Winchester Homes with Fee Simple Ownership

Winchester Homes with Fee Simple Ownership

Welcome to Winchester, Virginia – a charming city steeped in rich history and vibrant culture. Nestled in the picturesque Shenandoah Valley, Winchester is known for its stunning landscapes, historic architecture, and a warm, welcoming community. With a population of just over 27,000 residents, this quaint city offers a perfect blend of small-town charm and modern amenities, making it an ideal place to call home.

Winchester boasts a plethora of outdoor activities, with nearby parks and trails that invite residents to explore the natural beauty of the region. The city is also home to a lively downtown area filled with unique boutiques, delightful eateries, and cultural attractions, including the Museum of the Shenandoah Valley and the historic Old Town. Winchester’s rich history is palpable, with well-preserved buildings and landmarks that tell the story of its past.

For those considering a move to this enchanting city, Winchester offers an array of homes with fee simple ownership. This means that homeowners have full ownership of their property, including the land it sits on, providing a sense of security and investment. Whether you’re seeking a charming historic home, a modern townhouse, or a spacious family residence, Winchester has something to suit every taste and budget.

Experience the best of Virginia living in Winchester, where community spirit thrives, and every day feels like a step back in time. Discover your dream home in this captivating city, and embrace the lifestyle that awaits you!

Newest Winchester Homes with Fee Simple Ownership

$399,000
3 Beds ⋅ 2 Baths ⋅ VAFV2043750 MLS
Situated directly across from historic Third Battle of Winchester Park, this charming brick ranch offers a rare opportunity to enjoy more than six miles of scenic walking trails, interpretive markers, and historic monuments just steps from your front door. Conveniently located with quick access to Routes 7, 11, and I-81, the property combines peaceful surroundings with exceptional accessibility. Set on approximately 2.37 mostly level, usable acres, the property provides plenty of space for gardening, outdoor recreation, or future expansion. The home features more than 1,300 square feet of living space on the main level, plus an additional 1,300-square-foot basement, offering endless possibilities. Inside, you'll find three bedrooms, one full bath, and original hardwood floors in the family room and bedrooms, all ready for your personal updates and finishing touches. The full walk-out basement, with its separate exterior entrance, expands the home's potential for additional living space, a recreation room, home office, or workshop. Partially finished and previously used as a recreation area, it also includes a large unfinished section with built-in shelving for exceptional storage or hobby space. Owned by the same family since it was built, this well-constructed home features a timeless brick exterior, an attached carport, a spacious rear deck, and several outbuildings ideal for storing lawn equipment, gardening tools, or outdoor gear. With solid construction, a functional layout, beautiful acreage, and an unbeatable location across from one of the area's most treasured historic parks, this property is brimming with potential and ready for its next chapter. Whether you're looking for a peaceful place to call home or an opportunity to create your dream property, this is one you won't want to miss.

735 Redbud, Winchester
$775,000
4 Beds ⋅ 4 Baths ⋅ VAFV2043652 MLS
Welcome to this exceptional 4-bedroom, 3.5-bath Colonial in the sought-after Raven Pointe subdivision, where luxury living extends well beyond the front door. The backyard is a true showstopper, featuring a one-year-old 20' x 40' heated Hayward OmniLogic saltwater pool with a tanning ledge, sunken spa, and Coverstar automatic safety cover. A covered Trex deck with a porch swing overlooks the private backyard, creating the perfect space for relaxing or entertaining. Inside, the main level offers a private home office with custom built-ins, a formal dining room, a spacious family room with a gas fireplace, and a beautifully appointed kitchen featuring a large center island, butler's pantry, stainless steel appliances, gas cooking, and a bright breakfast room. Upstairs, the spacious primary suite includes luxury vinyl plank flooring, a walk-in closet, and a spa-like bath with a jetted tub, walk-in shower, and dual vanities. Three additional bedrooms, a versatile bonus room, and an upper-level laundry room complete the second floor. The finished walk-up basement is made for entertaining with a large recreation room, wet bar with a built-in ice maker, full bath, storage room, and a flexible bonus room that can serve as a fifth bedroom, home gym, or office. Located in Raven Pointe with sidewalks and streetlights, this home is just minutes from shopping, dining, schools, and commuter routes. Offering an incredible combination of elegant living spaces and a resort-style backyard, this is a home you won't want to miss.

