OFF MARKET

Listed by Pat Paquette • BHG Masiello Keene. Bought with BHG Masiello Keene.

Off Market Nov 2002 for $205K

$526,477

•

1,200

sq ft

299 OLD CHESTERFIELD Rd, Winchester, NH 03470

About this home

Single-familyProperty Type

1950Year Built

70 acresLot Size

$439Est. Price/Sq.Ft.

1 car garageParking

Listed by Pat Paquette • BHG Masiello Keene

Bought with Pat Paquette • BHG Masiello Keene

Redfin checked: 2 minutes ago

•Source:PrimeMLS #856106

Redfin Estimate

$526,477

$321K since sold in November 2002$9,000 since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 52.7% higher than the average sale price ($345K) of 6 comparable homes.

BOUGHT WITH REDFIN AUG 14, 2026
$430,000
A
1 bed2 baths1,232 sq ft
152 Old Chesterfield Rd, Winchester, NH 03470
SOLD APR 3, 2026
$326,000
B
3 beds2 baths1,018 sq ft
73 Plain Rd, Hinsdale, NH 03451
SOLD JUL 13, 2026
$290,000
C
3 beds2 baths1,100 sq ft
82 Howard St, Winchester, NH 03470
SOLD MAY 7, 2026
$283,000
D
3 beds2 baths1,092 sq ft
290 Scotland Rd, Winchester, NH 03470
SOLD AUG 27, 2026
$365,000
E
3 beds1.5 baths1,192 sq ft
55 Verry Brook Rd, Winchester, NH 03470
SOLD JUN 18, 2026
$375,000
F
2 beds2 baths1,612 sq ft
30 Acorn Dr, Winchester, NH 03470

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Earn from this home

Sell

$443,172

Est. take-home

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Rent

$2,795/mo

Redfin rental estimate

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Market trends in 03470, NH

Last updated August 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

99.7%

0.8% MoM

Median sale price

$377K

$2K MoM

Avg. days on market

53d

3 days MoM

Recently sold homes

1 MoM

New listings for sale

$479,900
3 beds2 baths2,016 sq ft
366 Keene Rd, Winchester, NH 03470
See all

Provided by Redfin

Sale history for 299 OLD CHESTERFIELD Rd

Year

Property tax

Land + Additions

Assessment*

2024

$5,935 (−7.7%)

$57,215 + $145,700

$202,915

2023

$6,432 (+10.3%)

$57,335 + $145,700

$203,035

2022

$5,834 (−9.8%)

$57,574 + $145,700

$203,274

2021

$6,465 (+10.5%)

$57,672 + $145,700

$203,372

2020

$5,852 (−20.4%)

$57,705 + $145,700

$203,405

2019

$7,348 (+2.7%)

$53,980 + $152,200

$206,180

2018

$7,157 (+11.8%)

$53,883 + $152,200

$206,083

2016

$6,402

$57,590 + $152,100

$209,690

2015

$6,405 (+1.6%)

$57,342 + $152,100

$209,442

2013

$6,303

$81,209 + $123,900

$205,109

Tax history for 299 OLD CHESTERFIELD Rd

Year

Property tax

Land + Additions

Assessment*

2024

$5,935 (−7.7%)

$57,215 + $145,700

$202,915

2023

$6,432 (+10.3%)

$57,335 + $145,700

$203,035

2022

$5,834 (−9.8%)

$57,574 + $145,700

$203,274

2021

$6,465 (+10.5%)

$57,672 + $145,700

$203,372

2020

$5,852 (−20.4%)

$57,705 + $145,700

$203,405

2019

$7,348 (+2.7%)

$53,980 + $152,200

$206,180

2018

$7,157 (+11.8%)

$53,883 + $152,200

$206,083

2016

$6,402

$57,590 + $152,100

$209,690

2015

$6,405 (+1.6%)

$57,342 + $152,100

$209,442

2013

$6,303

$81,209 + $123,900

$205,109

*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

Stories

Lot width

—

Lot depth

—

Lot size

32.1 Acres

Year renovated

—

Sq. Ft.

1,893

Year built

1950

Style

Single Family Residential

County

Cheshire County

APN

512177

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Aug 5, 2026.

