5 Sherwood Road Windham, NH $ 1,599,000
5 Sherwood Road
$ 1,599,000
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5 Sherwood Road

Windham, NH, 03087
$ 1,599,000
Bedrooms4 Baths3.1 Sq 5,112

Monthly Estimate*

$ 10,096

Listed by Shannon DiPietro, DiPietro Group Real Estate, 603-216-5086, sdipietro@dipietrogroupre.com
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Single Family Home for sale in Windham, NH

for $1,599,000 with 4 bedrooms and 3 full baths, 1 half bath. This 5,112 square foot home was built in 1999 on a lot size of 3.79.

Timeless elegance meets modern luxury in this exceptional custom Colonial, privately set on 3.5 meticulously landscaped acres. Offering four spacious bedrooms and a beautifully designed walk-out lower-level in-law suite, this remarkable home delivers the perfect blend of sophistication, comfort, and versatility. From the moment you enter the grand two-story foyer, you'll appreciate the impeccable craftsmanship, classic architecture, and custom millwork found throughout. The thoughtfully designed floor plan features a private home office, an elegant formal dining room ideal for entertaining, and a warm, inviting family room centered around a stunning fireplace. At the heart of the home, the expansive kitchen opens seamlessly to the living spaces, creating the perfect gathering place for family and friends. Just beyond, a breathtaking sunroom overlooks the private backyard, filling the home with natural light and providing direct access to the expansive composite deck. Privately situated at the opposite end of the home, the first-floor media room is an entertainer's dream, showcasing custom millwork, a beautifully crafted built-in bar, and the perfect setting for movie nights, game days, or hosting guests. The luxurious primary suite serves as a true retreat with a spa-inspired bath, while the additional bedrooms are all exceptionally spacious. The walk-out lower level offers a complete in-law suite with its own living space, providing exceptional flexibility for multigenerational living, extended family, guests, or an au pair. Step outside to your own private resort where the expansive composite deck overlooks a spectacular gunite inground pool, all surrounded by professionally designed landscaping that creates an unmatched sense of privacy across 3.5 acres. A classic farmer's porch welcomes you home, completing this extraordinary property where timeless architecture, luxurious finishes, and seamless indoor-outdoor living come together.

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Single Family Active

Price

$ 1,599,000

Bedrooms

4

Full Bath

3

Half Bath

1

Property Type

Single Family

Taxes

$ 0

Style

Colonial

Lot Size

3.79

Year Built

1999

Town/City

Windham

County/Region

Rockingham

MLS | Web ID

5099575

Features
Interior
Basement Description Finished Insulated Interior Stairs Walkout Interior Access Exterior Access
Interior Amenities Central Vacuum Bar Blinds Ceiling Fan Dining Area 1 Fireplace Hot Tub In-Law Suite Kitchen Island LED Lighting Primary BR w/ BA Natural Light Soaking Tub Surround Sound Wiring Walk-in Closet Whirlpoo
Basement Yes
Flooring Bamboo Carpet Ceramic Tile Hardwood Laminate
Beds 4
Total Rooms 10
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General
Road Frontage Yes
Sewer 1500+ Gallon Leach Field On-Site Septic Exists Private
Heating Propane Oil Solar Wood Electric Forced Air Wood Stove Mini Split
Cooling Central AC Multi Zone Wall AC Units Mini Split
Utilities Cable Propane Other
Roof Architectural Shingle Asphalt Shingle
Appliances Down Draft Cooktop Gas Cooktop Microwave Wall Oven Refrigerator Washer Water Heater off Boiler Oil Water Heater Tank Water Heater Gas Dryer Vented Exhaust Fan Water Heater
Garage Yes
Flood Zone Unknown
Zoning RD
3/4 Baths 1
Full Baths 2
Half Baths 1
Bathrooms 4
Year Built 1999
Electric 200+ Amp Service Circuit Breaker(s) Generator Off Grid Net Meter Energy Storage Device
Style Colonial
Stories Count 2
Construction Status Existing
Type Single Family
Block A
Assessment Amount 1429000
Accessibility Features 1st Floor 1/2 Bathroom 1st Floor Hrd Surfce Flr 1st Floor Laundry
Auction No
Tax Year 2025
Status Detail 0
Covenants Unknown
Construction Materials Wood Frame Clapboard Exterior
Directions GPS
City Windham
Other Equipment Air Conditioner CO Detector Irrigation System Radon Mitigation HW/Batt Smoke Detector Wood Stove Standby Generator
Seasonal No
DOM 2
Price Per Sq Ft Total AG 405.02
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Exterior
Lot Features Landscaped Wooded
Exterior Amenities Deck Dog Fence Partial Fence Hot Tub Patio In-Ground Pool Porch Storage Window Screens Double Pane Window(s)
Driveway Paved
Lot Size Area 3.79
Water Source Drilled Well On-Site Well Exists Private Purifier/Soft
Parking Features Assigned Driveway Garage
Garage Capacity 3
Foundation Concrete
Lot 235
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* Excluded Features
List By
Shannon DiPietro

Listing Agent

Dipietro Group Real Estate

Broker

(603) 216-5086

Phone

sdipietro@dipietrogroupre.com

Email

Affordability Calculator

$10,096
Per Month
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Monthly Principal & Interest
$10,096
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Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
451920 Elementary School
452237 Middle School
Unknown High School High School
Pricing History
DatePricePrice ChangeDescription
7/13/2026$1,599,000 Listed Price

Map


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5 Sherwood Road, Windham, NH, 03087 is a Single Family Home for sale at $1,599,000 with 5,112 sqft and a lot size of 3.79. 5 Sherwood Road has 4 bedrooms, 3.1 baths, and was built in 1999. The property's zip code is 03087 which is in Windham, NH