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$719,500
3 Beds ⋅ 2 Baths
Wake up to peaceful views of Peachblossom Creek and enjoy the best of Eastern Shore living from this well-maintained 3-bedroom home in the highly sought-after Oxford Road corridor. Included is access to a private waterfront lot, providing the perfect spot to launch a kayak, fish, watch wildlife, or simply take in the beauty of the water. Designed for easy one-level living, the home offers a bright and welcoming floor plan with an open kitchen featuring a marble island, spacious walk-in pantry, and adjoining living room with a gas fireplace. A heated semi-enclosed porch creates an inviting space to enjoy creek views and outdoor living throughout the seasons. The primary suite features a large walk-in closet with custom built-ins and a well-appointed bath with a no-threshold tile shower and double-sink vanity. Additional amenities include a dedicated laundry room, partially floored attic storage, updated metal roof sections installed in 2025, and a fenced rear yard with storage shed. Just minutes from downtown Easton, shopping, the YMCA, parks, and miles of bike trails, this property offers a rare opportunity to enjoy a relaxed waterfront lifestyle without the maintenance and expense of a traditional waterfront home. Excluded : One peony plants and 2 lilies.

28567 Holden Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415
$2,149,000
3 Beds ⋅ 3 Baths
NEW PRICE DO NOT MISS THIS ONE Nestled in the highly desirable Drum Point neighborhood of St. Michaels, this exceptional waterfront property offers the perfect blend of privacy, comfort, and Eastern Shore charm. Just minutes from the vibrant heart of town, you'll enjoy easy access to renowned restaurants, boutique shopping, cozy cafés, the Classic Motor Museum, and the Chesapeake Bay Maritime Museum. A former successful vacation rental, this beautifully maintained three-bedroom brick home is designed for effortless living and year-round enjoyment. The open floor plan features rich wood flooring, a striking double-sided fireplace, a renovated kitchen, updated bathrooms, and energy-efficient geothermal HVAC. Water views surround you at every turn. Relax in the shade of mature trees by the shoreline, sway in a hammock with refreshing bay breezes, or spend the day enjoying the property's outstanding outdoor amenities. Entertain guests on the spacious deck complete with an outdoor kitchen and hot tub, gather on the charming stone-walled patio, rinse off in the outdoor shower, and cool off with a swim in the pool. Boaters will appreciate the private dock offering approximately 3 feet MLW, a boat lift, and a boat launch for easy access to the water. A detached two-room studio with a covered porch provides additional flexible space for guests, hobbies, or a private retreat while enjoying spectacular water views. Additional highlights include an encapsulated crawl space and numerous upgrades throughout. This is Eastern Shore living at its finest—a rare opportunity to own a waterfront sanctuary in one of St. Michaels' most sought-after locations.T MICHAELS TUCKED AWAY ON DESIRABLE DRUM POINT NEIGHBORHOOD, MINUTES FROM THE

7149 Drum Point, Saint Michaels

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 4107450283
$1,550,000
Trappe Business Park -38± Acres in Trappe, Maryland. Exceptional industrial development opportunity in the heart of Talbot County. Trappe Business Park consists of approximately 38± acres with a preliminary plat approved by the Town of Trappe for twelve (12) industrial building lots. Lot sizes range from approximately 1.5 acres up to 11.8 acres, offering flexibility for a variety of industrial, flex, warehouse, or service oriented uses. Strategically positioned just 1,500 feet from U.S. Route 50, the property provides excellent regional access along the primary corridor connecting the Eastern Shore to Annapolis, Baltimore, and the Delaware beaches. The site is also located less than half a mile from the rapidly expanding residential and mixed use community of Lakeside at Trappe, creating built in proximity to a growing workforce and customer base. Planned infrastructure includes municipal water and sewer service, enhancing development efficiency and long term value. With approved layout, strong access, and nearby growth, Trappe Business Park presents a rare opportunity to establish or expand your footprint in one of the Eastern Shore’s most active growth corridors. Property can be purchased as a whole or by individual lot sales. Ideal for investors, developers, or end users seeking shovel ready potential in a strategic location.

