20 Pudding Hill Rd, Winchester, NH 03470
OFF MARKET

20 Pudding Hill Rd
Winchester, NH 03470

  • 4 Beds
  • 2 Baths
  • 1,620 sqft (on 1.30 acres)

$323,500

Trulia Estimate
as of Jul 9, 2026
Est. Refi. Payment $2,189/mo*
Refinance Your Home

$323,500

Trulia Estimate
as of Jul 9, 2026
Est. Refi. Payment $2,189/mo*
Refinance Your Home
4 Beds
2 Baths
1,620 sqft
(on 1.30 acres)

Local Information

  • Map ViewExplore the area around 20 Pudding Hill Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School
  • Shop & Eat
-- mins to
Commute Destination

Description

Above the picturesque Roaring Brook is a duplex that is in terriffic condition. True side by side duplex with 2BRs each side. This would make an ideal owner occupied property with long term tenants next door. Or for extended family! Feels like a home and not a rental. Both units are clean and updated, with separate basement access and separate utilities. The yard is spacious and runs down to the lovely brookside. Low maintenance siding and metal roofing make this an easy choice. 48 hours notice needed to show please.
20 Pudding Hill Rd, Winchester, NH 03470 is a 4 bedroom, 2 bathroom, 1,620 sqft single-family home built in 1989. It last sold for $186,000 on Apr 4, 2022. It is currently off market. The Trulia Estimate is $323,500, with a rent estimate of $2,614/month.

Home Highlights

Parking
No Info
Outdoor
No Info
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 20 Pudding Hill Rd

Interior Features

Heating & Cooling
Heating: Radiant, GasHeating Fuel: Radiant
Levels, Entrance, & Accessibility
Stories: 1Floors: Laminate, Linoleum Vinyl
Interior Details
Number of Rooms: 8
Appliances & Utilities
Refrigerator

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Vinyl

Property Information

Year Built
Year Built: 1989
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Lot Information

Lot Area: 1.30 acres

Price History for 20 Pudding Hill Rd

DatePriceEventSource
04/04/2022$186,000Sold
N/A
01/08/2021ListingRemovedBetter Homes and Gardens Real Estate The Masiello Group
12/23/2020$225,000PendingAgent Provided
07/01/2020$225,000Listed For SaleAgent Provided

Market trends in Winchester

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
13
2MoM
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Property Tax and Assessment

Year2024
Tax$4,578
Assessment$156,500
Home facts updated by county records

Comparable Sales for 20 Pudding Hill Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
12 Pudding Hill Road, Winchester, NH
0.06
Single-Family Home
$361,000
06/18/26
3
2
1,546
384 Richmond Road, Winchester, NH
0.29
Single-Family Home
$310,000
08/15/25
2
2
1,296
415 Richmond Road, Winchester, NH
0.40
Single-Family Home
$249,500
11/14/25
2
1.5
1,440
30 Acorn Drive, Winchester, NH
0.50
Single-Family Home
$375,000
06/18/26
2
2
1,612
9 Scotland Rd, Winchester, NH
0.40
Single-Family Home
$98,000
01/05/26
3
1
1,311
220 Richmond Road, Winchester, NH
0.78
Single-Family Home
$265,000
10/10/25
2
1.5
1,220
290 Scotland Road, Winchester, NH
0.94
Single-Family Home
$283,000
05/07/26
3
2
1,092
119 Warwick Road, Winchester, NH
1.32
Single-Family Home
$440,000
06/22/26
3
2
2,232
19 Toofs Drive, Winchester, NH
1.18
Single-Family Home
$295,000
02/27/26
3
2
1,344
111 Warwick Road, Winchester, NH
1.43
Single-Family Home
$430,000
12/16/25
4
2
2,656

Nearby homes

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Assigned Schools

These are the assigned schools for 20 Pudding Hill Rd.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Winchester

At least 16 Trulia users voted on each feature.

  • 91 % Say parking is easy

  • 88 % Say car is needed

  • 80 % Say yards are well-kept

  • 76 % Say there's holiday spirit

  • 73 % Say there's wildlife

  • 68 % Say people would walk alone at night

  • 60 % Say it's dog friendly

  • 56 % Say it's quiet

  • 53 % Say kids play outside

  • 48 % Say neighbors are friendly

  • 43 % Say they plan to stay for at least 5 years

  • 35 % Say it's walkable to grocery stores

  • 31 % Say streets are well-lit

  • 30 % Say there are community events

  • 23 % Say it's walkable to restaurants

  • 17 % Say there are sidewalks

Sourced by Trulia users. Learn more about our methodology.
  • Flynnstrucking
    "there is Plenty of open space to walk your dog without having to worry about picking up after it. you can have your own private trails right out your back door"
    0
    Flag
  • Angelica M.
    "Dope heads. Idk it’s not the best or worst place to live. It’s far away from society and school sucks"
    0
    Flag
  • unknown
    "Boring. Druggies, condemned, abandon, no activity, lots of kid parks, school, noises, fast cars, no laws, rude people"
    0
    Flag
  • Jeannette D.
    "Compared to other outlying Cheshire County towns, Winchester, NH gets the highest mark for in-town amenities. Winchester, NH has its own locally owned grocery store, hardware store, pharmacy, clinic, bank and more! Additionally, the natural amenities are outstanding and include, Forest Lake, Ashuelot River, 14,000 acre Pisgah State Park, Rails to Trails. In Winchester, NH, you get the best of both worlds - rural living with close by amenities. AND you can get there from here! 15 minutes to I91 in Berndarston, MA, 20 minutes to Keene, NH, Greenfield, MA or Brattleboro, VT."
    8
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Apartments for Rent

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Homes for sale near 20 Pudding Hill Rd

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Off Market Homes Near 20 Pudding Hill Rd

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