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$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
$525,000
3 Beds ⋅ 3 Baths
Welcome to 29796 Lyons Drive, where comfortable elegance, easy living, and the peaceful beauty of Maryland’s Eastern Shore come together. Located in a desirable 55+ community, this beautifully maintained Merion Model offers an inviting floor plan, impressive architectural details, and tranquil surroundings. Adding even more peace of mind, the home features a roof that is only 2 years old. From the moment you step inside, you’ll appreciate the home’s attention to detail, including soaring ceilings and an elegant tray ceiling in the dining room. The warm and welcoming family room is centered around a gas fireplace, creating the perfect setting for relaxing evenings or gathering with family and friends. Designed with convenient main-level living in mind, the spacious primary suite is located on the first floor and is enhanced by a beautiful tray ceiling. The private primary bath features a walk-in shower and soaking tub, creating your own relaxing retreat at the end of the day. At the heart of the home is a spectacular kitchen featuring granite countertops and beautiful 42-inch maple cabinetry, offering plenty of workspace and storage for everyday living and entertaining. The additional sunroom may quickly become one of your favorite places in the home. Enjoy your morning coffee while looking out over the stone patio and surrounding trees, where wild turkeys and deer may be among your morning visitors. Need a little extra space? A finished room above the garage with both heat and air conditioning provides wonderful flexibility. Create a home office, hobby or craft room, exercise space, media room, or comfortable retreat—the possibilities are yours. Whether you’re ready to simplify your lifestyle, enjoy the benefits of a welcoming 55+ community, or simply find a beautiful home where you can relax and enjoy everything the Eastern Shore has to offer, 29796 Lyons Drive is more than a home—it’s a destination.

29796 Lyons Dr, Easton

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

$850,000
4 Beds ⋅ 4 Baths
BUCKLE UP because this is a lot of house! This large, beautiful 4-bedroom, 3½-bath home is located in the sought-after Preserve at Wye Mills. The gourmet kitchen features a huge island, granite countertops, stainless steel appliances, newer refrigerator, gas cooktop, double wall ovens, walk-in pantry and more. The formal dining room is accented with chair rail and crown molding and includes a convenient butler’s pantry. Both a living room and family room are located on the main level, with the family room featuring a gas fireplace and custom built-in shelving, including space for a large-screen TV. A spacious home office completes the main-level living space. Stylish LVP flooring, installed in 2022, extends throughout the main level, upper hallway and primary bedroom. Two staircases provide access to the upper level. The spacious primary bedroom offers two huge walk-in closets and a large en-suite bath with soaking tub, walk-in shower and two vanities. An additional bonus room provides even more flexible living space upstairs. Upscale custom plantation shutters are featured throughout the home, along with custom Closet America closet systems in all four bedrooms, the walk-in pantry and main-level hall closet. Custom shiplap accents several main-level walls, complemented by updated light fixtures, recessed lighting and hardware throughout. The main-level half bath has been remodeled, as has the Jack-and-Jill full bath with an updated vanity, lighting and flooring. An updated mudroom is conveniently located just off the kitchen. The well-insulated basement offers an incredible amount of storage space and includes a new front loading washer and dryer, a utility sink, 3-piece bath rough-in, two hopper windows, a large egress window and gas furnace with A/C serving the main level. The upper-level HVAC system was replaced in 2022 with a 3-ton, 18-SEER, 2-stage heat pump system with 10kW backup heat. Step outside to your own private backyard retreat. A huge, maintenance-free composite deck sits just off the kitchen with three stairways leading into the beautiful backyard. The fenced and custom-built approx.18’x 40’ saltwater pool features deck jets, lighting, booster pump, swim-out, steps and ladder, all surrounded by a large pool deck. A newer shed with two lofts provides additional outdoor storage. The lovely one-acre, professionally landscaped yard features an aluminum fence installed in 2022 along the sides and rear of the property. Enjoy exceptional privacy with the home backing to protected wooded sanctuary land that cannot be developed plus a tree-lined side yard providing additional separation from neighboring homes. With the pool, expansive deck, basketball court, beautiful landscaping and wooded backdrop, the backyard truly feels like a private retreat—perfect for cookouts, family activities, pets, entertaining or simply relaxing and enjoying the peaceful surroundings. The large 2-car garage features two insulated Armin garage doors installed in 2022 with Wi-Fi capability, along with a spacious paved driveway. Beautiful stacked stone, plantings, a loose-flagstone front walkway and established gardens along the front and sides enhance the home's curb appeal. Enjoy walking, biking and an abundance of local wildlife, all while remaining incredibly convenient to surrounding areas. A true commuter's delight, the home is just minutes from major routes including Route 50 and Route 404. Enjoy the best of both worlds—head west toward the Bay Bridge and Annapolis or east toward Easton and Ocean City. Shopping, restaurants, social activities, boating and water recreation, schools, hospitals and much more are all within easy reach. This property truly is a must-see! ACTIVE DATE is August 27 and schedule is now open to start booking showings for August 27 and after.

