Winchester Homes with Craftsman Style

Winchester Homes with Craftsman Style

Welcome to Winchester, Virginia – a charming city steeped in history and surrounded by breathtaking scenery. Nestled in Frederick County, Winchester offers a perfect blend of small-town charm and urban convenience. With its rich Civil War history, vibrant arts scene, and picturesque landscapes, it's no wonder that residents adore calling this city home.

One of the most appealing aspects of Winchester is its diverse architectural landscape, particularly the enchanting Craftsman-style homes that grace its neighborhoods. Known for their handcrafted details and warm, inviting aesthetics, Craftsman homes embody a sense of comfort and charm that resonates with many homebuyers. Characterized by low-pitched roofs, exposed rafters, and extensive use of natural materials, these homes create a cozy atmosphere that encourages relaxation and connection.

Winchester’s Craftsman-style homes often feature open floor plans, built-in furniture, and beautiful woodwork, making them not only visually appealing but also functional for modern living. As you stroll through the neighborhoods, you'll find these homes nestled among lush gardens and tree-lined streets, creating a serene environment that feels like a retreat from the hustle and bustle of everyday life.

Beyond the homes themselves, Winchester boasts an array of amenities, including delightful local shops, delectable dining options, and a thriving community spirit. With its excellent schools, recreational parks, and cultural events, Winchester is an ideal place for families, young professionals, and retirees alike.

If you're seeking a home that combines historical significance with contemporary charm, look no further than the Craftsman-style houses in Winchester, Virginia. Experience the warmth of this community and the beauty of its architecture – your dream home awaits!

Newest Winchester Homes with Craftsman Style

$399,000
3 Beds ⋅ 1 Baths
Charming 1932 Craftsman Near Downtown Winchester! Step into this classic 1932 Craftsman home, where timeless historic character perfectly meets modern updates. Stunning original craftsman style windows in every room. Boasting an abundance of original woodwork and original wood floors throughout, this home radiates warmth, style, and craftsmanship. The main level highlights Large, open rooms designed for seamless living and entertaining. Bright and open kitchen enjoys newer double ovens, dishwasher, new cooktop and SS hood, new kitchen sink and faucet. The Sunroom features beautiful, heated terracotta tile floors and new double pane windows that flood the space with natural light. Outdoor boasts your classic front porch spanning the width of the house, perfect for relaxing with your favorite beverage. The main floor hosts a 1/2 bath and convenient laundry room. The second level with three generous bedrooms, each equipped with spacious closets, also features a large hall linen closet. The renovated Full Bath comes with custom tile flooring and a sleek, walk-in glass shower. Enjoy the perfect blend of neighborhood charm and urban convenience. If outdoors is your vibe, relaxing on the stone patio with plenty of room for outdoor furniture and a deep yard for kids and pets to enjoy! This home sits just minutes from vibrant downtown restaurants, shopping, and entertainment. Don't miss the opportunity to own a piece of history featuring the perfect balance of original 1930s details and thoughtful modern updates! Call me today to arrange your private showing. PROFESSIONAL PHOTOS COMING SOON.

633 Pennsylvania Ave, Winchester

Listing courtesy of Colony Realty. Contact:

$300,000
3 Beds ⋅ 3 Baths
Charming Country Farmhouse with Modern Updates & Unrestricted Property! Welcome to this charming 1940's farmhouse, thoughtfully renovated and expanded in 2006 to blend timeless character with modern convenience. Offering 3 bedrooms and 3 full bathrooms, this inviting home provides a flexible layout that's perfect for a variety of lifestyles. The main level features a kitchen that flows seamlessly into the living room, creating the perfect gathering space. Two bedrooms and two full bathrooms are conveniently located on the main floor, including a comfortable primary suite complete with a generously sized walk-in closet and private ensuite bath. Upstairs, you'll find a spacious landing area leading to the third bedroom, which boasts its own ensuite full bath and access to a private outdoor deck—an ideal spot to enjoy your morning coffee or unwind at the end of the day. The walk-up attic offers excellent potential to finish and create additional living space, whether you envision a home office, bonus room, or hobby area. Comfort is ensured year-round with a central HVAC system, supplemented by a mini-split system and propane heater for added flexibility. The home also includes both an interior-access cellar and a traditional exterior root cellar, providing abundant storage options. Situated on a quarter-acre lot, the property also features a 24' x 24' detached two-car garage with automatic door openers and 30-amp electrical service, making it ideal for vehicles, a workshop, or recreational equipment. With no restrictions, this property offers many possibilities. Whether you're looking for modern living in a peaceful rural setting, homestead living, or simply room to create your own, this unique property is ready to welcome you home.

