72 properties for sale in Woodbury Acres

Custom Home with In-Ground Salt Water Pool, Private Backyard & Detached, Heated and Cooled Studio/Office in Greenwood Community. Discover the distinctive charm of this custom-built home in the sought-after Greenwood Community of Grasonville. Providing four bedrooms, and three-and-a-half. Bathrooms, this home combines thoughtful craftsmanship, architectural character, and inviting indoor-outdoor living. Step inside to a light-filled, open layout highlighted by a dramatic two-story family room, soaring ceilings, expansive windows, and an impressive stone fireplace. Hardwood floors, crown molding, decorative leaded-glass windows, rounded wall corners, and distinctive lighting add character throughout. The spacious kitchen features granite counter tops, a generous center island, under-cabinet lighting, and stainless steel appliances, including a double-oven range and beverage cooler. The adjoining dining room overlooks the backyard, creating a welcoming setting for everyday meals and enter

Open daily by appt. Space, comfort & location! (NOTE: Pictures with furniture are virtually staged). You really can have it all! Welcome to 336 Timber Ln in Grasonville! This well-maintained two story colonial offers 4 bedrooms, 2.5 bathrooms, and a 2 car garage, all just minutes from Kent Island and the Chesapeake Bay Bridge. An ideal location for an easy commute while enjoying everything the Eastern Shore has to offer! Inside, youll find a spacious, inviting layout with a well sized kitchen featuring a breakfast bar that opens to the family room and sunroom. Picture cozy evenings by the fireplace as the temperatures drop! The sunroom adds even more flexible living space, perfect for a breakfast nook, additional seating, or simply enjoying the natural light. Upstairs, the spacious primary suite features a large walk-in closet and private bath with dual sinks, a soaking tub, and a separate water closet. Three additional bedrooms, a full hall bath, and multiple closets provide plenty of

Desirably located in Queen Anne Woods just off Bennett Point Road, this impressive brick-front colonial offers a rare combination of privacy, space, and convenience. Significant updates include a brand-new roof (2026), HVAC replacement (2021), new distribution box for septic system (2026), reverse osmosis system installed (2026), updated kitchen and bathrooms, updated windows, doors and siding, fresh interior paint, modern light fixtures, and a Trex deck. Set on a beautiful 1-acre wooded homesite, the home blends timeless appeal with extensive updates and exceptional pride of ownership. Meticulously maintained and move-in ready, it offers a wonderful balance of comfort and flexibility, with no homeowners association and room to enjoy the property on your own terms. Inside, gleaming hardwood floors, fresh interior paint, modern light fixtures, and beautiful interior wood shutters throughout create a warm and refined atmosphere. The welcoming foyer opens to a formal living room or den an

PRESQUILE MANOR HOUSE An extraordinary waterfront estate steeped in history, architectural distinction, and timeless elegance. Magnificently positioned along the Wye River with breathtaking panoramic views and coveted western exposure, this distinguished circa-1800 manor house offers an exceptional combination of historic character, refined luxury, and unparalleled waterfront living. Originally part of the historic Lloyd family holdings, the 10.48-acre estate has been meticulously renovated by renowned Peter Zimmerman Architects and West & Callahan Construction, reflecting an extraordinary commitment to preserving its architectural heritage while incorporating the finest modern appointments. The magnificent 7BR/6FB/3HB manor house showcases exquisite craftsmanship throughout, with exceptional millwork, beautifully proportioned rooms, soaring ceilings, rich hardwood floors, elegant fireplaces, and graceful architectural details. Expansive windows fill the interiors with natural light wh

A Private Wye River Sanctuary! Some properties offer a home. Others offer a lifestyle. This exceptional Wye River retreat offers both. Set along one of the Eastern Shores most beautiful waterways, this beautifully updated ranch home is an invitation to slow down, entertain effortlessly, and enjoy waterfront living at its finest. From morning coffee on the screened porch to sunset swims in the Gunite pool, every day here feels like a getaway. The light-filled, open interior provides an inviting backdrop for relaxed gatherings and everyday living, while a versatile additional living area offers the flexibility for an in-law suite, private home office, game room, or guest retreat. The serene primary bedroom enjoys direct access to the screened porch, creating a private connection to the tranquil waterfront setting. The extensive improvements provide peace of mind while enhancing the home's appeal, including an architectural roof, vinyl siding, gutters, sophisticated hybrid heat pump/propa

