5 Chestnut St, Windham, NH 03087
OFF MARKET

5 Chestnut St
Windham, NH 03087

  • 5 Beds
  • 4.5 Baths
  • 8,106 sqft (on 3.13 acres)

$2,086,100

Trulia Estimate
as of Aug 14, 2026

$2,086,100

Trulia Estimate
as of Aug 14, 2026
5 Beds
4.5 Baths
8,106 sqft
(on 3.13 acres)

Home Value

Trulia Estimate
$2.09M
Since last month
Decreased$9K (-0.4%)
Since last year
Increased$52K (+2.6%)
Since last sale
Increased$878K (+72.6%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +106% in the last 10 years
MonthEstimated value
2026
August 2026$2.09M
July 2026$2.09M
June 2026$2.1M
May 2026$2.06M
April 2026$2.05M
March 2026$2.04M
February 2026$1.96M
January 2026$1.91M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
18 Hawthorne Road, Windham, NH
0.23
Single-Family Home
$1,150,000
05/18/26
4
3.5
4,708
5 Highclere Road, Windham, NH
0.23
Single-Family Home
$1,680,745
10/03/25
4
3.5
3,617
18 Highclere Rd, Windham, NH
0.31
Single-Family Home
$1,450,000
06/23/26
4
3.5
4,029
11 Park Street, Windham, NH
0.26
Single-Family Home
$700,000
01/07/26
4
2.5
2,602
9 Floral Street, Windham, NH
0.80
Single-Family Home
$2,200,000
05/01/26
5
4.5
6,112
89 Kendall Pond Road, Windham, NH
0.90
Single-Family Home
$910,000
08/18/25
5
4.5
4,188
88 Meetinghouse Road, Windham, NH
0.53
Single-Family Home
$745,000
06/18/26
4
2
2,651
14 Park Street, Windham, NH
0.21
Single-Family Home
$725,000
11/04/25
3
2
2,020
3 Hillside Road, Windham, NH
0.72
Single-Family Home
$874,000
08/06/26
4
3
3,130
22 Kent Street, Windham, NH
1.04
Single-Family Home
$1,160,000
07/15/26
4
2.5
3,400

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
35 Hawthorne Road, Windham, NH 03087
0.12
$2,139,000
5
4.5
7,709
Off Market
23 Hawthorne Road, Windham, NH 03087
0.15
$1,521,400
4
3.5
5,719
Off Market
41 Hawthorne Rd, Windham, NH 03087
0.19
$1,664,100
6
3.5
6,760
Off Market
5 Highclere Road, Windham, NH 03087
0.23
$1,714,100
4
3.5
3,617
Off Market
18 Hawthorne Road, Windham, NH 03087
0.23
$1,150,000
4
3.5
4,708
Recently Sold
14 Park Street, Windham, NH 03087
0.21
$725,000
3
2
2,020
Recently Sold
11 Highclere Road, Windham, NH 03087
0.27
$1,870,400
4
3.5
5,140
Off Market
15 Highclere Road, Windham, NH 03087
0.30
$2,207,600
4
5
6,982
Off Market
17 Park Street, Windham, NH 03087
0.26
$674,000
4
2
2,288
Off Market
18 Highclere Rd, Windham, NH 03087
0.31
$1,450,000
4
3.5
4,029
Recently Sold
17 Highclere, Windham, NH 03037
0.31
$1,663,500
4
2.5
4,666
Off Market
17 Highclere Rd, Windham, NH 03087
0.31
$1,663,500
4
2.5
4,666
Off Market

Local Information

  • Map ViewExplore the area around 5 Chestnut St.
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Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1998
Lot Size
3.13 acres
Living Area
8,106 sqft
Price/Sqft
$257
Parking
Garage

About this House

This elegant, luxury estate home features a masterful design, impeccable condition and fine details and amenities. As soon as you approach the grand entrance hall and begin to understand the refined grace and sophistication that this home offers, you'll want to make this the setting for your unique story to unfold. Set proudly on a park-like lot of over 3 acres, with extensive, well-planned and inspired hardscapes, gardens and landscape details the grounds boast a free-form in-ground heated swimming pool, spa and tennis court/basketball court. As you explore this residence, one of the first things you'll notice is the spacious and well-proportioned rooms. The second thing that will impress you is the attention to detail and the exceptional craftsmanship throughout. The lower level suite with oversized windows and a view to the gardens is a great area to entertain or to allow your guests their privacy (en-suite with complete kitchen). Enjoy the changing seasons from the wonderful sunroom and the screened porch poolside. Finally, you'll appreciate the convenience of the 4-car garage. The photographs will just barely whet your appetite for this beautiful residence until you can view and enjoy the property for yourself. Assisted and by appointment only.
5 Chestnut St, Windham, NH 03087 is a 5 bedroom, 5 bathroom, 8,106 sqft single-family home built in 1998. It last sold for $1,210,000 on May 17, 2019. It is currently off market. The Trulia Estimate is $2,086,100, with a rent estimate of $7,686/month.

