OFF MARKET

Off Market Jan 2019 for $2.4M

$3,706,907

•

5,810

sq ft

5 Winding Rd, Lexington, MA 02421

About this home

50% SOLD at Winding Road, LEXINGTON'S NEWEST NEIGHBORHOOD, comprised of 10 shingle style homes in total, set on two cul de sacs, nestled between 2 golf courses & abutting wooded conservation land. This neighborhood offers a streetscape & value rarely found in Lexington. Distinguished by character, style & beautiful outdoor living space, each home is unique, custom designed with no detail left undone. Featuring a modern, contemporary palette, personally selected by New York Times Best Selling Author (Elements of Style) & designer, Erin Gates. Overlooking the golf course, this home enjoys perfectly blended indoor /outdoor living space with a large deck off the family room & bluestone patio off the lower level, accessed by over-sized sliders. The 1st floor has a open concept floor plan that today's families crave. Flooded with natural light, this home is impressive from the moment you enter, with a 2 story foyer, wide staircase with wraparound windows and beautiful mill work.

Single-familyProperty Type

2019Year Built

1.15 acresLot Size

$638Est. Price/Sq.Ft.

2 garage spacesParking

Listed by Deborah Fogarty • Coldwell Banker Residential Brokerage - Lexington

Bought with The Petrowsky Jones Group • Compass

Redfin checked: a minute ago

•Source:MLS PIN #72439013

Redfin Estimate

$3,706,907

$1.2M since sold in January 2019$23K since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 24.7% higher than the average sale price ($2.97M) of 6 comparable homes.

SOLD AUG 17, 2026
$3,438,000
A
6 beds6 baths6,557 sq ft
92 Hill St, Lexington, MA 02421
SOLD JUN 11, 2026
$2,658,150
B
5 beds5 baths5,004 sq ft
46 Asbury St, Lexington, MA 02421
SOLD JUN 26, 2026
$2,810,000
C
6 beds7 baths5,940 sq ft
8 Lake St, Lexington, MA 02421
SOLD JUL 1, 2026
$3,125,000
D
5 beds3 baths4,361 sq ft
64 Hill St, Lexington, MA 02421
SOLD MAY 13, 2026
$2,500,000
E
6 beds5 baths4,408 sq ft
1 Revere St, Lexington, MA 02420
SOLD APR 16, 2026
$3,300,000
F
5 beds5.5 baths6,074 sq ft
25 Flintlock Rd, Lexington, MA 02420

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Earn from this home

Sell

$1,848,193

Est. take-home

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Rent

$8,024/mo

Redfin rental estimate

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Market trends in 02421, MA

Last updated July 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

102.4%

0.7% MoM

Median sale price

$1.7M

$12K MoM

Avg. days on market

22d

3 days MoM

Recently sold homes

26 MoM

New listings for sale

3D WALKTHROUGH
$999,000
3 beds1.5 baths1,372 sq ft
1 Constitution Rd, Lexington, MA 02421
3D WALKTHROUGH
$3,195,000
7 beds5 baths5,114 sq ft
16 Middleby Rd, Lexington, MA 02421
See all

Provided by Redfin

Sale history for 5 Winding Rd

Year

Property tax

Land + Additions

Assessment*

2025

$39,955 (+3.2%)

$1,176,000 + $2,091,000

$3,267,000

2024

$38,722 (+6.6%)

$1,120,000 + $2,041,000

$3,161,000

2023

$36,322 (+2.8%)

$1,021,000 + $1,773,000

$2,794,000

2022

$35,342 (−2.0%)

$930,000 + $1,631,000

$2,561,000

2021

$36,061 (+13.4%)

$887,000 + $1,619,000

$2,506,000

2020

$31,809 (+100.2%)

$770,000 + $1,494,000

$2,264,000

2019

$15,885

$734,000 + $391,000

$1,125,000

Tax history for 5 Winding Rd

Year

Property tax

Land + Additions

Assessment*

2025

$39,955 (+3.2%)

$1,176,000 + $2,091,000

$3,267,000

2024

$38,722 (+6.6%)

$1,120,000 + $2,041,000

$3,161,000

2023

$36,322 (+2.8%)

$1,021,000 + $1,773,000

$2,794,000

2022

$35,342 (−2.0%)

$930,000 + $1,631,000

$2,561,000

2021

$36,061 (+13.4%)

$887,000 + $1,619,000

$2,506,000

2020

$31,809 (+100.2%)

$770,000 + $1,494,000

$2,264,000

2019

$15,885

$734,000 + $391,000

$1,125,000

*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

1.17 Acres

Year renovated

—

Sq. Ft.

