27 Headlands Rd

Winchester, NH 03470

$725,000
Price
2
Beds
1,351 Sq. Ft.
$537 / Sq. Ft.
1,351
Sq. Ft.
$537
per Sq. Ft.

Description

Stunning Waterfront! Like new Cape style post and beam beauty with direct waterfront on Forest Lake. Gorgeous views from every window. Modern Kitchen with stainless appliances and center island. Cozy Living Room with gas Fireplace. The downstairs living area contains a Family Room, Kitchen, Bedroom and Bathroom. This is a perfect year-round retreat or possible short term rental. Also being offered as part of a portfolio of short-term rental properties.Stunning Waterfront! Like new Cape style post and beam beauty with direct waterfront on Forest Lake. Gorgeous views from every window. Modern Kitchen with stainless appliances and center island. Cozy Living Room with gas Fireplace. The downstairs living area contains a Family Room, Kitchen, Bedroom and Bathroom. This is a perfect year-round retreat or possible short term rental. Also being offered as part of a portfolio of short-term rental properties.
  1. Listed by Vincent Dolan • RE/MAX Town & Country
  2. Listed by Alejandra Patton Spruill • RE/MAX Town & Country

Property Details for 27 Headlands Road

Water Body Type
Lake
Waterfront Property
Yes
Zoning
Forest Lake District
LISTING UPDATED: 11/19/2025 04:26 PM

Property Details for 27 Headlands Road

StatusActive
MLS #5045812
Days on Market188
Taxes$9,340 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family
Year Built1992
Lot Size0.16 AC / 6,969 SF
CountyCheshire County

Location

Listing Courtesy of RE/MAX Town & Country
Add your commute

Building Information for 27 Headlands Road

Stories1Year Built1992Building Size-Lot Size0.16 AC / 6,969 SF

Payment Calculator

$4,361 per month

30 year fixed, 6.28% Interest

Principal and Interest

$3,582

Property Taxes

$778

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 27 Headlands Road

Summary
Location and General Information
  • City: Winchester
  • County: NH-Cheshire
  • Latitude: 42.788603126483238
  • Longitude: -72.362255457672134
  • Road Frontage: Yes
  • Seasonal: No
  • State: NH
  • Street Designation: Road
  • Map: 33
  • Zip Code: 03470
Taxes and HOA Information
  • Tax Year: 2023
  • Taxes TBD: No
Parking
  • Garage: No
  • Driveway: Gravel
Property
Lot Information
  • Block: 1
  • Lot: 16
  • Lot Features: Lake Frontage, Lake View, Sloping, Waterfront
  • Lot Size Acres: 0.16
  • Road Frontage Length: 71.0
  • Water Body Name: Forest Lake
  • Waterfront Property Rights: Exclusively Owned
Property and Assessments
  • Property Class: Residential
  • Property Type: Single Family
  • Construction Status: Existing
  • Flood Zone: No
  • PreConstruction: No
  • Surveyed: Unknown
  • Water Body Restrictions: Unknown
  • Year Built: 1992
Utilities
  • Electric: 100 Amp Service, Circuit Breaker(s)
  • Sewer: Leach Field On-Site, Private, Septic
  • Water Source: Public
  • Utilities: Cable Available, Propane, Underground Gas
  • Internet: High Speed Intrnt Avail
Interior and Exterior Features
Exterior Features
  • Association Amenities: Beach Access, Beach Rights
  • Construction Materials: Post and Beam, Wood Frame
  • Roof: Architectural Shingle
Interior Features
  • Appliances: Dishwasher, Microwave, Mini Fridge, Gas Range, Refrigerator
  • Basement: Yes
  • Basement Access Type: Interior
  • Basement Description: Finished, Interior Stairs, Walkout
  • Rooms: Level 1: Level 1: Dining Room, Level 1: Kitchen, Level 1: Living Room
  • Rooms: Level 2: Level 2: Bedroom
  • Rooms: Level B: Level B: Bedroom, Level B: Family Room, Level B: Kitchen
  • Flooring: Carpet, Softwood, Vinyl
  • Heating: Baseboard
  • Cooling: Mini Split
  • Total Stories: 1.5
Room Information
Room 1
  • Room Level: 1
  • Room Type: Kitchen
Room 2
  • Room Level: 1
  • Room Type: Dining Room
Room 3
  • Room Level: 1
  • Room Type: Living Room
Room 4
  • Room Level: 2
  • Room Type: Bedroom
Room 5
  • Room Level: Basement
  • Room Type: Family Room
Room 6
  • Room Level: Basement
  • Room Type: Bedroom
Room 7
  • Room Level: Basement
  • Room Type: Kitchen

Property History for 27 Headlands Road

DateEvent & SourcePriceAppreciation
Jun 10, 2025

Listed (Active)

New England Real Estate Network #5045812

$735,000—
Dec 22, 2022

Sold (Public Record)

Public Record #1503181636

$650,000

+27.7% / yr

Dec 22, 2022

Sold

New England Real Estate Network #4911086

$650,000—
Dec 20, 2022

Pending

New England Real Estate Network #4911086

—
Sep 6, 2022

Active Under Contract

New England Real Estate Network #4911086

—
May 20, 2022

Listed (Active)

New England Real Estate Network #4911086

$679,000—
May 15, 2019

Sold

New England Real Estate Network #4742566

$268,391—
May 11, 2019

Sold (Public Record)

