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$750,000
3 Beds ⋅ 4 Baths ⋅ MDTA2014614 MLS
Extremely private 3 BR 3 1/2 BA house on 4 acres with a pool! This property features a huge, finished bonus/game room over the garage with separate hvac zone, large family room with vaulted ceiling, first floor mater suite with an extremely well-done tile bathroom and absolutely complete privacy!

30420 Deep Branch Rd, Trappe
$250,000
4 Beds ⋅ 3 Baths ⋅ MDTA2014604 MLS
Welcome to 3759 Rumsey Drive, Trappe, MD, located in the “La Trappe Heights” community; within the town limits of Trappe and connected to public water and sewer. This spacious home offers 4 bedrooms and 2.5 bathrooms, making it an excellent opportunity for buyers looking to add their personal touches. Being sold strictly sold AS-IS! This property is being sold strictly AS IS. The seller will make no repairs or improvements. Buyers are encouraged to conduct any inspections they deem necessary for informational purposes. This is a great opportunity for investors, renovators, or buyers looking to build equity while enjoying the convenience of an in-town location. The main level features a comfortable spacious living area with a wood-burning fireplace, a formal dining area, along with a kitchen/dining combo area as well. A convenient half bath, and access to the rear deck, perfect for relaxing or entertaining. The home also includes an attached one-car garage for parking and additional storage. Upstairs, you'll find all four bedrooms. The primary suite includes a private bathroom with a walk-in shower, while the second full bathroom, located off the hallway, features a tub/shower combination to accommodate family and guests. Outside, enjoy a spacious rear yard complete with a storage shed for lawn equipment, tools, or seasonal items. Please note that the HVAC system provides heating and cooling to the first floor only that was installed six years ago. The hot water tank is two years old. With some TLC this home is truly a gem in the lovely town of Trappe, Maryland.

3759 Rumsey Dr, Trappe
$1,900,000
3 Beds ⋅ 2 Baths ⋅ MDTA2013664 MLS
Talbot County Farm With Country Home, Multiple Outbuildings And Tillable Ac This exceptional farm in Talbot County, Maryland, presents a rare opportunity to own a highly productive Eastern Shore property that combines agricultural value, quality improvements, and premier recreational appeal. Situated in a region known for its fertile soils and strong farming history, this 90 acre home farm offers a balanced mix of tillable acreage, improved structures, and wildlife habitat, making it well-suited for farming operations, outdoor recreation, and long-term land investment. The property has a proven track record of row crop production, including corn, soybeans, and wheat. A diverse and productive soil profile supports continued agricultural use, with primary soils consisting of Mattapex silt loam and Nassawango silt loam across the majority of the fields. Additional areas include Mattapex-Woodstown soils located within previously enrolled CRP sections and wooded portions of the farm. These soils are well regarded across the Eastern Shore for their consistency and productivity, providing a solid foundation for both commercial farming and conservation practices. The farm is zoned agricultural, allowing flexibility for a variety of uses, including crop production, recreational enjoyment, and potential enrollment in conservation programs. A large portion of the acreage is tillable, offering income potential or lease opportunities, while the remaining mix of timber and habitat enhances the property's recreational value. At the center of the property sits a well-maintained 1,966 square foot brick ranch-style home built in 1997. The residence offers three bedrooms and two full bathrooms and has been thoughtfully designed for both comfort and functionality. The main living area features a spacious living room with a knotty pine accent wall and bowed window that brings in natural light. The dining room includes chair rail detailing, tongue-and-groove paneling, and a built-in glass-front cabinet, creating a functional and inviting setting. The kitchen is well-appointed with wood cabinetry extending to the ceiling, crown molding, stainless steel appliances, and a center island with seating. A pass-through connects the kitchen to the dining area, improving flow for daily use and gatherings. French doors lead to a sunroom that overlooks the surrounding farmland and wooded edges, providing a consistent view of the property throughout the seasons. The primary suite includes a private bathroom with a deep jetted soaking tub. Additional features of the home include a covered front porch and an attached two-car garage. Supporting the agricultural operation are several outbuildings, including a milk house and two additional structures, highlighted by a custom-built steel building. These improvements provide space for equipment storage, workshop use, and potential game processing. From a recreational standpoint, this Talbot County farm offers strong hunting opportunities. A large pond, complete with a strategically placed hunting pit, is heavily utilized by migratory Canada geese during the season. The combination of open ground, water, and surrounding timber creates an ideal setup for waterfowl hunting. The property also supports a healthy population of whitetail deer, adding to its appeal for hunting and outdoor recreation. For buyers seeking additional acreage, an adjoining 82.54 acre tract is also available. This parcel includes a large portion of tillable ground, with sections previously enrolled in CRP. The additional tract provides an opportunity to expand the farming operation, increase recreational use, or secure additional investment acreage. It may be purchased together with the home farm or separately, offering flexibility for a range of buyers. It's l Property taxes shall be based on the acreage as determined by the Buyer’s survey and the acreage conveyed. Taxes will be prorated proportionally from the total parent tract of 582 acres.

