OFF MARKET

Off Market Aug 2022 for $1.5M

$1,735,984

•

3,800

sq ft

21 Trailside Rd, Medfield, MA 02052

About this home

This stunning home was masterfully conceived to showcase magnificent grounds and a resort-like backyard for year-round enjoyment. Serve al fresco dinners in the gazebo or drinks at the poolside bar while guests swim by the waterfall, relax in the spa or practice on the putting green. French doors at the patio open to an elegant 2-story family room featuring a custom fireplace surround and breathtaking window wall designed to optimize the light and the view. Entertaining is easy in the kitchen w/mahogany cabinetry; professional integrated appliances; large island and bar; breakfast alcove and wainscoted dining room w/bay window. Down the hall past the office is a 1st floor primary suite boasting a luxurious bath w/soaking tub, marble shower & custom closets. Three additional bedrooms share 2 full baths while a 2nd staircase by the mudroom leads to a fabulous au pair/recreation room w/small kitchenette, full bath, closet & separate entrance. The ultimate in indoor-outdoor living!

Single-familyProperty Type

1994Year Built

1 acresLot Size

$457Est. Price/Sq.Ft.

3 garage spacesParking

Listed by Katherine Murray • Coldwell Banker Realty - Westwood

Bought with Katherine Murray • Coldwell Banker Realty - Westwood

Redfin checked: 2 minutes ago

•Source:MLS PIN #72968489

Redfin Estimate

$1,735,984

$161K since sold in August 2022$2,000 since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 7.8% higher than the average sale price ($1.61M) of 6 comparable homes.

SOLD APR 30, 2026
$1,930,000
A
5 beds4 baths5,669 sq ft
17 Boyden Rd, Medfield, MA 02052
SOLD JUL 29, 2026
$1,275,000
B
4 beds3.5 baths2,880 sq ft
4 Skyview Dr, Walpole, MA 02081
SOLD JUN 18, 2026
$1,615,000
C
5 beds4.5 baths4,904 sq ft
99 Hartford St, Medfield, MA 02052
SOLD JUL 9, 2026
$1,850,000
D
5 beds3.5 baths5,507 sq ft
12 Birch Ln, Medfield, MA 02052
SOLD JUL 30, 2026
$1,575,000
E
4 beds3.5 baths4,450 sq ft
7 Crest Cir, Medfield, MA 02052
SOLD JUN 29, 2026
$1,420,000
F
4 beds3.5 baths3,706 sq ft
18 Saddle Ridge Rd, Dover, MA 02030

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Earn from this home

Sell

$484,949

Est. take-home

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Rent

$4,398/mo

Redfin rental estimate

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Market trends in 02052, MA

Last updated July 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

103.1%

+0.5% MoM

Median sale price

$1.1M

$25K MoM

Avg. days on market

19d

1 days MoM

Recently sold homes

18 MoM

New listings for sale

OPEN SAT, 12PM TO 1:30PM
$999,000
4 beds2.5 baths2,550 sq ft
19 Snyder Rd, Medfield, MA 02052
$349,999
2 beds1 bath930 sq ft
91 Pleasant St Unit D1, Medfield, MA 02052
See all

Provided by Redfin

Sale history for 21 Trailside Rd

Year

Property tax

Land + Additions

Assessment*

2023

$18,339 (+2.0%)

$481,500 + $707,000

$1,188,500

2022

$17,986 (+1.4%)

$461,600 + $570,900

$1,032,500

2021

$17,739 (+1.3%)

$455,600 + $543,200

$998,800

2020

$17,504 (−0.5%)

$453,600 + $528,100

$981,700

2019

$17,586 (+6.2%)

$449,600 + $534,500

$984,100

2018

$16,555 (+1.2%)

$449,600 + $522,500

$972,100

2017

$16,351 (+0.8%)

$445,600 + $522,500

$968,100

2016

$16,216 (+7.9%)

$445,600 + $522,500

$968,100

2015

$15,034 (+2.3%)

$426,800 + $510,500

$937,300

2014

$14,703 (+6.2%)

$401,600 + $510,500

$912,100

2013

$13,844 (+0.8%)

$369,600 + $510,500

$880,100

2012

$13,739 (+3.3%)

$350,400 + $523,000

$873,400

2011

$13,299 (+3.1%)

$362,400 + $523,000

$885,400

2010

$12,893 (+4.1%)

$382,400 + $523,000

$905,400

2009

$12,382

$355,200 + $538,800

$894,000

Tax history for 21 Trailside Rd

Year

Property tax

Land + Additions

Assessment*

2023

$18,339 (+2.0%)

$481,500 + $707,000

$1,188,500

2022

$17,986 (+1.4%)

$461,600 + $570,900

$1,032,500

2021

$17,739 (+1.3%)

$455,600 + $543,200

$998,800

2020

$17,504 (−0.5%)

$453,600 + $528,100

$981,700

2019

$17,586 (+6.2%)

$449,600 + $534,500

$984,100

2018

$16,555 (+1.2%)

