149 Chestnut St
Upton, MA 01568
4 Beds
2.5 Baths
2,252 sqft (on 3.24 acres)
4 Beds
2.5 Baths
2,252 sqft
(on 3.24 acres)
Homes for sale near 149 Chestnut St
NEW CONSTRUCTION2.03 ACRESGary Smith, Mendon Area Real Estate- 4.09 ACRESDiana Afonso, Afonso Real Estate
- OFF MARKET
- OFF MARKET
- OFF MARKET
- 1.38 ACRESKey to the Dream Realty Group, Coldwell Banker Realty - Franklin
- OFF MARKET
- OFF MARKET
- OFF MARKET
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Local Information
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Description
Welcome to Chestnut St. A winding country road across from a great fishing pond. Seasonal views of Taft pond where neighbors canoe, fish & ice skate. Three plus acre wooded lot offers wildlife, an above ground pool w/deck, rock walls, another dining deck, a brick patio & acres to plant gardens or forge trails..a truly private natural setting. The 1st floor has hardwood flooring, a sunken living room, family room, a formal dining room, a study or 1st floor bedroom, and a screened porch with hardwood floors that over looks the expansive yard. Most of the rooms have been freshly painted with a neutral palate. The 2nd level offers a large walk in storage closet in the 2nd floor hall. The sun drenched master ensuite has a 3/4 bath, new carpets and double closets to welcome you. The finished basement offers a heated bedroom, an awesome bar area, laundry ctr and walk out to the patio. The 3 story garage has 2 garage bays plus a 3rd floor for finishing (a total of 3 levels of usable space).
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.
Home Highlights
Parking
Garage
Outdoor
Patio, Deck
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
No Info
Home Details for 149 Chestnut St
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Heating & Cooling Heating: Other, ElectricHeating Fuel: Other |
Levels, Entrance, & Accessibility Stories: 2Floors: Hardwood |
Interior Details Number of Rooms: 9Types of Rooms: Dining Room, Family Room |
Appliances & Utilities DryerMicrowaveRefrigeratorWasher |
Fireplace & Spa Fireplace |
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Exterior Home Features Roof: AsphaltDeckExterior: WoodPatio |
Parking & Garage GarageParking Spaces: 10Parking: Garage Detached |
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Year Built Year Built: 1973 |
Property Type / Style Property Type: Single Family HomeArchitecture: Colonial |
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Units in Building: 8 |
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Lot Area: 3.24 acres |
Price History for 149 Chestnut St
| Date | Price | Event | Source |
|---|---|---|---|
| 07/06/2021 | $540,000 | Sold | MLS PIN #72841516 |
| 06/21/2021 | $495,000 | Pending | MLS PIN #72841516 |
| 06/08/2021 | $495,000 | Contingent | MLS PIN #72841516 |
| 06/02/2021 | $495,000 | Listed For Sale | MLS PIN #72841516 |
| 01/11/2018 | $400,000 | Sold | C21 Commonwealth Sold #72243795_01568 |
| 11/28/2017 | $408,900 | Pending | Agent Provided |
| 11/13/2017 | $408,900 | PendingToActive | Agent Provided |
| 11/09/2017 | $408,900 | Pending | Agent Provided |
| 11/07/2017 | $408,900 | PendingToActive | Agent Provided |
| 10/30/2017 | $408,900 | Pending | Agent Provided |
| 10/17/2017 | $408,900 | PriceChange | Agent Provided |
| 09/12/2017 | $409,000 | PriceChange | Agent Provided |
| 06/22/2017 | $419,000 | Listed For Sale | Agent Provided |
| 08/25/1995 | $208,000 | Sold | N/A |
| 06/03/1988 | $223,000 | Sold | N/A |
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $7,547 |
| Assessment | $573,900 |
Home facts updated by county records
Comparable Sales for 149 Chestnut St
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.45 | Single-Family Home | $795,000 | 11/24/25 | 4 | 3 | 2,536 | |
0.32 | Single-Family Home | $925,000 | 08/22/25 | 4 | 2.5 | 2,856 | |
0.31 | Single-Family Home | $600,000 | 12/12/25 | 3 | 2.5 | 1,732 | |
0.13 | Single-Family Home | $472,800 | 09/05/25 | 3 | 1.5 | 1,320 | |
0.60 | Single-Family Home | $1,500,000 | 05/07/26 | 4 | 3.5 | 3,586 | |
0.60 | Single-Family Home | $1,763,100 | 04/24/26 | 4 | 4.5 | 3,609 | |
0.78 | Single-Family Home | $885,000 | 06/20/25 | 5 | 2.5 | 3,568 | |
0.67 | Single-Family Home | $1,327,090 | 07/11/25 | 4 | 4.5 | 3,900 | |
1.08 | Single-Family Home | $710,000 | 07/11/25 | 3 | 2 | 2,154 | |
0.81 | Single-Family Home | $918,000 | 09/11/25 | 4 | 4 | 4,815 |
Assigned Schools
These are the assigned schools for 149 Chestnut St.
