Trappe MD Homes For Sale

First Time Offered! This meticulously maintained, custom-quality stick-built Cape Cod is beautifully situated in an idyllic country setting. Thoughtfully designed with three bedrooms and two-and-a-half baths, the home offers generous, light-filled living spaces, recessed lighting throughout and high-speed internet. A dramatic vaulted ceiling enhances the living room, while the gourmet kitchen, formal dining room and adjoining sunroom create an inviting setting for everyday living and entertaining. An oversized recreation room provides exceptional flexibility for gatherings, hobbies or a media room. The spacious primary suite features a vaulted ceiling, direct access to the hot tub and a spa-like bath with dual vanities, a walk-in shower and soaking tub. Two additional bedrooms and a full bath provide comfortable accommodations for family and guests. Significant improvements include a new roof and gutters in 2025, numerous replacement Andersen windows and updated porch windows with retractable screens. Outside, the private grounds are designed for relaxation and entertaining with an in-ground pool, hot tub and generous outdoor living space surrounded by peaceful country views. A substantial 30-by-40-foot outbuilding offers exceptional space for a workshop, storage, vehicles or recreational equipment. Lovingly cared for by its original owners, this special property combines quality construction, thoughtful updates, privacy and relaxed Eastern Shore living.

30108 Deep Branch Ln, Trappe

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344

$879,000

4 Beds ⋅ 3 Baths

An Exceptional Custom Built Choptank River Waterview Retreat. Masterfully crafted in 2021 by the owner, an experienced custom home builder, this modern farm style home is a true showcase of exceptional craftsmanship, timeless architecture, and refined luxury. Every detail was thoughtfully designed to create a residence that is both elegant and inviting, where breathtaking Choptank River views and spectacular sunset skies become part of everyday living. Offering approximately 3,000± square feet on .95± acres, this remarkable home captures panoramic water views from nearly every room. Expansive windows fill the interiors with natural light while framing the ever changing beauty of the river, creating a serene backdrop for both relaxation and entertaining. Surrounded by beautiful mature landscaping with irrigated lawn, the grounds provide a private and picturesque setting with thoughtfully designed outdoor spaces that enhance the timeless appeal of the home and create a truly tranquil retreat. Designed with lifestyles of today in mind, the open concept living spaces are ideal for gathering with family and friends. Soaring cathedral ceilings, brick fireplace, and walls of windows create a stunning great room that flows seamlessly into the dining area and gourmet kitchen. The chef inspired kitchen is the centerpiece of the home, featuring elegant quartz countertops, a striking leathered granite island, premium finishes, and a spacious entertaining bar. The thoughtful design provides the perfect setting for preparing meals, hosting guests, and enjoying conversation while taking in beautiful views of the Choptank River. The luxurious main level primary suite offers a private oasis with a spa inspired bath featuring a large custom tiled shower, relaxing soaking tub, expansive walk in closet, and conveniently placed laundry nearby. Two additional bedrooms share a beautifully appointed full bath on the main level along with custom designed private office space and mudroom that showcase exceptional storage, woodworking details, and craftsmanship throughout. The upper level provides a spacious fourth bedroom with captivating bird’s eye views of the river and generous walk in attic storage. Outdoor living is equally impressive with spaces designed for unforgettable entertaining and relaxation. While taking in river views at all times of day, enjoy morning coffee on the deck, cocktails on the patio, and prepare and indulge in meals in the beautifully appointed outdoor kitchen and bar area. After a day on the boat, unwind beneath colorful sunset skies in the refreshing outdoor shower. The backyard creates the perfect backdrop for hosting family and friends while enjoying the beauty of the Eastern Shore. The exterior of the home reflects its custom quality with classic board and batten siding, Bermuda shutters, wooden gable accents, and designer lighting. Ideally located to enjoy the best of Eastern Shore living, take your golf cart to Ferry Point Marina for boating access or pick up fresh local seafood from TL Morris Seafood before returning home to enjoy dinner with breathtaking sunset views over the Choptank River. This sanctuary is placed a short drive away from the desirable towns of Easton and Saint Michaels, where gourmet restaurants, historical sites, and boutique shopping await. Ocean beaches can be reached in just over one hour and Washington D.C. in about one and a half hours. This is more than a home, it is a thoughtfully crafted retreat designed for gathering, entertaining, and embracing the beauty of every season. A rare opportunity to own a custom residence where luxury finish, exceptional craftsmanship, and captivating water views come together to create an extraordinary lifestyle.