107 Cahille Dr, Winchester
$719,000
7 Beds ⋅ 5 Baths ⋅ VAWI2011262 MLS
Situated on a prominent corner lot in an exclusive cul-de-sac enclave of distinguished homes, this impressive stone-front residence offers exceptional space, comfort, and timeless appeal in one of the area’s most desirable neighborhoods. Ideally located near fine dining, shopping, banks, and everyday conveniences, the home combines luxury living with unmatched accessibility. Built in 2011 and meticulously maintained, freshly painted, with new wall to wall carpet, this expansive residence features 7 bedrooms and 5 full bathrooms thoughtfully designed for both elegant entertaining and comfortable everyday living. A dramatic two-story foyer creates a grand first impression, flanked by formal living and dining rooms that add sophistication and charm. The upper level includes a luxurious owner’s suite with a spacious bedroom and spa-inspired bath, along with generously sized secondary bedrooms, including a Jack-and-Jill bath and an additional hall bath arrangement designed for convenience and privacy. The main level offers a desirable guest suite with a full bath, ideal for multigenerational living or visiting guests. At the heart of the home is a beautifully appointed gourmet kitchen featuring upgraded cabinetry, granite countertops, a center island, breakfast area, and seamless flow into the expansive family room. The finished lower level provides exceptional versatility with a large recreation/family room, an additional suite, and three flexible rooms perfectly suited for guest accommodations, home offices, fitness space, or playrooms. Step outside to the inviting deck overlooking the gently rolling backyard — an ideal setting for relaxing mornings, outdoor dining, and entertaining in a peaceful, private setting. House blueprints provided in this listing are for reference only and may not accurately reflect the current structure. Call your real estate agent and schedule a showing today!

2700 Loyalty Ct, Winchester
$359,900
3 Beds ⋅ 1 Baths ⋅ VAWI2011258 MLS
Welcome to this beautifully updated brick home offering the perfect blend of charm and modern updates. Major improvements completed in 2021 include a new roof, windows, HVAC system, kitchen cabinets with granite countertops, and a renovated main-level bathroom. A new water heater was installed in 2024. In 2026, a city-permitted addition created a spacious new primary bedroom and bathroom, along with new roof framing, siding, and plumbing. Conveniently located close to shopping, dining, and commuter routes, this move-in-ready home is ready for its next owner. Chimney is sealed off. Not useable. *Agent is related to landlord* The information contained herein is for informational purposes only. RE/MAX Roots makes no representation as to the accuracy or reliability of the information. The buyer is to verify information provided and related to the property that is material to a buyer’s decision to purchase the property. All documents and other information attached to this listing are provided as a courtesy and should be researched and verified by the buyer agent.

236 Shawnee Ave, Winchester
$349,000
3 Beds ⋅ 3 Baths ⋅ VAFV2043742 MLS
Nestled in the serene Wilde Acres/Mtn Falls community, this exquisite split foyer home, built in 2020, offers a harmonious blend of modern luxury and natural beauty. Spanning a generous 0.78 acres, the property is enveloped by lush trees, providing a tranquil backdrop that enhances the sense of privacy and peace. Step inside to discover a warm and inviting interior, where laminated flooring flows seamlessly throughout the main living areas. The heart of the home features a spacious living room that effortlessly connects to a well-appointed kitchen, complete with ENERGY STAR appliances, including a built-in microwave, refrigerator, and stove. The pantry offers ample storage, ensuring that your culinary adventures are always well-equipped. With three thoughtfully designed bedrooms and two and a half bathrooms, this residence caters to both comfort and functionality. The master suite is a true retreat, boasting an en-suite bathroom that exudes elegance. The additional bedrooms are versatile, perfect for guests, a home office, or creative spaces. The partially finished basement, accessible via a side entrance, presents endless possibilities-whether you envision a cozy family room, a home gym, or additional storage. The attached two-car garage, featuring a side entry and built-in access, adds convenience to your daily routine. Outside, the expansive lot invites you to embrace the outdoors. Imagine sipping your morning coffee on a private patio, surrounded by the soothing sounds of nature, or hosting gatherings under the shade of towering trees. The level yard is perfect for gardening, play, or simply enjoying the picturesque mountain views that stretch beyond your property. This home is not just a residence; it's a lifestyle. With road maintenance and snow removal included in the association fee, you can enjoy the beauty of the changing seasons without the hassle of upkeep. The surrounding area offers a wealth of outdoor activities, from hiking to exploring nearby parks, making it an ideal setting for those who appreciate an active lifestyle. Experience the perfect blend of luxury, comfort, and nature in this stunning home, where every detail has been thoughtfully curated to create a sanctuary you'll be proud to call your own.

