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

21 Bennington Rd
Windham, NH 03087

  • 4 Beds
  • 3.5 Baths
  • 4,093 sqft (on 3.18 acres)

$1,909,200

Trulia Estimate
as of Aug 22, 2026

$1,909,200

Trulia Estimate
as of Aug 22, 2026
4 Beds
3.5 Baths
4,093 sqft
(on 3.18 acres)

Home Value

Trulia Estimate
$1.91M
Since last month
Decreased$6K (-0.3%)
Since last year
Increased$68K (+3.7%)
Since last sale
Increased$158K (+9.1%)
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 +116% in the last 10 years
MonthEstimated value
2026
August 2026$1.9M
July 2026$1.9M
June 2026$1.89M
May 2026$1.92M
April 2026$1.88M
March 2026$1.9M
February 2026$1.83M
January 2026$1.8M
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
0.07
Single-Family Home
$1,690,000
05/15/26
5
4.5
4,653
0.54
Single-Family Home
$1,075,000
09/19/25
4
2.5
3,460
0.69
Single-Family Home
$1,420,000
08/25/25
4
3
5,386
0.99
Single-Family Home
$1,400,000
05/21/26
4
2.5
4,462
0.77
Single-Family Home
$2,200,000
07/31/26
5
5.5
4,804
0.93
Single-Family Home
$1,090,000
07/30/26
4
2.5
4,304
1.08
Single-Family Home
$1,360,000
04/24/26
4
3
4,188
1.30
Single-Family Home
$1,299,000
07/23/26
4
3.5
3,743
1.09
Single-Family Home
$950,000
06/29/26
3
2.5
2,962
1.29
Single-Family Home
$1,087,000
08/03/26
4
2.5
3,559

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
0.07
$2,662,200
4
5.5
7,205
Off Market
0.04
$2,854,400
4
4.5
6,553
Off Market
0.08
$3,258,700
7
6
9,825
Off Market
0.10
$1,771,100
4
3.5
4,019
Off Market
0.07
$1,690,000
5
4.5
4,653
Recently Sold
0.09
$3,100,000
4
5.5
6,511
For Sale
0.13
$2,650,200
5
5.5
6,696
Off Market
0.11
$1,823,300
4
4.5
5,961
Off Market
0.20
$1,382,100
4
3.5
4,473
Off Market
0.22
$1,233,500
5
2.5
3,204
Off Market
0.30
$310,000
-
-
-
Recently Sold

Local Information

  • Map ViewExplore the area around 21 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
2010
Lot Size
3.18 acres
Living Area
4,093 sqft
Price/Sqft
$466
Parking
3 Car Garage

About this House

EXQUISITE Executive Estate nestled within one of Windham NH's premier neighborhoods. Situated on 3+ acre corner lot, Sprawling Cape-style home boasts an unparalleled level of luxury & sophistication. Lush, meticulously maintained landscaping, timeless elegance & superior craftsmanship defines every corner of this home. Grand foyer w/ its soaring ceilings, wide plank hickory floors, & gracefully turned staircase sets stage for rest of the residence. Heart of the home is undoubtedly floor-to-ceiling family room, a truly exceptional space where natural light pours in through expansive windows. Adjacent gourmet kitchen featuring subzero/wolf appliances, custom cabinetry, granite countertops & spacious island. 1st level primary suite, stunning dining room, private office & secondary entrance complete this level. 3 bedrms, bonus room w/guest room & 2 private baths are located on 2nd level. Expansive rear yard features spacious deck & patio, perfect for entertaining or a quiet retreat.
21 Bennington Rd, Windham, NH 03087 is a 4 bedroom, 4 bathroom, 4,093 sqft single-family home built in 2010. It last sold for $1,740,000 on Feb 14, 2024 (6% below the $1,849,000 asking price). It is currently off market. The Trulia Estimate is $1,909,200, with a rent estimate of $6,941/month.
Last check for updates: about 3 hours ago
Listed by Christine Carey, (603) 943-0014
DiPietro Group Real Estate, (603) 216-5086
Bought with: Darlene Couture, (978) 490-7961, Berkshire Hathaway HomeServices Verani Realty Salem, (603) 890-3226
Source: MLS PIN, MLS#73171717