29629 Ferry Point Dr, Trappe

Listing courtesy of Meredith Fine Properties. Contact: 4108226272

$470,000

3 Beds ⋅ 3 Baths

Tucked away among the farmland of Talbot County, this charming Cape Cod offers a peaceful Eastern Shore setting while still being conveniently located just outside of Easton. Set on more than two acres with mature trees, established gardens, nearby ponds, and quiet winding roads, the property offers privacy and plenty of room to enjoy the outdoors. Inside, the home features three bedrooms, two full baths, and a flexible floor plan. The main level includes a living room, separate dining room, spacious kitchen with an oversized island, and a first-floor primary suite with private bath. A dedicated laundry room with half bath adds convenience, while a separate space just off the garage entry makes an ideal drop zone, mudroom, or additional storage area. Upstairs are two additional bedrooms, a full bath, and an open bonus area perfect for a playroom, home office, or second living space. Outside, established flowers gardens, Black-eyed Susans, berry bushes, and mature trees create a gardener's dream with plenty of space to make your own. Enjoy the privacy of country living with the shops, restaurants, and conveniences of Easton just a short drive away. Professional photos coming soon!

5935 Bay Acres Dr, Trappe

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

$249,990

2 Beds ⋅ 1 Baths

This charming 2-bedroom bungalow, remodeled kitchen with granite counters, large island, new floors throughout, appliances, hot water heater & HVAC. All major units have been replaced. Home offers a unique blend of classic character and modern convenience. With 1,014 sq. ft. of thoughtfully designed space. Enjoy the convenience of main floor laundry hookups, enhancing everyday living. The detached structure sits on a generous 0.17-acre lot, providing ample outdoor space for relaxation or gardening. Parking is hassle-free with a dedicated driveway. This property is perfect for those seeking a cozy home with potential for customization. Experience the charm of a historic bungalow. Don't miss the opportunity to make this your own!

4070 Hennisee Ln, Trappe

Listing courtesy of Keller Williams Realty. Contact: 3023600300

$599,990

4 Beds ⋅ 4 Baths

BUILDER OFFERING BELOW MARKET RATE FINANCING OPTIONS ON THIS QUICK MOVE IN HOME!! Don’t miss this incredible opportunity—3 Car Garage! 4 bedrooms, 3.5 baths, offering exceptional space and value for today’s lifestyle. Backing to trees for added privacy and a serene view, this home delivers both comfort and setting. The bright sunroom off the kitchen creates the perfect gathering space, while the kitchen itself shines with a farmhouse sink, white cabinetry, quartz countertops, and a gourmet stainless steel appliance package with a hood. Luxury vinyl plank flooring spans the main level. Upstairs, enjoy the convenience of a second-level laundry room with a utility sink. Located in Trappe, MD—just minutes from Easton—Lakeside at Trappe offers an amenity-rich lifestyle. Residents enjoy a pool, bathhouse with fitness room, ping pong, cornhole, playground, sports courts, and a dedicated Bark Park, with exciting future lakeside amenities to come. With easy access to Easton, Cambridge, and the surrounding Chesapeake Bay region, this community blends convenience, recreation, and value. Ask about builder incentives! Please note interior photos are similar while under construction

1953 Silver Lake Ln, Trappe

Listing courtesy of Brookfield Mid-Atlantic Brokerage, LLC. Contact: (703) 420-3322

$413,440

5 Beds ⋅ 3 Baths

The Richmond by Lennar is a popular new construction home on Maryland’s Eastern Shore, offering approximately 2,238 square feet of thoughtfully designed living space. This spacious floor plan features 5 bedrooms and 3 full bathrooms, providing plenty of room for family, guests, or a home office. The open-concept layout showcases a large kitchen and dining area, highlighted by elegant quartz countertops and ample space for entertaining. Enjoy outdoor living with a rear patio, perfect for relaxing or hosting gatherings.

1471 Lake George Ln, Trappe

Listing courtesy of Builder Solutions Realty. Contact:

$411,490

5 Beds ⋅ 3 Baths

This Richmond model features 5 bedrooms, including a convenient 1st floor bedroom, making it a great option for guests, multi generational living or a home office. This particular home includes Washer and dryer, 16x10 Paver Patio, quartz Countertops and white cabinetry. Features and amenities of the community include: outdoor community pool, bathhouse and fitness studio, multi-racquet sports courts (including tennis and pickleball), play ground, Bark Park/dog park, walking and biking trails, central community lake and gathering ares and open green spaces. Lakeside at Trappe is conveniently located just off Route 50, about 8 miles south of Easton, providing easy access to shopping, dining and the Eastern Shore beaches. The Builder is offering closing costs with the use of Lennar Mortgage and Title.

