OFF MARKET

Listed by Steve Filipi • Blais & Associates, Realtors. Bought with RE/MAX Town & Country.

Off market dec 2022 for $650K

$630,785

•

1,470

sq ft

27 Headlands Rd, Winchester, NH 03470

About this home

Westerly exposure and the giant windows on all 3 levels of this country waterfront home offer unmatched views and sunsets over Forest Lake! This post and beam style waterfront home has been meticulously maintained and owners have recently installed new windows, pvc trim, and high-end vinyl shake siding for a maintenance free beautiful exterior. The new kitchen is amazing with stainless steel appliances, solid surface countertops and island space with soaring cathedral ceilings. Having a large get together? With the 2nd kitchenette in the finished walk out basement you will have no problems! The upper and lower decks have been rebuilt for a worry-free outdoor gathering space. Oil boiler has been replaced with 2 Mini splits for economical and comfortable heating and cooling year-round plus a new gas fireplace to cozy up to on those cool nights. The attached shed is great for storing all of your water fun gear out of the weather. Bring your boat and pull up to the dock and enjoy fishing and water skiing. Whether you need a place to get away from it all or want to go on a permanent vacation this awesome home checks all the boxes! Property conveys partially furnished. Listing agent is related to the seller.

Single-familyProperty Type

1992Year Built

6,969 sq ftLot Size

$429Est. Price/Sq.Ft.

Listed by Steve Filipi • Blais & Associates, Realtors

Bought with Vincent Dolan • RE/MAX Town & Country

Redfin checked: a minute ago

•Source:PrimeMLS #4911086

Redfin Estimate

$630,785

$19K since sold in December 2022$49K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 96% higher than the average sale price ($322K) of 6 comparable homes.

SOLD FEB 27, 2026
$295,000
A
3 beds2 baths1,344 sq ft
19 Toofs Dr, Winchester, NH 03470
SOLD SEP 16, 2026
$315,000
B
2 beds1 bath960 sq ft
229 Back Ashuelot Rd, Winchester, NH 03470
SOLD AUG 27, 2026
$365,000
C
3 beds1.5 baths1,192 sq ft
55 Verry Brook Rd, Winchester, NH 03470
SOLD SEP 24, 2026
$289,900
D
3 beds1 bath1,118 sq ft
12 Rabbit Hollow Rd, Winchester, NH 03470
SOLD JUN 18, 2026
$361,000
E
3 beds2 baths1,546 sq ft
12 Pudding Hill Rd, Winchester, NH 03470
SOLD OCT 8, 2026
$305,000
F
3 beds1.5 baths1,352 sq ft
71 Oliver Hill Rd, Swanzey, NH 03446

Claim this home to receive a free report every month with insights on the changing estimate.

Earn from this home

Sell

$110,493

Est. take-home

List your home with Redfin and save $6,308

Rent

$2,352/mo

Redfin rental estimate

List your home for rent

Market trends in 03470, NH

Last updated October 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-list price

98.8%

0.9% MoM

Median sale price

$371K

$6K MoM

Avg. days on market

54d

1 days MoM

Recently sold homes

3 MoM

New listings for sale

$699,000
8 beds4 baths3,515 sq ft
37 Michigan St, Winchester, NH 03470
$499,900
4 beds2 baths2,946 sq ft
679 Warwick Rd, Winchester, NH 03470
$629,000
2 beds1.5 baths5,567 sq ft
581 Keene Rd, Winchester, NH 03470
See all

Provided by Redfin

Sale history for 27 Headlands Rd

Date

Event

Price

PrimeMLS #3

Jul 27, 2026

Price Changed

$715,000

$486/sq ft

May 29, 2026

Price Changed

$720,000

$490/sq ft

Nov 19, 2025

Price Changed

$725,000

$493/sq ft

PrimeMLS #4911086

Dec 22, 2022

Sold

$650,000

$442/sq ft

Dec 21, 2022

Pending

—

Sep 6, 2022

Contingent

—

Jun 27, 2022

Relisted

—

Jun 7, 2022

Contingent

—

May 20, 2022

Listed

$679,000

$462/sq ft

PrimeMLS #4742566

May 15, 2019

Sold

$268,391

$183/sq ft

Apr 9, 2019

Pending

—

Mar 29, 2019

Listed

$287,000

$195/sq ft

+34

Enjoy year round living on pristine Forest Lake. House is oriented to maximize views of the lake from all 3 floors. Large deck affords wonderful outdoor space for outdoor living and entertaining. Post and beam style home with soaring cathedral ceiling, exposed beams, wood floors and walls. Back of house facing the lake has giant picture windows and glass doors. Multiple docks. Fire pit near water's edge. House is in move-in ready condition.

