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

$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:

$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: 5406876500
$260,000
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: (304) 263-7800
$550,000
4 Beds ⋅ 3 Baths
Meticulously maintained and set on 1.03 acres in Huntingtown, this home offers four bedrooms, three full bathrooms, and approximately 1,954 square feet of finished living space across two levels. The updated kitchen features granite countertops and a backsplash, while wood flooring and a dedicated dining area complement the inviting main level. Three bedrooms and two full bathrooms are located on this level, including a primary bedroom with an attached bath. The finished walkout lower level provides a fourth bedroom, a third full bathroom, and flexible space for recreation, a home office, or hobbies. Outside, an elevated deck overlooks an expansive backyard with mature trees, offering a welcoming setting for outdoor dining, entertaining, and relaxation. A fireplace, generous driveway parking, and NO HOA add to the property’s appeal. Notable improvements include window and water heater replacements in 2020, septic replacement work in 2021, and HVAC replacement in 2023. These updates, combined with the home’s meticulous upkeep, versatile layout, and spacious outdoor setting, make this Huntingtown property a standout ready for it's new owner.

5850 Stephen Reid Rd, Huntingtown

Listing courtesy of Pearson Smith Realty, LLC. Contact: listinginquires@pearsonsmithrealty.com
$389,900
3 Beds ⋅ 2 Baths
Welcome home to this brand-new 3-bedroom, 2-bath rancher situated on a 1.53-acre lot in one of the area’s most desirable subdivisions! Thoughtfully designed with comfort and functionality in mind, this home offers spacious one-level living along with a full unfinished walkout basement featuring 9-foot ceilings, providing endless possibilities for future expansion, a recreation room, home gym, or additional living space. The inviting primary suite serves as a private retreat, complete with a luxurious en-suite bath featuring a relaxing soaking tub, separate shower, and double vanities. The open floor plan is ideal for both everyday living and entertaining while large windows fill the home with natural light. Step outside and enjoy the peaceful backyard or take advantage of the exceptional community amenities, including park and picnic areas, a scenic pond perfect for fishing or launching a canoe, kayak, or other non-motorized boats, and plenty of green space to enjoy the outdoors. If you’re looking for the perfect combination of new construction, acreage, and an outstanding community, this home checks all the boxes. Don’t miss your opportunity to own this incredible gem—schedule your private showing today!

2499 Audubon Rd, Hedgesville

Listing courtesy of Burch Real Estate Group, LLC. Contact: (681) 252-3002
$1,385,000
5 Beds ⋅ 3 Baths
Unique Opportunity: Over an Acre in a Private Luxury Enclave – Just 15-20 Minutes from Downtown DC in desirable Sleepy Hollow Spacious mid-century rambler with a private pool and beautiful gardens on over an acre of land. Almost 4,000 finished square feet on two levels, plus an oversized 2-car garage and workshop. Main Level features a dramatic living room with a marble fireplace, formal dining room, bright 31’ x 11’ sunroom with a second fireplace, 4 bedrooms, 2 full bathrooms, and an updated kitchen. Lower Level includes a cozy family room with a wood-burning fireplace, separate workout/play room, guest bedroom (5th BR), third full bathroom, and a large cedar shoe/coat closet. Finished in 2019 with a room addition. Recent Updates (since 2018): New roof, skylights, AC/furnace, second-zone heating/cooling, water heater, whole-house Wi-Fi generator, top-of-the-line washer/dryer, recessed lighting, and a 31’x16’ screened room. Outdoor Living: Private fenced yard with mature landscaping, a serene Zen garden, and a beautiful azalea garden. Stunning views from every room.