13351 Quiet Hollow Ct, Wye Mills

Listing courtesy of Blackwell Real Estate, LLC. Contact: 4432214120
$599,000
3 Beds ⋅ 3 Baths
This beautifully maintained 3-bedroom, 3-bathroom home is special the second you pull into the driveway. Situated on nearly an acre in a private and peaceful setting. When you enter the front door, you will be drawn to the large screen porch ion the rear of the home and you are also greeted by a generous living room with two fireplaces. The kitchen is large and functional with plenty of space for a large table with an office/den directly off the kitchen. Upstairs you will find 3 ensuite bedrooms with a stunning primary with a beautiful walk in shower. The outside space is stunning with a large screen porch and separate patio to enjoy the very private and parklike back yard. Other features include a conditioned crawlspace, tankless hot water heater and high speed internet provided by Easton Utilities. The ferry to Oxford, and public boat ramp are right down the road and this area is renowned for its biking and beauty. Being 10 minutes from Easton and Saint Michaels this is the ideal setting to enjoy the peaceful Eastern Shore with easy proximity to all intown amenities. 

6280 Bellevue Rd, Royal Oak

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$399,000
4 Beds ⋅ 2 Baths
Opportunity awaits! This 4-bedroom, 2-bathroom, two-level home offers a functional layout and plenty of potential for its next owner. The main level features beautiful hardwood floors, a galley kitchen, a separate dining room, and comfortable living spaces. Outside, you'll find a spacious yard with a storage shed, providing plenty of room for outdoor activities, gardening, or future improvements. This home is in need of some TLC and is priced accordingly, making it an excellent opportunity for investors, renovators, or buyers looking to add their own personal touches and build equity. With great bones and endless possibilities, this property is ready to be transformed into something special.

214 Madison Ave, Saint Michaels

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$430,000
3 Beds ⋅ 2 Baths
Welcome to Peach Lane. This home shows true pride of ownership in sought-after Fike's Orchard in Talbot County, located in the Chapel School District. Situated on over an acre, this property features mature landscaping, an established vegetable garden, and a welcoming front porch with views overlooking the original farm and orchard. A large 16x20 freshly painted back deck opens to the spacious yard and garden, creating a great setting for relaxing or entertaining. The asphalt driveway adds convenience, while inside, the family room and kitchen boast cathedral ceilings, hardwood and tile flooring, and carpeted bedrooms for comfort. This home also offers peace of mind, with the roof, HVAC, and shed roof all replaced within the last 7 years, plus a generator panel for added preparedness during outages for the well pump, kitchen, TV, sump pump, and freezer. Professional Photos will be added.

12690 Peach Ln, Cordova

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

$2,195,000
3 Beds ⋅ 3 Baths
Set on 3.3 private acres in the established community of Travelers Rest, this beautifully restored brick residence enjoys sweeping views of the Tred Avon River from nearly every room. Thoughtfully designed for one-level living, the home combines classic architectural character with extensive updates by the current owners and a floor plan that is both comfortable and highly functional. The interior has been carefully updated while retaining the character of the original home. Improvements include beautiful hardwood flooring, a renovated kitchen, new HVAC system, Rinnai tankless water heater, new roof (2017), new deck, and numerous additional enhancements. A complete list of improvements is available from the listing agent. The three-bedroom, three-bath residence includes a spacious waterside primary suite with a generous ensuite bath, ample closet space, and additional storage. Two additional bedrooms share a full bath and are privately positioned for family or guests. The main living spaces take full advantage of the river setting. The generously proportioned living room features a wood-burning fireplace framed by custom built-in bookshelves, while the formal dining room provides a gracious setting for entertaining. The renovated kitchen features a large center island and premium appliances and opens directly to the family room, where a wood stove, breakfast area, and wall of built-in bookshelves create a comfortable gathering space. An adjoining bonus room offers exceptional flexibility and could serve as a walk-in butler’s pantry, hobby or craft room. The enclosed sunroom, with its attached full bath, is a particularly appealing space from which to enjoy the expansive water views. An oversized attached two-car garage provides convenient access to extensive attic storage that runs the full length of the house. A detached climate-controlled studio adds valuable additional space for an art studio, home office, workshop, or other uses. Outside, the property is equally well appointed. A gunite pool, added in 2020, is surrounded by extensive hardscape and fencing, offering a private setting for outdoor enjoyment. The new dock, completed in 2024, includes two slips, a floating dock, and approximately 6'MLW, providing excellent access to the Tred Avon River for boating and fishing. With its coveted location, private acreage, substantial improvements, exceptional water access, and panoramic Tred Avon River views, this is a distinctive Eastern Shore waterfront property that offers both privacy and a relaxed, livable setting.

27476 Travelers Rest Ct, Easton

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344
$510,000
2 Beds ⋅ 4 Baths
Duplex centrally located in downtown Easton. Great opportunity to own investment property or convert into single family. Updates include: New architectural roof (2026) and two new natural gas heating systems installed (2026). Home features hardwood flooring throughout, replacement vinyl windows, and is certified lead free (2022). Both sides are currently leased.

423 S Washington St, Easton

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545
$1,399,000
3 Beds ⋅ 3 Baths
This beautiful historic house is located in the heart of Saint Michaels Historic District, within walking distance of waterfront parks, the harbor, shops, restaurants, the Maritime Museum, public boat ramp & more. Known as the "Keithley House, " the original dwelling was built in 1786, followed by additions believed to be added in the 1860-1870 time span. This home is beautifully updated while managing to keep & restore much of the original valued features, lending to its incredible charm & comfort. Extensive trim, exposed beams, hand huned wood, 4 fireplaces (3 wood burning, 1 electric), antique fixtures, heart pine floors & more. In addition to a lovely home, the lot is one of the larger ones in the area, at a higher elevation with beautiful landscaping, just redone, w/ gardens, fruit trees, patios, antique productive grape arbor, large shed, paths, fencing & rear gate, forming a lovely backyard oasis. Off street parking for 3 vehicles, lined w/ knock out roses & pencil Hollies. This lot offers the possibility to add onto the dwelling or a building a separate ADU or guest quarters. With many recent upgrades, this is a must see! ACCESS BY APPT ONLY, surveillance cameras.