Property details

Parking

Parking & Garage
Garage Capacity: 1
Location: Under
Barn

Interior

Bathroom Information
# of Baths (full): 2

Basement Information
Full

Other Interior Features
# of Rooms: 7
Water Heater: Off Boiler
Attic, Ceiling Fan, Fireplace - Wood, Laundry Hook-ups, Master Bedroom With Bath

Equipment & Appliance Information
Dishwasher, Range - Electric
Smoke Detector

Room 1 Information
Kitchen
Kitchen
Dimensions: 14X14
Level: 1

Room 2 Information
Dining Room
Dimensions: 14X13
Level: 1

Room 3 Information
Living Room
Dimensions: 13X20
Level: 1

Room 7 Information
Master Bedroom
Dimensions: 20X16
Level: 1

Room 8 Information
Bedroom
Dimensions: 18X12
Level: 1

Room 12 Information
Den
Dimensions: 8X8

Room 13 Information
Other
Dimensions: 7.5X11
Level: 1

Room 16 Information
Full Bath
Level: 1

Room 17 Information
3/4 Bath
Level: 1

Exterior

Building Information
Approximate Sq. Ft. Total Finished: 1200
Color: WHITE
Deck, Outbuilding, Porch - Screened
Construction: Wood Frame
Foundation: Concrete
Roof: Shingle - Asphalt
Exterior: Vinyl

Driveway
Gravel

Lot, Zoning, & Easement Information
Lot: 24
Farm - Horse/Animal, View, Wooded

Survey Information
Surveyed: Yes

Other Property & Lot Information
Year Built: 1950

Financial

Tax Information
Tax Year: 2001
Gross Amount Tax: 3334

Other Tax Information
Page Deed: 0056

Utilities

Heating & Cooling Information
Heat: Baseboard
Heat Fuel: Oil

Sewer Information
Private

Electric Information
100 Amp, Circuit Breaker(s)

Water Information
Private

Location

Road Information
Dead End, Private

Other Location Information
Directions: RT 10S TO CENTER OF WINCHESTER - BEAR (R) ON ELM, FOLLOW 2 MILES PASS HOME ON (R) FOLLOW TO THE END.

Public facts

Beds: 2
Baths: 2.0
Sq. Ft.: 1,893
Stories: 1.0
Lot Size: 32.1 acres
Style: Single Family Residential
Year Built: 1950
Year Renovated: —
County: Cheshire County
APN: 512177

Home facts updated by county records on Aug 5, 2026

Other

Water Body Information
Flood Zone: Unknown

Around this home

Schools

Winchester School

Public PreK-8 • Assigned • 2.6mi

3/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

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

In this area, properties receive around 8.8 hours in June and 4 hours in December, placing it below the U.S. average for solar exposure.

8.8 hrs

4 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$501,000 – $606,000

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Nearby similar homes

$150,000

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New listings for sale in 03470

$479,900

3 beds2 baths2,016 sq ft

366 Keene Rd, Winchester, NH 03470

Home values near 299 OLD CHESTERFIELD Rd

Data from public records.

Address	Redfin Estimate
400 Old Chesterfield Rd, Winchester, NH 2 Beds \| 2 Baths \| 1344 Sq. Ft.	$225,410
310 Old Chesterfield Rd, Winchester, NH 1 Beds \| 1 Baths \| 1136 Sq. Ft.	$204,277

Address	Redfin Estimate
347 Old Chesterfield Rd, Winchester, NH 2 Beds \| 1 Baths \| 1423 Sq. Ft.	$336,799
340 Old Chesterfield Rd, Winchester, NH 3 Beds \| 2.5 Baths \| 2722 Sq. Ft.	$571,966

Address	Redfin Estimate
358 Old Chesterfield Rd, Winchester, NH 3 Beds \| 1.5 Baths \| 1877 Sq. Ft.	$466,754
259 Old Chesterfield Rd, Winchester, NH 3 Beds \| 1 Baths \| 1159 Sq. Ft.	$172,127

Property information provided by PrimeMLS when last listed in 2002. This data may not match . Learn more.

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