3750 Windy Hill Rd, Trappe
$1,900,000
MDTA2013622 MLS
Talbot County Farm With Country Home, Multiple Outbuildings And Tillable Ac This exceptional farm in Talbot County, Maryland, presents a rare opportunity to own a highly productive Eastern Shore property that combines agricultural value, quality improvements, and premier recreational appeal. Situated in a region known for its fertile soils and strong farming history, this 90 acre home farm offers a balanced mix of tillable acreage, improved structures, and wildlife habitat, making it well-suited for farming operations, outdoor recreation, and long-term land investment. The property has a proven track record of row crop production, including corn, soybeans, and wheat. A diverse and productive soil profile supports continued agricultural use, with primary soils consisting of Mattapex silt loam and Nassawango silt loam across the majority of the fields. Additional areas include Mattapex-Woodstown soils located within previously enrolled CRP sections and wooded portions of the farm. These soils are well regarded across the Eastern Shore for their consistency and productivity, providing a solid foundation for both commercial farming and conservation practices. The farm is zoned agricultural, allowing flexibility for a variety of uses, including crop production, recreational enjoyment, and potential enrollment in conservation programs. A large portion of the acreage is tillable, offering income potential or lease opportunities, while the remaining mix of timber and habitat enhances the property's recreational value. At the center of the property sits a well-maintained 1,966 square foot brick ranch-style home built in 1997. The residence offers three bedrooms and two full bathrooms and has been thoughtfully designed for both comfort and functionality. The main living area features a spacious living room with a knotty pine accent wall and bowed window that brings in natural light. The dining room includes chair rail detailing, tongue-and-groove paneling, and a built-in glass-front cabinet, creating a functional and inviting setting. The kitchen is well-appointed with wood cabinetry extending to the ceiling, crown molding, stainless steel appliances, and a center island with seating. A pass-through connects the kitchen to the dining area, improving flow for daily use and gatherings. French doors lead to a sunroom that overlooks the surrounding farmland and wooded edges, providing a consistent view of the property throughout the seasons. The primary suite includes a private bathroom with a deep jetted soaking tub. Additional features of the home include a covered front porch and an attached two-car garage. Supporting the agricultural operation are several outbuildings, including a milk house and two additional structures, highlighted by a custom-built steel building. These improvements provide space for equipment storage, workshop use, and potential game processing. From a recreational standpoint, this Talbot County farm offers strong hunting opportunities. A large pond, complete with a strategically placed hunting pit, is heavily utilized by migratory Canada geese during the season. The combination of open ground, water, and surrounding timber creates an ideal setup for waterfowl hunting. The property also supports a healthy population of whitetail deer, adding to its appeal for hunting and outdoor recreation. For buyers seeking additional acreage, an adjoining 82.54 acre tract is also available. This parcel includes a large portion of tillable ground, with sections previously enrolled in CRP. The additional tract provides an opportunity to expand the farming operation, increase recreational use, or secure additional investment acreage. It may be purchased together with the home farm or separately, offering flexibility for a r Property taxes shall be based on the acreage as determined by the Buyer’s survey and the acreage conveyed. Taxes will be prorated proportionally from the total parent tract of 582 acres.

