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Browse All Rolling Woods Properties for Sale

$349,000
3 Beds 2 Baths VASP2043448 MLS
Opportunity knocks at Lake Anna! Located in the desirable Rolling Woods subdivision on the public side of Lake Anna, this custom-built ranch-style home offers one-level living, an assigned boat slip (#61) in the community common area, and endless potential for the right buyer. Situated on a spacious .92 acre corner lot, this 3 bedroom, 2 bath home features approximately 1,800 square feet of living space, a 2 car attached garage, and access to high-speed FiberLync internet. Inside, you'll find great bones and architectural features that are hard to replicate, including vaulted ceilings, skylights, beautiful wood flooring, and a cozy gas fireplace with a brick surround. The functional kitchen offers vaulted ceilings and a breakfast bar with seating, while the primary suite features a walk-in closet and private bath. Outdoor living spaces include a screened porch and rear deck, providing the perfect setting to enjoy the Lake Anna lifestyle. This home does need TLC and updating and is being offered as an opportunity for buyers with vision. With some love, attention, and renovations, this property has the potential to become a truly stunning lake retreat, full-time residence, or investment property. Whether you're looking to create your dream lake home or capitalize on a value-add opportunity, properties with this combination of location, boat slip access, and potential are hard to find. Bring your ideas and unlock the possibilities at Lake Anna! Rolling Woods offers fantastic lake amenities including two boat ramps, a waterfront common area with picnic space, and boat slips. Spend your days boating, fishing, and enjoying everything Lake Anna has to offer. Conveniently located less than two hours from Washington, D.C., and just minutes from local favorites including waterfront dining, mini golf, marinas, and the beloved Moo Thru ice cream shop. Property is being sold strictly as is.

7213 Deerhill Rd, Orange

$429,999
3 Beds 2 Baths VASP2043178 MLS
48 inch zero turn lawn mower conveys! Lake Anna living starts here! Built in 2022 by Bethel Homes and nestled on a .98-acre lot in Rolling Woods subdivision on the public side of Lake Anna, this beautiful Craftsman-style ranch offers quality construction, and a fun lake lifestyle. Offering 1,248 square feet of easy one-level living, the home features 3 bedrooms, 2 full baths, and an inviting open floor plan. Inside, you'll find 9-foot ceilings, luxury vinyl plank flooring throughout, and a cozy wood-burning stove that creates a warm and welcoming atmosphere. The kitchen is both stylish and functional with granite countertops, stainless steel appliances, a farmhouse sink, and a center island with seating that opens seamlessly to the living and dining areas. The primary suite offers a spacious walk-in closet, double vanity, and a walk-in shower. Two additional bedrooms, a full bath and laundry complete the interior. Washer and dryer convey! Outside, enjoy the covered front porch, rear deck, fenced backyard perfect for pets or children, beautiful landscaping, and a fire pit area ideal for relaxing after a day on the lake. Additional features include attractive board and batten siding, stainless steel gutter guards, an encapsulated crawl space, and an attached front-loading two-car garage. High-speed FiberLync internet is available! Rolling Woods offers fantastic lake amenities including two boat ramps, a waterfront common area with picnic space, and several boat slips available for lease through the HOA. Spend your days boating, fishing, and enjoying everything Lake Anna has to offer. Conveniently located less than two hours from Washington, D.C., and just minutes from local favorites including waterfront dining, mini golf, marinas, and the beloved Moo Thru ice cream shop. This is an excellent opportunity to enjoy the Lake Anna lifestyle in a newer home with beautiful finishes, privacy, and convenience. Don't miss it!