4502 Old Trappe Rd, Trappe

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$1,195,000
4 Beds ⋅ 5 Baths
Enjoy historic in-town living in the heart of St. Michaels, where this beautifully maintained residence offers a rare combination of timeless architecture, a sought-after waterfront-adjacent location, and convenient access to the harbor, parks, trails, shops, and restaurants. Ideally located near the waterfront, scenic trails, park, kayak launch, and the town’s many amenities, the home provides easy access to the best of Eastern Shore living. Inside, warm and inviting interiors feature hardwood floors throughout, multiple living areas, and four wood-burning fireplaces that enhance the home’s historic character. The flexible floor plan includes four bedrooms, four and one-half baths, a dedicated office, custom built-ins, and generous storage, well-suited for a variety of living arrangements and lifestyle needs. Thoughtfully designed spaces offer both comfortable everyday living and additional room for guests, creative pursuits, work-from-home flexibility, or future customization. Outdoor features include a landscaped fenced yard designed for privacy and low-maintenance enjoyment, along with a spacious patio ideal for outdoor entertaining and relaxation. A detached cottage provides added versatility for use as a studio, workshop, or storage space. Off-street parking is an added convenience within the Historic District. Blending historic charm, adaptable living spaces, and an exceptional in-town location, this distinctive residence offers a unique opportunity to experience life in one of Maryland’s most desirable waterfront communities.

114 W Chestnut St, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415
$175,000
Real Estate not included A full-featured screen printing and embroidery business is available for sale, including all essential equipment, accessories, and an established customer base, making it a turnkey opportunity for entrepreneurs. Business Overview This type of business typically combines screen printing and embroidery services, catering to both individuals and organizations seeking branded apparel, uniforms, promotional items, and custom merchandise The business can operate full or part-time , offering personalized services ranging from monogramming and logo embroidery to multicolor screen printing for shirts, hoodies, hats, and even towels or canvas products. Embroidery is ideal for textured and thicker fabrics, while screen printing works best on smooth fabrics like cotton or blends. Equipment Included Equipment for sale encompasses everything needed to produce high-quality customized garments: Embroidery machines: Multi-head industrial Brother machines capable of handling multiple projects efficiently. 1. Screen printing presses: units provide precise, high-volume production 2. Drying and curing systems: Conveyor dryers, flash units, and heat presses for curing inks Brother embroidery machines are renowned for combining durability, advanced technology, and ease of use, offering a wide range of models suitable for beginners to professional crafters. General Features Brother embroidery machines are designed to handle various projects, from personalizing apparel to home décor embellishments. Key features include: Built-in designs and fonts: Most Brother machines come with hundreds of built-in embroidery designs, frame patterns, and lettering fonts, allowing monogramming and creative projects.

4929 Ocean Gtwy, Trappe

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$670,000
Newly listed parsonage of the Asbury Methodist Church. Offering over 2500 sqft of space, this brick structure offers many possibilities. Off street parking with circular driveway, detached brick garage, separate office area and 2 story building with full kitchen, front porch, 3 separate rooms downstairs and full basement. Currently zoned as exempt commercial, buyer is responsible for any and all due diligence regarding potential uses.

414 E Dover St, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$475,000
3 Beds ⋅ 3 Baths
Unique, one-of-a-kind property located in the heart of Tilghman Island, offering unparalleled tranquility and breathtaking water views overlooking Dogwood Harbor. Welcome to your private Eastern Shore retreat! This beautifully updated water-view home captures the essence of coastal living with sweeping views of the harbor and surrounding wildlife. Enjoy stunning sunsets and peaceful mornings from the expansive screened porch or spacious deck—perfect for relaxing or entertaining while taking in the natural beauty of the island. Inside, the home has been thoughtfully updated and features a bright, open living area and a beautifully renovated kitchen designed for both everyday living and gatherings with family and friends. The spacious primary suite offers a private bath and walk-in closet, along with panoramic water views and direct access to the second-story porch/deck with a retractable awning—an ideal place to unwind and enjoy the serene surroundings. Two additional guest bedrooms and a full bath complete the home’s comfortable and functional layout. Additional highlights include a charming screened porch, generous outdoor living spaces, a storage shed, and beautifully landscaped patios and walkways that enhance the home’s inviting coastal atmosphere. Located in the heart of Tilghman Island, this exceptional property offers the perfect opportunity to relax, boat, fish, and explore everything the Eastern Shore lifestyle has to offer.

