Listed by DiPietro Group Real Estate, Shannon DiPietro, (603) 216-5086
$2,750,000
4 Beds
5.5 Baths
7,205 sqft (on 2.85 acres)
20 Bennington Road, Windham, NH 03087
Est. Mortgage $17,830/mo*
Get Pre-QualifiedHome Highlights
Single-Family Home
Built in 2017
2.85 acre lot
$382/sqft
Garage
Local Information
- Map ViewExplore the area around 20 Bennington Road.
- Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
- Shop & Eat
-- mins to
About this House
What's unique:Garage with ev chargingBeautifully appointed interiorsClassic architectureSoaring ceilingsImpressive architectural detailsExtensive custom millwork
TIMELESS ELEGANCE. Exceptional craftsmanship. Luxury on a grand scale. This extraordinary custom-built residence offers over 7,000 square feet of sophisticated living space, where classic architecture, exquisite craftsmanship, and attention to detail create a home of remarkable distinction. From the moment you enter, the grandeur is undeniable. Soaring ceilings, impressive architectural details, extensive custom millwork, and beautifully appointed interiors showcase a level of craftsmanship rarely found in today's homes. The spectacular chef's kitchen is a culinary dream, featuring exceptional design, a large built-in French door refrigerator, and the perfect setting for everything from intimate gatherings to lavish entertaining. Expansive living spaces are designed to entertain on the grandest of scales, while French doors provide access to the deck and lower level, creating a seamless connection to the outdoors. A fully equipped private movie theatre with nine seats and audiovisual equipment delivers an exceptional cinematic experience. The dedicated fitness room, complete with mirrors, treadmill, Tonal workout system, and elliptical, brings the convenience of a private gym home. Four beautifully appointed en-suite bedrooms provide luxurious private retreats, while an elevator offers effortless access between levels. Additional amenities include a garage with EV charging and a whole-house water softening system. Rich in character, grand in scale, and extraordinary in every detail, this residence is a celebration of timeless architecture and refined living. A rare opportunity to experience a level of craftsmanship and elegance that truly sets this home apart.
Home Details for 20 Bennington Road
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Interior Details Basement: Climate Controlled,Daylight,Finished,Full,Storage Space,Walkout,Interior Access,Exterior Entry,Basement Stairs,Walk-Out AccessNumber of Rooms: 10Wet Bar |
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: ENERGY STAR Qualified Dishwasher, Disposal, ENERGY STAR Qualified Dryer, Range Hood, Freezer, Microwave, Double Oven, Gas Range, Refrigerator, ENERGY STAR Qualified Washer, Gas Water Heater, Exhaust FanDishwasherDisposalLaundry: 1st Floor LaundryMicrowaveRefrigerator |
Heating & Cooling Heating: Propane,Forced Air,ZonedHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Propane |
Fireplace & Spa Fireplace: 3+ FireplacesHas a Fireplace |
Gas & Electric Electric: Circuit Breakers |
Windows, Doors, Floors & Walls Window: Drapes, Screens, Double Pane WindowsFlooring: Carpet, Ceramic Tile, Hardwood |
Levels, Entrance, & Accessibility Stories: 2Levels: TwoAccessibility: 1st Floor 1/2 Bathroom, 1st Floor Hrd Surfce Flr, Access to Common Areas, Laundry Access w/No Steps, Access to Parking, 1st Floor LaundryElevatorFloors: Carpet, Ceramic Tile, Hardwood |
View No View |
Security Security: Security, Carbon Monoxide Detector(s), Security System, Smoke Detector(s) |
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Exterior Home Features Roof: Architectural ShinglePatio / Porch: Patio, PorchExterior: DeckFoundation: Poured Concrete |
Parking & Garage Number of Garage Spaces: 3Number of Covered Spaces: 3No CarportHas a GarageHas Open ParkingParking Spaces: 3Parking: Paved,Driveway,Garage |
Frontage Road Frontage: PublicResponsible for Road Maintenance: Public Maintained RoadRoad Surface Type: Paved |
Water & Sewer Sewer: Septic Tank |
Farm & Range Frontage Length: Road frontage: 172 |
Finished Area Finished Area (above surface): 5029 Square FeetFinished Area (below surface): 2176 Square Feet |
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Days on Market: 35 |
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Year Built Year Built: 2017 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial |
Building Construction Materials: Wood Frame, Clapboard ExteriorNot a New Construction |
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Price List Price: $2,750,000Price Per Sqft: $382 |
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MLS Status: Pending |
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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 |
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Listing Agent Listing ID: 5113588 |
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Building Area Building Area: 7205 Square Feet |
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Lot Area: 2.85 Acres |
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Special Conditions: Standard |
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BasementMls Number: 5113588Above 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
| Date | Event | Price |
|---|---|---|
Oct 28, 2026 Source: PrimeMLS #5113588 | Pending | $2,750,000 |
Oct 9, 2026 Source: PrimeMLS #5113588 | Listed For Sale | $2,750,000 |
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 |
| Year | Property tax | Tax assessment |
|---|---|---|
| 2024 | $27,148 | $1,199,100 |
Home facts updated by county records
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.
