SOLD OCT 24, 2025

Off Market Oct 2025 for $4.4M

$4,429,757

Est. refi paymentEst. refi $9,158/mo

•

7,679

sq ft

20 Foxcroft Rd, Winchester, MA 01890

About this home

A rare opportunity to own one of The Flats’ most celebrated homes! This 1930s Colonial Revival w/ classic curb appeal & elegant proportions sits on over ½ acre of estate-like grounds featuring heated pool, patios, pergola & multiple areas for effortless entertaining. Inside, a grand foyer & sweeping staircase introduce gracious rooms w/ exquisite millwork & superb flow, equally suited for relaxed family living or refined gatherings. Highlights include eat-in chef’s kitchen w/ island & timeless finishes, butler’s pantry, stately dining rm, large living & family rms & private study. Upstairs offers a luxurious primary suite w/ marble bath & dressing rm, plus 4 add’l BRs, 3 en suite. Lower level features versatile family/game rms & wine cellar. Carriage house (2007) w/ 4 garage bays, cabana bath & studio/gym offers endless possibilities & ADU potential. Moments to town center, top rated schools & train, this iconic home is where elegance & livability come together in perfect balance.

Single-familyProperty Type

1937Year Built

0.58 acresLot Size

$577Est. Price/Sq.Ft.

4 garage spacesParking

Listed by Carolyn Walsh • Better Homes and Gardens Real Estate - The Shanahan Group

Bought with Kim Covino & Co. Team • Compass

Redfin checked: 2 minutes ago

•Source:MLS PIN #73431361

Redfin Estimate

$4,429,757

$20K since sold in October 2025$58K since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 78.4% higher than the average sale price ($2.48M) of 6 comparable homes.

SOLD JUN 29, 2026
$1,700,000
A
5 beds3 baths3,271 sq ft
29 Pilgrim Dr, Winchester, MA 01890
SOLD FEB 25, 2026
$2,380,000
B
5 beds5.5 baths4,773 sq ft
8 Buckman Dr, Winchester, MA 01890
SOLD JUN 29, 2026
$2,549,000
C
4 beds4 baths5,674 sq ft
10 Viking Rd, Winchester, MA 01890
SOLD JUL 7, 2026
$3,070,000
D
6 beds8 baths7,168 sq ft
4 Lawrence St, Winchester, MA 01890
SOLD MAR 19, 2026
$2,100,000
E
5 beds4.5 baths3,191 sq ft
10 Hawthorne Rd, Winchester, MA 01890
SOLD MAY 29, 2026
$3,100,000
F
5 beds7.5 baths6,899 sq ft
54 Johnson Rd, Winchester, MA 01890

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Sell

$702,218

Est. take-home

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Est. cash available

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Market trends in 01890, MA

Last updated July 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

101.1%

+0.0% MoM

Median sale price

$1.4M

$57K MoM

Avg. days on market

20d

0 days MoM

Recently sold homes

14 MoM

New listings for sale

EARLY ACCESS
$1,699,000
3 beds2 baths2,327 sq ft
4 Churchill Rd, Winchester, MA 01890
OPEN TODAY, 12:30PM TO 1:30PM
$2,849,000
5 beds4.5 baths5,058 sq ft
7 Viking Rd, Winchester, MA 01890
OPEN TODAY, 12:30PM TO 2PM
$1,699,000
5 beds3.5 baths3,180 sq ft
30 Farrow St, Winchester, MA 01890
$1,098,000
3 beds1.5 baths1,657 sq ft
17 Russell Rd, Winchester, MA 01890
OPEN TODAY, 12PM TO 1:30PM
$1,999,000
4 beds2.5 baths3,757 sq ft
85 High St, Winchester, MA 01890
EARLY ACCESS
Unknown
3 beds3 baths5,127 sq ft
187 High St, Winchester, MA 01890
$949,999
4 beds2 baths2,326 sq ft
96 Loring Ave, Winchester, MA 01890
OPEN TODAY, 12PM TO 1:30PM
$3,199,000
5 beds4.5 baths5,406 sq ft
10 Rangeley Rd, Winchester, MA 01890
See all