4,191

Year built

2018

Style

Single Family Residential

County

Middlesex County

APN

5042117

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 16, 2026.

Property details

Parking

Parking Information
Has Garage
# of Garage Spaces: 2
# of Covered Spaces: 2
Parking Spaces: 5
AttachedGarageYN: Yes
Parking Features: Attached, Garage Door Opener, Storage, Garage Faces Side, Insulated, Off Street

Interior

Master Bedroom Information
Area: 342
Length: 18
Width: 19
Level: Second
Features: Bathroom - Full,Closet - Linen,Walk-In Closet(s),Flooring - Hardwood

Bedroom #2 Information
Area: 144
Length: 12
Width: 12
Level: Second
Features: Bathroom - Full,Closet,Flooring - Hardwood

Bedroom #3 Information
Area: 182
Length: 14
Width: 13
Level: Second
Features: Bathroom - 3/4,Closet,Flooring - Hardwood,Recessed Lighting

Bedroom #4 Information
Area: 182
Length: 14
Width: 13
Level: Second
Features: Bathroom - 3/4,Walk-In Closet(s),Flooring - Hardwood,Recessed Lighting

Bedroom #5 Information
Area: 238
Length: 14
Width: 17
Level: Third
Features: Walk-In Closet(s),Flooring - Hardwood,Recessed Lighting

Bathroom Information
# of Bathrooms (Full): 5
# of Bathrooms (Half): 1
Master Bathroom Features: Yes

Bathroom #1 Information
Area: 300
Length: 20
Width: 15
Level: Third
Features: Walk-In Closet(s),Flooring - Hardwood,Recessed Lighting

Bathroom #2 Information
Area: 187
Length: 11
Width: 17
Level: Second
Features: Bathroom - Full,Bathroom - Tiled With Tub & Shower,Flooring - Stone/Ceramic Tile,Enclosed Shower - Fiberglass,Double Vanity,Lighting - Sconce,Lighting - Overhead

Bathroom #3 Information
Area: 81
Length: 9
Width: 9
Level: Second
Features: Bathroom - 3/4,Bathroom - Double Vanity/Sink,Bathroom - Tiled With Shower Stall,Flooring - Stone/Ceramic Tile,Lighting - Sconce

Living Room Information
Area: 280
Length: 20
Width: 14
Level: First
Features: Flooring - Hardwood,Recessed Lighting

Family Room Information
Area: 225
Length: 15
Width: 15
Level: First
Features: Cathedral Ceiling(s),Flooring - Hardwood,Exterior Access

Dining Room Information
Area: 192
Length: 16
Width: 12
Level: First
Features: Flooring - Hardwood

Kitchen Information
Area: 304
Length: 19
Width: 16
Level: First
Features: Flooring - Hardwood,Pantry,Countertops - Stone/Granite/Solid,Kitchen Island,Recessed Lighting,Stainless Steel Appliances,Wine Chiller

Basement Information
Basement: Full

Laundry Information
Laundry Dimen: 10X6
Laundry Features: Flooring - Stone/Ceramic Tile, Gas Dryer Hookup, Washer Hookup, Second Floor

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

Interior Features
# of Rooms (Total): 14
Window Features: Insulated Windows, Screens
Flooring: Tile, Vinyl, Hardwood, Flooring - Vinyl, Flooring - Hardwood, Flooring - Stone/Ceramic Tile
Interior Features: Recessed Lighting, Bathroom - Full, Walk-In Closet(s), Bathroom - Tiled With Tub, Exercise Room, Bonus Room, Bathroom, Media Room, Bedroom

Exterior

Building Information
Building Area (Total): 5,810
Foundation Details: Concrete Perimeter
Construction Materials: Frame
Year Built Source: Builder
Year Built Details: Under Construction
Color: Dark Gray
Lead Paint: None