- Nipmuc Regional High School
- 9-12
- Public
- 475 Students
6/10GreatSchools RatingParent Rating AverageI am am currently a current freshmen here (going to sophomore next yr) in all honesty the school is good it’s just the concept of portrait of a learner which is being taught in a class at freshmen seminar. That concept comes from experiences and NOT FROM OTHERS experiences or cannot BE TAUGHT in a classroom. It’s also utterly useless. Another thing is that the Cafeteria in the school is not very accommodating to people who are lacto vegetarian (meaning that your not vegan but you don’t eat egg, meat, and any kind of non veg food) so a lot of the times all they serve is salad and chicken or any meat for the main lunch. I used to go to westborough middle school and they had options way more than the school district here. Another thing is they don’t offer much classes to freshmen and sophomore year I don’t know why but they don’t. Also, as a south Asian I didn’t really find much Asians or any other race except for white (not being racist) it’s kind of hard to make friends here and everyone’s in their own little friend circle. I found out that this school is REALLY hard to make new clubs, change some stuff, and get principles to actually listen to your ideas while they keep indirectly saying how nice this school is. I wanted to make more clubs but found it really hard to since 1.) I don’t know why but they refrain from sending out google forms and 2.) you need a lot of people. In my old school in westborough you only needed like 3 or 4 people to make a club and a teacher, but here it’s very complicated. There’s a lot of things at this school that REALLY needs to be developed. I would recommend it here but not really..I mean I’d recommend westborough high school instead of here. Also majority of the students here are wannabes. I really hope that the principles actually do something and USE their school funds to MAKE the school better. As I said there are WAY better school districts but if you want to go to a less populated and less stressed school and more none diverse oriented then this is your best bet.Student Review1y ago - Memorial School
- PK-4
- Public
- 456 Students
9/10GreatSchools RatingParent Rating Average0/10 that are the worst I am not going there ever again, I am moving on to westborough schools and pray they aren’t as bad as this one, over all I had a terrible experienceParent Review7y ago - Miscoe Hill School
- 5-8
- Public
- 678 Students
6/10GreatSchools RatingParent Rating AverageHorrible food bad teaching eceryone is burned out and lots of bullying and the teachers dont help and punish u when u fight backStudent Review4mo ago 
Check out schools near 149 Chestnut St.
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
Learn more about our methodology.
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Homes for rent near 149 Chestnut St
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Off Market Homes Near 149 Chestnut St
- SOLDMAY 8, 2026Sharada Kunam, Foemmel Fine Homes
- SOLDMAY 8, 2026Dalia Barron, Coldwell Banker Realty - Canton
- SOLDMAY 8, 2026Robyn Nasuti, Realty ONE Group Suburban Lifestyle
- SOLDMAY 7, 2026David Restic, Property Services Network
- SOLDMAY 4, 2026Robert W. Ross, Realty Executives Boston West
- SOLDMAY 4, 2026Lioce Properties Group, Lamacchia Realty, Inc.
- SOLDMAY 1, 2026Lisa Bailey, Berkshire Hathaway HomeServices Evolution Properties
- SOLDAPR 30, 2026Marcia Pessanha, eXp Realty
- SOLDAPR 30, 2026Michelle Faust, Streamline Communities - Franklin
- SOLDAPR 30, 2026Marcie Rappa, Better Living Real Estate, LLC
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149 Chestnut St, Upton, MA 01568 is a 4 bedroom, 3 bathroom, 2,252 sqft single-family home built in 1973. This property is not currently available for sale. 149 Chestnut St was last sold on Jul 6, 2021 for $540,000. The current Trulia Estimate for 149 Chestnut St is $712,000.