Refine Search
Map
Sort by
$495,000
3 Beds ⋅ 3 Baths
Welcome to easy living in one of Easton's most sought-after 55+ communities. Situated on a desirable corner lot with mature landscaping, this well-maintained Thurston model offers a thoughtfully designed floor plan with a first-floor primary suite, an additional main-level bedroom and full bath, a spacious family room open to the kitchen, and a bright sunroom. Upstairs offers a private guest suite and versatile loft, perfect for visitors or a home office. Recent updates include fresh paint in select rooms. Additional highlights include hardwood flooring throughout the main living areas, a two-car garage, irrigation system, and private patio. Community amenities include a clubhouse with a fitness center and game rooms, an outdoor pool, tennis courts, and walking trails. Conveniently located just minutes from downtown Easton, shopping, restaurants, and medical facilities.

29833 Hillary Ave, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$249,500
2 Beds ⋅ 3 Baths
BUYER MUST FILL OUT APPLICATION AT HYDE PARK OFFICE AND BE APPROVED. NEW ROOF JUST INSTALLED MAY 2026! This charming and well maintained 2-bedroom, 3-bath rancher is located in the desirable Hyde Park 55+ community. Offering one-level living on one of the largest lot in the entire community. this home features a welcoming front porch that leads into a spacious living room. The open kitchen includes ample cabinet and counter space, a pantry, and a breakfast bar that overlooks the family room, perfect for everyday living and entertaining. The primary suite boasts a walk-in closet with separate full baths with a shower/tub combo and linen closet. The second suite features a large closet. A large sunroom overlooks the backyard has a separate HVAC system. Additional highlights include a huge 1-car garage with room for a workshop, additional storage room off the primary with access to the back yard and a shed with electric. The vibrant Hyde Park community offers fantastic amenities included with the ground rent, such as an outdoor pool, a clubhouse for social gatherings, fitness center, dog park, 9-hole disc golf course and shuffleboard courts. Property taxes, water, sewer, and trash services are all included, along with snow removal on paved streets and maintenance of common areas. Onsite office management provides added peace of mind. Don’t miss this opportunity to enjoy low-maintenance living in a welcoming, active adult community! Conveniently located just minutes from Easton’s shopping, dining, and entertainment options!

1 Victoria Ct, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$704,990
4 Beds ⋅ 3 Baths
Introducing the Greenbrier: Premium Coastal Luxury at The Preserve at Wye Mills. Experience the perfect blend of sophisticated design and Eastern Shore living with this exceptional , to be built executive home by Koch Homes. Showcasing an elegant architectural flow and a bright expansive open floor plan, the Greenbrier model is designed for both grand entertaining and comfortable everyday luxury. A standard feature of this property is the expansive 3 car tandem garage and full basement. Nestled just 5 minutes from the scenic Wye River and Wye River boat ramp, this specialized premium space is perfect for storing a third vehicle, kayaks, paddleboards or crabbing gear to take full advantage of water access right down the street. The upper level is an absolute retreat, boasting remarkably spacious bedrooms and massive walk-in closets. For unparalleled versatility this design offers the option to add a private on suite bath to the fourth bedroom creating a a spectacular self-contained guest suite. Situated on a premier, generously sized lot within a highly desired and scenic community, this is a rare opportunity to build a custom-tailored luxury retreat minutes from the water. Purchase for a limited time and receive $20,000 in closing cost assistance with the use of one of Koch Homes preferred lender and title company. Images show a completed version of this model with options in a different community. Final selections and features will vary. $450 quarter fee for community septic with individual grinder pump system maintained by Talbot county.

000 Quiet Hollow Ct, Wye Mills

Listing courtesy of Koch Realty, Inc.. Contact: 410-320-6422
$459,000
4 Beds ⋅ 2 Baths
Nestled in the serene Chapel Woods subdivision, this charming traditional home offers a perfect blend of comfort and functionality. With four spacious bedrooms and two full bathrooms, this residence is designed to meet your needs for both relaxation and entertaining. Step inside to discover a warm and cozy ambiance throughout. Enjoy the tranquility of your surroundings with picturesque views of trees and lush greenery right from your windows. Outside, the expansive 2.13-acre lot provides ample space for outdoor activities or simply enjoying nature. The detached garage offers plenty of room for your vehicles, toys, and tools, as well as additional storage on the second level of the garage. This home is not just a place to live; it's a sanctuary where you can create lasting memories. Experience the perfect blend of comfort, style, and nature in this delightful property. You'll have peace of mind knowing you have a new roof that is about a year old and a brand-new HVAC unit for the first floor with a 10-year warranty. The crawl space area is encapsulated and also has a dehumidifier; this helps to block moisture & protect your structure.