2346 Welltown Rd, Winchester

Listing courtesy of Touchstone Realty, LLC. Contact:

$635,690
3 Beds ⋅ 4 Baths
Rare Dual Primary Suites on the Main Level! Backing to trees, this stunning new Matisse at Hiatt Pointe at Snowden Bridge offers the perfect blend of comfort and flexibility for active adults 55+. Personalize your finishes and move in this spring! Enjoy a gourmet kitchen with SS appliances including hood, quartz countertops, an oversized island, and walk-in pantry. The open layout features 10' ceilings, a gas fireplace, and a screened porch overlooking the wooded homesite. The finished lower level adds a rec room, third bedroom, and full bath. Enjoy resort-style amenities including a gated entrance, clubhouse, fitness center, pickleball, bocce, pool, and hot tub. Ask about builder incentives!

3168 Ruby Royce Dr, Winchester

Listing courtesy of Brookfield Mid-Atlantic Brokerage, LLC. Contact: (703) 420-3322
$644,490
6 Beds ⋅ 6 Baths
6-bedroom, 5.5-bath Monroe sits on a desirable cul-de-sac in Snowden Bridge and is still under construction, giving you time to select your own cabinets, countertops, and flooring. The main level features a convenient guest suite. The kitchen boasts Gourmet Stainless Steel Appliances with hood, quartz counters and a farmhouse style sink. Oak stairs lead to the 2nd level. The primary suite has 2 walk in closets, and the ensuite offers dual vanities and shower with frameless door. 3 secondary bedrooms and 2 additional baths are found on the upper level along with the convenient laundry room. Walkout lower level with 9' foundation walls, comes finished with recreation room, bedroom and full bath, making this the perfect place to call home. Snowden Bridge is a premier master-planned community with exceptional amenities including a swimming pool, pirate water park, indoor sportsplex, community park, fenced in dog park, and playground. In addition, there is a bike track, walking trails, and a picnic pavilion. You won’t have to leave to have fun, but when you do you’re just minutes from all the convenience and entertainment around Winchester. Ask about builder incentives! Please note the photos are of a similar home while under construction.

2484 Scotch Bonnet Dr, Winchester

Listing courtesy of Brookfield Mid-Atlantic Brokerage, LLC. Contact: (703) 420-3322
$879,900
5 Beds ⋅ 5 Baths
Immaculate custom home sitting on a half-acre lot in desirable Raven Pointe! Beautiful hardwood floors flow throughout the main level, leading into a dramatic family room with 20-foot ceilings, custom built-ins, a gas fireplace, and high windows featuring remote-controlled custom shades. The gourmet kitchen boasts granite countertops, soft-close cabinets, stainless steel appliances, double wall ovens, a gas cooktop, and opens seamlessly to a second living area with a warm gas fireplace. Main-level primary suite offers tray ceilings, a custom walk-in closets one with a built-in makeup vanity, and a bathroom with dual vanities and a large walk-in shower. Upstairs, you will find two additional spacious bedrooms, a full bath, plus a private in-law suite with its own en-suite bathroom. The bright walk-out lower level features a spacious rec room, full bathroom, bedroom, and a dedicated office space with a window that can also serve as a versatile bonus room. Enjoy outdoor living from the expansive composite deck or relax on the lower covered patio with ceiling fans giving an outdoor living room feel overlooking a private yard supported by an underground irrigation system. Complete with an oversized 3-car garage and located just minutes from I-81, shopping, and downtown Winchester!

