miles Ave is not a completely through Street from Railroad Ave. It is recommended to head north on Talbot St., turn left on Railroad Ave., then left on Glory Ave (also known as Gloria), and right on Canton St. Proceed a short way to the corner of the lot at Miles Ave. & Canton St.

108 Miles Ave, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$499,990
4 Beds ⋅ 3 Baths
Enjoy the serenity of country living just minutes from both downtown Easton and Cambridge! This spacious four bedroom, two and a half bath home offers over 3,400 square feet of living space and sits on nearly an acre (.96+/-) with covered front porch and nice rear deck with views of open fields/farmland. This solid house offers a comfortable layout on both levels and it's perfect for both everyday living and entertaining. The main level features a large two story foyer with beautiful staircase, large family room, open kitchen with breakfast nook and beautiful bay window, separate dining room, and sunroom with vaulted ceiling, skylights, wood burning fireplace and beautiful open views of farmland. Upstairs, the primary suite is like a private retreat with it’s own bathroom, walk in closet and balcony. Three additional bedrooms and bath complete the second floor. Attached two car garage with private circular drive surrounded by mature trees for privacy. The home features a new roof (2025), a new well, new septic system (2025) and new HVAC (2022). Within a mile of Ferry Point Marina, Waterfront State Park and Choptank Fishing Pier. Close to all of downtown Trappe/Easton/Cambridge shopping, restaurants, churches and medical facilities.

2669 Ocean Gtwy, Trappe

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415
$729,500
3 Beds ⋅ 3 Baths
Nestled in the prestigious Cooke's Hope community, this exquisite end-of-row townhouse embodies the perfect blend of elegance and comfort. Built in 2004, this Colonial-style residence boasts a timeless brick façade that invites you into a world of refined living. Spanning 2,819 square feet, this home features three spacious bedrooms and two and a half luxurious bathrooms, designed to cater to your every need. Step inside to discover an open floor plan that seamlessly connects the living and dining areas, adorned with crown moldings and warm bamboo and hardwood flooring. The family room, conveniently located off the kitchen, is perfect for cozy gatherings, enhanced by a stunning gas fireplace with glass doors that create an inviting ambiance. Natural light floods the space through double-pane insulated windows, offering serene views of the lush garden and surrounding trees. The gourmet kitchen is a chef's dream, featuring energy-efficient appliances, including a built-in microwave, self-cleaning oven, and a sleek range hood. The galley-style layout is complemented by a pantry and ample counter space, making meal preparation a delight. Enjoy casual dining in the charming breakfast area, where you can savor your morning coffee while overlooking the tranquil rear yard. Retreat to the master suite, complete with a walk-in closet and a spa-like en-suite bathroom featuring a soaking tub and a walk-in shower. Each additional bedroom offers generous space and comfort, ensuring a restful haven for all. Outside, the property is equally impressive. The 0.14-acre lot adjoins open space and backs to a serene common area, providing a sense of privacy and tranquility. Enjoy leisurely evenings on your patio, surrounded by beautifully landscaped gardens and the gentle rustle of trees. The cul-de-sac location ensures minimal traffic, enhancing the peaceful atmosphere. Additional features include a two-car attached garage with extra storage, a main floor laundry area, and a comprehensive security system for peace of mind. The community offers lawn maintenance, allowing you to spend more time enjoying your luxurious lifestyle. This home is not just a residence; it's a sanctuary that offers an exclusive lifestyle, where every detail has been thoughtfully curated for comfort and elegance. Experience the perfect blend of luxury and warmth in this remarkable property.