Provided by Redfin

Sale history for 20 Foxcroft Rd

Date

Event

Price

MLS PIN #73431361

Oct 24, 2025

Sold

$4,450,000

$580/sq ft

Sep 18, 2025

Contingent

—

Sep 16, 2025

Listed

$4,399,000

$573/sq ft

MLS PIN #30324413

Aug 2, 1999

Sold

$1,825,000

$238/sq ft

Jun 4, 1999

Listing Removed

—

May 27, 1999

Listed

$1,875,000

$244/sq ft

Year

Property tax

Land + Additions

Assessment*

2025

$54,223 (+9.8%)

$1,363,400 + $3,526,000

$4,889,400

2023

$49,366

$1,323,400 + $3,401,000

$4,724,400

2022

$49,399 (+1.3%)

$1,123,100 + $2,825,700

$3,948,800

2021

$48,787 (+3.6%)

$983,100 + $2,819,500

$3,802,600

2020

$47,114 (+5.6%)

$983,100 + $2,819,500

$3,802,600

2019

$44,596 (+1.7%)

$863,100 + $2,819,500

$3,682,600

2018

$43,838 (+3.8%)

$843,100 + $2,753,100

$3,596,200

2017

$42,240 (+7.6%)

$802,100 + $2,637,600

$3,439,700

2016

$39,265 (+0.3%)

$802,100 + $2,559,600

$3,361,700

2015

$39,159 (+0.5%)

$729,100 + $2,496,500

$3,225,600

2014

$38,976 (−0.9%)

$663,100 + $2,415,600

$3,078,700

2013

$39,315 (+2.6%)

$663,100 + $2,415,600

$3,078,700

2012

$38,324 (+3.7%)

$638,100 + $2,415,600

$3,053,700

2011

$36,950 (+14.6%)

$638,100 + $2,415,600

$3,053,700

2010

$32,229 (+2.1%)

$649,900 + $2,150,200

$2,800,100

2009

$31,557

$649,900 + $2,150,200

$2,800,100

Tax history for 20 Foxcroft Rd

Year

Property tax

Land + Additions

Assessment*

2025

$54,223 (+9.8%)

$1,363,400 + $3,526,000

$4,889,400

2023

$49,366

$1,323,400 + $3,401,000

$4,724,400

2022

$49,399 (+1.3%)

$1,123,100 + $2,825,700

$3,948,800

2021

$48,787 (+3.6%)

$983,100 + $2,819,500

$3,802,600

2020

$47,114 (+5.6%)

$983,100 + $2,819,500

$3,802,600

2019

$44,596 (+1.7%)

$863,100 + $2,819,500

$3,682,600

2018

$43,838 (+3.8%)

$843,100 + $2,753,100

$3,596,200

2017

$42,240 (+7.6%)

$802,100 + $2,637,600

$3,439,700

2016

$39,265 (+0.3%)

$802,100 + $2,559,600

$3,361,700

2015

$39,159 (+0.5%)

$729,100 + $2,496,500

$3,225,600

2014

$38,976 (−0.9%)

$663,100 + $2,415,600

$3,078,700

2013

$39,315 (+2.6%)

$663,100 + $2,415,600

$3,078,700

2012

$38,324 (+3.7%)

$638,100 + $2,415,600

$3,053,700

2011

$36,950 (+14.6%)

$638,100 + $2,415,600

$3,053,700

2010

$32,229 (+2.1%)

$649,900 + $2,150,200

$2,800,100

2009

$31,557

$649,900 + $2,150,200

$2,800,100

*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

—

Stories

—

Lot width

—

Lot depth

—

Lot size

0.58 Acres

Year renovated

—

Sq. Ft.

—

Year built

—

Style

Other

County

Middlesex County

APN

2886193S

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 29, 2026.