11598 Malvern Ln, Cordova

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

$459,990
2 Beds ⋅ 2 Baths
Welcome to the Spring Lake II, a beautifully designed home that pairs an open-concept layout with timeless Loft elements. Offering 2 bedrooms, 2 baths, and a 2-car garage, this home provides both elegance and everyday functionality. Just off the foyer, a formal dining room creates the perfect setting for hosting holidays and special gatherings. The spacious kitchen is both stunning and practical, featuring a large island and walk-in pantry to support effortless entertaining and daily living. The open and airy great room impresses with a vaulted ceiling, optional beams, and a sliding door leading to the covered patio, seamlessly blending indoor and outdoor living. A cozy fireplace with mantel and hearth adds warmth and character to the space, while the screened-in patio offers another inviting area to relax. The luxurious primary suite is a true retreat, highlighted by triple windows for abundant natural light and a gorgeous primary bath with an optional freestanding tub and walk-in closet. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

7854 Ward Brothers Cir, Easton

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$474,990
2 Beds ⋅ 2 Baths
Welcome to the Spring Lake II, a beautifully designed home that pairs an open-concept layout with timeless Loft elements. Offering 2 bedrooms, 2 baths, and a 2-car garage, this home provides both elegance and everyday functionality. Just off the foyer, a formal dining room creates the perfect setting for hosting holidays and special gatherings. The spacious kitchen is both stunning and practical, featuring a large island and walk-in pantry to support effortless entertaining and daily living. The open and airy great room impresses with a vaulted ceiling, optional beams, and a sliding door leading to the covered patio, seamlessly blending indoor and outdoor living. A cozy fireplace with mantel and hearth adds warmth and character to the space, while the screened-in patio offers another inviting area to relax. The luxurious primary suite is a true retreat, highlighted by triple windows for abundant natural light and a gorgeous primary bath with an optional freestanding tub and walk-in closet. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

29397 Jobes St, Easton

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$339,900
2 Beds ⋅ 3 Baths
Located in the desirable Martingham community, this two-bedroom, two-and-a-half-bath condominium offers comfortable living just minutes from historic downtown St. Michaels. The main level features a spacious living room with hardwood flooring and a wood-burning fireplace, a convenient half bath, and a full-season sunroom overlooking the backyard with direct access to the outdoor space. A detached one-car garage provides additional parking and storage. Upstairs, both bedrooms feature en-suite baths, including a rear bedroom with a private balcony overlooking the backyard and The Links at Perry Cabin Golf Course. Brand-new carpeting has just been installed throughout the upper level, and the home also features a brand-new water heater. Conveniently located near shopping, dining, waterfront parks, and the many attractions of downtown St. Michaels, this property offers an excellent opportunity to enjoy Eastern Shore living.

9531 Quail Hollow Dr Unit #405, St Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$1,250,000
4 Beds ⋅ 3 Baths
Experience Eastern Shore waterfront living in this charming Chesapeake Bay home, where breathtaking sunset views and a relaxed coastal atmosphere create the perfect setting for everyday living or weekend escapes. Designed to embrace the waterfront lifestyle, the property offers exceptional indoor and outdoor spaces for entertaining family and friends. A brick walkway welcomes you to the inviting front porch and foyer, where hardwood floors flow throughout the home. Recently renovated, the kitchen features white cabinetry, quartz countertops and large windows that fill the space with natural light while overlooking the front yard. The spacious living room is highlighted by a cathedral ceiling and opening to a year-round sunroom surrounded by walls of windows showcasing panoramic views of the Chesapeake Bay. The primary suite features a newly renovated bath with a tile and glass shower. Two guest bedrooms, an office and two additional beautifully renovated full baths occupy the opposite wing of the home, while the second level offers a fourth bedroom with skylights. Outside, you'll find everything needed to enjoy life on the water. The waterside pool with swim deck is complemented by a screened porch, expansive patio, covered seating area and a pool house/bar complete with air conditioning and electric. The private pier provides the perfect spot for fishing, crabbing, or simply taking in the spectacular sunsets, while the rip-rapped shoreline offers lasting shoreline protection. Additional improvements include an attached two-car garage, a storage shed with electric, and a new roof installed in 2025. Situated on high ground outside of the flood zone, this exceptional waterfront property offers direct access to some of the Chesapeake Bay's best fishing, boating, waterfront restaurants and the unforgettable Eastern Shore lifestyle.