PrimeMLS #2

Oct 1, 2018

Price Changed

$287,000

$195/sq ft

Jul 26, 2018

Price Changed

$289,000

$197/sq ft

PrimeMLS #1

Jul 10, 2015

Price Changed

$309,000

$210/sq ft

PrimeMLS #158516

Jan 31, 2005

Sold

$255,000

$173/sq ft

Jul 9, 2004

Listed

$269,000

$183/sq ft

PrimeMLS #790010

Jan 23, 2001

Sold

$127,500

$87/sq ft

Jan 20, 2001

Listed

$139,900

$95/sq ft

Year

Property tax

Land + Additions

Assessment*

2024

$8,623 (−8.6%)

$129,100 + $165,700

$294,800

2023

$9,434 (+24.4%)

$129,100 + $168,700

$297,800

2022

$7,585 (−9.2%)

$129,100 + $135,200

$264,300

2021

$8,358 (+10.8%)

$129,100 + $133,800

$262,900

2020

$7,546 (−11.9%)

$129,100 + $133,200

$262,300

2019

$8,564 (+2.6%)

$116,500 + $123,800

$240,300

2018

$8,346 (+32.8%)

$116,500 + $123,800

$240,300

2016

$6,286 (−0.2%)

$85,400 + $120,500

$205,900

2015

$6,296 (−7.8%)

$85,400 + $120,500

$205,900

2013

$6,831

$101,700 + $120,600

$222,300

Tax history for 27 Headlands Rd

Year

Property tax

Land + Additions

Assessment*

2024

$8,623 (−8.6%)

$129,100 + $165,700

$294,800

2023

$9,434 (+24.4%)

$129,100 + $168,700

$297,800

2022

$7,585 (−9.2%)

$129,100 + $135,200

$264,300

2021

$8,358 (+10.8%)

$129,100 + $133,800

$262,900

2020

$7,546 (−11.9%)

$129,100 + $133,200

$262,300

2019

$8,564 (+2.6%)

$116,500 + $123,800

$240,300

2018

$8,346 (+32.8%)

$116,500 + $123,800

$240,300

2016

$6,286 (−0.2%)

$85,400 + $120,500

$205,900

2015

$6,296 (−7.8%)

$85,400 + $120,500

$205,900

2013

$6,831

$101,700 + $120,600

$222,300

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

Baths

1.5

Stories

Lot width

—

Lot depth

—

Lot size

6,970 Sq. Ft.

Year renovated

—

Sq. Ft.

1,387

Year built

1992

Style

Single Family Residential

County

Cheshire County

APN

186869

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Aug 5, 2026.

Property details

Interior

Bathroom Information
# of Baths (full): 1
# of Baths (1/2): 1

Basement Information
Basement: Yes
Basement Access: Walkout
Finished, Full, Walkout

Other Interior Features
# of Rooms: 4
Flooring: Carpet, Wood, Vinyl Plank
Water Heater: Electric
Cathedral Ceiling, Fireplace - Gas, Kitchen Island

Equipment & Appliance Information
Dishwasher, Microwave, Range - Gas, Refrigerator
Smoke Detector

Exterior

Building Information
Construction Status: Existing
Approximate Sq. Ft. Total Finished: 1470
Approximate Sq. Ft. Total: 1620
Docks, Private Dock, Shed
Construction: Post and Beam, Wood Frame
Foundation: Concrete, Poured Concrete
Roof: Shingle - Architectural
Exterior: Shake, Vinyl Siding

Driveway
Gravel

Lot, Zoning, & Easement Information
Lot: 16
Lake Access, Lake Frontage, Lake View, Landscaped, Steep, Water View

Boat, Moorage, and Water Information
Water Body Name: Forest Lake

Other Property & Lot Information
Year Built: 1992
Water View: Yes
Water View: Y
Waterfront: Yes
Waterfront Rights: Exclusively Owned
Water Body Name: Forest Lake
Water Body Access: Yes
Directly Adjoining

Financial

Tax Information
Tax Year: 2021
Gross Amount Tax: 8358

Other Tax Information
Page Deed: 638

Utilities

Heating & Cooling Information
Cooling: Mini Split
Heat: Mini Split
Heat Fuel: Electric

Sewer Information
Leach Field, Leach Field - On-Site, On-Site Septic Exists, Septic Design Available, Septic

Electric Information
100 Amp, Circuit Breaker(s)

Water Information
Public
Water Frontage Length: 60

Other Utilities Information
Gas - On-Site, Gas - Underground, High Speed Intrnt -AtSite, Telephone At Site

Location

Road Information
Road Frontage: Yes
Road Frontage Length: 70
Paved, Public

Other Location Information
Directions: Route 10 south to Winchester. Left onto Forest Lake Road .8 miles. Right onto Headlands Road .1 miles. Property on right.
Block: 0

Public facts

Beds: 2
Baths: 1.5
Sq. Ft.: 1,387
Stories: 2.0
Lot Size: 6,970 square feet
Style: Single Family Residential
Year Built: 1992
Year Renovated: —
County: Cheshire County
APN: 186869