243 Summerfield Dr, Winchester

Listing courtesy of Colony Realty. Contact:

$399,990
4 Beds ⋅ 4 Baths
Brand-New 4-Bedroom Townhome | Late Summer Move-In! Enjoy stylish, low-maintenance living in Snowden Bridge's newest section. This thoughtfully designed home features a convenient entry-level bedroom, oak stairs with upgraded railings, and luxury vinyl plank flooring throughout the main level. The bright gourmet kitchen showcases greyhound cabinetry, quartz countertops, and stainless steel appliances, flowing seamlessly into the open living spaces. Upstairs, the spacious primary suite provides a private retreat. Located in a vibrant community with resort-style amenities including a pool, playgrounds, trails, and more to come. Ask about builder incentives! Photos are of a similar home.

132 Swansong Pl, Winchester

Listing courtesy of Brookfield Mid-Atlantic Brokerage, LLC. Contact: (703) 420-3322
$349,990
3 Beds ⋅ 3 Baths
Enjoy low-maintenance living in this beautifully designed two-level villa in Hiatt Pointe! The main-level primary suite features two walk-in closets for exceptional storage, while the gourmet kitchen shines with two-tone white and burlap cabinetry, quartz countertops, and stylish finishes. Upstairs offers two spacious bedrooms, a full bath, and a convenient storage area, providing plenty of room for guests and hobbies. Ideally located near community amenities in Hiatt Pointe, a gated 55+ active adult community, residents enjoy a clubhouse, pool, fitness center, sports courts, and a vibrant lifestyle designed for active living. Ask about builder incentives!

117 Castaway Pl, Winchester

Listing courtesy of Brookfield Mid-Atlantic Brokerage, LLC. Contact: (703) 420-3322
$482,990
2 Beds ⋅ 2 Baths
Under construction for late summer Move-In and Backing to Trees! This beautifully designed home offers easy, open-concept living with a stylish gourmet kitchen featuring quartz countertops, stone gray cabinetry, and stainless steel appliances. The kitchen flows seamlessly into the bright dining and family rooms, while the screened rear porch provides a peaceful retreat overlooking the wooded backdrop. The main-level primary suite includes a spacious walk-in closet and a spa-inspired bath with a seated frameless glass shower. A second bedroom and full bath offer comfort and flexibility for guests. Conveniently located near the two-car garage, the laundry room enhances everyday ease. Located in Hiatt Pointe at Snowden Bridge, a premier 55+ active adult community with exceptional amenities, social opportunities, and a vibrant lifestyle. Ask about builder incentives!

107 Lawford Way, Winchester

Listing courtesy of Brookfield Mid-Atlantic Brokerage, LLC. Contact: (703) 420-3322
$599,990
2 Beds ⋅ 2 Baths
Welcome home to the Avalon, a beautifully designed move-in-ready ranch offering 2 bedrooms, 2 full baths, and up to 2,658 square feet of thoughtfully finished living space. This open-concept floor plan is perfect for effortless everyday living, featuring a spacious great room, a bright, modern kitchen, and a welcoming breakfast area that flows seamlessly into the sunroom. The main level offers a spacious owner's suite, a secondary bedroom, two full baths, and a versatile flex room that's ideal for a home office, den, or hobby space. The finished basement provides abundant additional living space and includes bathroom rough-ins, giving you the opportunity to add another full bath in the future. A two-car garage completes this exceptional home. Located just minutes from historic Downtown Winchester, you'll enjoy easy access to local restaurants, boutiques, entertainment, parks, wineries, and commuter routes while still enjoying the comfort of a peaceful community. Don't miss this opportunity to own a move-in-ready home that combines modern comfort, flexible living spaces, and an unbeatable location. Schedule your private tour today!

