Sleepy Hollow Real Estate

Sleepy Hollow Real Estate

Welcome to Sleepy Hollow, a picturesque subdivision nestled in the heart of the United States, where charm meets tranquility. This idyllic community is renowned for its serene atmosphere and lush landscapes, making it the perfect retreat for families, retirees, and anyone seeking a peaceful lifestyle.

Sleepy Hollow boasts a diverse array of beautifully designed homes, each reflecting a unique architectural style that harmonizes with the natural surroundings. From charming single-family residences to spacious townhomes, there’s a perfect fit for everyone. The tree-lined streets invite leisurely strolls, while manicured lawns and vibrant gardens create a welcoming ambiance.

One of the standout features of Sleepy Hollow is its strong sense of community. Neighbors often gather for seasonal events, block parties, and farmer's markets, fostering connections that turn acquaintances into lifelong friends. Families will appreciate the top-rated schools nearby, ensuring that children receive a quality education in a nurturing environment.

For outdoor enthusiasts, Sleepy Hollow offers an abundance of recreational opportunities. Explore the nearby parks, where you can enjoy hiking trails, picnic areas, and playgrounds, or take advantage of the community’s well-maintained walking paths that wind through the picturesque landscape.

Conveniently located just a short drive from urban amenities, residents can easily access shopping, dining, and entertainment options while still enjoying the peace and quiet of suburban living.

Discover the charm of Sleepy Hollow, where your dream home awaits amidst a friendly community and breathtaking surroundings. Come experience the magic of this enchanting subdivision and make it your forever home!

Newest Listings in Sleepy Hollow

3021 Sleepy Hollow Rd, Falls Church
$1,799,000
6 Beds ⋅ 7 Baths
Welcome to this extraordinary over 6,000 sq ft new construction residence situated on a prime half-acre lot in Falls Church, featuring a striking contemporary design. The light-filled main level offers a dedicated home office/main level bedroom, formal dining room, mudroom off the 2-car garage, and a open-concept chef’s kitchen with a center island and walk-in pantry that flows into the breakfast room and family room featuring a fireplace and wall of glass overlooking the rear grounds. Upstairs, the primary suite serves as a true sanctuary with a private veranda, dual walk-in closets, and a spa-inspired ensuite bath, alongside three additional bedrooms all with private baths and walk in closets, and a convenient upper-level laundry room. Completing this exceptional home, the fully finished lower level features a massive rec room complete with wet bar, fireplace and walk out stairs, exercise room, spacious media room, and a private 5th bedroom with a full bath ideal for guests or an au pair. All just minutes from major commute routes convenient to DC and surrounding areas. 

3021 Sleepy Hollow Rd, Falls Church

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

247 Dewdrop Ln, Hedgesville
$269,900
2 Beds ⋅ 1 Baths
Discover the charm of this newly constructed ranch-style home nestled in the serene Sleepy Hollow community. Completed in 2026, this delightful residence features two spacious bedrooms and a beautifully designed full bathroom, all set on a generous 1.74-acre lot. The exterior boasts durable vinyl siding, ensuring both style and longevity. Embrace the tranquility of nature with easy access to nearby lakes, perfect for leisurely afternoons by the water. The inviting interior showcases a blend of cozy carpet and sleek vinyl flooring, creating a warm atmosphere throughout. With ample driveway parking and a thoughtfully designed layout, this home is ideal for those seeking comfort and convenience. Enjoy the peaceful surroundings while being just a stone's throw away from recreational opportunities. This property is not just a house; it's a place to create lasting memories. Don't miss your chance to make it your own!

