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$729,000
4 Beds 4 Baths
Beautifully positioned as an end-unit with southern field views, this townhouse offers 2,433 square feet of living space with 4 bedrooms, 3 full baths, and 1 half bath. Recently painted throughout, the home features gorgeous hardwood floors throughout the first floor and a well-designed floor plan for everyday living and entertaining. The open-concept living and dining areas connect to the kitchen, while two-story ceilings, skylights, and large windows provide abundant natural light. A gas fireplace is the focal point of the main living area. The first-floor primary suite includes two walk-in closets and an ensuite bath. A den, true laundry room, and powder room complete the main level. The upper-level loft overlooks the main living area and provides flexible space for a home office, sitting area, or reading nook. One guest bedroom has an ensuite bath, while two additional bedrooms share a second full bath—making this the only townhouse currently available with two full bathrooms on the upper level. Ample walk-in attic storage provides additional space for seasonal items and storage. The landscaped backyard overlooks open fields and is bordered by mature trees, offering privacy and pleasant views. An attached two-car garage adds everyday convenience. Located in Cooke's Hope, residents enjoy access to ponds, walking trails, tennis courts, a fitness center, dog park, picnic pavilion, and a community dock, all just minutes from downtown Easton.

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

$995,000
3 Beds 3 Baths
New price! Amazing opportunity to be on the water in Talbot County. Waterfront home situated on Back Creek in Sherwood. Conveniently located near St Michaels and Tilghman Island, the property includes views of sunsets over Poplar Island and is located minutes from restaurants, and shopping. Interior features include hickory hardwood floors, custom built-ins, crown molding, and recessed lighting. The kitchen is equipped with stainless steel appliances, a built-in pantry, and granite countertops. The open floor plan incorporates a gas fireplace and a formal dining room. The primary suite has a walk-in shower, soaking tub, and walk-in closet. An attached three-car garage provides additional space with an upstairs bonus game/theatre room. The backyard is built for fun with a swimming pool, an outdoor kitchen with bar area, gas fire features, a hot tub, and a pool house for storage. The property also includes a 30x30 pole building with concrete floors, as well as a dock. New septic installed in 2025!

6670 Tilghman Island Rd, Sherwood

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

$489,990
3 Beds 2 Baths
BUILDER OFFERING BELOW MARKET RATE FINANCING OPTIONS ON THIS MOVE IN READY HOME!! Brand New Single Level Matisse is now Ready for Move In at Lakeside at Trappe! This home is highlighted by impressive 10-foot ceilings throughout. The kitchen is designed with white and grey cabinets, Carrara Morro quartz countertops, a gourmet stainless steel appliance package and opens to the family room and dining area which leads to the rear screened porch. The primary suite offers a private retreat with dual walk-in closets and a deluxe primary en suite bathroom featuring a soaking tub. The opposite wing houses two secondary bedrooms and a full bathroom. A well-appointed laundry room with a sink, conveniently located off the two-car garage, also functions as a practical mudroom. Located in Lakeside at Trappe, a vibrant lakeside community with a plethora of amenities and ideally located on Maryland's Eastern Shore. Lakeside at Trappe is a private retreat to live, work, and play all in one place. Community currently offers a pool, bathhouse with fitness room, ping pong, corn hole, Bark park, playground and racquet sports courts . An immersive lakeside experience also in the works! Ask about special financing opportunities and closing costs!

