Forest Hills Homes For Sale In Winchester City

3 Beds ⋅ 2 Baths ⋅ VAWI2010698 MLS ⋅ CLOSED Status

Well-maintained 3 bed/2 bath rancher just blocks from Jim Barnett Park and close to schools, shopping, dining, and entertainment. Hardwood flooring throughout the main level. Spacious eat-in kitchen with a skylight , featuring Corian countertops, center island, pantry, and additional storage closet. Separate formal dining room. Relax on the 20x6 covered front porch or the 12x16 covered rear deck overlooking the fenced backyard. Property also includes a 14x22 one-car garage and a 12x12 storage shed. The finished lower level offers additional living space with a family room, den, full bath, storage area, and laundry room with utility sink and storage closets. Major updates include roof and shed roof replaced in 2025, HVAC/furnace/heat pump 2020, water heater 2017, gutter guards and updated porch roof 2024, basement LVP flooring 2022, refrigerator 2025, microwave 2024, dishwasher 2019, and replacement windows 2003. Driveway sealed in 2020 and HVAC last serviced 4/2026. Check out the attached 3-D tour!

1115 Opequon Avenue, Winchester

$220,000

3 Beds ⋅ 1 Baths ⋅ VAWI2011078 MLS ⋅ ACTIVE Status

Opportunity on Opequon! Flip, rental potential or primary occupancy for the right buyer. Ranch style home on an unfinished basement in an established community just across the street from Jim Barnett Park and Shenandoah University. A very walkable Winchester City location. Could likely add a half bath in one of the existing closets in the primary bedroom with little hassle. Potential for 4th bedroom, with true egress, in the basement. Basement also offers exterior entrance. Looks to be plenty of room in the panel. 2018 water heater. Sold as is/where is.

1000 Opequon Ave, Winchester

$275,000

3 Beds ⋅ 1 Baths ⋅ VAWI2010454 MLS ⋅ CLOSED Status

Adorable ranch home ready for new owners! The home has a large family room for entertainment, a rear patio for outside relaxation, and a fully fenced yard. Laminate flooring throughout the home with carpet in the family room. The price has been increased to reflect recent upgrades, including a fully remodeled bathroom, refinished kitchen cabinets, new countertops, fresh interior paint throughout the home, and newly painted exterior wood trim. The home is located downtown within close proximity to shopping, restaurants, Jim Barnett Park, and Shenandoah University. Roof replaced in 2019. Owners are licensed agents.

332 Opequon Avenue, Winchester

$295,000

3 Beds ⋅ 1 Baths ⋅ VAWI2010992 MLS ⋅ COMING SOON Status

Ideally situated just minutes from I-81 and a short drive to historic Old Town Winchester, this centrally located rambler offers both convenience and investment potential. Situated on a desirable corner lot, the property features a fenced yard and a storage shed for added functionality. The home has been recently refreshed with new paint and landscaping, providing excellent curb appeal and a well-maintained appearance. Whether you're looking to expand your investment portfolio or secure a future owner-occupied residence, this property presents a great opportunity. A tenant is currently in place through November 8, 2026, paying below market value, with potential for future rent increases. Enjoy immediate rental income and long-term upside in a sought-after location.

405 Shenandoah Ave, Winchester

$265,000

3 Beds ⋅ 2 Baths ⋅ VAWI2010088 MLS ⋅ CLOSED Status

Conveniently located in Winchester City, this 3-bedroom, 1.5-bath ranch-style home features a primary bedroom with a private half bath, two additional bedrooms, and a hall bath. The spacious living room opens to the dining area and kitchen, creating a comfortable flow for everyday living. The kitchen includes a newer refrigerator. Step outside to a screened-in back porch overlooking the level, fenced backyard with a shed for additional storage. Off-street parking is available with an asphalt driveway. A newer hot water heater adds additional value and peace of mind.