247 Dewdrop Ln, Hedgesville

Listing courtesy of Brawner & Associates. Contact:

28061 Cross Creek Dr, Salisbury
$385,000
3 Beds ⋅ 2 Baths
Welcome to 28061 Cross Creek Drive, a beautifully maintained 3-bedroom, 2-bath rancher offering the convenience of single-level living in the desirable Sleepy Hollow community on Salisbury's west side! Situated on a spacious lot in an established neighborhood, this inviting home combines comfortable living, thoughtful upgrades, and a fantastic location. Step inside and immediately appreciate the gleaming hardwood floors that flow throughout the main living areas. The spacious, open-concept great room features soaring vaulted ceilings, a cozy gas fireplace, recessed lighting, a ceiling fan, and an abundance of natural light, creating the perfect atmosphere for both everyday living and entertaining. The beautifully appointed gourmet kitchen is sure to impress with granite countertops, a custom tile backsplash, crown moulding, stainless steel appliances, and a center island overlooking the great room and dining area. An additional beverage refrigerator provides the perfect place to keep your favorite wine and refreshments chilled. Just off the main entryway, a versatile bedroom featuring elegant wainscoting, a ceiling fan, and a closet offers endless possibilities as a guest bedroom, home office, or formal dining room. The spacious primary suite provides a comfortable retreat, complete with a generous en-suite bathroom featuring a double vanity, separate soaking tub, and custom walk-in tile shower. Step outside and enjoy your own backyard retreat! The generously sized yard offers plenty of room for outdoor activities, gardening, or simply relaxing. Entertain family and friends on the rear deck, unwind in the charming stone garden area surrounded by attractive landscaping, or enjoy the additional storage provided by the backyard shed. The finished garage is another standout feature, complete with drywalled interior walls, attractive epoxy flooring, an insulated garage door, and an automatic opener. Additional conveniences include gas heating, electric hot water, and an electric range. Located in the sought-after Sleepy Hollow community, residents enjoy an attractive neighborhood setting with sidewalks, streetlights, and convenient access to everything Salisbury has to offer. Shopping, dining, schools, medical facilities, Salisbury University, and TidalHealth Peninsula Regional are all within easy reach. Outdoor enthusiasts will appreciate the proximity to Pemberton Historical Park and its scenic walking trails. Commuters and beach lovers alike will appreciate the convenient access to Route 50, providing an easy drive east toward Ocean City and Maryland's beautiful beaches or west toward Cambridge, Annapolis, and the Chesapeake Bay. Whether you're looking for your first home, downsizing to convenient one-level living, or simply searching for a beautiful property in a well-established community, 28061 Cross Creek Drive has so much to offer. Schedule your private showing today and discover why Sleepy Hollow is such a wonderful place to call home!

28061 Cross Creek Dr, Salisbury

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact:

480 Maverick Trl, Hedgesville
$175,900
2 Beds ⋅ 1 Baths
Welcome home to your newly renovated chalet near the back of Sleepy Hollow featuring tons of privacy and wildlife! This 2 bed, 1 bath has vaulted ceilings and offers tons of new items to include: HVAC, kitchen, appliances, paint, lights, and LVP flooring. Off of the back of the home there is a huge, vaulted, covered porch overlooking your private wooded lot.

480 Maverick Trl, Hedgesville

Listing courtesy of Butts Property Group LLC. Contact:

Lot 31 Trapper Ridge, Hedgesville
$55,000
Great laying lot almost 1.5 acres with some privacy! Class 1 perc approved, driveway access started, corners already marked. This lot is ready for plans and permits, get started building almost immediately! Not much clearing, good building site, good lot size and dimensions. This is a great lot in Sleepy Hollow with community amenities including the beach and lake access! The lot is immediately before 556 trapper ridge lane, hedgesville wv. Seller is Butts Properties LLC

Lot 31 Trapper Ridge, Hedgesville

Listing courtesy of Butts Property Group LLC. Contact:

