OFF MARKET

Off market sep 2019 for $1.4M

$2,481,178

•

15,556

sq ft

310 Flagg Hill Road On Windermere, Boxboro, MA 01719

About this home

Complete private, gated estate nestled on top of Flagg Hill surrounded by 286 acres of protected conservation land. Unparalleled views of Mt. Wachusett, sunrises sunsets with abundance of wildlife. Abuts Conservation land with walking trails. Truly one of a kind unique property located in the desirable Middlesex county surrounding towns include Acton, Concord, Stow and Harvard. Minutes drive from Minute Man Air Field. No amenities were spared. Master wing with observatory connected to the office with private balcony.Specialty rooms include Indoor spa/hot tub, weight room, locker room, game room. 12 seated fully functional bar with commercial grade appliances with easy access to the in-ground pool area.Ideal for entertaining, lavish parties, corporate retreats with privacy. Marble dining room floors and counter tops. High ceilings with immense space.4 bay car garage with room for work space and storage.A true feeling of having your own private mountain just outside Boston.

Single-familyProperty Type

1985Year Built

8.26 acresLot Size

$159Est. Price/Sq.Ft.

4 garage spacesParking

Listed by Jamieson Chalmers • Coldwell Banker Residential Brokerage - Concord

Bought with Jamieson Chalmers • Coldwell Banker Residential Brokerage - Concord

Redfin checked: a minute ago

•Source:MLS PIN #72251155

Redfin Estimate

$2,481,178

$1.0M since sold in September 2019$4,000 since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 77.8% higher than the average sale price ($1.40M) of 6 comparable homes.

SOLD SEP 18, 2026
$1,370,000
A
4 beds3.5 baths3,805 sq ft
85 Cedarwood Rd, Boxboro, MA 01719
SOLD SEP 30, 2026
$1,637,500
B
4 beds4.5 baths4,893 sq ft
356 Burroughs Rd, Boxboro, MA 01719
SOLD JUN 24, 2026
$2,170,000
C
5 beds5 baths6,183 sq ft
18 Woodchester Dr, Acton, MA 01720
BOUGHT WITH REDFIN JUN 24, 2026
$925,000
D
4 beds2.5 baths2,916 sq ft
29 Bicentennial Way, Boxboro, MA 01719
SOLD JUN 26, 2026
$1,321,000
E
4 beds3.5 baths4,016 sq ft
7 Woodfield Rd, Acton, MA 01720
SOLD AUG 14, 2026
$950,000
F
4 beds2.5 baths3,109 sq ft
117 Summer Rd, Boxboro, MA 01719

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Earn from this home

Sell

$1,358,211

Est. take-home

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Rent

$4,330/mo

Redfin rental estimate

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Market trends in 01719, MA

Last updated September 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

100.6%

0.1% MoM

Median sale price

$1.1M

$117K MoM

Avg. days on market

26d

6 days MoM

Recently sold homes

1 MoM

New listings for sale

OPEN SUN, 11AM TO 12:30PM
$1,195,000
4 beds3 baths3,852 sq ft
525 Old Harvard Rd, Boxboro, MA 01719
OPEN SAT, 12:30PM TO 2:30PM
$849,999
3 beds3 baths3,300 sq ft
77 Woodward Ln, Boxboro, MA 01719
See all

Provided by Redfin

Sale history for 310 Flagg Hill Road On Windermere

Year

Property tax

Land + Additions

Assessment*

2025

$29,182 (−2.1%)

$750,400 + $1,177,100

$1,927,500

2024

$29,802 (+7.7%)

$738,400 + $1,249,700

$1,988,100

2023

$27,666 (−6.7%)

$706,000 + $1,076,600

$1,782,600

2022

$29,640 (+13.3%)

$706,000 + $995,500

$1,701,500

2020

$26,155 (−21.7%)

$706,000 + $858,300

$1,564,300

2019

$33,418 (−6.4%)

$706,000 + $1,329,200

$2,035,200

2018

$35,691 (−2.2%)

$560,900 + $1,610,100

$2,171,000

2017

$36,511 (+2.6%)

$560,900 + $1,611,100

$2,172,000

2016

$35,596 (+4.7%)

$560,900 + $1,614,900

$2,175,800

2015

$34,011 (−6.0%)

$504,600 + $1,538,100

$2,042,700

2014

$36,192 (−0.3%)

$497,800 + $1,548,100

$2,045,900

2013

$36,298 (−2.4%)

$503,800 + $1,548,100

$2,051,900

2012

$37,202 (+4.1%)

$707,900 + $1,373,900

$2,081,800

2011

$35,740 (+5.1%)

$765,000 + $1,291,400

$2,056,400

2010

$33,992 (+4.6%)