1471 Lake George Ln, Trappe

Listing courtesy of EXP Realty, LLC. Contact: 8333357433

$1,500,000

4 Beds ⋅ 3 Baths

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

31720 Ayres Dr, Trappe

Listing courtesy of Weichert, REALTORS. Contact: afitzgerald@weichertrealtors.net

$750,000

3 Beds ⋅ 4 Baths

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

Listing courtesy of Meredith Fine Properties. Contact: 4108226272

$250,000

4 Beds ⋅ 3 Baths

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! Will not pass FHA, or VA. A great fixer-upper or investment property. Cash or Conventional only! 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

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com

$2,895,000

4 Beds ⋅ 5 Baths

Enjoy a Piazza Italian Market lunch at this 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

$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

$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

$3,249,000

4 Beds ⋅ 4 Baths

Island Creek Estate — rare total privacy, deep water dockage, meaningful architecture, and superb build quality all intersect at this remarkable, truly one-of-a-kind waterfront offering. Set on approximately 6 acres of park-like grounds with 500± feet of shoreline and 6’± MLW, the property offers exceptional water access along the peaceful expanse of Island Creek. The setting is serene and private, with a gracious approach that complements the estate’s architectural presence. Impeccably built with careful attention to detail, the residence offers 4 bedrooms and 3.5 baths within a thoughtfully designed floor plan that maximizes natural light and water views. The living room, kitchen, and dining area flow comfortably together, creating a spacious central gathering area framed by expansive windows overlooking the creek and anchored by a fireplace. The kitchen is generously sized, featuring a substantial island, quality finishes, and an inviting eat-in area suited for both everyday living and entertaining. Outdoor living is equally compelling, with a screened porch overlooking the water and an in-ground pool set against sweeping creek views. The private pier provides deep water dockage, ideal for boating enthusiasts seeking immediate access to the Chesapeake Bay watershed. A finished rec room above the attached garage offers flexible use as a media room, office, or fitness space. In addition to the attached two-car garage, the property features a substantial detached multi-bay garage equipped with a hydraulic vehicle lift, air compressor, and rough-in for a future bath — an exceptional amenity for car collectors, hobbyists, or workshop space. This exceptional Island Creek estate combines craftsmanship, privacy, and premier waterfront living in a setting that is both refined and enduring.

4346 Southside Ln, Trappe

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

$329,000

3 Beds ⋅ 1 Baths

This easy one level living rancher is located in a quiet neighborhood between Easton and Cambridge on the scenic eastern shore of Maryland. There is a pond and playground within the community for residents use. You will enjoy relaxing on the rear screened in deck that overlooks a generous backyard. Appliances, window treatments, and 2 outdoor storage sheds convey with sale. This would make a wonderful starter or retirement home.

3900 Harrison Cir, Trappe

Listing courtesy of Mr. Lister Realty. Contact: (410) 486-5478

$2,300,000

4 Beds ⋅ 3 Baths

"New Scotland Farm" First time offered in decades! This special and unique offering includes 100 +/- acres of prime farm and hunting land, encompassing a spacious farmhouse and three additional income producing properties, two ponds, and deeded water access with a dock and slip on LaTrappe Creek. There is the potential for subdivision of 4 lots outside the of the critical area. (buyer to verify) This offering consists of three parcels: Parcel #1 Main House with Rental Properties 21.34 +/- acres improved by a 5BR farmhouse (which includes a separately rented apartment above the garage), two guest cottages that are income producing, and two scenic ponds, one that can be hunted year round. A newly refurbished tennis court and pavilion overlook the second pond. The main house, a Victorian style farmhouse, has a brand new roof , geothermal units and outdoor deck. There is a historic section of the home and an addition built in the 1990’s. The main house also features a separate apartment above the garage for income potential, or ideal for a caretaker. Beautiful setting with mature trees, complete privacy and lovely vistas from several vantage points. Parcel #2 Land 83+/- acres (65 in till) in agriculture. Farm tenant in place. Community Boat Slip (25% interest) 1.424 +/- acres Deeded boat slip and water access on LaTrappe Creek via shared pier with 3 other homes. This is a unique property with an endless potential of uses, from a hunting retreat, private getaway, investment or combination of all.