3750-A Windy Hill Rd, Trappe
$5,995,000
6 Beds ⋅ 6 Baths ⋅ MDTA2013522 MLS
Wilderness Estate- This quintessential Eastern Shore farm is located along the Choptank River in Trappe, Maryland. Comprised of 47± acres, with original structures that are impeccably well-kept and improved with modern amenities, The Wilderness provides a unique opportunity to enjoy the best of the Eastern Shore. Surrounded by open space and preserved farmland with proximity to Oxford, Easton, Cambridge, and St. Michaels, The Wilderness is sure to please the discerning buyer. Sited among large waterfront estates, The Wilderness enjoys privacy and a commanding presence with old-growth trees, broad southerly views, and deep water. The scope of improvements includes the primary residence, waterside guest cottage, beach house, pool, pier, tennis court, early 20th-century barn, and a host of accessory structures for life on the farm. Visit the virtual tour for an inside look. The main house has great historical significance not only for the original owner’s grandson who lived there and served two terms as the Governor of Maryland but also for its place in the development of Maryland’s domestic architecture, as noted on two markers from the Maryland Bicentennial Commission and the Maryland Historical Society. The smaller and original of the two brick wings dates from the late 18th century and the larger wing from the early 19th century. The house’s architecture is unusual in that the 19th-century wings telescope up, instead of down, from the original wing. The white brick, black shutters, and historical olive green trim color are a serene palette against the house’s majestic specimen trees around the property, including a gigantic Sycamore that was at one time, the largest of its species in Maryland. The long white gravel drive under the sheltering canopy of mature trees passes by the barn and other outbuildings then curves around the front of the house. Brick steps lead up to the front porch of the early 19th century wing opening into a gracious foyer and stair hall with an elegant elliptical arch that rests on pilasters at the side walls to separate the public from private areas of the house. A French door at the rear of the foyer frames a vista of the lawn and Choptank River. To the side of the foyer are two identical parlors at the front and rear corners of the house. Both rooms have magnificent fireplace mantles and surround; one is a 1740 hand-carved mantel by noted English artisan woodcarver Grinnling Gibbons and the other is a 1780 mantel surrounded by the famous English architect and artisan, Robert Adam. The main floor of the 18th-century wing contains a spacious living room, dining room, original kitchen, and larger kitchen, pantry, two powder rooms, and a stunning sunroom connecting to a terrace along the rear of the house overlooking the Choptank River. Part of this wing was the final addition to the original home. The second floor of the 19th-century wing contains two bedrooms over the two parlors below with fireplaces and walk-in closets and two baths. The 18th-century wing and later addition contain an artist’s studio with cabinetry and sink that has a myriad uses– TV room, arts and crafts room. The primary suite is located at the rear corner of this wing. It has a fireplace flanked by single windows and another window on the rear wall for panoramic views of the mature landscape and the Choptank River. Two baths complete the suite, with one bath off a hall for access from the art studio. Two stairs access the attic level; one in the 18th-century wing leads to two bedrooms and one bath. The main stair in the 19th-century wing leads to a large game room and another cozy bedroom ensuite.