$449,600 + $522,500

$972,100

2017

$16,351 (+0.8%)

$445,600 + $522,500

$968,100

2016

$16,216 (+7.9%)

$445,600 + $522,500

$968,100

2015

$15,034 (+2.3%)

$426,800 + $510,500

$937,300

2014

$14,703 (+6.2%)

$401,600 + $510,500

$912,100

2013

$13,844 (+0.8%)

$369,600 + $510,500

$880,100

2012

$13,739 (+3.3%)

$350,400 + $523,000

$873,400

2011

$13,299 (+3.1%)

$362,400 + $523,000

$885,400

2010

$12,893 (+4.1%)

$382,400 + $523,000

$905,400

2009

$12,382

$355,200 + $538,800

$894,000

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

Baths

5.5

Stories

Lot width

—

Lot depth

—

Lot size

43,486

Year renovated

2025

Sq. Ft.

3,800

Year built

1994

Style

Single Family Residential

County

Norfolk County

APN

114726

Parking Spaces

Basement

Yes

Accessible

HOA Dues

—

Garage

Yes

Features

Green, Pool

Last updated by owner on Jun 14, 2025.

Property details

Parking

Parking Information
Has Garage
Has Open Parking
# of Garage Spaces: 3
# of Covered Spaces: 3
Parking Spaces: 8
AttachedGarageYN: Yes
Parking Features: Attached, Garage Door Opener, Garage Faces Side, Paved Drive, Off Street, Paved

Interior

Master Bedroom Information
Area: 195
Length: 13
Width: 15
Level: First
Features: Bathroom - Full,Ceiling Fan(s),Vaulted Ceiling(s),Walk-In Closet(s),Closet,Flooring - Hardwood,Window(s) - Picture

Bedroom #2 Information
Area: 182
Length: 13
Width: 14
Level: Second
Features: Closet,Flooring - Wall to Wall Carpet

Bedroom #3 Information
Area: 225
Length: 15
Width: 15
Level: Second
Features: Flooring - Wall to Wall Carpet,Closet - Double

Bedroom #4 Information
Area: 168
Length: 12
Width: 14
Level: Second
Features: Closet,Flooring - Wall to Wall Carpet

Bathroom Information
# of Bathrooms (Full): 4
# of Bathrooms (Half): 1
Master Bathroom Features: Yes

Bathroom #1 Information
Area: 112
Length: 14
Width: 8
Level: First
Features: Bathroom - Full,Bathroom - Tiled With Tub & Shower,Cathedral Ceiling(s),Flooring - Marble,Countertops - Stone/Granite/Solid,Cabinets - Upgraded,Double Vanity,Recessed Lighting,Remodeled,Wainscoting,Pocket Door,Soaking Tub

Bathroom #2 Information
Area: 64
Length: 8
Width: 8
Level: Second
Features: Bathroom - Full,Bathroom - With Shower Stall,Flooring - Stone/Ceramic Tile

Bathroom #3 Information
Area: 45
Length: 9
Width: 5
Level: Second
Features: Bathroom - Full,Bathroom - Tiled With Tub & Shower,Flooring - Stone/Ceramic Tile

Family Room Information
Area: 224
Length: 16
Width: 14
Level: First
Features: Vaulted Ceiling(s),Closet/Cabinets - Custom Built,Flooring - Hardwood,French Doors,Exterior Access,Open Floorplan,Recessed Lighting

Dining Room Information
Area: 208
Length: 13
Width: 16
Level: First
Features: Flooring - Hardwood,Window(s) - Bay/Bow/Box,Wainscoting,Crown Molding

Kitchen Information
Area: 280
Length: 20
Width: 14
Level: First
Features: Flooring - Hardwood,Window(s) - Bay/Bow/Box,Dining Area,Countertops - Stone/Granite/Solid,Kitchen Island,Breakfast Bar / Nook,Cabinets - Upgraded,Open Floorplan,Recessed Lighting,Remodeled,Stainless Steel Appliances,Wine Chiller,Gas Stove,Crown Molding

Office Room Information
Area: 192
Length: 12
Width: 16
Level: First
Features: Flooring - Hardwood,Window(s) - Bay/Bow/Box,French Doors,Recessed Lighting,Crown Molding

Basement Information
Basement: Full, Interior Entry, Sump Pump

Laundry Information
Laundry Features: Dryer Hookup - Electric, Washer Hookup, Electric Dryer Hookup, First Floor

Fireplace Information
Has Fireplace
# of Fireplaces (Total): 1
Fireplace Features: Family Room

Interior Features
# of Rooms (Total): 10
Door Features: French Doors, Insulated Doors
Window Features: Window(s) - Bay/Bow/Box, Window(s) - Picture, Insulated Windows, Screens
Flooring: Tile, Carpet, Marble, Hardwood, Flooring - Hardwood, Flooring - Stone/Ceramic Tile
Interior Features: Recessed Lighting, Crown Molding, Cathedral Ceiling(s), Beamed Ceilings, Walk-In Closet(s), Open Floorplan, Lighting - Sconce, Dining Area, Countertops - Stone/Granite/Solid, Wet Bar, Bathroom - With Shower Stall, Beadboard, Closet - Double, Bathroom - Half, Office, Bonus Room, Kitchen, Bathroom, Mud Room, Wet Bar, Wired for Sound, High Speed Internet, Other