Welcome to Perrys Retreat, where spacious living meets modern comfort and Eastern Shore charm! *. Built in 2023, this pristine Ryan Homes Lehigh model offers the. *largest floor plan in the community*, featuring over 3,000 square feet of beautifully designed living space, five bedrooms, two-and-a-half bathrooms, and an exceptional open-concept layout. The heart of this home is its expansive main living area, thoughtfully designed for both everyday comfort and effortless entertaining. The open floor plan seamlessly connects the kitchen, dining, and gathering spaces, creating a bright and inviting atmosphere. The spacious kitchen features an oversized center island that serves as the perfect gathering spot for casual meals, entertaining guests, or simply enjoying time together. With generous room to spread out, this main level is truly an entertainers dream! Adding to the home's versatility is a main-level bedroom, ideal for guests or multigenerational living, along with a separate flex

Welcome home to this beautifully maintained and fully updated 3-bedroom home, just 8 years young! Featuring like-new systems and roof, this home offers modern comfort and peace of mind. A 4-foot bump-out provides additional living space, while the upgraded kitchen boasts stainless steel appliances and sliding glass doors leading to a spacious 12x20 composite deckperfect for entertaining. Enjoy outdoor living with an above-ground pool, fully fenced backyard with white vinyl privacy fencing, and a crushed stone patio that leads to a cozy fire pit area. The long gravel driveway and oversized two-car garage offer ample parking and storage. Inside, youll find a spacious primary bedroom with a private full bath, plus an additional family room on the lower level with a convenient half bathideal for extra living space, guests, or a home office. Perfectly maintained from the front door throughout, this hidden gem is conveniently located near Route 50, making it an excellent choice for commuters

Waterfront weekends on the Chester River, for a fraction of what a waterfront house costs. Lot 46F on Zuma Beach in Beach Harbor Camper Cooperative comes with a Forest River Silverback fifth-wheel set up under mature shade trees, so your summer afternoons stay cool. Inside: 1 bedroom and 1 bath. Outside: Outside, the setup is already done for you: a brick paver patio with a built-in fire pit, string lights overhead, a privacy screen, built steps to the entry, a storage shed, and a gravel pad for parking, all under mature shade trees. Your co-op membership puts you on Jackson Creek and the Chester River, with a community boat ramp, pier, private beach, pool, hot tub, clubhouse, tennis, basketball, and shuffleboard. Launch the boat in the morning, fish the afternoon, and end the night around your own fire pit. Buy this fall and use the off-season to get it set up, so you're ready the day the season opens. Schedule your private showing now. Since this is a co-op campground financing is no

Some homes are simply places to live. This is a lifestyle. Welcome to 228 Prospect Bay Dr W, an exceptionally maintained and thoughtfully updated home where beautiful water views, resort-style outdoor living, and the coveted Prospect Bay community come together in one unforgettable property. From the moment you arrive, the setting makes an impression. Mature landscaping, a gracious exterior and glimpses of the water create a sense of arrival that feels distinctly Eastern Shore. Step inside and youll quickly see that this home has been meticulously cared for and intentionally improved, blending timeless coastal character with sophisticated, modern updates. Hardwood floors extend throughout both levels, while custom trim work, designer wall treatments, updated lighting and carefully selected finishes give each space its own personality. The beautifully updated kitchen is designed for both everyday living and entertaining, featuring new countertops and backsplash, an enhanced island with

