20 Bennington Road, Windham, NH 03087
Property image
Property image
OFF MARKET
Listed by Amber L Tomlin, Keller Williams Realty-Metropolitan, (603) 232-8282 . Bought with EXP Realty

$2,643,700

Trulia Estimate
  • 4 Beds
  • 5.5 Baths
  • 7,205 sqft (on 2.85 acres)

20 Bennington Road, Windham, NH 03087

Refinance Your Home
Currently Off Market - Sold Aug 5, 2024 for $2,430,000

Home Value

Trulia Estimate
$2.64M
Since last month
Decreased$15K (-0.6%)
Since last year
Increased$147K (+5.9%)
Since last sale
Increased$226K (+9.3%)
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 +104% in the last 10 years
MonthEstimated value
2026
September 2026$2.66M
August 2026$2.67M
July 2026$2.67M
June 2026$2.65M
May 2026$2.69M
April 2026$2.66M
March 2026$2.64M
February 2026$2.54M
January 2026$2.54M
2025
2024
2023
2022
2021
2020
2019
2018

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
0.12
Single-Family Home
$1,690,000
05/15/26
5
4.5
4,653
5 Ryan Farm Road, Windham, NH
0.74
Single-Family Home
$2,200,000
07/31/26
5
5.5
4,804
22 Ryan Farm Road, Windham, NH
0.96
Single-Family Home
$1,400,000
05/21/26
4
2.5
4,462
23 Ryan Farm Road, Windham, NH
0.90
Single-Family Home
$1,090,000
07/30/26
4
2.5
4,304
6 Westchester Road, Windham, NH
1.08
Single-Family Home
$1,360,000
04/24/26
4
3
4,188
54 Sharon Road, Windham, NH
1.59
Single-Family Home
$1,850,000
07/02/26
5
5.5
6,807
63 Mammoth Road, Windham, NH
1.44
Single-Family Home
$2,000,000
03/20/26
4
3.5
4,854
6 Lancaster Road, Windham, NH
0.76
Single-Family Home
$4,200,000
12/18/25
7
8.5
13,907
20 Cobbetts Pond Road, Windham, NH
1.28
Single-Family Home
$1,299,000
07/23/26
4
3.5
3,743

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
21 Bennington Rd, Windham, NH 03087
0.07
$1,885,300
4
3.5
4,093
Off Market
19 Bennington Rd, Windham, NH 03087
0.07
$2,821,600
4
4.5
6,553
Off Market
32 Burnham Rd, Windham, NH 03087
0.09
$3,287,400
7
6
9,825
Off Market
30 Burnham Rd, Windham, NH 03087
0.10
$1,753,700
4
3.5
4,019
Off Market
36 Burnham Road, Windham, NH 03087
0.12
$1,690,000
5
4.5
4,653
Recently Sold
17 Bennington Rd, Windham, NH 03087
0.11
$2,800,000
4
5.5
6,511
For Sale
15 Bennington Road, Windham, NH 03087
0.14
$2,621,100
5
5.5
6,696
Off Market
29 Burnham Road, Windham, NH 03087
0.17
$1,839,200
4
4.5
5,961
Off Market
48 Burnham Road, Windham, NH 03087
0.28
$1,217,300
5
2.5
3,204
Off Market
6 Johnny Hill Road, Windham, NH 03087
0.23
$310,000
-
-
-
Recently Sold
16 Burnham Road, Windham, NH 03087
0.26
$1,299,600
4
4
3,703
Off Market

Local Information

  • Map ViewExplore the area around 20 Bennington Road.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2017
2.85 acre lot
7,205 sqft
$367/sqft
Garage

About this House

IMMERSE YOURSELF IN LUXURY|Located in one of Windham, NH’s most sought-after neighborhoods, this custom colonial features finishes like no other. Handcrafted with the utmost attention to detail, this home offers over 7,000 sq ft of elegance. Upon entering, you will be greeted by soaring ceilings, gleaming hardwood floors, and a breathtaking foyer. Designed for comfort and entertaining, this floor plan provides an unparalleled living experience that includes a formal dining room, a study complete with a gas fireplace, and a family room that boasts an exquisite handmade entertainment center, gas fireplace, and coffered ceilings. The kitchen is the heart of the home, and this one is a culinary enthusiast’s dream! It features Brazilian quartzite countertops, an oversized island, top-of-the-line appliances, striking lighting fixtures, an oversized pantry, and stunning customized cherry cabinetry.The second level is complete with three en-suite bedrooms and a primary suite featuring a fireplace, soaking tub, and walk-in shower. Make your way to the lower level, where you will find a game room, home theater, bar, home gym, and flex space that could double as an additional guest room.This property also features an oversized three-car garage, large deck and patio for entertaining, and a private elevator that provides easy access to any level of the home. Showing to begin Saturday June 8th by appointment.
20 Bennington Road, Windham, NH 03087 is a 4 bedroom, 6 bathroom, 7,205 sqft single-family home built in 2017. It last sold for $2,430,000 on Aug 5, 2024 (3% below the $2,495,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,643,700, with a rent estimate of $8,391/month.

