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    • Listed by: DiPietro Group Real Estate • Shannon DiPietro
    Price cut: $99K (7/30)
    $1,500,000

    5 Sherwood Road, Windham, NH 03087

    4beds
    5,112sqft
    : 
    $9,503/mo
    Get pre-qualified
    Single Family Residence
    Built in 1999
    3.79 Acres Lot
    $1,457,700 Zestimate®
    $293/sqft
    $-- HOA

    What's special

    Private home officeSpectacular gunite inground poolCentral air conditioning throughoutExpansive composite deckCustom cabinet-front refrigeratorCustom millwork throughoutElegant formal dining room
    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. It is 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 spectacular gunite inground pool surrounded by professionally designed 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.
    18 days
    |
    2,805
    |
    137
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Shannon DiPietro,

    DiPietro Group Real Estate 603-216-5086

    Source: PrimeMLS,MLS#: 5099575MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 4
      • Full bathrooms: 2
      • 3/4 bathrooms: 1
      • 1/2 bathrooms: 1
      Heating
      • Propane, Oil, Solar, Wood, Electric, Forced Air, Wood Stove, Mini Split
      Cooling
      • Central Air, Zoned, Wall Unit(s), Mini Split
      Appliances
      • Included: Down Draft Cooktop, Gas Cooktop, Microwave, Wall Oven, Refrigerator, Washer, Water Heater off Boiler, Oil Water Heater, Tank Water Heater, Gas Dryer, Vented Exhaust Fan, Water Heater
      • Laundry: 1st Floor Laundry
      Features
      • Central Vacuum, Bar, Ceiling Fan(s), Dining Area, In-Law Suite, Kitchen Island, LED Lighting, Primary BR w/ BA, Natural Light, Soaking Tub, Wired for Sound, Walk-In Closet(s), Smart Thermostat
      • Flooring: Bamboo, Carpet, Ceramic Tile, Hardwood, Laminate
      • Windows: Blinds, Screens, Double Pane Windows
      • Basement: Finished,Insulated,Interior Stairs,Walkout,Interior Access,Exterior Entry,Walk-Out Access
      • Attic: Pull Down Stairs
      • Number of fireplaces: 1
      • Fireplace features: 1 Fireplace, Wood Stove Insert
      Interior area
      • Total structure area: 6,154
      • Total interior livable area: 5,112 sqft
      • Finished area above ground: 3,948
      • Finished area below ground: 1,164

      Property

      Parking
      • Total spaces: 3
      • Parking features: Paved, Assigned, Driveway, Garage
      • Garage spaces: 3
      • Has uncovered spaces: Yes
      Accessibility
      • Accessibility features: 1st Floor 1/2 Bathroom, 1st Floor Hrd Surfce Flr, 1st Floor Laundry
      Features
      • Levels: Two
      • Stories: 2
      • Patio & porch: Patio, Porch
      • Exterior features: Deck, Storage
      • Has private pool: Yes
      • Pool features: In Ground
      • Has spa: Yes
      • Spa features: Heated, Bath
      • Fencing: Dog Fence,Partial
      • Frontage length: Road frontage: 233
      Lot
      • Size: 3.79 Acres
      • Features: Landscaped, Wooded
      Details
      • Parcel number: WNDMM11BAL235
      • Zoning description: RD
      • Other equipment: Radon Mitigation, Standby Generator

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Colonial
      • Property subtype: Single Family Residence
      Materials
      • Wood Frame, Clapboard Exterior
      • Foundation: Concrete
      • Roof: Architectural Shingle,Asphalt Shingle
      Condition
      • New construction: No
      • Year built: 1999

      Utilities & green energy

      • Electric: 200+ Amp Service, Circuit Breakers, Generator, Off Grid, Net Meter, Energy Storage Device
      • Sewer: 1500+ Gallon, Leach Field, On-Site Septic Exists, Private Sewer
      • Utilities for property: Cable, Propane, Other

      Community & HOA

      Community
      • Security: Carbon Monoxide Detector(s), HW/Batt Smoke Detector
      Location
      • Region: Windham

      Financial & listing details

      • Price per square foot: $293/sqft
      • Tax assessed value: $1,429,000
      • Annual tax amount: $20,220
      • Date on market: 7/13/2026
      • Road surface type: Paved

        Estimated market value

        $1,457,700

        $1.38M - $1.53M

        $7,552/mo

        Price history

        DateEventPrice
        7/30/2026Price change$1,500,000-6.2%$293/sqft
        Source: PrimeMLS #5099575 Report a problem
        7/15/2026Listed for sale$1,599,000+106.4%$313/sqft
        Source: PrimeMLS #5099575 Report a problem
        10/11/2016Sold$774,800-3.1%$152/sqft
        Source: PrimeMLS #4503373 Report a problem
        8/8/2016Pending sale$799,900$156/sqft
        Source: Coldwell Banker Dinsmore Associates #4503373 Report a problem
        7/11/2016Listed for sale$799,900-3.5%$156/sqft
        Source: Coldwell Banker Dinsmore Associates #4503373 Report a problem
        4/2/2010Listing removed$829,000$162/sqft
        Source: George Dinsmore Associates, Inc. DBA Prudential Dinsmore Associates, REALTORS #2783538 Report a problem
        2/18/2010Price change$829,000-3.6%$162/sqft
        Source: George Dinsmore Associates, Inc. DBA Prudential Dinsmore Associates, REALTORS #2783538 Report a problem
        9/2/2009Price change$859,900-4.4%$168/sqft
        Source: George Dinsmore Associates, Inc. DBA Prudential Dinsmore Associates, REALTORS #2783538 Report a problem
        6/20/2009Listed for sale$899,900+649.9%$176/sqft
        Source: George Dinsmore Associates, Inc. DBA Prudential Dinsmore Associates, REALTORS #2783538 Report a problem
        12/1/1998Sold$120,000$23/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2024$18,490 +5.8%$816,700
        2023$17,477 +8.3%$816,700
        2022$16,138 +5%$816,700 +1.6%
        2020$15,371 +12.1%$803,500 +32.1%
        2019$13,715 -3.2%$608,200
        2018$14,165 +16%$608,200 +0.6%
        2017$12,209 -7.4%$604,400
        2016$13,188 -0.1%$604,400 -0.5%
        2015$13,197 -13.4%$607,600 -4.4%
        2014$15,247 -4.7%$635,300 -6.3%
        2013$15,998 +2.4%$677,900
        2012$15,626 -0.1%$677,900
        2011$15,646 +8.6%$677,900 +3.4%
        2010$14,403 +16.7%$655,300 -4.5%
        2008$12,346 +11.2%$685,900 -0.6%
        2007$11,106 $689,800
        Find assessor info on the county website

        Monthly payment

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        Payment breakdown

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        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
        Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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        Climate risks

        Neighborhood: 03087

        Getting around

        0 / 100
        Car-Dependent
        3 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating

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