City of Williamsburg Homes with Wooded Exterior features

Welcome to the charming City of Williamsburg, Virginia—a place where history meets modern living in a picturesque setting. Nestled in the heart of Virginia’s Historic Triangle, Williamsburg is renowned for its rich colonial heritage, vibrant community, and stunning natural landscapes. With its cobblestone streets and beautifully preserved buildings, the city offers a unique blend of past and present, making it an enchanting destination for residents and visitors alike.

One of the most appealing aspects of Williamsburg is its diverse array of homes, particularly those featuring charming wooded exteriors. Imagine waking up to the soothing sounds of nature, surrounded by towering trees and lush greenery. Homes with wooded exterior features not only provide a serene and tranquil atmosphere but also offer a sense of privacy and seclusion that is hard to find in more urban settings. These properties often boast stunning architecture that harmonizes with the natural landscape, creating a seamless blend of indoor and outdoor living.

Whether you’re looking for a cozy cottage or a spacious family home, Williamsburg has something to suit every taste and lifestyle. The city's commitment to preserving its natural beauty ensures that residents can enjoy scenic views and outdoor activities year-round, from hiking and biking to leisurely strolls through historic parks.

Discover the magic of Williamsburg, where the charm of history meets the beauty of nature, and find your dream home nestled among the trees. Embrace a lifestyle that celebrates both community and tranquility in this vibrant Virginia city!

Newest City of Williamsburg Homes with Wooded Exterior features

$975,000

4 Beds ⋅ 3.2 Baths ⋅ 10653503 MLS

Stunning all-brick home located close to Colonial Williamsburg and W&M. Newly renovated, professionally landscaped private lot bordering permanent greenspace! Matching hardwood floors throughout. Spacious 1st floor primary BR with luxury bathroom & walk-in closet. Custom kitchen w/granite counters, upgraded cabinets, SubZero refrig, Wolf gas cooktop, Advantium oven, warming drawer. Open vaulted ceiling great room w/brick-faced gas fireplace, opens to the sun-filled dining area, kitchen and adjacent 1700-bottle wine room. Living rm has built-in bookcases. Second floor features 3 additional bedrooms with hardwood floors, 1 & 1/2 baths, large closets & walk-in storage. A separate stairscase leads to a multi-purpose bonus room with built-in bookcases, additional walk-in storage & attached full bath. The private backyard features a brick patio with a built-in Lion grill and a storage shed w/electricit. Additional upgrades include landscaping lighting, Smart house features, security sys, water filter sys, built-in speakers, newer roof and encapsulated crawl space.

320 Yorkshire Dr Drive, City of Williamsburg

$375,000

3 Beds ⋅ 2 Baths ⋅ 10652611 MLS

This completely updated home is just a few blocks to downtown! This 3-bedroom, 2-bath home is move-in ready. Complete with NEW roof, NEW windows, NEW appliances and LVP flooring. Outside, the large lot opens to a fully fenced backyard with a HUGE detached garage that offers flexible space for vehicles, storage, a workshop or hobbies. Best of all, there are NO HOA fees but still enjoy the park nearby equipped with a brand-new playground. Less than 5-minutes to downtown and just a 2-minute drive to Colonial Williamsburg, shopping and dining. Whether you're looking for a primary residence, convenient William & Mary housing or a long-term rental investment, this home offers location, updates and flexibility—plus quick access to I-64 for commuting throughout Hampton Roads and toward Richmond.

512 Dunning Street, City of Williamsburg

$385,000

3 Beds ⋅ 2.1 Baths ⋅ 10652348 MLS

Beautifully maintained brick townhome located in the highly desirable Wyndham Plantation community. Offering 3 bedrooms, 2.5 baths, a spacious loft, and a private wooded setting, this move-in-ready home blends comfort and convenience. The first-floor primary suite provides everyday ease and privacy, while two additional bedrooms and a large loft upstairs offer flexible space for guests, a home office, or a media area. The bright, open layout is complemented by a spacious garage, a brand-new HVAC system, and a new refrigerator. Enjoy peaceful views of the woods from the private deck, all within the City of Williamsburg. Conveniently situated near the College of William & Mary, Historic Area, shopping, dining, and local attractions, this inviting home is ready for its next owner.