5480 Windward Dr, Tilghman

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415
$2,895,000
4 Beds ⋅ 5 Baths
With sweeping sunset views, this picturesque estate—perfectly situation on a deepwater point with a private dock on Island Creek just off the Choptank River—offers the rare combination of privacy, acreage, and refined Eastern Shore living. Just ten minutes from Easton, Oxford, and Cambridge, the property features an impressive two‑story Tidewater Colonial of approximately 3,500± fsf that includes a first‑floor primary suite with a private library, multiple walk‑in closets, and a beautifully finished bath; two additional bedrooms and full bath upstairs; a guest apartment with separate kitchenette, bedroom and full bath; a large two‑car garage; and a stunning concrete pool framed by expansive stone patios. The current owners thoughtfully reimagined and upgraded the interior, relocating the kitchen to the waterside, expanding and renovating the spacious family room and first‑floor primary suite, adding an exceptional bar/butler’s pantry with custom cabinetry, refrigerator, dishwasher, and icemaker, and creating a central multi-purpose laundry room. Exterior features include low‑maintenance brick and siding, new roof on the renovated waterside, paved drive with ample parking, and an attached two‑car garage with a separate climate‑controlled workout room and half bath. The fully protected, riprapped shoreline spans approximately 665 feet and features a new pier with two deepwater slips (6’+ MLW), electric and water service, plus a separate kayak dock and launch. From any of the property’s many vantage points, enjoy majestic shade trees, mature landscaping, and an ever-changing panorama of natural beauty—imagine watching schools of fish and abundant waterfowl daily—making this an ideal Eastern Shore retreat.

4440 Baildon Rd, Trappe

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415
$1,499,000
3 Beds ⋅ 3 Baths
Major Price Improvement! Western sunsets and timeless waterfront living define this beautifully restored home on Town Creek in Oxford. A waterside pool, expansive entertaining deck, gazebo and private pier create an exceptional setting for enjoying life on the water. Fabulous gourmet kitchen and inviting family room with a custom built-in bar anchor the home, while warm pine floors add warmth and character throughout. Three bedrooms and three full baths include a spacious waterfront primary suite with a private second-story deck overlooking Town Creek—the perfect place to unwind while taking in spectacular western sunsets. Just moments from Oxford's waterfront park, marina, restaurants and the Oxford-Bellevue Ferry, this distinctive property is privately sited outside the Historic District and features a private pier with approximately 4 + feet of mean low water, providing easy access for boating, kayaking and paddleboarding. Sold As Is

104 Myrtle St, Oxford

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344
$395,000
2 Beds ⋅ 2 Baths
Comfortable living spaces can be found in this well-maintained 2BR/2BA townhome located just minutes from downtown Easton. Features include hardwood floors, wood-burning fireplace, newer kitchen appliances, washer and dryer. Carpeting was replaced a couple years ago. Convenient location with quick access to the Easton bypass and Rt 50, hospital and downtown.

1175 S Washington St Unit #18, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$2,995,000
4 Beds ⋅ 4 Baths
Set on 28 private acres overlooking Plaindealing Creek along the desirable Easton–St. Michaels corridor, this beautifully remodeled waterfront home offers 4 bedrooms, 4 full baths, and breathtaking panoramic views stretching across to Oxford, the Choptank River, and beyond. Positioned on an exceptional point of land, the property enjoys a rare combination of expansive water vistas, privacy, and direct access to some of the Eastern Shore’s finest boating and sporting waters. A scenic, tree-lined drive leads to the residence, where the water immediately takes center stage. Thoughtfully renovated in 2019, with numerous additional upgrades completed in subsequent years, the home is designed for both relaxed everyday living and effortless entertaining. The main level features a waterside primary suite with an exquisite ensuite bath, along with an additional guest bedroom and adjacent full bath(with sauna). The spacious living room is anchored by a brick fireplace with pellet stove insert, custom built-ins, and sliding doors opening to the waterside patio, creating a seamless connection to the remarkable setting. A well-appointed kitchen with stainless steel appliances and granite countertops adjoins the separate dining room, where spectacular water views provide a memorable backdrop for gatherings. Two other main-level rooms offer flexibility for an office, family room, exercise room, or other living needs, while a generous laundry room with built-ins and a secondary staircase adds everyday convenience. Upstairs are two additional guest bedrooms and two en-suite baths along with an adjoining bonus room ideal for guests or hobbies, and a second staircase. A true sportsman’s paradise, the property offers deep water, excellent fishing, private hunting, and endless opportunities for boating and recreation. The private pier, completed in 2023, features three slips, a boat lift, and a jet ski lift. With approximately 7' MLW, a newly riprapped shoreline, sandy beach, new BAT septic system installed in 2019, and a new roof completed in 2026, this exceptional waterfront retreat is perfectly suited for those seeking the very best of Eastern Shore living. *Approximately 24 acres are enrolled in a Forest Stewardship Plan. * Please do not drive in without an appointment-security monitoring.

