21 Pleasant St, Dover, MA 02030
Property image
Property image
OFF MARKET

21 Pleasant St
Dover, MA 02030

  • 4 Beds
  • 5 Baths
  • 5,500 sqft (on 1 acre)

$2,975,400

Trulia Estimate
as of Jul 4, 2026
Est. Refi. Payment $17,260/mo*
Refinance Your Home

$2,975,400

Trulia Estimate
as of Jul 4, 2026
Est. Refi. Payment $17,260/mo*
Refinance Your Home
4 Beds
5 Baths
5,500 sqft
(on 1 acre)

Local Information

  • Map ViewExplore the area around 21 Pleasant St.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Flexible Rental Period
21 Pleasant St, Dover, MA 02030 is a 4 bedroom, 5 bathroom, 5,500 sqft single-family home built in 2007. It last sold for $1,750,000 on Jul 10, 2015. More recently, it was listed as a rental in June 2015 with an asking price of $5,700 per month. That rental listing was removed on March 24, 2021. It is currently off market. The Trulia Estimate is $2,975,400, with a rent estimate of $7,893/month.

Home Highlights

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

Home Details for 21 Pleasant St

Interior Features

Interior Details
BasementNumber of Rooms: 14
Heating & Cooling
Heating: Forced Air, OilAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 2007
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 1 acre

Price History for 21 Pleasant St

DatePriceEventSource
03/24/2021ListingRemovedN/A
09/09/2015$5,300ListingRemovedN/A
08/12/2015$5,300PriceChange
N/A
07/10/2015$1,750,000Sold
N/A
06/20/2015$5,700Listed For RentN/A
01/20/2015$1,894,000PriceChange
Agent Provided
09/03/2014$1,994,000PriceChange
Agent Provided
05/23/2014$2,194,000PriceChange
Agent Provided
03/17/2014$2,250,000Listed For SaleAgent Provided
07/24/2008$1,932,036Sold
N/A
02/21/2008$2,199,000Listed For SaleAgent Provided
12/20/2006$420,000Sold
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$25,977
Assessment$2,305,000
Home facts updated by county records

Comparable Sales for 21 Pleasant St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
8 Pleasant St, Dover, MA
0.17
Single-Family Home
$1,750,000
08/28/25
4
4
5,390
60 Main St, Dover, MA
0.11
Single-Family Home
$1,650,000
11/13/25
4
3.5
3,233
7 Circle Dr, Dover, MA
0.53
Single-Family Home
$2,275,000
08/13/25
4
5.5
5,216
22 Main St, Dover, MA
0.45
Single-Family Home
$2,150,000
04/21/26
5
4.5
5,232
40 Pleasant St, Dover, MA
0.20
Single-Family Home
$2,400,000
09/12/25
6
5.5
5,150
6 Meadowbrook Rd, Dover, MA
0.55
Single-Family Home
$2,675,000
08/18/25
5
5
5,900
5 Pegan Ln, Natick, MA
0.31
Single-Family Home
$3,100,000
06/18/26
5
5
6,952
42 Troutbrook Rd, Dover, MA
0.46
Single-Family Home
$1,280,000
05/22/26
4
2.5
2,565
12 Cranberry Ln, Dover, MA
0.60
Single-Family Home
$1,395,000
01/16/26
4
2.5
4,245
55 Main St, Dover, MA
0.18
Single-Family Home
$3,000,000
09/19/25
5
6.5
6,538

Nearby homes

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Assigned Schools

These are the assigned schools for 21 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 21 Pleasant St

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Off Market Homes Near 21 Pleasant St

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