Rolling Hills Estates Real Estate, Homes, Condos for Sale in Lancaster, VA

5 Beds ⋅ 3 Baths ⋅ VAFV2034472 MLS

Contract fell through! Interest rates have gone down! Extensive Renovations: The home has been fully renovated in 2025, including updates to kitchen, bathrooms, flooring, and fresh paint throughout. Designed to accommodate two families comfortably, featuring large rooms that are flooded with natural light like the entire house. The lower level is equipped with wheelchair-accessible features, enhancing mobility and convenience. Ideal for Home-Based Businesses: The layout and zoning may support various home-based businesses, including daycare or childcare services. New appliances installed 2025. Roof gutters, A/C & water heater have been replaced in last 3 years and $70,000+ in recent renovations. The big house sits on a large 0.4 Acre lot with room for expansions and it's just min to the heat of Winchester, 30 min from Leesburg or 60 min from Tysons Corner. Some Purchasers qualify for Down Payment assistance, check with your preferred Real Estate Agent. Your cost of living could be under $2,900/M after Tax Deductions and some money Down, even much lower if you rent out the BSMT.

110 Carter Place, Winchester

$675,000

5 Beds ⋅ 4 Baths ⋅ VAWI2009168 MLS

Location Location Location! Welcome to 800 Lake Dr. Winchester VA 22601, Located in the highly sought-after Rolling Hills community and situated on a 0.37 acre lot, This expansive home offers 4,500+ sqft. of living space, featuring 5 bedrooms, 4 Full baths, finished basement, and 2 car garage! Step inside to find gleaming hardwood floors in the formal living and dining rooms. The unique open-concept layout showcases a bright kitchen with granite countertops, a large center island, and a breakfast area that opens to the spacious family room with a cozy gas fireplace. The main level also includes a generously sized guest room and full bath—ideal for a home office or guest suite. + Laundry, with access to garage. Upstairs, the luxurious primary suite impresses with a large open layout, featuring tray ceilings, walk-in closet & additional lounge room perfect for a private gym or seating area. Three additional nicely sized bedrooms and a full bath complete the upper level! The finished basement is built for entertaining, featuring a large rec room, full kitchen, full bath and an additional den. There's also a sizable unfinished area for storage, plus walk-out access to the fully fenced backyard. Enjoy outdoor living with access from both the kitchen and basement to a beautifully landscaped backyard—perfect for relaxing or hosting. This home is located just minutes from major shopping, dining, schools & more! Don’t miss the opportunity to call this stunning property home!

800 Lake Drive, Winchester

$175,000

VAWI2009810 MLS

Vacant Lot in Rolling Hills One of the last opportunities to own a vacant lot in the desirable Rolling Hills community. This property offers the perfect setting to build your new home or presents an excellent opportunity for a long-term investment. Enjoy a well-established neighborhood with limited remaining buildable lots. Buyer to verify zoning, utilities, and intended use. Water and Sewer tap Fees have NOT been paid.

719 Kennedy Dr, Winchester

$650,000

5 Beds ⋅ 4 Baths ⋅ VAWI2009484 MLS

Rolling Hills Estates located in the Winchester City area, this beautifully maintained 5-bedroom, 3.5-bath home offers 3,552 sq ft of finished living space on a .35-acre cul-de-sac lot. Featuring a 3-car garage w/220 Car Charger, fully fenced backyard, covered front porch, and a rear Trex deck with lighting and stairs to the yard, this home is built for comfortable living and entertaining. Inside, the main level boasts hardwood flooring, an open floorplan, a gourmet kitchen with granite countertops, stainless steel appliances, island, under counter lighting, tile backsplash, butler’s pantry, wine/beverage fridge, separate dining room, and a cozy family room with fireplace. The play area can be used as an office or library. Upstairs, the spacious primary suite includes an ensuite bath and walk-in closet, along with three additional bedrooms, a full bath, and convenient upper-level laundry. The finished walk-out basement adds a private bedroom and full bath, recreation room, office/flex room, and storage. Minutes from Historic Winchester, Shenandoah University, I-81, Route 7, shopping, restaurants, the exciting Cedar Valley project that is underway includes a 50,325-square-foot Publix Super Market, set to open by March 2027, alongside 327 residential units—comprising townhomes, condominiums, and apartments—and 22,600 square feet of commercial and retail space. A four-level, 376-space parking garage with rooftop recreational facilities, such as pickleball courts, will further enhance the area’s appeal & MORE. Just in time to celebrate the holidays in your next home!

2708 Cassidy Court, Winchester

$395,000

4 Beds ⋅ 2 Baths ⋅ VAOR2010138 MLS

Welcome to your own private retreat! This 4 bedroom, 2 full bath rambler sits on a serene 2 acre lot, offering the perfect blend of comfort, space, and functionality. Step inside this spacious single-level layout featuring an open concept living, dining and kitchen area, with stone fireplace and access to the back deck. Down the hall you will find an office nook, and the primary bedroom with its private en-suite bath. In addition, there are 3 additional bedrooms and a hall bath. Outside, the property truly shines! Relax on the deck overlooking the expansive back yard. There are two 2 car garages providing room for cars, storage, or hobbies. There are even 2 driveways to the property! Don't miss your opportunity for your oasis in Orange County!