Property details

Parking

Parking Information
Has Garage
Has Open Parking
# of Garage Spaces: 4
# of Covered Spaces: 4
Parking Spaces: 6
Parking Features: Detached, Garage Door Opener, Heated Garage, Paved Drive, Off Street, Paved

Interior

Virtural Tour Information
Virtual Tour 1 (External Link)

Master Bedroom Information
Area: 465
Length: 31
Width: 15
Level: Second
Features: Walk-In Closet(s),Closet/Cabinets - Custom Built,Flooring - Hardwood,Dressing Room

Bedroom #2 Information
Area: 266
Length: 19
Width: 14
Level: Second
Features: Closet/Cabinets - Custom Built,Flooring - Hardwood,Window(s) - Bay/Bow/Box

Bedroom #3 Information
Area: 234
Length: 18
Width: 13
Level: Second
Features: Closet/Cabinets - Custom Built,Flooring - Hardwood

Bedroom #4 Information
Area: 195
Length: 15
Width: 13
Level: Second
Features: Closet/Cabinets - Custom Built,Flooring - Hardwood

Bedroom #5 Information
Area: 204
Length: 17
Width: 12
Level: Second
Features: Closet/Cabinets - Custom Built,Flooring - Hardwood,Window(s) - Bay/Bow/Box,Recessed Lighting,Window Seat

Bathroom Information
# of Bathrooms (Full): 4
# of Bathrooms (Half): 3
Master Bathroom Features: Yes

Bathroom #1 Information
Area: 45
Length: 5
Width: 9
Level: First
Features: Bathroom - Half,Flooring - Hardwood,Lighting - Pendant

Bathroom #2 Information
Area: 156
Length: 12
Width: 13
Level: Second
Features: Bathroom - Full,Flooring - Marble,Countertops - Stone/Granite/Solid,Double Vanity,Recessed Lighting,Steam / Sauna,Lighting - Sconce,Lighting - Overhead

Bathroom #3 Information
Area: 80
Length: 10
Width: 8
Level: Second
Features: Bathroom - Full,Bathroom - Tiled With Tub & Shower,Flooring - Stone/Ceramic Tile,Lighting - Overhead

Living Room Information
Area: 475
Length: 19
Width: 25
Level: First
Features: Flooring - Hardwood,Lighting - Sconce,Crown Molding

Family Room Information
Area: 342
Length: 19
Width: 18
Level: First
Features: Flooring - Hardwood,Window(s) - Bay/Bow/Box,French Doors,Recessed Lighting,Lighting - Sconce,Lighting - Overhead,Crown Molding

Dining Room Information
Area: 288
Length: 18
Width: 16
Level: First
Features: Flooring - Hardwood,French Doors,Wainscoting,Lighting - Sconce,Lighting - Pendant,Crown Molding

Kitchen Information
Area: 416
Length: 16
Width: 26
Level: First
Features: Flooring - Hardwood,Window(s) - Bay/Bow/Box,Dining Area,Pantry,Countertops - Stone/Granite/Solid,Kitchen Island,Wet Bar,Exterior Access,Recessed Lighting,Lighting - Sconce,Lighting - Pendant,Crown Molding

Office Room Information
Area: 40
Length: 8
Width: 5
Level: Second
Features: Bathroom - Full,Bathroom - Tiled With Shower Stall,Flooring - Stone/Ceramic Tile

Basement Information
Basement: Full, Finished, Interior Entry

Laundry Information
Laundry Dimen: 10X5
Laundry Features: Closet/Cabinets - Custom Built, Flooring - Stone/Ceramic Tile, Electric Dryer Hookup, Lighting - Overhead, Second Floor

Fireplace Information
Has Fireplace
# of Fireplaces (Total): 4
Fireplace Features: Dining Room, Living Room, Master Bedroom

Interior Features
# of Rooms (Total): 14
Door Features: French Doors
Flooring: Tile, Marble, Hardwood, Stone / Slate, Flooring - Hardwood, Flooring - Stone/Ceramic Tile, Flooring - Wall to Wall Carpet
Interior Features: Recessed Lighting, Lighting - Sconce, Wet Bar, Wainscoting, Bathroom - Full, Bathroom - Tiled With Tub, Lighting - Overhead, Bathroom - Tiled With Shower Stall, Study, Game Room, Bathroom, Office, Play Room, Wine Cellar, Wet Bar, Wired for Sound