Spectacular waterfront views of a lifetime! Luxury and the Coveted'BIG SIX' Rare to Come on the Market. Full Water Access. Deeded 40' Deep Water Boat Slip. Attached Garage. 3 Waterside Decks. Experience the epitome of Luxury Living in this exquisite waterfront townhouse nestled in the prestigious Oyster Cove community. This stunning 3-bedroom, 3.5-bath plus a spacious bonus room with it's own private walk out deck gives you that flexible space for a bedroom suite, a home office, or a game room! An open floor plan on the main level is adorned with rich hickory wood floors, recessed lighting, the ambiance of a wood burning fireplace, and a gourmet kitchen featuring upgraded countertops and new stainless steel appliances. Panoramic Bay Views from your open family room, dining room and waterside deck! Indulge in the primary suite with Breathtaking Bay Views, a walk-in closet, and a spa-like bathroom complete with a whirlpool tub and walk-in shower. Step outside to your private oasis, where

Tenant occupied, income producing two unit property in downtown Grasonville now available! The front house (B) rents for $1200 per month to a month to month tenant. The house (B) has 3 bedrooms and 2 baths. The 2 bed 1 bath second floor garage apt rents for $1378 per month to month to month tenants. All tenant spay their own utilities

Reduced $20,000! Enjoy carefree WATERFRONT living in this Beautifully UPDATED Condo in the sought-after Oyster Cove Community at the KENT NARROWS! Offering 3 bedrooms and 2 full bathrooms, this light-filled, one-level residence features an open floor plan designed for easy living and entertaining! Stunning wide plank wood flooring flows throughout the main living areas, complemented by newer stone countertops, fresh interior custom paint throughout and NEW carpet in the bedrooms. The spacious living and dining areas open to a Waterfront Deck where you can relax and enjoy breathtaking Sunsets over Eastern Bay and The Narrows. The thoughtfully designed layout offers generous bedroom sizes and two updated baths. Recent exterior improvements include new siding and new windows. Oyster Cove residents enjoy an exceptional Waterfront lifestyle with access to two Marinas, Swimming Pool, two Tennis Courts, a walking/jogging path and a Clubhouse with a fitness room. Conveniently located within wa

Welcome to Oyster Cove Live the Oyster Cove lifestyle! Welcome to a beautifully maintained townhome in Oyster Cove, a gated waterfront community offering the perfect blend of elegance, convenience, and carefree living. Here, the grounds are maintained for you, giving you more time to enjoy the lifestyle youve worked for. Residents can take advantage of the community pool, waterfront surroundings, and peaceful, beautifully landscaped setting. Enjoy the best of Grasonville right outside your doorrestaurants, shopping, marinas, entertainment, and everyday conveniences are all just minutes away and easily accessible by car, bike, or even a leisurely walk. Whether youre looking for a full-time residence, a weekend retreat, or a low-maintenance home where you can simply lock the door and go, Oyster Cove offers an exceptional setting. This is more than a townhomeits a lifestyle. Come experience the charm, sophistication, and relaxed waterfront atmosphere of one of the areas most desirable com

Recent price reduction! Step into a charming piece of history with this stunning Colonial home, built in 1879, nestled in the desirable Queenstown neighborhood, water community and GOLF. Spanning 1,920 square feet, this residence seamlessly blends classic elegance with modern comforts, making it the perfect sanctuary for today's discerning buyer. As you enter, you'll be greeted by exquisite details such as crown moldings and chair railings that evoke a sense of timeless sophistication. The gourmet kitchen is a chef's dream, featuring upgraded countertops and essential appliances, including a refrigerator, stove, dishwasher, and icemaker, ensuring every culinary endeavor is a delight. The inviting dining area is perfect for hosting gatherings, while the cozy living room, complete with a charming fireplace, sets the stage for intimate evenings. This home boasts three spacious bedrooms, including a primary suite with an en-suite bath, providing a private retreat. Outside, enjoy the sereni