27293 Southside Island Creek Rd, Trappe
$2,500,000
MDTA2012874 MLS
Discover one of Talbot County’s rare farms that combines productive farmland, waterfront, and exceptional recreational opportunities. This 105.72-acre agricultural property features approximately 80± acres of tillable ground and is well suited for continued farming, income production, or long-term land investment. The open farmland is framed by wooded perimeter lines with a mixture of mature hardwoods and softwoods, including pine and oak, providing privacy, scenic beauty, and excellent wildlife habitat. The property is zoned agricultural, offering flexibility for farming, recreation, or investment use. The tillable acreage carries an overall NCCPI rating of approximately 57.3, indicating solid, productive ground suitable for row crops, small grains, and conservation programs. The farm boasts over 2,500 feet of water frontage on Miles Creek, offering excellent duck and goose hunting opportunities. The property is located on a known migratory flyway for ducks and geese along the Chesapeake Bay, making it a proven waterfowl destination. A network of trails through the wooded areas leads to a cleared waterfront area on Miles Creek featuring a dock and picnic table, ideal for family activities, swimming, and fishing. A small point along the creek includes a strategically placed booby blind, positioned for effective duck and goose hunting. Additional amenities include multiple duck blinds on Miles Creek and a goose pit. The historic two-story farmhouse, dating to the early 1900s, offers five bedrooms and one full bathroom and features a new roof and siding. Beginning with the main floor, the home offers a large living room, dining room, kitchen, and the first of five bedrooms. The second floor includes four large bedrooms and a full bath. The residence is accessed by a private driveway off Saulsbury Road, providing convenient access while maintaining a high level of privacy. A small shed next to the home provides additional storage. This property is income-producing, with revenue potential from farming operations, CRP enrollment, and hunting leases, making it a versatile investment opportunity, productive farm, or private recreational retreat with waterfront access. Property is being offered in cooperation with Casey Kennedy and Whitetail Properties.

4108 Saulsbury Rd, Trappe
$2,500,000
5 Beds ⋅ 1 Baths ⋅ MDTA2012590 MLS
Discover one of Talbot County’s rare farms that combines productive farmland, waterfront, and exceptional recreational opportunities. This 105.72-acre agricultural property features approximately 80± acres of tillable ground and is well suited for continued farming, income production, or long-term land investment. The open farmland is framed by wooded perimeter lines with a mixture of mature hardwoods and softwoods, including pine and oak, providing privacy, scenic beauty, and excellent wildlife habitat. The property is zoned agricultural, offering flexibility for farming, recreation, or investment use. Property is being offered in cooperation with Casey Kennedy and Whitetail Properties. The tillable acreage carries an overall NCCPI rating of approximately 57.3, indicating solid, productive ground suitable for row crops, small grains, and conservation programs. The farm boasts over 2,500 feet of water frontage on Miles Creek, offering excellent duck and goose hunting opportunities. The property is located on a known migratory flyway for ducks and geese along the Chesapeake Bay, making it a proven waterfowl destination. A network of trails through the wooded areas leads to a cleared waterfront area on Miles Creek featuring a dock and picnic table, ideal for family activities, swimming, and fishing. A small point along the creek includes a strategically placed booby blind, positioned for effective duck and goose hunting. Additional amenities include multiple duck blinds on Miles Creek and a goose pit. The historic two-story farmhouse, dating to the early 1900s, offers five bedrooms and one full bathroom and features a new roof and siding. Beginning with the main floor, the home offers a large living room, dining room, kitchen, and the first of five bedrooms. The second floor includes four large bedrooms and a full bath. The residence is accessed by a private driveway off Saulsbury Road, providing convenient access while maintaining a high level of privacy. A small shed next to the home provides additional storage. This property is income-producing, with revenue potential from farming operations, CRP enrollment, and hunting leases, making it a versatile investment opportunity, productive farm, or private recreational retreat with waterfront access.

4108 Saulsbury Rd, Trappe
$499,990
4 Beds ⋅ 3 Baths ⋅ MDTA2012186 MLS
Enjoy the serenity of country living just minutes from both downtown Easton and Cambridge! This spacious four bedroom, two and a half bath home offers over 3,400 square feet of living space and sits on nearly an acre (.96+/-) with covered front porch and nice rear deck with views of open fields/farmland. This solid house offers a comfortable layout on both levels and it's perfect for both everyday living and entertaining. The main level features a large two story foyer with beautiful staircase, large family room, open kitchen with breakfast nook and beautiful bay window, separate dining room, and sunroom with vaulted ceiling, skylights, wood burning fireplace and beautiful open views of farmland. Upstairs, the primary suite is like a private retreat with it’s own bathroom, walk in closet and balcony. Three additional bedrooms and bath complete the second floor. Attached two car garage with private circular drive surrounded by mature trees for privacy. The home features a new roof (2025), a new well, new septic system (2025) and new HVAC (2022). Within a mile of Ferry Point Marina, Waterfront State Park and Choptank Fishing Pier. Close to all of downtown Trappe/Easton/Cambridge shopping, restaurants, churches and medical facilities.