26279 Deep Water Harbor Rd, Easton

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344
$410,000
3 Beds ⋅ 3 Baths
Welcome to this spacious Cape Cod home featuring three bedrooms and two and a half bathrooms. Enjoy a welcoming front porch, an attached garage, and a generous yard perfect for outdoor enjoyment. A rear porch provides opportunity for outdoor dining and evening relaxation. Inside, the great room impresses with vaulted ceilings, and the primary bathroom offers a Jacuzzi tub and separate shower. Enjoy this immaculately maintained property, ready to call home.

29152 Holly Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415
$814,990
4 Beds ⋅ 5 Baths
The Brentwood: True Executive-Style Luxury on the Eastern Shore ​Experience unparalleled scale and sophisticated design in the Brentwood, a magnificent 3,736-square-foot executive residence designed for modern luxury living. Set within a premier community featuring expansive, large home sites, this estate offers a rare and highly coveted feature for the Eastern Shore: a massive, full unfinished basement providing endless potential for future customization, a home gym, or unparalleled storage. ​The architectural design prioritizes ultimate privacy and comfort, boasting spacious bedrooms, each complete with its own private, dedicated en-suite bath. The crowning jewel of the home is the sprawling Owner’s Suite—a private sanctuary featuring an exclusive owner's sitting room, a massive walk-in closet, and a specialized wardrobe storage area designed for the ultimate organizer.Designed to blend grand indoor living with the coastal lifestyle, the Brentwood offers flexible structural options, including a sun-drenched morning room or a spacious three-car garage. Step outside to create your own private outdoor oasis on a generous home site, all while being just minutes from the scenic river for premier boating, kayaking, and outdoor water activities. The Brentwood isn’t just a home; it’s an elevated lifestyle. ​Feature & Highlight Lists ​🌟 Executive Structural Highlights ​Massive Footprint: 3,736 sq. ft. of expertly designed, wide-open living space. ​The Eastern Shore Unicorn: Rare, full unfinished basement offering incredible structural storage or future finished square footage. ​Ultimate Family/Guest Privacy: Every single bedroom features its own private, dedicated en-suite bathroom. ​Flexible Footprint: Customization options to add a bright, open morning room or expand to a 3-car garage. The Owner’s Retreat ​Private Sitting Room: A dedicated relaxation space tucked inside the primary suite. ​Expansive Walk-In Closet: A massive, boutique-style layout with a dedicated wardrobe storage area. ​🌊 Community & Lifestyle ​Large Home Sites: Generous lot sizes with ample room to engineer a custom outdoor oasis (pool, outdoor kitchen, or extensive hardscaping). ​Scenic River Access: Located just minutes from the river, offering instant access to boating, paddleboarding, and coastal outdoor recreation. The Owner’s Retreat ​Private Sitting Room: A dedicated relaxation space tucked inside the primary suite. ​Expansive Walk-In Closet: A massive, boutique-style layout with a dedicated wardrobe storage area. ​🌊 Community & Lifestyle ​Large Home Sites: Generous lot sizes with ample room to engineer a custom outdoor oasis (pool, outdoor kitchen, or extensive hardscaping). ​Scenic River Access: Located just minutes from the scenic Wye river, offering instant access to boating, paddleboarding, and coastal outdoor recreation. "Limited time" Up to $20,000 closing cost assistance if buyer uses a Koch Homes preferred lender and tile company. Talbot County maintains the communities shared treatment facility.. The other fee listed reflects the public works facility fee (sewer fee)for ongoing operation, maintenance, administration and engineering.

0000 Rustling Oaks Dr, Wye Mills

Listing courtesy of Koch Realty, Inc.. Contact: 410-320-6422
$365,000
3 Beds ⋅ 3 Baths
BRAND NEW ROOF INSTALLED SEPTEMBER 2026 & NEW HVAC 2025. Enjoy the freedom of main-level living without giving up the space to host family and friends. This beautifully maintained Lakelands home offers a first-floor primary suite, generous guest accommodations, flexible loft space, a private fenced yard, and the low-maintenance lifestyle so many Easton buyers are searching for. Additional features include multiple storage closets, a dedicated laundry room, a two-car garage, and a fully fenced backyard with patio ideal for outdoor entertaining, pets, or gardening.