Waterfront living with lifestyle, location and luxury! Located at the mouth of the Chester River, this home is in the perfect spot for days on the Bay, boat rides to Kent Narrows restaurants, golf at Queenstown and shopping the outlets, all just minutes from the Bay Bridge. This beautifully updated home delivers the best of Eastern Shore living with 259' of waterfront, a community pier, a school district ranked #7 among the Best School Districts in Maryland, and easy access to Annapolis and beyond. The deeded slip (with boat and PWC lifts) makes life on the water effortless. The water views and natural wetlands of Winchester Creek offer sunsets, privacy and abundant birdlife. A mowed path leads to water's edge for kayak and paddleboard launches. This home features more than 4,400 square feet on three finished levels, with west-facing water views from expansive windows that fill the home with natural light. The two-story family room features a rebuilt luxury fireplace with custom trim w

Absolutely wonderful rancher in belle point farm! 3 large Bedrooms, 2 full Baths, a screened Porch, Patio, Basement, 2-car Garage and more! The Sellers have already taken care of the'big ticket' items. The interior was just repainted in a clean, neutral palette so you're all set to move in and enjoy the holidays in your new home! Open spaces and banks of windows make for a bright, airy, and inviting vibe. The floor plan is practical and spacious, featuring both a comfortable living room and a cozy family room centered around a wood stove and wood-burning fireplace with a raised brick hearth and surround. The screened porch is just off the family room and will quickly become one of your favorite spots. The kitchen is equipped with upgraded counters, wood cabinetry, a central island with a breakfast bar, and a breakfast room with access to the patio area. A separate dining area and laundry/mud room round out this main level. Expansion and storage are not an issue here between the unfinis

From the moment you turn onto winding Carmichael Road and cross the bridge onto Wye Island, the pace begins to slow. Of the islands approximately 2,800 acres, only about 350 are privately owned. The State of Maryland through the Maryland Park Service owns and manages the rest. The Point is among the islands handful of private properties, distinguished by almost six acres and more than 1,200 feet of elevated waterfront, one of the largest private shorelines on Wye Island, with over half riprapped. Set at the end of a private drive, this exceptional estate offers a rare sense of privacy amid the islands pristine, unspoiled lands. The main residence is distinctive in both design and setting, with a playful modern aesthetic, soaring ceilings reaching nearly 18 feet, and an open floor plan oriented toward the water. Two bedroom suites occupy the main level, each with an ensuite bath and its own exceptional outlook, one overlooking the Wye River, the other facing a private cove. Upstairs, tw

Discover the perfect blend of modern elegance and comfort in this stunning Colonial-style home located in the desirable Perry's Retreat. Built in 2024, this residence boasts a pristine condition and an array of features designed to enhance your lifestyle. Step inside to find an inviting open floor plan that seamlessly connects the gourmet kitchen, dining area, and family room, creating an ideal space for entertaining and everyday living. The kitchen is a chef's dream, equipped with upgraded countertops, a double oven, built-in microwave, and ample pantry space. With four generous bedrooms and 2.5 baths, this home offers plenty of space for relaxation and privacy. The upper floor laundry adds convenience to your daily routine, while the elegant luxury vinyl plank flooring and tasteful window treatments throughout elevate the aesthetic. Outside, the property features a well-maintained exterior with sidewalks and a concrete driveway leading to a two-car attached garage, ensuring ample par

Welcome home to 120 Pathfinder Circle in Perry's Retreat! Built in 2023 and meticulously maintained, this 4. Bedroom, 3.5 bath home offers approximately 3,010 sf of beautify designed living space, where thoughtful upgrades, custom touches, and everyday functionality come together. From the moment you walk in, the attention to detail is impossible to miss. The main level showcases a stunning three-sided fireplace topped with a custom walnut mantel. An eye catching centerpiece that makes the living space feel warm, inviting, and distinctly your own. The kitchen is made for gathering, cooking and entertaining, featuring two ovens and custom. Made pendant lighting that adds both function and personality. Throughout the home, an upgraded Craftsman trim package recessed lighting, luxury vinyl plank flooring, and ceiling fans in every room create a polished, comfortable feel. With Ethernet wiring throughout, this home is ready for everything from work from home days to movie nights and stream

