21 Trailside Rd, Medfield, MA 02052
OFF MARKET

21 Trailside Rd
Medfield, MA 02052

  • 4 Beds
  • 6 Baths
  • 3,490 sqft (on 1 acre)

$1,909,900

Trulia Estimate
as of Jun 23, 2026
Est. Refi. Payment $11,265/mo*
Refinance Your Home

$1,909,900

Trulia Estimate
as of Jun 23, 2026
Est. Refi. Payment $11,265/mo*
Refinance Your Home
4 Beds
6 Baths
3,490 sqft
(on 1 acre)

Local Information

  • Map ViewExplore the area around 21 Trailside Rd.
  • Schools2 Preschool Schools3 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

This single-family home is located at 21 Trailside Rd, Medfield, MA. 21 Trailside Rd is in Medfield, MA and in ZIP code 02052. This property has 4 bedrooms, 6 bathrooms and approximately 3,490 sqft of floor space. This property has a lot size of 1 acre and was built in 1994.
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, Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 21 Trailside Rd

Interior Features

Interior Details
BasementAtticIn-law unitNumber of Rooms: 14Wet BarCeiling Fan
Heating & Cooling
Heating: Forced Air, OilAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Appliances & Utilities
Cable Ready
Fireplace & Spa
FireplaceHot Tub or SpaJetted Bath Tub
Windows, Doors, Floors & Walls
Double Paned Windows
Security
Security System

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: WoodGardenLawnPatioSprinkler System
Pool
Pool
Parking & Garage
GarageParking Spaces: 3Parking: Garage Attached

Property Information

Year Built
Year Built: 1994Year Updated: 2008
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 1 acre

Price History for 21 Trailside Rd

DatePriceEventSource
08/22/2022$1,575,000Sold
MLS PIN #72968489
04/27/2022$1,599,000ContingentMLS PIN #72968489
04/20/2022$1,599,000Listed For SaleMLS PIN #72968489

Market trends in Medfield

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
37
1MoM
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Property Tax and Assessment

Year2025
Tax$21,143
Assessment$1,532,100
Home facts updated by county records

Comparable Sales for 21 Trailside Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
18 Birch Ln, Medfield, MA
0.19
Single-Family Home
$1,369,500
10/14/25
4
2.5
3,872
104 Wood End Ln, Medfield, MA
0.30
Single-Family Home
$1,355,000
04/01/26
4
3
2,933
32 Draper Rd, Dover, MA
0.79
Single-Family Home
$1,905,000
07/17/25
4
4
5,813
4 Sturbridge Rd, Medfield, MA
0.91
Single-Family Home
$2,200,000
03/31/26
4
4
4,171
17 Boyden Rd, Medfield, MA
0.74
Single-Family Home
$1,930,000
04/30/26
5
4
5,669
99 Hartford St, Medfield, MA
0.98
Single-Family Home
$1,615,000
06/18/26
5
4.5
4,904
42 Vine Brook Rd, Medfield, MA
0.91
Single-Family Home
$1,925,000
06/08/26
5
4
4,306
42 Hartford St, Dover, MA
0.78
Single-Family Home
$3,400,000
10/30/25
5
6.5
7,500
54 Wagon Rd, Walpole, MA
1.14
Single-Family Home
$1,450,000
11/14/25
5
4.5
6,353
16 Crest Dr, Dover, MA
1.31
Single-Family Home
$1,335,000
04/07/26
4
3.5
3,707

Nearby homes

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Assigned Schools

These are the assigned schools for 21 Trailside Rd.
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 Medfield

At least 39 Trulia users voted on each feature.

  • 93 % Say it's dog friendly

  • 89 % Say parking is easy

  • 88 % Say car is needed

  • 85 % Say yards are well-kept

  • 83 % Say it's quiet

  • 82 % Say kids play outside

  • 80 % Say people would walk alone at night

  • 79 % Say there's holiday spirit

  • 73 % Say neighbors are friendly

  • 65 % Say they plan to stay for at least 5 years

  • 64 % Say there's wildlife

  • 63 % Say there are sidewalks

  • 62 % Say there are community events

  • 47 % Say it's walkable to restaurants

  • 46 % Say streets are well-lit

  • 41 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Coneil702
    "Great location and walkable and close to the town center. New playground down the street and lots of families and kids."
    0
    Flag
  • Frank
    "Great town with great people. Kim’s friendly and welcoming. Good sense of community but large lots and good privacy. "
    1
    Flag
  • Jim_caro
    "Multiple times throughout the year the neighborhood gets together for enemy’s. More importantly everyone is friendly and looks after one another."
    3
    Flag
  • Bob I.
    "difficult to Boston, ok to other more local areas. rt 109 difficult thr5u Medfield. lacks major connecor to Area highways."
    3
    Flag
  • Kieron
    "Very safe neighborhood. Lots of space in many areas A little further out from 95 than say Wellesley or Natick but the balance is a quieter area"
    0
    Flag
  • hughsenergy
    "We went to a block party at this home and it was a great time. Lots of kids in the neighborhood. Everyone takes excellant care of their homes."
    0
    Flag
  • The W. T.
    "Having been a resident in Medfield since 2002, I can say without question it is a fantastic place to live! There are so many area amenties, yet Medfield hasn't lost that small town feel. People are friendly and outgoing and they are completely vested in the community. There is great dining, a premier Health/Tennis Club, as well as a School System that is Nationally recognized. Ask anyone who lives here, Medfield is a tough place to leave but you will always feel welcome when you come back! I couldn't be happier living here."
    2
    Flag
  • Marie Z.
    "I live & work in Medfield. This neighborhood is a mix of every style home and price range. It has sidewalks, 2 entrances into n'hood & loops around 2 streets great for walking with dogs, strollers, kids on bikes, etc.. There are approx 60 homes and over 29+ kids from newborn to HS. An easy walk to town and safe. An active n'hood with annual block parties, girls and men nite out, Halloween parades, etc.. "
    0
    Flag
  • Alison B.
    "This is a great area to live - easy commuting area - this in particular has beautiful views of the Charles River - is a perfect area for young families - great schools, and very beautiful town center with restaurants, new library and new town hall! Schools are award winning!"
    0
    Flag
  • Alison B.
    "Not only is Medfield a wonderful town to raise a family, superior schools, beautiful New England Town Center plus easy to commute into both Boston and Providence area. You do not need to travel far for 4 star restaurants, Charles River runs through town - creating great sporting for those who fish, kyack and canoe, Noon Hill Reservation as well as Rocky Woods Reservations offers wonderful walking/hiking trails as well as perfect mountain bike trails - a hidden gem!"
    1
    Flag

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21 Trailside Rd, Medfield, MA 02052 is a 4 bedroom, 6 bathroom, 3,490 sqft single-family home built in 1994. This property is not currently available for sale. 21 Trailside Rd was last sold on Aug 22, 2022 for $1,575,000. The current Trulia Estimate for 21 Trailside Rd is $1,909,900.