21 Trailside Rd, Medfield, MA 02052
Property image
Property image
OFF MARKET

$1,881,300

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

21 Trailside Rd, Medfield, MA 02052

Est. Refi. Payment $11,246/mo*
Refinance Your Home
Currently Off Market - Sold Aug 22, 2022 for $1,575,000

Home Value

Trulia Estimate
$1.88M
Since last month
Decreased$22K (-1.2%)
Since last year
Increased$83K (+4.6%)
Since last sale
Increased$308K (+19.6%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +69% in the last 10 years
MonthEstimated value
2026
August 2026$1.88M
August 2026$1.88M
July 2026$1.91M
June 2026$1.89M
May 2026$1.91M
April 2026$1.88M
March 2026$1.87M
February 2026$1.81M
January 2026$1.78M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
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
86 Wood End Ln, Medfield, MA
0.22
Single-Family Home
$1,150,000
07/30/26
4
2.5
3,182
104 Wood End Ln, Medfield, MA
0.30
Single-Family Home
$1,355,000
04/01/26
4
3
2,933
12 Birch Ln, Medfield, MA
0.23
Single-Family Home
$1,850,000
07/09/26
5
3.5
5,507
7 Crest Cir, Medfield, MA
0.78
Single-Family Home
$1,575,000
07/30/26
4
3.5
4,450
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

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
23 Trailside Rd, Medfield, MA 02052
0.04
$1,688,000
4
3.5
4,513
Off Market
17 Trailside Rd, Medfield, MA 02052
0.04
$1,749,700
5
3.5
4,368
Off Market
70 Main St, Medfield, MA 02052
0.15
$2,234,500
7
5.5
5,048
Off Market
80 Wood End Ln, Medfield, MA 02052
0.19
$1,336,900
4
2.5
3,207
Off Market
70-74 Main St, Medfield, MA 02052
0.18
-
7
5.5
5,048
Off Market
18 Birch Ln, Medfield, MA 02052
0.19
$1,519,300
4
2.5
3,872
Off Market
86 Wood End Ln, Medfield, MA 02052
0.22
$1,150,000
4
2.5
3,182
Recently Sold
2 Trailside Rd, Medfield, MA 02052
0.21
$1,349,600
4
2.5
3,714
Off Market
80 Main St, Medfield, MA 02052
0.22
$1,579,000
4
2.5
3,178
Off Market
92 Wood End Ln, Medfield, MA 02052
0.25
$1,000,100
3
2.5
1,971
Off Market
12 Birch Ln, Medfield, MA 02052
0.23
$1,850,000
5
3.5
5,507
Recently Sold
104 Wood End Ln, Medfield, MA 02052
0.30
$1,355,000
4
3
2,933
Recently Sold

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

Home Highlights

Single-Family Home
Built in 1994
1 acre lot
3,490 sqft
$539/sqft
Garage

About this House

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.
21 Trailside Rd, Medfield, MA 02052 is a 4 bedroom, 6 bathroom, 3,490 sqft single-family home built in 1994. It last sold for $1,575,000 on Aug 22, 2022. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,881,300, with a rent estimate of $7,758/month.

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 and Tax history

DateEventPrice
Aug 22, 2022
Source: MLS PIN #72968489
Sold
$1,575,000
Apr 27, 2022
Source: MLS PIN #72968489
Contingent
$1,599,000
Apr 20, 2022
Source: MLS PIN #72968489
Listed For Sale
$1,599,000

Market trends in Medfield

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.08M
Sale-to-List Price
101.9%
Price per sq ft
$422
Available listings
21
9MoM

Around this home

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

  • 62 % Say there are sidewalks

  • 61 % Say there are community events

  • 48 % Say it's walkable to restaurants

  • 45 % Say streets are well-lit

  • 41 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Frank
    "Great neighborhood "
    0
    Flag
  • 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

LGBTQ Local Legal Protections

Frequently asked questions about 21 Trailside Rd

  • What is 21 Trailside Rd estimated to be worth?
    Trulia's estimated value for 21 Trailside Rd in Medfield, MA is $1,881,300.
  • What is the price history for 21 Trailside Rd?
    21 Trailside Rd in Medfield, MA last sold for $1,575,000 in August 2022.
  • Is Medfield a buyer's or seller's market?
    Medfield is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Medfield?
    The median sale price in Medfield is $1.08M.
  • Does 21 Trailside Rd have a pool?
    Yes, 21 Trailside Rd in Medfield, MA has a pool.
  • How big is the lot at 21 Trailside Rd?
    The lot at 21 Trailside Rd in Medfield, MA is about 1 acre (43,486 sq ft).

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Off Market Homes Near 21 Trailside Rd

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