1553 Lake Tahoe Dr, Trappe

Listing courtesy of Brookfield Mid-Atlantic Brokerage, LLC. Contact: (703) 420-3322

$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

$395,000
3 Beds 2 Baths
Online Bidding Open: https://www.auction.com/details/11778-old-skipton-rd-cordova-md-1921078 High Visibility Corner Property on Busy Route 50 - Perfect for Living & Business! Exceptional Opportunity in Cordova, MD! This stunning corner property boasts almost 1.5 acres of land on Route 50, offering high visibility and traffic flow. This renovated home is perfect for owner living and operating a good-sized low profile retail business, such as a real estate, insurance agency, law firm, veterinarian, doctor, travel agency, potential billboard signage, solar panels, agricultural products sales, backyard appliances & furniture, sheds, construction and show room co. Renovated from Top to Bottom 2021-2025* - New Roof - New Windows - Modern Kitchens - Updated Bathrooms - New Electrical Fixtures - Top-of-the-Line Appliances - And much more! Land and Zoning: - Plenty of room for parking and outdoor displays - Prime Location: - Corner of Old Skipton Rd and Ocean Gateway - Across from Councell Farms, a well-known agricultural landmark - High traffic flow on Route 50 Don't Miss Out! This property offers endless possibilities for entrepreneurs and families alike. Contact us today to schedule a viewing and make this exceptional property yours! Additional Details: - Property Size: Approximately 1.34 acres - Zoning: A2. We look forward to working with you to attain a mutually beneficial sale.

11778 Old Skipton Rd, Cordova

Listing courtesy of Taylor Properties. Contact: 3019702447

$399,000
3 Beds 2 Baths
Unbelievable price reduction! Located about 12 miles from St Michaels, Neavitt is a charming village of 60+ houses at the end of a peninsula. The village has a park and playground, public landing with a launch for canoes, and an active community association that stages events and operates its own lending library. 6403 was renovated and expanded in 2011 and the layout adapted for modern living, with light-filled rooms, a cleverly updated floor plan, and direct views of Balls Creek. Features include a skylit first floor primary suite, spacious great room, an eat-in kitchen with Kraftmaid cabinets...but no St Michaels taxes! The two adjacent properties are being renovated. Each will be valued at over $900,000 when completed!

6403 Bozman Neavitt Rd, Neavitt

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

$895,000
6 Beds 6 Baths
Attention investors huge price reduction!!! This custom-built duplex, located in the heart of historic Easton, is a one-of-a-kind investment opportunity. Featuring three bedrooms and two and a half baths in each home, the homes offer an ensuite primary bedroom complete with a walk-in closet and private bath. Designed with modern luxury in mind, it includes new stainless-steel appliances, Marvin windows, a rich wood front door, and high-end luxury vinyl plank flooring. The driveway is elegantly finished with pavers, adding to the home's curb appeal. Equipped with charging station for each unit for electric vehicles. As a newly constructed property, it combines timeless charm with contemporary finishes—perfect for homeowners or investors alike. Rental income is $3,100. Owner will consider some owner financing.