204 Cougar Trl, Winchester
$700,000
4 Beds ⋅ 4 Baths ⋅ VAFV2043616 MLS
Welcome home to this gorgeous custom-designed residence offering exceptional one-level living with quality craftsmanship and thoughtful details throughout. A welcoming foyer with an elegant tray ceiling sets the stage for the beautiful interior. The stunning gourmet kitchen is the heart of the home, featuring a large center island with leathered granite countertops, abundant soft-close cabinetry and drawers, Café-style stainless steel appliances, and generous counter space for cooking and entertaining. The spacious dining area showcases a tray ceiling and sliding glass doors that open to a screened-in covered porch, creating the perfect setting for relaxing or entertaining. The impressive living room features a soaring vaulted ceiling with exposed wood beams, a beautiful fireplace with a custom mantel, and large tinted windows that flood the space with natural light while enhancing energy efficiency and privacy. The private owner's suite is a luxurious retreat featuring a tray ceiling, two walk-in closets, and a spa-inspired en-suite bath with a double-sink vanity, linen closet, and a custom-designed tiled walk-in shower with a built-in seat. The desirable split-bedroom floor plan offers two additional generously sized bedrooms and a well-appointed hall bath with a tub/shower combination, providing comfort and privacy for family and guests. The walk-out lower level is truly in a class of its own and showcases the same exceptional craftsmanship and attention to detail found throughout the home. Filled with abundant natural light, this incredible space features a spacious family room, an attractive wet bar, a private bedroom, a full bath, dedicated office space, and a versatile bonus room currently used as a music room with a full-size window. A large unfinished storage area provides ample room for all your storage needs. Step outside to the concrete patio and unwind while listening to the peaceful sounds of the beautifully designed waterfall nestled within the professionally landscaped backyard. Gorgeous natural stone, thoughtfully planned landscaping, and mature plantings create a tranquil outdoor oasis that perfectly complements this remarkable home. While the photographs beautifully capture this home's stunning features, they simply cannot convey the warmth, quality, and craftsmanship you'll experience in person. This is a home that must be seen to be fully appreciated.

151 Feed Mill Ct, Winchester
$399,000
4 Beds ⋅ 2 Baths ⋅ VAFV2043114 MLS
This charming brick ranch-style home, built in 1971, offers a perfect blend of comfort and functionality. With 2,198 sq. ft. of thoughtfully designed space, this residence features three inviting bedrooms and two full bathrooms, ideal for relaxation and privacy. The traditional floor plan is enhanced by beautiful hardwood and ceramic tile flooring, creating a warm and welcoming atmosphere throughout. The heart of the home is the eat-in kitchen, including a built-in microwave, dishwasher, and electric oven/range. Enjoy cozy meals at the kitchen table or gather around the wood-burning/woodstove & propane fireplace in the living area, perfect for creating lasting memories. Additional features include built-ins, ceiling fans, and a convenient main floor laundry area. Step outside to discover a generous 0.74-acre lot, beautifully landscaped and backing onto serene trees, providing a peaceful retreat. The exterior boasts several porches and ample parking with an oversized attached 5-bay garage and paved/gravel driveway, which is fantastic for car enthusiasts! Located in a rural setting, this home offers picturesque views of the garden and surrounding woods, making it an ideal escape from the hustle and bustle. With its combination of comfort, space, and natural beauty, this property is ready to welcome you home. This is a Special Warranty Deed sale. Call for details on garage measurements!

820 Cedar Grove Rd, Winchester
$349,900
2 Beds ⋅ 1 Baths ⋅ VAFV2043734 MLS
The Perfect Starter or downsize Home Awaits! Current Shawneeland Inventory 208 Beaver Trail 101 Tonto Trail 212 Falcon Trail 211 Inca Trail 107 Pinto Trail 123 Killbuck Trail Comcast/Xfinity available on this street. New plan on almost 1/3 of acre! Affordable new home close to town with full unfinished basement (ruff in future bath) for future needs. Upgrades include: Hardwood floors throughout, tile in bath floors, granite countertops kitchen, upgraded cabinets. Builder upgrade full front covered porch and to be Timbertech. Why buy a townhome when you can have your own home! Discover an incredible opportunity to own a brand-new, single-family home on over 1/3 of an acre, offering unparalleled privacy on short street with little traffic and flat lot. This affordable new construction provides the space and freedom you won't find in a townhome. Key Features & Upgrades: Premium Location: Private, expansive lot (1/3+ acre) located low within a desirable community. Quality Finishes: Enjoy hardwood flooring throughout the main living areas, elegant tile in all bathroom floors, granite countertops in the kitchen, and upgraded cabinetry. Outdoor Living: Relax on the stunning, full front covered porch, upgraded with durable, low-maintenance Timbertech decking. Future Potential: A full, unfinished basement provides a blank canvas for future expansion, storage, or customization to meet your evolving needs. Convenience: Just minutes from town, offering easy access to amenities while maintaining a peaceful residential setting. This home is designed for modern living and exceptional value.