104 Mulberry St, Saint Michaels

Listing courtesy of RE/MAX One. Contact: 4102244400
$4,000,000
4 Beds ⋅ 6 Baths
A masterpiece of Eastern Shore living, this Tidewater colonial estate is set against sweeping, panoramic views where the Choptank River, Chesapeake Bay, and three creeks converge. Showcasing breathtaking sunsets, the private oasis features a waterside pool, a main floor primary suite built in 2023, rich hardwood floors, and a detached 3-car garage. Tucked away in the desirable Ferry Neck enclave of Royal Oak, this estate offers the ultimate waterfront lifestyle. As you approach via tree-lined W. Ferry Neck Road, you enter "Tranquility" and are greeted by a circular driveway, mature landscaping, and a profound sense of privacy. Designed for classic Eastern Shore comfort, " Tranquility" offers impressive water perspectives from every room. The Main Level features gleaming hardwood floors, formal living room and dining room, gourmet kitchen with walk-in pantry, screened porch, sunroom, two wood-burning fireplaces, and two convenient powder rooms. The spectacular first-floor primary suite offers an exceptional private sanctuary. The Second Level boasts three well-appointed, ensuite bedrooms, ensuring privacy and comfort for family and guests. Structural Updates: The home also features a brand-new roof installed in 2023. Beyond the main residence, the 3-car detached garage ideal for car enthusiasts has an upper level that presently serves as an office and a substantial storage room. "Tranquility" truly provides the best of both worlds. For just under three acres, the property's privacy is unmatched. The endless water views , the close proximity to the sandy bottom shore, the pier with water, electric, and boat lift, all contribute to the perfect retreat. Furthermore, the convenience to Oxford by boat or the Bellevue Ferry, as well as a 15-minute car ride to both Easton and St. Michaels, define the perfect Talbot County location.

24879 W Ferry Neck Rd, Royal Oak

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

$445,000
3 Beds ⋅ 3 Baths
Welcome to this beautifully maintained 3-bedroom, 2.5-bath Cape Cod in the desirable South Beechwood neighborhood! Offering approximately 1,884 square feet of comfortable living space, this home combines timeless character with thoughtful updates and a versatile floor plan. Enjoy three separate living spaces that provide plenty of room to gather, entertain, work, or play. The impressive family room features soaring vaulted ceilings with exposed wood beams, a floor-to-ceiling brick fireplace with a wood-burning stove, and access to the expansive rear deck. The kitchen offers abundant cabinetry and flows seamlessly into the living areas, making it ideal for everyday living and hosting guests. Retreat to the primary suite, complete with a newly renovated bathroom. Outside, you'll love the fully fenced backyard surrounded by mature trees, creating a private setting for relaxation and recreation. The large rear deck is perfect for entertaining, while storage above the attached garage provides extra space for seasonal items and hobbies. Conveniently located near shopping, dining, parks, and schools, this South Beechwood home is ready for its next chapter!

29191 Pin Oak Way, Easton

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$399,990
2 Beds ⋅ 2 Baths
Welcome to the Pacifica II, a thoughtfully designed 1,385 sq. ft home offering 2 bedrooms, 2 bathrooms, and a 2-car garage. The lovely kitchen flows seamlessly into the airy dining area and spacious great room, with access to the covered patio - perfect for indoor-outdoor living. A secluded primary suite features a beautiful private bath and walk-in closet, providing a true retreat. At the front of the home, a dedicated home office offers the ideal space for focused work or hobbies. A convenient hallway connects the kitchen to a pantry and closet, along with the hall bath, laundry room, and secondary bedroom. With its smart layout and inviting spaces, the Pacifica II is designed for both comfort and style.

29500 Cromwell Ln, Easton

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$425,000
2 Beds ⋅ 1 Baths
Welcome to this charming Jack’s Point bungalow, where classic style, modern updates, and thoughtfully restored Craftsman details come together in a warm, bright, and inviting home. Tastefully refreshed throughout and fully furnished the residence features newer flooring, a newer roof, and updated appliances, offering modern comfort while maintaining its timeless appeal. The thoughtfully designed floor plan includes two bedrooms, one bathroom, and an open concept living area that is ideal for both everyday living and effortless entertaining. A screened-in porch provides the perfect space to relax and enjoy the outdoors year-round. The open kitchen showcases beautifully restored original pine cabinetry, blending vintage charm with modern functionality. Outside, the yard features a lovely rose garden and plenty of room to garden, unwind, or entertain. Ideally located near Oxfords restaurants, marinas, parks, and scenic trails, this delightful home offers the perfect combination of character, comfort, and convenience.

