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$9,950,000
4 Beds ⋅ 6 Baths
Set on the coveted shores of the Tred Avon River, this extraordinary waterfront estate is a rare offering, combining deep-water boating, a private sandy beach, a substantial main residence, separate guest accommodations, and an exceptional collection of lifestyle amenities. From the first approach, the property unfolds as a private Eastern Shore compound, where elegant architecture, sweeping river views, and resort-caliber amenities are seamlessly integrated into a singular waterfront setting. The four-bedroom, five-and-a-half-bath main residence is both impressive and inviting. A dramatic two-story living room features hardwood floors, a fireplace, custom millwork, and abundant natural light, while the waterside den offers a more intimate retreat with a gas fireplace, custom bookshelves, and a wall of glass framing views across the Tred Avon. A spacious screened porch and expansive Ipe decking extend the living spaces outdoors and provide direct access to the waterfront. At the heart of the home, the kitchen is equipped with a Sub-Zero refrigerator, gas cooktop, double ovens, stainless steel dishwasher, granite countertops, and white cabinetry, along with generous space for casual dining. A first-floor office and laundry room add everyday convenience, while dual staircases provide easy access throughout the home. The first-floor waterfront primary suite is a private sanctuary with its own fireplace, sitting room with custom bookshelves, two walk-in closets with custom shelving, and a beautifully appointed bath featuring a waterside soaking tub, dual vanity, and walk-in steam shower. Each additional bedroom is en suite, creating comfortable and private accommodations for family and guests. Outside, the property transforms into a private waterfront retreat. A heated lap pool, hot tub, and sandy beach create distinct places to relax along the river, while a scenic walking path winds through wildflower gardens and open space, reinforcing the estate’s remarkable sense of privacy and scale. The pool house makes outdoor entertaining effortless, with a full kitchen, stainless steel appliances, gas range, laundry facilities, and an outdoor shower. A separate three-bedroom, two-bath guest residence provides exceptional additional accommodations with hardwood floors, a full kitchen, laundry, garage, and a large deck overlooking the Tred Avon—ideal for extended family, guests, or multi-generational living while preserving the privacy of the main residence. For those drawn to the water, the property delivers. A private pier offers 6+ feet of water at mean low water, three slips, two boat lifts, water and electric—providing exceptional deep-water access for a wide range of vessels. From here, spend the day cruising the Tred Avon and exploring the waterways of the Chesapeake Bay. A rip-rapped shoreline provides protection while preserving the property’s connection to the river. With a three-car garage, irrigation system, extensive custom millwork, guest and pool houses, heated pool, sandy beach, and substantial boating infrastructure, this is far more than a waterfront home. It is a complete Eastern Shore estate—a private compound where the residences, grounds, and waterfront amenities come together to create an exceptional lifestyle on the Tred Avon.

6920 Travelers Rest Cir, Easton

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$350,000
3 Beds ⋅ 2 Baths
Solid brick 3-bedroom, 2-bath rancher situated on a quiet street just behind the hospital. This well-maintained home features a newer roof, soffits, and gutters, along with a vapor barrier, energy-efficient windows, and sliding door. The updated kitchen includes stainless steel appliances. Enjoy a gravel driveway plus convenient street parking. Ideally located close to the hospital and just minutes from downtown restaurants, shops, and amenities.

241 Brookwood Ave, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$559,000
4 Beds ⋅ 3 Baths
A myriad of possibilities come with this unique property. Two homes for the price of one. The main house offers three bedrooms with two full baths plus an attached in-laws/au-pair with two bedrooms, family room with brick hearth fireplace, one full bath, kitchen and sunroom. The main house has gleaming wood floors, kitchen with breakfast area, formal dining and living room with fireplace. Spacious primary suite with walk-in closet. The third floor is great for a workroom, studio, crafting and kids playroom. Situated on 2.1 +/_ acres with a detached 4-car garage and storage shed in a quiet country setting and just minutes to a Talbot County boat ramp.