Home Details for 5 Chestnut St

Interior Features

Interior Details
BasementNumber of Rooms: 14Types of Rooms: Walk In Closet
Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Carpet, Hardwood
Appliances & Utilities
DishwasherRefrigerator
Fireplace & Spa
FireplaceHot Tub or Spa

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Other, StonePatio
Pool
Pool
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1998Year Updated: 2008
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 3.13 acres

Building

Fitness & Sports
Tennis Court

Price and Tax history

DateEventPrice
May 17, 2019
Source: PrimeMLS #4752328
Sold
$1,210,000
Jul 5, 2018
Source: Agent Provided
Listed For Sale
$1,260,000
Nov 4, 2015
Source: N/A
Sold
$975,000
Sep 26, 2015
Source: Agent Provided
Pending
$1,075,000
Jul 29, 2015
Source: Agent Provided
PriceChange
$1,075,000
Price decreased by 7%

Market trends in Windham

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$730K
$51.67KMoM
Sale-to-List Price
101.6%
0.7%MoM
Price per sq ft
$312
$8MoM
Available listings
52
6MoM
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Around this home

What Locals Say about Windham

At least 42 Trulia users voted on each feature.

  • 96 % Say car is needed

  • 94 % Say it's dog friendly

  • 92 % Say parking is easy

  • 89 % Say people would walk alone at night

  • 88 % Say it's quiet

  • 87 % Say there's holiday spirit

  • 85 % Say yards are well-kept

  • 82 % Say there's wildlife

  • 69 % Say kids play outside

  • 61 % Say neighbors are friendly

  • 53 % Say they plan to stay for at least 5 years

  • 52 % Say there are community events

  • 14 % Say streets are well-lit

  • 13 % Say it's walkable to grocery stores

  • 12 % Say there are sidewalks

Sourced by Trulia users. Learn more about our methodology.
  • M Rideout
    "Nicest town in New Hampshire by far, safe, good schools, easy access to 93. Taxes are high but you get what you pay for I guess. "
    0
    Flag
  • Viren.patel
    "You see dog owners walking here all the time. Everyone is so friendly & nice that you feel like a part of one big family. "
    1
    Flag
  • Renee C.
    "Recreation department has a lot of town events at the park at the library They have dog Halloween parade Town beach hs many water activity’s "
    5
    Flag
  • Caitlinschiffer
    "Strawberry Festival, concerts in the common, Griffen Park sports and recreation fields, tennis, basketball. Great community restaurants, Old School, Reds Tavern, Common Man, Windham Restuarant. "
    5
    Flag
  • Tammy V.
    "all the dogs in my neighborhood are small and friendly, everyone picks up after their dogs for the most part. "
    2
    Flag
  • Morgan.pm
    "Everyone has a dog and everyone knows all the neighbors dogs names and they are all friends. Okay people allow their dogs to run around leash free during the day. A great neighborhood for walking your dogs. Everyone is super friendly. Everyone cleans up after their pups"
    2
    Flag
  • Rebekah S.
    "Lots of room to run in yards, lots of doggy friends and neighbors, lots of great vets and hospitals and safe to walk on road anytime of day "
    3
    Flag
  • 13mnesti
    "Quiet small town community with all the necessary shops, delicious restaurants, and close proximity to the mountains, beach, and city "
    2
    Flag
  • Vismay S.
    "It’s an awesome town to raise kids & live your entire life in. It is very conveniently located suburb. "
    4
    Flag
  • deborahemyers
    "I think it is a little piece of heaven close enough to Boston to be worth the extra 1/2 hour drive from a "normal" commute."
    0
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  • deborahemyers
    "Used to live there and going back ASAP. Windham has spoiled me for other areas, if you need to be in the southern New Hampshire, or Boston area at all. "
    0
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  • cb_bullock
    "Snob Quotient very high. Has become over-built Easy access to rte 93; state rtes 111, 128, 3"
    0
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  • karting4fun
    "The area is well kept, quiet, friendly, and clean. Very close to schools. "
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Homes for sale near 5 Chestnut St

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Off Market Homes Near 5 Chestnut St

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Frequently asked questions about 5 Chestnut St

  • What is 5 Chestnut St estimated to be worth?
    Trulia's estimated value for 5 Chestnut St in Windham, NH is $2,086,100.
  • What is the price history for 5 Chestnut St?
    5 Chestnut St in Windham, NH last sold for $1,210,000 in May 2019.
  • Is Windham a buyer's or seller's market?
    Windham is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Windham?
    The median sale price in Windham is $730K. That is up $51.67K from the prior month.
  • Does 5 Chestnut St have air conditioning?
    Yes, 5 Chestnut St in Windham, NH has air conditioning.
  • Does 5 Chestnut St have a pool?
    Yes, 5 Chestnut St in Windham, NH has a pool.