Home Details for 20 Bennington Road

Active Status

MLS Status: Closed

Interior Features

Interior Details
Basement: Finished,Walkout,Walk-Out AccessNumber of Rooms: 10
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 6Number of Bathrooms (full): 2Number of Bathrooms (three quarters): 3Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 7205 Square Feet
Appliances & Utilities
Utilities: CableAppliances: Gas Cooktop, Dishwasher, Dryer, Range Hood, Freezer, Microwave, Mini Fridge, Double Oven, Gas Range, Refrigerator, Washer, Gas StoveDishwasherDryerMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Propane,Forced AirHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Propane
Fireplace & Spa
Fireplace: Gas, 3+ FireplacesHas a Fireplace
Gas & Electric
Electric: Circuit Breakers
Windows, Doors, Floors & Walls
Window: DrapesFlooring: Carpet, Tile, Wood
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoAccessibility: Paved ParkingElevatorFloors: Carpet, Tile, Wood
View
No View

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: PatioExterior: DeckFoundation: Concrete
Parking & Garage
Number of Garage Spaces: 3Number of Covered Spaces: 3Has a GarageParking Spaces: 3Parking: Paved
Frontage
Road Frontage: Public
Water & Sewer
Sewer: Septic Tank
Farm & Range
Frontage Length: Road frontage: 235
Finished Area
Finished Area (above surface): 5029 Square FeetFinished Area (below surface): 2176 Square Feet

Property Information

Year Built
Year Built: 2017
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Construction Materials: Wood FrameNot a New Construction
Property Information
Not Included in Sale: Basement Freezer, Theater Seating, Basement Bar Please see attached inclusions/exclusions list

Price & Status

Price
List Price: $2,495,000

Location

Direction & Address
City: Windham
School Information
Elementary School: Golden Brook Elementary SchoolElementary School District: WindhamJr High / Middle School: Windham Middle SchoolJr High / Middle School District: WindhamHigh School: Windham High SchoolHigh School District: Windham

Building

Building Area
Building Area: 7205 Square Feet

Lot Information

Lot Area: 2.85 Acres

Miscellaneous

BasementMls Number: 4998946Above Grade Unfinished Area: 5029Above Grade Unfinished Area Units: Square FeetBelow Grade Unfinished Area Source: Public RecordsBelow Grade Unfinished Area Units: Square Feet

Price and Tax history

DateEventPrice
Aug 5, 2024
Source: PrimeMLS #4998946
Sold
$2,430,000
Jun 12, 2024
Source: PrimeMLS #4998946
Contingent
$2,495,000
Jun 5, 2024
Source: PrimeMLS #4998946
Listed For Sale
$2,495,000
Aug 30, 2017
Source: PrimeMLS #4637894
Sold
$1,248,527
Mar 17, 2017
Source: N/A
Sold
$198,000

Market trends in Windham

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
50
2MoM

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
    Flag

LGBTQ Local Legal Protections

Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated 2026-09-22 01:14:43 PDT.
This display of listings may or may not be the entire Compilation from the PrimeMLS database, and PrimeMLS does not guarantee the accuracy of such information.

Frequently asked questions about 20 Bennington Road

  • What is 20 Bennington Road estimated to be worth?
    Trulia's estimated value for 20 Bennington Road in Windham, NH is $2,643,700.
  • What is the price history for 20 Bennington Road?
    20 Bennington Road in Windham, NH last sold for $2,430,000 in August 2024.
  • Is Windham a buyer's or seller's market?
    Windham is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Windham?
    Residents describe Windham, NH as dog-friendly, easy to park in, and quiet. Most residents say you need a car. See recently sold homes in Windham, NH.
  • Does 20 Bennington Road have air conditioning?
    Yes, 20 Bennington Road in Windham, NH has air conditioning.
  • Does 20 Bennington Road have laundry facilities?
    Yes, 20 Bennington Road in Windham, NH has in-unit laundry.

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 20 Bennington Road

Skip to last item
Skip to first item

Homes for sale near 20 Bennington Road

Skip to last item
Skip to first item
Skip to last item
  • Results are loading
Skip to first item