444 properties for sale in Tilghman Island

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!

Experience authentic Eastern Shore living in this peaceful Chesapeake Bay retreat, located just steps from historic Dogwood Harbour, home to the Skipjacksthe last working commercial sailing fleet in the United States. This charming home features three first-floor bedrooms and a full bath, providing comfortable one-level living for family and guests. The remodeled eat-in kitchen showcases granite countertops and opens to a spacious outdoor deck, perfect for entertaining or relaxing while enjoying the coastal atmosphere. Upstairs, the private primary suite offers a full bath with a spa tub, creating a tranquil retreat. Also on the second level is an expansive open living area complete with a half bath and wet bar, providing exceptional flexibility for entertaining, recreation, a home office, or additional guest accommodations. Recent improvements include a new roof (2026), luxury vinyl plank flooring throughout, a new washer and dryer, a new stove/range, and a new central heating and air

Turn-key waterfront home with spectacular views from every room. The entire house has been taken down to the studs: exterior and interior walls reframed; shed dormers installed; glass doors and windows placed in every wall; renovated kitchen with quartz countertops, semi-custom cabinets, new appliances, a Butler's Pantry, two new staircases, all new plumbing, electric, HVAC, built-ins, hardi-plank siding, Azek trim, composite decking, custom garage doors. The list goes on.Tilghman on Chesapeake' has coveted amenities including a clubhouse and outdoor pool on the water, piers, boat-slips, and sweeping views of the watermen departing at sun-rise. Restaurants and daily amenities are nearby including groceries, liquor, a deli and the best cup of coffee on the Eastern Shore served at the Country Store. Spectacular views, and laid-back community charm, is the timeless appeal that makes Tilghman Island so special. The home can convey furnished if desired

Tucked away beneath a canopy of mature trees, 6114 Sunset Lane feels like a storybook retreat along the shores of the Chesapeake Bay. A tree-lined, pebbled circular driveway welcomes you home, setting the tone for the quiet beauty and sense of escape found throughout this special waterfront property. Surrounded by nature and framed by peaceful water views, the home offers a slower, more intentional way of living. Begin your mornings with sunlight dancing across the bay, spend your afternoons enjoying the gentle rhythm of the water, and end each day beneath the soft colors of an Eastern Shore sunset. Inside, abundant natural light pours through the home, creating bright, inviting spaces that feel effortlessly connected to the surrounding landscape. The thoughtfully renovated three-bedroom, two-full-bathroom residence blends timeless character with elevated modern comfort. At the heart of the home is the beautifully renovated kitchen, where rich soapstone countertops bring natural warmth

Experience Eastern Shore waterfront living in this charming Chesapeake Bay home, where breathtaking sunset views and a relaxed coastal atmosphere create the perfect setting for everyday living or weekend escapes. Designed to embrace the waterfront lifestyle, the property offers exceptional indoor and outdoor spaces for entertaining family and friends. A brick walkway welcomes you to the inviting front porch and foyer, where hardwood floors flow throughout the home. Recently renovated, the kitchen features white cabinetry, quartz countertops and large windows that fill the space with natural light while overlooking the front yard. The spacious living room is highlighted by a cathedral ceiling and opening to a year-round sunroom surrounded by walls of windows showcasing panoramic views of the Chesapeake Bay. The primary suite features a newly renovated bath with a tile and glass shower. Two guest bedrooms, an office and two additional beautifully renovated full baths occupy the opposite

Live the Tilghman Island lifestyle just steps from the Chesapeake Bay. Perfectly positioned in the heart of historic Tilghman Island, this updated four-bedroom home offers the ability to enjoy one of Maryland's most authentic waterfront communities without the waterfront price tag. Walk to marinas, waterfront restaurants, charter fishing, Tilghman Wharf, and the iconic drawbridge, or spend your days exploring the Chesapeake by boat, kayak, or bicycle. Originally inspired by one of Tilghman's classic'W' homes, the residence blends timeless island character with modern updates. Inside, you'll find a spacious, open floor plan featuring an updated kitchen with granite countertops, stainless steel appliances, and abundant cabinetry, along with beautifully renovated bathrooms, new flooring, and a flexible layout that includes a first-floor bedroom and full bathideal for guests or one-level living. Three additional bedrooms and another updated full bath are located upstairs, providing plenty

Price reduced significantly! Beautiful views of Harris Creek and the Choptank River beyond provide a stunning backdrop for this beautifully maintained home in the established community of Tilghman on Chesapeake. A welcoming front porch framed by mature landscaping and colorful gardens leads into a bright, light-filled interior featuring soaring two-story ceilings, hardwood floors, crown moldings, and abundant natural light. Designed for both everyday living and entertaining, the gourmet kitchen opens to a spacious family room with a gas fireplace, breakfast area, and inviting sunroom. The adjoining rear deck, complete with a hot tub, provides a wonderful setting for outdoor entertaining while overlooking the beautifully landscaped grounds and tranquil water views. The main level also includes gracious formal living and dining rooms, as well as a private office. The upper level overlooks the family room below and features a spacious primary suite with a private balcony and luxurious ens