28923 Island Creek Rd, Trappe

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

$2,300,000

4 Beds ⋅ 3 Baths

"New Scotland Farm" First time offered in decades! This special and unique offering includes 100 +/- acres of prime farm and hunting land, encompassing a spacious farmhouse and three additional income producing properties, two ponds, and deeded water access with a dock and slip on LaTrappe Creek. There is the potential for subdivision of 4 lots outside the of the critical area. (buyer to verify) This offering consists of three parcels: Parcel #1 Main House with Rental Properties 21.34 +/- acres improved by a 5BR farmhouse (which includes a separately rented apartment above the garage), two guest cottages that are income producing, and two scenic ponds, one that can be hunted year round. A newly refurbished tennis court and pavilion overlook the second pond. The main house, a Victorian style farmhouse, has a brand new roof , geothermal units and outdoor deck. There is a historic section of the home and an addition built in the 1990’s. The main house also features a separate apartment above the garage for income potential, or ideal for a caretaker. Beautiful setting with mature trees, complete privacy and lovely vistas from several vantage points. Parcel #2 Land 83+/- acres (65 in till) in agriculture. Farm tenant in place. Community Boat Slip (25% interest) 1.424 +/- acres Deeded boat slip and water access on LaTrappe Creek via shared pier with 3 other homes. This is a unique property with an endless potential of uses, from a hunting retreat, private getaway, investment or combination of all.

28923 Island Creek Rd, Trappe

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

$511,550

4 Beds ⋅ 2 Baths

Beautiful home offering 4 generous bedrooms with 2 baths featuring new commercial grade LVP flooring throughout the main floor, custom kitchen cabinets with pantry, automatic under counter lighting, slow close cabinets, luxury tile in bathroom and laundry room, all new stainless steel appliances, custom walk-in shower with bench, new vanity, and multiple shower heads. Second bathroom has been renovated completely to feature a deep soaking tub, with new upgraded hot water tank to soak for hours. Additionally all new upgraded HVAC ductwork and with an additional dampening system which allows your garage to have AC/heat. Freshly painted interior tops it off. Outside there is a fenced yard with an extended patio with a 10 x 13 hard topped gazebo, raised garden beds, fire pit, and a large shed to give you the perfect outdoor oasis with outdoor lighting so the celebrations can continue into the night.This is a must see home on a quiet street in a well desired school district. Square footage is larger than tax record and Seller to find home of choice

3853 Rumsey Dr, Trappe

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

$1,550,000

Trappe Business Park -38± Acres in Trappe, Maryland. Exceptional industrial development opportunity in the heart of Talbot County. Trappe Business Park consists of approximately 38± acres with a preliminary plat approved by the Town of Trappe for twelve (12) industrial building lots. Lot sizes range from approximately 1.5 acres up to 11.8 acres, offering flexibility for a variety of industrial, flex, warehouse, or service oriented uses. Strategically positioned just 1,500 feet from U.S. Route 50, the property provides excellent regional access along the primary corridor connecting the Eastern Shore to Annapolis, Baltimore, and the Delaware beaches. The site is also located less than half a mile from the rapidly expanding residential and mixed use community of Lakeside at Trappe, creating built in proximity to a growing workforce and customer base. Planned infrastructure includes municipal water and sewer service, enhancing development efficiency and long term value. With approved layout, strong access, and nearby growth, Trappe Business Park presents a rare opportunity to establish or expand your footprint in one of the Eastern Shore’s most active growth corridors. Property can be purchased as a whole or by individual lot sales. Ideal for investors, developers, or end users seeking shovel ready potential in a strategic location.

4502 Old Trappe Rd, Trappe

Listing courtesy of Meredith Fine Properties. Contact: 4108226272

$175,000

Real Estate not included A full-featured screen printing and embroidery business is available for sale, including all essential equipment, accessories, and an established customer base, making it a turnkey opportunity for entrepreneurs. Business Overview This type of business typically combines screen printing and embroidery services, catering to both individuals and organizations seeking branded apparel, uniforms, promotional items, and custom merchandise The business can operate full or part-time , offering personalized services ranging from monogramming and logo embroidery to multicolor screen printing for shirts, hoodies, hats, and even towels or canvas products. Embroidery is ideal for textured and thicker fabrics, while screen printing works best on smooth fabrics like cotton or blends. Equipment Included Equipment for sale encompasses everything needed to produce high-quality customized garments: Embroidery machines: Multi-head industrial Brother machines capable of handling multiple projects efficiently. 1. Screen printing presses: units provide precise, high-volume production 2. Drying and curing systems: Conveyor dryers, flash units, and heat presses for curing inks Brother embroidery machines are renowned for combining durability, advanced technology, and ease of use, offering a wide range of models suitable for beginners to professional crafters. General Features Brother embroidery machines are designed to handle various projects, from personalizing apparel to home décor embellishments. Key features include: Built-in designs and fonts: Most Brother machines come with hundreds of built-in embroidery designs, frame patterns, and lettering fonts, allowing monogramming and creative projects.