607 North Street, Easton

Listing courtesy of Meredith Fine Properties. Contact: 4108226272

$8,495,000
6 Beds 11 Baths
NEW PRICE! Located minutes from downtown St. Michaels, “Aqua Vitae” the waters of life, sits on 8.6 private acres on Harris Creek, a Chesapeake Bay tributary. This custom-built offering w/ over 400’ of direct water frontage is comprised of 3 magnificent structures: a grand main residence, guest cottage, & “party barn” all highlighted by a waterside pool, pier w/ 4’ MLW, pine grove, putting green, extensive landscaping & incomparable craftmanship. The 12,000 SF main residence, positioned to prioritize water views, welcomes you via prominent double lead-glass doors & a grand 3-story foyer w/ dual-staircase. The “river room” w/ 2-story octagon copula offers 270◦ views of the property & creek. The TV room w/ 3 exposures & gas-burning fireplace offers double French doors on two sides leading to the wrap-around flagstone patio. The stunning gourmet kitchen is a true chefs dream. Offering oversized island, built-in media/storage cabinet, coffered ceiling, fireplace, 3 sinks, double Subzero fridges w/ freezer drawers, 2 beverage drawers, 3 dishwashers, Wolf microwave & a stainless-steel Lacanche range with 6-burners, pot warmer, warming oven, & 2 ovens. Complimenting the kitchen is a large walk-in pantry w/ dishwasher, sink & extra freezer in hall. Off the kitchen is a covered porch w/ gas fireplace & “ghost’ screens, a perfect spot to enjoy evenings. A large open dining room has 2 custom built-in display cases. The grand salon w/ bay window, gas-fireplace & intricate mantel is reminiscent of Paris. Adjoining the salon is the handsome 2-story curly cherrywood library w/ custom display cases & leaded-glass pocket doors. The adjoining climate-controlled wine room has a wet bar & storage for 750+ bottles. Wood floors flow throughout the entire main level. The main level is completed by an office, powder room & laundry to service the pool, 2 additional powder rooms, elevator to all 4 levels, mud/dog room, rear spiral staircase, guest suite w/ ensuite bathroom, & 2-car attached garage. The 2nd level offers a generous primary suite w/ fireplace & full length terrace overlooking the water. Her wing features dressing room w/ custom built-ins, separate sitting room, & a luxurious bathroom w/ marble tile, separate shower, jetted tub, & vanity. His wing offers an office w/ fireplace, paneled closet leading to separate bathroom w/ shower, travertine stone, & vanity. From his office access the 2nd level of library, open to below. Just off of the primary suite is a bar area/kitchen. 3 additional bedrooms, each w/ ensuite bathroom, and a laundry room complete the 2nd level. The 3rd level offers theater/rec room, play area, bedroom w/ ensuite bathroom, powder room, & ample storage. The lower-level houses utilities, storage, & enough room for an exercise area. The charming guest cottage sits amongst extensive landscaping. The main level offers a full kitchen, dining area, living room, sunroom, large family room, 2 bedrooms w/ shared bathroom, additional guest bathroom, & large entertaining room. Upstairs is a full bedroom w/ ensuite bathroom. The unfinished lower level offers storage. The party barn originally built for boat storage was designed to look like an old Pennsylvania barn w/ 4’ of stone around the base. Flanked by 2 garage wings allowing for 4+ cars & capped w/ a cupola, the shingled-style barn has two large doors on either side of the building that allow for a trailered boat or 4+ more cars. The 2nd level is a loft w/ sleeping/living area w/ full bathroom, plumbed for potential kitchenette, front & rear terraces, & a spiral staircase to a crow’s nest w/ amazing views. There is a full property generator & a dog run w/ kennel just off the rear. Outside enjoy the benefits of beautiful shore living amongst the verdant grounds, mature landscaping & exceptional views. The pier offers 4’ MLW & the shoreline is fully rip-rapped w/ natural plantings.

8620 Bozman Neavitt, Saint Michaels

Listing courtesy of Washington Fine Properties, LLC. Contact: info@wfp.com

$699,000
Last Waterfront buildable lot with brand new Dock in Easton Club - Build your Dream Waterfront Home! This .57 acre lot on the Tred Avon River, minutes to downtown Easton. Purchase includes a pier permit in hand, architectural plans for a Coastal Design homeowner willing to include in the sale, Buffer management plan implemented. Lot offers 150’+ of shoreline, high elevation (16 feet above river), no flood insurance needed, high enough for a basement, 1/2 acre allows for a house, pool, and generous size yard. Easton Club Amenities include all grass cutting, street snow removal, common area maintenance and community pool. Easton Utilities services include natural gas, electric, water and sewer, high speed internet and cable. Call today for your own private tour

28522 Waterview Dr, Easton

Listing courtesy of Meredith Fine Properties. Contact: 4108226272

$1,945,000
Your Custom Dream Waterfront Home Awaits! This rare, build-ready lot offers a blank canvas for you to craft your perfect Eastern Shore estate with spectacular, panoramic views! The 2.9 acre waterfront lot in the Bachelor Pt section of Oxford offers 180 degree panoramic views stretching across the majestic Choptank River. Enjoy the peace of mind of a recently installed rip-rap shoreline over an estimated 569 feet of protected waterfront, providing long-term erosion protection and maintaining your valuable waterfront. The property also includes a new dock setup, featuring a heavy-duty 16,000 lb boat lift and two additional lifts perfect for jet skis. The lot is located within Oxford town limits, offering the advantage of access to public water and sewer hook-ups. Final approval has been given from the Oxford Planning Board for the building plans the current owner proposed providing a massive head start on your construction timeline. Those plans can be included in the sale of the lot and while you may modify them to suit your taste, having approved plans means the property is truly "build-ready." Simply choose your builder and start constructing your dream!