28108 Cross Creek Dr, Salisbury
$419,990
3 Beds ⋅ 3 Baths
Why wait for new construction? Completed by a LOCAL builder in December 2022, this Like-New 3BR/2.5BA, 1872sf home in Salisbury's Sleepy Hollow neighborhood. Popular floorplan built by local, custom builder MH Builders / Malone Homes with many upgrades - gorgeous and durable LVP flooring throughout the living and dining areas, and baths; granite kitchen counters; upgraded cabinetry in the kitchen and bathrooms, ceiling fans in living room and all 3 bedrooms and sitting room. Welcoming front porch and foyer w/coat closet. Dreamy kitchen w/crisp white cabinetry, granite counters, breakfast bar, stainless steel appliances, pantry. Spacious living & dining areas. Laundry room and half bath complete the first floor. Upstairs, a true primary bedroom suite with a sitting room, and full, en-suite bath - step-in shower, double-width vanity, 2 walk-in closets, and an extra storage area. 2 generously-sized, additional bedrooms, a 2nd full bath with a double-sink vanity, tub/shower combo. Inside access to the 2-car attached garage and paved driveway. Sleepy Hollow is a sought-after, well-established neighborhood of gently winding streets, a handsome variety of home-styles, convenience of city services, sidewalks, and street lights in a great location! Minutes to Rt 50 and Downtown Salisbury - quick trip east to the Ocean or west to the Bay. Sizes, taxes approximate.Floorplan attached to the listing for reference only, and may show differences from the home as-built. Owner is a licensed realtor; agent has financial interest.

28108 Cross Creek Dr, Salisbury

Listing courtesy of EXP Realty, LLC. Contact:

3032 Crane Dr, Falls Church
$1,099,000
3 Beds ⋅ 3 Baths
Beautifully updated, meticulously maintained, and surprisingly spacious, this exceptional three-bedroom home offers an inviting combination of style, comfort, and flexibility in the highly sought-after Sleepy Hollow community—just minutes from Falls Church City and Washington, DC. From the moment you step inside, the home feels warm, open, and thoughtfully designed. Rich hardwood floors, abundant natural light, and beautifully selected finishes flow throughout the expansive main level, where oversized living and dining rooms provide wonderful space for entertaining or simply relaxing by the fireplace. The adjoining family room offers an equally inviting setting for everyday living or casual dining. At the heart of the home, the beautifully appointed kitchen features granite countertops, classic subway tile, a gas range, premium fixtures, and an easy connection to the surrounding living spaces. Just beyond, the screened porch creates a peaceful extension of the home—perfect for morning coffee, outdoor dining, or unwinding while overlooking the professionally landscaped, private backyard. Two generously sized bedrooms and a full bath with walk-in shower are conveniently located on the main level, offering tremendous versatility for family, guests, home offices, or multi-generational living. Upstairs, the private primary suite feels like a retreat of its own, with a vaulted ceiling, spa-inspired bath, and an impressive custom walk-in California Closet offering exceptional storage and organization. The separation between the primary suite and main-level bedrooms provides a level of privacy rarely found in a traditional floor plan. The spacious lower level adds even more flexibility with a large recreation room, third full bath, and versatile bonus room ideal for a home office, fitness space, guest area, or hobby room. A full-size two-car garage and convenient mudroom entry provide the storage and everyday functionality that make this home as practical as it is beautiful. Set against a serene, beautifully landscaped backdrop yet remarkably close to everything, this special Sleepy Hollow home offers the best of both worlds—space to spread out, flexible living options, and a peaceful neighborhood setting just moments from shopping, dining, commuter routes, walking and biking trails, Falls Church City, and all that the Washington metropolitan area has to offer.

3032 Crane Dr, Falls Church

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

409 E Marshall St E, Middleburg
$929,000
3 Beds ⋅ 3 Baths
Tucked at the end of a quiet side street in the historic town of Middleburg, this renovated ranch-style home offers comfortable, easy living just a short walk into town. The home was extensively renovated in 2020 and has recently been freshly painted on the exterior, making it truly move-in ready. The main level features an open floor plan with a well-appointed kitchen offering upgraded countertops, stainless steel appliances and a large island for casual dining or entertaining. The adjoining dining and living areas have recessed lighting and a large picture window overlooking the rear yard. There are three bedrooms, including an entry-level primary suite, and three full bathrooms, each with ceramic tile flooring and upgraded vanities, lighting and tub/showers. The fully finished lower level offers a spacious Recreation Room, bonus room, home office, full bath and separate laundry room. Other features include energy-efficient windows and ceiling fans throughout. Outside the 0.28-acre lot offers a large open rear deck for outdoor dining and entertaining, along with a covered front porch, an attached 1-car garage and paved driveway. An easy walk into Middleburg puts shops, restaurants and the town's many events right outside your door from the Christmas Parade and Oktoberfest to the Middleburg Film Festival. The Salamander Resort and National Sporting Library are also close by. Ideal commuter location only 35 minutes to Dulles International Airport and an hour to Washington DC. A nicely renovated home in a convenient in-town location that is turnkey and ready to enjoy.

