299 Old Chesterfield Road
Description
Sold By BH&G - The Masiello Group
- Listed by: Pat Paquette • BH&G - The Masiello Group
Recent comparable sales
Median sold price
$236,000
Avg days on market
39
Sale-to-list ratio
98.4%
Winchester, NH
9 comparable properties found
$175,000
Sold 12/05/25
- 2
- Bedrooms
- 2
- Bathrooms
- 980
- Square Feet
- 0.35
- Acres
$225,000
Sold 08/28/25
- 3
- Bedrooms
- 2
- Bathrooms
- 1,320
- Square Feet
- 0.17
- Acres
$195,000
Sold 07/03/25
- 2
- Bedrooms
- 2
- Bathrooms
- 1,068
- Square Feet
- 1.2
- Acres
$236,000
Sold 10/10/24
- 2
- Bedrooms
- 2
- Bathrooms
- 1,120
- Square Feet
- 2.2
- Acres
$290,000
Sold 07/13/26
- 3
- Bedrooms
- 2
- Bathrooms
- 1,100
- Square Feet
- 0.33
- Acres
$265,000
Sold 10/10/25
- 2
- Bedrooms
- 2
- Bathrooms
- 1,220
- Square Feet
- 0.37
- Acres
$225,000
Sold 02/18/25
- 2
- Bedrooms
- 1
- Bathrooms
- 1,157
- Square Feet
- 0.4
- Acres
$250,000
Sold 04/02/26
- 2
- Bedrooms
- 2
- Bathrooms
- 1,313
- Square Feet
- 0.3
- Acres
Location
Payment Calculator
$1,337 per month
30 year fixed, 6.71% Interest
$1,059
$278
$0
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1Property Information for 299 Old Chesterfield Road
- Taxes: $3,334 / year
- MLS Type: Residential / Single Family
- County: Cheshire County
- Zoning: RURAL
- Stories: 1
- Year Built: 1950
- Lot Size: 70.00 AC / 3,049,200 SF
- City: Winchester
- County: NH-Cheshire
- Directions: RT 10S TO CENTER OF WINCHESTER - BEAR (R) ON ELM, FOLLOW 2 MILES PASS HOME ON (R) FOLLOW TO THE END.
- Seasonal: No
- State: NH
- Map: 11
- Zip: 03470
- Tax - Gross Amount: $3,334.00
- Tax Year: 2001
- School - High: Thayer High School
- Garage: Yes
- Garage Capacity: 1.00
- Driveway: Gravel
- Lot: 24
- Lot - Sqft: 3049200.0
- Lot Size Acres: 70.0
- Square Feet Apx Finished Above Grade: 1200.0
- Square Feet Apx Total Finished: 1200.0
- Property Class: Residential
- Property Type: Single Family
- Flood Zone: Unknown
- Foundation: Concrete
- Surveyed: Yes
- Year Built: 1950
- Electric: 100 Amp, Circuit Breaker(s)
- Sewer: Private
- Color: WHITE
- Features - Exterior: Deck, Outbuilding, Porch - Screened
- Roads: Dead End, Private
- Roof: Shingle - Asphalt
- Appliances: Dishwasher, Range - Electric
- Basement Description: Full
- Baths - Total: 2
- Baths - Full: 2
- Half Baths: 0
- Three Quarter Bath: 0
- Rooms - Total: 7
- Bedrooms - Total: 2
- Equipment: Smoke Detector
- Features - Interior: Attic, Ceiling Fan, Fireplace - Wood, Laundry Hook-ups, Master BR w/ BA
- Heat Fuel: Oil
- Heating: Baseboard
- Total Stories: 1
- Room Dimensions: 14X14
- Room Level: 1
- Room Type: Kitchen
- Room Dimensions: 14X13
- Room Level: 1
- Room Type: Dining Room
- Room Dimensions: 13X20
- Room Level: 1
- Room Type: Living Room
- Room Dimensions: 20X16
- Room Level: 1
- Room Type: Master Bedroom
- Room Dimensions: 18X12
- Room Level: 1
- Room Type: Bedroom
- Room Dimensions: 8X8
- Room Type: Den
- Room Dimensions: 7.5X11
- Room Level: 1
- Room Type: Other
- Room Level: 1
- Room Type: Bath - Full
- Room Level: 1
- Room Type: Bath - 3/4
Property History for 299 Old Chesterfield Road
| Date | Event & Source | Price | Appreciation |
|---|---|---|---|
| Nov 20, 2002 | Sold New England Real Estate Network #856106 | $205,000 | — |
| Oct 14, 2002 | Pending New England Real Estate Network #856106 | — | |
| Jul 8, 2002 | Listed (Active) New England Real Estate Network #856106 | $235,000 | — |
| Date | Event & Source | Price |
|---|---|---|
| 11/20/2002 | Sold New England Real Estate Network #856106 | $205,000 |
| 10/14/2002 | Pending New England Real Estate Network #856106 | — |
| 07/08/2002 | Listed (Active) New England Real Estate Network #856106 | $235,000 |
For completeness, we often displays two records for one sale: the MLS record and the public record.
Public Records for 299 Old Chesterfield Road
Schools near 299 Old Chesterfield Road
Rating | School | Type | Grades | Distance |
|---|---|---|---|---|
| Public - | PK to 8 | |||
| 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.
Similar Homes
New listings in 03470
$290,000
- Unavailable
- Bedrooms
- 4
- Bathrooms
- 4,739
- Square Feet
- 3.02
- Acres
$3,995,000
- 4
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Nearby home values
| Address | Sold price | Beds | Baths | Sqft | Lot (Sqft) |
|---|---|---|---|---|---|
This home: 299 Old Chesterfield Road, Winchester, NH 03470 | $205,000 | 2 | 2 | 1,200 | 3,049,200 |
– | – | – | – | 304,920 | |
$149,900 | 2 | 1 | 1,220 | 27,442 | |
$9,000 | 3 | 1 | 1,482 | 400,752 | |
– | 1 | 1 | 1,136 | 135,036 | |
– | – | – | – | 370,260 | |
$190,000 | 3 | 2 | 1,877 | 901,692 | |
$40,000 | 3 | 2 | 1,026 | 352,836 | |
– | 4 | 1.5 | 1,462 | 25,700 | |
– | – | – | – | 69,696 | |
$173,500 | 2 | 1.5 | 1,375 | 33,977 | |
$40,000 | – | – | – | 352,836 | |
$220,000 | 3 | 2 | 1,800 | 1,306,800 | |
– | 2 | 1 | 1,423 | 152,460 | |
– | 3 | 1 | 1,914 | 682,585 | |
– | 1 | 1 | 1,175 | 51,836 |
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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim 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 seller's discretion. No financial or legal advice provided. Equal Housing Opportunity.
Listing Courtesy of BH&G - The Masiello Group
Copyright 2026 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 09/11/2026 12:07 PM