Exterior

Building Information
Building Area (Total): 3,800
Foundation Details: Concrete Perimeter
Construction Materials: Frame
Year Built Source: Owner
Year Built Details: Renovated Since
Color: Taupe

Exterior Features
Fencing: Fenced/Enclosed, Fenced
Roof: Shingle
Patio And Porch Features: Patio
Exterior Features: Patio, Pool - Inground Heated, Cabana, Rain Gutters, Hot Tub/Spa, Storage, Professional Landscaping, Sprinkler System, Decorative Lighting, Screens, Fenced Yard, Gazebo, Garden, Outdoor Shower, Stone Wall

Pool Information
Has Private Pool
Has Spa
Pool Features: Pool - Inground Heated
Spa Features: Private

Property Information
PropertySubType: Single Family Residence
Green Energy Efficient : Thermostat
Green Energy Generation: Solar
Security Features: Security System
Other Structures: Cabana, Gazebo

Lot Information
Lot Size (Acres): 1
Lot Features: Cul-De-Sac, Wooded, Easements, Level
Road Frontage Type: Public
Road Responsibility: Public Maintained Road

Financial

Tax Information
Tax Annual Amount: $17,986
Tax Year: 2022

Utilities

Utility Information
Utilities: for Gas Range, for Electric Oven, for Electric Dryer, Washer Hookup, Icemaker Connection
Sewer: Public Sewer
Water Source: Public
Electric: Circuit Breakers, 200+ Amp Service, Other (See Remarks)

Heating & Cooling
Has Heating
Has Cooling
Heating: Forced Air, Oil
Cooling: Central Air

Location

Location Information
Directions: Rt 109 to Trailside Rd, a cul-de-sac neighborhood on the Westwood line.
UnparsedAddress: 21 Trailside Road, Medfield MA 02052

Community Information
Senior CommunityYN: No
Community Features: Public Transportation, Shopping, Tennis Court(s), Park, Walk/Jog Trails, Bike Path, Highway Access, House of Worship, Private School, Public School

Public facts

Beds: 5
Baths: 5.5
Sq. Ft.: 3,800
Stories: —
Parking Spaces: 8
Basement: Yes
Accessible: No
Lot Size: 1 acres
Style: Single Family Residential
Year Built: 1994
Year Renovated: 2025
County: Norfolk County
APN: 114726
HOA Dues: —
Garage: Yes
Features: Green, Pool

Home facts updated by owner on Jun 14, 2025

Other

Miscellaneous Information
Heat Zones: 3

Listing Information
Exclusions: Entry Hall Light Fixture
StandardStatus: Closed

Around this home

Schools

Ralph Wheelock School

Public PreK-3 • Assigned • 1.7mi

10/10

Thomas Blake Middle School

Public 6-8 • Assigned • 1.3mi

8/10

Medfield Senior High School

Public 9-12 • Assigned • 1.4mi

9/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

3/10 Fire Factor

0.31% chance of being in a wildfire in next 30 years

5/10 Heat Factor

7 days above 98° expected this year, 15 days in 30 years

6/10 Wind Factor

61% chance of strong winds in next 30 years

2/10 Air Factor

1 unhealthy days expected this year, 2 days in 30 years

Provided by First Street

Historical weather

Medfield, MA • 02052

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 9 hours in June and 4.4 hours in December, placing it below the U.S. average for solar exposure.

9 hrs

4.4 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$1.65M – $2.00M

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New listings for sale in 02052

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Home values near 21 Trailside Rd

Data from public records.

Address	Redfin Estimate
23 Trailside Rd, Medfield, MA 4 Beds \| 3.5 Baths \| 4513 Sq. Ft.	$1,574,155
8 Trailside Rd, Medfield, MA 4 Beds \| 2.5 Baths \| 2771 Sq. Ft.	$1,414,903

Address	Redfin Estimate
20 Trailside Rd, Medfield, MA 5 Beds \| 4.5 Baths \| 4400 Sq. Ft.	$1,710,934
10 Trailside Rd, Medfield, MA 4 Beds \| 2.5 Baths \| 3325 Sq. Ft.	$1,415,348

Address	Redfin Estimate
24 Trailside Rd, Medfield, MA 4 Beds \| 3 Baths \| 2902 Sq. Ft.	$1,349,693
14 Trailside Rd, Medfield, MA 4 Beds \| 2.5 Baths \| 3792 Sq. Ft.	$1,388,652

Property information provided by MLS PIN when last listed in 2022. This data may not show owner updates. Learn more.

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Redfin Estimate

Earn from this home

Market trends in 02052, MA

Sale history for 21 Trailside Rd

Tax history for 21 Trailside Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 02052

Home values near 21 Trailside Rd

More real estate resources