28959 Jasper Ln, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$659,000
3 Beds ⋅ 2 Baths
The one-of-a-kind Ryan model is set to be the largest one-story home constructed on Sandy Lane, brought to life by Developer Sandy Lane, LLC and renowned local builders Stansbury and Sons. Like all ten homes in this thoughtfully designed new downtown Easton community, the Ryan will be a custom, stick-built residence backed by a one-year builder’s warranty and outfitted with brand-new appliances and systems—allowing homeowners to enjoy their new space without the constant burden of "old house" maintenance. The Ryan's convenient single-level layout includes three bedrooms, two full baths, and a spacious living room with vaulted ceilings that flows seamlessly into the dining area and a beautifully appointed kitchen. A cook's dream, the kitchen features custom cabinetry, including a large pantry cabinet, solid surface countertops, and stainless-steel appliances. The luxurious primary suite offers a private bath with a tiled shower, double sink vanity and a generous walk-in closet. The two additional bedrooms on the opposite side of the floorplan share a stylish hall bath with tub/shower. There is also a dedicated laundry area—strategically placed between the kitchen, primary suite and garage entrance—which completes the interior. Outside, the home boasts a one-car attached garage with an electric car charger, a concrete driveway with parking for two, custom front foundation landscaping, a fully sodded yard, and a rear patio. Sandy Lane homes are built with premium features such as encapsulated, climate-controlled crawl spaces suitable for storage, superior framing and finish work, certified IECC Energy Efficient insulation (R-49 ceiling, R-21 walls), luxury vinyl flooring throughout, ample closet space, and multiple contemporary ceiling fans and fixtures. The Ryan’s flexible design makes it ideal for retirees, remote workers, singles and families alike. All infrastructure costs—including surveys, permits, site work, utilities, and street improvements—have been prepaid by the developer, eliminating typical new construction extended yearly front foot fees for buyers. Located off N Washington Street in Easton, Sandy Lane offers easy access to downtown amenities such as Easton Utilities (electric, water, sewer, cable, and high-speed internet), weekly trash and recycling pickup, and a wealth of recreational options including parks, sports fields, trails, playgrounds, tennis and pickleball courts, a community pool, and a dog park. Easton and Talbot County provide abundant waterfront access, fire and police services, medical facilities, cultural attractions such as the Avalon Theater, The Academy Art Museum, and Maritime Museum, premium shopping, and some of the best dining on the East Coast. The community is subject to Covenants and Restrictions but carries no HOA or associated fees. Developer: Sandy Lane, LLC (MHBR 9512). Builder: Stansbury and Sons Home Improvement Inc. (MHBR 8351). Builder Contract required.

13 Sandy Ln, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415
$745,000
4 Beds ⋅ 4 Baths
Back on market due to BUYER not being able to sell their house! Clean inspections so READY for YOU! This beautifully sited end-unit townhouse has serene field views, and offers 2,433 sq. ft. of elegant living with 4 bedrooms, 3 full baths, and 1 half bath. Designed with an open concept, the living room, dining room, and kitchen flow seamlessly together, creating a warm and inviting space for entertaining or everyday living. Soaring two-story ceilings, skylights, and expansive windows flood the home with natural light, while a gas-burning fireplace is the focal point of this inviting space. The main-level primary suite serves as a private retreat with an ensuite bath, complemented by two walk-in closets. A cozy den and convenient powder room complete the main level. An upper-level loft overlook adds architectural charm and provides additional space for relaxation. Upstairs, one guest bedroom enjoys its own ensuite bath, and two additional bedrooms share a connecting full bath. Outdoors, a beautifully landscaped backyard framed by mature trees provides a tranquil setting, while the attached 2-car garage offers convenience. Cooke’s Hope residents enjoy an unmatched lifestyle with ponds, tennis courts, walking trails, a dog park, fitness center, picnic pavilion, and a community dock—making this one of Easton’s most desirable communities.

28933 Jasper Ln, Easton

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344
$185,000
Build Your Dream Home in Desirable High Banks Discover the perfect opportunity to create your Eastern Shore retreat on this 2.24 +/- acre homesite in the sought-after High Banks community. Nestled among mature trees and open ground, this elevated property offers water views and the peace and privacy of a well-established neighborhood. The lot is perc approved for 3 bedrooms providing a smooth path toward building your custom home. High Banks is known for its spacious lots, serene setting, and close proximity to Easton, Oxford, and St. Michaels—where boutique shopping, dining, and marinas await. Conveniently located minutes away from 2 public boat ramps. Whether you envision a weekend getaway or a full-time residence, this property combines natural beauty, community charm, and build-ready convenience.