4929 Ocean Gtwy, Trappe

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

$2,500,000

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

Listing courtesy of VYBE Realty. Contact: 4102204648

$2,500,000

5 Beds ⋅ 1 Baths

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

Listing courtesy of VYBE Realty. Contact: 4102204648

$5,500,000

This 7.6 Acre Premier Commercial Parcel offers exceptional versatility in one of the Eastern Shore's most active growth corridors. Located along Rt. 50 between Easton and Cambridge, Maryland, the property features approximately 932 linear feet of frontage on a heavily traveled roadway, connecting the Chesapeake Bay Bridge and Ocean City. The site benefits from excellent Ingress and Egress, strong traffic counts, and outstanding visibility. The owner is willing to subdivide into smaller parcels for a qualified buyer, allowing flexibility for phased development, pad sites, or mixed-use configurations. Positioned directly in front of and adjacent to a 2,500 home development currently under construction, the property is surrounded by both established neighborhoods and rapidly emerging residential density. This location provides built-in demand and supports a wide range of high-performing commercial and service -oriented uses. Its current use is a gas station/convenience store that has thrived for many years. With scale, frontage, and development flexibility, this property presents a rare opportunity for investors and devlopers seeking long-term growth and multiple exit strategies along Route 50.

4123 Ocean Gateway, Trappe

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$509,990

3 Beds ⋅ 2 Baths

BUILDER OFFERING BELOW MARKET RATE FINANCING OPTIONS ON THIS MOVE IN READY HOME!! Ideally located in a prime cul-de-sac, this main level living home showcases a sophisticated interior with artisan trim and impressive 10-foot ceilings throughout. The welcoming covered entry leads you to the heart of the home: a spacious family room open to a chef-inspired kitchen and a comfortable dining area. The kitchen is a highlight, featuring a substantial island, abundant white cabinets, Carrara Morro quartz countertops, a gourmet stainless steel appliance package with range hood, and a large walk-in pantry. Extend your living space to the rear screened porch, accessible from the family room and dining room. A dedicated study offers a quiet sanctuary for work or hobbies. The primary suite offers a private retreat with dual walk-in closets and a deluxe primary en suite bathroom featuring a soaking tub. The opposite wing houses two secondary bedrooms and a full bathroom. A well-appointed laundry room with a sink, conveniently located off the two-car garage, also functions as a practical mudroom. Located in Lakeside at Trappe, a vibrant lakeside community with a plethora of amenities and ideally located on Maryland's Eastern Shore. Lakeside at Trappe is a private retreat to live, work, and play all in one place. Community currently offers a pool, bathhouse with fitness room, ping pong, corn hole and Bark park, playground and racquet sports courts. An immersive lakeside experience also in the works! Ask about special fixed rate financing and closing costs!

1549 Lake Tahoe Dr, Trappe

Listing courtesy of Brookfield Mid-Atlantic Brokerage, LLC. Contact: (703) 420-3322

$55,000

This parcel is located between Trappe and Easton is almost 3/4 of an acre. A great piece of land in a sought-after Talbot County with buildable potential. The property is currently undergoing evaluation for SDA/perc. Convenient to shopping, dining, and local amenities. Enjoy all that the Eastern Shore has to offer!

6367 Ocean Gtwy, Trappe

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$40,000

Nearly one acre of land ideally located along Ocean Gateway (Route 50) between Trappe and Easton, Maryland. This property offers excellent visibility and convenient access to major routes. Situated in a central location on the Eastern Shore, you are just minutes from shopping, dining, and local amenities. Offered at $40,000, this is an affordable chance to secure land in a highly traveled corridor. Perc and water tables may need to be re-tested for the SDA approved in 2007.