4253 Rolling Hills Drive, Culpeper

$739,000

5 Beds ⋅ 5 Baths ⋅ VAWI2008744 MLS

Nestled on a quiet cul-de-sac within city limits, this exquisite 5-bedroom, 4.5-bath colonial offers over 4,625 square feet of finished living space and a rare backdrop of preserved battlefield views. Step into the grand two-story foyer flanked by formal living and dining rooms, then flow into the expansive family room featuring coffered ceilings and a dramatic floor-to-ceiling stone fireplace. The gourmet island kitchen is a chef’s dream, boasting stainless steel appliances, double wall ovens, a walk-in pantry, and abundant counter space. It opens to a sun-drenched morning room — the perfect spot for your first cup of coffee. Distressed hardwood floors add warmth and character throughout the main level, which also includes a private office with French doors. Upstairs, the luxurious primary suite is a true sanctuary, complete with a double-sided fireplace and spa-inspired ensuite featuring a dual-head shower, separate jetted tub and dual walk-in closets. Four spacious secondary bedrooms and a custom upper-level laundry room provide comfort and convenience for the whole household — complemented by a second laundry on the main level. The finished basement expands the home’s versatility with a dedicated fitness room featuring rolled rubber flooring and commercial-grade electrical setup to support cardio equipment. Outdoors, the freshly refinished deck overlooks a large, fenced backyard — ideal for entertaining — and includes electrical access for a future pool and hot tub installation. Garage also climate controlled with heat and a/c. With its prime cul-de-sac location, timeless craftsmanship, and thoughtful upgrades, this home offers the perfect blend of elegance, privacy, and everyday ease. HVAC recently replaced.

921 Kennedy Drive, Winchester

$775,000

5 Beds ⋅ 4 Baths ⋅ MDPG2148288 MLS

Stunning 5 bedroom brick home in Rolling Hills Estates! This beautiful home offers a two story Foyer that opens to the welcoming Living Room. Enjoy a huge Dining Room, perfect for hosting. Bright Office with plenty of space to work from home. Everyone will love spending time together in the Family Room with the 10 foot ceiling and stone wall fireplace equipped with a wood stove insert. The well equipped Kitchen offers light toned cabinets and counters, gas cooktop, wall oven with microwave, pantry, backsplash, and island. The expansive vaulted Sun Room is bright with all the extra windows and skylights. The Primary Suite is massive and offers a Sitting Room with a gas fireplace, 2 walk-in closets, and an en suite Bathroom featuring double sinks, shower, and soaking tub. 2 of the 3 generous Bedrooms upstairs have connecting Bathroom access. Finished basement with enormous Great Room features a wood burning fireplace, additional Office, 5th Bedroom, and a Storage Room that complete this home THE gorgeous HARDWOOD FLOORS are have been refinished and look brand new ..... Hardwood flooring includes the Foyer, Family Room, Dining Room and Stairs. The carpet has all been replaced too! The entire home has been repainted and the entire basement has new flooring as well. The yard backs to woods for added privacy. Close to shopping, restaurants, parks, casinos and more. Excellent commuter location - 15 miles to Alexandria. 13 miles to Joint Andrews Air Force Base. 18 miles to Capital Hill. 12 miles to the National Harbor Interesting fact about this neighborhood..... the last time a home sold in this neighborhood was 2018 and prior to that was 2016 and prior to that was 2006. This neighborhood is truly a sought after neighborhood and homes are rarely for sale.

15511 Helen Drive, Accokeek

$507,000

3 Beds ⋅ 3 Baths ⋅ VAWI2007130 MLS

Need more space but don’t want the hassle of a massive house? This 3-bedroom, 2.5-bath home gives you exactly what you need—smart space, modern updates, and a location that makes life easy.<br? The updated kitchen (2022) is ready for everything from quick breakfasts before school to weekend dinners with friends. When the weather’s nice, just slide open the kitchen door to your private backyard and patio—perfect for grilling, relaxing, or after-school playtime.<nbr> Inside, the family room with a gas fireplace is your go-to spot to kick back and unwind. That front room with a bay window? Use it as a dining room, home office, or playroom—whatever works for your life. Upstairs, the primary suite is your retreat, with a walk-in closet and private bath—finally, a space that’s just yours. The upper-level laundry means no more hauling baskets up and down the stairs. Two more bedrooms and a full bath give you room to grow. The lower-level rec room offers extra space for whatever life throws at you—a workout area, movie nights, playroom—tons of options. Plus, there’s a rough-in for a bathroom, so adding one later is easy. Location? Unbeatable. Walk to Creekside shopping and Kernstown Battlefield. Jim Barnett Park and downtown Winchester are just minutes away. This isn’t just a house—it’s the perfect start. Schedule your showing today!

