552 houses for sale in Pittsville town

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 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

Builder-paid rate buydown or a $15K closing-cost credit instead*. With an acceptable offer, PLUS a New home 10 year Structual warranty! Brand-new and move-in ready, 6 Preakness Drive is a single-level coastal ranch in Triple Crown Estates, Ocean Pines, built by local builder Del Mar Construction. Approximately 2,200 finished square feet on a 0.29-acre lot. Vaulted ceilings open up the living room and kitchen, where you'll find shaker-style cabinetry, quartz countertops, a large center island, and a walk-in pantry. The split-bedroom floor plan places the primary suite on its own side of the home, with dual walk-in closets and a spa-style bath featuring a freestanding soaking tub, an oversized walk-in shower with floor-to-ceiling tile and frameless glass, and a double-bowl vanity. Three additional bedrooms and a full bath sit on the opposite side, The main-level laundry room includes cabinetry and a utility sink. Outside, relax on the covered front porch or the oversized screened rear de

Enjoy peaceful golf course views from this inviting 3-bedroom, 2-bath rancher overlooking the 4th hole of the Robert Trent Jones-designed golf course. Cathedral ceilings and skylights fill the home with natural light, creating a bright and airy atmosphere. The expansive living room offers plenty of space to relax or entertain, with beautiful views of the fairway. The eat-in kitchen features a breakfast bar and connects to a cozy sunroom, perfect for a home office, sitting area, or flexible guest space. A spacious mudroom, separate laundry room, and walk-in pantry provide plenty of everyday convenience and storage. Pull-down stairs in the hallway lead to a full-height attic offering additional storage possibilities. An attached two-car garage adds even more functionality. Step outside onto the deck to enjoy your morning coffee, unwind at the end of the day, or simply take in the scenic golf course setting. A wonderful opportunity to enjoy comfortable one-level living with a beautiful ba

Motivated seller, bring all offers! Move-In Ready & Furnished in Ocean Pines! New roof, vapor barrier and dehumidifier installed 09/08/26! Welcome to 150 Sandyhook Road, a beautifully situated 3-bedroom, 2-bath home on a generous. 47-acre lot in desirable Ocean Pines. Offered fully furnished and move-in ready, this home makes it easy to start enjoying the Eastern Shore lifestyle from day one. Relax and entertain from the inviting screened-in porch, perfect for morning coffee, afternoon drinks, or gathering with friends and family. The property also features an oversized insulated garage with built-in storage cabinets, providing plenty of room for vehicles, bikes, beach gear, tools, and recreational equipment. Major peace-of-mind update. A new roof was installed September 8, 2026 as well as a new vapor barrier and dehumidifier in the crawl space. This home also features on-demand hot water, adding efficiency and convenience. With three bedrooms, two full bathrooms, a spacious lot, ample

If you are seeking a home that is better than new, this is it! This immaculate approximately 3600sf. Home in The Point at Ocean Pines offers exceptional living space, extensive recent upgrades, and an incredible bonus for the boating enthusiastthe Seller has a deeded boat slip at nearby Pines Point Marina with a boat lift also listed for sale! Beautiful pond views welcome you from the wraparound front porch. Inside, the open floor plan offers everything you could want on the main level, including a luxurious Owner's Suite, private home office, first-floor laundry and a spacious gourmet kitchen designed for entertaining. The kitchen features quartz countertops with breakfast bar, subway tile backsplash, gas cooking, pendant lighting and stainless appliances. Hardwood flooring and beautiful tile complement the home's bright, coastal feel. Upstairs, a dramatic foyer with arched detail, cathedral ceiling and chandelier leads to a second Owner's Suite with en suite bath, additional bedrooms

This is the location in The Parke you've been waiting for, tucked away for serene privacy on a large 12,858 square foot, cul-de-sac lot backing to woods! This Royal Tern floor plan offers 2,587 sq. Ft. of comfortable living space, 3 bedrooms/2 full baths downstairs, and an additional 4th bedroom and full bath upstairs with loft area. The main level features a spacious living room with cathedral ceiling, ceiling fan and a sun tunnel style skylight lets in extra natural light. A double-sided gas fireplace with blower creates a warm connection to the adjoining spaces. The kitchen offers numerous upgrades just completed in 2025including a JennAir gas cooktop, new quartz countertops and subway tile backsplash. The added wall of custom cabinetry in this home provides ample storage space for all your kitchen needs. As you enter in the front door, the home layout offers a formal dining room space that boasts hardwood floors that continue throughout the hall, kitchen and breakfast area. The fro