7314 Sugar Hollow Rd, Orange

$609,000
5 Beds 3 Baths VASP2038438 MLS
NEW CONSTRUCTION - The Dream Model by Fantasy Homes! 4 pictures virtually staged. Low price and lower interest rates on a quality built custom home. It’s a perfect time to purchase now and be ready for warmer weather. You won’t find a home with so many amenities for less! Located on a quiet cul-de-sac and set on nearly 1 acre, this beautiful new home offers privacy, surrounded by mature trees, and includes a deeded boat slip just a short distance away on Lake Anna with good water depth. Fiber Optic Gigabit internet available. The home features five bedrooms (possibly six), three full bathrooms (3-bedroom septic), 3,718 sq ft., and main-level living. It also includes a kitchen with upgraded counters and a pantry. This home combines quality construction with thoughtful design. The main level features a separate mudroom with custom benches, a large laundry room, and a dedicated multipurpose room, perfect for a small home office or any other use you can imagine. The primary suite features a standalone tub, a separate shower, a dual-sink vanity, and a MASSIVE custom walk-in closet with a large window. Enjoy scenic views from the expansive, partially covered rear deck and the covered front porch. The finished basement features several large rooms, as well as a large unfinished area for storage and utilities. Additional features include a dual-stage water filtration system and an energy-efficient design, ensuring you can enjoy your home while being environmentally responsible. Don't miss this opportunity to own a brand-new home with lake access and modern amenities! Contact me today to learn more or schedule a visit and make your Fantasy Home a reality!

15409 Drummers Lane, Orange

$499,900
4 Beds 3 Baths VASP2037792 MLS
Priced below the most recent appraisal, offering buyers a rare opportunity for immediate equity!!! Lake life is calling—now is your opportunity to answer at an exceptional new price point. Welcome to 7312 Sugar Hollow Road, a beautifully positioned retreat offering privacy, amenities, and effortless access to everything Lake Anna has to offer. Set on a private 1-acre lot, this home delivers peaceful surroundings just minutes from local dining, local breweries, and Lake Anna State Park. An assigned boat slip (#43) just down the street makes spontaneous lake days and sunset cruises a breeze. The backyard is built for relaxing and entertaining with a resurfaced in-ground pool, fresh decking, and multiple outdoor living spaces. Inside, you’ll find light-filled living areas, a cozy fireplace, rich finishes, and a well-appointed kitchen with stainless appliances and generous counter space—ideal for gathering. With four bedrooms and three full baths, there’s plenty of space for guests or extended stays. The primary suite offers a spa-like retreat with soaking tub, while the finished walk-out basement provides flexible space for guests, recreation, or a home office. Two balconies and a large rear deck extend the living space outdoors. Recent updates include newer HVAC, resurfaced pool, pool pump replacement in 2024, and fresh decking, allowing you to focus on enjoyment rather than projects. Whether you’re seeking a full-time residence, weekend escape, second home, or short-term rental opportunity, this property offers the location, flexibility, and lifestyle that make Lake Anna so desirable. Offered at $499,900—ready for immediate enjoyment and your next chapter at the lake.

7312 Sugar Hollow Rd, Orange

$1,200,000
4 Beds 4 Baths VASP2036748 MLS
Welcome to this one-of-a-kind waterfront property located on the public side of Lake Anna, Virginia. This beautiful home offers 4 bedrooms, 4 bathrooms, and over 4,500 square feet of living space. As you arrive, a private, tree-lined driveway leads to the front of the home, offering both seclusion and a peaceful setting surrounded by nature. Upon entering, you are greeted by a spacious foyer with ample storage and an inviting den area featuring a custom rock wet bar that is perfect for entertaining. Off the hallway are two full bathrooms and three spacious bedrooms, providing plenty of room. The large kitchen features extensive cabinetry, plenty of counter space, a generous pantry, and a bar-height seating area. From the kitchen, you can walk out to a large wraparound deck that is ideal for outdoor dining and relaxing while taking in beautiful views of the lake. The main living room offers a stunning rock fireplace and large windows that fill the space with natural light and capture views of the water. From this area, you can also access the deck and the primary bedroom. The primary suite includes large windows overlooking the lake, two closets, and a grand bathroom. Upstairs, you will find a large bonus room that offers endless possibilities for a recreation area, home theater, or additional living space. The basement level is finished and includes a family room, office area, game room, full bathroom, laundry room, and a spacious utility room with additional unfinished areas ready for your vision. Outside, two levels of wraparound decks provide plenty of outdoor living space and are in excellent condition. A set of stairs leads to the backyard, where you will find a beautifully designed hardscaped area with flat land, a fire pit, and plenty of room to enjoy the outdoors. Your private dock is just steps away and includes two boat slips and an upper-level deck with covered seating and wide, unobstructed views of the lake. This home is conveniently located close to local amenities, grocery stores, and restaurants. Short-term rentals are allowed, and high-speed internet is available. Most furniture can convey. This home features an upgraded water softener system. This home is truly a must-see to appreciate all that it offers. Come tour this remarkable property and experience lakefront living at its best.

