Pittsville Homes for Sale

Pittsville Homes for Sale

Welcome to Pittsville, Maryland – a charming town nestled in the heart of Wicomico County. Known for its friendly community and picturesque landscapes, Pittsville offers a delightful blend of rural charm and modern convenience. With a population that reflects the warmth and hospitality of small-town living, this hidden gem is perfect for families, retirees, or anyone looking to escape the hustle and bustle of city life.

Pittsville boasts a rich history, reflected in its quaint architecture and local landmarks. The town is surrounded by beautiful parks and natural areas, providing ample opportunities for outdoor enthusiasts to explore hiking trails, fishing spots, and picnic areas. The local schools are highly regarded, making it an ideal place for families seeking a nurturing environment for their children.

For those considering a move, Pittsville has a variety of homes for sale that cater to diverse tastes and budgets. From charming single-family homes with sprawling yards to modern townhouses in friendly neighborhoods, there’s something for everyone. Many properties feature spacious layouts, updated amenities, and easy access to local shops and restaurants. Whether you’re looking for a cozy starter home or a larger residence to accommodate a growing family, Pittsville’s real estate market is thriving.

Embrace the opportunity to become part of this vibrant community. With its welcoming atmosphere and beautiful surroundings, Pittsville is more than just a place to live; it’s a place to call home. Discover the perfect property today and start your journey in this delightful Maryland town!

Newest Pittsville Homes for Sale

$409,900
3 Beds ⋅ 2 Baths
Step into easy, one-level living with the Emerald by Gemcraft Homes, currently under construction in Pittsville, MD. Situated on a spacious 0.45-acre lot, this thoughtfully designed home offers the perfect blend of comfort and functionality. The welcoming foyer leads to two generously sized bedrooms and a full hall bath, while the hallway opens into a bright and spacious great room that flows seamlessly into the country-style kitchen and dining nook. The kitchen is designed for both everyday living and entertaining, featuring granite countertops, GE stainless steel appliances, abundant cabinet space, and a peninsula with an overhang for additional seating. Privately located at the rear of the home, the expansive owner's suite offers a large walk-in closet and an en-suite bath. Completing the home is a convenient 2-car attached garage. Don't miss the opportunity to own this beautiful new construction home and enjoy the quality craftsmanship Gemcraft Homes is known for.

34910 Main St, Pittsville

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact: 3028460200
$339,900
3 Beds ⋅ 2 Baths
Small town living starts with breakfast and coffee on the back deck! The remainder of the day can be followed by a full list of possibilities as the location for this one level gem is ideal. Just a short drive to the world-famous Ocean City beaches and Assateague National Seashore where the ponies run free and are often seen frolicking in the ocean. The central location is also close to Salisbury with its award-winning zoo, hospital, dining, shopping and nightlife. Downtown Berlin is close by and was voted one of the coolest small towns in America. Tax free shopping is close by as well in neighboring Delaware.   And did I mention that there is NO HOA and SOUGHT AFTER SCHOOLS?   The evenings in your new home can be spent on the country front porch watching a good thunderstorm or winding down the day with a cocktail!   Some additional features for the home include 3 bedrooms and 2 full bathrooms, new sliding door, new dishwasher and microwave, gas heat, city water and trash collection, fiber optics recently installed in the neighborhood, vaulted ceilings, walk-in closets, paved driveway, fenced back yard, 2 outbuildings with electric and a home warranty through October!  Here is your chance to own the perfect size home in the right location and after all....You Deserve It!

34339 Pine Meadows Ln, Pittsville

Listing courtesy of Keller Williams Realty Delmarva. Contact: 4105246400
$319,000
3 Beds ⋅ 2 Baths
Welcome to 34780 Main St., ideally located in the heart of Pittsville, offering small-town charm with easy access to Salisbury and the beautiful beaches of Maryland and Delaware. This immaculate one-story rancher features 3 bedrooms, 2 bathrooms, and a spacious, comfortable layout designed for everyday living. Updates in 2026 include fresh interior paint throughout the entire home, new LVP tile flooring in the large eat-in kitchen and in the laundry room, and new carpet in the living room and the 3 bedrooms. The HVAC system and the hot water heater are just a few years old and the roof is only 10 years old -- for added peace of mind. The home also offers a one-car attached garage and an oversized driveway with plenty of space for multiple vehicles and even a boat. Step outside to the rear deck overlooking the spacious backyard—an ideal setting for relaxing, entertaining, or enjoying the outdoors. Meticulously maintained and truly move-in ready, this home offers the perfect combination of comfort, convenience, and value.