From sunrise to sunset, this property offers breathtaking, wide-angle river vistas, while maintaining a secure, protected harbor for your watercraft and a picturesque wide lagoon for peaceful relaxation. Character, warmth, and craftsmanship define the penthouse-style layout, uniquely designed specifically to capture the panoramic water views from your elevated primary living and entertaining spaces. Crowning the roofline is a custom cupola that evokes a classic maritime-inspired charm. Quality-built with 2x6 exterior wall framing set upon an elevated 5-course masonry foundation. The family room is positioned as a vast, casual gathering hub. This large open area blends every day comfort with custom architectural elements. Newly remodeled 4 years ago, the kitchen contains tile, granite, a classic farmhouse sink, Samsung stainless steel appliances, spacious pantry, and vaulted ceilings. Sliding glass doors open to a balcony that is equipped with a spiral stairway serving as a secondary me

Welcome to Piney Island, a sought-after community offering a scenic, private setting close to everything that makes coastal living so desirable. Situated across the street from the St. Martin River and just minutes from Ocean Citys beaches, Assawoman Bay, and the charming town of Berlin, this beautifully maintained 3 bedroom, 2 1/2 Bath home is an inviting choice for year-round living or a relaxing second home. Hardwood floors complement the open floor plan, creating a warm, welcoming flow throughout the main living areas. The spacious kitchen features a large center island, perfect for casual dining, gathering, and entertaining, while a cozy fireplace adds comfort and character to the living space. The first floor primary suite offers convenient main level living with a walk-in closet and private bath. Two additional bedrooms provide space for family, guests, or a home office, and abundant storage adds everyday practicality. Enjoy your morning coffee on the welcoming front porch or un

Nows your time to be part of life in Ocean Pines! Youll love the convenience of one-level living in this updated 3 bedroom 1.5 bath rancher in Sherwood Forest. Relax or entertain in your spacious sun-drenched family room that leads into an eat-in kitchen with updated appliances and enclosed laundry room. From the kitchen, step into the spacious screened-in porch and large partially fenced back yard overlooking trees. Ocean Pines offers an exceptional array of amenities including multiple pools, boat ramps, playgrounds, walking trails, a community center, and much more. All of this is only a few miles from Ocean City where youll find the Ocean Pines beach club with a pool, restaurant, locker rooms and other activities. Ocean Pines isnt just a neighborhood its a vibrant community with something for everyone. If youre looking for an investment, this property has been partially rented generating a steady income

Just like new! And a price reduction. Adorable and affordable! Built by American Homes, this charming, well-maintained 3-bedroom, 2-bath rancher is ideally located near the Swim & Racquet Club pool and White Horse Park. The bright, open floor plan features cathedral ceilings, a combined Living, kitchen and dining area, and a separate laundry room off the kitchen. Relax on the inviting front porch or enjoy the spacious rear deck. Recent updates include fresh paint, roof replacement with warranty (2019), newer HVAC, newer washer and dryer, and refrigerator, new microwave stove and dishwasher. Newly LVP flooring in the living room, dining room, and kitchen, new carpet in bedrooms. New bathroom flooring and raised toilets. Encapsulated crawlspace. Enjoy this low-maintenance home near the White Horse park, pool and recreation center

Discover a charming retreat in the desirable Ocean Pines. Huntington community. This beautifully maintained ranch-style home features an inviting open floor plan, perfect for both relaxation and entertaining. The living area seamlessly connects to the dining space, creating a warm atmosphere for gatherings. Enjoy the comfort of three well-appointed bedrooms and two full bathrooms, including a tub shower for unwinding after a long day. The kitchen is equipped with high-end electric appliances, including an oven/range and refrigerator, ensuring culinary delights are just a step away. Luxury vinyl plank flooring adds a touch of elegance throughout, while a cozy fireplace enhances the inviting ambiance. Front and rear decks are 40 ft x 12 ft totaling 960 sq ft of space. Newer roof, gutter w/gutter guards and windows. Step outside to enjoy community amenities, including pools, tennis courts, and scenic walking paths. With a prime location just minutes from the airport and a host of recreati

