#5045812, Vincent Dolan, Listing office: RE/MAX Town & Country

63 Headlands Rd Winchester, NH 03470
Property details
About 63 Headlands Rd
Rare expansive waterfront retreat on 2 private acres! Updated with modern comforts, this charming historic chalet retains its timeless appeal. Step into the grand living room with a cozy fireplace and soak in breathtaking views of the lake, mountains, and vibrant seasonal foliage. Dine or unwind in the sun-drenched four-season sunroom. The main floor also includes two comfortable bedrooms, a bright home office, and an updated full bath. A spacious loft provides tons of flexible space for guests or recreation. The partially finished basement offers added versatility with room for play, laundry, and a half bath. Outside, relax on the stone patio or explore the pine-wooded lot featuring your own private beach, day dock, and scenic walking trails. Just across the street is the detached 2-car garage for toys and vehicles. Some furniture is included making this a turnkey rental, 4-season getaway, or your lakefront dream home. 18 minutes to Keene, 25 minutes to Brattleboro, 2 hrs to Boston.
Highlights
Summary
- Partial Bathrooms: 1
- Full Bathrooms: 1
- Appliances: Dishwasher, Microwave, Electric Range, Refrigerator
- Basement: Yes
- Flooring Type: Wood
- Interior: Furnished, Natural Woodwork, Laundry - Basement
- Total Bedroom Count: 2
- Garage Space: 2 spaces
- Parking: Driveway, Parking Spaces 3 - 5, Detached
- Exterior: Day Dock, Patio, Porch - Heated
- Heating: Oil, Forced Air
- Cooling: None
- List Price: $720,000
- Price/SqFt: $353
- Annual Tax Amount: $8,126
- Tax Year: 2023
- Directions: Use GPS
- Year Built: 1916
- Stories: 2
- Living Area: 2,036 SqFt
- Lot Size: 2.03 Acres
- MLS Number: 5042562
- Office Name: Keller Williams Realty Metro-Keene
- Office Phone: (603) 352-0514
- Office Email: ecarrasquillo@kw.com
- Listing Agent: Ben Prentice
© Copyright 2025 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this site 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.
Housing Market Reports are calculated by Rocket Homes Real Estate, LLC and based on information from the MLS.
Data displayed may be a portion of, and not a complete set of all listings published in the MLS.
Last updated on: 6/13/2025, 5:45:34 AM Eastern. If you have any questions regarding the accuracy of this data, please contact us at help@rockethomes.com.
Get an agent. Get a mortgage. Save big.¹

$720,000
63 Headlands Rd
$8,550
closing credit¹
Sell your home with Rocket and save even more!
Seller rebate
0.5% sale price²
Price information
Property sales
Date | Event | Price |
---|---|---|
Aug 30, 1996 | Home Sold | $150,000 |
Tax history
Year | Assessment | Property Tax |
---|---|---|
2023 | $256,500 | $8,126 |
2022 | $256,500 | $7,362 |
2021 | $256,500 | $8,154 |
2020 | $256,500 | $7,380 |
2019 | $264,000 | $9,409 |
History based on county public records data.
Nearby schools
4
Cutler Elementary School
Public District 3-6
6.0 mi
•31 S Winchester St
2
Hinsdale Elementary School
Public District PK-5
6.9 mi
•12 School St
4
Northfield Elementary School
Public District PK-6
7.7 mi
•104 Main St
School ratings are a score out of 10, where 10 is the highest and 1 is the lowest.
Neighborhood
The neighbors living near this home have an average income of $48,194. The most common annual income of people living in Winchester, NH is between $35k-100k. Typical family type is single, no kids. The most common level of education of people living in this area is high school diploma.
Similar homes for sale
Frequently asked questions
About 63 Headlands Rd
The listing price of 63 Headlands Rd property is $720,000.
The property 63 Headlands Rd is a house located in Winchester, New Hampshire, 03470.
Active Listing: 63 Headlands Rd is For Sale (Active/New) which means the seller is accepting offers.
The nearby schools for 63 Headlands Rd are: Cutler Elementary School (GreatSchools Rating 4/10), Hinsdale Elementary School (GreatSchools Rating 2/10), Northfield Elementary School (GreatSchools Rating 4/10), Winchester School (GreatSchools Rating 2/10), Hinsdale Middle High School (GreatSchools Rating 3/10), Monadnock Regional Middle School (GreatSchools Rating 3/10), Hinsdale High School (GreatSchools Rating 4/10), Monadnock Regional High School (GreatSchools Rating 3/10), Pioneer Valley Regional School (GreatSchools Rating 5/10).
According to the records, the last property tax for 2023 is $8,126 (source: MLS/based on county public records data).
The last sale was on August 30, 1996 for $150,000 (source: MLS/tax record).
The property at 63 Headlands Rd has 2 bedrooms and 1 full and 1 half bathrooms.
The property 63 Headlands Rd is 2,036 SqFt (source: MLS/tax record).
The year of construction for 63 Headlands Rd is 1916.
This home is located at 63 Headlands Rd in Winchester, NH and zip code 03470. This 2,036 square foot home, which was built in 1916, sits on a 2.03 acre lot. Features: 2 bedrooms, 2 bathrooms. It has been listed on Rocket Homes since May 23, 2025 and is currently priced at $720,000.