29053 Superior Cir, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$599,900
3 Beds ⋅ 3 Baths
Nestled on 2± acres, this inviting property offers a peaceful setting surrounded by mature trees that provide shade and natural beauty throughout the seasons. A circular driveway creates a welcoming approach and allows for easy access to the home and detached two-car garage, which also offers excellent potential as a workshop, studio, or hobby space. Inside, hardwood flooring extends throughout the home, adding warmth and timeless appeal. The living room is filled with natural light from a charming bay window, while the screened porch provides the perfect place to relax and enjoy the tranquil surroundings. Conveniently accessed from both the dining room and family room, the porch creates a seamless connection between indoor and outdoor living spaces. The primary suite serves as a private retreat, featuring a cathedral ceiling that enhances the sense of space along with a well-appointed en-suite bath. Two additional bedrooms each offer their own en-suite bathrooms, providing exceptional comfort and privacy for family members and guests alike. Combining spacious grounds, mature landscaping, and thoughtfully designed living spaces, this Oxford property offers the perfect blend of comfort, character, and Eastern Shore charm.

4794 Sailors Ln, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$539,900
2 Beds ⋅ 1 Baths
Just reduced - Priced to sell! The perfect weekend getaway does exist—and it's more attainable than you might think. Escape the city and discover the charm of St. Michaels, one of the Eastern Shore's most beloved waterfront towns. Known for its picturesque streets, waterfront dining, boutique shopping, wineries, marinas, and laid-back coastal lifestyle, St. Michaels offers the perfect place to relax, recharge, and enjoy a slower pace of life. Welcome to 204 E Marengo Street—an affordable opportunity to own a move-in ready home just outside of the Historic District and approximately 1.5 blocks from water access, including a marina and public boat ramp. Whether you're looking for a weekend retreat, second home, or a place to enjoy extended stays on the Shore, this charming cottage offers the ideal blend of comfort, convenience, and location. Inside, you'll find bright, inviting living spaces, easy main-level living, an updated bathroom, modern HVAC, and numerous recent improvements. Major updates include a new roof (2024), upgraded crawl space with French drain, insulation, and vapor barrier (2025), updated plumbing (2025), Thompson Creek windows, HVAC and water heater (2018), plus updated appliances and plantation shutters—allowing you to move in and start enjoying the St. Michaels lifestyle immediately. Outside, your private backyard oasis awaits. Enjoy summer days by the in-ground pool, entertain at the beach-inspired outdoor bar with cable TV, or unwind after a day on the water. The detached garage with electric provides additional storage, workspace, or future possibilities. Unlike many properties in town, this home is located outside the Historic District, offering greater flexibility for future updates and improvements without Historic District oversight. Leave the traffic and stress behind and spend your weekends where others vacation. Walk to restaurants, coffee shops, boutiques, museums, waterfront parks, and marinas while enjoying one of the Eastern Shore's most sought-after destinations.

204 E Marengo St, Saint Michaels

Listing courtesy of Compass. Contact: (410) 429-7425
$719,990
4 Beds ⋅ 3 Baths
Deaming of estate living, an inground pool, and days on the water? Welcome to the Aspen model. Nestled in a premier Eastern Shore Community minutes from the scenic Wye River, this executive model offers the grand footprint of an estate home at an incredible value. Inside the thoughtful architectural design shines with a dual-staircase layout-featuring a grand front foyer entry staircase and a highly functional second staircase just off the kitchen area for effortless daily living. The second level is anchored by a massive, sweeping Owner's Suite designed as a true private santcuary. It boasts expansive , dual walk-in closets so large they can easily function as dedicated dressing rooms. Representing the second lowest base price among the builder's six exclusive models, this is a rare opportunity to secure executive -level square footage and a pool ready lifestyle. Homesite sizes vary: lot premiums apply to select parcels. For a limited time during this initial release, the builder is offering $20,000 closing assistance when utilizing Koch Homes Preferred Lender and Title Company. Fee is for the shared treatment facility. Talbot County Public Works is responsible for all operations maintenance, administration and engineering of public sewer facility. $$ Early Buyer opportunity. $$ For a limited time during this initial release, the builder is offering $20,000 closing assistance when utilizing a Koch Homes preferred lender and title company. Photos show a representative model: actual home to be built vary based on buyer selections and homesite requirements.