3152 Holmes Run Rd, Falls Church

Listing courtesy of Hawkins Real Estate Company. Contact: 2407932485
$49,500
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: 7036690099
$1,690,000
6 Beds ⋅ 6 Baths
One of Northern Virginia's rare luxury residences designed for effortless living at every stage of life. Thoughtfully crafted with universal design principles, this custom home blends architectural elegance with exceptional comfort, creating a future-ready residence where sophisticated design and everyday convenience exist in perfect harmony. A private elevator serves every level, while zero-threshold entryways, graciously proportioned hallways, and a beautifully appointed primary suite with a spa-inspired en-suite bath as well as a main level bedroom with ensuite bath. All of the amenities provide seamless convenience for everyday living, welcoming overnight guests or multigenerational living—all without compromising refined style. Welcome to 2998 Beechwood Lane, a custom-built six-bedroom, five-and-a-half-bath residence offering nearly 6,000 square feet of refined living space in an exclusive enclave within the coveted Sleepy Hollow area of Falls Church. As an added distinction, a coveted membership to the Sleepy Hollow Bath & Racquet Club conveys with the property. Designed for both elegant entertaining and comfortable daily living, the heart of the home is an exceptional chef's kitchen featuring custom maple cabinetry, quartz countertops, premium Thermador appliances, an oversized center island, built-in wine cooler, and a stylish dry bar. The open-concept design flows effortlessly into the sun-filled breakfast area and expansive family room, anchored by a dramatic floor-to-ceiling stone gas fireplace, before extending outdoors to a spacious TREX deck overlooking beautifully landscaped grounds. The upper level is anchored by an expansive primary retreat featuring dual custom walk-in closets and a luxurious spa-inspired bath. Additional bedrooms offer a thoughtful blend of private en-suite and shared bath layouts, providing exceptional flexibility for family and guests alike. Elevator access to every floor, abundant storage, and a dedicated laundry room further enhance the home's seamless functionality. The fully finished lower level offers exceptional versatility with a spacious recreation room, dedicated fitness studio, an additional bedroom with a private en-suite bath, generous storage, and plumbing already in place for a future wet bar—creating the ideal setting for entertaining, extended stays, an au pair suite, or private guest accommodations. Outside, professionally designed landscaping creates a private retreat complete with inviting gathering spaces, a welcoming front porch, accessible walkways, pathway lighting, a cedar privacy fence, an irrigation system, and beautifully integrated outdoor living areas equally suited for quiet mornings or memorable evenings with family and friends. Exceptional craftsmanship is complemented by premium infrastructure, including a partial-home Generac generator, dual-zone HVAC, an integrated security system, and upgraded electrical and low-voltage systems designed for today's connected lifestyle. Perfectly positioned inside the Capital Beltway and less than 10 miles from Washington, D.C., this exceptional residence offers effortless access to Metro, major commuter routes, premier shopping, acclaimed dining, and the very best of Northern Virginia. Combining enduring architecture, sophisticated finishes, and thoughtfully integrated universal design, 2998 Beechwood Lane is a rare offering that delivers luxury, flexibility, and lasting value for generations to come.

2998 Beechwood Ln, Falls Church

Listing courtesy of Serhant. Contact: 8777374268
$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 $24,000 in rental income each year (over $100k 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: (540) 303-3616
$445,000
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: 4437830299
$179,900
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 Burch Real Estate Group, LLC. Contact: (681) 252-3002
$40,000
Are you looking for a little slice of land to build your part-time retreat or full-time residence? You may wish to consider this wooded lot in Sleepy Hollow Subdivision. This lot is heavily wooded, so it would need to be cleared. Sloped, but the view from the lot is awesome. This lot is located on dead end road too, so there is very little traffic. Mature trees, both standing and fallen -- make the most of it and use the fallen timber for firewood. Buyer to perform their own due diligence. Sleepy Hollow is located just minutes from Route 9 and about 15 minutes from I-81. This lot backs up to Sleepy Creek Wildlife Management area which offers hunting, fishing, nature trails and so much more. Additionally, this lot is just below the Tuscarora Trail. A straight walk "up the mountain" will take you to an amazing, pristine overlook with a path that leads to that Tuscarora Trail. There's so much more to discover with them gem of a lot - it's literally a hikers paradise! Drive by and take a look. You might like what you see!

Lot 16 Dewdrop Lane, Hedgesville

Listing courtesy of Burch Real Estate Group, LLC. Contact: (681) 252-3002
Start Your Search