Exterior Features
Roof: Asphalt/Composition Shingles
Patio And Porch Features: Deck - Composite, Patio
Exterior Features: Deck - Composite, Patio, Rain Gutters, Professional Landscaping, Sprinkler System, Decorative Lighting, Screens

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

Lot Information
Lot Size (Acres): 1.15
Lot Features: Wooded, Gentle Sloping
Road Frontage Type: Public

Financial

Tax Information
Tax Annual Amount: $9,999
Tax Year: 2018

Utilities

Utility Information
Utilities: for Gas Range, for Gas Oven, for Gas Dryer, Washer Hookup
Sewer: Public Sewer
Water Source: Public
Electric: 200+ Amp Service

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

Location

HOA Information
Has Association
Association Fee Frequency: Unknown

Location Information
Directions: Please GPS - 167 Cedar Street, New development. Not in on maps yet. New Development.
UnparsedAddress: 5 Winding Road, Lexington MA 02421

Community Information
Senior CommunityYN: No
Community Features: Public Transportation, Shopping, Pool, Golf, Bike Path, Highway Access, Public School

Public facts

Beds: 6
Baths: 5.5
Sq. Ft.: 4,191
Stories: 3.0
Lot Size: 1.17 acres
Style: Single Family Residential
Year Built: 2018
Year Renovated: —
County: Middlesex County
APN: 5042117

Home facts updated by county records on Jul 16, 2026

Other

Miscellaneous Information
Heat Zones: 4

Listing Information
StandardStatus: Closed

Around this home

Schools

Maria Hastings Elementary School

Public K-5 • Assigned • 0.8mi

10/10

Wm Diamond Middle School

Public 6-8 • Assigned • 1.1mi

9/10

Lexington High School

Public 9-12 • Assigned • 1.1mi

10/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Local insights from Redfin agents

Lexington continues to be a competitive Seller's market driven by its historic appeal & location. With buildable land exhausted, true inventory growth is very constrained; development mostly replaces existing homes. New zoning laws will eventually...
2 months ago • Lexington
Benjamin Ginsburg
Redfin Premier agent
151 deals
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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

27% 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

Lexington, MA • 02421

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

$3.52M – $4.26M

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Nearby similar homes

3D WALKTHROUGH

$999,000

3 beds1.5 baths1,372 sq ft

1 Constitution Rd, Lexington, MA 02421

$2,998,000

6 beds5.5 baths6,131 sq ft

22 Constitution Rd, Lexington, MA 02421

$929,000

3 beds1 bath1,299 sq ft

242 Lincoln St, Lexington, MA 02421

$1,999,000

4 beds4 baths4,133 sq ft

9 Woodcliffe Rd, Lexington, MA 02421

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4 Augustus Rd, Lexington, MA 02421

LISTED BY REDFIN

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New listings for sale in 02421

3D WALKTHROUGH

$999,000

3 beds1.5 baths1,372 sq ft

1 Constitution Rd, Lexington, MA 02421

3D WALKTHROUGH

$3,195,000

7 beds5 baths5,114 sq ft

16 Middleby Rd, Lexington, MA 02421

Home values near 5 Winding Rd

Data from public records.

Address	Redfin Estimate
6 Winding Road, Lexington, MA 6 Beds \| 6.5 Baths \| 7441 Sq. Ft.	$4,500,601
3 Winding Road, Lexington, MA 6 Beds \| 5.5 Baths \| 5700 Sq. Ft.	$3,605,534

Address	Redfin Estimate
2 Winding Road, Lexington, MA 6 Beds \| 5.5 Baths \| 5305 Sq. Ft.	$3,533,771
1 Winding Road, Lexington, MA 6 Beds \| 4.5 Baths \| 5176 Sq. Ft.	$3,478,465

Address	Redfin Estimate
8 Winding Road, Lexington, MA 5 Beds \| 5.5 Baths \| 5161 Sq. Ft.	$3,918,278
1 Winding Road, Lexington, MA 6 Beds \| 4.5 Baths \| 5176 Sq. Ft.	$3,286,450

Property information provided by MLS PIN when last listed in 2019. 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 02421, MA

Sale history for 5 Winding Rd

Tax history for 5 Winding Rd

Public record

Property details

Around this home

Schools

Lifestyle

Local insights from Redfin agents

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 02421

Home values near 5 Winding Rd

More real estate resources