20 Jackson Rd
Sherborn, MA 01770
5 Beds
3.5 Baths
4,932 sqft (on 4.45 acres)
5 Beds
3.5 Baths
4,932 sqft
(on 4.45 acres)
Local Information
© Google
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Description
Welcome to Apple Tree Acres! This exceptional 4+ acre property has been thoughtfully updated and expanded. The first floor features a gourmet kitchen with high end appliances, granite counters and a large island with seating. A formal dining room, great room with stone f/p and wet bar, home office with built-ins and addtl family room with f/p and custom cabinets. Radiant floored mudroom, 1/2 bath & separate laundry room finish off the floor. Second floor includes an ensuite bedroom and 3 addtl bedrooms with hardwoods throughout.The primary suite features a sitting area, walk-in custom closets, spa like bath with radiant floors and balcony overlooking the expansive yard. Partial finished basement w/ plenty of storage completes the main house. Outside enjoy the heated pool, hot tub, outdoor shower and pool house complete with kitchen, built-in storage & 1/2 bath. The Caldwell 4 stall barn with tack room, electricity and water completes the property. Don't miss this idyllic property!
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. This description is from November 15, 2023
Home Highlights
Parking
3 Car Garage
Outdoor
Porch, Patio, Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
146 days ago
Home Details for 20 Jackson Rd
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Interior Details Basement: Partial,Partially Finished,Interior Entry,Bulkhead,Sump PumpNumber of Rooms: 11Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 5, Master Bathroom, Bathroom 1, Bathroom 2, Bathroom 3, Dining Room, Kitchen, Living Room, OfficeWet Bar |
Beds & Baths Number of Bedrooms: 5Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1 |
Dimensions and Layout Living Area: 4932 Square Feet |
Appliances & Utilities Utilities: for Gas Range, for Electric Oven, for Electric Dryer, Washer Hookup, Generator Connection, Outdoor Gas Grill HookupAppliances: Gas Water Heater, Water Heater, Range, Oven, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer, Wine Refrigerator, Range Hood, Water SoftenerDishwasherDisposalDryerLaundry: Flooring - Stone/Ceramic Tile,Main Level,Lighting - Overhead,Sink,First Floor,Electric Dryer Hookup,Washer HookupMicrowaveRefrigeratorWasher |
Heating & Cooling Heating: Forced Air,Natural Gas,FireplaceHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air |
Fireplace & Spa Number of Fireplaces: 2Fireplace: Living RoomSpa: PrivateHas a FireplaceHas a Spa |
Gas & Electric Electric: Generator Connection |
Windows, Doors, Floors & Walls Window: ScreensDoor: French DoorsFlooring: Tile, Hardwood, Stone / Slate, Vinyl / VCT, Flooring - Hardwood, Flooring - Stone/Ceramic Tile, Flooring - Vinyl |
Levels, Entrance, & Accessibility Floors: Tile, Hardwood, Stone Slate, Vinyl VCT, Flooring Hardwood, Flooring Stone Ceramic Tile, Flooring Vinyl |
Security Security: Security System |
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Exterior Home Features Roof: ShinglePatio / Porch: Porch, PatioFencing: Fenced/Enclosed, Fenced, InvisibleOther Structures: Cabana, Barn/StableExterior: Porch, Patio, Balcony, Pool - Inground Heated, Cabana, Rain Gutters, Hot Tub/Spa, Storage, Barn/Stable, Professional Landscaping, Sprinkler System, Decorative Lighting, Screens, Fenced Yard, Fruit Trees, Invisible Fence, Outdoor Shower, Stone Wall, Outdoor Gas Grill HookupFoundation: Concrete PerimeterHas a Private PoolSprinkler System |
Parking & Garage Number of Garage Spaces: 3Number of Covered Spaces: 3Open Parking Spaces: 6No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 9Parking: Attached,Garage Door Opener,Heated Garage,Storage,Workshop in Garage,Garage Faces Side,Paved Drive,Paved |
Pool Pool: Pool - Inground HeatedPool |
