Winchester Homes with Cape Cod Style

Winchester Homes with Cape Cod Style

Welcome to Winchester, Virginia, a charming city steeped in history and surrounded by the breathtaking beauty of the Shenandoah Valley. With its picturesque streets, vibrant community, and rich cultural heritage, Winchester is a hidden gem that offers the perfect blend of small-town charm and modern conveniences. Nestled between the Blue Ridge Mountains and the Allegheny Highlands, this city boasts stunning landscapes, making it an ideal location for those who appreciate nature and outdoor activities.

Winchester is renowned for its historic downtown, where visitors can explore a variety of boutique shops, delightful eateries, and captivating museums. The city is also home to several annual festivals and events that celebrate its unique culture, ensuring there’s always something happening in this lively community. Families will appreciate the excellent schools and friendly neighborhoods, making it a fantastic place to call home.

Among the many architectural styles that grace the streets of Winchester, Cape Cod homes stand out for their timeless appeal and cozy charm. Characterized by steeply pitched roofs, dormer windows, and symmetrical facades, these homes exude a sense of warmth and comfort. Perfect for families or those looking for a serene retreat, Cape Cod-style houses often feature inviting front porches and spacious yards, ideal for enjoying the picturesque Virginia seasons.

Whether you’re a first-time homebuyer or seeking a tranquil place to retire, Winchester offers a diverse selection of Cape Cod homes that capture the essence of classic American architecture. Embrace the charm of this historic city and discover your dream home in Winchester today!

Newest Winchester Homes with Cape Cod Style

$280,000
3 Beds ⋅ 1 Baths
Recently renovated and move-in ready! This updated 3-bedroom, 1-bath home offers the perfect combination of modern finishes and worry-free living with major upgrades already completed. Enjoy peace of mind with a new roof, new windows, new siding, and a brand-new HVAC system, providing comfort and energy efficiency for years to come. Inside, you'll find stylish luxury vinyl plank (LVP) flooring throughout, creating a seamless and low-maintenance living space. The updated kitchen features all-new stainless steel appliances, offering both functionality and a sleek, contemporary look that's ready for everyday living or entertaining. Conveniently located on N. Frederick Pike with easy access to shopping, dining, schools, and commuter routes, this home is an excellent opportunity for first-time buyers, those looking to downsize, or anyone seeking a turnkey property. Don't miss your chance to own this beautifully renovated home, schedule your private showing today!

2810 N Frederick Pike, Winchester

Listing courtesy of Weichert Realtors - Blue Ribbon. Contact: 3042628700
$180,000
3 Beds ⋅ 1 Baths
Opportunity awaits at 309 Liberty Avenue in Winchester City. This classic Cape Cod offers the chance to create something truly special in an area experiencing continued growth, infrastructure improvements, and neighborhood investment. The property does require substantial work, making cash financing the most likely option; however, the potential is significant for a buyer with the vision to transform it into a distinctive home while building meaningful sweat equity. The level backyard provides plenty of usable outdoor space, and the rear alley creates the possibility of adding a gated entrance for convenient off-street parking behind the home. A rare opportunity to reimagine a well-located Winchester property and make it entirely your own.

309 Liberty Ave, Winchester

Listing courtesy of Keller Williams Realty. Contact: 7036690099
$420,000
4 Beds ⋅ 3 Baths
Welcome to 101 Charlton Road, a charming 4-bedroom, 2.5-bath Cape Cod situated on a desirable corner lot. This well-maintained home features a main-level primary suite and beautiful hardwood floors throughout the main living areas. The spacious kitchen is equipped with stainless steel appliances, a center island, breakfast nook, and flows seamlessly into the separate dining room and inviting living room, perfect for everyday living and entertaining. Upstairs, you'll find three additional bedrooms, 1.5 baths, and the convenience of an upper-level laundry room. Enjoy outdoor living in the fenced backyard complete with a storage shed, rear deck, and plenty of space for pets, gardening, or gatherings. Relax on the welcoming covered front porch and enjoy the convenience of being just minutes from Historic Old Town Winchester, Shenandoah University, Winchester Medical Center, shopping, dining, local wineries, parks, and easy access to Routes 7, 50, and I-81 for commuting. All sizes are approximate.