Welcome to Tilghman on Chesapeake! Discover this peaceful community in a serene setting away from the crowds of traditional beach towns, yet conveniently located near the charming waterfront town of St. Michaels and the amenities of Easton, Maryland. This beautiful Sussex floorplan features 3 bedrooms, 2 full bathrooms, cozy front porch and a 2-car garage. The home includes beautiful quartz countertops, stainless steel appliances, a large island and a spacious family room highlighted by a gas fireplace. The private owners retreat offers a relaxing escape, including a Venetian-style private bathroom. Complete with a new home warranty for added peace of mind, this home combines modern finishes, everyday comfort, and the appeal of Eastern Shore living. Enjoy an exceptional community lifestyle with amenities including a waterfront clubhouse, swimming pool, picnic area, and community pier. Boat slips are also available for purchase or lease, making it easy to embrace the Chesapeake Bay life

Be sure to watch the video tour to experience the property and setting. Rare opportunity in the coveted Village of Fairbank on Tilghman Island. Set on nearly an acre in a peaceful Eastern Shore setting, this charming 1900 traditional home offers 1,720 square feet of living space with three bedrooms, two full baths, and the warmth and character of a wood-burning fireplace. One of the property's most distinctive features is its setting along Black Walnut Cove, just beyond the backyard, offering an idyllic backdrop for kayaking, canoeing, and enjoying life near the water. The expansive. 93-acre lot provides plenty of room for outdoor entertaining, gardening, or simply relaxing and taking in the natural surroundings. Fairbank on Tilghman is a special community where neighbors know one another and take care of eachother. Whether you're searching for a full-time residence or a weekend retreat, this property offers a wonderful opportunity to enjoy the character of Tilghman Island, the beauty

Unique, one-of-a-kind property located in the heart of Tilghman Island, offering unparalleled tranquility and breathtaking water views overlooking Dogwood Harbor. Welcome to your private Eastern Shore retreat! This beautifully updated water-view home captures the essence of coastal living with sweeping views of the harbor and surrounding wildlife. Enjoy stunning sunsets and peaceful mornings from the expansive screened porch or spacious deckperfect for relaxing or entertaining while taking in the natural beauty of the island. Inside, the home has been thoughtfully updated and features a bright, open living area and a beautifully renovated kitchen designed for both everyday living and gatherings with family and friends. The spacious primary suite offers a private bath and walk-in closet, along with panoramic water views and direct access to the second-story porch/deck with a retractable awningan ideal place to unwind and enjoy the serene surroundings. Two additional guest bedrooms and a

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This ranch-style residence, built in 1964 and the original owner, set on a sprawling 1-acre lot that backs to serene trees and boasts river views from the front yard. The property features a brick front and shingle siding. This home has1,636 square feet of finished living space. The open layout connects the dining and living areas, enhanced by elegant wood floors and built-in cabinetry. A cozy wood-burning fireplace serves as a focal point, perfect for creating a warm ambiance during cooler evenings. The eat-in kitchen is equipped with essential appliances including a single oven, electric cooktop, and refrigerator, complemented by ample table space for casual dining. The home features two bedrooms a full bathroom featuring a tub shower combination and ceramic tile accents. Additional highlights include ceiling fans for optimal airflow and an attic for extra storage. Outside the expansive lot offers a level terrain with a front yard, rear yard, and side yards, ideal for outdoor activit

Beautifully upgraded and thoughtfully designed, custom finishes, and every modern convenience. The gourmet kitchen features dual fuel gas cook top and electric oven in professional grade stove, quartz countertops, professional grade appliances, and premium appointments, flowing seamlessly into warm hardwood floors and a cozy gas fireplace beneath a striking coffered ceiling. Beautifully curated designer wallpaper accents throughout this stunning model home! Offering 4 bedrooms and 2.5 baths, the home includes a firstfloor primary suite with an ensuite spa bath, custom shower, and generous walkin closets. Additional highlights include Hardie Plank siding, custom black windows, a Trex deck, paved driveway, 1car garage, and excellent storage throughout. Located just a short walk to the heart of St. Michaels, youll enjoy easy access to charming shops, restaurants, waterfront activities, and yearround festivals

Welcome to Chesapeake Heights! Situated on 2.2 acres backing to trees, this beautifully maintained Colonial offers over 3,100 total square feet of living space. Enjoy the privacy of a wooded setting along with community beach access! Abundant wildlife here with deer, turkey, foxes and birds with a creek that runs in the back part of property. Offers plenty of outdoor activities including riding dirt bikes and raising chickens! Inside, youll find hardwood floors, comfortable gathering spaces, and a spacious kitchen with upgraded countertops, a center island, and stainless steel appliances. Recent updates include a new double oven (2026), dishwasher (2024), and built-in over-the-range microwave (2025). The kitchen opens to the family room, keeping everyone connected, while the separate dining room offers plenty of room for holiday meals and entertaining. Two fireplaces with marble surrounds and glass doors add warmth and character. Upstairs, the primary bedroom includes a private bath, a