236 Zelkova Road, City of Williamsburg

$195,000

3 Beds ⋅ 1 Baths ⋅ 10651384 MLS

Investor special on Penniman Road in Williamsburg! This property offers an excellent opportunity for an investor, contractor, or buyer looking for a renovation project with strong potential. Bring your vision and transform this home into a profitable resale, rental property, or personalized residence. Conveniently located near shopping, dining, major roadways, and Williamsburg-area attractions. Property is being sold as-is, and the seller will make no repairs. Don’t miss the opportunity to add value in a desirable and established location!

1749 Penniman Road, City of Williamsburg

$1,200,000

4 Beds ⋅ 4.1 Baths ⋅ 10651346 MLS

Lots have been cleared — Rare Opportunity! Don’t miss this exceptional chance to own a brand-new 4 bedroom, 4.5 bath home in the heart of historic downtown Williamsburg. New construction in this coveted area is nearly unheard of, offering the perfect blend of modern luxury and classic charm just minutes from Colonial Williamsburg, shops, dining, and world-class attractions. This planned custom brick home features an open-concept layout, high-end finishes, gourmet kitchen, spacious primary suites, and energy-efficient design. Enjoy living in one of Virginia’s most iconic settings, with the opportunity to personalize finishes and selections. A truly rare offering for those seeking convenience, history, and luxury in one. Contact us today to explore plans and secure this premier downtown address.

317 Indian Springs Road, City of Williamsburg

$679,999

4 Beds ⋅ 3.1 Baths ⋅ 10650831 MLS

Beautifully maintained 4-bedroom home nestled in a private, wooded setting with seasonal water views of College Creek. This inviting home features gleaming hardwood floors, a convenient first-floor primary suite, and a spacious screened porch—perfect for relaxing and enjoying the peaceful surroundings. Additional highlights include a whole-house generator, newer roof (2017), and newer downstairs HVAC (2026). The home has been thoughtfully cared for and offers comfortable living with plenty of space to entertain or unwind. Located in Port Anne, a desirable community within the City of Williamsburg, residents enjoy access to a community pool and a convenient location close to everything Historic Williamsburg has to offer. Enjoy easy access to Grand Illumination, local farmers markets, and festivities along Duke of Gloucester Street, along with the area's many dining, shopping, and cultural attractions. A wonderful opportunity to enjoy privacy, comfort, and the best of Williamsburg living!

16 The Palisades, City of Williamsburg

$765,000

4 Beds ⋅ 3.1 Baths ⋅ 10647653 MLS

Quintessential Colonial in a sought-after City of Williamsburg location! Set on a quiet cul-de-sac and backing to wooded privacy, this all-brick residence offers 3,473 square feet with four bedrooms, three-and-a-half baths, a bonus room and sunroom. The welcoming foyer features a Chippendale-style staircase, while the expansive living room showcases millwork, dentil molding and timeless architectural detail. The renovated kitchen offers a center island, granite countertops, pine flooring and a sun-filled breakfast area. French doors open to the sunroom, extending the kitchen and living spaces. Upstairs, the primary suite includes a large walk-in closet, accompanied by three additional spacious bedrooms. Accessed by a back staircase, the bonus room features built-in bookcases, a built-in desk, skylights, an en-suite bath and cedar closet. Additional highlights include an oversized garage with EV charger, a roof replaced approximately 10 years ago and a 500-square-foot walk-up attic.

127 Woodmere Court, City of Williamsburg

$975,000

5 Beds ⋅ 3.2 Baths ⋅ 10647645 MLS

Located in Port Anne, one of downtown Williamsburg's most desirable communities, this home, designed by R. Spencer and built by Pultz Builders, offers over 4,100 square feet across three finished levels with 5 bedrooms, 3 full baths, and 2 half baths. A dramatic two-story great room, expansive windows, and soaring ceilings fill the home with natural light while framing the wooded setting with views toward College Creek. The main level features a first-floor primary suite, formal dining room, spacious family room with fireplace, and an eat-in kitchen with granite countertops, double ovens, and a breakfast area. Upstairs you'll find two bedrooms, a full bath, and a loft overlooking the main living area. The finished walk-out basement offers exceptional flexibility with a spacious recreation room, office or potential sixth bedroom, two additional bedrooms, a full and half bath, and a two-sided fireplace. The screened porch and patio provide a private setting for relaxing or entertaining. Additional features include a whole-house generator, zoned heating and cooling, and abundant storage. Port Anne residents enjoy a clubhouse, pool, tennis courts, exercise room, and beautifully maintained common areas, all just moments from Colonial Williamsburg, William & Mary, restaurants, shopping, and the conveniences of downtown Williamsburg.