5933 Tilghman Island Rd, Tilghman

Listing courtesy of Meredith Fine Properties. Contact: 4107149166
$339,000
4 Beds ⋅ 2 Baths
Live the Tilghman Island lifestyle just steps from the Chesapeake Bay. Perfectly positioned in the heart of historic Tilghman Island, this updated four-bedroom home offers the ability to enjoy one of Maryland's most authentic waterfront communities without the waterfront price tag. Walk to marinas, waterfront restaurants, charter fishing, Tilghman Wharf, and the iconic drawbridge, or spend your days exploring the Chesapeake by boat, kayak, or bicycle. Originally inspired by one of Tilghman's classic "W" homes, the residence blends timeless island character with modern updates. Inside, you'll find a spacious, open floor plan featuring an updated kitchen with granite countertops, stainless steel appliances, and abundant cabinetry, along with beautifully renovated bathrooms, new flooring, and a flexible layout that includes a first-floor bedroom and full bath—ideal for guests or one-level living. Three additional bedrooms and another updated full bath are located upstairs, providing plenty of space for family and friends. A new HVAC system adds year-round comfort, while the generous yard offers room for gardening, entertaining, or simply relaxing after a day on the water. Whether you're searching for a full-time residence, a weekend retreat, or an investment in one of the Eastern Shore's most charming villages, this home delivers exceptional value at an attractive price point. Experience the slower pace, rich maritime heritage, and unmatched sense of community that make Tilghman Island one of the Chesapeake Bay's hidden gems.

21524 Chicken Point Rd, Tilghman

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$7,950,000
7 Beds ⋅ 9 Baths
Presquile Manor House, originally built by the Lloyd Family circa 1800 as one of their three Plantation Houses, sits up high on the Wye River with due West Exposure. The Main House has recently gone through a two-year renovation process from top to bottom by West & Callahan Construction and Peter Zimmerman Architects Inc, with much thought and care to keep all of the historic attributes that this property deserves. The grounds are improved by a pool, tennis court, covered boat house with deep water, formal gardens, magnificent mature trees and a detached 1,670 sq ft caretaker's house. The main parcel is 10.48 acres with an additional 7.1-acre tree lined drive with a perpetual easement. This is a one-of-a-kind property and a true Talbot County piece of History. Furniture is negotiable.

26546 Presquile Dr, Easton

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$1,080,000
Looking for the ideal downtown Easton location? This beautifully renovated Colonial offers a rare opportunity—perfect as a high‑end investment property or as your personal residence with an income‑producing second unit. This stunning building features two fully updated 1,000 sq. ft. units, each finished with high‑quality materials and thoughtful design. ✦ First‑Floor Unit 2 bedrooms, 2 baths Gourmet kitchen with premium finishes In‑unit washer/dryer Fireplace and hardwood floors Relaxing front porch and covered rear deck with landlord‑provided furniture Large private parking lot behind the building Easy walking distance to Easton’s restaurants, shops, and entertainment ✦ Second‑Floor Unit Offered fully furnished Mirrors the first‑floor layout and upgrades Primary bedroom with access to a second‑story balcony Turnkey and ready for immediate occupancy Together, the two units generate $5,670 per month, making this an exceptional opportunity for investors, entrepreneurs, or owner‑occupants seeking both comfort and cash flow. With its prime location and high‑end renovation, this exquisite property won’t last. Call today to schedule your private showing.

140 S Washington St, Easton

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$1,080,000
4 Beds ⋅ 4 Baths
Looking for the ideal downtown Easton location? This beautifully renovated Colonial offers a rare opportunity—perfect as a high‑end investment property or as your personal residence with an income‑producing second unit. This stunning building features two fully updated 1,000 sq. ft. units, each finished with high‑quality materials and thoughtful design. ✦ First‑Floor Unit 2 bedrooms, 2 baths Gourmet kitchen with premium finishes In‑unit washer/dryer Fireplace and hardwood floors Relaxing front porch and covered rear deck with landlord‑provided furniture Large private parking lot behind the building Easy walking distance to Easton’s restaurants, shops, and entertainment ✦ Second‑Floor Unit Offered fully furnished Mirrors the first‑floor layout and upgrades Primary bedroom with access to a second‑story balcony Turnkey and ready for immediate occupancy Together, the two units generate $5670 per month, making this an exceptional opportunity for investors, entrepreneurs, or owner‑occupants seeking both comfort and cash flow. With its prime location and high‑end renovation, this exquisite property won’t last. Call today to schedule your private showing.

140 S Washington St, Easton

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$1,179,000
4 Beds ⋅ 3 Baths
Beautifully restored Historic Victorian in the heart of Saint Michaels. This charming home has a strong rental history, last tenant was paying $4,500 a month. From the wide, welcoming front porch to the gated, manicured yard—complete with a hammock ideal for long afternoon naps—every space is designed for comfort and relaxation. A brick walkway leads to the custom beveled‑glass entry door and into the warm, inviting family room. Inside, the home features rich pine floors throughout, a cherry kitchen with stainless steel appliances, granite countertops, and an open flow into the charming dining room. The spacious family room includes a propane stove for cozy winter days. The first floor also offers a full laundry room and an ornate powder room. The original staircase leads to the second floor, which includes three bedrooms and a renovated marble‑tile full bath. The private third‑floor primary suite offers a peaceful retreat with its own en‑suite bath. Just one block from the water—with water views from the street—this home captures the best of small‑town living. Enjoy walking access to Saint Michaels’ restaurants, quaint shops, kayaking, swimming, boating, and biking. It’s a special property ready for unforgettable memories with family and friends. Whether you're looking for a proven investment property or a beautiful home for your family, this one stands out.

101 Mulberry St, Saint Michaels

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$945,000
5 Beds ⋅ 2 Baths
Located minutes from St. Michaels this waterfront property is a boater's dream. Tilghman, is a small island big on history, nature and local lore. Situated just over the Knapps Narrows Bridge this home offers a main house with first floor primary suite. The first floor is open with custom details and just perfect for hosting friends and family. A custom spiral staircase leads to a second floor with 4 additional guest bedrooms and bath. This renovated home also has a separate 3 bay garage with a 2-bedroom 2-bath water view apartment with a nice open living and dining area and total square footage of 768. The main house has an attached 1 bedroom 1 bath in-law suite. Great space for your guests or potential for a vacation rental. A nice wide-open lawn leads you to the dock with 7 boat slips. Right on the Knapps Narrows. Tilghman is the perfect place to start making your Eastern Shore Memories. New pictures to come...

21552 Chicken Point Rd, Tilghman

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

$449,000
3 Beds ⋅ 2 Baths
The perfect renovated, water view cottage, dating back to circa 1890. Has been meticulously maintained and thoughtfully expanded over the years. Located in the waterfront Village of Neavitt (+/- 70 homes). Move-in mint condition with numerous recent upgrades. First floor primary bedroom, first floor renovated full bathroom, two additional bedrooms and full bathroom upstairs. Outdoor Living: A large screened porch and deck extend the living space outdoors, providing opportunities to enjoy views of the large backyard and breezes off the water. Detached garage/shed with electric for storage of boats in addition to space for a workshop. Solar panels on roof are owned and convey. They substantially lower electric cost to heat and cool the home. Only about 12 miles from the shops and restaurants of charming St Michaels but without St. Michael's town taxes. The village has its own park and playground as well as a public landing with a launch for canoes and kayaks. While currently on a septic system, public sewer is in the process of servicing the town, adding convenience and potentially increasing property value. Overall, this Eastern Shore retreat offers a blend of historical character, modern updates, and a desirable water view location, making it suitable for both full-time residence or part-time retreat. County sewer soon available. Neavitt yard sale moved to September while other village get-togethers/activities remain as scheduled.