104 Bonfield Ave, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415
$285,000
3 Beds ⋅ 1 Baths
Charming 3-bedroom, 1-bath home conveniently located in Easton with easy access to Route 50 and just minutes from historic downtown Easton, shopping, restaurants, parks, and all the town's amenities. Recent owner improvements include updated kitchen flooring and the addition of a rear patio. Other notable features include architectural shingle roofing, an updated heat pump, replacement vinyl windows, and 200-amp electrical service. Ready for immediate occupancy, this property presents an excellent opportunity for first-time homebuyers, downsizers, or investors alike. BACK ON THE MARKET THROUGH NO FAULT OF THE PROPERTY; PREVIOUS BUYER WAS UNABLE TO SECURE FINANCING.

122 Prospect Ave, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$285,000
3 Beds ⋅ 2 Baths
NEW PRICE - Mc Daniel Rancher - This 3 Bedroom and 2 Bathroom rancher in the community of Mc Daniel, is conveniently located approximately 5 miles to St. Michaels. Close to half an acre of land, this property offers plenty of space for gardening and relaxing or grilling on the back deck. Just over 1400 square feet of living space, the dining room opens to the living room creating a generous space for gathering or entertaining. Newer vinyl plank flooring in bedrooms, living and dining rooms. Being sold "as is" condition.

9745 Tilghman Island Rd, Mcdaniel

Listing courtesy of Meredith Fine Properties. Contact: 4107458060
$799,900
3 Beds ⋅ 2 Baths
MAJOR PRICE IMPROVEMENT! SELLERS HAVE FOUND THEIR FOREVER HOME AND ARE READY TO MOVE! BRING ALL REASONABLE AND RESPECTFUL OFFERS! Don't miss this opportunity to own a beautifully maintained 3-bedroom, 2-bath ranch offering more than 2,100 square feet of living space on over an acre in the peaceful community of Glebe Villa with NO HOA. The back deck faces Glebe Creek which leads to the the beautiful Miles River, and the privacy and relaxed lifestyle of Maryland's Eastern Shore. Step inside to a welcoming foyer opening to a bright, comfortable living room filled with natural light. The spacious kitchen features stainless steel appliances, ceramic tile flooring, crown molding, a breakfast bar, and plenty of room for everyday living and entertaining. Just off the kitchen is an impressive 12' x 13' walk-in pantry, providing exceptional storage space. Enjoy casual meals in the breakfast area or gather with family and friends in the dining room area. A true highlight of the home is the expansive 17' x 20' four-season room featuring a beautiful exposed wood beam and walls of windows that bring the outdoors in. Morning coffee, a good book, entertaining friends, or simply relaxing at the end of the day—this is a room you'll want to enjoy year-round. The private primary suite offers a spacious bedroom and en-suite bath, while two additional bedrooms and a second full bathroom provide comfortable accommodations for family or guests. Outside, a large low-maintenance composite deck overlooks the peaceful backyard and provides the perfect setting for outdoor dining, entertaining, or simply enjoying the tranquil surroundings and views toward Glebe Creek. Access to the Miles River offers opportunities for kayaking, canoeing, fishing, and enjoying life on the water. Additional features include an attached 1½-car garage and a generously sized laundry room conveniently located just inside the garage entrance. If you've been looking for space, privacy, water access and the relaxed Eastern Shore lifestyle, this beautifully cared-for property deserves another look. With the new price and motivated sellers, now is the time to schedule your private showing!

8992 Glebe Creek Rd, Easton

Listing courtesy of Harlan C. Williams Co.. 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
$350,000
4 Beds ⋅ 2 Baths
Beautifully updated, stylish split-level residence blends thoughtful design with everyday comfort. A 3 or 4 bedroom, 2 full bath home that feels both welcoming and well cared for. Numerous upgrades can be found throughout. The main-level features an open floor plan with the kitchen flowing into the living room, and updated flooring extends throughout. The lower level expands the living space with a comfortable 4th bedroom or family room or bonus room ideal for a home office, and a large utility room with laundry and abundant storage. large and private fenced rear yard with storage shed. Ideally located on Petunia Drive, this home enjoys easy access to historic downtown, local parks, shopping, dining, and major routes - offering a perfect balance of small-town charm and everyday convenience. Don't miss this one!