4480 Bachelors Point Rd, Oxford

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

$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

$979,000
4 Beds 4 Baths
No showings until Aug. 25, 2026. Stunning and spacious, this 4703-square-foot residence rests gracefully on a meticulously landscaped 2-acre parcel adorned with majestic trees. A tranquil goldfish pond, home to over 40 fish, adds a serene touch and can remain with the property, or the owner can rehome the fish. Upon entering, you're greeted by soaring 9+ foot ceilings and an impressive cathedral ceiling in the great room, complemented by recessed lighting throughout the home. The home features cutting-edge Geo-thermal heating and central air conditioning for comfort in all seasons. Entertainment options abound, with a well-appointed wet bar complete with a fridge. Luxurious flooring finishes include marble, hardwood, and Berber carpet upstairs. Dual primary bedroom suites on the main level offer versatility, one boasting a private deck overlooking the picturesque fishpond and gas fireplace. Each suite includes a spacious walk-in closet. The home offers an intercom. A large loft with a catwalk offers a commanding view of the main living area, enhanced by a striking window wall. Relax on the screened porch or enjoy the outdoors from the expansive front porch adorned with stately columns. Or the rear exterior charm is found on the deck with brick façade and wrought-iron railings. The home office/den and convenient laundry room are on the main level for added functionality. With four bedrooms—two upstairs and two downstairs—and 3.5 bathrooms, there's ample space for family and guests alike. Crown mouldings in the lower level and large columns throughout the interior add a touch of elegance. The gourmet kitchen is a chef's delight, featuring granite countertops, all-new stainless-steel appliances, and a double-wall oven. A breakfast room and formal dining room, open and defined by elegant columns, provide flexible dining options. This home offers an open main level, kitchen, breakfast area, living room, dining room, great room and large foyer. Blacktop Driveway and parking area, and 3 car garage. Additional features are the unique advantage of being one of only three properties excluded from HOA fees. This exceptional property offers a rare blend of luxury, functionality, and serene surroundings, making it truly one-of-a-kind.

32675 Discovery Dr, Easton

Listing courtesy of Keller Williams Select Realtors of Easton. Contact: 4106907356

$315,000
Located in the heart of Easton’s medical and healthcare district—and just moments from Route 50—this 1,500± sq. ft. end-unit commercial condo offers an exceptional opportunity for medical, dental, or professional office use. If you’re ready to own instead of rent, this space delivers the flexibility, infrastructure, and location your business needs. Thoughtfully designed with a highly functional layout, the unit features a welcoming waiting room, dedicated reception area, two restrooms, five office/exam rooms, break room, equipment room, sterilization area, and mechanical room. Every treatment room includes a sink and is fully plumbed for dental chairs with water, suction, and air at both ends. Wiring is already in place for digital dentistry, panoramic X-ray, and data systems. All rooms also include Radon fans installed during COVID to create negative pressure—an added layer of safety and value. Additional perks include 220V service for autoclaves and laundry hookups. Interior walls can be easily reconfigured to suit your practice or workflow. Recent updates include a new roof and freshly repaved parking lot. Shared operating costs—trash, lawn care, landscaping, and water—are divided among the four units based on square footage.With ample parking and a prime location surrounded by established healthcare providers, this space is a rare chance to elevate your business while building equity. Perfect for medical, dental, therapy, or professional users looking to stop paying rent and secure a smart long-term investment. Bring your buyers. Bring your business.

508 Cynwood Dr Unit #A, Easton

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