Frontage Road Frontage: PublicResponsible for Road Maintenance: Public Maintained RoadRoad Surface Type: PavedNot on Waterfront |
Water & Sewer Sewer: Private Sewer |
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Year Built Year Built: 1971 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial |
Building Construction Materials: FrameAttached To Another StructureDoes Not Include Home Warranty |
Property Information Not Included in Sale: Blink Cameras-Negotiable, Draperies In Office Excluded But Hardware Will StayParcel Number: M:0004 B:0000 L:9, 741312 |
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Price List Price: $2,095,000 |
Status Change & Dates Off Market Date: Sat Sep 16 2023 |
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MLS Status: Sold |
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Direction & Address City: Sherborn |
School Information Elementary School: Pine HillJr High / Middle School: Dover-SherbornHigh School: Dover-Sherborn |
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Building Area Building Area: 4932 Square Feet |
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Community Features: Shopping, Walk/Jog Trails, Stable(s), Conservation AreaNot Senior Community |
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No HOA |
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Lot Area: 4.45 Acres |
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BasementMls Number: 73158411 |
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ShoppingWalk/Jog TrailsStable(s)Conservation Area |
Last check for updates: about 2 hours ago
Listed by Amy Caffrey, (508) 479-4542
Compass, (781) 365-9954
Amy Caffrey, (508) 479-4542
Bought with: The Powissett Group, (508) 294-9318, Compass, (781) 365-9954
Source: MLS PIN, MLS#73158411
Price History for 20 Jackson Rd
| Date | Price | Event | Source |
|---|---|---|---|
| 11/15/2023 | $2,150,000 | Sold | MLS PIN #73158411 |
| 09/12/2023 | $2,095,000 | Listed For Sale | MLS PIN #73158411 |
| 10/05/1994 | $510,000 | Sold | N/A |
| 07/30/1992 | $340,000 | Sold | N/A |
Market trends in Sherborn
Last updated May 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
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Available listings
25
4MoM
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $32,646 |
| Assessment | $1,969,000 |
Home facts updated by county records
Homeowner tools
Estimated monthly rent$6,613/mo
Comparable Sales for 20 Jackson Rd
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.18 | Single-Family Home | $1,400,000 | 11/12/25 | 4 | 3.5 | 4,184 | |
0.64 | Single-Family Home | $1,440,000 | 07/01/25 | 3 | 3.5 | 3,525 | |
0.90 | Single-Family Home | $1,800,000 | 08/26/25 | 4 | 2.5 | 3,878 | |
1.19 | Single-Family Home | $1,725,000 | 11/14/25 | 4 | 3 | 4,047 | |
0.59 | Single-Family Home | $855,000 | 09/02/25 | 4 | 2.5 | 2,948 | |
0.97 | Single-Family Home | $1,250,000 | 05/01/26 | 4 | 3 | 4,130 | |
1.02 | Single-Family Home | $1,700,000 | 06/26/25 | 5 | 3.5 | 3,648 | |
0.85 | Single-Family Home | $944,000 | 12/10/25 | 4 | 4 | 3,775 | |
1.17 | Single-Family Home | $1,392,000 | 06/08/26 | 5 | 3 | 3,938 | |
1.07 | Single-Family Home | $925,000 | 03/13/26 | 3 | 3 | 3,484 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
SOLDNOV 12, 2025Laura Mastrobuono, Compass
OFF MARKETRobin Spangenberg, Redfin Corp.
OFF MARKETDan Young, Realty Executives Boston West
OFF MARKETBeatriz Gomez, Century 21 North East
FOR SALE
3D VIEW3.01 ACRESThe Powissett Group, Compass
SOLDSEP 19, 2025The Walsh Team & Partners, William Raveis R.E. & Home Services
FOR SALE1.6 ACRESThe Lara & Chelsea Collaborative, Coldwell Banker Realty - Wellesley
OFF MARKETThe Kattman Team, Berkshire Hathaway HomeServices Commonwealth Real Estate
SOLDNOV 20, 2025Joshua Shalin, ERA Key Realty Services-Bay State Group
SOLDNOV 17, 2025The Powissett Group, Compass
Assigned Schools
These are the assigned schools for 20 Jackson Rd.