6253 Middle Point Rd, Neavitt

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415
$525,000
3 Beds ⋅ 3 Baths
Welcome to 29796 Lyons Drive, where comfortable elegance, easy living, and the peaceful beauty of Maryland’s Eastern Shore come together. Located in a desirable 55+ community, this beautifully maintained Merion Model offers an inviting floor plan, impressive architectural details, and tranquil surroundings. Adding even more peace of mind, the home features a roof that is only 2 years old. From the moment you step inside, you’ll appreciate the home’s attention to detail, including soaring ceilings and an elegant tray ceiling in the dining room. The warm and welcoming family room is centered around a gas fireplace, creating the perfect setting for relaxing evenings or gathering with family and friends. Designed with convenient main-level living in mind, the spacious primary suite is located on the first floor and is enhanced by a beautiful tray ceiling. The private primary bath features a walk-in shower and soaking tub, creating your own relaxing retreat at the end of the day. At the heart of the home is a spectacular kitchen featuring granite countertops and beautiful 42-inch maple cabinetry, offering plenty of workspace and storage for everyday living and entertaining. The additional sunroom may quickly become one of your favorite places in the home. Enjoy your morning coffee while looking out over the stone patio and surrounding trees, where wild turkeys and deer may be among your morning visitors. Need a little extra space? A room above the garage with both heat and air conditioning provides wonderful flexibility. Create a home office, hobby or craft room, exercise space, media room, or comfortable retreat—the possibilities are yours. Whether you’re ready to simplify your lifestyle, enjoy the benefits of a welcoming 55+ community, or simply find a beautiful home where you can relax and enjoy everything the Eastern Shore has to offer, 29796 Lyons Drive is more than a home—it’s a destination.

29796 Lyons Dr, Easton

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

$1,500,000
4 Beds ⋅ 3 Baths
OPEN HOUSE ON SUNDAY FROM 2:00-4:00PM. A stunning Farmhouse completely restored/rebuilt by renown Architect Greg Wiedemann on two glorious acres meticulously maintained on a serene Choptank River Setting. it is the Quintessential "Getaway" from the hustle/bustle of life. The focus of each room is the River. There are patios, balconies and porches galore for your leisure enjoyment and viewing pleasure. The center of the home is the Dining and Kitchen area. You enter from the side porch and exit through either twin glass doors which border large windows which overlook the River onto a flagstone patio where you can enjoy outdoor dining or just relaxing by the River. Off of the Kitchen you will find the "Mud Room" and/or Laundry Room. You will find a stackable Washer Dryer and Utility Sink in this area. Also next to the Laundry room you will find a large full bath with shower. The actual Front Door to the home is on the side of the house off of the welcoming porch with a swing. The Main entrance opens to the Living Room with Large windows which front to the Choptank. One of the four bedrooms in the home is on the first floor with a large ensuite bath, There are actually two large primary bedrooms. One can use the primary bedroom on the first floor for a large family room as the upstairs bedrooms are very spacious. The second floor primary enjoys both a balcony and a screened porch. The home is in excellent condition. The two zone air conditioning systems have just been replaced. On the grounds you will find two sheds, one for utilities and the other serves as a Workshop and storage, Enjoy a 1000 foot private beach front with a dock. Within the photos, please take the time to gaze upon the variety of seasonal trees and flowering plants that adorn this two acre paradise.

31720 Ayres Dr, Trappe

Listing courtesy of Weichert, REALTORS. Contact: afitzgerald@weichertrealtors.net
$4,125,000
Zoned MXW this is one of the last remaining large parcels in the Town of Easton, Maryland Plans must be approved by Easton Planning and Zoning . See zoning for permitted uses. With approved residential uses there are some applications that will go along with an appropriate commercial applications. However the main use for this will be residential. Current leases are all cancellable and will be done a settlement.

306 Port St, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$4,125,000
Largest remaining undeveloped parcel in the Town of Easton with attractive zoning of MXW. Please review permitted applications and development requirements. Agents must represent Buyers as their agent. Existing radio towers to be removed by seller, building lease is cancelable with a small land lease to adjacent building. Reasonable due diligence time will be considered with an executed contract. Prefer Buyers use local engineering and legal counsel. Close to Easton Point and the Tred Avon with great upside potential for future development. Currently zoned MXW a special Town zoning.