LOT #6 High Banks Dr, Easton

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$475,000
4 Beds ⋅ 3 Baths
Private backyard in Vibrant Community. Get lost in this backyard oasis close to downtown Easton in the very exciting neighborhood of Mulberry Station. Minutes from downtown Easton, you will get lost in all the special nooks and crannies hiding in your hidden paradise. Lose yourself in a book under the Crepe Myrtles, Zen out next to the manmade Koi ponds with water features. Who needs a sound machine with the peaceful sounds of leaves rustling and babbling brooks babbling? A huge inground pool with a designated firepit area can make any evening special. This thoughtfully designed outdoor space needs to be seen to really be appreciated. Inside, you will find ample room to spread out. The lovely kitchen/family room combo features a gas fireplace to cozy up to. Indoor/Outdoor dining with sliders that open up from your kitchen onto your beautiful large deck with electric awning. Upstairs, Double doors open to your very large primary suite with walk-in closet and en-suite. Three other large bedrooms and bathroom round out the upstairs.

8862 Roundhouse Cir, Easton

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

$3,700,000
5 Beds ⋅ 7 Baths
GENEROUS PRICE REDUCTION!!!! This remarkable property has it all. Private 15 plus acres. Beautiful views overlooking Dunn's Cove sunrises. A shore sportsman's dream. Partially wooded, fields of crops, hunting blind and a pier for your fishing vessel. This was a large compound with the Main house, in-law wing and a separate 2 BR guest house w/fireplace and large screened porch. Waterside in-ground pool and children's play area. Large garage/barn to store all the water toys and pool equipment. It's currently being used as a Vacation Rental. Showings will be staggered between use.

21721 Heavenly Haven Rd, Sherwood

Listing courtesy of Chesapeake Bay Real Estate Plus, LLC. Contact:

$6,800,000
5 Beds ⋅ 6 Baths
Welcome to this extraordinary waterfront estate, gracefully sited on 6.92 lush, landscaped acres with sweeping views of Leadenham Creek. Designed by architect Alan Meyers, constructed by Ilex Construction, and masterfully styled by interior designer Skip Sroka, this 10,000+/-sq. ft. residence is a showcase of timeless craftsmanship and elevated design. The custom brick exterior is crowned by a new cedar shake roof with copper caps and bands, creating a refined profile that blends seamlessly into the natural surroundings. Double mahogany doors with full-view, artistically designed leaded glass open to a luminous foyer with immediate, breathtaking views of the water. Inside, riff-sawn red oak floors flow through expansive formal and informal living areas. Vaulted ceilings add architectural drama, while curated lighting provides warmth and sophistication throughout. The main level features formal living and dining rooms, a stunning gourmet kitchen, and multiple spaces designed for both relaxation and entertaining. The kitchen is a chef’s dream—equipped with top-tier appliances, a large center island, sitting area with fireplace, and an eat-in dining space. Just off the kitchen, a beautifully crafted screened porch with an octagonal ceiling offers a peaceful, year-round retreat. A walk-in pantry and custom-designed bar enhance both function and hospitality. Also on the main level is a striking private office wrapped in Anigre wood paneling, featuring custom built-ins and a circular backlit ceiling. A separate guest wing includes a spacious family/recreation room with spectacular river views and two guest suites with ensuite baths. The primary suite enjoys its own private wing, with serene water views, a cozy sitting area and fireplace, dual walk-in closets, and an elegant dressing hall. The luxurious, spa-inspired bath includes a soaking tub and glass-enclosed shower, creating a true sanctuary of comfort and privacy. Upstairs, dual wings on opposite sides of the home offer two additional guest suites with ensuite baths, a bonus/music room, and a dedicated fitness room. Five fireplaces handcrafted by Collecio Brothers Stone Masons bring warmth and timeless character throughout the home. Modern systems include geothermal heating and cooling, a new Honeywell HVAC control system, Vantage lighting automation, a fully encapsulated crawlspace, and a Generac generator. In addition to the oversized 3+ car attached garage, a separate detached two-bay garage offers equipment storage, a workshop, and a half bath. Outdoors, the estate is designed for both grand entertaining and quiet waterfront living. Features include an extended waterside patio, beautiful pool house with a fully equipped outdoor kitchen, two dressing rooms, an outdoor shower, and an in-ground pool with heated spa. Over 1,000 feet of riprapped shoreline and a 210-foot private dock with two slips, a floating dock, and 7-foot MLW offer direct access to the Chesapeake Bay. This remarkable estate was built for luxurious living, effortless entertaining, and a deep connection to the natural beauty of Maryland’s Eastern Shore. *Current taxes are based on homestead credit.