409 E Marshall St E, Middleburg

Listing courtesy of Thomas and Talbot Estate Properties, Inc.. Contact:

67 Redbud Ln, Hedgesville
$245,000
2 Beds ⋅ 1 Baths
Great affordable small home in Sleepy Hollow, nice usable 1.53 acre lot, located near baseball field and picnic area, very close to the lake for swimming, fishing, kayaking, beach area. Situated in Morgan County but near the Berkeley County line. 2 BR 1 bath home, with propane FP, breakfast bar in kitchen. Great for 2nd home, investment, or residential.

67 Redbud Ln, Hedgesville

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Lot 34 Audubon Rd, Hedgesville
$48,990
Rare 2-acre opportunity in Sleepy Hollow! The property backs directly to Sleepy Creek Wildlife Management Area, giving you an incredible natural backdrop and access to thousands of acres of outdoor recreation. Unlike many mountain lots, this property offers usable, flatter ground and features a creek, adding even more character to an already special setting. Sleepy Hollow residents enjoy access to the community lake, and outdoor lovers will appreciate the nearby hiking, fishing, hunting, wildlife watching, and trail access, including the Tuscarora Trail and Devil’s Nose near the end of Maverick Trail. Peaceful, private, and packed with potential, this is the kind of land buyers hope to find in Sleepy Hollow but rarely do. Bring your plans, your boots, and your vision.

Lot 34 Audubon Rd, Hedgesville

Listing courtesy of Keller Williams Realty. Contact:

221 Dewdrop Ln, Hedgesville
$249,000
3 Beds ⋅ 1 Baths
Completely renovated, chalet-style loft cabin with a huge wraparound deck! Large windows with tall ceilings, all hardwood floors, and an updated kitchen featuring stainless steel appliances. Two bedrooms on the main floor, plus a loft area offering a flexible space for a home office or another bedroom. Outside you’ll find a large deck, spacious yard, and a brand new hot tub. The cabin is located in the Sleepy Hollow community, with access to a small private lake and beach – and only about 20 minutes from downtown Berkeley Springs. As a vacation rental, it generates about $28,000 in rental income each year (over $140k total since the seller bought it), and can come with an existing property manager and cleaner. Hot tub and furniture optional, available for purchase. See seller docs for a summary of rental history and financials. $1,000 buyer credit if you continue using the same property manager. Perfect vacation home!

221 Dewdrop Ln, Hedgesville

Listing courtesy of Blue Valley Real Estate. Contact:

6023 Tarry Town Rd, Salisbury
$439,900
4 Beds ⋅ 3 Baths
Nestled in the charming Sleepy Hollow community, this inviting Colonial home offers a perfect blend of comfort and style. With 4 spacious bedrooms and 2.5 bathrooms, this residence is designed for both relaxation and entertaining. The heart of the home features a well-appointed kitchen with upgraded countertops, a large island for casual dining, and essential appliances including a dishwasher, refrigerator, and Jenn air stove. The family room, conveniently located off the kitchen, is bathed in natural light and features a cozy double-sided wood fireplace, creating a warm ambiance for gatherings. Enjoy the luxury of a jetted tub and a walk-in shower in the master bathroom, providing a serene retreat after a long day. Thoughtful touches throughout the home include built-ins, recessed lighting, and window treatments that enhance the inviting atmosphere. The main floor laundry adds convenience to your daily routine, while the attached side-entry garage and ample driveway space ensure easy access and parking. Enjoy outdoor views from the rear screened porch off of the living area all set on a .34-acre lot. Experience the warmth and comfort of this delightful home looking for a new owner to restore it to its previous grander and to create lasting memories. Photos have been digitally enhanced and virtually staged.

6023 Tarry Town Rd, Salisbury

Listing courtesy of Sheppard Realty Inc. Contact:

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