This is not your average rancher! Welcome to 119-A Rebel Road in Grasonville, featuring a hard-to-find detached two-car garage with A/C and room for a woodstove. This renovated 3-bedroom, 2-bath home sits on nearly half an acre with space for boat storage. Pictures coming soon! Enjoy a huge eat-in kitchen with brand-new stainless appliances, XL sink, new fixtures, lighting and flooring. Fresh paint, new carpet, upgraded baths, and an owners suite with private bath and walk-in closet. Peaceful rural setting near waterfront parks, beaches, trails, kayaking, boating, restaurants and shopping

Welcome to 224 Wye Knot Court, a charming 3-bedroom, 2-bath home situated on a spacious lot in the peaceful Wye Knot Farms community. Step inside to a bright and inviting layout filled with natural light and comfortable, functional living spaces. This well-maintained home offers the perfect opportunity to enjoy the relaxed lifestyle of Marylands Eastern Shore. Wye Knot Farms is known for its quiet setting, generous lots, and welcoming neighborhood feel, while still providing convenient access to Route 50, shopping, dining, and the beautiful Wye River. Whether youre purchasing your first home, looking to downsize, or simply searching for a little more space and tranquility, 224 Wye Knot Court is a must-see! Professional photographs coming soon!

Welcome home to this beautifully updated contemporary offering water views, flexible living space, and a community pier practically in your backyard! With 3 bedrooms and 2 full baths, this home features a primary bedroom on each level, making the layout ideal for a variety of living arrangements. The heart of the home is the gourmet kitchen, complete with granite countertops, a stylish glass backsplash, stainless steel appliances, a center island, breakfast bar, and plenty of space for a kitchen table. Just beyond, the dramatic two-story living room features a cozy gas fireplace, refinished hardwood floors, and a beautiful stained-glass window that adds character and charm. Enjoy the convenience of a main-level primary bedroom, while upstairs, the entire second floor is dedicated to an expansive primary suite with beautiful views of Greenwood Creek. Outdoor living is just as inviting. Relax on the screened porch, large deck, enjoy the fenced rear yard, or head just steps away to the co

Come experience the relaxed, resort-style lifestyle of Prospect Bay, one of the Eastern Shores most desirable golf course communities. Spend your days enjoying the 18-hole championship golf course, relaxing by the community pool, playing tennis or pickleball, or heading out on the water. Prospect Bay offers a community boat ramp and marina with access to navigable waters leading to Eastern Bay, putting St. Michaels, Kent Narrows, Annapolis, and other Chesapeake Bay destinations within reach by boat. Meet friends for dinner or drinks at the clubhouse restaurant, visit the pro shop, or take part in the communitys active social calendar. Ideally located on Marylands Eastern Shore, Prospect Bay offers a wonderful combination of golf, boating, recreation, and communityall just minutes from the Chesapeake Bay Bridge, approximately 25 minutes from Annapolis and one hour from BWI Airport. Set within this exceptional community, this beautiful custom home enjoys a prime setting overlooking the 1

Spectacular Waterfront Retreat on almost 7 Acres in Exclusive Bennett Point! Welcome to your private paradise on the shores of serene Greenwood Creek! This extraordinary waterfront estate offers almost 7 acres of pure tranquility and luxury, surrounded by water on two sides for a true feeling of seclusion and peace. Your deep-water private pier is a boaters dream complete with 3 boat lifts and 2 jet-ski lifts ($150k value just in lifts alone) perfect for crabbing, fishing, or setting out for a sunset cruise. The homes Royal Blue Terracotta roof and accents make a bold architectural statement, while the full wrap-around deck ensures youll never miss a moment of the breathtaking waterfront views. Step inside and be transported to a stunning waterfront chalet (2x6 construction), where soaring ceilings, skylights, and warm wood accents create a cozy yet grand, open atmosphere. The nearly 3,000 sq. Ft. of living space includes a magnificent 35 x 17 great room anchored by a floor-to-ceiling

