22 Pleasant St, Dover, MA 02030
OFF MARKET

22 Pleasant St
Dover, MA 02030

  • 5 Beds
  • 3.5 Baths
  • 3,622 sqft (on 2.78 acres)

$2,262,300

Trulia Estimate
as of Jun 18, 2026
Est. Refi. Payment $13,236/mo*
Refinance Your Home

$2,262,300

Trulia Estimate
as of Jun 18, 2026
Est. Refi. Payment $13,236/mo*
Refinance Your Home
5 Beds
3.5 Baths
3,622 sqft
(on 2.78 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

Quintessential New England Colonial beautifully updated and set on nearly 3 acres in desirable area close to both South Natick and Wellesley centers. This classic Colonial, beautifully set back from the street in private park-like setting, offers expansive well proportioned rooms, formal living and dining rooms, fireplaced family room off eat-in kitchen, 1st floor office, and 5 bedrooms including generously sized master with fireplace. Scenic stone walls and 3 car garage complete this very special 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.

Home Highlights

Parking
Garage
Outdoor
Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 22 Pleasant St

Interior Features

Interior Details
BasementNumber of Rooms: 10Types of Rooms: Walk In Closet, Breakfast Nook, Dining Room, Family Room, Laundry Room, Master Bath, Mud Room, Office
Heating & Cooling
Heating: Baseboard, OilAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood, Slate
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: WoodLawn
Parking & Garage
GarageParking Spaces: 3Parking: Garage Detached

Property Information

Year Built
Year Built: 1968Year Updated: 2016
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 2.78 acres

Building

Fitness & Sports
Basketball Court

Price History for 22 Pleasant St

DatePriceEventSource
09/08/2009$1,056,250Sold
N/A
03/28/2009$1,195,000PriceChange
Agent Provided
01/13/2009$1,395,000Listed For SaleAgent Provided
12/06/2008$1,395,000ListingRemovedAgent Provided
09/13/2008$1,395,000Listed For SaleAgent Provided
05/15/2003$452,000Sold
N/A

Market trends in Dover

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
39
11MoM
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Property Tax and Assessment

Year2025
Tax$21,263
Assessment$1,886,700
Home facts updated by county records

Homeowner tools

Estimated monthly rent$7,140/mo
List your home for rent

Comparable Sales for 22 Pleasant St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
60 Main St, Dover, MA
0.18
Single-Family Home
$1,650,000
11/13/25
4
3.5
3,233
8 Pleasant St, Dover, MA
0.16
Single-Family Home
$1,750,000
08/28/25
4
4
5,390
40 Pleasant St, Dover, MA
0.17
Single-Family Home
$2,400,000
09/12/25
6
5.5
5,150
42 Main St, Dover, MA
0.31
Single-Family Home
$1,300,000
05/18/26
3
2
2,276
91 Glen St, Natick, MA
0.78
Single-Family Home
$1,000,000
02/17/26
5
3
4,040
55 Main St, Dover, MA
0.25
Single-Family Home
$3,000,000
09/19/25
5
6.5
6,538
42 Troutbrook Rd, Dover, MA
0.53
Single-Family Home
$1,280,000
05/22/26
4
2.5
2,565
12 Cranberry Ln, Dover, MA
0.61
Single-Family Home
$1,395,000
01/16/26
4
2.5
4,245
19 Main St, Dover, MA
0.48
Single-Family Home
$1,380,000
11/03/25
3
2
2,442
76 Pleasant St, Natick, MA
0.57
Single-Family Home
$980,000
11/20/25
3
2.5
2,206

Nearby homes

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Assigned Schools

These are the assigned schools for 22 Pleasant St.
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 Dover

At least 16 Trulia users voted on each feature.

  • 100 % Say there's holiday spirit

  • 100 % Say car is needed

  • 96 % Say parking is easy

  • 95 % Say there's wildlife

  • 94 % Say yards are well-kept

  • 90 % Say it's dog friendly

  • 89 % Say it's quiet

  • 89 % Say people would walk alone at night

  • 76 % Say they plan to stay for at least 5 years

  • 74 % Say neighbors are friendly

  • 71 % Say there are community events

  • 67 % Say kids play outside

  • 28 % Say it's walkable to grocery stores

  • 25 % Say it's walkable to restaurants

  • 21 % Say streets are well-lit

  • 20 % Say there are sidewalks

Sourced by Trulia users. Learn more about our methodology.
  • James T.
    "The fresh air due to the abundant amount green space, property size and highest rated high school..."
    4
    Flag
  • Jaymz N.
    "Dover is visually beautiful but not a place to live if you are looking for thriving community of shops and restaurants. We only live here to access great public schools. "
    0
    Flag
  • Robin B.
    "I loved visiting my Aunt and Uncle in their beautiful well kept rustic home on this property the few occasions I had to visit my home state. I love the new home even though it is weird for me to imagine that being the property with all of the beautiful trees I had visited. When I was in Dover the whole area was beautiful and safe feeling. It held a lot of my families history. I am not rich, I am disabled and still in my 40's so I probably won't be getting rich but if I were to win tonight's Florida Mega ball I would buy this home and keep it in my family forever, even if I did need to return to Florida during the winter. I love that the area is clean, safe, quiet, and animal friendly, I know at one time a lot of people had horses, one of my aunt's neighbors had sheep, and according to my mom my grandfather had his horses in a nearby stable, he was in the English Hunt Club, I don't have many details about that, My Aunt had a Basset Hound "Ruby" when I was there as a teenager, me and Ruby had found one of my cousins old softballs while roaming in the woods from when they were kids in that home. Ruby tore it up all over the living room and I had to clean it up but it was great fun, that was the only time I got to meet Ruby in her life. I have to mixed breed dogs and if I lived there I would definitely get a horse. I did inherit my families love of animals. I feel that whomever gets this home or any in the area will have a lifetime of priceless memories. "
    5
    Flag
  • lydiaaustin7
    "I live here. It is an open and wooded area, It is fairly remote, but it is a very nice small community. "
    0
    Flag
  • Mary C.
    "Dover MA is the most wonderful town with their #1 School System, great town services, low tax rate, proximity to Boston, safety and cleanliness of the town!"
    0
    Flag

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Apartments for Rent

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Homes for sale near 22 Pleasant St

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Off Market Homes Near 22 Pleasant St

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22 Pleasant St, Dover, MA 02030 is a 5 bedroom, 4 bathroom, 3,622 sqft single-family home built in 1968. This property is not currently available for sale. 22 Pleasant St was last sold on Sep 8, 2009 for $1,056,250. The current Trulia Estimate for 22 Pleasant St is $2,262,300.