34780 Main St, Pittsville

Listing courtesy of ERA Martin Associates, Shamrock Division. Contact: 4106415000
$899,000
4 Beds ⋅ 5 Baths
This private retreat, ideally positioned between Salisbury and Ocean City, offers a rare combination of privacy, acreage, and refined living that buyers seek on Maryland’s Eastern Shore. Set on just over 9 beautiful acres, the property includes a stately brick Georgian style residence, a gunite saltwater pool, an attached 3 car garage and a versatile 5 car detached garage, all surrounded by State Forest land creating peace and privacy as far as the eye can see. The home’s exterior is designed for low maintenance living with brick & vinyl construction, a paved drive with generous parking and paver walkways. Inside, the home’s expansive interior includes multiple living and entertaining areas, ideal for both everyday living and hosting guests. Large windows throughout invite natural light and showcase the property’s stunning grounds. The first floor features Brazilian cherry hardwood floors, high ceilings, and impressive room sizes. The foyer, living room, formal dining room, and private office create an elegant and functional layout. The gourmet kitchen with cherry cabinets, quartz counters, stainless steel appliances, gas cooktop and double ovens has plenty of cabinet and counter space and opens to a breakfast room, sunroom and a spacious family room with a vaulted ceiling and cozy fireplace. The first‑floor primary suite serves as a true retreat with a fireplace, oversized walk‑in closet with a built-in organizational system, luxurious bath with a beautifully tiled double shower, heated tile floors and double sinks, and adjacent flex room ideal for a gym, office, studio, or nursery space. The second floor offers a private guest suite with its own bath, large walk-in closet, a walk up attic with plenty of storage space. Two additional bedrooms, a hall bath, and a large bonus or game room. Two of the bedrooms have access to the second floor porch on the front of the house. Dual staircases, a formal front staircase and a back staircase leading to the bonus/game room enhance both convenience and privacy. Outdoor living is a highlight of this property. Step outside to your own private retreat, complete with a sparkling saltwater pool and extensive landscaping that creates a peaceful, park-like setting. Whether relaxing poolside or enjoying the open green space, this property offers endless opportunities for outdoor enjoyment. The land is surrounded by hundreds of acres of State Forest providing unmatched privacy and a landscape teeming with wildlife, making this an ideal home for outdoor adventure. Whether you’re seeking quiet country living, room to entertain, or your own personal haven surrounded by nature, this exceptional property offers it all. A detached five-car garage with four overhead doors provides exceptional flexibility for boats, RVs, car storage, or workshop needs adding functionality and complementing the home’s impressive features. A full kitchen can be found in the detached garage along with a half bath, fixed stair to an unfinished area above, dog kennel, whole house 60kw generator and the covered porch overlooking the pool that creates an inviting setting for warm‑weather enjoyment. Don't miss out on your chance to own this beautiful property!

6445 60 Foot Rd, Pittsville

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$590,000
3 Beds ⋅ 3 Baths
Luxury country living! Built in 2020 with 3 bedrooms, 2 bathrooms, on 2 acres of land with multiple outbuildings - let alone the list of finishes (available upon request)! Inside, the home feels fresh and updated with new carpet in the living room and primary bedroom, luxury vinyl flooring in the secondary bedrooms, and fresh paint throughout. The flow of the home connects naturally to the outdoor spaces where you'll find a large screened in porch, patio space, and large fenced in backyard with a shed. The attached garage adds even more flexibility with newly sealed flooring, a screened garage door, and a half bath, creating a practical space for projects, storage, everyday use or entertainment. For those needing extra room, whether personal or business, the property includes multiple outbuildings designed for versatility. The 30 x 50 pole barn features dual-entry garage doors, office space, and a half bath. The second outbuilding offers another 24 x 40 space with an attached overhang for additional space or storage. Other improvements include a full-home backup generator, water treatment system, termite protection system, a surrounding camera system, and a clean full concrete crawlspace for added peace of mind. Full list of finishes available upon request. Schedule a tour today!

8225 Whitesville Rd, Pittsville

Listing courtesy of Coastal Life Realty Group LLC. Contact: (443) 235-8382
$421,900
4 Beds ⋅ 3 Baths
Introducing the Hamilton, a beautifully designed to-be-built home by Gemcraft Homes in Pittsville, MD, offering the perfect blend of space, comfort, and flexibility. As you enter the home, you're welcomed by a versatile Choice Room off the foyer ideal for a formal living room, home office, playroom, or whatever best fits your lifestyle. Continue down the hall to the spacious Great Room, which flows seamlessly into the classically designed kitchen, creating an open-concept layout perfect for everyday living and entertaining. An optional fireplace can be added to create a warm and inviting gathering space. A convenient mudroom located off the garage entrance completes the thoughtfully designed first floor. Upstairs, the private primary suite serves as a relaxing retreat, featuring a spacious bedroom, large walk-in closet, and an ensuite bath with options including a luxurious Super Bath with soaking tub and separate shower or a Venetian-style bath with a large glass-enclosed shower and built-in seat. Three additional bedrooms, all with ample closet space, share the second floor along with a centrally located laundry room for added convenience. With a variety of available upgrades, extensions, and personalization options, the Hamilton offers the opportunity to create the dream home you've always wanted. Conveniently located in Pittsville with easy access to local shopping and dining.

TBD Main St, Pittsville

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact: 3028460200
$418,990
3 Beds ⋅ 2 Baths
Welcome to the Wilmington, a beautifully designed to-be-built ranch home by Gemcraft Homes located in Pittsville, MD. Offering 3 bedrooms, 2 bathrooms, and a 2-car attached garage, this thoughtfully crafted floor plan combines modern design with the convenience of one-level living. As you enter through the foyer, you are greeted by a formal dining room, perfect for hosting family dinners and special occasions. The home then opens into a spacious open-concept layout featuring a well-appointed kitchen and expansive great room. Designed with both functionality and entertaining in mind, the kitchen offers ample cabinetry, generous counter space, and room for casual dining, while the great room provides a comfortable gathering space for everyday living. Privately situated at the rear of the home, the owner's suite serves as a relaxing retreat with a spacious bedroom, two closets, and a private en-suite bath. Two additional bedrooms are located on the opposite side of the home and share a full hall bathroom. A conveniently located laundry room adds to the home's practical design. Personalize your Wilmington with a variety of available options, including a cozy gas fireplace in the great room, or a second-floor loft featuring a fourth bedroom and full bathroom for additional living space. With its open layout, flexible design options, and quality craftsmanship, the Wilmington offers the perfect opportunity to build your dream home in Pittsville, conveniently located near shopping, dining, recreation, and nearby beaches.

TBD Main St, Pittsville

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact: 3028460200
$451,900
3 Beds ⋅ 3 Baths
Welcome to the Frankford, a beautifully designed to-be-built home by Gemcraft Homes located in Pittsville, MD. This thoughtfully crafted floor plan offers 3 bedrooms, 2.5 bathrooms, a 2-car attached garage, and the option for a fourth bedroom, providing flexibility to fit your lifestyle. As you enter the home, you are welcomed by a formal dining room, perfect for hosting family gatherings and special occasions. The heart of the home features an open kitchen and breakfast area that flows seamlessly into the impressive two-story family room, creating a bright and spacious atmosphere ideal for both everyday living and entertaining. Convenience is at the forefront of this design with a first-floor laundry room and a spacious first-floor primary. The primary bedroom features a large walk-in closet and a private en-suite bathroom, offering comfort and privacy. Upstairs, you'll find two additional bedrooms that share a full bathroom, along with the option to add a fourth bedroom to accommodate a growing family, guests, or a home office. Combining timeless design, functional living spaces, and quality craftsmanship, the Frankford offers the perfect opportunity to build your dream home in the charming town of Pittsville, just a short drive from local shopping, dining, and area beaches.