29397 Petunia Dr, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$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
$995,000
3 Beds ⋅ 3 Baths
Extremely well maintained, inside and out, 3 bedroom 2 1/2 bath house with an oversized 2 car detached garage, huge back yard and within walking distance to downtown St. Michael's! Since the owner purchased this house there has been a primary first floor master addition, all new windows throughout, updated stainless appliances, professional interior designer decorating, all new extensive landscaping with full irrigation and so much more!

101 Seymour, Saint Michaels

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$2,450,000
6 Beds ⋅ 6 Baths
This exceptional waterfront estate was thoughtfully designed and custom built by its current owner after years of meticulous research and planning, drawing architectural inspiration from the timeless elegance of Colonial Williamsburg. Constructed with an uncompromising commitment to quality and authenticity, this remarkable residence is a true showcase of enduring craftsmanship. Offering 6 bedrooms, 5 full baths, 1 half bath, and an impressive 7 fireplaces, the home is rich with period-inspired architectural details. From the Flemish Bond brickwork and cypress plank siding to the one-of-a-kind, 2.5-inch-thick solid cherry and mahogany entry door, every element was carefully selected to reflect both beauty and longevity. Exceptional custom woodwork is found throughout the home, complemented by stunning Brazilian Teak, Brazilian Cherry, and White Oak hardwood flooring. Adding to the home’s distinction are custom light fixtures crafted by Virginia MetalCrafters, among the final pieces ever produced by the renowned Virginia manufacturer. The chef’s kitchen was designed with both elegance and functionality in mind, featuring custom cherry cabinetry, dual sinks, dual dishwashers, dual Sub-Zero refrigerator and freezer units, and abundant workspace for entertaining or everyday living. The inviting living room showcases custom built-in cabinetry and a magnificent fireplace designed to accommodate both a traditional open hearth and a wood-burning stove. The spacious first-floor primary suite offers a private retreat complete with a luxurious en-suite bath featuring a jetted soaking tub, walk-in shower, and generous walk-in closet. Upstairs, five additional bedrooms enjoy abundant natural light, southern exposure, and beautiful water views. Nearly every principal living space throughout the home captures breathtaking southern-facing waterfront vistas, creating a seamless connection between the interior and its spectacular setting. Outdoor living is equally impressive. A gracious waterside patio with elegant bifurcated brick steps leads to the expansive 720-square-foot swimming pool, creating an ideal space for relaxing or entertaining. Beyond, the riprap-protected shoreline leads to a custom private dock with approximately 3 feet of water depth at mean low water (MLW), providing convenient access to the water. A rare offering on Maryland’s Eastern Shore, this extraordinary waterfront home blends historic architectural inspiration with modern comfort and exceptional craftsmanship. Designed and built to stand the test of time, it is a legacy property meant to be enjoyed for generations.

