Winchester Homes with Fee Simple Ownership

2 Beds ⋅ 1 Baths ⋅ VAFV2044850 MLS

Tucked away at the end of the neighborhood and surrounded by serene woods, 610 Puma Trl offers the perfect blend of privacy and charm. This adorable 2-bedroom, 1-bath rancher is a true retreat, featuring modern updates and a warm, inviting layout. Enjoy peaceful living with beautiful natural surroundings while still being conveniently located near town. A rare opportunity to own your own slice of quiet, comfortable living.

610 Puma Trl, Winchester

$350,000

3 Beds ⋅ 2 Baths ⋅ VAFV2044840 MLS

Charming 3-bedroom, 2-full-bath Cape Cod situated on .88 acres in a convenient location just minutes from Winchester City. This inviting home offers the flexibility of a main-level bedroom and full bath, along with a cozy wood-burning fireplace that adds warmth and character. Enjoy relaxing or entertaining on the welcoming front porch or side porch, with plenty of outdoor space to enjoy. A standout feature of this property is the large detached barn/garage offering 7 bays—an incredible amount of space for vehicles, equipment, storage, a workshop, hobbies, or recreational toys. With nearly an acre, a versatile floor plan, and exceptional outbuilding space, this property offers a unique combination of convenience, character, and functionality while being extremely close to Winchester.

144 Apple Valley Rd, Winchester

$375,000

3 Beds ⋅ 3 Baths ⋅ VAFV2044836 MLS

With special financing options available, Discover the promise of your future home. This stunning Colonial-style residence all most completed. Move in your new home in just 30 days or less. This property offers a perfect blend of modern design and classic comfort. With three spacious bedrooms and two and a half bathrooms, this home is designed for both relaxation and entertaining. The interior boasts luxurious vinyl plank flooring and cozy carpet, creating a warm atmosphere throughout. An unfinished walkout basement provides endless possibilities for customization, whether you envision a home gym, a cozy den, or additional storage. Enjoy the convenience of upper-floor laundry and a driveway for easy parking. Nestled on a generous 0.27-acre level lot with possible option for expansion, this property invites you to create your own outdoor oasis. Imagine summer barbecues or quiet evenings on your future patio. With its thoughtful design, this home is waiting for your personal touch. Embrace the opportunity to make this house your dream home!

904 Panther Dr, Winchester

$370,000

3 Beds ⋅ 3 Baths ⋅ VAFV2044744 MLS

With special financing options available, Discover the promise of your future home. This stunning Colonial-style residence all most completed. Move in your new home in just 30 days or less. This property offers a perfect blend of modern design and classic comfort. With three spacious bedrooms and two and a half bathrooms, this home is designed for both relaxation and entertaining. The interior boasts luxurious vinyl plank flooring and cozy carpet, creating a warm atmosphere throughout. An unfinished walkout basement provides endless possibilities for customization, whether you envision a home gym, a cozy den, or additional storage. Enjoy the convenience of upper-floor laundry and a driveway for easy parking. Nestled on a generous 0.27-acre level lot with possible option for expansion, this property invites you to create your own outdoor oasis. Imagine summer barbecues or quiet evenings on your future patio. With its thoughtful design, this home is waiting for your personal touch. Embrace the opportunity to make this house your dream home!

902 Panther Dr, Winchester

$499,900

3 Beds ⋅ 3 Baths ⋅ VAWI2011602 MLS

Step into a piece of Winchester history, thoughtfully restored and completely renovated in 2025 while preserving the character and craftsmanship that make this historic home so special. Originally built in 1865, this downtown Winchester property has been extensively updated from top to bottom, blending modern comfort with carefully preserved historic details. The kitchen was returned to its original central location within the home, where restored handmade cabinets were thoughtfully combined with new cabinetry and African Mahogany open shelving. The ceiling was raised and a dormer added to bring in additional natural light, while original brick was exposed on two walls. Reclaimed original wood was given new life throughout the space, creating beautiful beams, trim, and a distinctive vent hood. A dedicated coffee area with bar sink adds both function and charm. The main living spaces were opened up by removing the wall between the entry hall and living room, while the doorway to the restored kitchen was widened to create an inviting, connected floor plan. The fireplace was enhanced with gas logs, and even a trap door adds an unexpected touch of history and character. Original hard pine floors in the living room and kitchen were carefully restored, preserving the warmth and authenticity of the home. A new Dutch door welcomes you at the front entrance. The 2025 renovation also brought extensive structural and mechanical improvements, including a new metal roof, new gas furnace, new air conditioning system, upgraded 200-amp electrical service, and a repointed and reinforced brick foundation. A 22' x 16' addition expands the living space and features durable board-and-batten metal siding. Outdoor living was thoughtfully designed as well, with a new 22' x 10' deck featuring wire railing. The space beneath the deck includes a concrete pad and has been waterproofed, creating additional usable outdoor living space. A separate 22' x 9'9" concrete pad has also been added and prepped for electrical, ready for a future hot tub. From the original brick and restored floors to the reclaimed wood details and preserved architectural elements, small pieces of the home's history have been intentionally saved throughout. Every update was completed with an appreciation for what came before, resulting in a home that feels both historic and fresh. With its downtown Winchester location, extensive 2025 renovation, and rare combination of historic craftsmanship and modern amenities, this is a home that truly offers the best of both worlds.

