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

$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 huge concrete patio for a great family cookout and enjoy the huge backyard. The back yard is infenced with 6ft tall white vinyl privacy fence that makes it look very elegant and secure...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
$479,900
5 Beds ⋅ 3 Baths ⋅ VAFV2044802 MLS
This lovingly maintained two-owner Colonial has been thoughtfully cared for and improved since 1994, offering the character of an established home with many of the updates today's buyers are looking for. Homes in this sought-after neighborhood rarely come to market, making this a special opportunity in one of the area's most convenient commuter locations. Inside, you'll find a comfortable blend of hardwood, tile, and carpet flooring, built-in shelving, fresh paint in many areas, and charming details including chair rail and crown molding in select rooms. The living area features an antique stained-glass mantle that has been beautifully refinished and incorporated above the gas fireplace, creating a distinctive focal point. Upstairs, four large bedrooms provide plenty of comfortable living space, including a spacious primary bedroom with its own private bathroom. A finished and conditioned third-floor loft adds a huge, flexible bonus space ready to meet your needs; perfect for a 5th bedroom, playroom, office, game room, or additional living area. Storage abounds throughout this versatile space, offering possibilities to suit a variety of lifestyles. The kitchen is designed for both everyday living and entertaining, with an oversized island offering abundant storage, a butcher block top, and an eat-up bar area. Granite countertops are complemented by a white subway tile backsplash and a dramatic floor-to-ceiling accent wall. Recent improvements include a new water softener, a 2018 water heater, and a new washer and dryer installed in 2026. The HVAC systems are approximately two and three years old and have been recently serviced. The roof is less than five years old, while newer HardieBoard siding and windows provide additional peace of mind. Step outside to the large covered rear porch, finished with beadboard and a ceiling fan, overlooking the spacious fenced backyard. Mature trees and established landscaping create a private setting that is ideal for relaxing, entertaining, or enjoying outdoor time. The paved driveway adds convenience, while the no-HOA neighborhood provides added flexibility. Perfectly positioned close to town, schools, and everyday amenities while offering quick access to Route 7 for commuters, this home combines a well-established neighborhood setting with an exceptionally convenient location. A home with genuine character, meaningful improvements, and a level of care that is evident throughout.

109 Julee Dr, Winchester
$459,900
3 Beds ⋅ 2 Baths ⋅ VAFV2044768 MLS
Enjoy easy one-level living in this well-maintained ranch home conveniently located in Winchester, close to commuter routes, shopping, restaurants, and everyday amenities. The inviting front porch is the perfect spot to relax and enjoy warm evenings. Inside, hardwood floors flow through the living room, kitchen, and dining area, while the bedrooms feature comfortable carpeting. A dedicated laundry room adds convenience, and the unfinished basement provides plenty of storage and future possibilities. Step outside to the backyard, where a deck offers the perfect setting for entertaining, relaxing, or enjoying outdoor gatherings. A shed provides additional storage, while the two-car garage offers plenty of parking and workspace. A great combination of comfort, convenience, and outdoor living!

991 Front Royal Pike, Winchester
$325,000
4 Beds ⋅ 2 Baths ⋅ VAWI2011592 MLS
Welcome home! This beautifully maintained two-level home offers 4 bedrooms and 2 full bathrooms in the heart of Winchester. Warm and inviting, the home features a comfortable, functional layout with classic charm and thoughtful updates throughout. Pride of ownership is evident in every detail, both inside and out. Enjoy spacious living areas, a fully fenced yard perfect for relaxing or entertaining, and a private driveway for convenient off-street parking. Ideally located close to downtown Winchester, shopping, dining, and commuter routes. Move-in ready and waiting for you to make it your own!