7320 Old Dickersons Road, Orange

$650,000
7 Beds 4 Baths CVR-2516623 MLS
Welcome to a home redefining flexibility, comfort, and connection—perfectly tailored for today’s multigenerational lifestyles. Cradled in the center of a peaceful wooded cul-de-sac in one of Williamsburg’s most desirable neighborhoods, this expansive 7-bedroom 4.5 Bath residence offers not just space, but possibility. Whether you're blending households or love hosting long-term guests, this home delivers. At the heart of this gem is its rare and thoughtful layout—two spacious primary bedroom suites, one on each level, offering privacy and convenience. Each with Walk-In Closets. But what truly sets 2712 Linden Lane apart is the attached 2-bedroom, 1-bath private suite with its own entrance and ramp. It’s not just an in-law suite—it’s a fully integrated living space to keep loved ones close. Ideal for aging parents, adult children, or a live-in caregiver, this suite will transform the way your family lives together by offering unparalleled comfort and convenience for multigenerational living. Inside discover all formal living areas, a family room with beamed ceiling, large kitchen with island Walk-In Pantry and island, and generously sized secondary bedrooms. The large Breakfast Nook with bay windows overlooks the wooded views. Natural light pours in through skylights, creating a warm, uplifting atmosphere throughout. Step outside to enjoy tranquil lush views of the wooded backyard and a serene community pond—your own private escape. Minutes from the shops and restaurants of the lively New Town center, the College of William & Mary, Colonial Williamsburg, and military bases. This is more than a home, it’s a lifestyle solution!

2721 Linden Lane, Williamsburg

$524,900
4 Beds 2 Baths VASP2031754 MLS
Welcome to your perfect lakefront escape on the public side of Lake Anna, VA. This charming A-frame cottage offers the ideal setting for relaxing getaways or full-time lake living. Featuring 1,715 finished square feet, the home includes 3 bedrooms, 2 full baths, plus a versatile bunk room in the finished basement. The main level showcases an open floor plan with hardwood flooring, an eat-in kitchen, and a vaulted family room filled with natural light. A bedroom, full bath, and mudroom complete the main level. Upstairs, you'll find two additional bedrooms and a full bath. Downstairs, the finished basement offers extra space to spread out, with a rec/family room, bunk room, and laundry area. Step outside to a covered wrap-around porch and spacious rear deck—ideal for BBQs and outdoor entertaining. Gather around the fire pit on cool evenings or head down the wooded path by foot or ATV to your private waterfront oasis. Enjoy 30 feet of bulkheaded shoreline and your own covered boat dock equipped with a generator-powered lift. Whether you're watching sunsets with a cocktail in hand, taking a boat ride or a peaceful paddle, this is lake life at its best. Additional features include a paved driveway, an 8x10 storage shed, and a 24x30 detached garage with high bay doors—perfect for storing your boat, lake toys, or vehicles. Recent upgrades include a new water heater (2022) and a new Trane HVAC system for the upper level (August 2024).

7314 Hidden Brook Road, Orange

$430,000
3 Beds 2 Baths VASP2029384 MLS
Discover the perfect blend of comfort, privacy, and lake life at this beautiful 3-bedroom, 2-bathroom home. Nestled on a private, tree lined lot, this property offers the peaceful feel of a Lake Anna retreat while maintaining convenient access to amenities. SLIP INCLUDED! Step inside to an open concept living space where the living room seamlessly connects to the kitchen, featuring expansive countertops and plenty of space for cooking and entertaining. Just off the main living area, enjoy easy access to the screened-in back porch, perfect for relaxing and taking in the serene surroundings. The primary bedroom is a true retreat, complete with an attached ensuite bathroom featuring a gorgeous walk in shower and soaking tub. Designed for main floor living, this home offers a well thought out split bedroom floor plan, with two additional bedrooms and a full bathroom on the opposite side for added privacy. Additional highlights include an attached two car garage and a detached carport, offering plenty of parking and storage space. As a bonus, this property comes with boat slip #79 in the community’s common area, providing convenient lake access. The community amenities include boat ramps, picnic tables, seating areas, and more, making it easy to enjoy life on the water. High speed internet is available. Plus, this home is located on the public side of Lake Anna and in one of the top rated short term rental markets, presenting a fantastic investment opportunity. Ideally positioned just a short drive from the local grocery store, restaurants, and shopping, this home is also within about an hour of Richmond, Culpeper, Charlottesville, and Fredericksburg—and about 90 minutes from Northern Virginia and Washington, D.C. This is more than just a home, it’s a lake access retreat designed for relaxation, recreation, and making unforgettable memories. Don’t miss your chance to own a slice of Lake Anna paradise! Schedule your showing today.