7090 Cooper Point Rd, Bozman

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344
$995,000
Rare find, prime Bailey's Neck/Easton location. This beautiful 3+ acre waterfront lot is on the Tred Avon River in the highly sought after Oxford Corridor. 470+/- feet of water frontage, providing expansive views of the Tred Avon River. Gorgeous views. Great location close to downtown Easton and Oxford. The property is approved for a 6-bedroom perc and now features a new path directly to the water. Survey available. Property has some property markers. It appears that part of the neighbors driveway is on the lot.

Enniskillen Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415
$1,250,000
Final section of Lakelands subdivision! Previously approved for up to 48 lots, road cut thru, some water & sewer installed. PUD approved by Town in 2010. See agent for plats, engineering and current status. Unique opportunity! Wetlands needs to be updated with possible additional land becoming available. Road needs completion. Some Capital fees already paid. Water lines partially installed along with sewer lines. Water lines needs upgrading for sprinklers.

Ocean Gtwy, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$1,250,000
Final section of Lakelands subdivision! Previously approved for up to 48 lots, road cut thru, some water & sewer installed. PUD approved by Town in 2010. See agent for plats, engineering and current status. Unique opportunity! Wetlands needs to be updated with possible additional land becoming available. Road needs completion. Some Capital fees already paid. Water lines partially installed along with sewer lines. Water lines needs upgrading for sprinklers.

Ocean Gtwy, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$8,000,000
Don’t miss out on this rare opportunity to transform this 56+/ -acre parcel into a premier development project. This expansive property offers a blend of zoning options and fantastic exposure on Route 50, making it an ideal investment for developers. The property is well-suited for high-visibility projects including home improvement stores, pad sites, restaurants, and so much more. All utilities are at the site. Located in the prime area of Easton with easy access to major roads and amenities. Owner will consider all reasonable offers. Owner will develop for a credit tenant. This offering includes Tax Map 100, Parcel 0420 Chapel Road, Easton. Located in Easton’s Opportunity Zone! Contact us today to start turning your vision into reality! Available for Sale or Lease - call for additional information.

Ocean Gateway, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415
$8,000,000
Don’t miss out on this rare opportunity to transform this 56+/ -acre parcel into a premier development project. This expansive property offers a blend of zoning options and fantastic exposure on Route 50, making it an ideal investment for developers. The property is well-suited for high-visibility projects including home improvement stores, pad sites, restaurants, and so much more. All utilities are at the site. Located in the prime area of Easton with easy access to major roads and amenities. Owner will consider all reasonable offers. Owner will develop for a credit tenant. This offering includes Tax Map 100, Parcel 0420 Chapel Road, Easton. Located in Easton’s Opportunity Zone! Contact us today to start turning your vision into reality! Available for Sale or Lease - call for additional information.

Ocean Gateway, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415