605 Lake Drive, Winchester

$674,000

4 Beds ⋅ 4 Baths ⋅ VAWI2006364 MLS

"Come On Down To Kennedy" This beautiful 4 bedroom, 3 1/2 bath colonial style home sits on a cul-de-sac and backs to the Kernstown Battlefield! As you enter you'll notice the gorgeous hardwood floors. The main level has a formal living room, formal dining room, office, two story family room with a stunning stone gas fireplace, half bathroom, eating area and a breathtaking kitchen with beautiful countertops and stainless steel appliances. Primary bedroom on the upper level with tray ceilings, giant walk-in-closet and a private bathroom with a soaking tub, standing shower and double vanities! 3 additional bedrooms on the upper level, hallway full bathroom as well as a laundry room making your life much easier. Plenty of finished area in the walkout basement with a full bath and unfinished area for storage. Enjoy relaxing evenings on the Trex floored/vinyl sides deck and enjoy the incredible views. Two car garage, spacious porch, patio area out back and a new front walkway just installed in the summer of 2024 along with fresh landscaping. New garbage disposal and dishwasher in 2016. New sump pump with battery backup and hardwired smoke detectors in 2017. New induction cooktop, microwave with outside vent, primary bath toilet, upstairs HVAC system (inside & outside unit), smart thermostats and new caulking in bathrooms in 2019. New roof (with 10 year warranty), sliding door screens (basement and kitchen), self locking high lift garage door and upstairs hallway bathroom toilet in 2020. New washer in 2021 and new dryer in 2022.

937 Kennedy Drive, Winchester

$670,000

5 Beds ⋅ 4 Baths ⋅ VAWI2005432 MLS

NEW PRICE! Perched atop a quiet cul-de-sac in desirable Rolling Hills Estates, this stunning five bedroom home has space for all of your needs! The gourmet kitchen is a chef's dream. It offers a large island, granite countertops, extensive counterspace, upgraded cabinetry, updated light fixtures and a tile backsplash. The added space of the morning room extends the kitchen and provides a bright and open feeling. Coffee bar/butlers pantry lies between the kitchen and dining room. The split staircase is an attractive focal point upon entering the vaulted foyer. Wood flooring, crown molding, shadow box trim adorn the formal living and dining areas. Large family room with gas fireplace sits between the kitchen and office. Upstairs the luxurious primary suite offers sitting room, double closets, soaking tup, separate showers, and dual sinks. Two bedrooms are joined by a Jack and Jill bathroom, while two other bedrooms share a full hall bath. All floors have 9' ceilings. The walkout basement is ready for your finishing touches! It has rough plumbing for a bathroom as well as a sink for a wet bar. Incredible Trex deck offers outdoor entertaining space and back yard is fully fenced. Enjoy walks to Kernstown Battlefield and Creekside Shopping Center.

920 Kennedy Drive, Winchester

$630,000

5 Beds ⋅ 4 Baths ⋅ VAWI2005462 MLS

Nestled within the serene confines of Rolling Hills Estates, this stunning home boasts five bedrooms and four bathrooms, offering spacious living arrangements including a main floor bedroom and full bathroom for added convenience. The open floorplan seamlessly integrates the gas fireplace, hardwood floors, plush carpet, and engineered wood flooring, creating an inviting atmosphere throughout. A finished basement provides additional living space, while outside, a composite deck overlooks the meticulously landscaped yard with enchanting tree-lined views, perfect for outdoor gatherings or peaceful relaxation. This residence harmoniously blends modern comforts with natural beauty, promising a lifestyle of comfort and tranquility.

708 Lake Drive, Winchester

$589,900

4 Beds ⋅ 4 Baths ⋅ VAWI2003958 MLS

Welcome to this stunning 3,400 square foot, single-family home nestled in a quiet neighborhood minutes away from shopping and dining. This meticulously maintained residence offers a perfect blend of modern comfort and timeless elegance: 4 bedrooms and 3.5 baths provide ample space for a growing family or hosting guests. The luxurious master suite features a walk-in shower, soaking tub, double sinks, and a large walk-in closet. Boasting large, custom oak cabinets, the kitchen features pristine granite countertops, stainless steel appliances, and a convenient breakfast bar. Enjoy the warmth and beauty of oak hardwood floors throughout the main level while gathering around the gas fireplace for cozy evenings with family and friends. The elegant dining room is perfect for holiday entertaining and special occasions with stunning windows that fill the room with natural light. A custom built deck offers an inviting space for family barbeques and outdoor enjoyment. Ideal for additional living space, the finished basement provides versatility for a family room, home office, or entertainment area and a separate storage room ensures organization and convenience. The attached 2-car garage not only provides shelter for your vehicles, but also offers space for a workbench and ample storage for yard equipment. Situated on a corner lot in a quiet neighborhood, this home is a rare find that offers a perfect blend of comfort, style, and convenience. Schedule a showing today to experience the charm and warmth of this exceptional property.

808 Lake Drive, Winchester

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