Seasonal living only! April through November! Great camper cooperative in the Kent Narrows! Seasonal living only, from april through november! Enjoy a fantastic vacation getaway and the relaxed Eastern Shore lifestyle. This updated park model camper is ready for you to enjoy life at Beach Harbor. It is fully furnished, except for the large grey sectional. The camper sleeps at least 4, and depending on the sofas, it can accommodate 6-8 people. New sunroom, new roof, new siding, updated flooring, updated heat and A/C, new windows, extra parking, and golf cart conveys with full-price offer. The golf cart is in great condition and is newer. For park purposes, it is considered a 2-bedroom. Some photos are lighting-enhanced with AI. Must make an appointment to view. Owner to arrange for showings. Parking for showings is in the guest parking outside the gate. Cash or personal loan only. No mortgage financing available, cash or personal loan onlyu. Vacation rentals are allowed, but ONLY self-m

Grasonville. Property is zoned GVC, this gives you opportunity to own your own home and business. Well maintained property and home located on a corner lot with garage and extra storage sheds. Plenty of room for parking, open floor plan featuring 3 bedrooms 2 baths with luxury vinyl flooring with wonderful kitchen with upgraded commercial size refrigerator/freezer. The decks make it nice for outside entertaining with custom retractable awning and screen/shades

Welcome to 125 Forest Road in Grasonville! This beautifully fully remodeled home is move-in ready and offers modern updates throughout. The brand-new kitchen features fresh finishes and updated amenities, while the newly renovated bathrooms add style and functionality. Major improvements include a new HVAC system, new roof, new well, and refinished floors, providing both peace of mind and lasting value. Tucked away on a quiet cul-de-sac, this home offers a peaceful setting while remaining conveniently located near Route 50 for an easy commute and access to shopping, dining, and recreation. Located in a desirable area with access to good schools, this extensively updated home is an excellent opportunity for buyers looking for comfort, convenience, and a truly turn-key property

Highly motived sellers enjoyed Prospect Bay and want you to as well-they just reduced again making it super attractive. Discover the charm of this beautifully renovated split-level home in the desirable Prospect Bay community. With 4 spacious bedrooms and 3 full baths, this residence boasts an inviting interior featuring upgraded countertops, LVP floors, and cozy exposed beams. The heart of the home is the combination kitchen/dining area, perfect for gatherings that can flow outside to the new expanded deck. With one bedroom, full bath and living room on lower level it could be the perfect in-law suite or college student apartment. Enjoy the serene 1.22-acre corner lot with firepit, trees perfect for hammock, backing to mature trees, offering a peaceful views. The community amenities include a pool, golf course, marina, community pool, tennis & pickleball courts and playgrounds, fostering a vibrant neighborhood spirit. Enjoy easy access to the Prospect Bay sanctuary for boating and fis

Welcome to 452 Timber Lane in Grasonville! This inviting 3-bedroom, 2-bath home offers comfortable living spaces along with a unique converted garage that provides additional finished space perfect for entertaining, relaxing, a home gym, game room, or whatever best fits your lifestyle. Step outside and enjoy the nice backyard, offering plenty of room for outdoor entertaining, gatherings, play, or simply relaxing and enjoying your own outdoor space. With its flexible layout, additional finished space, and inviting yard, this home offers plenty of opportunity to make it your own. Come see all that 452 Timber Lane has to offer!

New price a great opportunity in prospect bay! Offering approximately 2,850 square feet of living space, this contemporary presents an opportunity to enjoy the Prospect Bay lifestyle at an attractive price point. Available for the first time since 1999, this well-loved home is ready for its next chapter. The spacious family room features a brick fireplace, cathedral ceiling and triple sliders opening to the deck and backyard. The kitchen offers lovely cabinetry, generous counter and storage space, and plenty of room for casual dining. Two bedrooms are conveniently located on the main level, along with a separate dining room and dedicated mudroom with laundry. Upstairs, the spacious primary suite offers privacy, while a loft overlooking the family room provides flexible space for a home office, sitting area, or additional living area. Oversized 2-car garage, plus deck overlooking the backyard. Located in Prospect Bay Golf & Country Club, where residents enjoy golf, swimming pool, tennis