This property is no longer actively marketed. The last publicly available listing details are shown below; contact us for current availability.
About this home
One buyer's loss is another buyer's opportunity!Timeless elegance meets modern luxury in this exceptional custom Colonial, privately set on 3.5 meticulously landscaped acres. Offering 4 spacious bedrooms and a beautifully appointed walk-out lower-level in-law suite, this remarkable home blends sophistication, comfort, and versatility. A grand two-story foyer welcomes you into a home showcasing impeccable craftsmanship, classic architecture, and custom millwork throughout. The thoughtfully designed floor plan features a private home office, elegant formal dining room, and an inviting family room centered around a stunning fireplace. The expansive chef's kitchen flows seamlessly into the main living areas, creating the ideal space for everyday living and entertaining.Equipped with a custom cabinet-front refrigerator, plus an additional stainless steel refrigerator offering expanded refrigerated storage. Just beyond, a sun-filled four-season room overlooks the private backyard and opens to the expansive composite deck. Privately situated at the opposite end of the home, the first-floor media room features custom millwork, a built-in bar, and the perfect setting for entertaining. Designed with both luxury and practicality in mind, the home offers central air conditioning throughout, while strategically placed mini-split systems provide individualized comfort and energy-efficient climate control in frequently occupied spaces. The luxurious primary suite features a spa-inspired bath, while the additional bedrooms are generously sized. The walk-out lower level offers a complete in-law suite with its own living space, ideal for multigenerational living, guests, or an au pair. Outside, the expansive composite deck overlooks a gunite inground pool surrounded by professional landscaping, creating exceptional privacy. A classic farmer's porch completes this extraordinary property, where timeless architecture, refined finishes, and effortless indoor-outdoor living come together.
Listing last checked: Listing updated:
Listed by Shannon DiPietro · DiPietro Group Real Estate · MLS #5099575
Request property information
Select a document to start a request. You can add others in the form. Availability varies.
Details at a glance
Interior5 property facts
- Rooms
- 10
- Heating
- Wood, Propane, Oil, Solar, Electric, Forced Air, Wood Stove
- Cooling
- Central Air
- Flooring
- Carpet, Ceramic Tile, Hardwood, Laminate, Bamboo
- Basement
- Yes · Finished, Insulated, Interior Stairs, Walkout, Interior Access, Exterior Access
Building5 property facts
- Style
- Single Family Residence
- Year built
- 1999
- Garage
- 3
- Parking
- 3
- Roof
- Shingle
Land & utilities5 property facts
- Lot size
- 3.79 acres
- Water
- Well, Private
- Sewer
- Septic Tank
- Pool
- Yes · In-Ground Pool
- Zoning
- RD
Financial2 property facts
- Annual taxes
- $20,220
- Assessment year
- 2025
Location
Explore the area
Get to know the neighborhood and explore local school information as you picture life here.
Price and status timeline
- Sld
$799,900 · Sold $774,800 · Jul 11, 2016
More property insights
Photo-based condition insights
Overall presentation: above average
Explore more of Windham
Continue your search in Windham.
Need help making sense of this home?
About 5 Sherwood Road
Is this home available for a showing?
This home is no longer actively marketed. Ask our team about its current status or similar homes.
Can you help me evaluate this property?
Yes. We can discuss condition, comparable sales, offer strategy and the questions worth asking before you decide whether to proceed.
Are property documents available?
Availability varies by property and source. Request the documents you need and we will help obtain what is available.