TBD Main St, Pittsville

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact: 3028460200
$441,900
3 Beds ⋅ 2 Baths
Welcome to the Sussex, a beautifully designed to-be-built ranch style home by Gemcraft Homes that perfectly blends style, comfort, and functionality with the ease of single-level living. This popular floor plan offers impressive curb appeal and a thoughtfully crafted layout designed to accommodate today's modern lifestyle. Step inside to an inviting open-concept floor plan where the kitchen, breakfast area, and great room seamlessly flow together, creating the perfect space for entertaining guests or enjoying everyday life. Personalize your home with options to add a bright and airy sunroom or a screened porch, allowing you to extend your living space and enjoy the outdoors year-round. Privately situated off the great room, the spacious owner's suite serves as a relaxing retreat, featuring two walk-in closets and a luxurious en-suite bath. Buyers can choose from multiple owner's bath configurations, including a Venetian-style bath with a large shower and bench, a Roman-style walk-in shower, or a spa-inspired super bath complete with a soaking tub and separate shower. Two additional bedrooms and a full hall bath provide comfortable accommodations for family and guests. For those needing even more space, optional upgrades include a second floor featuring a loft, additional bedroom, and full bath, or a finished lower level offering a recreation room, den, full bath, and abundant storage space. The Sussex delivers the perfect combination of flexible living spaces, modern design, and quality craftsmanship, making it an exceptional place to call home.

TBD Old Ocean City Rd, Pittsville

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact: 3028460200
$411,990
4 Beds ⋅ 3 Baths
Welcome to the Ruby, a thoughtfully designed to-be-built home by Gemcraft Homes that offers the perfect blend of space, comfort, and flexibility. The first floor features an expansive open-concept layout where the Great Room, Breakfast area, and Kitchen flow seamlessly together, creating an ideal space for both everyday living and entertaining. The versatile flex can also be configured as a private library, home office, or playroom to suit your lifestyle needs. The spacious kitchen is designed with functionality in mind, offering abundant cabinetry, generous counter space, and a deep pantry for exceptional storage and organization. An optional kitchen island is available to provide even more workspace and seating. Upstairs, the generous Owner's Suite serves as a private retreat, complete with a large walk-in closet and an en-suite bathroom featuring a double vanity, oversized shower, and private water closet. Three additional bedrooms, a full hall bath, and a conveniently located laundry room complete the second floor. A large loft area provides additional living space and may be converted into an optional fifth bedroom, offering even greater flexibility for growing families or guests. With its open design, versatile living spaces, and quality craftsmanship, the Ruby offers everything you need to create your dream home.

TBD Old Ocean City Rd, Pittsville

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact: 3028460200
$385,990
4 Beds ⋅ 3 Baths
Welcome to the Pearl, a beautifully designed new construction home that is to be built in Pittsville, MD, offering 4 bedrooms, 2.5 bathrooms, and a 2-car attached garage. Part of Gemcraft Homes' signature Gem Series, this thoughtfully designed home features an open-concept first floor perfect for both everyday living and entertaining. The spacious great room flows seamlessly into the kitchen and breakfast area, a sliding glass door off the kitchen fills the home with natural light and provides easy access to the backyard. Upstairs, the generous primary suite offers a large walk-in closet and a private en-suite bathroom complete with a shower and private water closet. Three additional bedrooms, a full hall bathroom, and a conveniently located laundry closet complete the second floor. With modern finishes, functional living spaces, and quality craftsmanship throughout, this new construction home offers the perfect combination of comfort and style in a convenient Pittsville location.

TBD Old Ocean City Rd, Pittsville

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact: 3028460200
$174,500
2 Beds ⋅ 1 Baths
Adorable home on almost 2 acres and in great location - close to shopping dining and events, 10mi to America's Coolest Small Town, Berlin, 12mi to Downtown Salisbury, 20mi to Ocean City's beach and boardwalk. Property is move-in ready and offers a spacious layout. As you enter, you are greeted by the sitting room, a bright and cheery place to chat with friends, relax and read, or catch up on your favorite TV series. Continue your tour and you will find the large eat-in kitchen with white cabinets. The spacious first-floor bedroom with a full, en-suite bath - tub/shower combo and linen closet. There is also a functional mudroom with laundry area, coat closet and an additional closet, completes the first floor. Upstairs you will find a large bonus room w/a closet which offers a flexible living space - media room, game room, guest room - your choice! A 2nd nice-sized bedroom completes this charming home.

35534 Mount Hermon Rd, Pittsville

Listing courtesy of Northrop Realty. Contact: 4105310321
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