0000 Quiet Hollow Ct, Wye Mills

Listing courtesy of Koch Realty, Inc.. Contact: 410-320-6422
$995,000
4 Beds ⋅ 3 Baths
This thoughtfully designed 4-bedroom, 3-bathroom home features an open-concept floor plan ideal for both everyday living and entertaining. The main-level primary suite provides a private retreat with a spacious walk-in closet and an en-suite bath complete with a double vanity and glass-enclosed shower. The living room is anchored by a cozy gas fireplace and flows seamlessly into the dining area and well-appointed kitchen, featuring a gas stove and stainless steel appliances. Practical amenities include a mudroom with laundry just off the attached two-car garage, a Rinnai tankless water heater, and an efficient dual-zone heat pump system with separate upstairs and downstairs climate controls. The second floor offers additional flexibility with a bedroom, full bathroom, and a large family room—perfect for guests, a home office, media room, or recreation space. Just off the recreation room, a spacious attic provides abundant storage and offers potential for future expansion. Outside, enjoy a beautifully landscaped backyard featuring a stone patio and ample garden space, creating the perfect setting for outdoor dining, gardening, or simply enjoying the peaceful surroundings. Ideally situated in the heart of St. Michaels, this home offers exceptional proximity to the area's most beloved destinations. Located less than 200 feet from the St. Michaels Nature Trail, just 0.2 miles from Chew Street Park, and only 0.2 miles from historic downtown St. Michaels, you'll enjoy convenient access to shopping, dining, waterfront attractions, and community events. Adding to the appeal, plans are underway for the future San Domingo Creek Park at the end of W Marengo Street—a proposed 7.6-acre waterfront park focused on recreation, environmental restoration, and trail connectivity that is anticipated to become the largest waterfront park in St. Michaels. Exceptional proximity to downtown St. Michaels, future recreational amenities, modern comforts, and versatile living spaces make this home a rare opportunity in one of the Eastern Shore's most sought-after communities.

109 W Marengo St, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$419,000
3 Beds ⋅ 2 Baths
Custom built house in 2002 with first floor master suite, large family room, enclosed sunporch and two car garage. House has hardwood floors, gas fireplace with quality built in shelving, covered front porch and so much more. You won't want to miss this one!

29739 Penny Ln, Easton

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$340,000
2 Beds ⋅ 1 Baths
Charming and move-in ready, this updated 2-bedroom, 1-bath home with a flexible office space that could easily serve as a third bedroom is perfect for first-time homebuyers, downsizers, or anyone seeking comfortable, low-maintenance living. Major improvements include a new roof and siding completed in 2020, along with a whole-house generator for added peace of mind. Inside, you'll find tasteful updates throughout, creating a warm and inviting atmosphere. The oversized detached 2-car garage offers endless possibilities, providing ample space for vehicles, storage, hobbies, or the ideal workshop. Award winning school district. Conveniently located just minutes from Easton and nearby public boat ramps, this home offers easy access to shopping, dining, and all the outdoor recreation the Eastern Shore has to offer.

11994 Cordova Rd, Cordova

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545
$1,895,000
5 Beds ⋅ 4 Baths
Experience sweeping western-facing views of the Chesapeake Bay from this beautifully renovated waterfront retreat on Tilghman Island. Thoughtfully redesigned and updated in 2023, this exceptional property seamlessly blends refined coastal living with the tranquility and natural beauty of its extraordinary waterfront setting. Offered fully furnished, the home provides a truly turnkey opportunity, allowing the next owner to immediately enjoy the Chesapeake Bay lifestyle. Inside, the light-filled great room is the heart of the home, with soaring vaulted ceilings, a gas fireplace, dramatic floor-to-ceiling windows that capture breathtaking panoramic water views, and stunning sunsets. Every detail of the renovation was carefully considered to enhance both comfort and connection to the outdoors, including the addition of a screened porch with vaulted ceilings and its own fireplace, an ideal space for year-round waterfront entertaining and relaxation. The first-floor primary suite offers a private sanctuary overlooking the Bay, complete with expansive water views, a spacious en suite bath, and generous walk-in closets. Designed for effortless indoor-outdoor living, the home also features low-maintenance composite decking, multiple waterfront gathering spaces, and a heated gunite pool perfectly positioned to enjoy the surrounding scenery. For boating enthusiasts, the property is equally exceptional. A private dock equipped with a boat lift and jet ski lift provides immediate access to some of the Eastern Shore’s finest boating, fishing, and waterfront destinations. The protected rip-rapped shoreline adds both beauty and peace of mind. This is a rare opportunity to own a fully furnished, turnkey waterfront escape offering luxury, privacy, and unforgettable Chesapeake Bay sunsets, all within the laid-back charm and timeless appeal that make Tilghman Island so special.

5698 Leeward Ln, Tilghman

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$354,900
3 Beds ⋅ 2 Baths
🏡 Cute as a button Updated Rancher Easton – 29316 Will Street 🏡 Welcome to this adorable, move-in ready rancher that perfectly blends comfort, functionality, and style! Nestled in a convenient Easton location, this well-maintained home shines with thoughtful updates throughout. Step inside to discover a warm and inviting interior, ideal for everyday living or entertaining. Major improvements include a brand-new roof and newer HVAC system, giving you peace of mind for years to come. Outside, you’ll love the versatility this property offers: Detached garage complete with a private office space— Additional bonus room for storage, hobbies, or flex space Fenced backyard ideal for privacy Lovely patio area ready for outdoor dining and gatherings Whether you're downsizing, starting out, or looking for a low-maintenance retreat, this adorable home checks all the boxes. Don’t miss your opportunity to enjoy easy living with extra space where you need it most! 📍 Conveniently located near all that Easton has to offer—shops, dining, and more!