7204 Old Dickersons Road, Orange

$765,000
4 Beds 4 Baths VALO2082534 MLS
Welcome Home to 21757 Rolling Woods Place! Nestled at the end of a cul-de-sac, this charming Colonial features 4 bedrooms, 2.5 baths, 3 finished levels, a spacious backyard, and many updates. With All New Windows conveying a lifetime warranty, Fresh Paint through much of the home, New front door, beautiful New wide-plank natural Hardwood Flooring, New basement carpet, freshly resurfaced extra-wide driveway, this home has been lovingly maintained by the original owner. On the main level you will be welcomed with gleaming new hardwood floors leading to the family room with soaring ceiling boasting a two-story wood burning fireplace, this room opens to the kitchen with a sliding door leading to a deck and spacious back-yard. Also off the kitchen is a large sunroom that’s perfect for additional entertaining, home office, or you name it! A half-bath, spacious formal living room, and dining room complete the main level. Upstairs you will find 4 nicely sized bedrooms and a large primary ensuite bathroom with walk-in closet and a full hall bathroom. The lower level has the laundry room with TONS of storage, a rec room, a separate space for creating a bar or exercise room, PLUS a 3rd full bathroom and bonus room that can be used for guests or home office. Located in the heart of Sterling, this home offers easy access to a variety of shopping, dining, and entertainment options, as well as major commuter routes for convenient travel throughout the region. Additionally, residents of Rolling Woods Place enjoy access to parks, walking trails, and more. Don't miss this gem!

21757 Rolling Woods Place, Sterling

$823,000
3 Beds 4 Baths VASP2026706 MLS
Discover the charm at this breathtaking custom-built Northern White Cedar log home situated on the public side of Lake Anna, Virginia. This exceptional waterfront retreat features 3 bedrooms, 3.5 baths, 2,476 square feet and a spacious loft that offers versatile living space. The inviting family room showcases vaulted wood and beam ceilings, a stunning stone wood-burning fireplace, and rich hardwood flooring, creating a warm and cozy ambiance. The family room flows seamlessly to the dining area and the kitchen that features sleek granite countertops and stainless steel appliances. The main level lakeside primary ensuite has direct access to the spacious back deck. A half bath and laundry room complete the main level. Upstairs your guests will enjoy their own space with a bedroom, full bath and a loft area perfect for additional sleeping or the perfect lounging area. The finished walkout basement is perfect for entertaining, complete with a wet bar and ample space for relaxation with a living room, rec area, bedroom, full bath and storage room. Multi-level decking extends your living area outdoors, providing the perfect space for cookouts and family gatherings. The lower level deck is re-enforced for a hot tub and there is already a separate power box installed. Attached one car oversized garage and 12x20 shed on the property. Take a stroll down to the water's edge where you'll enjoy your private boat dock equipped with a manual boat lift and canopy cover, plus an additional area that would be perfect for docking jet skis. The sun deck offers the perfect spot for soaking up the sun or simply enjoying the tranquil surroundings. Great location; less than 2 hours from D.C. and just minutes by boat or car to local dining, MooThru ice-cream, Below Deck LKA deli sandwiches and pizza, arcade and mini golf. The lake life you've always dreamed of is within arms reach and at an affordable price! The 2005 Searay 18' sport boat, golf cart and riding lawn mower can convey with an acceptable offer. Furniture is negotiable! Brand new septic installed May 2023. See MLS documents section for list of improvements. Short Term Rentals are permitted!