306 Port St, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$160,000
Lot has been approved by the Historic commission and exterior plans available , Easton Board of zoning appeal is approved for Variances to lot lines setback and approved for Duplex of up to 1200 feet per unit .Off street parking approved by BOZA for two cars.. Lane Engineering approved drawings available...Easton Utilities has approved all services to lot......Sidewalks and curb already completed on site. Property fronts on Aurora Street and South Lane ...Exterior plans approved by Historic Commission and BUYER needs to file final interior plans to town for building permits......No impact fees paid to date......A Great Investment property in the heart of Easton

20 South Aurora, Easton

Listing courtesy of Stafford-Stafford Real Estate. Contact: 4103107755
$939,000
3 Beds ⋅ 2 Baths
Nestled in the serene enclave of Bozman, on Harris Creek this exquisite 1940s style bungalow seamlessly blends coastal charm with modern luxury, offering an unparalleled lifestyle for discerning buyers along with fantastic sunset views and a sheltered cove. Spanning 1,362+/- square feet, this detached residence boasts three spacious bedrooms and two elegantly appointed bathrooms, each designed with high-end finishes that elevate everyday living. The country-style kitchen features rich wood cabinetry and ample counter space, while the family room, conveniently located off the kitchen, invites relaxation with its warm ambiance. The primary bedroom, a true sanctuary, offers breathtaking waterfront views, allowing you to wake up to the gentle sounds of nature. The interior is adorned with beautiful wood floors that exude warmth and sophistication, complemented by ceiling fans that enhance the airy feel throughout. The bathrooms are thoughtfully designed, featuring a luxurious walk-in shower and a stall shower, ensuring a spa-like experience at home. An attic provides additional storage, while the main floor laundry adds convenience to your daily routine. Outside, the property is a true oasis, set on a generous 0.58+/-acre lot that is cleared and beautifully landscaped. The sloping rear yard leads to 98+/- feet of pristine waterfront along Harris Creek, where you can indulge in the tranquility of water views framed by lush trees and woods. This unique setting not only offers a picturesque backdrop but also provides navigable water access, perfect for kayaking or leisurely afternoons by the water. The exterior features include a charming outbuilding and a shed shop, ideal for hobbies or additional storage. An attached garage with front entry and an asphalt driveway ensures ample parking for you and your guests. Located in a peaceful riverfront community, this property is not just a home; it's a lifestyle. Enjoy the serenity of nature while being just a short drive from local amenities and attractions. Experience the perfect blend of luxury, comfort, and natural beauty in this exceptional Bozman residence, where every detail has been meticulously . Being sold with most furniture and personal possessions this is a GREAT OPPORTUNITY. RECENTLY REDUCED FOR QUICK SALE!

8090 Bozman Neavitt Rd, Bozman

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$60,000
Build your dream home on beautiful Tilghman Island! This ideally located lot is within walking distance of Sinclair Community Park, local marinas, charming shops, and popular waterfront restaurants. Stroll to the end of your street to enjoy stunning Chesapeake Bay sunsets from the park’s scenic shoreline. Tilghman Island is a beloved Eastern Shore destination known for its rich maritime heritage, working harbor, and friendly small-town atmosphere. Residents and visitors alike enjoy boating, fishing, kayaking, crabbing, and biking along quiet country roads. The island offers a relaxed coastal lifestyle while still being only a short drive to St. Michaels and other Bay communities. Public sewer connection available, making the building process straightforward and convenient. Don’t miss this opportunity to own a piece of island life—perfect for a full-time residence or a serene getaway by the Bay.

