Trappe Homes with Pool

Trappe Homes with Pool

Welcome to Trappe, Maryland – a charming town that beautifully blends small-town charm with modern conveniences. Nestled in the heart of Talbot County, Trappe offers a serene escape from the hustle and bustle of city life, while still being conveniently located just a short drive from the vibrant towns of Easton and St. Michaels. With its picturesque landscapes, rich history, and friendly community, Trappe is the perfect place to call home.

One of the standout features of Trappe is its stunning selection of homes that come with pools, providing the ultimate backyard oasis for relaxation and entertainment. Imagine spending warm summer days lounging by your private pool, hosting barbecues with friends, or enjoying peaceful evenings under the stars. These homes offer not just a place to live, but a lifestyle filled with leisure and enjoyment.

The real estate market in Trappe is diverse, featuring everything from charming historic homes to modern estates. Each property is unique, allowing you to find the perfect fit for your lifestyle. Many of these homes with pools are situated on spacious lots, providing ample outdoor space for gardening, play, or simply unwinding in nature.

In addition to its beautiful homes, Trappe boasts a close-knit community with excellent schools, local shops, and recreational activities. Whether you’re exploring the scenic trails, indulging in local cuisine, or participating in community events, you’ll find that Trappe offers a quality of life that is hard to beat.

Discover the beauty and tranquility of Trappe, where your dream home with a pool awaits!

Newest Trappe Homes with Pool

$2,895,000
4 Beds 5 Baths
Public and Broker/Agent open house Thursday 8/6 11am-1pm. 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

$599,999
4 Beds 4 Baths
Schedule your tour today. Welcome to this solid stone rancher in desired, Perkiomen Valley School District, South Elementary, with many custom features! You enter into the formal living room with hardwood floors that continue throughout the first floor. Following into the kitchen you will see there is plenty of cooking room and two refrigerators to fit all your groceries. Leading into the sundrenched and airy family room, this addition has zone heated flooring. The Master Bedroom suite, and the master bathroom also have this zone heated flooring. Total of 5 different heating zones to adjust through out the home. Additional amenities to the master bedroom are cathedral ceilings, walk in closet, and whirlpool tub, you will see it's perfect for relaxing after a long day. Heading over to the additional bedrooms, you have a princess suite with it's own full bathroom, two additional bedrooms ample in size, and a third full bathroom in the hallway. Central vacuum system with wall ports through out home. The basement has been finished into a perfect entertainment space with a built in wet bar, 4th full bathroom, laundry area, and extra large room for ready to be turned into a workshop, gym, home office, or additional bedroom. Don't forget about the pool with enormous wood deck and fully fenced back yard. owner is licensed PA real estate agent, listing agent is related to seller

258 W 5th Ave, Trappe

Listing courtesy of RE/MAX Ready. Contact: (610) 828-6300

$5,995,000
6 Beds 6 Baths
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

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 770-9255

$492,440
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 and presents a rare opportunity to personalize your interior selections while construction is underway. Choose your own cabinetry, countertops, and flooring and create a home that truly reflects your style. The open main level features volume ceilings in the great room, creating an airy and inviting living space. 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

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