NEW 18 HRS AGO

Listed by Shannon DiPietro • DiPietro Group Real Estate.

For sale

$2,750,000

Est. $18,557/mo —

•

7,205

sq ft

20 Bennington Rd, Windham, NH 03087

About this home

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.

Single-familyProperty Type

2017Year Built

2.85 acresLot Size

$382Price/Sq.Ft.

3 car garageParking

Listed by Shannon DiPietro • DiPietro Group Real Estate

Listing updated: Oct 9, 2026 at 09:06pm

Redfin checked: 2 minutes ago

•Source:PrimeMLS #5113588

Payment calculator

$18,557 per month

Principal and interest$15,383

Property taxes

$2,808

HOA dues

Home insurance

$367

Utilities

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Open houses

No upcoming open houses.

Nearby open houses (10)

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OPEN SAT, 2PM TO 3:30PM
$499,900
3 beds2 baths1,502 sq ft
11 Chestnut Hill Rd, Londonderry, NH 03053
OPEN SUN, 12PM TO 2PM
$369,900
2 beds1 bath855 sq ft
20 Mills Dr, Dracut, MA 01826
OPEN OCT 17, 11AM TO 1PM
$759,900
2 beds2.5 baths2,119 sq ft
6 Chadwick Cir, Windham, NH 03087

Around this home

Schools

K - 12
Preschool & daycare

Golden Brook Elementary School

Public PreK-4 • Assigned • 0.9mi

8/10

Windham Middle School

Public 7-8 • Assigned • 0.9mi

9/10

Windham High School

Public 9-12 • Assigned • 0.6mi

9/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Offer insights

20 Bennington Rd · $2,750,000

Strong offer

$2.82M and above

75% chance or better to win

Why $2.82M+ is a strong offer

DAYS ON MARKET

The average home goes pending in 42 days.

SALE-TO-LIST

Most homes are selling 1% above list price.

About offer insights

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Dining

Interior features
Finished, climate-controlled basement with daylight, storage space, walkout access, and interior and exterior entrances

Bathrooms
2 full bathrooms
3 three-quarter bathrooms
1 half bathroom

Kitchen
Dishwasher, disposal, exhaust hood, freezer, microwave, double oven, gas range, refrigerator

Laundry & utility
Energy Star washer and dryer
Gas water heater

Flooring
Ceramic tile, hardwood

Heating & cooling
Propane forced-air heating with multiple zones
Central air conditioning

Sale and tax history for 20 Bennington Rd

Sale History
Tax History

Date

Event

Price

PrimeMLS #5113588

Oct 8, 2026

Listed

$2,750,000

$382/sq ft

PrimeMLS #4998946

Aug 5, 2024

Sold

$2,430,000

$337/sq ft

Jun 12, 2024

Pending

—

Jun 5, 2024

Listed

$2,495,000

$346/sq ft

+32

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.

PrimeMLS #4637894

Aug 30, 2017

Sold

$1,248,527

$173/sq ft

Jun 7, 2017

Contingent

—

Jun 2, 2017

Price Changed

$1,250,527

$174/sq ft

Jun 1, 2017

Listed

$1,050,527

$146/sq ft

Year

Property tax

Land + Additions

Assessment*

2024

$27,148 (+5.8%)

$290,500 + $908,600

$1,199,100

2023

$25,661 (+8.3%)

$290,500 + $908,600

$1,199,100

2022

$23,694 (+5.7%)

$290,500 + $908,600

$1,199,100

2021

$22,415 (−2.7%)

$290,500 + $913,300

$1,203,800

2020

$23,029 (+5.3%)

$290,500 + $913,300

$1,203,800

2019

$21,864 (−3.2%)

$237,500 + $732,100

$969,600

2018

$22,582 (+342.7%)

$237,500 + $732,100

$969,600

2017

$5,101 (−1.6%)

$237,500 + $15,000

$252,500

2016

$5,182 (+0.4%)

$237,500

2015

$5,159

$237,500

Public record

Beds

Baths

4.5

Stories

Lot width

—

Lot depth

—

Lot size

2.85 Acres

Year renovated

2017

Finished Sq. Ft.

5,341

Unfinished Sq. Ft.

—

Total Sq. Ft.

5,341

Year built

2017

Style

Single Family Residential

County

Rockingham County

APN

972978

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on May 15, 2026.

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

3/10 Heat Factor

7 days above 95° expected this year, 15 days in 30 years

6/10 Wind Factor

27% chance of strong winds in next 30 years

2/10 Air Factor

2 unhealthy days expected this year, 2 days in 30 years

Provided by First Street

Historical weather

Windham, NH • 03087

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 9.1 hours in June and 4.4 hours in December, placing it below the U.S. average for solar exposure.

9.1 hrs

4.4 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 20 Bennington Rd

$2,738,878

$11K under list price of $2.75M

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $1.0M to $2.5M.

SOLD MAY 15, 2026
$1,690,000 Last sold price
5 beds4.5 baths4,653 sq ft
36 Burnham Rd, Windham, NH 03087
$19/sq ft
smaller lot
3 years older
SOLD AUG 3, 2026
$1,087,000 Last sold price
4 beds2.5 baths3,559 sq ft
7 Wilson Rd, Windham, NH 03087
$77/sq ft
larger lot
25 years older
SOLD JUN 4, 2026
$1,050,000 Last sold price
3 beds2.5 baths3,224 sq ft
14 Buckhide Rd, Windham, NH 03087
$56/sq ft
smaller lot
10 years older
SOLD AUG 26, 2026
$2,500,000 Last sold price
5 beds3 baths3,219 sq ft
29-31 Walkeys Rd, Windham, NH 03087
$395/sq ft
smaller lot
57 years older
SOLD JUL 23, 2026
$1,299,000 Last sold price
4 beds3.5 baths3,743 sq ft
20 Cobbetts Pond Rd, Windham, NH 03087
$35/sq ft
larger lot
44 years older
SOLD MAY 27, 2026
$1,015,000 Last sold price
4 beds2.5 baths2,998 sq ft
10 Harmony Ln, Pelham, NH 03076
$43/sq ft
smaller lot
3 years older

Rental earnings

Est. $4,279 per month, based on comparable rentals

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(603) 288-1213

Early Access listings

EARLY ACCESSCOMPASS COMING SOON

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11 Suffolk Dr #2, Concord, NH 03303

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New listings for sale in 03087

OPEN OCT 17, 11AM TO 1PM

$759,900

2 beds2.5 baths2,119 sq ft

6 Chadwick Cir, Windham, NH 03087

NEW 18 HRS AGO

$2,750,000

4 beds5.5 baths7,205 sq ft

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OPEN SAT, 2PM TO 4PM

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NEW 23 HRS AGO

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REDFIN OPEN TODAY, 3:30PM TO 5:30PM3D WALKTHROUGH

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3 Misty Meadow Rd, Windham, NH 03087

$1,000,000

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7 Porcupine Rd, Windham, NH 03087

OPEN SAT, 11AM TO 1PM

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3 beds1 bath1,761 sq ft

22 Cobbetts Pond Rd, Windham, NH 03087

$469,900

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21 Braemar Rd, Windham, NH 03087

$1,725,000

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Details provided by PrimeMLS and may not match the public record. Learn more.

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About this home

Payment calculator

Affordability tools

See this home in person

Nearby open houses (10)

Around this home

Schools

Lifestyle

Offer insights

Property details

Sale and tax history for 20 Bennington Rd

Public record

Climate risks

Historical weather

Sun exposure

Redfin Estimate for 20 Bennington Rd

Early Access listings

Nearby similar homes

New listings for sale in 03087

More real estate resources