Sinclair Ave, Tilghman

Listing courtesy of Meredith Fine Properties. Contact: 4107149166
$699,000
Priced to Sell!! Positioned within the popular Talbot Commerce Park in Easton, this ±5.90-acre commercial/industrial lot presents an opportunity to secure a development-ready site in one of the Eastern Shore’s premier business hubs (approvals and permits required). Strategically located just off the Easton Bypass and U.S. Route 50, the Property offers exceptional regional connectivity, allowing for efficient access to major Mid-Atlantic markets while maintaining the operational advantages of Talbot County’s business-friendly environment. The park is fully improved with public water and sewer, paved access roads, and established infrastructure, eliminating many of the upfront hurdles typically associated with raw land development. On file are conceptual site plans, subdivision options, and architectural concept drawings. Zoned for Business Commercial / Industrial uses, Talbot Commerce Park supports a wide range of uses, including warehouse, distribution, self-storage, flex warehouse buildings, contractor yards, office uses, and more, making this site ideal for both owner-users and developers seeking flexibility in design and execution. The Property is also located within an area targeted for continued economic growth, with proximity to expanding business activity and potential eligibility for enterprise zone incentives, offering tax advantages tied to job creation and capital investment. With increasing demand for well-located industrial land and limited supply of shovel-ready sites in the region, 8992 Mistletoe Drive represents a compelling opportunity to develop immediately or hold for future appreciation within a growing commercial corridor.

8992 Mistletoe Dr, Easton

Listing courtesy of SVN/Miller Commercial Real Estate. Contact: 410-543-2440
$800,000
A prime commercial opportunity awaits at Easton Technology Park. This fully cleared 2-acre lot comes with all utilities — water, sewer, electric, and gas — already brought to the curb, making it truly move-in ready for your business. Zoned BC (Business Commercial), the property offers exceptional visibility and accessibility with direct access from Route 50. Situated directly across from Easton Airport and just minutes from the new University of Maryland Medical System Shore Regional Health Hospital, set to open in 2028, this location places your business at the heart of a rapidly growing corridor.

I-Way Court Lot #9, Easton

Listing courtesy of Meredith Fine Properties. Contact: 4107458060
$11,000,000
4 Beds ⋅ 5 Baths
Presenting "Middleville" (est. 1880), one of the largest waterfront farm and residential estates currently available in the State of Maryland. Spanning over 662 pristine acres in Talbot County, this once-in-a-lifetime landholding features 1.8 miles of shoreline and a world-class infrastructure for luxury living and elite conservation. The Residences & Amenities: The centerpiece of the Estate is the Tidewater Colonial Main Residence, meticulously renovated in 2025. Blending Coastal Charm with modern luxury, the home features: Gourmet Kitchen, equipped with custom cabinetry and top-tier luxury appliances. Waterfront Great Room, an architectural masterpiece with floor-to-ceiling glass offering expansive views of the Chesapeake Bay. Owner’s Wing, a first-floor primary suite featuring dual bathrooms and dual walk-in closets. Refined Finishes: Time-period hardwood flooring throughout, four brick wood-burning fireplaces, and durable HardiePlank siding with a metal roof. Outdoor Living: A tree-lined drive leads to a resort-style grounds featuring a swimming pool, pool house, built-in hot tub, and dedicated pickleball and basketball courts. Estate Infrastructure: 3-car garage, geothermal heating, backup generator, professional hardscaping and multiple barns and storage buildings . Additional Housing: The compound includes three private guest houses and a dedicated caretaker’s residence . The Land & Conservation: Comprised of five distinct parcels, the acreage is a diverse blend of productive agriculture and natural sanctuary. Acreage Breakdown: 390+/- acres of fertile, income-producing cropland and 175+/- acres of mature forest. Waterfowl & Wildlife: A premier destination for sportsmen, the property includes a 7+ acre stocked fishpond/waterfowl holding and six well-fed, water-controlled waterfowl impoundments designed for quality game management. Shoreline & Pier: Over 1,200 feet of shoreline revetment protects the coast. The private pier is equipped with two boat lifts and additional mooring capacity. Middleville is a "turn-key" legacy estate on Maryland’s Eastern Shore, offering a rare fusion of historic significance, 2025 modern luxury, and vast natural resources. In an era where land is the ultimate luxury, this is a unique opportunity to secure one of the region's most significant holdings.

29245 Howell Point Rd, Trappe

Listing courtesy of Holiday Real Estate. Contact: 4105247700
$649,000
3 Beds ⋅ 2 Baths
New $10k price improvement and ready by September, this 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
$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
$72,500
Tilghman Island. Clear level building lot with public sewer available. The perfect spot for your new vacation / retirement home. Excellent opportunity to make your island dream come true.

21472 Willey Rd, Tilghman

Listing courtesy of Meredith Fine Properties. Contact: 4107149166