6390 Bozman Neavitt Rd, Neavitt

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$899,000
2 Beds ⋅ 3 Baths
The opportunities abound for this waterfront home overlooking the Knapps Narrows. Formally, Maynard Lowery's boat building business, this residentially zoned, single-family home comes with 5 boat slips and unlimited possibilities. Can be easily expanded up to 6 bedrooms and 4 baths. The first level would make an ideal hobby area or additional living area. Handicap Accessible with elevator. Commercial potential.

21572 Chicken Point Rd, Tilghman

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

$845,000
3 Beds ⋅ 2 Baths
Renovated waterfront living with room for your fleet! Extensively renovated Cape Cod on Tilghman Island offering exceptional boating access and refined coastal living. This beautifully reimagined 3 BR, 2 BA home features 1,314 sq ft of thoughtfully designed space including two full kitchens with high-end finishes, providing outstanding flexibility for guests or extended living. Bright, upscale interiors blend modern comfort with classic Eastern Shore charm, complemented by a distinctive Standing Seam metal roof and owned solar energy system. Situated along protected waterfront with long water views and four boat slips, offering rare boating convenience and potential income opportunity. A turnkey coastal retreat ideal for full-time living weekend escape.

21560 Chicken Point Rd, Tilghman

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

$695,000
Discover the perfect addition to your portfolio with this high-visibility commercial building in Easton’s premier General Commercial (CG) district. Featuring a versatile multi-unit layout, this property is ideal for a mix of retail, professional offices, or service-based businesses. The site boasts an exceptionally rare asset for the area: an expansive, dedicated parking lot that ensures easy access for high-volume tenants and customers alike. With its strategic location, flexible floor plans, and proven potential for multiple income streams, this is a turnkey opportunity for the savvy investor looking to anchor their presence in a high-traffic corridor.

609 Dutchmans Ln, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$799,000
4 Beds ⋅ 4 Baths
📍Luxury resort-style living in the prestigious waterfront community of Easton Village! This spacious 4-bedroom, 3.5-bath home features a rare dual primary suite layout—with options on both the first and second floors—complemented by a $5,000 seller allowance to choose your own brand-new flooring. 📍The light-filled interior has been freshly painted throughout and features a versatile sunroom/office space that flows seamlessly off the main living area. Cooking and entertaining are a breeze in the gourmet kitchen, which boasts quartz countertops, a butler's pantry, and a brand-new built-in dishwasher. Retreat to the first-floor primary suite, which features an upgraded Safe Step hydrotherapy spa tub—perfect for relaxing muscles and ultimate comfort. 📍The premium upgrades continue outdoors. Enjoy low-maintenance luxury on both the welcoming front porch and the private side porch, both fully updated with durable, long-lasting Trex® decking. 📍The large, enclosed backyard offers the ultimate private retreat, beautifully framed by premium, durable HardiePlank® siding on the exterior. Additional unique features include a cozy gas fireplace and a rare 2-car garage with a heated and cooled third-bay workshop—perfect for hobbies or extra storage. 📍Live the ultimate Eastern Shore lifestyle with community access to scenic trails, boat slips, a pool, a fitness center, and a clubhouse, all just minutes from downtown Easton.