159 Williamson, Winchester

Listing courtesy of New Home Star Virginia, LLC. Contact: (703) 967-2073
$715,000
3 Beds ⋅ 4 Baths
Spacious contemporary craftsman style home built in 2007 on .5 acre lot with rare 3 car attached side load garage as well as a detached 2 car & 1 car garages behind the home. This is a car lover's dream with a total 6 garaged parking spaces as well as the driveway or perfect for home based business (with appropriate County approval) - NO HOA!!! Located next to the green space of Kernstown Battlefield. The main level of the home boasts a two story foyer, inviting living room, large dining room and cozy family room with floor to ceiling stone gas fireplace. Kitchen is a chef's dream with oversized island, granite countertops, newer stainless steel appliances and walk-in pantry, upgraded cabinets, hardwood floors and pendant lights! Breakfast room with upgraded lighting - the perfect spot for a morning coffee or tea. There's a mud room as well as two half bathrooms on the main level. On your way up to the bedroom level there is a home office space/den - perfect to work from home, craft or as a swing guest space. The upper level offers a spacious primary bedroom with a double tray ceiling, recessed lights, ceiling fan and walk-in closet. The primary bathroom has a walk-in shower with body spray shower stall, jetted soaking tub & water closet. Two additional spacious secondary bedrooms are served by a hall bathroom with double-sinks and a shower. The home is served by public water and sewer and has a well as a secondary water source to water your gardens and landscaping. Well, garage freezer & satellite dish all convey as-is. Updates included but are not limited to: Water Heater 2024, HVAC approximately 5 years old, newer French door refrigerator and brand new dishwasher, updates to lighting and more! Crawl space was re-insulated in Summer of 2026.

336 Apple Valley Rd, Winchester

Listing courtesy of Century 21 Redwood Realty. Contact:

$959,000
3 Beds ⋅ 3 Baths
Your Dream Home in the Woods – To Be Built on 20 Unrestricted Acres! Create your own family compound, farm, hobbies, your choice. Imagine coming home to this stunning modern farmhouse nestled on twenty wooded and open acres with pleasant peaceful views. This thoughtfully designed home features spacious living areas, modern finishes, exterior that blends beautifully with its natural surroundings. Perfect for those seeking privacy, peace, and the beauty of nature, yet with convenient access to nearby amenities. Plenty of room for outdoor recreation, gardening, or simply enjoying the view from your porch. Build your dream lifestyle here – endless possibilities on unrestricted land! Escape to a serene retreat of rolling meadows, shady woodlands, and sparkling little ponds. Here, the land is alive—deer wander gracefully through the trees, wild turkeys stride across the fields, and songbirds fill the air with music. Bring your horses, cows, goats, or sheep to graze the open pastures, or simply enjoy the peace of living alongside nature. This is more than just land—it’s a private sanctuary where farm life, wildlife, and natural beauty come together in perfect harmony.” In the summer, kids might toss in a line, pulling out a perch or even a fat catfish. Families might watch dragonflies skimming the water’s edge. At night, fireflies light up the grasses around the pond, adding to the magic. Builder is also willing to build your plans. Price is projected and subject to change.

Light Rd, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact: (540) 665-0360
$959,000
3 Beds ⋅ 3 Baths
Your Dream Home in the Woods – To Be Built on 20 Unrestricted Acres! Create your own family compound, farm, hobbies, your choice. Imagine coming home to this stunning modern farmhouse nestled on twenty wooded and open acres with pleasant peaceful views. This thoughtfully designed home features spacious living areas, modern finishes, exterior that blends beautifully with its natural surroundings. Perfect for those seeking privacy, peace, and the beauty of nature, yet with convenient access to nearby amenities. Plenty of room for outdoor recreation, gardening, or simply enjoying the view from your porch. Build your dream lifestyle here – endless possibilities on unrestricted land! Escape to a serene retreat of rolling meadows, shady woodlands, and sparkling little ponds. Here, the land is alive—deer wander gracefully through the trees, wild turkeys stride across the fields, and songbirds fill the air with music. Bring your horses, cows, goats, or sheep to graze the open pastures, or simply enjoy the peace of living alongside nature. This is more than just land—it’s a private sanctuary where farm life, wildlife, and natural beauty come together in perfect harmony.” In the summer, kids might toss in a line, pulling out a perch or even a fat catfish. Families might watch dragonflies skimming the water’s edge. At night, fireflies light up the grasses around the pond, adding to the magic. Builder is also willing to build your plans. Price is projected and subject to change.

Light Rd, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact: (540) 665-0360
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