101 Charlton Rd, Winchester

Listing courtesy of RE/MAX Roots. Contact: (540) 686-7362
$425,000
5 Beds ⋅ 2 Baths
Welcome to 206 Dogwood Rd. Well maintained 5 Bedroom 2 Bath Cape Cod in a quiet neighborhood conveniently located a short distance from the downtown area. HVAC has just been installed..The house is on your own septic system. Sunroom with a laundry was added in 2007. An additional lot is included with this house.....Lot number #55-B-3-2-63 Lot 63 making the total area 1 acre. The Basement has some framing started to add extra living space with a wood stove already installed.

206 Dogwood Rd, Winchester

Listing courtesy of Wildhawks Realty LLC. Contact: (540) 662-0211
$363,900
4 Beds ⋅ 3 Baths
Enchanting Cape Cod in an ideal in‑town location, this home has a welcoming ease to it, offering 3–4 bedrooms and 2.5 bathrooms with a layout that adapts beautifully to everyday living. The main level includes two convenient bedrooms, a comfortable, light‑filled living room, a separate dining area, and a renovated kitchen featuring new cabinets and stainless‑steel appliances. In 2021, the home received a thoughtful refresh: new vinyl plank flooring throughout, renovated bathrooms, new light fixtures, new receptacles/switches/covers, a new roof, and more—paired with updated plumbing for added peace of mind. Upstairs, you’ll find two additional rooms and a bathroom, including a potential fourth bedroom or bonus room ideal for an office or extra space. With over 2,000 sq ft of finished living space, the home also includes a finished basement with a full bath and a door leading directly to the backyard, offering room to expand, unwind, or create a second living area. Outside you will find a spacious deck and fully fenced backyard with privacy fencing creating a comfortable outdoor retreat—perfect for relaxed evenings, weekend grilling, and easy gatherings. All of this in a downtown Winchester location, close to shopping, restaurants, and everyday conveniences. For anyone searching for a place that simply feels right the moment you arrive—a reminder that home isn’t just a place, it’s a feeling—this enchanting Cape Cod captures it. Schedule your tour today!

621 Patterson Ave, Winchester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (540) 662-3484
$359,900
3 Beds ⋅ 2 Baths
Welcome to Gray Avenue! This beautifully updated 3-bedroom, 2-bath home offers over 1,700 square feet of stylish living space, blending timeless charm with modern finishes throughout. Rich hardwood floors flow throughout the home, creating warmth and character from the moment you step inside. The sun-filled living room feels bright and inviting, highlighted by a custom light fixture and a seamless connection to the formal dining area—perfect for hosting friends and family. The kitchen is a standout feature, boasting granite countertops, stainless steel appliances, white cabinetry, and designer-inspired finishes that make both cooking and entertaining a pleasure. Each bedroom is generously sized with ample closet space, while the thoughtful layout provides comfort and functionality throughout. Outside, a private cement parking pad adds everyday convenience. Packed with charm, natural light, and updates you'll love, Gray Avenue is the perfect place to call home.