510 S Cameron St, Winchester

$634,900

5 Beds ⋅ 4 Baths ⋅ VAFV2044776 MLS

Your Next Chapter Starts Here! Space, style, flexibility, and a backyard made for entertaining — all tucked away on a quiet cul-de-sac in desirable Oakdale Crossing. This impressive 5-bedroom, 4-bathroom, three-level Colonial, with new roof (2026), delivers the kind of versatile space today’s buyers are looking for, with room to work from home, host friends, grow your household, or create the ultimate hangout zone. Start with the front wraparound porch, the perfect spot for morning coffee or winding down at the end of the day. Out back, the fun really begins: multiple composite decks with a pergola overlook a private, fully fenced yard backed by mature trees, creating your own outdoor retreat. The 20' x 30' saltwater above-ground pool takes summer entertaining to the next level. Inside, beautiful hardwood floors run throughout the main and upper levels. The main level offers an easy-flowing layout with a welcoming family room featuring a gas fireplace, separate dining and living rooms, plus a spacious kitchen with upgraded countertops, breakfast bar, and breakfast room. The first floor also includes a bedroom and full bathroom — ideal for guests, a home office, or flexible living arrangements. Upstairs, the spacious primary suite feels like a private escape, complete with double sinks, jetted tub, walk-in shower, and walk-in closet. Three additional bedrooms, a full bathroom, and conveniently located laundry complete the upper level. And then there’s the lower level — a huge bonus space ready for whatever your lifestyle demands. The large family room with wet bar is made for movie nights, game days, parties, or a dedicated entertainment space. An additional room plus a full bathroom offers incredible flexibility for a home gym, office, guest suite, teen hangout, or potential in-law setup. Outside your front door, you're conveniently located near Winchester Country Club, shopping, restaurants, and schools, giving you the best of both convenience and neighborhood living. This isn't just a house — it's the space to live the way you want now, with room for whatever comes next.

314 Huntersridge Rd, Winchester

$35,000

VAFV2044820 MLS

Lot 112, 113, & 114 .40 acre per Lot. Certification letters for each. Lot 112 - 3 Bdrm Perc / Lot 113 - 4 Bdrm Perc / Lot 114 - 3 Bdrm Perc. These lots Have the Views !! Come Build your part or full time Dream Home. Located in Shawneeland with No HOA, enjoy the amenities, Large Recreational Park Area with fishing ponds connected by running streams, Playground, Picnic Pavillion(s), Basketball hoops, Tuscarora Trails, Cherokee Lake w/beach & fishing area, Swan Lake for fishing, Another Park Area w/ playground on Maple Trail. Hard top roads. Common grounds & Road maintenance & plowed in Winter. Shawneeland is a Sanitary District Fee is included in Real Estate Tax Bill. Live Rural with a short distance to Shopping, Hospital and Town. Seller is Motivated, will consider selling lots separate.

Lot 112-113-114 Tomahawk Trl, Winchester

$4,000

VAFV2044816 MLS

Lot 60 .42 acre Certification letter for 3 Bdrm Perc. Talk about view! Come Build your part or full time Dream Home. Located in Shawneeland with No HOA, enjoy the amenities, Large Recreational Park Area with fishing ponds connected by running streams, Playground, Picnic Pavillion(s), Basketball hoops, Tuscarora Trails, Cherokee Lake w/beach & fishing area, Swan Lake for fishing, Another Park Area w/ playground on Maple Trail. Hard top roads. Common grounds & Road maintenance & plowed in Winter. Shawneeland is a Sanitary District Fee is included in Real Estate Tax Bill. Live Rural with a short distance to Shopping, Hospital and Town. Seller is Motivated.

Lot 60 Tomahawk, Winchester

$471,000

3 Beds ⋅ 3 Baths ⋅ VAWI2011610 MLS

A must see property! This is a beautifull well kept colonial house with 3 bedrooms, 2 full bath and 1 half bath. The basement is unfinish but is ready to be build. As you enter the main level, you will see a nice welcoming livingroom, diningroom and beautiful granite countertops in the kitchen, with stainless steel appliances and high effitiency washer and dryer to the side. From the kitchen you can easily walkout to a huge concrete patio for a great family cookout and joyful huge backyard. The back yard is infenced with 6ft tall white vinyl privacy fence that makes it look very elegant and secured... In the upper level of the house, you will find the masterbedroom with a masterbath, and a second bath for the 2 other bedroom. This property is minutes away from the Winchester Historic downtown and a short drive to Shenandoah University. This is a well kept property and is waiting for you to make it yours! Schedule your showing online and allow time since the seller has two little dogs to take care off when you go show it. There are video cameras at the property.