Public Record #647181793

$268,400

+0.4% / yr

Apr 9, 2019

Pending

New England Real Estate Network #4742566

—
Mar 29, 2019

Listed (Active)

New England Real Estate Network #4742566

$287,000—
Dec 17, 2018

Expired

New England Real Estate Network #4696476

—
May 30, 2018

Listed (Active)

New England Real Estate Network #4696476

$295,000—
Dec 16, 2017

Expired

New England Real Estate Network #4628399

—
Apr 19, 2017

Listed (Active)

New England Real Estate Network #4628399

$299,000—
Jan 1, 2017

Expired

New England Real Estate Network #4478531

—
Mar 25, 2016

Listed (Active)

New England Real Estate Network #4478531

$299,950—
Nov 30, 2015

Expired

New England Real Estate Network #4418351

—
Apr 30, 2015

Listed (Active)

New England Real Estate Network #4418351

$311,000—
Oct 31, 2014

Expired

New England Real Estate Network #4352899

—
May 1, 2014

Listed (Active)

New England Real Estate Network #4352899

$319,000—
Jan 31, 2005

Sold (Public Record)

Public Record #285060462

$255,000

+18.7% / yr

Jan 31, 2005

Sold

New England Real Estate Network #158516

$255,000—
Dec 26, 2004

Pending

New England Real Estate Network #158516

—
Jul 9, 2004

Listed (Active)

New England Real Estate Network #158516

$269,000—
Jan 23, 2001

Sold

New England Real Estate Network #790010

$127,500—
Jan 22, 2001

Pending

New England Real Estate Network #790010

—
Jan 20, 2001

Listed (Active)

New England Real Estate Network #790010

$139,900—
Jan 18, 2001

Sold (Public Record)

Public Record #285059902

$127,500—
DateEvent & SourcePrice
06/10/2025

Listed (Active)

New England Real Estate Network #5045812

$735,000
12/22/2022

Sold (Public Record)

Public Record #1503181636

$650,000

+27.7% / yr

12/22/2022

Sold

New England Real Estate Network #4911086

$650,000
12/20/2022

Pending

New England Real Estate Network #4911086

—
09/06/2022

Active Under Contract

New England Real Estate Network #4911086

—
05/20/2022

Listed (Active)

New England Real Estate Network #4911086

$679,000
05/15/2019

Sold

New England Real Estate Network #4742566

$268,391
05/11/2019

Sold (Public Record)

Public Record #647181793

$268,400

+0.4% / yr

04/09/2019

Pending

New England Real Estate Network #4742566

—
03/29/2019

Listed (Active)

New England Real Estate Network #4742566

$287,000
12/17/2018

Expired

New England Real Estate Network #4696476

—
05/30/2018

Listed (Active)

New England Real Estate Network #4696476

$295,000
12/16/2017

Expired

New England Real Estate Network #4628399

—
04/19/2017

Listed (Active)

New England Real Estate Network #4628399

$299,000
01/01/2017

Expired

New England Real Estate Network #4478531

—
03/25/2016

Listed (Active)

New England Real Estate Network #4478531

$299,950
11/30/2015

Expired

New England Real Estate Network #4418351

—
04/30/2015

Listed (Active)

New England Real Estate Network #4418351

$311,000
10/31/2014

Expired

New England Real Estate Network #4352899

—
05/01/2014

Listed (Active)

New England Real Estate Network #4352899

$319,000
01/31/2005

Sold (Public Record)

Public Record #285060462

$255,000

+18.7% / yr

01/31/2005

Sold

New England Real Estate Network #158516

$255,000
12/26/2004

Pending

New England Real Estate Network #158516

—
07/09/2004

Listed (Active)

New England Real Estate Network #158516

$269,000
01/23/2001

Sold

New England Real Estate Network #790010

$127,500
01/22/2001

Pending

New England Real Estate Network #790010

—
01/20/2001

Listed (Active)

New England Real Estate Network #790010

$139,900
01/18/2001

Sold (Public Record)

Public Record #285059902

$127,500

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 27 Headlands Road

Taxable ValueLand$129,100Additions$165,700Total$294,800
Tax Record2024$8,623 ($719 / month)
Home Facts
Beds2Baths1.5Total Finished SqFt1,387 SqFtAbove Grade Finished SqFt1,387 SqFtStories2Lot Size6,970 SqFtStyleSingle Family ResidenceYear Built1992ZoningLAKEFOCountyCHESHIREAPNWNCH M:00033 B:000016 L:000000

Schools near 27 Headlands Road

This home is within Winchester School District.
Rating
School
Type
Grades
Distance
Winchester School
Public - PK to 8
Keene High School
Public - 9 to 12
Rating
School
Distance
Winchester School
PublicPK to 8

Keene High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 27 Headlands Road, Winchester, NH 03470

27 Headlands Road is a single family home for sale in Winchester, NH 03470. This property was listed for sale on June 10, 2025 by RE/MAX Town & Country, it's currently listed at $725,000. It has been on the market for a total of 188 days and was last sold on December 22, 2022. This listing's school districts are Winchester School District, Keene School District. Nearby schools include Winchester School and Keene High School. 27 Headlands Road is a 2-bed, 2-bath, 1,351 sqft single family home built in 1992.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of RE/MAX Town & Country

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. Data last updated 12/15/2025 07:23 PM