601 Gray Ave, Winchester

Listing courtesy of Samson Properties. Contact: 7033788810
$300,000
3 Beds ⋅ 2 Baths
Charming Cape Cod-style home located at 126 Marple Rd in the desirable north end of Winchester! This well-maintained 3-bedroom, 1.5-bath home offers timeless character, functional living space, and a convenient commuter-friendly location. The main level features a bedroom with a 1/2 bath, a living room, a dining room, and a kitchen. Upstairs, you’ll find additional bedrooms with a shared bathroom. Enjoy relaxing mornings on the covered front porch. The large yard is perfect for gardening, outdoor entertaining, or recreation. Additional highlights include a full unfinished basement offering excellent storage, a detached shed for tools and equipment, a newer roof installed in 2023, and a well replaced in 2014 for added peace of mind. Well, septic, and WDI inspections have been completed. *Conveniently located near Winchester Medical Center, shopping, dining, schools, and everyday amenities. This home also offers easy access to Route 522, Rt 37, I-81, and Route 11, making commuting to surrounding areas, including Martinsburg and Northern Virginia, simple and convenient. Enjoy nearby attractions such as historic Old Town Winchester, local parks, wineries, and the scenic Shenandoah Valley. All sizes are approximate. Well, septic, and WDI inspections have been completed.

126 Marple Rd, Winchester

Listing courtesy of RE/MAX Roots. Contact: (540) 686-7362
$760,000
5 Beds ⋅ 5 Baths
Welcome to 769 Seldon Drive—an elegant brick-front colonial situated on nearly half an acre in one of Winchester’s most desirable neighborhoods. Offering over 4,500 finished square feet, this spacious 5-bedroom, 4.5-bath home is designed for comfort, flexibility, and multi-generational living. The main level features a generously sized primary suite with a walk-in closet and en-suite bath, along with formal living and dining rooms, a warm and inviting family room with fireplace, and a well-equipped kitchen with center island and breakfast area. Hardwood floors and detailed trim work add classic character throughout. A standout feature of this home is the private ground-level apartment with its own entrance—complete with a full kitchen, bedroom, bathroom, living space, and dedicated laundry. Perfect for guests, extended family, or potential rental income. Upstairs, you'll find additional spacious bedrooms and full baths, offering plenty of room for everyone. Enjoy the outdoors from your beautifully landscaped yard with space to garden, entertain, or relax. A two-car garage and extended driveway provide ample parking. Conveniently located just minutes to downtown Winchester, parks, shopping, dining, and commuter routes—this home offers the space and versatility you've been searching for. Schedule your private showing today!

769 Seldon Dr, Winchester

Listing courtesy of Keller Williams Realty. Contact: 7036690099
$575,000
6 Beds ⋅ 4 Baths
Versatile on Valley! So many possibilities! This versatile duplex is full of charm and opportunity! The original 1936 home features beautiful original hardwood floors, tall ceilings, fireplace, 4 season sunroom, and a stunning staircase that adds timeless character. The front unit is perfect for an owner-occupant who wants to enjoy historic charm while generating income from the back unit, or you can rent out both units for a strong investment. The rear unit is already leased to a reliable tenant, providing immediate cash flow. The entire home can easily be converted back to one large living space with the removal of drywall over two doorways. The new roof and gutters were installed in 2024 and both full bathrooms have been updated to include walk-in tiled showers. The heating fuel was converted to natural gas and new boilers were installed in 2011. Each unit has separate utilities except for water and sewer. With its unique character, flexible layout, and proven rental history, this property offers endless possibilities for living, investing, or both!

1400 Valley Ave, Winchester

Listing courtesy of Samson Properties. Contact: (540) 348-4911
$575,000
Versatile on Valley! So many possibilities! This versatile duplex is full of charm and opportunity! The original 1936 home features beautiful wood floors, tall ceilings, fireplace, sunroom, and a stunning staircase that adds timeless character. Each Unit has 3 bedrooms and 1.5 baths. The front unit is perfect for an owner-occupant who wants to enjoy historic charm while generating income from the back unit, or you can rent out both units for a strong investment. The rear unit is already leased to a reliable tenant, providing immediate cash flow. The new roof and gutters were installed just last year and both full bathrooms have been updated to include walk-in tiled showers. The heating fuel was converted to natural gas and new boilers were installed in 2011. Each unit has separate utilities except for water and sewer. With its unique character, flexible layout, and proven rental history, this property offers endless possibilities for living, investing, or both!

1400 Valley Ave, Winchester

Listing courtesy of Samson Properties. Contact: (540) 348-4911
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