29316 Will St, Easton

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

$5,850,000
7 Beds ⋅ 6 Baths
Introducing White Swan Point, an exceptional Chesapeake waterfront estate offering one of the Eastern Shore's most commanding settings. Positioned at the confluence of Broad Creek and the Choptank River, the property enjoys nearly 5,000 feet of shoreline with sweeping western and southwestern vistas that capture spectacular sunsets, cooling summer breezes, and an ever-changing panorama of sailboats, yachts, and waterfowl. With close proximity to major metropolitan areas, this private waterfront retreat offers a rare combination of architectural quality, recreational opportunity, and lasting investment. Whether envisioned as a family compound, executive retreat, or waterfront residence for entertaining on a grand scale, the setting delivers an experience that is increasingly difficult to replicate along the Chesapeake Bay. Constructed in 2006 by its builder as their personal residence, the approximately 8,500 square foot home reflects enduring craftsmanship and design throughout. Seven ensuite bedrooms provide generous accommodations for family and guests, while soaring ceilings, three fireplaces, richly appointed living spaces, and a sunlit morning room create an atmosphere that is both elegant and welcoming. A distinctive turret crowns the residence, providing a remarkable vantage point from which to enjoy the sunset as it settles across Broad Creek. Outdoor living is at the heart of the estate. Expansive terraces, waterside porches, and beautifully landscaped gathering spaces transition naturally toward the shoreline, where the pool, pool house, outdoor kitchen, and riverfront fire pit become the backdrop for unforgettable evenings overlooking the water. Nearly every outdoor amenity has been carefully positioned to take advantage of the property's extraordinary western exposure and uninterrupted water views. For the boating enthusiast, the estate offers exceptional privacy and water access along Broad Creek, providing an ideal setting for cruising to St. Michaels, Oxford, Tilghman Island, and destinations throughout the Chesapeake Bay. Approximately 1,900+/- feet of stone revetment protects the prominent shoreline, while an additional 2,500+/- feet along the quiet waters of Bridge Creek remains preserved in its natural state, creating a diverse waterfront environment rich with wildlife and native vegetation. Beyond the residence, the property continues to offer remarkable flexibility. Approximately 13 acres are under cultivation with an additional 3.5 acres in pasture, presenting opportunities for equestrian pursuits, hobby farming, or simply preserving the estate's open landscape. A substantial 40-foot by 60-foot barn includes workshop space, equipment storage, and a second-floor caretaker or guest apartment, providing exceptional utility for managing the property or accommodating extended stays. White Swan Point represents far more than an extraordinary waterfront home. It is an opportunity to own one of Maryland's signature Chesapeake estates, where privacy, recreation, architectural quality, and timeless waterfront living come together in one exceptional offering.

24390 Deep Neck Farm Ln, Royal Oak

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 770-9255
$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
$719,900
4 Beds ⋅ 3 Baths
Welcome to 28816 Jasper Lane in the highly sought-after Cooke’s Hope community. This beautifully maintained end-unit townhome offers 4 bedrooms and 2.5 baths, including a convenient main-level primary suite complete with a walk-in closet and relaxing soaking tub. The light-filled living room features a dramatic vaulted ceiling and cozy gas fireplace, creating the perfect space to unwind or entertain. Enjoy the ease of a 2-car garage and step outside to your own picturesque backyard with a stone patio—ideal for quiet mornings or evening gatherings. Nestled in the desirable Cooke’s Hope neighborhood, residents enjoy scenic walking trails, tranquil ponds, a dog park, tennis courts, and more—bringing a true sense of community and connection to nature. A rare opportunity to enjoy peaceful living with upscale amenities you won’t want to miss.

28816 Jasper Ln, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$675,000
3 Beds ⋅ 3 Baths
Discover the perfect blend of privacy in this spacious three bedroom, 3 full bath , Colonial located in the sought-after High Banks community. Set on over 4 acres in the water-privileged section with access to the Choptank River, this home offers a bright open floor plan, durable LVP flooring, wood stove insert with marble hearth, crown molding, and a nice open kitchen with a center island ideal for everyday living and entertaining. The second floor offers a nice loft / bonus area with fireplace, spacious owners suite with WIC and attached bath, plus a walk-in attic with potential for additional living space. Step outside to your own private retreat featuring a fenced rear yard, in-ground swimming pool, full pool bath with exterior access, and an expansive composite deck with vinyl railing—perfect for summer gatherings. Additional highlights include a new roof in 2025, new water heater April 2026, Polaris pool pimp replaced Fall 2025. attached 2-car garage with workbench. New shower in primary bathroom 2025, Chesapeake Crawl space Nov 2024,. Enjoy peaceful country living while remaining close to downtown amenities. Less than a mile to Kingston Landing – a public boat ramp for easy access to the water. Fence as-is.