2669 Ocean Gtwy, Trappe
$8,750,000
6 Beds ⋅ 6 Baths ⋅ MDTA2006798 MLS
Wilderness Estate- REVISED OFFERING INCLUDES 5 PARCELS 6.27.25- This quintessential Eastern Shore farm is located along the Choptank River in Trappe, Maryland. Comprised of 234 acres, with original structures that are impeccably well-kept and improved with modern amenities, The Wilderness provides a unique opportunity to enjoy the best of the Eastern Shore. Surrounded by open space and preserved farmland with proximity to Oxford, Easton, Cambridge, and St. Michaels, The Wilderness is sure to please the discerning buyer. Sited among large waterfront estates, The Wilderness enjoys privacy and a commanding presence with old-growth trees, broad southerly views, and deep water. The scope of improvements includes the primary residence, waterside guest cottage, beach house, pool, pier, tennis court, early 20th-century barn, and a host of accessory structures for life on the farm. Visit the virtual tour for an inside look and appreciation for the scope of this offering. The main house has great historical significance not only for the original owner’s grandson who lived there and served two terms as the Governor of Maryland but also for its place in the development of Maryland’s domestic architecture, as noted on two markers from the Maryland Bicentennial Commission and the Maryland Historical Society. The smaller and original of the two brick wings dates from the late 18th century and the larger wing from the early 19th century. The house’s architecture is unusual in that the 19th-century wings telescope up, instead of down, from the original wing. The white brick, black shutters, and historical olive green trim color are a serene palette against the house’s majestic specimen trees around the property, including a gigantic Sycamore that is the largest of its species in Maryland. The long white gravel drive under the sheltering canopy of mature trees passes by the barn and other outbuildings then curves around the front of the house. Brick steps lead up to the front porch of the early 19th century wing opening into a gracious foyer and stair hall with an elegant elliptical arch that rests on pilasters at the side walls to separate the public from private areas of the house. A French door at the rear of the foyer frames a vista of the lawn and Choptank River. To the side of the foyer are two identical parlors at the front and rear corners of the house. Both rooms have magnificent fireplace mantles and surround; one is a 1740 hand-carved mantel by noted English artisan woodcarver Grinnling Gibbons and the other is a 1780 mantel surrounded by the famous English architect and artisan, Robert Adam. The main floor of the 18th-century wing contains a spacious living room, dining room, original kitchen, and larger kitchen, pantry, two powder rooms, and a stunning sunroom connecting to a terrace along the rear of the house overlooking the Choptank River. Part of this wing was the final addition to the original home. The second floor of the 19th-century wing contains two bedrooms over the two parlors below with fireplaces and walk-in closets and two baths. The 18th-century wing and later addition contain an artist’s studio with cabinetry and sink that has a myriad uses– TV room, arts and crafts room. The primary suite is located at the rear corner of this wing. It has a fireplace flanked by single windows and another window on the rear wall for panoramic views of the mature landscape and the Choptank River. Two baths complete the suite, with one bath off a hall for access from the art studio. Two stairs access the attic level; one in the 18th-century wing leads to two bedrooms and one bath. The main stair in the 19th-century wing leads to a large game room and another cozy bedroom ensuite. The revised offering of The Wilderness, providing 234 acres comprised of 5 recorded parcels with over 3,000 feet of shoreline is a remarkable opportunity to witness life on the Shore.

27295 Southside Island Creek Rd, Trappe
$950,000
1000050037 MLS
Excellent Traffic Exposure - Frontage on Choptank River - Potential Winter Boat Storage - All Earnest Money Deposits (EMD) shall be held in escrow by listing broker.

1700 Ocean Gateway, Trappe