8050 Easton Village Dr, Easton

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$499,000
4 Beds ⋅ 4 Baths
RDesirable Rio Vista Duplex – Live in One Unit and Let Rental Income Help Pay Your Mortgage! Opportunities to own one of these sought-after duplexes are rare. Located in the desirable Rio Vista water-access community, this property offers potential dock access (subject to owner approval, application, and applicable fees). The building features two mirror-image units, each offering: A kitchen with a cozy eating area Spacious open-concept living and dining room Two generously sized bedrooms One full bath and one half bath Whether you're looking for an owner-occupied investment property or a fully leased income-producing asset, this duplex presents excellent potential. These units have a strong rental history and are consistently in demand. Both units are currently tenant-occupied. THIS IS WHY WE DO NOT HAVE INTERIOR PICTURES For investors seeking additional opportunities, the neighboring building at 1211 Rio Vista is also available for purchase (MLS #MDTA2012942).EDUCED - REDUCED - DO NOT WAIT TO SEE THIS DESIREABLE RIO VISTA LIVING -MOVE IN ONE

1215 Washington, Saint Michaels

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 4107450283
$499,000
4 Beds ⋅ 4 Baths
Desirable Rio Vista Duplex – Live in One Unit and Rent the Other! Rare opportunity to own a duplex in the sought-after Rio Vista community. Move into one unit and generate rental income from the other to help offset your mortgage payments. Properties like this seldom come on the market. Located in a water-access community, residents may enjoy dock access upon approval of the owner's application and payment of applicable fees. The property features two mirror-image units, each offering: Kitchen with a cozy breakfast area Spacious open-concept living and dining room Two generously sized bedrooms One full bath and one half bath This duplex presents an excellent investment opportunity with a strong rental history. Both units are currently tenant-occupied and rent well. Additional opportunity: The neighboring duplex at 1215 is also available for purchase (MLS #MDTA2012950).UST REDUCED - DONT WAIT TO LOOK AT THIS DESIREABLE RIO VISTA LIVING -MOVE

1211 Washington, Saint Michaels

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 4107450283
$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
$1,945,000
6 Beds ⋅ 6 Baths
Check out the NEW aerial photos! An exceptional opportunity in The Homes at Perry Cabin -- a rare double residence offering approximately 4,000 square feet, six bedrooms, and six full baths in a premier Saint Michaels waterfront community. adjacent to the renowned Inn at Perry Cabin and overlooking Fogg Cove just off the Miles River. This turnkey home features expansive living areas and a chef-inspired gourmet kitchen designed for elevated entertaining and showcases premium appliances, including a 60-inch extra-large refrigerator/freezer, Wolf propane cooktop, and integrated refrigerated and freezer beverage drawers thoughtfully integrated into the cabinetry. The first-floor primary suite provides effortless main-level living with a private enclosed porch and spa-like bath retreat. This combined property conveys two deep-water boat slips (6' MLW) with water and electricity, each able to accommodate a 40-foot vessel. Community amenities include kayak launch; tennis courts lined for pickleball and a private beach. A fully owned solar energy system with integrated backup battery storage provides exceptional energy efficiency and resilience adding approximately $2,000/year offset to electricity bills as well as solar income. Just a short walk or boat ride to the shops and restaurants of historic Saint Michaels, and an easy drive to Easton, Annapolis, Washington, DC, and Philadelphia. Don't miss this rare offering in one of the Chesapeake Bay's premier boating destinations. Professional photography and media forthcoming.

228 Perry Cabin Dr Unit #228 / 226, Saint Michaels

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

$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:

$775,000
8 private Offices with Kitchenette; 2 Drive in Doors, 10x11; 2 Separate Warehouses with workshop space connected to Office; Fenced in lot for outdoor storage; Walking distance to downtown Easton