101 Tonto, Winchester
$325,000
3 Beds ⋅ 3 Baths ⋅ VAFV2043712 MLS
Rare end-unit townhome situated on one of the community's desirable homesites, backing to mature trees for exceptional privacy. This spacious three-level home offers an open-concept main level featuring a bright living room, an expansive kitchen with center island, stainless steel appliances, abundant cabinetry, and a dining area with direct access to an oversized composite deck overlooking the wooded backyard. Upstairs you'll find a generous primary suite with walk-in closet and private bath, two additional bedrooms, a full hall bath, and convenient bedroom-level laundry. The entry level includes an attached garage, ample storage, and walkout access to a covered patio. Enjoy the perfect combination of indoor and outdoor living with peaceful wooded views—all just minutes from shopping, dining, schools, and major commuter routes.

280 Sage Cir, Winchester
$525,000
5 Beds ⋅ 4 Baths ⋅ VAFV2043592 MLS
Nestled in the charming Apple Ridge community, this stunning Colonial-style home offers a perfect blend of comfort and elegance. Set on a generous 0.4-acre lot, the property backs onto serene open common areas and lush trees, providing a tranquil retreat right in your backyard. Enjoy the luxury of multiple balconies, a spacious deck, and a welcoming porch, ideal for relaxing or entertaining while soaking in the peaceful views of nature. With five spacious bedrooms and four full bathrooms, this home is designed for both relaxation and functionality. The fully finished basement with Kitchen adds extra living space. The main floor laundry adds convenience to your daily routine, while the attached front-entry garage ensures easy access and ample parking. The Apple Ridge neighborhood is known for its friendly atmosphere and community spirit. Excellent local schools are just a short drive away, making this location ideal for those seeking a nurturing environment. With a personal in-ground pool, this home invites you to create lasting memories during warm summer days. Experience the best of suburban living, where comfort meets community, and make this beautiful property your new home. Plus, Solar panels provide a renewable source of energy and much lower electricity bills. Home also includes a whole house water filtered system. Schedule your showing online today. Photos will be done early this week.

144 Morning Glory, Winchester
$375,000
3 Beds ⋅ 1 Baths ⋅ VAFV2043688 MLS
Enjoy one-level living with 6.44 partly wooded acres. All-brick 3-bedroom, 1-bath home offering a peaceful country setting with plenty of room to enjoy the outdoors. Relax on the covered rear porch overlooking the property. The home features a paved driveway and a full unfinished basement, providing excellent storage or future expansion potential. New water heater installed in 2022. A wonderful opportunity for those seeking privacy, acreage, and the durability of an all-brick home. Be sure to check out our 3-D tour attached to this listing!

1480 Chestnut Grove Rd, Winchester
$290,000
3 Beds ⋅ 2 Baths ⋅ VAFV2043682 MLS
Be the first to introduce your buyers to this well-maintained end-unit townhome in one of Winchester’s most convenient commuter locations. Situated at 316 Copperfield Lane, this 3-bedroom, 1.5-bath home, built in 2002, offers comfortable, low-maintenance living just minutes from Valley Mill Road, Route 7, and I-81. Ideal for first-time homebuyers, downsizers, or investors, this property is truly move-in and rental ready. The main level offers a functional, open flow between the living room, dining area, and kitchen, creating a comfortable space for everyday living and entertaining. A conveniently located laundry closet sits just off the kitchen, while a half bath completes the main level. Upstairs, you’ll find all three bedrooms, including a spacious primary bedroom featuring a walk-in closet. A full bathroom serves the upper level, providing a practical layout for families, guests, or roommates. Recent improvements include a recently replaced water heater, refrigerator, and a newly fenced backyard (scheduled for August 13), creating an inviting outdoor space complete with an existing deck and exterior storage shed. The sale includes all major appliances: washer, dryer, refrigerator, dishwasher, microwave, garbage disposal, and gas range, making for a seamless transition for its next owner or tenant. Parking is a standout feature, with two assigned parking spaces directly in front of the home plus two adjacent guest spaces, offering convenience that’s hard to find in many townhome communities. The HOA fee includes water, sewer, and trash service, helping keep monthly ownership costs predictable and affordable. If you have buyers looking for an affordable home in a prime commuter location or an investor searching for a turnkey long-term rental opportunity, be sure to schedule your tour now - this one won’t last long!

316 Copperfield Ln, Winchester
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