18 Bennington Rd, Windham, NH 03087
Property image
Property image
OFF MARKET

18 Bennington Rd
Windham, NH 03087

  • 7 Beds
  • 5 Baths
  • 7,500 sqft (on 43 acres)

$2,981,500

Trulia Estimate
as of Aug 17, 2026

$2,981,500

Trulia Estimate
as of Aug 17, 2026
7 Beds
5 Baths
7,500 sqft
(on 43 acres)

Home Value

Trulia Estimate
$2.98M
Since last month
Decreased$77K (-2.6%)
Since last year
Increased$75K (+2.7%)
Since last sale
Increased$2M (+202.8%)
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 +200% in the last 10 years
MonthEstimated value
2026
August 2026$2.9M
July 2026$3.01M
June 2026$2.98M
May 2026$2.94M
April 2026$2.95M
March 2026$2.96M
February 2026$2.87M
January 2026$2.76M
2025
2024
2023
2022
2021
2020
2019
2018
2017

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
36 Burnham Road, Windham, NH
0.19
Single-Family Home
$1,690,000
05/15/26
5
4.5
4,653
29 Burnham Road, Windham, NH
0.23
Single-Family Home
$1,790,000
08/21/25
4
4.5
5,961
23 Bear Hill Road, Windham, NH
0.45
Single-Family Home
$959,000
08/22/25
3
2.5
3,590
10 Bear Hill Road, Windham, NH
0.44
Single-Family Home
$1,075,000
09/19/25
4
2.5
3,460
57 London Bridge Road, Windham, NH
0.82
Single-Family Home
$1,420,000
08/25/25
4
3
5,386
5 Ryan Farm Road, Windham, NH
0.68
Single-Family Home
$2,200,000
07/31/26
5
5.5
4,804
22 Ryan Farm Road, Windham, NH
0.91
Single-Family Home
$1,400,000
05/21/26
4
2.5
4,462
23 Ryan Farm Road, Windham, NH
0.85
Single-Family Home
$1,090,000
07/30/26
4
2.5
4,304
7 Wilson Road, Windham, NH
1.16
Single-Family Home
$1,087,000
08/03/26
4
2.5
3,559
138 Castle Hill Road, Windham, NH
1.14
Single-Family Home
$715,000
12/06/25
5
3.5
2,593

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
20 Bennington Road, Windham, NH 03087
0.07
$2,671,300
4
5.5
7,205
Off Market
19 Bennington Rd, Windham, NH 03087
0.13
$2,854,400
4
4.5
6,553
Off Market
21 Bennington Rd, Windham, NH 03087
0.14
$1,909,200
4
3.5
4,093
Off Market
17 Bennington Road, Windham, NH 03087
0.15
$3,100,000
4
5.5
6,511
For Sale
15 Bennington Road, Windham, NH 03087
0.16
$2,650,200
5
5.5
6,696
Off Market
32 Burnham Rd, Windham, NH 03087
0.16
$3,258,700
7
6
9,825
Off Market
30 Burnham Rd, Windham, NH 03087
0.16
$1,771,100
4
3.5
4,019
Off Market
17 Burnham Road, Windham, NH 03087
0.13
$1,388,400
4
3.5
4,473
Off Market
36 Burnham Road, Windham, NH 03087
0.19
$1,690,000
5
4.5
4,653
Recently Sold
29 Burnham Road, Windham, NH 03087
0.23
$1,823,300
4
4.5
5,961
Off Market
6 Johnny Hill Road, Windham, NH 03087
0.16
$310,000
-
-
-
Recently Sold
16 Burnham Road, Windham, NH 03087
0.24
$1,273,000
4
4
3,703
Off Market

Local Information

  • Map ViewExplore the area around 18 Bennington Rd.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2017
Lot Size
43 acres
Living Area
7,500 sqft
Price/Sqft
$398
Parking
Garage

About this House

Build your dream home nestled in the heart of the Woods of Heritage Hill. Each home will be custom designed exclusively to reflect the exquisite attention to detail, architectural elegance as well as many amenities DiPietro Homes are known for. This beautiful farmhouse is just one example of the luxury homes to be featured in this prestigious area. ONLY 3 LOTS REMAINING!
18 Bennington Rd, Windham, NH 03087 is a 7 bedroom, 6 bathroom, 7,500 sqft single-family home built in 2017. It last sold for $959,000 on Dec 19, 2016. It is currently off market. The Trulia Estimate is $2,981,500, with a rent estimate of $7,220/month.

Home Details for 18 Bennington Rd

Interior Features

Interior Details
BasementAtticNumber of Rooms: 10Types of Rooms: Walk In Closet, Breakfast Nook, Dining Room, Family Room, Laundry Room, Library, Master Bath, Mud Room, Office, Pantry, Recreation Room, Workshop, Sun Room
Heating & Cooling
Heating: Forced Air, Radiant, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 3Floors: Hardwood
Appliances & Utilities
Cable ReadyDishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
FireplaceHot Tub or SpaJetted Bath Tub
Windows, Doors, Floors & Walls
Double Paned Windows
Security
Security System

Exterior Features

Exterior Home Features
Roof: Shake ShingleDeckExterior: Shingle, Stone, Wood, Brick, Cement ConcreteLawnPatioPorchSprinkler System
Pool
Pool
Parking & Garage
GarageParking: Garage Attached, Garage Detached, Off Street, On Street

Property Information

Year Built
Year Built: 2017
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 43.00 acres

Mobile R/V

RV Parking
Rv Parking

Building

Pool
Sauna

Price and Tax history

DateEventPrice
Dec 19, 2016
Source: PrimeMLS #4493408
Sold
$959,000

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
    Flag
  • 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
    Flag
  • cb_bullock
    "Snob Quotient very high. Has become over-built Easy access to rte 93; state rtes 111, 128, 3"
    0
    Flag
  • karting4fun
    "The area is well kept, quiet, friendly, and clean. Very close to schools. "
    0
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Apartments for Rent

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6 rentals with a washer/dryer in Windham, NH

Homes for sale near 18 Bennington Rd

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Off Market Homes Near 18 Bennington Rd

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Frequently asked questions about 18 Bennington Rd

  • What is 18 Bennington Rd estimated to be worth?
    Trulia's estimated value for 18 Bennington Rd in Windham, NH is $2,981,500.
  • What is the price history for 18 Bennington Rd?
    18 Bennington Rd in Windham, NH last sold for $959,000 in December 2016.
  • 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 18 Bennington Rd have air conditioning?
    Yes, 18 Bennington Rd in Windham, NH has air conditioning.
  • Does 18 Bennington Rd have a pool?
    Yes, 18 Bennington Rd in Windham, NH has a pool.