7250 Maxmore Creek Dr, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 770-9255
$465,000
2 Beds ⋅ 2 Baths
Chesapeake by Del Webb. Thurston model single-story in the Easton Club East, 55+ active adult community. This rarely available, single-owner home is move-in ready and boasts the comfort of a recently upgraded kitchen and HVAC system with exceptional views of the Lyons family farm. This desirable model features a spacious layout with Southern exposure and plenty of large windows. The spacious Florida room overlooks the backyard and pastural views. Enjoy every sunset from the comfort of the brick patio surrounded by luscious, mature vegetation. This house features a chef-inspired, open kitchen, plenty of cabinetry and a pantry for storage. Recently upgraded appliances and a gas stove will make meal-prep a cinch. The family room features a gas fireplace, making the room warm and cozy in the wintertime. Entertaining is fun and easy with a pony-wall surrounding the kitchen. On the other side of the kitchen is the formal dining room. The sleeping quarters are separated by the common areas, providing excellent privacy for guests. The main bedroom is in the back of the house with large windows allowing afternoon light into the spacious bedroom and plenty of room for your biggest bed. Unwind in the jetted tub while watching the sunset. Two sinks, lots of bathroom storage and an additional shower make getting ready easy. The suite is made complete with a spacious walk-in closet. The second bedroom is perfect for guests or as an office or craft room. And the second bathroom features a tub and shower combo. Roof (2021) and HVAC (2024). Landscaping is made easy with irrigation. The 2-car garage off of the main street makes running errands quick. The community amenities include Clubhouse, pool and tennis/pickleball courts. Care-free maintenance means the HOA fees take care of yard work and snow removal, so the only thing you’ll have to worry about is living.

29720 Lyons Dr, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415
$275,000
3 Beds ⋅ 1 Baths
This well-maintained home offers a peaceful Eastern Shore lifestyle with easy access to boating, fishing, crabbing, local marinas, and waterfront dining. Enjoy the relaxed island atmosphere while still being just a short drive from historic St. Michaels and other nearby amenities. The property features comfortable living spaces, a spacious yard, and the opportunity to enjoy all that Tilghman Island has to offer. Whether you're looking for a primary residence, vacation retreat, or investment opportunity, this home provides the perfect setting to experience Maryland's Chesapeake Bay lifestyle. Currently priced significantly under current appraised value!!!

21647 Camper Cir, Tilghman

Listing courtesy of Keller Williams Realty. Contact: 3023600300
$6,375,000
2 Beds ⋅ 3 Baths
Duvall Farm is a rare Eastern Shore offering — a 408± acre farm that blends meaningful conservation efforts with immense easement potential, productive farmland, and refined residential improvements in a location between Easton and Oxford. Significant in both scale and character, the farm is comprised of 20 recorded parcels, presenting long-term value and a wide range of opportunities. The land itself is remarkable. With significant acreage enrolled in the Conservation Reserve Program, over 185± acres provide restored habitat for wildlife and waterfowl. Another 50± acres remain under active cultivation, sustaining the farm’s agricultural heritage. The balance of the property presents a diverse mix of wetlands, mature woodland, wooded buffers, upland habitat, and scenic fields. These varied landscapes support habitat restoration and sporting use, while offering beautiful vistas in every season. A carefully maintained network of trails, and farm lanes provide access throughout the property, making it well-suited for recreation, hunting, and conservation management. At the heart of Duvall Farm is Duvall Lodge, constructed in 2006 by Ilex Construction. Drawing inspiration from Tennessee Pioneer architecture, the lodge is both timeless and inviting. The design embraces rustic authenticity while incorporating every modern comfort. Inside, the great room makes a dramatic impression with soaring ceilings, reclaimed timbers, wide-plank wood floors, and a massive stone fireplace that anchors the space. Exposed beams and natural materials create a warm ambiance, while broad windows and doors seamlessly connect the interior to the surrounding landscape. One of the lodge’s defining features is its full wraparound screened porch, offering sweeping views over a tranquil pond, stocked with bass and with a small pier. Whether for quiet mornings or gatherings with friends, the porch underscores the property’s seamless blend of indoor and outdoor living. Nearby, a hand-hewn log guest cabin extends the accommodations, creating a setting well suited to hosting family and friends. The improvements are understated yet thoughtful, designed to complement rather than dominate the landscape. They reflect the same stewardship evident across the farm itself — an approach that values authenticity, conservation, and the enduring character of the land. Duvall Farm is more than acreage; it is a complete environment, where agricultural productivity, habitat diversity, and architectural charm intersect. Few properties on Maryland’s Eastern Shore offer this combination of size, recorded parcels, conservation value, and a central lodge that feels historic with modern amenities. The location, just minutes from Easton and Oxford, places Duvall Farm within easy reach of the region’s cultural and culinary attractions, while the sheer scale of the farm ensures privacy and a retreat-like atmosphere. For those seeking a legacy property, conservation showcase, sporting retreat, or family compound, Duvall Farm represents an unparalleled opportunity. With its rich mix of land, water, and architecture, it is a property of enduring importance — one that honors the past while offering a wide horizon for the future. Please Note, tax ID and Property Taxes are showing the information on record for the improved parcel. Please contact agent for additional parcel information.

