OFF MARKET

Off market may 2021 for $1.4M

$1,926,828

Est. refi paymentEst. refi $8,906/mo

•

5,842

sq ft

38 Winding Oaks Way, Boxford, MA 01921

About this home

Welcome to the beautiful & tranquil 38 Winding Oaks Way. This spacious & stately colonial is for the discriminating buyer who appreciates beautiful architectural details & high-end finishes. The inviting grand foyer has a magnificent bridal staircase leading to a luxurious master ensuite, 4 additional bedrooms, 3 baths and a spectacular media room featuring beamed ceilings, built-ins & dramatic windows! The Chef's kitchen offers custom cabinetry, a generous island, stone counters, Subzero & Wolf appliances, a separate bar area & dining area which opens to the expansive family room w/ coffered ceiling, gas fireplace, & oversized windows. Formal living/dining rooms combine elegant details with front-to-back views of the serene property. This amazing home also boasts a home office w/ built-ins and a light and airy sunroom opening to the fenced-in backyard & patio. Bonus, finish lower level, laundry rm & 3 car garage. Easy assess to highways & Masco Schools. Truly a Stunning Home!

Single-familyProperty Type

2001Year Built

6 acresLot Size

$330Est. Price/Sq.Ft.

3 garage spacesParking

Listed by Zoe Karademos • Coldwell Banker Realty - Beverly

Bought with Mary Rossi • Coldwell Banker Realty - Topsfield

Redfin checked: 2 minutes ago

•Source:MLS PIN #72791453

Redfin Estimate

$1,926,828

$476K since sold in May 2021$3,000 since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 19.5% higher than the average sale price ($1.61M) of 6 comparable homes.

SOLD JUN 30, 2026
$1,810,000
A
5 beds4.5 baths4,908 sq ft
21 Whitney Rd, Boxford, MA 01921
SOLD AUG 27, 2026
$1,350,000
B
5 beds3.5 baths3,423 sq ft
8 Ashland Rd, Boxford, MA 01921
SOLD MAY 15, 2026
$2,100,000
C
4 beds3.5 baths5,289 sq ft
85 Townsend Farm Rd, Boxford, MA 01921
SOLD SEP 1, 2026
$1,608,000
D
4 beds3.5 baths4,750 sq ft
58 Pheasant Brook Rd, North Andover, MA 01845
SOLD SEP 8, 2026
$1,510,000
E
4 beds4 baths4,186 sq ft
10 Bayns Hill Rd, Boxford, MA 01921
SOLD AUG 28, 2026
$1,300,000
F
4 beds3.5 baths3,907 sq ft
247 Webster Woods Ln, North Andover, MA 01845

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Earn from this home

Sell

$793,334

Est. take-home

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Refinance

Est. cash available

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Rent

$4,275/mo

Redfin rental estimate

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Market trends in 01921, MA

Last updated September 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

102.9%

0.8% MoM

Median sale price

$1.1M

$7K MoM

Avg. days on market

22d

2 days MoM

Recently sold homes

1 MoM

New listings for sale

$1,199,000
4 beds2.5 baths2,843 sq ft
15 Joseph Smith Ln, Boxford, MA 01921
$925,000
4 beds2.5 baths3,096 sq ft
778 Main St, Boxford, MA 01921
See all

Provided by Redfin

Sale history for 38 Winding Oaks Way

Date

Event

Price

MLS PIN #72791453

May 7, 2021

Sold

$1,451,000

$248/sq ft

Mar 9, 2021

Contingent

—

Mar 1, 2021

Listed

$1,295,000

$222/sq ft

MLS PIN #72636488

Jul 7, 2020

Sold

$1,180,000

$202/sq ft

May 18, 2020

Pending

—

May 4, 2020

Contingent

—

Apr 28, 2020

Price Changed

$1,195,000

$205/sq ft

Mar 20, 2020

Listed

$1,225,000

$210/sq ft

+25

Understated elegance describe this spacious & stately Colonial in highly desirable location. The attention to quality is obvious throughout. Detailed moldings, high ceilings, open front foyer, bridal staircase, Carlisle hardwood floors & custom built-ins are some of the special features. Expansive, white cook’s kitchen w/ Wood Mode custom cabinetry, large island, stone countertops, high end appliances (Subzero & Wolf), wine fridge & plenty of storage. Oversized family rm w/vaulted, coffered ceiling, gas fireplace, large windows & access to kitchen & sun room. Formal living & dining rooms. Large office w/ cherry built ins. 1st floor mudroom & laundry room. 2nd level has luxurious master bedroom suite w/tray ceiling, cove lighting, spacious bath & walk in closet. 3 addtitional bedrooms, one w/ensuite bath. Bonus/media room highlights built ins, beamed ceiling & dramatic window. Finished lower level has space for all. Mature plantings, paver patio, fenced yard. Masco Schools. Stunning!

MLS PIN #71433192

Apr 22, 2013

Sold

$1,300,000

$223/sq ft

Feb 28, 2013

Contingent

—

Sep 10, 2012

Listed

$1,350,000

$231/sq ft

+25

Exceptional living in this stunning updated Colonial. Enter through the front glass portico and be amazed at the grand foyer staircase and quality of the architectual detail. High ceilings, detailed custom built ins, crown moldings & high end finishes. Wood-Mode Kitchen, Carlisle flooring, Wolf, SubZero appliances, marble & granite countertops. Dramatic Family RM w/vaulted, beamed wood ceiling & gas fireplace. Gorgeous play/great room designed by professional above 3 car Gar. Private 6 acre lot.

MLS PIN #70019273

Nov 30, 2004

Sold

$1,455,000

$249/sq ft

Oct 15, 2004

Listing Removed

—

Apr 14, 2004

Listed

$1,600,000

$274/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$21,361 (+2.2%)

$482,100 + $1,061,300

$1,543,400

2022

$20,900 (+2.9%)

$408,000 + $965,200

$1,373,200

2021

$20,310 (−2.0%)

$374,300 + $894,300

$1,268,600

2020

$20,732 (+2.0%)

$387,800 + $894,300

$1,282,100

2018

$20,328 (−1.4%)

$370,800 + $884,000

$1,254,800

2017

$20,616 (+1.4%)

$353,400 + $910,600

$1,264,000

2016

$20,338 (−2.8%)

$353,400 + $882,200

$1,235,600

2015

$20,929 (+4.6%)

$353,400 + $955,500

$1,308,900

2014

$20,004 (−1.4%)

$353,400 + $939,700

$1,293,100

2013

$20,289 (+5.9%)

$353,400 + $1,010,100

$1,363,500

2012

$19,167 (+1.2%)

$373,800 + $986,500

$1,360,300

2011

$18,939 (−2.2%)

$384,000 + $997,400

$1,381,400

2010

$19,365 (+6.2%)

$412,000 + $1,153,500

$1,565,500

2009

$18,234

$457,900 + $1,092,600

$1,550,500

Tax history for 38 Winding Oaks Way

Year

Property tax

Land + Additions

Assessment*

2023

$21,361 (+2.2%)

$482,100 + $1,061,300

$1,543,400

2022

$20,900 (+2.9%)

$408,000 + $965,200

$1,373,200

2021

$20,310 (−2.0%)

$374,300 + $894,300

$1,268,600

2020

$20,732 (+2.0%)

$387,800 + $894,300

$1,282,100

2018

$20,328 (−1.4%)

$370,800 + $884,000

$1,254,800

2017

$20,616 (+1.4%)

$353,400 + $910,600

$1,264,000

2016

$20,338 (−2.8%)

$353,400 + $882,200

$1,235,600

2015

$20,929 (+4.6%)

$353,400 + $955,500

$1,308,900

2014

$20,004 (−1.4%)

$353,400 + $939,700

$1,293,100

2013

$20,289 (+5.9%)

$353,400 + $1,010,100

$1,363,500

2012

$19,167 (+1.2%)

$373,800 + $986,500

$1,360,300

2011

$18,939 (−2.2%)

$384,000 + $997,400

$1,381,400

2010

$19,365 (+6.2%)

$412,000 + $1,153,500

$1,565,500

2009

$18,234

$457,900 + $1,092,600

$1,550,500

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

Public record

Public record
Zoning

Beds

Baths

4.5

Stories

Lot width

—

Lot depth

—

Lot size

6 Acres

Year renovated

—

Sq. Ft.

5,753

Year built

2001

Style

Single Family Residential

County

Essex County

APN

4112555

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 19, 2023.

R-A

Residence-Agricultural District

A Residence-Agricultural District is intended as a district of single-family homes and for continuance of agricultural and accessory buildings customarily incidental for residential and agricultural uses upon one lot.

Permitted uses

Include but are not limited to:

Agriculture
Equestrian facility
Greenhouse / nursery
Livestock production
Religious facility
Housing-Single unit
Housing-Student
Educational/school
Library
Golf related

Property details

Parking

Parking Information
Has Garage
Has Open Parking
# of Garage Spaces: 3
# of Covered Spaces: 3
Parking Spaces: 7
AttachedGarageYN: Yes
Parking Features: Attached, Under, Garage Door Opener, Storage, Paved Drive, Off Street

Interior

Master Bedroom Information
Level: Second
Features: Bathroom - Full,Walk-In Closet(s),Flooring - Wall to Wall Carpet

Bedroom #2 Information
Level: Second
Features: Bathroom - Full,Closet,Flooring - Wall to Wall Carpet

Bedroom #3 Information
Level: Second
Features: Closet,Closet/Cabinets - Custom Built,Flooring - Wall to Wall Carpet

Bedroom #4 Information
Level: Second
Features: Closet,Flooring - Wall to Wall Carpet

Bedroom #5 Information
Level: Second
Features: Bathroom - 3/4,Closet,Flooring - Wall to Wall Carpet

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

Bathroom #1 Information
Level: First
Features: Bathroom - Half,Flooring - Stone/Ceramic Tile

Bathroom #2 Information
Level: Second
Features: Bathroom - Full,Flooring - Stone/Ceramic Tile

Bathroom #3 Information
Level: Second
Features: Bathroom - Full,Flooring - Stone/Ceramic Tile

Living Room Information
Level: First
Features: Flooring - Hardwood,Recessed Lighting,Crown Molding

Family Room Information
Level: First
Features: Cathedral Ceiling(s),Coffered Ceiling(s),Flooring - Hardwood,Window(s) - Picture,Recessed Lighting

Dining Room Information
Level: First
Features: Flooring - Hardwood,Recessed Lighting,Crown Molding

Kitchen Information
Level: First
Features: Closet/Cabinets - Custom Built,Flooring - Hardwood,Countertops - Stone/Granite/Solid,Kitchen Island,Open Floorplan,Wine Chiller

Office Room Information
Level: First
Features: Closet/Cabinets - Custom Built,Flooring - Hardwood,Window(s) - Picture,French Doors,Recessed Lighting,Crown Molding

Basement Information
Basement: Full, Finished, Interior Entry, Garage Access, Concrete

Laundry Information
Laundry Features: Closet/Cabinets - Custom Built, Flooring - Stone/Ceramic Tile, First Floor, Gas Dryer Hookup

Fireplace Information
Has Fireplace
# of Fireplaces (Total): 2
Fireplace Features: Family Room, Living Room

Interior Features
# of Rooms (Total): 16
Door Features: French Doors
Window Features: Window(s) - Picture
Flooring: Tile, Carpet, Hardwood, Wood Laminate, Flooring - Stone/Ceramic Tile, Flooring - Wall to Wall Carpet, Flooring - Hardwood
Interior Features: Bathroom - Full, Coffered Ceiling(s), Closet/Cabinets - Custom Built, Recessed Lighting, Crown Molding, Ceiling Fan(s), Bathroom, Media Room, Home Office, Sun Room, Exercise Room, Bonus Room, Central Vacuum, Walk-Up Attic, Wired for Sound

Exterior

Building Information
Building Area (Total): 5,842
Foundation Details: Concrete Perimeter
Construction Materials: Frame
Year Built Source: Public Records
Year Built Details: Actual
Lead Paint: None

Exterior Features
Fencing: Fenced/Enclosed, Fenced
Roof: Shingle
Patio And Porch Features: Patio
Exterior Features: Patio, Rain Gutters, Storage, Sprinkler System, Fenced Yard

Property Information
PropertySubType: Single Family Residence
Security Features: Security System

Lot Information
Lot Size (Acres): 6
Lot Features: Corner Lot, Wooded

Financial

Tax Information
Tax Annual Amount: $20,310.20
Tax Year: 2021

Utilities

Utility Information
Utilities: for Gas Range, for Gas Oven, for Gas Dryer, Icemaker Connection
Sewer: Private Sewer
Water Source: Private
Electric: Generator, Circuit Breakers

Heating & Cooling
Has Heating
Has Cooling
Heating: Forced Air, Hot Water, Natural Gas
Cooling: Central Air

Location

Location Information
Directions: Townsend Farms Rd to Winding Oaks Way
UnparsedAddress: 38 Winding Oaks Way, Boxford MA 01921

Community Information
Senior CommunityYN: No
Community Features: Walk/Jog Trails, Conservation Area, Highway Access, Public School

Public facts

Beds: 5
Baths: 4.5
Sq. Ft.: 5,753
Stories: 2.0
Lot Size: 6 acres
Style: Single Family Residential
Year Built: 2001
Year Renovated: —
County: Essex County
APN: 4112555

Home facts updated by county records on Jul 19, 2023

Other

Listing Information
Exclusions: Main Floor & Media Rm Window Treatments Excluded But Willing To Sell. Girl Bedrm Treatments Excluded
StandardStatus: Closed

Around this home

Schools

Harry Lee Cole School

Public PreK-2 • Assigned • 1.1mi

Masconomet Regional Middle School

Public 7-8 • Assigned • 3.1mi

6/10

Masconomet Regional High School

Public 9-12 • Assigned • 3.1mi

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

2/10 Fire Factor

0.00% chance of being in a wildfire in next 30 years

4/10 Heat Factor

7 days above 96° expected this year, 15 days in 30 years

6/10 Wind Factor

48% chance of strong winds in next 30 years

3/10 Air Factor

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

Provided by First Street

Historical weather

Boxford, MA • 01921

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 9.1 hours in June and 4.4 hours in December, placing it below the U.S. average for solar exposure.

9.1 hrs

4.4 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$1.83M – $2.22M

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New listings for sale in 01921

$1,199,000

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Home values near 38 Winding Oaks Way

Data from public records.

Address	Redfin Estimate
53 Winding Oaks Way, Boxford, MA 3 Beds \| 1.5 Baths \| 2292 Sq. Ft.	$962,168
30 Winding Oaks Way #B, Boxford, MA 5 Beds \| 4.5 Baths \| 6182 Sq. Ft.	$2,094,713

Address	Redfin Estimate
52 Winding Oaks Way, Boxford, MA 4 Beds \| 2.5 Baths \| 2400 Sq. Ft.	$1,043,904
34 Winding Oaks Way, Boxford, MA 4 Beds \| 7 Baths \| 5400 Sq. Ft.	$2,093,597

Address	Redfin Estimate
4 Winding Oaks Way, Boxford, MA 4 Beds \| 3.5 Baths \| 4317 Sq. Ft.	$1,622,582
35 Winding Oaks Way, Boxford, MA 5 Beds \| 4.5 Baths \| 5985 Sq. Ft.	$2,132,971

Property information provided by MLS PIN when last listed in 2021. 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 01921, MA

Sale history for 38 Winding Oaks Way

Tax history for 38 Winding Oaks Way

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 01921

Home values near 38 Winding Oaks Way

More real estate resources