- Pine Hill Elementary School
- PK-5
- Public
- 393 Students
8/10GreatSchools RatingParent Rating AverageI am really surprised by the negative reviews below. I can't help but wonder if the last one was written out of anger over the changing elementary school start times. While it is not true that the school does not have a second emergency access road (it does) and not true that children can't talk to each other at lunch (they can) I am most surprised by the categorization of the school leadership. I have never met a more phenomenal principal, and between my kids and multiple moves we have been at seven elementary schools. I have experienced nothing but warmth and a true dedication to educating all children inclusively.Parent Review5y ago - Dover-Sherborn Regional High School
- 9-12
- Public
- 613 Students
10/10GreatSchools RatingParent Rating AverageDover-Sherborn High School is exceptional in academics and has faculty that genuinely care about the students. And while the education is rigorous, the opportunity for the students to learn more about areas the are interested in is always available. I appreciate the hard work the administration did to keep the kids in school during the pandemic. And, as a parent of a child who learns differently, the school has helped her not feel out of place while ensuring she gets the most of her secondary school education. The school has a no tolerance policy on bullying. Very excited to see what the next chapter brings with a new district superintendent that came from Boston Latin.Parent Review4y ago - Dover-Sherborn Regional Middle School
- 6-8
- Public
- 459 Students
8/10GreatSchools RatingParent Rating AverageBoth my children are Dover-Sherborn Regional Middle School students. I loved their teachers. They made my kids feel very welcome and helped with their curriculum. My daughter is in advanced program in high school and all the foundation was from Dover-Sherborn Regional Middle School. Above all, the teachers are very much dedicated and put their time and effort for the children. They addressed all my concerns immediately. This is really a lovely school for the Dover-Sherborn community.Parent Review5y ago 
Check out schools near 20 Jackson Rd.
What Locals Say about Sherborn
At least 26 Trulia users voted on each feature.
93 % Say car is needed
92 % Say it's dog friendly
89 % Say yards are well-kept
88 % Say there's wildlife
83 % Say parking is easy
82 % Say there's holiday spirit
79 % Say people would walk alone at night
66 % Say neighbors are friendly
62 % Say it's quiet
60 % Say they plan to stay for at least 5 years
59 % Say kids play outside
55 % Say there are community events
47 % Say there are sidewalks
19 % Say streets are well-lit
17 % Say it's walkable to restaurants
14 % Say it's walkable to grocery stores
Sourced by Trulia users. Learn more about our methodology.
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Apartments for Rent
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Homes for sale near 20 Jackson Rd
- 3.01 ACRESThe Powissett Group, Compass
- 1.6 ACRESThe Lara & Chelsea Collaborative, Coldwell Banker Realty - Wellesley
3.55 ACRESVesta Group, Vesta Real Estate Group, Inc.
3 ACRESThe Madden David Real Estate Group, Coldwell Banker Realty - Wellesley
2.25 ACRESSusan McPherson, Berkshire Hathaway HomeServices Commonwealth Real Estate
OPEN SAT, 2-3:30PM0.9 ACRESSharada Kunam, Foemmel Fine Homes
See more homes for sale inSherborn
Off Market Homes Near 20 Jackson Rd
SOLDJUN 15, 2026The Atwood Scannell Team, Dover Country Properties Inc.
SOLDJUN 11, 2026The Bohlin Group, Compass
SOLDJUN 10, 2026Laura Mastrobuono, Compass
SOLDJUN 10, 2026Laura Mastrobuono, Compass
SOLDJUN 10, 2026The Powissett Group, Compass
SOLDJUN 9, 2026Danielle Marino, Berkshire Hathaway HomeServices Commonwealth Real Estate
SOLDJUN 8, 2026Nora Lynch, Gibson Sotheby's International Realty
SOLDJUN 5, 2026Faina Shapiro, Berkshire Hathaway Home Services Commonwealth Real Estate
SOLDJUN 4, 2026Candice Beecher, Berkshire Hathaway HomeServices Commonwealth Real Estate
SOLDJUN 1, 2026Kandi Pitrus, Berkshire Hathaway HomeServices Commonwealth Real Estate- See more homes for sale inSherborn
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.
The MLS listing information displayed is deemed reliable, but is not guaranteed accurate by the MLS.
20 Jackson Rd, Sherborn, MA 01770 is a 5 bedroom, 4 bathroom, 4,932 sqft single-family home built in 1971. This property is not currently available for sale. 20 Jackson Rd was last sold on Nov 15, 2023 for $2,150,000 (3% higher than the asking price of $2,095,000). The current Trulia Estimate for 20 Jackson Rd is $2,271,800.