$765,000 + $1,291,400

$2,056,400

2009

$32,495

$813,800 + $1,375,900

$2,189,700

Tax history for 310 Flagg Hill Road On Windermere

Year

Property tax

Land + Additions

Assessment*

2025

$29,182 (−2.1%)

$750,400 + $1,177,100

$1,927,500

2024

$29,802 (+7.7%)

$738,400 + $1,249,700

$1,988,100

2023

$27,666 (−6.7%)

$706,000 + $1,076,600

$1,782,600

2022

$29,640 (+13.3%)

$706,000 + $995,500

$1,701,500

2020

$26,155 (−21.7%)

$706,000 + $858,300

$1,564,300

2019

$33,418 (−6.4%)

$706,000 + $1,329,200

$2,035,200

2018

$35,691 (−2.2%)

$560,900 + $1,610,100

$2,171,000

2017

$36,511 (+2.6%)

$560,900 + $1,611,100

$2,172,000

2016

$35,596 (+4.7%)

$560,900 + $1,614,900

$2,175,800

2015

$34,011 (−6.0%)

$504,600 + $1,538,100

$2,042,700

2014

$36,192 (−0.3%)

$497,800 + $1,548,100

$2,045,900

2013

$36,298 (−2.4%)

$503,800 + $1,548,100

$2,051,900

2012

$37,202 (+4.1%)

$707,900 + $1,373,900

$2,081,800

2011

$35,740 (+5.1%)

$765,000 + $1,291,400

$2,056,400

2010

$33,992 (+4.6%)

$765,000 + $1,291,400

$2,056,400

2009

$32,495

$813,800 + $1,375,900

$2,189,700

*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

7.5

Stories

Lot width

—

Lot depth

—

Lot size

8.26 Acres

Year renovated

—

Sq. Ft.

7,960

Year built

1985

Style

Single Family Residential

County

Middlesex County

APN

386950

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 17, 2026.

Property details

Parking

Parking Information
Has Garage
Has Open Parking
# of Garage Spaces: 4
# of Covered Spaces: 4
Parking Spaces: 18
AttachedGarageYN: Yes
Parking Features: Attached, Under, Garage Door Opener, Heated Garage, Storage, Workshop in Garage, Insulated, Oversized, Paved Drive, Off Street, Paved

Interior

Master Bedroom Information
Area: 651
Length: 31
Width: 21
Level: First
Features: Bathroom - Full,Cathedral Ceiling(s),Walk-In Closet(s),Flooring - Wall to Wall Carpet,Balcony / Deck,Hot Tub / Spa,Dressing Room,Recessed Lighting

Bedroom #2 Information
Area: 414
Length: 23
Width: 18
Level: Second
Features: Bathroom - Full

Bedroom #3 Information
Area: 280
Length: 20
Width: 14
Level: Second
Features: Bathroom - Full

Bedroom #4 Information
Area: 280
Length: 20
Width: 14
Level: Second
Features: Bathroom - Full

Bedroom #5 Information
Area: 270
Length: 18
Width: 15
Level: Basement

Bathroom Information
# of Bathrooms (Full): 6
# of Bathrooms (Half): 3
Master Bathroom Features: Yes

Bathroom #1 Information
Area: 240
Length: 16
Width: 15
Features: Bathroom - Full

Living Room Information
Area: 1,024
Length: 32
Width: 32
Level: First
Features: Cathedral Ceiling(s),Beamed Ceilings,Flooring - Hardwood,Flooring - Marble,Balcony / Deck,Balcony - Exterior,Wet Bar

Family Room Information
Area: 1,024
Length: 32
Width: 32
Level: First
Features: Cathedral Ceiling(s),Flooring - Hardwood,Flooring - Wood,Balcony / Deck

Dining Room Information
Area: 441
Length: 21
Width: 21
Level: First
Features: Cathedral Ceiling(s),Beamed Ceilings,Flooring - Hardwood,Flooring - Stone/Ceramic Tile,Flooring - Marble

Kitchen Information
Area: 616
Length: 28
Width: 22
Level: First
Features: Skylight,Flooring - Stone/Ceramic Tile,Dining Area,Balcony / Deck,Kitchen Island,Deck - Exterior,Remodeled,Second Dishwasher

Office Room Information
Area: 288
Length: 18
Width: 16
Features: Skylight,Balcony / Deck

Basement Information
Basement: Full, Finished, Walk-Out Access, Interior Entry, Garage Access

Laundry Information
Laundry Features: First Floor, Gas Dryer Hookup, Washer Hookup

Fireplace Information
Has Fireplace
# of Fireplaces (Total): 6
Fireplace Features: Family Room, Living Room, Master Bedroom

