Welcome home to this beautifully updated, move-in ready 4-bedroom, 2.5-bathroom Home offering 2,080 square feet of thoughtfully designed living space. Boasting exceptional curb appeal, the property features a brand-new roof, new HVAC system, fresh interior paint, and plush new carpeting throughout. Designed for modern living, the main level welcomes you with a formal dining room and a versatile office/den, perfect for remote work or a quiet reading space. The heart of the home is the eat-in kitchen, which flows into a spacious Family room centered around a cozy wood-burning fireplace. From the living room, step outside onto the back deck to enjoy a private backyard, ideal for entertaining or relaxing. The highly desirable first-floor primary suite provides a peaceful retreat with convenience in mind. Upstairs, you will find three additional bedrooms and an expansive, walk-in attic that offers incredible storage capacity or potential for future expansion. Perfectly situated in a prime location, this home offers quick access to Route 199, local shopping, dining, and the historic charm of Colonial Williamsburg.
Active
$479,000
5540 Rolling Woods Dr, Williamsburg, VA 23185
4beds
2,080sqft
Single Family Residence
Built in 1988
0.28 Acres Lot
$474,700 Zestimate®
$230/sqft
$10/mo HOA
What's special
Cozy wood-burning fireplacePlush new carpeting throughoutExceptional curb appealPrivate backyardFresh interior paintBrand-new roofBeautifully updated
- 37 days |
- 958 |
- 44 |
Likely to sell faster than
Zillow last checked:
Listing updated:
Listed by:
Mike Stevens 757-812-4794,
The Steele Group Sotheby's Int 757-378-9090
Source: WMLS,MLS#: 2602371
Originating MLS: Williamsburg MLS
Originating MLS: Williamsburg MLSFacts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 3
- Full bathrooms: 2
- 1/2 bathrooms: 1
Primary bedroom
- Description: First Floor Primary
- Level: First
Bedroom 2
- Level: Second
Bedroom 3
- Level: Second
Bedroom 4
- Level: Second
Additional room
- Description: Huge Walkin Attic
- Level: Second
Dining room
- Level: First
Family room
- Description: Off the Kitchen w/access to the Deck
- Level: First
Kitchen
- Description: Eat In Kitchen with plenty of Space
- Level: First
Laundry
- Level: First
Living room
- Description: Use as an Office or Living Room or Dining Room
- Level: First
Heating
- Forced Air, Natural Gas
Cooling
- Central Air
Appliances
- Included: Built-In Oven, Dryer, Dishwasher, Electric Cooking, Electric Water Heater, Disposal, Microwave, Range, Refrigerator, Washer
- Laundry: Washer Hookup, Dryer Hookup
Features
- Attic, Bay Window, Ceiling Fan(s), Dining Area, Eat-in Kitchen, High Ceilings, Pantry, Walk-In Closet(s)
- Flooring: Carpet, Linoleum, Wood
- Basement: Crawl Space
- Number of fireplaces: 1
Interior area
- Total interior livable area: 2,080 sqft
Property
Parking
- Total spaces: 2
- Parking features: Attached, Direct Access, Driveway, Garage, Garage Door Opener, Paved
- Attached garage spaces: 2
Features
- Levels: Two
- Stories: 2
- Patio & porch: Deck, Porch
- Exterior features: Deck, Porch, Paved Driveway
- Pool features: None
- Fencing: Privacy
Lot
- Size: 0.28 Acres
Details
- Parcel number: 4811300047
- Zoning description: R2
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Two Story
- Property subtype: Single Family Residence
Materials
- Drywall, Frame, Vinyl Siding
- Roof: Asphalt,Shingle
Condition
- New construction: No
- Year built: 1988
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Community & HOA
Community
- Features: Playground, Park
- Subdivision: Rolling Woods
HOA
- Has HOA: No
- Services included: Common Areas
- HOA fee: $10 monthly
- HOA name: Rolling Woods Poa
- HOA phone: 757-258-2429
Location
- Region: Williamsburg
Financial & listing details
- Price per square foot: $230/sqft
- Tax assessed value: $345,000
- Annual tax amount: $2,864
- Date on market: 7/18/2026
- Ownership: Fee Simple,Individuals
Estimated market value
$474,700
$451,000 - $498,000
$2,951/mo
Price history
| Date | Event | Price |
|---|---|---|
| 7/18/2026 | Listed for sale | $479,000+185.1%$230/sqft |
Source:  WMLS #2602371 Report a problem | ||
| 9/28/1992 | Sold | $168,000$81/sqft |
Source: Agent Provided Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $2,864 | $345,000 |
| 2024 | $2,864 +13.9% | $345,000 +13.9% |
| 2023 | $2,513 | $302,800 |
| 2022 | $2,513 +12.9% | $302,800 +14.3% |
| 2021 | $2,226 | $265,000 |
| 2020 | $2,226 +6.5% | $265,000 +6.5% |
| 2019 | $2,090 +3.7% | $248,800 +3.7% |
| 2017 | $2,015 +102% | $239,900 |
| 2016 | $998 | $239,900 +1% |
| 2015 | $998 | $237,500 |
| 2014 | -- | $237,500 +2% |
| 2013 | -- | $232,800 |
| 2012 | -- | $232,800 -11.2% |
| 2011 | -- | $262,300 |
| 2010 | -- | $262,300 |
| 2009 | -- | $262,300 |
| 2008 | -- | -- |
| 2007 | -- | -- |
| 2005 | -- | -- |
| 2004 | -- | -- |
| 2003 | -- | -- |
| 2002 | -- | -- |
| 2001 | -- | -- |
Find assessor info on the county website
Monthly payment
Est. payment
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.Climate risks
Neighborhood: 23185
Nearby schools
GreatSchools rating
- 8/10Laurel Lane Elementary SchoolGrades: PK-5Distance: 0.4 mi
- 7/10Berkeley Middle SchoolGrades: 6-8Distance: 2.2 mi
- 5/10Lafayette High SchoolGrades: 9-12Distance: 5.5 mi
Schools provided by the listing agent
- Elementary: Laurel Lane
- Middle: Berkeley
- High: Lafayette
Source: WMLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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A local agent can set up tours, give advice and negotiate with sellers.
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