6150 Oxford Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 770-9255
$1,095,000
3 Beds ⋅ 3 Baths
Waterfront, a deeded boat slip, off-street parking, and a single-car garage with additional storage set the stage for this thoughtfully redesigned coastal retreat in the heart of Oxford. Completely renovated from top to bottom, this 3 bedroom, 2.5 bathroom home blends timeless Eastern Shore charm with luxury finishes and exceptional boating amenities. Every detail has been carefully curated, from the new hardwood flooring and fresh paint throughout to the completely remodeled gourmet kitchen featuring high-end appliances, quartz and soapstone countertops, custom cabinetry, and a butler's pantry connecting the kitchen and dining room. The dining room is anchored by a beautiful masonry fireplace with a gas insert, while the custom "Wine Snug" offers built-in wine racks, a wine refrigerator, and handcrafted wrought iron doors. Designed to maximize its setting, the home captures water views from both the front and rear, with sightlines straight through the home to the water. Upstairs, the primary suite opens to a private balcony overlooking the harbor, and the conveniently located second-floor laundry adds everyday functionality. For boating enthusiasts, the property includes a deeded 40’ boat slip accommodating with approximately 5’ MLW. Ideally located just moments from downtown Oxford, you'll enjoy easy access to marinas, the Oxford Ferry, waterfront parks, and local favorites like Doc's Sunset Grille with frequent live music. Whether you're searching for a full-time residence, weekend getaway, or luxury second home, 100 W. Pier Street offers the perfect blend of water views, boating access, modern updates, and the relaxed Eastern Shore lifestyle.

100 Pier St W, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$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
$495,000
3 Beds ⋅ 3 Baths
Welcome to easy living in one of Easton's most sought-after 55+ communities. Situated on a desirable corner lot with mature landscaping, this well-maintained Thurston model offers a thoughtfully designed floor plan with a first-floor primary suite, an additional main-level bedroom and full bath, a spacious family room open to the kitchen, and a bright sunroom. Upstairs offers a private guest suite and versatile loft, perfect for visitors or a home office. Recent updates include fresh paint in select rooms. Additional highlights include hardwood flooring throughout the main living areas, a two-car garage, irrigation system, and private patio. Community amenities include a clubhouse with a fitness center and game rooms, an outdoor pool, tennis courts, and walking trails. Conveniently located just minutes from downtown Easton, shopping, restaurants, and medical facilities.

29833 Hillary Ave, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$219,700
2 Beds ⋅ 2 Baths
Discover a unique investment opportunity in the charming Victorian-style home located in the serene Tilghman Island. This detached residence, built in 1900, boasts 2 over/under units of well-maintained living space, each featuring a spacious bedroom and full bathroom. The interior is adorned with hardwood and partially carpeted floors, enhancing its classic appeal. Investors will appreciate the built-in features, energy-efficient double-pane windows, and a cozy gas fireplace, perfect for attracting quality tenants. The country-style kitchen is equipped with essential appliances, including a refrigerator, built-in microwave, oven/range, dishwasher, and washer/dryer, ensuring convenience for future occupants. The expansive 0.42-acre lot offers ample outdoor space, complemented by inviting patios and porches, ideal for relaxation or entertaining. With off-street parking and a shed for additional storage, this property is primed for rental income or long-term appreciation. Seize this chance to invest in a timeless gem with significant potential!

4869 Bar Neck Rd, Tilghman

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

000 Quiet Hollow Ct, Wye Mills

Listing courtesy of Koch Realty, Inc.. Contact: 410-320-6422