32930 Oyster Bank Ter, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415
$527,415
4 Beds ⋅ 4 Baths
Brand‑new Torrington with a main‑level primary bedroom—now under construction and available for a fall move‑in! This thoughtfully designed home offers 4 bedrooms and 3.5 bathrooms. The open main level features volume ceilings in the great room, creating an airy and inviting living space. Gourmet kitchen with stainless steel appliances including hood, white cabinets and quartz counters. The main‑level primary suite is a true retreat, complete with a deluxe bath including a separate soaking tub and shower. Step outside to the rear sundeck, perfect for enjoying peaceful outdoor moments or entertaining guests. Located in Lakeside at Trappe, an amenity‑rich, master‑planned community just minutes from Easton, residents enjoy a lifestyle designed for connection and recreation. Current community amenities include: Resort‑style swimming pool Bathhouse with fitness room Ping pong & cornhole Playground & sports courts Dedicated Bark Park An immersive lakeside experience is planned, offering even more opportunities to enjoy the outdoors and waterfront lifestyle. With easy access to Easton, Cambridge, and surrounding areas, Lakeside at Trappe combines small‑town charm with everyday convenience in the heart of the growing Chesapeake Bay region. ✨ Ask about builder incentives!

231 Silver Lake Ln, Trappe

Listing courtesy of Brookfield Mid-Atlantic Brokerage, LLC. Contact: (703) 420-3322
$799,900
3 Beds ⋅ 3 Baths
PUBLIC OPEN HOUSE SATURDAY 9/12 FROM 11AM-2PM ***BRAND NEW & MOVE-IN READY*** this Arts & Crafts home sits on a quaint corner lot in picturesque Saint Michaels, MD and is clad with high end finishes throughout. Step from the covered front porch into the luxurious kitchen which features stylish pistachio and linen cabinetry with satin bronze hardware, Z-Line appliances including a 36" dual fuel 6 burner range with champagne bronze accessories, artisan wood range hood, spacious center island w/breakfast bar, high end d'oro quartz countertops and herringbone tile backsplash. The living room includes a gas fireplace w/shiplap surround, custom coffered ceiling, large picture windows and a four panel Pella slider door which allows abundance of natural light and direct access to the backyard. Rounding out the main level is a flexible multi-purpose space - perfect for a formal dining room, office or a sitting room. On the upper level enjoy 3 bedrooms and two baths, including an owner's suite with walk-in closet and a luxurious spa-like bath with dual vanities, rich blue cabinetry and walk-in shower with dual shower heads and floor-to-ceiling attache calacatta tile. Additional amenities include LVP flooring throughout main level, ceramic or porcelain tile in all baths, custom light fixtures, public water and sewer, 30 year architectural singles, 92% efficient Carrier HVAC, Pella windows, 2x6 framing, R49 insulation in ceiling, R21 insulation in walls, air seal package, covered front porch and much more. All of this in a convenient location adjacent to all historic Saint Michaels has to offer. Loaded with amenities and unbound by an HOA or restrictive covenants, this one of a kind property will not last long! Schedule your private tour today!

807 Radcliff Ave, Saint Michaels

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 3019459010
$550,000
4 Beds ⋅ 3 Baths
Tucked away in a quiet country setting just minutes from downtown Easton and convenient access to Rt. 50, this well-maintained Cape Cod offers the perfect balance of privacy and accessibility. Set on a .63-acre lot backing to open space, the home features a bright and inviting main living area with wood flooring, a wood-burning fireplace, and soaring cathedral ceilings that create an open, airy feel. The layout flows easily into the dining area and kitchen, making it well-suited for both everyday living and entertaining. Offering 4 bedrooms and 2.5 bathrooms, the home also includes a versatile bonus room. Recent updates include a new rear deck, ideal for outdoor dining or relaxing while overlooking the peaceful backyard, as well as a new washer and dryer installed in 2024 and a vapor barrier added in the crawlspace for improved efficiency and maintenance. Additional features include a spacious 2-car garage and a functional layout that offers both comfort and flexibility. Backing to open space and surrounded by a quiet setting, this property delivers a more relaxed pace of living while still being just minutes from Easton’s shops, restaurants, and everyday conveniences.

10490 Longwoods Rd, Easton

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