Mechanics/workshop dream. Nestled in the serene Shady Side community, this charming ranch-style home offers a perfect blend of comfort and functionality. With 1,489 square feet of thoughtfully designed living space, this residence features three inviting bedrooms and two full bathrooms, ideal for both relaxation and entertaining. Step inside to discover a warm and welcoming interior, highlighted by a cozy breakfast area and a combination kitchen/dining space that encourages gatherings. The kitchen is equipped with stainless steel appliances, including a gas oven/range and a convenient dishwasher, making meal prep a delight. Enjoy the ease of main-floor laundry and the comfort of ceiling fans throughout. The exterior of the home is equally appealing, featuring low-maintenance vinyl siding and a spacious lot of over half an acre that backs to lush trees, providing a tranquil backdrop. Outdoor living is enhanced by a charming patio and porch, perfect for morning coffee or evening relaxati

Welcome to Woodland Hills! This 4 bedroom, 3.5 bathroom home on a beautiful wooded lot, is ready for its next owner. The split-level home is larger than it seems, featuring a large addition and TWO primary suites. On the main level you will find a large living room, a bright eat-in kitchen, a formal dining room, a large laundry/mud room, and an over-sized primary bedroom with an en-suite bathroom. Upstairs, there is a second primary suite, two additional bedrooms, and a guest bathroom. In the basement you will find a rec room with wood burning fireplace and a half bathroom. Outside is a large two car detached garage, a huge deck, and a beautiful wooded almost 1.5 acre lot situated on a private cul-de-sac. Recent updates to the property include a new roof in 2024, new HVACs in 2016 and 2020, and new garage door openers and driveway in 2026. This northern Calvert location is only minutes from the Chesapeake Bay and is a commuters dream, offering easy access to major commuter routes into

Just reduced to $525,000affordable, turn-key easy living near the water in St. Michaels. Located 1.5 blocks from public boat ramps and marina access, this updated coastal getaway delivers effortless weekend living without Historic District restrictions. Major recent capital investmentsa new roof (2024), updated plumbing (2025), upgraded crawlspace with French drain (2025), and Thompson Creek windowsmean zero weekend project lists. Spend your Saturdays lounging by your private in-ground pool, hosting at the beach bar with cable TV, or storing kayaks and gear in the detached garage. Convenient main-level living just steps from downtown dining, coffee shops, and harbor parks. Perfect as a low-maintenance weekend retreat or primary escape from Day 1

Waterfront opportunity with 7 lots! Unparalleled potential awaits with these 2 tax parcels totaling 7 lots (1.64 Acres / 56,266 SQFT) of prime waterfront ground! Build your ultimate custom dream estate on the water and soak in the sun, breeze, and moonlight from your own private 100-foot pier. With county permitting, there is incredible potential to subdivide the lots for a multi-home spec build or family compound. Don't miss out on this rare coastal canvas! Sale is for 5011 and 5013 W Chalk Point Road together. 5013 MDAA2158- is also active in BRIGHT (address should read 5011 W Chalk Point Rd. Working with BRIGHT to correct) Opportunity is knocking and the water is calling! Owners since 1972 are selling 5011 and 5013 (lots 4,5,6,7,30,31,32) W Chalk Point Road, (formerly known as Henry Road) along with all buildings main house, tenants house, backyard cottage, detached garage, multiple sheds, lean-to, 100ft pier, gazebo. Waterfront lots. 5013 W Chalk Point. Lots 4,5,31,32. Has riparian

Charming home in Northern Calvert County! This beautiful split level offers over 2600 sq ft of living space on a 2.4 acre landscaped lot, with easy access to DC, Annapolis and Baltimore. The best of both worlds: peaceful county living with a commuter friendly location. Main level has hardwood flooring throughout. A cozy family room with a classic brick fireplace, perfect for chilly evenings. Spacious kitchen ready for entertaining, and a professional office tucked away for working from home. Upper level has three bedrooms and two full bathrooms; the primary suite has two closets, one walk in. Lower level has the fourth bedroom, a bathroom, a rec room that walks out to the backyard, and an extra large laundry room /craft room. Outdoor living. A vegetable garden at your easy disposal off the large composite deck overlooking the wooded, private backyard. A two car garage and a shed. This home has it all. Space, privacy, comfort and convenience. Come experience this home yourself

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 1860-1- 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

Welcome to Wyatt's Ridge by Schaefer Homes an exciting new home community nestled in the heart of sought-after Owings, Maryland. With just 22 spacious, wooded homesites, this intimate and private enclave offers the natural beauty, tranquility, and seclusion that today's buyers are searching for, beautifully paired with the exceptional quality craftsmanship and modern design that Schaefer Homes has built its stellar reputation on. For a limited time, take advantage of pre-construction pricing and receive an additional $20,000 in free options when using our preferred Lender and Title Company an extraordinary opportunity to personalize every detail of your brand-new home from the very beginning. Choose from a collection of thoughtfully designed floor plans offering generous living spaces, stunning kitchens, and flexible layouts built to suit the way you live. For those seeking the ease and elegance of main-level living, select plans also offer available first-floor primary suite designs a