7319 Sugar Hollow Road, Orange

$435,000
3 Beds 3 Baths VASP2024844 MLS
Stunning Lake Anna Access Retreat Welcome to this exquisite Lake Anna water access home nestled in the Rolling Woods subdivision at 7207 Old Dickerson Rd, Orange, VA. This charming abode offers a serene retreat on a generous 0.92-acre corner lot adorned with mature trees. The home boasts 3 bedrooms, 3 full baths, a versatile game room or office, and a bonus room. The property includes a deeded boat slip, perfect for lake enthusiasts. The spacious family room, kitchen with a central island, stainless steel appliances, and cozy breakfast nook create an inviting atmosphere. A separate formal dining room adds elegance to gatherings. The main level master suite features a walk-in closet, double vanity, corner tub, and separate shower. Another main-level bedroom, full bath, and game room with a wet bar enhance convenience and entertainment. Upstairs, find a third bedroom, full bath, and bonus room. The property was previously a short-term rental on Airbnb and VRBO until the owner moved in May 2023. The owner was making $30-35K annually from these rentals. Further details can be provided if you want to buy it as an investment property. There is also an option to purchase it fully furnished. Please ask for more information if needed. Recent updates include new carpeting, granite countertops, skylights, updated bathrooms, new appliances, and a new HVAC system. Community amenities include boat slips, two boat ramps, and picnic tables. Proximity to local attractions ensures endless leisure opportunities. Schedule a private tour today.

7207 Old Dickersons Road, Orange

$712,700
4 Beds 4 Baths VALO2069382 MLS
Welcome to this lovely colonial-style home in Sterling, Virginia's sought-after Rolling Woods neighborhood. Offering a seamless combination of luxury, comfort, and contemporary convenience, this house is an excellent retreat for modern living, complete with a plethora of community facilities such as parks, walking paths, and more, promoting a dynamic and active lifestyle for all. This property has 3 levels, 4 bedrooms, and 3.5 full baths, offering plenty of area for comfortable family living and entertaining visitors. The pleasant interior is bathed with natural light, emphasizing the soaring ceilings and the attractive wood-burning fireplace, which is ideal for peaceful nights with loved ones. Prepare culinary delights in the well-appointed kitchen, which has stainless steel equipment and gorgeous granite counters and is suitable for both everyday and special occasions. Enjoy the warmth and durability of hardwood flooring on the main level, which flows gently up the staircase and into the upper hallway, leading to spacious bedrooms with new carpet. The lower level provides even more multipurpose space, also with new carpet, featuring a den and gym room, as well as a complete bath and convenient kitchenette area, allowing for infinite leisure and recreation opportunities. Outside, you'll love the large deck and level backyard, which are ideal for hosting and gatherings. Rolling Wood residents benefit from convenient access to a wealth of shopping, dining, and entertainment opportunities, as well as major commuter roads and Dulles Airport nearby. Don't miss the opportunity to make this exceptional property your new home. Schedule your showing today and discover the epitome of luxurious living in Rolling Woods, Sterling!

21748 Pinewood Court, Sterling

$350,000
3 Beds 2 Baths VASP2024740 MLS
Step into serenity with this charming three-bedroom, two-bathroom home with HIGH SPEED INTERNET nestled near the tranquil shores of Lake Anna. Perfectly situated amidst a canopy of trees, this picturesque retreat offers both privacy and access to the great outdoors. As you step through the front door, you'll be welcomed into a warm and inviting living space bathed in natural light. The open-concept layout seamlessly connects the living room, dining area, and kitchen, creating an ideal setting for both relaxation and entertainment. From the dining area you'll discover the screened-in back porch, where you can savor your morning coffee amidst the sounds of nature or host alfresco gatherings with family and friends. There is also a front covered front porch that can be enjoyed. Outside, the "Rolling Woods" neighborhood offers even more to explore. A private BOAT SLIP provides easy access to the public side of Lake Anna, where you can spend your days boating, fishing, or simply soaking up the sun on the water. Back on land, the expansive backyard offers plenty of room for outdoor activities, from picnics and barbecues to games and gardening. You'll also appreciate the one car garage and the additional covered parking and work shed. Located a short drive from Lake Anna State Park, this home offers endless opportunities for outdoor recreation, including hiking, biking, and wildlife viewing. Meanwhile, nearby amenities such as shopping, dining, and entertainment ensure that you're never far from the comforts of modern living.

15403 Drummers Lane, Orange

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