Market trends in Windham
Last updated October 2026
Avg. sale price
$909K
Sale-to-List Price
101.0%
Price per sq ft
$332
Available listings
38
5MoM
Sourced by Trulia Market Trends
Home Value
Trulia Estimate
$2.7MSince last month
Increased$51K (+1.9%)Since last year
Increased$181K (+7.2%)Since last sale
Increased$271K (+11.2%)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 +108% in the last 10 years
| Month | Estimated value |
|---|---|
2026 | |
| November 2026 | $2.7M |
| October 2026 | $2.69M |
| September 2026 | $2.65M |
| 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 |
|---|---|---|---|---|---|---|---|
0.12 | Single-Family Home | $1,690,000 | 05/15/26 | 5 | 4.5 | 4,653 | |
0.74 | Single-Family Home | $2,200,000 | 07/31/26 | 5 | 5.5 | 4,804 | |
0.77 | Single-Family Home | $1,730,000 | 09/30/26 | 6 | 4.5 | 8,225 | |
0.96 | Single-Family Home | $1,400,000 | 05/21/26 | 4 | 2.5 | 4,462 | |
0.90 | 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 | |
1.59 | Single-Family Home | $1,850,000 | 07/02/26 | 5 | 5.5 | 6,807 | |
1.44 | Single-Family Home | $2,000,000 | 03/20/26 | 4 | 3.5 | 4,854 | |
0.76 | Single-Family Home | $4,200,000 | 12/18/25 | 7 | 8.5 | 13,907 | |
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 |
|---|---|---|---|---|---|---|
0.06 | $1,940,000 | 5 | 4 | 5,015 | Off Market | |
0.07 | $1,864,100 | 4 | 3.5 | 4,093 | Off Market | |
0.07 | $2,815,800 | 4 | 4.5 | 6,553 | Off Market | |
0.07 | $2,922,200 | 7 | 5 | 7,500 | Off Market | |
0.08 | $1,626,200 | 4 | 4 | 3,918 | Off Market | |
0.08 | - | - | - | - | Off Market | |
0.08 | - | - | - | - | Off Market | |
0.08 | - | - | - | - | Off Market | |
0.08 | - | - | - | - | Off Market | |
0.09 | $3,286,100 | 7 | 6 | 9,825 | Off Market | |
0.10 | $2,004,500 | 4 | 5 | 4,293 | Off Market | |
0.10 | $1,752,400 | 4 | 3.5 | 4,019 | Off Market | |
0.10 | $1,496,300 | 4 | 4 | 4,283 | Off Market | |
0.12 | $1,693,300 | 4 | 4 | 4,294 | Off Market | |
0.12 | $1,690,000 | 5 | 4.5 | 4,653 | Recently Sold | |
0.12 | $2,763,000 | 4 | 5 | 6,155 | Off Market | |
0.13 | $1,353,200 | 4 | 3.5 | 4,347 | Off Market | |
0.14 | $2,631,700 | 5 | 5.5 | 6,696 | Off Market | |
0.15 | $1,617,400 | 4 | 2.5 | 4,156 | Off Market | |
0.15 | $1,779,400 | 4 | 4 | 4,170 | Off Market |
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Shannon DiPietro, DiPietro Group Real Estate, (603) 216-5086
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 2026-11-12 14:16:19 PST.
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.
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.
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Frequently asked questions about 20 Bennington Road
- What is the estimated monthly payment for 20 Bennington Road?Based on a $2,750,000 list price with 20% down at today's rates, the estimated monthly payment for 20 Bennington Road in Windham, NH is approximately $18,538 (about $15,301 principal & interest, $3,162 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
- How does the list price for 20 Bennington Road compare to homes in Windham?20 Bennington Road in Windham, NH is listed at $2,750,000, about 203% above the $909K median sale price in Windham.
- 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 homes for sale in Windham, NH.
- What are the closest schools to 20 Bennington Road?The closest schools to 20 Bennington Road in Windham, NH are Golden Brook Elementary School (Pre-K, rated 8/10), Windham Center School (Elementary, rated 9/10), Windham High School (rated 9/10).
- 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 laundry facilities.
20 Bennington Road, Windham, NH 03087 is a 4 bedroom, 6 bathroom, 7,205 sqft single-family home built in 2017. This property is currently available for sale and was listed by PrimeMLS on Oct 9, 2026. The MLS # for this home is MLS# 5113588.