8 The Palisades, City of Williamsburg

$650,000

5 Beds ⋅ 3.1 Baths ⋅ 10646079 MLS

Welcome to 105 Meredith Way in Williamsburg, Virginia, a beautiful brick-front home offering timeless curb appeal, spacious interiors, and a setting that feels both elegant and inviting. Beautifully manicured landscaping with an 8-zone sprinkler system provides stunning curb appeal. The home offers hardwood floors, crown molding, wainscoting, and thoughtful architectural details throughout. The formal dining is exceptional for formal gatherings with adjustable lighting and a butler’s pantry. Opposite the formal dining is a large office with built-in shelving and oversized windows for plenty of natural light. The open living area features a dual-sided fireplace with an upgraded enclosed sitting room, perfect for a playroom or workout room. The kitchen contains granite countertops, new stainless steel appliances (never used cooktop), oversized cabinetry, recessed lighting, a center island, and a casual dining area. A spacious first-floor primary suite provides a relaxing retreat with a tray ceiling and bay windows, and a master bath with a jetted tub, double vanity sinks, and a huge walk-in closet. Upstairs, the large loft serves as a second living area and a billiards room with a wet bar. A second primary suite offers a large walk-in closet and plenty of room for the in-laws. Three additional bedrooms and a full bath provide more than enough space for a large family. Outside, enjoy the benefits of being the first home in the HOA with a huge, wooded side yard and a peaceful backyard. This home has many desirable upgrades, including a tankless water heater, water softener, dual HVAC systems (downstairs system is less than a month old), conveying pool & ping pong tables, conveying refrigerator/freezers, and a whole-home Generac backup generator. Conveniently located in a highly desirable area and less than 10 minutes from Colonial Williamsburg, William and Mary, and plenty of shopping and dining. Schedule your private showing today and see all that 105 Meredith Way has to offer!

105 Meredith Way, City of Williamsburg

$215,000

2 Beds ⋅ 2 Baths ⋅ 10637246 MLS

Welcome to Barclay Square! Where comfort, convenience, and natural light come together in this beautifully maintained 2 bedroom, 2 bathroom condo. Featuring an open concept living room floor plan, this home offers a spacious and inviting atmosphere that will be great for entertaining. The bright sunroom, lined with ample windows, fills the space with natural light and creates a cozy spot for morning coffee, reading, or a home office. Both bedrooms are generously sized, providing comfort and privacy, while the two full bathrooms offer functionality and convenience for residents and guests alike. Located in the desirable Barclay Square community, this condo combines low-maintenance living with a welcoming neighborhood atmosphere within close proximity to shopping, dining, and everyday conveniences. Whether you're a first-time buyer, downsizing, or looking for an investment opportunity, this charming home is ready to impress!

376 Merrimac Trail Unit 622, City of Williamsburg

$999,000

4 Beds ⋅ 3.1 Baths ⋅ 10633065 MLS

A phenomenal first offering in the coveted Port Anne: A custom, all-brick waterfront residence overlooking College Creek with sweeping creek views and timeless Williamsburg charm situated in an Audubon Habitat Sanctuary. With Architecture by Roger Guernsey himself with interiors by Gary Dennis Fine and built by Rob Collins, this approx. 3,000 sq. ft. home showcases vaulted ceilings, graceful archways, rich trim work, and a fantastic entertaining floor plan with true first-level living. The main level features a large primary suite opening to the screened porch, an office with private terrace, and a graceful kitchen with gorgeous glass cabinet details. Upstairs, three bedrooms each enjoy stunning views. A gardener’s delight with potting shed off the garage. Adjacent to Colonial Williamsburg, downtown dining, shopping, and College Landing Park. Elevator chute ready to connect all three levels. New roof (2025), newer HVAC(2023), and new hot water heater (2024) complete this rare offering.

20 The Palisades, City of Williamsburg

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