805 S Kent St, Winchester
$3,500,000
VAFV2044790 MLS
Be sure to see the video and 3D tour to fully explore this property! <br><br> Award-Winning Virginia Winery + Luxury Vineyard Estate + Income-Producing Luxury Short Term Rental + Development Lots! <br>br> **Briede Family Vineyards** presents an exceptional opportunity to acquire one of Virginia's distinguished boutique vineyard estates. Offering far more than beautiful real estate, it provides the new owners the opportunity to continue a well-established legacy within the Commonwealth's thriving wine industry. Combining an award-winning vineyard and winery brand with an elegant country residence currently operating as a licensed short-term rental, this remarkable property is ideally suited for those seeking both a lifestyle investment and an established business. The property's total acreage also includes three additional building lots (with approved Well and Septic), providing exceptional opportunities for future residential development, guest accommodations, or investment, subject to applicable approvals.<br><br> For years, Briede Family Vineyards has earned recognition for producing award-winning wines while cultivating a reputation for offering intimate, highly personalized guest experiences. Unlike larger commercial wineries, the vineyard has become known for its thoughtfully curated tastings, signature Champagne experiences, and imported French cheese pairings, creating a destination that guests return to year after year. The recognized brand, loyal clientele, and respected presence within Virginia's wine community provide an invaluable foundation for future ownership.<br><br> The beautifully appointed tasting room and adjoining great room provide an inviting setting for tastings, private gatherings, and special events. Guests can also enjoy the charming covered pavilion overlooking the vineyard, offering an ideal outdoor venue for relaxing, live entertainment, special events, and taking in the surrounding views. Complementing the vineyard experience, the beautifully maintained residence offers guests the opportunity to experience life among the vines. Surrounded by sweeping vineyard vistas and tranquil countryside, the home serves equally well as a private estate residence, luxury guest accommodations, or an expanded hospitality venue, offering exceptional flexibility for a variety of ownership goals.<br><br> The property encompasses established vineyards, meticulously maintained grounds, and the infrastructure necessary to continue current operations while providing opportunities for future growth. This is a true turnkey opportunity, allowing a new owner to step into an established vineyard operation with recognized branding and a well-developed hospitality experience, while providing an exceptional foundation for future growth and continued success. Whether expanding wine production, enhancing agritourism, hosting private events, or preserving the vineyard's boutique character, the possibilities are exceptional.<br><br> Conveniently located in Frederick County, Virginia, with easy access to Northern Virginia, Washington, D.C., and the Shenandoah Valley, Briede Family Vineyards represents a rare opportunity to acquire a recognized vineyard destination where years of dedicated ownership, reputation, and hospitality come together in one remarkable offering.

Winchester
$552,000
4 Beds ⋅ 3 Baths ⋅ VAFV2044754 MLS
Beautifully remodeled Colonial in Pioneer Heights. Designed with primary suite; ideal home office configuration. All large bedrooms, large hardwood living room with stone wood fireplace, new natural gas upstairs furnace and a/c, upgraded insulation in attic, oversized garage and large deck. New paint, LVPk flooring in baths and kitchen. Must see.

100 Winns Cir, Winchester
$395,600
4 Beds ⋅ 2 Baths ⋅ VAFV2044446 MLS
You are going to love this spacious, one-level ranch located on a half-acre lot in a great location! Here are some of the key features and recent updates: - Huge 20x26 family room with Red Oak hardwood floors, a brick fireplace, and newly replaced French doors that open onto a large L-shaped front deck. - Bedrooms & Baths: New paint and new flooring throughout bedrooms and bathrooms master bath features a new vanity and new ceramic tile flooring, which is also featured in the hallway bath. master bedroom has full bath -Laundry: 8x8 laundry room complete with washer, dryer, cabinets, and counter space. -Kitchen and living room has Bruce flooring All new painting through out house - Upgrades: New ceiling fans in all rooms. The water pump, septic tank, and attic air handler for the AC unit have all been replaced. Both decks have been recently remodeled and resealed. - Garaging & Parking: you are going to love the Oversized 20x28 garage with front and back entry doors, plus a second attached 12×20 garage with entry door from the main garage! Large driveway with a 10+ car capacity and turnaround area. - Outdoor Space: Fenced backyard with a 10x12 back deck and beautiful pastoral views in both the front and back. Large L-shaped deck on front of house This home offers peaceful country living while remaining convenient to local grocery stores, restaurants, gas stations, schools, and major commuter routes this ranch offers the space & amenities you been dreaming of....... LOOK NO FURTHER!

178 Payne Rd, Winchester
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