Price reduced x2*. Welcome to 542 Ocean Parkway in the highly desirable community of Ocean Pines a truly unique coastal retreat offering 4 bedrooms, 2 full bathrooms, and an unforgettable cabin-inspired design rarely found this close to the beach. Nestled among mature trees on a beautifully landscaped lot backing the golf course, this meticulously maintained home blends warmth, character, and modern upgrades. Step inside to soaring vaulted ceilings, dramatic walls of windows, rich wood finishes, and an open-concept layout filled with natural light. The spacious living area creates the perfect cozy-yet-grand atmosphere with elevated architectural detail throughout. The updated gourmet kitchen is designed for both everyday living and entertaining, featuring newer stainless steel appliances, a cooktop, built-in microwave drawer, updated cabinetry, generous prep space, and an oversized island overlooking the main living space. Both full bathrooms have been tastefully renovated with modern

Nestled in the charming community of White Horse Park, this delightful 2-bedroom, 1-bathroom home built in 2017 offers a wonderful blend of comfort, convenience, and modern living. This home features an open floor plan filled with natural light, creating a warm and welcoming atmosphere. One of the largest lots in the community, this property offers plenty of outdoor space and is backed by woods, providing added privacy and a peaceful natural setting. The home is also conveniently located directly across the street from the community pool, making it easy to enjoy one of the neighborhood's most popular amenities. A concrete driveway provides convenient off-street parking. Inside, the spacious kitchen is equipped with stainless steel appliances, including a built-in microwave, stove, dishwasher, and refrigerator, making meal preparation a breeze. The home also features a new washer and dryer for added convenience. Recent updates include a new HVAC system with a warranty, providing added c

Waterfront living at its best in ocean pines! Located in desirable Wood Duck Isle I, this impressive waterfront residence offers over 4,000 sq. Ft. of living space, 6 bedrooms, 3 full baths, and over 100 feet of bulkhead with direct access to the Bay. Boaters will appreciate the 55' x 3' dock and 8,000-lb. Boat lift with remote, installed in 2021. With multiple outdoor living spaces, a 3-season room, expansive decks, and a Crows Nest boasting panoramic water views, there is no shortage of places to relax or entertain. Inside, the spacious floor plan offers generous gathering areas, a Gourmet Kitchen, hardwood floors, upgraded carpeting, and abundant storage. The upstairs bonus area features a full wet bar, creating the perfect space for entertaining, game nights, or additional living space. The encapsulated crawlspace with dehumidifier provides added peace of mind. Major updates include the roof (2018), 8,000-lb. Boat lift with remote (2021), EV charger (2024), and downstairs HVAC (202

Major price adjustment of $20,000! Welcome home to this lovingly cared-for, one-owner home, designed by an interior decorator. This retreat nestled among the towering trees in the desirable North Gate of Ocean Pines one of the safest places to live in Maryland and just minutes from the beautiful beaches, dining, and entertainment of Ocean City, Maryland, Assateague and Rehoboth beaches. Medical facilities, schools, yacht club, and golf course nearby. Situated on a serene, private lot backs to Briarcrest Park, this charming 2-bedroom, 2-bath home also features a spacious loft that can easily be converted into a third bedroom, home office, or flex space to suit your needs. Filled with warmth and character, the great room showcases soaring cathedral ceilings accented by stunning exposed wood beams, unique moon-shaped architectural openings, and a cozy wood-burning stove that creates the perfect gathering place. The wood stove provides ambiance and warmth on cold winter nights as well as p

MUST-SEE beach-style home in the highly-acclaimed community of Ocean Pines! This 3-bedroom/2.5-bathroom, fully-furnished, turnkey house, with select items excluded, situated on a 0.20-acre serene, natural setting, with both an indoor and outdoor staircase to access inside. Within the main door, a foyer entrance allows for beach gear and other storage, before heading up the stairs to the elegant, open living-space. Here, LVP flooring guides you between the amply-sized modern kitchen, complete with quartz countertops and stainless-steel appliances, the cozy living-room, and the spacious dining-area. From here, the living and entertainment space continues, with sliding-glass doors giving the invitation to enjoy the MASSIVE screened-in porch (also accessed by a separate door from the kitchen). Family and friends can then transition into a full nature-immersion, as the opposite screen-door gives way to the large deck, easily serving as the party center, or a peaceful spot for coffee and bir

