111 Chestnut St, Upton, MA 01568
Property image
Property image
OFF MARKET

111 Chestnut St
Upton, MA 01568

  • 3 Beds
  • 2.5 Baths
  • 3,120 sqft (on 1.91 acres)

$938,700

Trulia Estimate
as of Aug 2, 2026
Est. Refi. Payment $5,835/mo*
Refinance Your Home

$938,700

Trulia Estimate
as of Aug 2, 2026
Est. Refi. Payment $5,835/mo*
Refinance Your Home
3 Beds
2.5 Baths
3,120 sqft
(on 1.91 acres)

Local Information

  • Map ViewExplore the area around 111 Chestnut St.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1997
Lot Size
1.91 acres
Living Area
3,120 sqft
Price/Sqft
$301
Parking
3 Car Garage

About this House

Welcome guests into this wonderful elegant oasis featuring a bright and open floor plan with a stunning two-story foyer and beautiful turned staircase. The heart of this beautiful home is the custom kitchen featuring state-of-the-art downdraft induction Wolf cooktop, built in refrigerator & wall ovens that are perfect for any culinary enthusiast. The grand dining room with elegant moldings is a must-have for large gatherings. Step-down to the luxurious family room with stunning fireplace & sweeping windows that overlook your gorgeous gardens, huge level backyard, & sensational inground gunite pool. This space seamlessly blends indoor & outdoor living w/a custom-designed covered back deck, creating the perfect environment for relaxation & entertainment. Enjoy the wonderful library w/beautiful built-ins for those essential work moments. At the end of the day make your way upstairs to indulge in the expansive primary en-suite that feels like a spa retreat. You are HOME.
111 Chestnut St, Upton, MA 01568 is a 3 bedroom, 3 bathroom, 3,120 sqft single-family home built in 1997. It last sold for $865,000 on Sep 19, 2024 (1% below the $874,500 asking price). It is currently off market. The Trulia Estimate is $938,700, with a rent estimate of $2,942/month.

Home Details for 111 Chestnut St

Interior Features

Interior Details
Basement: Full,Partially Finished,Interior Entry,Garage AccessNumber of Rooms: 10Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Master Bathroom, Bathroom 1, Bathroom 2, Bathroom 3, Dining Room, Family Room, Kitchen
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 3120 Square FeetFoundation Area: 1620
Appliances & Utilities
Utilities: for Electric Range, for Electric Oven, for Electric Dryer, Washer HookupAppliances: Water Heater, Oven, Microwave, Range, Refrigerator, Washer, Dryer, Water Treatment, Wine Refrigerator, ENERGY STAR Qualified Dishwasher, Water SoftenerDryerLaundry: Flooring - Stone/Ceramic Tile,Beadboard,Second Floor,Electric Dryer Hookup,Washer HookupMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Forced Air,OilHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 1Fireplace: Family RoomHas a FireplaceNo Spa
Gas & Electric
Electric: 200+ Amp Service
Windows, Doors, Floors & Walls
Window: Insulated WindowsDoor: French DoorsFlooring: Tile, Hardwood, Flooring - Hardwood, Flooring - Stone/Ceramic Tile, Laminate
Levels, Entrance, & Accessibility
Floors: Tile, Hardwood, Flooring Hardwood, Flooring Stone Ceramic Tile, Laminate

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Porch, Deck - Roof, Patio, CoveredFencing: FencedExterior: Porch, Deck - Roof, Patio, Covered Patio/Deck, Pool - Inground, Rain Gutters, Fenced Yard, Garden, Stone WallFoundation: Concrete PerimeterGardenHas a Private Pool
Parking & Garage
Number of Garage Spaces: 3Number of Covered Spaces: 3Open Parking Spaces: 4No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 7Parking: Attached,Garage Door Opener,Workshop in Garage,Garage Faces Side,Paved Drive,Off Street
Pool
Pool: In GroundPool
Frontage
Road Frontage: PublicNot on Waterfront
Water & Sewer
Sewer: Private Sewer

Property Information

Year Built
Year Built: 1997
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Construction Materials: FrameNot Attached PropertyDoes Not Include Home Warranty
Property Information
Not Included in Sale: Staging Furniture.Parcel Number: 3274771

Price & Status

Price
List Price: $874,500
Status Change & Dates
Off Market Date: Mon Sep 02 2024

Active Status

MLS Status: Sold

Media

Location

Direction & Address
City: Upton
School Information
Elementary School: MemorialJr High / Middle School: MiscoeHigh School: Nipmuc

Building

Building Area
Building Area: 3120 Square Feet

Community

Community Features: Walk/Jog Trails, Stable(s), Bike Path, Conservation Area, House of Worship, Public SchoolNot Senior Community

HOA

No HOA

Lot Information

Lot Area: 1.9052 Acres

Miscellaneous

BasementMls Number: 73258006

Additional Information

Walk/Jog TrailsStable(s)Bike PathConservation AreaHouse of WorshipPublic School
Last check for updates: about 7 hours ago
Listed by THE LASH GROUP, (508) 603-9898
Keller Williams Boston MetroWest, (508) 877-6500
Laurie Ann Babbitt-Strapponi, (508) 922-9471
Bought with: Nick McNeil, (774) 276-5937, McNeil Real Estate Inc., (508) 266-5285
Source: MLS PIN, MLS#73258006