Home facts updated by county records on Aug 5, 2026

Other

Water Body Information
Lake

Around this home

Schools

K - 12
Preschool & daycare

Winchester School

Public PreK-8 • Assigned • 1.6mi

3/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

3/10 Heat Factor

7 days above 93° expected this year, 17 days in 30 years

4/10 Wind Factor

11% chance of strong winds in next 30 years

1/10 Air Factor

0 unhealthy days expected this year, 0 days in 30 years

Provided by First Street

Historical weather

Winchester, NH • 03470

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

78/ 100

Good sunlight

Sunscore

This home ranks in the top 7% for direct sun exposure in Winchester. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

8.3 hrs

4 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$600,000 – $726,000

Reach more buyers when you sell with Redfin. Save up to $6,308 in fees. 3 minutes to get started.

Get a free, detailed breakdown of how we calculated your estimate.

Nearby similar homes

$140,000

1 bed1 bath968 sq ft

31 Watson Rd, Winchester, NH 03470

1 acre country lot • Partial metal roof • 1 acre lot

$230,000

3 beds2 baths1,615 sq ft

109 Northfield Rd, Hinsdale, NH 03451

Spacious 1-acre lot • In-town lot • 1.18 acre lot

$629,000

2 beds1.5 baths5,567 sq ft

581 Keene Rd, Winchester, NH 03470

Excellent visibility • Easy access • Additional buildings

$343,000

4 beds2 baths2,300 sq ft

5 Highland Ave, Hinsdale, NH 03451

Large corner lot • Three-season porch • Huge 2-bay garage

$369,500

3 beds2 baths1,630 sq ft

521 Northfield Rd, Hinsdale, NH 03451

New septic • New roof • New kitchen

$350,000

3 beds2 baths1,053 sq ft

3080 Fort Bridgman Rd, Vernon, VT 05354

1/2 acre homestead • New floors • New bath

New listings for sale in 03470

$699,000

8 beds4 baths3,515 sq ft

37 Michigan St, Winchester, NH 03470

Open concept layout • Durable metal roof • Coin op laundry room

$499,900

4 beds2 baths2,946 sq ft

679 Warwick Rd, Winchester, NH 03470

Iconic stone walls • Built-in hutch • Cozy wood stove

$629,000

2 beds1.5 baths5,567 sq ft

581 Keene Rd, Winchester, NH 03470

Excellent visibility • Easy access • Additional buildings

Home values near 27 Headlands Rd

Data from public records.

Address	Redfin Estimate
35 Headlands Road, Winchester, NH 2 Beds \| 1 Baths \| 878 Sq. Ft.	$257,332
33 Headlands Road, Winchester, NH 2 Beds \| 1 Baths \| - Sq. Ft.	$359,743
19 Headlands Road, Winchester, NH 3 Beds \| 1 Baths \| 1485 Sq. Ft.	$426,751
23 Headlands Road, Winchester, NH 2 Beds \| 2 Baths \| 1768 Sq. Ft.	$459,385

Address	Redfin Estimate
25 Headlands Road, Winchester, NH 1 Beds \| 1 Baths \| 756 Sq. Ft.	$432,957
20 Headlands Road, Winchester, NH 2 Beds \| 1 Baths \| 1188 Sq. Ft.	$165,397
31 Headlands Road, Winchester, NH 2 Beds \| 1 Baths \| 1489 Sq. Ft.	$389,618
19 Headlands Road, Winchester, NH 3 Beds \| 1.5 Baths \| 1767 Sq. Ft.	$401,327

Address	Redfin Estimate
31 Headlands Road, Winchester, NH 2 Beds \| 1 Baths \| 1489 Sq. Ft.	$318,904
23 Headlands Road, Winchester, NH 2 Beds \| 2 Baths \| 1768 Sq. Ft.	$526,303
20 Headlands Road, Winchester, NH 2 Beds \| 1 Baths \| 837 Sq. Ft.	$202,921

Property information provided by PrimeMLS when last listed in 2022. This data may not match . Learn more.

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

Redfin Brokerage Licenses

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

GreatSchools Ratings provided by GreatSchools.org.

Swanzey homes for sale
Chesterfield homes for sale
Rindge homes for sale
Harrisville homes for sale
Fitzwilliam homes for sale

Houses for sale near me	Nashua, NH homes for sale	Derry, NH homes for sale
Land for sale near me	Portsmouth, NH homes for sale	Hudson, NH homes for sale
Open Houses near me	Salem, NH homes for sale	Winchester Property Records
Condos for sale near me	Manchester, NH homes for sale	NH New Listings
Agents near me	Londonderry, NH homes for sale	Winchester Housing Market

Brattleboro homes for sale
Keene homes for sale
Athol homes for sale

About this home

Redfin Estimate

Earn from this home

Market trends in 03470, NH

Sale history for 27 Headlands Rd

Tax history for 27 Headlands Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 03470

Home values near 27 Headlands Rd

More real estate resources