Home Details for 21 Bennington Rd

Interior Features

Interior Details
Basement: Full,Bulkhead,Radon Remediation SystemNumber of Rooms: 12Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Master Bathroom, Dining Room, Family Room, Kitchen, OfficeWet Bar
Beds & Baths
Number of Bedrooms: 4Main Level Bedrooms: 1Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 4093 Square Feet
Appliances & Utilities
Utilities: for Gas Range, Washer Hookup, Generator ConnectionAppliances: Water Heater, Range, Microwave, Refrigerator, Washer, Dryer, Vacuum System, Range HoodDryerLaundry: Closet/Cabinets - Custom Built,Flooring - Stone/Ceramic Tile,Electric Dryer Hookup,Washer Hookup,First FloorMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Forced Air,Propane,Fireplace(s)Has CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 2Fireplace: Family RoomHas a FireplaceNo Spa
Gas & Electric
Electric: 200+ Amp Service, Generator Connection
Windows, Doors, Floors & Walls
Door: French DoorsFlooring: Tile, Carpet, Hardwood, Flooring - Wall to Wall Carpet, Flooring - Stone/Ceramic Tile
Levels, Entrance, & Accessibility
Floors: Tile, Carpet, Hardwood, Flooring Wall To Wall Carpet, Flooring Stone Ceramic Tile
Security
Security: Security System

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Deck - Wood, PatioExterior: Deck - Wood, Patio, Professional Landscaping, Sprinkler SystemFoundation: Concrete PerimeterSprinkler System
Parking & Garage
Number of Garage Spaces: 3Number of Covered Spaces: 3Open Parking Spaces: 6No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 9Parking: Attached,Garage Door Opener,Paved Drive,Paved
Frontage
Waterfront: Lake/Pond, 1/10 to 3/10 To Beach, Beach Ownership(Public)Road Frontage: PublicNot on Waterfront
Water & Sewer
Sewer: Private Sewer

Property Information

Year Built
Year Built: 2010
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Cape
Building
Construction Materials: FrameNot Attached PropertyDoes Not Include Home Warranty
Property Information
Parcel Number: 972968

Price & Status

Price
List Price: $1,849,000
Status Change & Dates
Off Market Date: Mon Jan 15 2024

Active Status

MLS Status: Sold

Location

Direction & Address
City: Windham
School Information
Elementary School: Golden BrookJr High / Middle School: Windham MiddleHigh School: Windham High

Building

Building Area
Building Area: 4093 Square Feet

Community

Community Features: Shopping, Tennis Court(s), Park, Walk/Jog Trails, Golf, Bike Path, Highway Access, House of Worship, Public SchoolNot Senior Community

HOA

No HOA

Lot Information

Lot Area: 3.18 Acres

Offer

Contingencies: Inspection

Miscellaneous

BasementMls Number: 73171717

Additional Information

ShoppingTennis Court(s)ParkWalk/Jog TrailsGolfBike PathHighway AccessHouse of WorshipPublic School

Price and Tax history

DateEventPrice
Feb 14, 2024
Source: MLS PIN #73171717
Sold
$1,740,000
Jan 1, 2024
Source: PrimeMLS #4973112
ListingRemoved
Nov 29, 2023
Source: MLS PIN #73171717
ListingRemoved
$1,849,000
Oct 18, 2023
Source: PrimeMLS #4973112
PriceChange
$1,849,000
Price decreased by 6%
Oct 6, 2023
Source: PrimeMLS #4973112
Listed For Sale
$1,975,000

Market trends in Windham

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

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. "
  • 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. "
  • 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 "
  • 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. "
  • Tammy V.
    "all the dogs in my neighborhood are small and friendly, everyone picks up after their dogs for the most part. "
  • 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"
  • 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 "
  • 13mnesti
    "Quiet small town community with all the necessary shops, delicious restaurants, and close proximity to the mountains, beach, and city "
  • Vismay S.
    "It’s an awesome town to raise kids & live your entire life in. It is very conveniently located suburb. "
  • 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."
  • 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. "
  • cb_bullock
    "Snob Quotient very high. Has become over-built Easy access to rte 93; state rtes 111, 128, 3"
  • karting4fun
    "The area is well kept, quiet, friendly, and clean. Very close to schools. "

LGBTQ Local Legal Protections

The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
The MLS listing information displayed is deemed reliable, but is not guaranteed accurate by the MLS.

Frequently asked questions about 21 Bennington Rd

  • What is 21 Bennington Rd estimated to be worth?
    Trulia's estimated value for 21 Bennington Rd in Windham, NH is $1,909,200.
  • What is the price history for 21 Bennington Rd?
    21 Bennington Rd in Windham, NH last sold for $1,740,000 in February 2024.
  • 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 21 Bennington Rd have air conditioning?
    Yes, 21 Bennington Rd in Windham, NH has air conditioning.
  • Does 21 Bennington Rd have laundry facilities?
    Yes, 21 Bennington Rd in Windham, NH has in-unit laundry.

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