20 Bennington Road

Active

$2,750,000

Est: $17,489/moGet pre-approved

4 beds6 baths7,205 sqft

20 Bennington Rd, Windham, NH 03087

Single FamilyProperty Type

2.85 acresLot Size

2017Year Built

$382/sq ftPrice per sq ft

3 carsParking Spaces

Description

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...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.

2 days on Market

Listed by: Shannon DiPietro • DiPietro Group Real Estate

Last updated: 10/09/2026 06:06 PM • Source: New England Real Estate Network, MLS#: 5113588

Location

Listing Courtesy of DiPietro Group Real Estate

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$17,489 per month

30 year fixed, 7.03% Interest

Principal and Interest

$14,681

Property Taxes

$2,808

HOA Dues

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Property Information for 20 Bennington Road

Property Details

Taxes: $33,691 / year
MLS Type: Residential / Single Family
County: Rockingham County
Zoning: RD

Building Information

Stories: 2
Year Built: 2017
Lot Size: 2.85 AC / 124,146 SF

Summary

Location and General Information

City: Windham
County: NH-Rockingham

Directions: GPS
Latitude: 42.786599000001004
Longitude: -71.326819000000000
Road Frontage: Yes
Seasonal: No
State: NH
Street Designation: Road
Map: 20
Zip Code: 03087

Taxes and HOA Information

Tax Year: 2025
Taxes TBD: No

Parking

Garage: Yes
Garage Capacity: 3.00

Driveway: Paved

Property

Lot Information

Block: D
Lot: 3022

Lot Features: Landscaped
Lot Size Acres: 2.85
Road Frontage Length: 172.0
Total Finished Area: 7205.0
Above Grade Finished Area: 5029.0
Above Grade Finished Area Source: Public Records
Above Grade Unfinished Area: 0.0
AboveGradeUnfinishedAreaSource: Public Records
Below Grade Finished Area: 2176.0
Below Grade Finished Area Source: Public Records
Below Grade Unfinished Area: 0.0
BelowGradeUnfinishedAreaSource: Public Records
Lot Size Square Feet: 124146.0
Total Area: 7205.0

Property and Assessments

Assessment Amount: $2,381,000
Assessment Year: 2025

Property Class: Residential
Property Type: Single Family
Property Condition: Existing
Flood Zone: Unknown
PreConstruction: No
Surveyed: No
Year Built: 2017
School District: Windham
High School: Windham High School
Middle/Jr School: Windham Middle School
Elementary School: Golden Brook Elementary School

Utilities

Electric: Circuit Breaker(s)
Sewer: Septic

Water Source: Drilled Well
Utilities: Cable
Internet: Cable Internet

Interior and Exterior Features

Exterior Features

Color: White
Construction Materials: Wood Frame, Clapboard Exterior

Roof: Architectural Shingle

Interior Features

Appliances: ENERGY STAR Qual Dishwshr, Disposal, ENERGY STAR Qual Dryer, Range Hood, Freezer, Microwave, Double Oven, Gas Range, Refrigerator, ENERGY STAR Qual Washer, Gas Water Heater, Exhaust Fan
Basement: Yes

Basement Access Type: Walkout
Basement Description: Climate Controlled, Daylight, Finished, Full, Storage Space, Walkout, Interior Access, Exterior Access, Basement Stairs
Flooring: Carpet, Ceramic Tile, Hardwood
Heating: Propane, Forced Air, Multi Zone
Cooling: Central AC
Total Stories: 2
Rooms Total: 10
Bathrooms Full: 2
Bathrooms Half: 1
Bathrooms One Quarter: 0
Bathrooms Three Quarter: 3
Bedrooms Total: 4
Bathrooms Total: 6

Property History for 20 Bennington Road

Date	Event & Source	Price	Appreciation
Oct 8, 2026	Listed (Active) New England Real Estate Network #5113588	$2,750,000	—
Aug 5, 2024	Sold (Public Record) Public Record #1538347825	$2,430,000	—
Aug 5, 2024	Sold New England Real Estate Network #4998946	$2,430,000	—
Jun 11, 2024	Pending New England Real Estate Network #4998946		—
Jun 5, 2024	Listed (Active) New England Real Estate Network #4998946	$2,495,000	—
Aug 30, 2017	Sold New England Real Estate Network #4637894	$1,248,527	—
Aug 30, 2017	Pending New England Real Estate Network #4637894		—
May 31, 2017	Price Change New England Real Estate Network #4637894	$1,250,527	—
May 31, 2017	Listed (Active) New England Real Estate Network #4637894	$1,050,527	—

Date	Event & Source	Price
10/08/2026	Listed (Active) New England Real Estate Network #5113588	$2,750,000
08/05/2024	Sold (Public Record) Public Record #1538347825	$2,430,000
08/05/2024	Sold New England Real Estate Network #4998946	$2,430,000
06/11/2024	Pending New England Real Estate Network #4998946	—
06/05/2024	Listed (Active) New England Real Estate Network #4998946	$2,495,000
08/30/2017	Sold New England Real Estate Network #4637894	$1,248,527
08/30/2017	Pending New England Real Estate Network #4637894	—
05/31/2017	Price Change New England Real Estate Network #4637894	$1,250,527
05/31/2017	Listed (Active) New England Real Estate Network #4637894	$1,050,527

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public records

20 Bennington Road

Beds

Baths

5.5

Total Finished SqFt

5,341 SqFt

Above Grade Finished SqFt

5,341 SqFt

Unfinished Basement SqFt

593 SqFt

Stories

Schools near 20 Bennington Road

This home is within Windham School District.


Rating	School	Type	Grades	Distance
8/10	Golden Brook Elementary School	Public - Serves this home	PK to 4	0.9 mi
9/10	Windham Center School	Public - Serves this home	5 to 6	1.5 mi
9/10	Windham Middle School	Public - Serves this home	7 to 8	0.7 mi
9/10	Windham High School	Public - Serves this home	9 to 12	0.7 mi


Rating	School	Distance
8/10	Golden Brook Elementary School PublicPK to 4 Serves this home	0.9 mi
9/10	Windham Center School Public5 to 6 Serves this home	1.5 mi
9/10	Windham Middle School Public7 to 8 Serves this home	0.7 mi
9/10	Windham High School Public9 to 12 Serves this home	0.7 mi

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 20 Bennington Road, Windham, NH 03087

20 Bennington Road is a single family home for sale in Windham, NH 03087. This property was listed for sale on October 8, 2026 by DiPietro Group Real Estate, it's currently listed at $2,750,000. It has been on the market for a total of 2 days and was last sold on August 5, 2024. This listing's school district is Windham School District. Nearby schools include Golden Brook Elementary School, Windham Center School and Windham Middle School. 20 Bennington Road is a 4-bed, 6-bath, 7,205 sqft single family home built in 2017.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity.