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Jared McBride
REALTOR®
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39 Headlands Road, Winchester, NH 03470

$698,000
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Featured Listing Active
BEDS3 BATHS2 full SQUARE FEET1,364 MLS#5087379
STATUSActive PROPERTY TYPEResidential - Single Family SCHOOLWinchester

Listing Courtesy of: BHG Masiello Keene


Property Description

Step across the threshold and into a piece of history. A 1910 waterfront hidden treasure. Timeless architectural details and unparalleled views of Forest Lake make this home a rare blend of old world elegance and modern comfort amidst perennial gardens, stone sculptures and lush greenery A timeless stone fireplace with charming nooks & crannies in the spacious living room echoes the style of simpler times while offering an updated kitchen, two first floor bedrooms and a newer sun-filled master suite with barn-door entrance and lake views ... you'll feel apart from the busy world at this lakeside retreat. There is extended living space outdoors on a spacious and private wooden deck featuring a screened room overlooking the lake as well as a hot/cold outdoor shower! The stairway to your private dock has several landings. A small barn with loft offers plenty of storage or workshop space. There's also a garden shed for more storage. A perfect property for discerning buyers seeking a piece of history combined with unparalleled waterfront view and timeless elegance. Don't miss this opportunity!

39 Headlands Road | MLS# 5087379

This single family home located at 39 Headlands Road, Winchester, NH 03470 is currently listed for sale by BHG Masiello Keene, with an asking price of $698,000. This property was built in 1910 and has 3 bedrooms and 2 full baths with 1364 sq. ft. Headlands Road is located within the Winchester school district. Search Winchester real estate on jaredmcbride.masiellogrouprealestate.com today.

Property Features

Property Type: Residential - Single Family
Basement: Crawl Space, Dirt, Gravel, Partial, Walkout
Basement: Yes
Cooling: Central AC, Mini Split
Heating: Propane, Wood, Electric, Forced Air
Home Style: Cape, Historic Vintage, Modified
Lot Size: 0.36 Acres
Roof Type: Metal
Stories: 1.7
Taxes: $11,479
Year Built: 1910

Amenities

Ceiling Fan
Wood Fireplace
Laundry Hook-ups
Primary BR w/ BA
Natural Woodwork
Wood Stove Insert
1st Floor Laundry
Barn
Deck
Garden Space
Natural Shade
Outbuilding
Covered Porch
Screened Porch
Private Dock

Feature Descriptions

Accessibility: 1st Floor Bedroom, 1st Floor Full Bathroom, 1st Floor Low-Pile Carpet, 1st Floor Laundry
Appliances: Microwave, Gas Range, Refrigerator, Electric Water Heater, Owned Water Heater, Tank Water Heater
Baths 3/4: 1
Baths Full: 1
Color: Brown
Construction: Wood Frame, Vertical Siding, Wood Exterior, Wood Siding
Construction Status: Existing
Days on Site: 28
Driveway: Crushed Stone
Electric: 200+ Amp Service, Circuit Breaker(s)
Equipment: Battery Smoke Detector
Exterior: Wood Frame, Vertical Siding, Wood Exterior, Wood Sidi
Flood Zone: No
Flooring: Carpet, Hardwood, Tile
Foundation: Block, Pier/Column, Stone
Lot: Country Setting, Lake Frontage, Lake View, Landscaped, Mountain View, Sloping, View, Waterfront, Wooded
Nearby Bodies of Water: Forest Lake
Number of Rooms: 7
Parking: Driveway, Covered, Carport
Road Frontage: 104
Roads: Dead End, Public
Sewer: 1000 Gallon, Concrete, Holding Tank, Leach Field, Priv
Sq. Ft. Above Grade Finished: 1364
Sq. Ft. Total Finished: 1364
Total Stories: 1.75
Water: Public
Water Body Type: Lake
Water Frontage: 76
Water Rights: Exclusively Owned
Water View: Yes
Zoning: Lake

Local Schools

High School: Keene High School
Middle School: Winchester School
Elementary School: Winchester School
School District: Winchester

Listed By / Shown By

Listed By

Agency Name: BHG Masiello Keene

agent picture

Shown By

Agent Name: Jared McBride
Agent Phone:

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Estimated Payment

$ 2,713.61 per month $1,553.45 Principal & Interest $956.58 Property Tax $203.58 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided 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. Information on this site was last updated 06/04/2026. The listing information on this page last changed on 06/04/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Thu 06/04/2026 12:01:23 AM EST) or MLSPIN MLS (last updated Wed 06/03/2026 11:38:42 PM EST) or Prime MLS (last updated Wed 06/03/2026 11:33:45 PM EST) or MREIS (last updated Wed 06/03/2026 11:55:16 PM EST). Real estate listings held by brokerage firms other than Better Homes and Gardens Real Estate The Masiello Group may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

Listing data compilation and photo(s) copyright © 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display 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. Data Last Updated 2026-06-03 23:33:45

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Agency License Information: Better Homes and Gardens® and the Better Homes and Gardens Real Estate Logo are registered service marks owned by Meredith Corporation and licensed to Better Homes and Gardens Real Estate LLC. The Masiello Group Limited fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each franchise is independently owned and operated. Any services or products provided by independently owned and operated franchisees are not provided by, affiliated with or related to Better Homes and Gardens Real Estate LLC nor any of its affiliated companies.


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