Enjoy waterfront living in this inviting 3-bedroom, 3-bath canal-front home located just a short distance from the open bay. Designed to make the most of its waterfront setting, the home features a spacious screened porch, upper-level deck, and patio with built-in seating, providing multiple places to relax, entertain, and enjoy the views. Inside, the kitchen offers tile flooring and pantry storage and opens to the dining area for easy everyday living. The upper level features a bedroom, full bath, and versatile loft space. Additional highlights include a newer roof installed in 2017, HVAC system replaced in 2018, water heater installed in 2024, and partial furnishings included. Whether you are searching for a primary residence or waterfront getaway, this home offers comfort, flexibility, and an ideal coastal lifestyle

This charming ranch-style home, built in 1963, offers a perfect blend of comfort and investment potential. With 1,360 square feet living space. This property features three bedrooms and one full bathroom with a tub shower combo. The kitchen is has, an electric wall oven, electric cook top stove, microwave. The home sits on a cleared lot of 0.22 acres. A spacious front deck for you to enjoy morning coffee. The detached two-car garage offers valuable storage and parking options. First time home buyers and Investors welcome. With its inviting charm and investment appeal, this property is a wonderful opportunity waiting to be seized

Quality Craftsmanship meets exceptional care in this beautifully maintained home, built by Piney Island Builders. Neatly nestled on a large private lot backing to peaceful woods in the heart of Ocean Pines, this home offers the perfect blend of comfort, privacy, and timeless appeal. Designed for easy living, the home features a spacious first-floor primary suite, providing convenience and flexibility for everyday life. Recent updates include a newer roof, composite decking, and updated kitchen appliances, allowing you to move in with confidence. Step outside and enjoy the beautifully landscaped Backyard, where you'll find a charming treehouse and plenty of space to relax, entertain, or simply take in the serene wooded setting. Recently updated crawl space encapsulation and dehumidifier ensure peace of mind. A large garage offers ample room for vehicles, storage, and hobbies. Two more outbuildings, a large shed, and an adorable greenhouse complete the yard. This exceptional home showcas

Looking for a permanent home or a vacation get away? This is it! Offering both convenience and relaxation this home has one level living with an open floor plan, vaulted ceilings, a combined dining and kitchen area, a gas fireplace for cozy evenings and a screen porch to enjoy through all the seasons. This coastal contemporary has three bedrooms and two full baths. The luxury vinyl plank flooring, vanity lights, fixtures, ceiling fans and appliances are only about a year old. Ocean Pines has all the amenities you could ever hope for: volleyball, parks, a marina, a golf course, both indoor and outdoor pools, walking trails and a variety of clubs and activities. Easy access to nearby beaches and attractions come fall in love with the magic of Ocean Pines living

Live where every day can feel like vacation! Welcome to 44 Birdnest Drive, a turnkey 3-bedroom, 2-bath home tucked into a quiet, wooded setting in Ocean Pinesoffering the perfect mix of privacy, recreation, and coastal living just minutes from the beach. Inside, the open floor plan and vaulted ceilings create a bright, spacious feel, with generously sized bedrooms and plenty of room to settle in. The kitchen features granite countertops and stainless steel appliances. Both bathrooms have updated vanities, with a custom tiled shower in the primary bath and tiled tub surround in the guest bath. Convenient laundry and a new roof in 2024 add to the easy, low-maintenance lifestyle. Step outside to a concrete patio and a backyard that feels like your own little retreat. Surrounded by trees, theres room to grill, gather around a fire pit, or simply relax and enjoy the peaceful settingit has that camping-at-the-shore feel without leaving home. And just beyond the backyard is Huntington Park, w

This charming property in Ocean Pines, MD features 3 bedrooms and 2 bathrooms, offering comfortable living in a peaceful setting