Interior Features
# of Rooms (Total): 18
Door Features: Insulated Doors, French Doors
Window Features: Skylight, Insulated Windows, Screens
Flooring: Tile, Carpet, Marble, Hardwood
Interior Features: Bathroom - Full, Walk-In Closet(s), Exercise Room, Game Room, 3/4 Bath, Home Office, Sauna/Steam/Hot Tub, Wet Bar, Wired for Sound

Exterior

Building Information
Building Area (Total): 15,556
Foundation Details: Concrete Perimeter, Irregular
Construction Materials: Frame
Year Built Source: Public Records
Year Built Details: Actual
Color: Earth

Exterior Features
Fencing: Fenced
Roof: Shingle
Patio And Porch Features: Porch, Porch - Enclosed, Screened, Deck, Patio
Exterior Features: Balcony / Deck, Porch, Porch - Enclosed, Porch - Screened, Deck, Patio, Balcony, Pool - Inground Heated, Tennis Court(s), Rain Gutters, Hot Tub/Spa, Professional Landscaping, Screens, Fenced Yard, Horses Permitted, Kennel

Pool Information
Has Private Pool
Has Spa
Pool Features: Pool - Inground Heated
Spa Features: Hot Tub / Spa, Private

Property Information
PropertySubType: Single Family Residence
Green Energy Efficient : Thermostat
Security Features: Security System

Lot Information
Lot Size (Acres): 8.26
Lot Features: Wooded, Gentle Sloping
ViewYN: Has View
View: Scenic View(s)
Road Surface Type: Paved
Road Frontage Type: Public, Dead End
Road Responsibility: Public Maintained Road

Financial

Tax Information
Tax Annual Amount: $33,417.90
Tax Year: 2018

Utilities

Utility Information
Utilities: for Gas Range, for Gas Oven, for Gas Dryer, Washer Hookup, Icemaker Connection
Sewer: Private Sewer
Water Source: Private
Electric: Generator, Circuit Breakers, 200+ Amp Service

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

Location

Location Information
Directions: 310 Flagg Hill to Windermere Road. Drive up the Hill (Windermere) Gated Entrance top of the hill.
UnparsedAddress: 310 Flagg Hill Road On Windermere, Boxborough MA 01719

Community Information
Senior CommunityYN: No
Community Features: Public Transportation, Shopping, Walk/Jog Trails, Medical Facility, Conservation Area, Highway Access, House of Worship, Private School, Public School, T-Station
HorseYN: Yes

Public facts

Beds: 6
Baths: 7.5
Sq. Ft.: 7,960
Stories: 2.0
Lot Size: 8.26 acres
Style: Single Family Residential
Year Built: 1985
Year Renovated: —
County: Middlesex County
APN: 386950

Home facts updated by county records on Jul 16, 2026

Other

Listing Information
StandardStatus: Closed

Around this home

Schools

Blanchard Memorial School

Public K-6 • Assigned • 1.2mi

8/10

Raymond J Grey Junior High School

Public 7-8 • Assigned • 2.3mi

10/10

Acton-Boxborough Regional High School

Public 9-12 • Assigned • 2.3mi

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

4/10 Heat Factor

7 days above 96° expected this year, 14 days in 30 years

6/10 Wind Factor

27% chance of strong winds in next 30 years

2/10 Air Factor

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

Provided by First Street

Historical weather

Boxboro, MA • 01719

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

$2.36M – $2.85M

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New listings for sale in 01719

OPEN SUN, 11AM TO 12:30PM

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OPEN SAT, 12:30PM TO 2:30PM3D WALKTHROUGH

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Home values near 310 Flagg Hill Road On Windermere

Data from public records.

Address	Redfin Estimate
35 Ethan Allen Dr, Acton, MA 4 Beds \| 2.5 Baths \| 1960 Sq. Ft.	$862,204
39 Ethan Allen Dr, Acton, MA 4 Beds \| 2.5 Baths \| 2314 Sq. Ft.	$1,049,665

Address	Redfin Estimate
37 Ethan Allen Dr, Acton, MA 4 Beds \| 2.5 Baths \| 2268 Sq. Ft.	$1,003,981
41 Ethan Allen Dr, Acton, MA 4 Beds \| 3 Baths \| 3015 Sq. Ft.	$953,719

Address	Redfin Estimate
3 Ticonderoga Rd, Acton, MA 4 Beds \| 2.5 Baths \| 2000 Sq. Ft.	$892,787
40 Ethan Allen Dr, Acton, MA 4 Beds \| 2.5 Baths \| 2000 Sq. Ft.	$902,754

Property information provided by MLS PIN when last listed in 2017. 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 01719, MA

Sale history for 310 Flagg Hill Road On Windermere

Tax history for 310 Flagg Hill Road On Windermere

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 01719

Home values near 310 Flagg Hill Road On Windermere

More real estate resources