Price Reduced46
$1,500,000
4 bd · 4 ba · 5,112 sqft
5 Sherwood Road, Windham, NH
Shannon DiPietro · DiPietro Group Real Estate · on 2 MLSs
Est. $9,493/mo$372/sqft · 204 days on Realty
4
Beds
4
Baths
4,029
Sqft
2019
Built
Stunning 2019 home in sought-after Windham NH in a 32 lot high end subdivision in highly desired Windham NH for its excellent school systems and easy access for commuting between NH and Massachusetts. This home features five bedrooms and three and a half bathrooms offering a versatile layout ideal for everyday living and entertaining. The property includes a pool, patio, firepit, covered deck, and a heated oversize 4-car garage with a workshop that features 14-foot ceilings- perfect for accommodating car lifts, extra storage, or easily convert one bay to a golf simulator or pool table space. The home offers two primary bedroom options, each with a full en suite bathroom. The one on the first floor includes private access to outdoor living areas; or the second on the upper floor is nearer the other bedrooms. With three additional bedrooms, the home provides flexibility for a variety of living arrangements. The three and a half bathrooms include modern fixtures and finishes. A full footprint unfinished walk-out basement with lots of natural light gives the opportunity for additional expansion if desired. The expansive indoor and outdoor living spaces are well suited for entertaining. The patio, wrap-around farmers porch and covered rear deck create seamless transitions between the interior and exterior of the home. The four-car garage is ideal for car enthusiasts or hobbyists needing secure, heated indoor workspace and storage for boats or toys. A thoughtful layout, with high quality construction, that has been meticulously maintained makes this home an opportunity for comfortable and functional living.
Listing agent
Christine Koutrobis
Courtesy of Coldwell Banker Realty Andover MA
NEREN · Listing 5078716
NERENCourtesy of Coldwell Banker Realty Andover MA
Listing agent: Christine Koutrobis · Listing 5078716
$299,800
Estimated monthly payment
$9,493/mo
Loan amount $1,199,200. Estimate only — your actual rate and payment depend on credit, location, and lender.
2025 roll
Within 2 miles of this home: 14 restaurants and cafés, 1 grocery store, and 7 parks and green spaces.
Place data from OpenStreetMap.
Capri Pizza and Friendly Red's Tavern
Haverhill Road
Capri Pizza
Friendly Red's Tavern
Kendall Pond Pizza
Mammoth Road
Dunkin' Donuts
Indian Rock Road
Kumo Sushi
TJ's Roast Beef & Pizza
Indian Rock Road
Klemm's Bakery
Indian Rock Road, Route 111
Shaw's
Indian Rock Road
Nashua Road Fields
Foster's Pond Natural Area
Foster's Pond
Clyde Pond
Windham Town Land
Campbell Farm
Gage Conservation Lands
NEREN
MLS Property Information Network (MLS PIN)
PrimeMLSThis content last refreshed on 2026-09-29 03:03:53 UTC. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.
Price Reduced46
$1,500,000
4 bd · 4 ba · 5,112 sqft
5 Sherwood Road, Windham, NH
Shannon DiPietro · DiPietro Group Real Estate · on 2 MLSs
52$1,600,000
3 bd · 3 ba · 4,001 sqft
6 Rosewood Street, Windham, NH
Jill A Jablonski · McGinn & Associates Realty, LLC
Price Reduced31$1,089,000
4 bd · 3 ba · 3,707 sqft
5 Bedros St, Windham, NH
on 3 MLSs
Price Reduced51$1,090,000
4 bd · 3 ba · 3,900 sqft
1 Telo Road, Windham, NH
Debra Forte · Century 21 North East
Price Reduced59$1,195,000
4 bd · 3 ba · 2,689 sqft
13 Sunridge Road, Windham, NH
Chelsey Holston · Keller Williams Gateway Realty/Salem
42$1,175,000
4 bd · 3 ba · 3,212 sqft
18 Longmeadow Road, Windham, NH
Ashley A Ciaraldi · BHHS Verani Londonderry





School ratings (A+ to F) from HJN community data.
Windham High School
9-12 · Regular · Windham School District
945 students · 12.8:1 student–teacher
Windham Center School
5-6 · Regular · Windham School District
426 students · 14.7:1 student–teacher
South Elementary School
1-5 · Regular · Londonderry School District
412 students · 9.9:1 student–teacher
Windham Middle School
7-8 · Regular · Windham School District
414 students · 12.2:1 student–teacher
Golden Brook Elementary School
PK-4 · Regular · Windham School District
1,113 students · 17.9:1 student–teacher
Over the Rainbow Preschool
PK-KG · Early Childhood Program/Child Care Center
61 students · 61.0:1 student–teacher
Windham Academy Public Charter School
KG-8 · Regular · Windham Academy Public Charter School
410 students · 15.8:1 student–teacher
Hijk,Inc Dab Early Start Learning Academy
PK-KG · Early Childhood Program/Child Care Center
11 students · 11.0:1 student–teacher