320 Opequon Avenue, Winchester

$344,900

2 Beds ⋅ 2 Baths ⋅ VAWI2010584 MLS ⋅ ACTIVE Status

"Beautifully Renovated On Pall Mall St." This 2-bedroom, 2-full bath ranch style home is ready for you to move right in! Home has been completely painted on the inside, and the outside brick/concrete, side handrails, outside/inside of doors have been freshly painted. The kitchen has new granite counters, new sink & faucet, new LVP flooring and new stainless-steel appliances. Huge family room with a large wood burning fireplace, two new windows, a new storm door, new LVP flooring, new baseboard heaters, new window A/C unit and remodeled full bathroom off of it. Both bedrooms have gorgeous, refinished hardwood floors that continue down the hall area and into a living room and dining room. Hallway bathroom has new LVP flooring, new window, new toilet and tile around the tub/shower. Large laundry room with new LVP flooring, new baseboard heater and new window. Huge deck out back with new floorboards, new top railings and new step/concrete pad down to the yard. Two great sized sheds (One with new doors). New HVAC, new thermostat and new water heater! Both Crawl Spaces have new insulation, new moisture barriers and new entrance doors. Roof was replaced in October of 2019. Chimney was inspected, cleaned and repaired as recommended so it's ready for you to enjoy! New switches, receptacles, smoke detectors, doorknobs and light fixtures throughout the home. Home has been power washed and fresh mulch put down. Agent/Owner

420 E Pall Mall St, Winchester

$335,000

2 Beds ⋅ 2 Baths ⋅ VAWI2010058 MLS ⋅ CLOSED Status

Work where you live. Relax where you work. Welcome to 601 Hollingsworth Drive — a uniquely versatile Winchester home that blends comfortable living with exciting entrepreneurial potential, and ready for its next chapter. Inside, hardwood floors and a classic fireplace set a warm, inviting tone throughout the main level. Currently configured as 2 bedrooms and 1.5 baths, the home was originally built as a 3-bedroom and the wall between the two upper bedrooms was removed to create a generously sized second bedroom — making it easy to convert back to a 3-bedroom layout if your needs require it. It's the kind of flexible floor plan that works for a variety of buyers and lifestyles. The finished basement is where this home truly sets itself apart. Already configured as a fully operational salon space, it's a turnkey solution for a stylist, esthetician, or beauty professional ready to build a clientele right from home. The lower-level patio offers a private outdoor area — a quiet morning retreat away from the main living spaces. But the real magic happens outside. Step onto the covered deck and sink into the hot tub — your personal escape from the everyday, sheltered from the elements and ready to enjoy year-round. The generous yard stretches out beyond, offering space to garden, play, entertain, or simply breathe. Tucked into a quiet, established neighborhood, you're just a short drive from the shops, restaurants, and history of downtown Winchester, the green space of Jim Barnett Park, and convenient access to I-81 and Route 50 for an easy commute in any direction. Offered as-is, this home delivers built-in business infrastructure, flexible living space, multiple outdoor areas, and classic charm — all in one of the Shenandoah Valley's most beloved communities. Whether you're a first-time buyer, entrepreneur, or savvy investor, 601 Hollingsworth Drive is a rare find. Schedule your showing today!

601 Hollingsworth Drive, Winchester

$310,000

3 Beds ⋅ 1 Baths ⋅ VAWI2010016 MLS ⋅ CLOSED Status

Welcome to 423 Shenandoah Place! This charming one-level home offers 3 bedrooms and 1 full bath, combining comfort, convenience, and location all in one. Located on a quiet cul-de-sac in a peaceful neighborhood, you’ll love the sense of privacy while still being close to everything. Step inside to find warm wood floors and a bright, inviting layout that makes everyday living easy. The kitchen features new appliances, including a gas range—perfect for home chefs who appreciate cooking with precision and control. Out back, enjoy a fully fenced yard ideal for pets, play, or entertaining. Relax around the firepit on cool evenings, and take advantage of the storage shed for tools, hobbies, or outdoor gear. And the location? Just approximately 500 feet (as the crow flies) from Jim Barnett Park—offering easy access to walking trails, sports fields, playgrounds, and community events. Whether you're starting out, downsizing, or looking for single-level living in a prime spot, this home checks all the boxes. Schedule your showing today and come see why 423 Shenandoah Place feels like home!

423 Shenandoah Place, Winchester

$285,000

3 Beds ⋅ 1 Baths ⋅ VAWI2009388 MLS ⋅ CLOSED Status

Discover this charming and well maintained home at 1116 Opequon Avenue, offering an excellent opportunity as a starter home or investment property. Located just minutes from Old Town Winchester, this home provides convenience, comfort, and value for under 300K. The main level features hardwood floors throughout the living spaces, three bedrooms, and a full bathroom. The full basement offers great storage, hobby space, or the potential to finish for added living area. Outside, enjoy a spacious yard with a storage shed and off street parking. This home is truly a versatile and affordable option. Schedule your showing and see the potential for yourself.

1116 Opequon Avenue, Winchester

$284,900

2 Beds ⋅ 1 Baths ⋅ VAWI2007956 MLS ⋅ CLOSED Status

Location & Lifestyle Highlights for 516 Hollingsworth Drive, Winchester, VA Nestled in one of Winchester’s most sought-after neighborhoods, 516 Hollingsworth Drive offers more than just a beautiful home; it offers a lifestyle. Enjoy direct access to scenic walking and biking trails, including the popular Green Circle Trail, which winds through town and links several parks and historic districts. Just minutes away, you’ll find Jim Barnett Park, a 170+ acre community destination featuring a recreation center, walking paths, playgrounds, a dog park, picnic shelters, a disc golf course, and an outdoor pool. It’s a perfect space for all ages and activity levels. Residents also love the proximity to Old Town Winchester, a vibrant, walkable historic district known for its charming shops, farm-to-table dining, seasonal festivals, and year-round farmers market. Whether you’re catching a concert at the Bright Box Theater or enjoying an afternoon coffee at a local café, everything is just a short walk or bike ride away. Living in Winchester means being part of a city that blends historic charm with modern convenience, boasting a top-rated public school system, Winchester Medical Center, and easy access to commuter routes including I-81 and Route 7. Whether you're a first-time buyer, looking to downsize, or seeking a well-located investment, this is a fantastic opportunity to enjoy a move-in-ready home in one of Winchester’s most livable areas.

516 Hollingsworth Drive, Winchester

$350,000

3 Beds ⋅ 2 Baths ⋅ VAWI2007704 MLS ⋅ CLOSED Status

This delightful single-level home sits in the heart of vibrant Winchester City. Meticulously updated and maintained, it features an updated kitchen boasting stainless steel appliances (all less than five years old), tasteful subway tile backsplash and classic quartz countertops. Offering three bedrooms, two FULL bathrooms, a living room AND a den, the design and layout can meet all of your housing needs. Other updates include luxury vinyl flooring, newer light fixtures, newer water heater, garage addition, gutter guards in back, and regularly serviced HVAC. Lush lawn surrounds the brick front home with fenced backyard and patio. Schedule a showing today to make this gem your own!

1109 Opequon Avenue, Winchester

$300,000

2 Beds ⋅ 2 Baths ⋅ VAWI2007240 MLS ⋅ CLOSED Status

Come to see this cute cap code the owner took great care, first level has two bedroom and a full bathroom,Living room, dining area and kitchen. The basement has a full bathroom and a family room,Hardwood floor in the main level,huge driveway and a nice backyard.