Ocean Gateway, Trappe

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$11,000,000

4 Beds ⋅ 5 Baths

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

29245 Howell Point Rd, Trappe

Listing courtesy of Holiday Real Estate. Contact: 4105247700

$49,900

1.28 Acres of vacant land on Route 50 Eastbound between Almshouse Road and Sanderstown Road. Undergrowth and small trees have been cleared and woodchips spread for easy access. Property does not have a SDA and therefore is not a buildable lot at this time. A 3 bedroom SDA application has been made for this 2026 wet season testing. Property will also need a driveway connection to Route 50 (an approved SDA will block access from the existing shared driveway). A variance from the 150’ state highway setback will need to be obtained also. The site plan has an area designated as non-tidal wetlands. MDE has indicated that they will allow an up to 5,000 sq ft encroachment into that area for a larger building footprint. PLEASE DO NOT drive back onto the neighbor property to the back left.

Ocean Gtwy, Trappe

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$335,000

6 Beds ⋅ 3 Baths

Historic Farmhouse with Significant Value-Add Potential Built in 1919 and offering approximately 3,448 square feet, this stately farmhouse sits on a .44-acre lot and presents a rare opportunity for investors or renovation enthusiasts to restore a historic property with substantial upside. The home features many original architectural elements, including hardwood floors, crown molding, multiple fireplaces, wood pocket doors, and a grand staircase that highlight the craftsmanship of the era. The spacious main level includes two large sitting rooms, a formal dining room with floor-to-ceiling windows overlooking the wraparound porch, and a large kitchen with walk-in pantry. Additional features on this floor include a laundry area, half bath, and a secondary staircase leading to the upper level. Upstairs you’ll find five bedrooms and two full bathrooms, along with multiple linen closets and a long hallway lined with original wood doors. The third floor offers a sixth bedroom and an additional flex space, providing even more potential for added living area. With 3 levels of living space and a large footprint, this property offers an excellent canvas for renovation or restoration. Homes in the area that have been updated command significantly higher values, making this a compelling value-add investment opportunity. Property is being sold strictly as-is.

4096 Main St, Trappe

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545

$485,000

4 Beds ⋅ 3 Baths

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

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415

$489,990

3 Beds ⋅ 2 Baths

BUILDER OFFERING BELOW MARKET RATE FINANCING OPTIONS ON THIS MOVE IN READY HOME!! Brand New Single Level Matisse is now Ready for Move In at Lakeside at Trappe! This home is highlighted by impressive 10-foot ceilings throughout. The kitchen is designed with white and grey cabinets, Carrara Morro quartz countertops, a gourmet stainless steel appliance package and opens to the family room and dining area which leads to the rear screened porch. The primary suite offers a private retreat with dual walk-in closets and a deluxe primary en suite bathroom featuring a soaking tub. The opposite wing houses two secondary bedrooms and a full bathroom. A well-appointed laundry room with a sink, conveniently located off the two-car garage, also functions as a practical mudroom. Located in Lakeside at Trappe, a vibrant lakeside community with a plethora of amenities and ideally located on Maryland's Eastern Shore. Lakeside at Trappe is a private retreat to live, work, and play all in one place. Community currently offers a pool, bathhouse with fitness room, ping pong, corn hole, Bark park, playground and racquet sports courts . An immersive lakeside experience also in the works! Ask about special financing opportunities and closing costs!

1553 Lake Tahoe Dr, Trappe

Listing courtesy of Brookfield Mid-Atlantic Brokerage, LLC. Contact: (703) 420-3322

$334,290

3 Beds ⋅ 3 Baths

Large 3 bed Townhouse 2,254 sq ft - July Delivery! Open plan kitchen, Stainless steel appliances. Photos are for illustration purposes. Agents must accompany buyer during first visit to the community.

1217 Loch Ness Ln, Trappe

Listing courtesy of Builder Solutions Realty. Contact:

$8,750,000

6 Beds ⋅ 6 Baths

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

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

$2,490,000

Prime hunting farm on the Choptank River in Talbot County. 49+ acres, duck, geese, deer, 500'+ of waterfrontage, 3.5-4' MLW, pond, sandy beach, beautiful, broad, westerly views.

Chloras Point Rd, Trappe

Listing courtesy of Meredith Fine Properties. Contact: 4108226272

$950,000

Well situated 10.5 commercial acres on Ocean Gateway just north of The Choptank River Bridge. Waiting for Maryland and Talbot County approval and funding of private sewage treatment plant. Waterfront location

1700 Ocean Gateway, Trappe

Listing courtesy of Latshaw Commerical. Contact:

$950,000

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

Listing courtesy of Latshaw Commerical. Contact: