OFF MARKET

Off market nov 2021 for $1.6M

$2,100,128

•

7,161

sq ft

40 Winding Oaks Way, Boxford, MA 01921

About this home

Welcome to Winding Oaks Way - a 6 Bedroom Cape nestled on a picturesque 2 Acre lot. Elegant Living Room with fireplace, wet bar, & vaulted ceilings boasts openness as it flows into the Eat-In Kitchen equipped with island and SS appliances. First Floor Master with dressing room, walk-in closet, and Master Bath including jetted tub and walk in shower. Lovely Music Room and Home Library are other amazing features of the first floor. Huge 2nd Floor Game Room provides the perfect setting for entertaining. 5 good sized bedrooms are also located on 2nd floor, all with carpet and walk-in closets. Two full baths with dual vanity sinks are beside them. Many opportunities for home offices throughout this home! Partially finished basement includes a Home Theatre for watching movies or football games with the family. Large backyard includes hot tub, deck, cabana and heated pool - just in time for hot summer days! Other amenities include a 4-Car garage & laundry room. THIS HOME TRULY HAS IT ALL!

Single-familyProperty Type

2001Year Built

2.02 acresLot Size

$293Est. Price/Sq.Ft.

4 garage spacesParking

Listed by Team Lillian Montalto • Lillian Montalto Signature Properties

Bought with Jose Frias • Realty One Group Nest

Redfin checked: 2 minutes ago

•Source:MLS PIN #72856781

Redfin Estimate

$2,100,128

$475K since sold in November 2021$33K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 46.4% higher than the average sale price ($1.43M) of 6 comparable homes.

SOLD AUG 27, 2026
$1,350,000
A
5 beds3.5 baths3,423 sq ft
8 Ashland Rd, Boxford, MA 01921
SOLD SEP 1, 2026
$1,608,000
B
4 beds3.5 baths4,750 sq ft
58 Pheasant Brook Rd, North Andover, MA 01845
SOLD SEP 8, 2026
$1,510,000
C
4 beds4 baths4,186 sq ft
10 Bayns Hill Rd, Boxford, MA 01921
SOLD AUG 28, 2026
$1,300,000
D
4 beds3.5 baths3,907 sq ft
247 Webster Woods Ln, North Andover, MA 01845
SOLD AUG 31, 2026
$1,815,000
E
4 beds3 baths4,489 sq ft
42 Lockwood Ln, Boxford, MA 01921
SOLD MAY 29, 2026
$1,023,000
F
4 beds2.5 baths3,260 sq ft
990 Forest St, North Andover, MA 01845

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Earn from this home

Sell

$817,046

Est. take-home

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Rent

$4,257/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

23d

2 days MoM

Recently sold homes

0 MoM

New listings for sale

OPEN TODAY, 4PM TO 6PM
$1,199,000
4 beds2.5 baths2,843 sq ft
15 Joseph Smith Ln, Boxford, MA 01921
OPEN SAT, 12PM TO 1:30PM
$969,900
4 beds2.5 baths3,096 sq ft
778 Main St, Boxford, MA 01921
VIDEO TOUR
$2,500,000
4 beds3.5 baths4,070 sq ft
42 Great Pond Dr, Boxford, MA 01921
OPEN SAT, 1PM TO 2:30PM
$1,650,000
4 beds4 baths4,889 sq ft
17 Rock Brook Way, Boxford, MA 01921
See all

Provided by Redfin

Sale history for 40 Winding Oaks Way

Year

Property tax

Land + Additions

Assessment*

2023

$22,003 (+18.6%)

$446,700 + $1,143,100

$1,589,800

2022

$18,555 (−3.4%)

$372,600 + $846,500

$1,219,100

2021

$19,206 (+2.1%)

$338,900 + $860,700

$1,199,600

2020

$18,815 (+1.8%)

$352,400 + $811,200

$1,163,600

2018

$18,486 (−1.3%)

$335,400 + $805,700

$1,141,100

2017

$18,737 (−0.9%)

$319,600 + $829,200

$1,148,800

2016

$18,911 (+3.1%)

$319,600 + $829,300

$1,148,900

2015

$18,339 (+5.4%)

$319,600 + $827,300

$1,146,900

2014

$17,396 (+3.1%)

$319,600 + $804,900

$1,124,500

2013

$16,865 (+5.3%)

$319,600 + $813,800

$1,133,400

2012

$16,016 (+1.1%)

$340,000 + $796,700

$1,136,700

2011

$15,843 (+1.9%)

$350,200 + $805,400

$1,155,600

2010

$15,548 (+0.3%)

$376,200 + $880,700

$1,256,900

2009

$15,500

$418,100 + $899,900

$1,318,000

Tax history for 40 Winding Oaks Way

Year

Property tax

Land + Additions

Assessment*

2023

$22,003 (+18.6%)

$446,700 + $1,143,100

$1,589,800

2022

$18,555 (−3.4%)

$372,600 + $846,500

$1,219,100

2021

$19,206 (+2.1%)

$338,900 + $860,700

$1,199,600

2020

$18,815 (+1.8%)

$352,400 + $811,200

$1,163,600

2018

$18,486 (−1.3%)

$335,400 + $805,700

$1,141,100

2017

$18,737 (−0.9%)

$319,600 + $829,200

$1,148,800

2016

$18,911 (+3.1%)

$319,600 + $829,300

$1,148,900

2015

$18,339 (+5.4%)

$319,600 + $827,300

$1,146,900

2014

$17,396 (+3.1%)

$319,600 + $804,900

$1,124,500

2013

$16,865 (+5.3%)

$319,600 + $813,800

$1,133,400

2012

$16,016 (+1.1%)

$340,000 + $796,700

$1,136,700

2011

$15,843 (+1.9%)

$350,200 + $805,400

$1,155,600

2010

$15,548 (+0.3%)

$376,200 + $880,700

$1,256,900

2009

$15,500

$418,100 + $899,900

$1,318,000

*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

Stories

Lot width

—

Lot depth

—

Lot size

2.02 Acres

Year renovated

—

Sq. Ft.

5,509

Year built

2000

Style

Single Family Residential

County

Essex County

APN

4112554

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: 4
# of Covered Spaces: 4
Parking Spaces: 12
AttachedGarageYN: Yes
Parking Features: Under, Garage Door Opener, Garage Faces Side, Paved Drive, Off Street, Paved

Interior

Bedroom Information
Main Level Bedrooms: 1

Master Bedroom Information
Area: 330
Length: 22
Width: 15
Level: Main,First
Features: Walk-In Closet(s),Dressing Room

Bedroom #2 Information
Area: 208
Length: 16
Width: 13
Level: Second
Features: Walk-In Closet(s),Flooring - Wall to Wall Carpet

Bedroom #3 Information
Area: 240
Length: 15
Width: 16
Level: Second
Features: Walk-In Closet(s),Flooring - Wall to Wall Carpet

Bedroom #4 Information
Area: 294
Length: 14
Width: 21
Level: Second
Features: Walk-In Closet(s),Flooring - Wall to Wall Carpet

Bedroom #5 Information
Area: 342
Length: 18
Width: 19
Level: Second
Features: Walk-In Closet(s),Flooring - Wall to Wall Carpet

Bathroom Information
# of Bathrooms (Full): 3
# of Bathrooms (Half): 2
Main Level Bathrooms: 1
Master Bathroom Features: Yes

Bathroom #1 Information
Area: 180
Length: 18
Width: 10
Level: Main,First
Features: Bathroom - Full,Bathroom - With Shower Stall,Bathroom - With Tub,Double Vanity

Bathroom #2 Information
Area: 28
Length: 4
Width: 7
Level: First
Features: Bathroom - Half,Flooring - Stone/Ceramic Tile

Bathroom #3 Information
Area: 156
Length: 12
Width: 13
Level: Second
Features: Bathroom - Full,Bathroom - With Tub & Shower,Closet - Linen,Flooring - Stone/Ceramic Tile,Countertops - Stone/Granite/Solid,Double Vanity

Living Room Information
Area: 399
Length: 19
Width: 21
Level: Main,First
Features: Vaulted Ceiling(s),Flooring - Hardwood,Wet Bar,Open Floorplan

Dining Room Information
Area: 240
Length: 15
Width: 16
Level: Main,First
Features: Flooring - Hardwood

Kitchen Information
Area: 660
Length: 33
Width: 20
Level: Main,First
Features: Ceiling Fan(s),Flooring - Hardwood,Dining Area,Pantry,Countertops - Stone/Granite/Solid,Kitchen Island,Deck - Exterior,Open Floorplan,Slider,Stainless Steel Appliances

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

Laundry Information
Laundry Dimen: 8X13
Laundry Features: Washer Hookup, Sink, First Floor, Gas Dryer Hookup

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

Interior Features
# of Rooms (Total): 11
Door Features: Insulated Doors
Window Features: Insulated Windows
Flooring: Tile, Carpet, Hardwood, Flooring - Wall to Wall Carpet, Flooring - Hardwood, Flooring - Stone/Ceramic Tile
Interior Features: Ceiling Fan(s), Vaulted Ceiling(s), Closet, Open Floorplan, Bathroom - Half, Bathroom - Full, Bathroom - With Tub & Shower, Closet - Linen, Countertops - Stone/Granite/Solid, Double Vanity, Game Room, Bedroom, Library, Bathroom, Media Room, Central Vacuum, Wet Bar

Exterior

Building Information
Building Area (Total): 7,161
Foundation Details: Concrete Perimeter
Construction Materials: Frame
Year Built Source: Public Records
Year Built Details: Actual
Color: Grey
Lead Paint: None

Exterior Features
Fencing: Fenced/Enclosed, Fenced
Roof: Shingle
Patio And Porch Features: Deck - Composite, Patio
Exterior Features: Deck - Composite, Patio, Pool - Inground Heated, Cabana, Hot Tub/Spa, Storage, Professional Landscaping, Sprinkler System, Decorative Lighting, Fenced Yard

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

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

Lot Information
Lot Size (Acres): 2.02
Road Surface Type: Paved
Road Frontage Type: Public
Road Responsibility: Public Maintained Road

Financial

Tax Information
Tax Annual Amount: $19,206
Tax Year: 2021

Utilities

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

Heating & Cooling
Has Heating
Has Cooling
Heating: Forced Air, Natural Gas, Fireplace(s)
Cooling: Central Air

Location

Location Information
Directions: Towne Rd to Winding Oaks Way
UnparsedAddress: 40 Winding Oaks Way, Boxford MA 01921

Community Information
Senior CommunityYN: No
Community Features: Shopping, Pool, Park, Walk/Jog Trails, Stable(s), Golf, Medical Facility, Conservation Area, Highway Access, House of Worship, Private School, Public School

Public facts

Beds: 6
Baths: 4.0
Sq. Ft.: 5,509
Stories: 2.0
Lot Size: 2.02 acres
Style: Single Family Residential
Year Built: 2000
Year Renovated: —
County: Essex County
APN: 4112554

Home facts updated by county records on Jul 19, 2023

Other

Miscellaneous Information
Heat Zones: 8

Listing Information
Exclusions: See Attached Inclusions/Exclusions List.
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 • 3.2mi

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

0.15% 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

$2.00M – $2.42M

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Home values near 40 Winding Oaks Way

Data from public records.

Address	Redfin Estimate
53 Winding Oaks Way, Boxford, MA 3 Beds \| 1.5 Baths \| 2292 Sq. Ft.	$962,760
30 Winding Oaks Way #B, Boxford, MA 5 Beds \| 4.5 Baths \| 6182 Sq. Ft.	$2,099,560

Address	Redfin Estimate
52 Winding Oaks Way, Boxford, MA 4 Beds \| 2.5 Baths \| 2400 Sq. Ft.	$1,049,752
34 Winding Oaks Way, Boxford, MA 4 Beds \| 7 Baths \| 5400 Sq. Ft.	$2,094,974

Address	Redfin Estimate
4 Winding Oaks Way, Boxford, MA 4 Beds \| 3.5 Baths \| 4317 Sq. Ft.	$1,618,900
35 Winding Oaks Way, Boxford, MA 5 Beds \| 4.5 Baths \| 5985 Sq. Ft.	$2,130,622

Property information provided by MLS PIN when last listed in 2021. This data may not match . Learn more.

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