This new construction property is a customized version of the popular Wahoo model, with groundbreaking scheduled to start in approximately 30 days. Buyers who secure this home early have a rare window of opportunity to select the custom interior finishes and make this home uniquely theirs. Core Property Overview, Floor Plan: Customized Wahoo/3 Model, Bedrooms: 3 spacious bedrooms, Bathrooms: 2 full bathrooms, Garage: Attached 2-car garage, Premium Interior & Gourmet Kitchen Custom Upscale Kitchen: Outfitted with high-end stainless steel appliances. Gas Cooking: Features a premium gas range for culinary precision. Gas Fireplace: Serves as a cozy, ambient centerpiece in the main living area. Primary Suite: Features an expansive, large primary bath with detailed custom showers. Outdoor Living Spaces Screened Porch: Built for bug-free relaxation and comfortable outdoor lounging. Outside Deck: Perfect for grilling, entertaining, and enjoying the backyard views. High-Efficiency & Structural

Enjoy waterfront living with beautiful views overlooking a wide canal and quick, easy boating access to open water! Located on a quiet cul-de-sac street in the highly desirable, amenity-filled community of Ocean Pines, this original-owner home has never been used as a rental. Offering 3 bedrooms, 2 baths and 1,852 square feet of comfortable living space, the home features a kitchen with granite countertops and stainless steel appliances, many of which have been replaced over the past few years. The first floor includes a bedroom with direct access to a full bath, while the sunroom provides a wonderful spot to relax and enjoy the waterfront setting. Step outside to the rear deck and take in the peaceful water views, or head down to your private boat dock and enjoy the convenience of having your boat right in your own backyard. An attached workshop provides plenty of useful space for boating equipment, bikes, beach gear, tools and more. The roof is approximately eight years old, adding a

Your Eastern Shore getaway is waiting! Located in the gated White Horse Park community in Berlin, this furnished 1-bedroom, 1-bath home offers an easy, low-maintenance place to enjoy everything the area has to offer. The open floor plan features an eat-in kitchen, comfortable living and dining areas, and a sitting room that provides additional space to relax and unwind. With furnishings included as shown, you can spend less time getting settled and more time enjoying your new coastal retreat. White Horse Park is packed with amenities, including an outdoor pool, clubhouse, basketball courts, playground, walking paths, picnic areas, gated security and common grounds. Water lovers will appreciate access to the community marina, boat ramp, pier and dock, along with bay and water privileges. HOA services also include lawn maintenance, water, sewer, trash, road maintenance and more, helping make ownership easy whether you're here for a weekend escape or an extended stay. Located in Berlin an

Featuring over $80,000 in brand-new capital upgradesincluding a brand-new bulkhead, new dock, new roof, and newer dual zone HVAC system with full ductworkthis premier Wood Duck Isle estate offers immediate boating access with absolute structural peace of mind. Perfectly positioned near the end of a canal with beautiful views stretching across Manklin Creek, this spacious 4-bedroom, 2.5-bath waterfront home offers the ideal blend of comfort, quality, and coastal living. Meticulously maintained and thoughtfully updated, the current owners have invested extensively in the home's major systems and waterfront features. Designed for both everyday living and entertainment, the first floor features a spectacular waterfront primary suite with a beautifully updated bathroom and an oversized walk-in closet. A dramatic two-sided brick gas fireplace creates a warm focal point, shared between the primary bedroom and the dining room. The main level also includes a spacious waterfront great room with

Brand new construction now! This impressive home offers over 3,400 square feet of living space with 5 bedrooms, 3.5 baths, and a bonus room, providing exceptional flexibility for todays lifestyle. Located on a quiet cul-de-sac in Triple Crown Estates, a community known for its larger lot sizes, this property features a generous 125 x 100 homesite. The home offers two primary suitesone on each level. The first-floor primary suite features a beautifully tiled shower, while all full bathrooms are equipped with double-bowl vanities. The stunning kitchen showcases quartz countertops and stainless steel appliances and flows seamlessly into the dining area, which opens to a screened porch and deck, perfect for indoor-outdoor living. The family room is warm and inviting with a linear electric fireplace and a beam-accented vaulted ceiling. Additional highlights include 9 ceilings on the first floor, LVP flooring throughout the first floor and staircase, a dedicated laundry room, an 80-gallon ho