236 Opequon Avenue, Winchester

$319,000

3 Beds ⋅ 2 Baths ⋅ VAWI2007244 MLS ⋅ CLOSED Status

Welcome home to 556 Eagle Drive! The at home feeling you're going to get when you walk into this house is going to make you never want to leave! On the main floor is a large eat-in kitchen and spacious living room. Conveniently located right down the hall is all three bedrooms and a full bathroom. Moving down stairs in this home you will see your generously sized bonus room! Right off of the bonus room is a half bathroom, laundry room, exterior door, and interior garage access. That's right, no more bringing groceries inside in the rain! Outside the home is a well manicured yard and shed. Location is important when choosing a place to call home and this one has got you covered. You will be located less than a mile from Jim Barnett Park and Shenandoah University. Just a short drive to commuter Routes 522, 81, 50, and 7! Talk about convenience! Just when you think the location couldn't get any better, this home is only a mile away from Old Town Winchester, a walking mall filled with unique locally owned shops and restaurants. This home has been well maintained and loved by its past owners and is ready to be enjoyed by the next. Don’t miss out on making memories in a place you can truly call home!

556 Eagle Drive, Winchester

$348,000

3 Beds ⋅ 2 Baths ⋅ VAWI2007320 MLS ⋅ CLOSED Status

Welcome to this beautifully maintained one-level rambler, where comfort meets modern convenience in the heart of Forest Hills. Step inside to stunning hardwood floors that flow throughout the home, adding warmth and elegance to every space. The spacious living room, complete with a cozy fireplace, creates the perfect setting for relaxation or entertaining. The kitchen is a chef’s delight, featuring stainless steel appliances that complement the home's timeless appeal. Outside, you’ll find a gorgeous Trex deck paired with an additional patio, offering ample space for outdoor dining, entertaining, or simply enjoying peaceful evenings under the stars. Energy efficiency is a key highlight of this home, thanks to its solar panels, providing sustainable and cost-saving benefits. Conveniently located with easy access to Route 81, you’re just minutes from downtown and the Apple Blossom Mall, ensuring shopping, dining, and entertainment are always within reach. Don’t miss the opportunity to own this incredible home in a prime location!

540 Eagle Place, Winchester

$315,000

4 Beds ⋅ 2 Baths ⋅ VAWI2007210 MLS ⋅ CLOSED Status

Welcome home! This charming 4-bedroom, 1.5-bathroom home offers the perfect blend of comfort and convenience, nestled within city limits; perfect for first time home buyers and investors alike! The primary bedroom offers a peaceful retreat, complete with a half bath for added convenience. Three additional bedrooms provide room for everyone. The full bath includes a walk-in shower, making it an ideal space to unwind after a long day. Enjoy the spacious kitchen featuring a large island — perfect for family meals or entertaining. The addition to the home provides even more living space, giving you plenty of room to relax, work, or play. Step outside to your screened-in back porch, where you can enjoy the fresh air while staying protected from the elements. The fully fenced backyard offers a private oasis, perfect for pets, gardening, or just enjoying some outdoor time with family and friends. Plus, location couldn't be better! You'll be within walking distance to Jim Barnett Park, as well as local shops and restaurants. Professional photos coming being of next week. Call today to schedule your private tour!

913 Opequon Avenue, Winchester

$387,000

3 Beds ⋅ 2 Baths ⋅ VAWI2007138 MLS ⋅ CLOSED Status

Welcome to this beautifully renovated 3-bedroom, 2-bathroom home in the heart of Winchester, VA! This charming property offers a fully finished basement with additional living space and a flex/office room, perfect for remote work or extra storage. Every inch of this home has been upgraded with modern touches, including: * Brand-New Roof, Windows, New Hot Water Heater, and HVAC system. * New carpet , refinished Hardwood floors, fresh interior & exterior paint for a stylish, move-in-ready feel. * Fully updated kitchen with new cabinets, quartz countertops, and stainless steel appliances. * New stone paver and railing front stairs, walkway, and refreshed patio, enhancing curb appeal and outdoor enjoyment. Conveniently located near schools, shopping, and commuter routes, this home is a must-see! Don’t miss out—schedule your tour today!

524 Hollingsworth Drive, Winchester

$270,000

3 Beds ⋅ 1 Baths ⋅ VAWI2006982 MLS ⋅ CLOSED Status

Welcome home to 1112 Opequon Avenue, located right in the heart of Winchester. When I say the heart of Winchester, I do mean the heart of Winchester! This beautiful home is located less than half a mile from the incredible Jim Barnett Park. With paved walking trails, disk golf course, volleyball court, playgrounds, sports fields, community pool, 18 station outdoor exercise equipment, pond, pickleball courts, dog park, horseshoe courts, bmx track, and 170+ acres of breathtaking green land only being a short walk away, you will feel like all the park fun and activities are right in your backyard! Only a 5-minute walk away from Shenandoah University and a short drive to commuter Routes 522, 81, 50, and 7! Talk about convenience! Just when you think the location could not get any better, this home is only a mile away from Old Town Winchester, a walking mall filled with unique locally owned shops and restaurants. This brick one level ranch style home has many recently added handicap accessible features making it great for anyone and everyone to enjoy! Walking into this home, you will see a living room waiting for you with a cozy brick fireplace. Past the living room is the dining room and kitchen. Down the hall you will find 3 bedrooms and a recently remodeled bathroom! The only thing left this house needs to make it a home is YOU!

1112 Opequon Avenue, Winchester

$382,000

4 Beds ⋅ 2 Baths ⋅ VAWI2006870 MLS ⋅ CLOSED Status

This beautifully remodeled 4-bedroom, 2-bathroom split-level home is a perfect blend of style and functionality. The main floor features stunning LVP flooring, while the basement offers a mix of cozy carpeting and durable laminate. The updated kitchen boasts granite countertops, stainless steel appliances, and gorgeous cabinetry, with a convenient passthrough to the dining room for easy entertaining. Each bedroom is equipped with ceiling fans for added comfort. The basement includes a laundry area for your convenience. Step outside to enjoy the large multi-level deck, perfect for relaxing or hosting, overlooking a spacious backyard. This home is move-in ready and designed for modern living—don’t miss out!

1016 Opequon Avenue, Winchester

$264,000

3 Beds ⋅ 1 Baths ⋅ VAWI2006858 MLS ⋅ CLOSED Status

Charming and conveniently located, this 3-bedroom, 1-bath home is nestled near downtown Winchester, offering effortless access to Rt. 7, Rt. 50, and I-81 for easy commuting and travel. The property features a spacious, fully fenced backyard, perfect for outdoor activities, complete with a pad ready for a storage building. Additionally, the paved driveway provides convenient off-street parking. This home combines practicality and charm, making it an excellent choice for your next move.

352 Opequon Avenue, Winchester

$305,000

3 Beds ⋅ 2 Baths ⋅ VAWI2006030 MLS ⋅ CLOSED Status

Welcome to your new home! This beautifully updated rancher sits on a spacious, fenced corner lot, perfect for outdoor living and entertaining. With hardwood floors throughout the main living areas and bedrooms, this home exudes warmth and charm. Key Features: Updated Kitchen: Cook with ease in this stylish kitchen, complete with new countertops, sink, LVP flooring, refrigerator, and sleek stainless steel appliances. Stylish Bathrooms: The full bath boasts a walk-in shower, a new vanity, and fresh LVP flooring, while the convenient half bath adds extra functionality. Freshly Painted: The interior and exterior have been newly painted, creating a clean and welcoming atmosphere. Recent Upgrades: Benefit from a new roof on the house and carport (2022) and a new hot water heater (2021), ensuring peace of mind for years to come. Sunroom Oasis: Enjoy your morning coffee or unwind in the evenings in the updated sunroom. Carport & Shed: The carport provides privacy and convenient covered parking, while the shed offers additional storage space. Prime Location: Located in the heart of Winchester, just a short stroll to Old Town, Jim Barnett Park and Shenandoah University. Don’t miss the opportunity to make this lovely rancher your new home! Schedule a showing today!

385 Shenandoah Avenue, Winchester

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