Price History for 111 Chestnut St

DatePriceEventSource
09/19/2024$865,000Sold
MLS PIN #73258006
07/24/2024$874,500PriceChange
MLS PIN #73258006
06/27/2024$889,500Listed For SaleMLS PIN #73258006
04/25/2001$512,500Sold
N/A

Market trends in Upton

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
37
2MoM
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Property Tax and Assessment

Year2025
Tax$10,759
Assessment$818,200
Home facts updated by county records

Comparable Sales for 111 Chestnut St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
4 Farrar Rd, Upton, MA
0.44
Single-Family Home
$795,000
11/24/25
4
3
2,536
8 Miscoe Hill Rd, Upton, MA
0.74
Single-Family Home
$925,000
08/22/25
4
2.5
2,856
29 Shore Dr, Upton, MA
0.54
Single-Family Home
$600,000
12/12/25
3
2.5
1,732
154 South St, Upton, MA
0.83
Single-Family Home
$1,000,000
06/22/26
4
3.5
4,265
7 River Bend Rd, Upton, MA
1.11
Single-Family Home
$1,050,000
09/25/25
4
3.5
4,178
56 Shore Dr, Upton, MA
0.55
Single-Family Home
$472,800
09/05/25
3
1.5
1,320
179 South St, Upton, MA
1.37
Single-Family Home
$1,050,000
06/22/26
3
2.5
3,237
177 South St, Upton, MA
1.33
Single-Family Home
$918,000
09/11/25
4
4
4,815
16 Rawson Farm Dr, Mendon, MA
1.49
Single-Family Home
$1,099,500
08/11/25
4
2.5
2,884
36 Brooks St, Upton, MA
1.56
Single-Family Home
$800,000
06/18/26
4
3
2,598

Nearby homes

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Assigned Schools

These are the assigned schools for 111 Chestnut St.
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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 Upton

At least 28 Trulia users voted on each feature.

  • 94 % Say car is needed

  • 88 % Say parking is easy

  • 83 % Say yards are well-kept

  • 75 % Say it's dog friendly

  • 73 % Say people would walk alone at night

  • 71 % Say there's wildlife

  • 68 % Say they plan to stay for at least 5 years

  • 67 % Say there's holiday spirit

  • 66 % Say it's quiet

  • 60 % Say neighbors are friendly

  • 59 % Say kids play outside

  • 48 % Say there are sidewalks

  • 30 % Say there are community events

  • 25 % Say streets are well-lit

  • 17 % Say it's walkable to restaurants

  • 13 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Fernando M.
    "I've lived in Upton now for almost a Decade and it's an amazing town. The community is amazing, people are respectful, lots of community events, lots of recreational areas from Kiwanis beach, Upton State Park, Peppercorn Hill Conservation Area and other location, the schools are excellent, teachers care about the students, great academic and athletic departments. Upton truly is a place you can raise a family and feel safe."
    0
    Flag
  • Kristy G. B.
    "Must leave early to get to Boston or Boston area. Early is 6:30 or leave after 9 am. There is a lot of traffic going East, but is going on the other direction not as bad. There is not a lot of traffic on the town, but on the boarders of all surrounding towns there is traffic at peak hours."
    7
    Flag
  • Kristy G. B.
    "We’ve lived here for 9 years and everyone is very friendly and looks out for each other, yet you maintain your privacy. It’s a great sense of community with lots of young families."
    1
    Flag
  • Bapalladini
    "it's a nice area. my dad loves it here. nice neighborhood, good community. old time feel to the area. plenty of hiking, parks etc. good schools, overall great "
    2
    Flag
  • Kristy G. B.
    "Safe, tight knit community where everyone is looking out for each other. The community is growing and young families are moving in. It definitely has a small town feel. "
    2
    Flag
  • Lily G.
    "plenty of parks to walk dogs. big yards and land for dogs to play and have space. close to tuffs animal hospital. "
    1
    Flag
  • Paola W. O.
    "Tons of areas to walk dogs. You just have to be careful with wild animals that could attack your dogs at night. "
    2
    Flag
  • Acmalzone
    "Small, friendly neighborhood town. Great neighbors. Awesome school system. Safe town. No chain stores or chain restaurants. All Ma & Pop shops and family owned restaurants."
    2
    Flag
  • annacollari
    "I have lived here for 2 years and it has already topped all the 10 other places i lived in, it is very clean, and my kids get a great education at the two high schools and one elementary school. All the people here are so nice and friendly. There are loads of places to walk and hang out, and it is great for kids, there is one park and baseball field, and there is another public park at the Elementary school. Upton is a Great place to live!"
    0
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  • Petersonk17
    "I live here since I was born and I think it is a wonderful neighborhood to live in. Lots of kids live around so it is good for families with children."
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The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
The MLS listing information displayed is deemed reliable, but is not guaranteed accurate by the MLS.