304 Melfield Ave, Easton

Listing courtesy of Mackenzie Commercial R E SVCS, LLC. Contact: (410) 821-8585
$399,900
3 Beds ⋅ 2 Baths
Set on nearly an acre in the heart of Wittman, this cedar shake–sided home offers space, character, and a relaxed Eastern Shore lifestyle. Built in 1900, the 3-bedroom, 1.5-bath residence blends timeless charm with thoughtful updates for comfortable everyday living. Hardwood flooring runs throughout, complemented by a sun-filled dining room and a cozy living room with a gas fireplace and built-in shelving. The kitchen has been refreshed with new flooring, afarmhouse sink, updated butcher block countertops, and a new refrigerator—bright, functional, and well-suited for daily life while preserving the home’s original character. Outdoors, the spacious 0.86-acre lot is dotted with mature trees and beautiful landscaping, offering plenty of room to add a deck or fence. A covered front porch and outdoor shower enhance the home’s easygoing coastal feel. An oversized two-car garage with attic storage and a large driveway provide ample parking and storage. Located just 0.1 miles from Wittman Community Park, 0.3 miles from Wittman Wharf, and only 7 miles from historic downtown St. Michaels, this property offers peaceful small-town living with convenient access to waterfront amenities, dining, and shopping. A rare opportunity to enjoy space, charm, and location on Maryland’s Eastern Shore.

22582 Pot Pie Rd, Wittman

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$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:

$425,000
3 Beds ⋅ 2 Baths
Welcome to this beautifully updated cottage in the heart of St. Michaels—where modern comfort meets Eastern Shore charm. Perfectly situated within walking distance to the town’s shops, restaurants, Rails to Trails, and the renowned Maritime Museum, this single‑level home offers both convenience and a peaceful, private setting. Sitting on nearly a quarter acre, the property features a fully fenced backyard with a 6‑ft wood privacy fence, creating an ideal space for outdoor living, pets, or quiet relaxation. Inside, the home presents like new with thoughtful upgrades throughout, including hardwood flooring, recessed lighting & fresh interior paint. The kitchen and bathrooms shine with quartz countertops, tile flooring, and modern finishes. The kitchen is equipped with stainless steel appliances, new cabinetry, quartz countertops, and an under‑sink water filtration system. A front‑loading Samsung washer and dryer and a 50‑gallon water heater add to the home’s move‑in‑ready appeal. Offering 3 bedrooms and 2 full bathrooms, this well‑designed floor plan provides comfortable single‑floor living in one of the Eastern Shore’s most desirable towns. Whether you’re seeking a full‑time residence, a weekend retreat, or an investment opportunity, this St. Michaels gem delivers style, convenience, and exceptional value. The driveway access is on N Talbot St. Please see agent remarks. Try before you buy with a minimum 4-month lease. Please see rental listing! Seller may accept an offer at any time without notice.

101 Brooks Ln, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415
$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
$145,000
INVESTORS ALERT...GREAT UNIT , SECOND FLOOR LOCATION WITH ENTRANCE OFF COMMON FOYER, GREAT VISIBILITY AND PLENTY OF ON SITE PARKING , UNIT 6 NEXT DOOR IS ALSO LISTED MDTA2012864, AND CAN BE CONNECTED TO OBTAIN A LARGE OFFICE SPACE . OR CONTINUE RENTING 2 SPACES, UNIT 6 IS CURRENTLY RENTED. THE BUILDING IS WELL MAINTAINED AND UPDATED. Entire roof was replaced in 2024. Back stairway/deck that accesses Units 4/6 and providing emergency egress was completely replaced in 2025. Grading project completed in 2025. River rock, downspouts replaced, landscaping There is space to install an elevator , this has been planned when those units were constructed.

8706 Commerce Dr Unit #4, Easton

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 4107450283
$145,000
INVESTORS ALERT... , SECOND FLOOR LOCATION WITH ENTRANCE OFF COMMON FOYER, GREAT VISIBILITY AND PLENTY OF ON SITE PARKING , UNIT 4 MDTA2012870 NEXT DOOR IS ALSO LISTED AND CAN BE CONNECTED OR RENTED SEPARATE. THIS UNIT 6 IS CURRENTLY RENTED THE BUILDING IS WELL MAINTAINED AND UPDATED. Entire roof was replaced in 2024. Back stairway/deck that accesses Units 4/6 and provides emergency egress was completely replaced in 2025. Grading project completed in 2025. River rock, downspouts replaced, landscaping There is space to install an elevator , this has been planned when those units were constructed.

8706 Commerce Dr Unit #6, Easton

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 4107450283