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Nestled on a picturesque country setting, this exceptional and thoughtfully designed estate is perfect for both everyday living and entertaining. Featureing a beautifully appointed four-bedroom main residence, a private guest apartment, an inviting outdoor living area, and a spacious pole barn. The heart of the home is the stunning gourmet kitchen, complete with high-end appliances including a Viking range, a wine refrigerator, and an expansive center island with seating. The open design creates a seamless flow into the adjoining living and dining spaces, making it ideal for gatherings of any size. The luxurious main-level primary suite provides a peaceful retreat, while the covered front porch and screened porch offer the perfect places to enjoy the surrounding landscape throughout the seasons.Step outside to discover an extraordinary outdoor oasis featuring an in-ground pool, a charming pool house, and a covered outdoor kitchen and living area designed for effortless entertaining. Whether hosting family and friends or enjoying a quiet evening at home, the outdoor amenities create an unmatched resort-like atmosphere. Guests will appreciate the detached one-bedroom apartment, complete with a kitchenette and a cozy wood-burning stove, providing both privacy and comfort. A large pole barn offers abundant storage space and endless possibilities for hobbies, equipment, or workshop use. New GAF roof on main house, pole barn and garage has a fully transferable 50-year warranty on materials and a 30 year workmanship warranty. Offering an exceptional combination of elegance, functionality, and timeless appeal, this remarkable property presents a rare opportunity to enjoy the very best of Eastern Shore living.

5 Beds ⋅ 6 Baths

Nestled on a picturesque country setting, this exceptional and thoughtfully designed estate is perfect for both everyday living and entertaining. Featureing a beautifully appointed four-bedroom main residence, a private guest apartment, an inviting outdoor living area, and a spacious pole barn. The heart of the home is the stunning gourmet kitchen, complete with high-end appliances including a Viking range, a wine refrigerator, and an expansive center island with seating. The open design creates a seamless flow into the adjoining living and dining spaces, making it ideal for gatherings of any size. The luxurious main-level primary suite provides a peaceful retreat, while the covered front porch and screened porch offer the perfect places to enjoy the surrounding landscape throughout the seasons.Step outside to discover an extraordinary outdoor oasis featuring an in-ground pool, a charming pool house, and a covered outdoor kitchen and living area designed for effortless entertaining. Whether hosting family and friends or enjoying a quiet evening at home, the outdoor amenities create an unmatched resort-like atmosphere. Guests will appreciate the detached one-bedroom apartment, complete with a kitchenette and a cozy wood-burning stove, providing both privacy and comfort. A large pole barn offers abundant storage space and endless possibilities for hobbies, equipment, or workshop use. New GAF roof on main house, pole barn and garage has a fully transferable 50-year warranty on materials and a 30 year workmanship warranty. Offering an exceptional combination of elegance, functionality, and timeless appeal, this remarkable property presents a rare opportunity to enjoy the very best of Eastern Shore living.

4401 Grove Rd, Trappe

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Meredith Fine Properties.

$1,600,000

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.

3 Beds ⋅ 2 Baths

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

Listing courtesy of LPT Realty, LLC. Contact:

Selling Office: Long & Foster Real Estate, Inc..

$1,600,000

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

Listing courtesy of LPT Realty, LLC. Contact:

Selling Office: Long & Foster Real Estate, Inc..

$464,000

This unique and well maintained home is located in the heart of Trappe and has a lot to offer. Main home features formal living and dining areas, family room, kitchen, laundry, 1.5 baths on the first floor. 2nd floor has 3 spacious bedrooms and bath. Wood floors throughout home and all windows are currently being replaced (Dec. 2025). Warm radiator oil heat and mini-split units heat and cool the home. In the rear of the lot there is a large 2 car garage with 2nd floor studio apartment/office with kitchenette and bath, heat pump and wood flooring. The .54 acre lot is lavishly landscaped with 2 garden sheds, gazebo and patio area. Home also has a screened porch.

3 Beds ⋅ 3 Baths

This unique and well maintained home is located in the heart of Trappe and has a lot to offer. Main home features formal living and dining areas, family room, kitchen, laundry, 1.5 baths on the first floor. 2nd floor has 3 spacious bedrooms and bath. Wood floors throughout home and all windows are currently being replaced (Dec. 2025). Warm radiator oil heat and mini-split units heat and cool the home. In the rear of the lot there is a large 2 car garage with 2nd floor studio apartment/office with kitchenette and bath, heat pump and wood flooring. The .54 acre lot is lavishly landscaped with 2 garden sheds, gazebo and patio area. Home also has a screened porch.

3962 Main St, Trappe

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

$1,250,000

Prime 82.54± Acre Eastern Shore Farm With Tillable Ground And Hunting This 82.54-acre property in Talbot County, Maryland, offers a highly desirable opportunity to own productive Eastern Shore farmland with strong agricultural value, recreational appeal, and future homesite potential. Situated in a well-regarded farming region, this tract offers a balanced combination of income-producing capability, land investment potential, and outdoor enjoyment. The property is zoned agricultural, allowing continued row-crop production, long-term land ownership, and flexibility for future use. A large portion of the acreage is tillable, supported by soils consisting primarily of Hambrook Sassafras complex and Ingleside sandy loam. These soil types are well known throughout the region for their productivity and drainage, making the farm suitable for consistent agricultural operations. In addition to its farming attributes, the property includes a smaller wooded section that enhances privacy, natural diversity, and wildlife habitat. This wooded section also includes a designated forest conservation area, as shown on the recorded plat. This area represents only a small portion of the overall property and contributes to long-term environmental stewardship while maintaining the farms overall usability and value. Portions of the property were previously enrolled in CRP, offering the potential to further utilize income-producing opportunities on the property while continuing current agricultural practices. The property benefits from excellent access and layout, with road frontage along Bambury Road on the eastern boundary and Kates Point Road along the northern boundary. This dual frontage provides convenient entry points and supports efficient movement for farming operations. A drainage and utility easement is present on the property, typical for farms in the area near county roads, and does not detract from its overall usability. From a recreational standpoint, this property offers exceptional hunting potential. The combination of productive tillable ground, natural edge habitat, and surrounding agricultural landscape creates an ideal environment for attracting and holding whitetail deer and migratory geese. The property has a strong history of producing quality whitetail deer, with the area known for harvesting mature bucks. The layout supports multiple stand and blind locations, allowing for effective setups across different wind directions and seasons. The property also offers strong potential for a future homesite, making it an excellent option for those looking to build a private residence, farmhouse, or retreat surrounded by productive farmland and natural beauty. This blend of usability, privacy, and location creates an appealing setting for both investment and lifestyle buyers. For buyers seeking expansion, this tract is also available in combination with the adjacent 90-acre home farm, creating the potential for a larger, contiguous farming operation with additional improvements. This Talbot County property offers a rare combination of productive farmland, recreational value, and long-term potential in one of Marylands most sought-after rural regions. 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-B Windy Hill Rd, Trappe

Listing courtesy of LPT Realty, LLC. Contact:

Selling Office: Meredith Fine Properties.

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