Exterior

Building Information
Building Area (Total): 7,679
Foundation Details: Concrete Perimeter
Construction Materials: Frame
Year Built Source: Public Records
Year Built Details: Actual
Color: Brick-Red

Exterior Features
Fencing: Fenced/Enclosed, Fenced
Roof: Slate
Patio And Porch Features: Patio
Exterior Features: Patio, Pool - Inground Heated, Cabana, Professional Landscaping, Sprinkler System, Decorative Lighting, Fenced Yard, Garden

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

Property Information
PropertySubType: Single Family Residence
Security Features: Security System
Other Structures: Cabana

Lot Information
Lot Size (Acres): 0.58
Lot Features: Corner Lot, Level

Financial

Tax Information
Tax Annual Amount: $54,223
Tax Year: 2025

Utilities

Utility Information
Utilities: for Gas Range, for Electric Oven, for Electric Dryer
Sewer: Public Sewer
Water Source: Public

Heating & Cooling
Has Heating
Has Cooling
Heating: Forced Air, Radiant, Natural Gas, Fireplace
Cooling: Central Air

Location

Location Information
Directions: Church Street to Wedgemere Ave to Foxcroft Road
UnparsedAddress: 20 Foxcroft Road, Winchester MA 01890

Community Information
Senior CommunityYN: No
Community Features: Public Transportation, Shopping, Pool, Tennis Court(s), Park, Walk/Jog Trails, Golf, Medical Facility, Bike Path, House of Worship, Public School, T-Station

Public facts

Beds: —
Baths: —
Sq. Ft.: —
Stories: —
Lot Size: 0.58 acres
Style: Other
Year Built: —
Year Renovated: —
County: Middlesex County
APN: 2886193S

Home facts updated by county records on Jul 29, 2026

Other

Miscellaneous Information
Heat Zones: 8

Listing Information
StandardStatus: Closed

Around this home

Schools

Ambrose Elementary School

Public K-5 • Assigned • 0.4mi

10/10

McCall Middle School

Public 6-8 • Assigned • 0.9mi

9/10

Winchester High School

Public 9-12 • Assigned • 1.0mi

10/10

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

1/10 Fire Factor

Unlikely to be 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

50% chance of strong winds in next 30 years

3/10 Air Factor

2 unhealthy days expected this year, 3 days in 30 years

Provided by First Street

Historical weather

Winchester, MA • 01890

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

Try the sun simulator tool to see how light moves across the property at different times of day and year.

Provided by Shadowmap

Estimated sale price

$4.21M – $5.10M

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New listings for sale in 01890

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Home values near 20 Foxcroft Rd

Data from public records.

Address	Redfin Estimate
12 Foxcroft Road, Winchester, MA 8 Beds \| 4 Baths \| 4968 Sq. Ft.	$2,682,210
15 Foxcroft Road, Winchester, MA 6 Beds \| 5 Baths \| 7081 Sq. Ft.	$3,448,064

Address	Redfin Estimate
4 Foxcroft Road, Winchester, MA 4 Beds \| 3.5 Baths \| 3200 Sq. Ft.	$2,367,836
21 Foxcroft Road, Winchester, MA 5 Beds \| 2.5 Baths \| 3696 Sq. Ft.	$2,455,693

Address	Redfin Estimate
9 Foxcroft Road, Winchester, MA 5 Beds \| 4.5 Baths \| 5089 Sq. Ft.	$3,102,366
25 Foxcroft Road, Winchester, MA 6 Beds \| 4.5 Baths \| 5400 Sq. Ft.	$3,034,070

Property information provided by MLS PIN when last listed in 2025. This data may not match . 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 01890, MA

Sale history for 20 Foxcroft Rd

Tax history for 20 Foxcroft Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 01890

Home values near 20 Foxcroft Rd

More real estate resources