421 Longview Ave, Winchester

$525,000

4 Beds ⋅ 4 Baths ⋅ VAFV2044810 MLS

Offering three luxuriously finished levels, extensive upgrades, and a backyard designed for entertaining, this 4 bed/3.5 bath colonial is a MUST-SEE! Step inside to a grand foyer with soaring 12-foot ceilings and walls of windows flooding the home with natural light throughout. The main level features a dedicated study room accented by striking arched windows, spacious living and dining areas, an open kitchen with a window overlooking the serene backyard, and a showstopping family room wrapped in eight oversized windows with transoms that frame views of the outdoors and create a bright, airy gathering space centered around a cozy fireplace. Step outside to your own backyard retreat—an entertainer’s dream with an expansive, fully fenced lawn, large low-maintenance composite deck, spacious brick patio, and custom-built outdoor brick fireplace. Imagine summer cookouts on the deck, evenings around the fire, or simply enjoying the abundance of your own private open space. Upstairs, the expansive primary suite feels like a retreat of its own, featuring a separate sitting area perfect for a reading nook or quiet place to unwind, and two walk-in closets, including one conveniently located within the ensuite bath. The spacious primary bath features dual vanities, an oversized walk-in shower, private water closet, and dedicated space ready to add the relaxing soaking tub of your dreams. The upper level is completed by three additional spacious bedrooms with ample closet space, including one with its own walk-in closet, plus an LG washer and dryer conveniently tucked behind closed doors in the hallway for out-of-sight laundry. Head downstairs to the fully finished basement, offering even more versatile living space with a spacious recreation room and full bathroom next to a bonus room with generous closet space—giving you the flexibility to create the guest space, media room, playroom, home gym, or hobby space that fits your lifestyle. The home’s biggest-ticket improvements have already been taken care of, saving you thousands in future costly upgrades! Updates include a newer roof and siding, HVAC systems, water heater, upgraded insulation, sump pump, irrigation system, water softener, radon mitigation system, and whole-house generator, providing the ultimate peace of mind and backup power when the neighborhood experiences an outage. This home presents a RARE OPPORTUNITY, priced significantly below the tax assessed value. Seller welcomes ALL offers—bring yours and make this home your own!

114 Nassau Dr, Winchester

$299,500

3 Beds ⋅ 2 Baths ⋅ VAWI2011582 MLS

Fresh, stylish, and move-in ready! Welcome to 621 Watson Avenue, a beautifully refreshed 3-bedroom, 1.5-bath duplex offering a wonderful blend of classic character and modern updates. Step inside to find freshly painted walls and beautiful hardwood floors that create a bright, inviting atmosphere throughout the main living areas. The updated kitchen features new cabinetry and stainless steel appliances, creating a clean, contemporary space perfect for everyday living and entertaining. Both bathrooms have also been thoughtfully updated, adding to the home’s fresh and modern appeal. Enjoy your morning coffee or unwind at the end of the day on the covered front porch. The partially fenced yard provides space to enjoy the outdoors, while the storage shed offers convenient additional space for tools, lawn equipment, and seasonal items. Convenient rear-entry parking provides easy access to the home, with additional street parking available in front. The unfinished basement provides valuable additional storage and utility space. With its attractive updates, functional floor plan, outdoor space, storage shed, and convenient parking, 621 Watson Avenue is a standout opportunity in Winchester! Whether you're searching for a comfortable place to call home or a great investment property, this beautifully refreshed duplex is ready for its next owner. Schedule your tour on ShowingTime today and see why 621 Watson Avenue stands out! ***Seller finishing final touches, ready for tours starting 9/15/26.

621 Watson Ave, Winchester

$349,999

4 Beds ⋅ 2 Baths ⋅ VAFV2044756 MLS

Welcome to 120 Comanche Trail in Shawneeland! Offering over 1,800 finished sq. ft., this 4-bedroom, 2-bath home combines thoughtful updates with plenty of space inside and out. Recent improvements include a NEW roof, newer HVAC, new flooring, fresh paint, updated lighting, and updated bathrooms. The primary bedroom features a walk-in closet and private en-suite bath, creating a comfortable retreat. The fully finished walkout basement expands the living space with a huge additional bedroom, bonus room and plenty of storage. Ideal for guests, a home office, recreation space, or multi-generational living. Outside, enjoy a large private lot surrounded by mature trees with established garden beds and a fire pit. A 1-car garage and spacious driveway provide plenty of parking for guests. Located on the lower end of Shawneeland, approximately 15 minutes from Winchester Medical Center, Downtown Winchester, shopping, dining, and major commuter routes. Community amenities include a lake, private beach, playgrounds, sports fields, and more. NO HOA - Shawneeland is a sanitary district maintained by Frederick County. The septic system was completely redone in November of 2024 for additional buyer peace of mind. Updated, spacious, private, and conveniently located—this home is ready for its next owner!

120 Comanche Trl, Winchester

Winchester Homes with Fee Simple Ownership

Newest Winchester Homes with Fee Simple Ownership