OFF MARKET

Off Market Jan 2023 for $1M

$1,265,564

Est. refi paymentEst. refi $1,078/mo

•

5,756

sq ft

55 Flagg Rd, Southborough, MA 01772

About this home

Are you seeking turn of the century living in the comfort of a well preserved, updated vintage home? Longtime owners w/40 years of conscientious stewardship offer a rare opportunity to own a unique piece of history on North side of Southboro*Spectacular, almost level, completely private lot w/immediate access to Town,RT9/495/Pike*Georgian center entrance combines w/Federal farmhouse: Inviting high ceilings, formal music/living room & dining room, country kitchen joined w/3-sided glass morning room flooded w/light facing views of rear paradise*Primary suite takes entire 2nd level of Federal section w/cathedral sleeping chamber & terrace overlooking IG Grecian heated pool & spa & 1.5 acre manicured landscape & offers sizeable dressing room, whirlpool & wide pine floors*3 addtl bedrooms & 1.5 baths & laundry on 2nd flr*3d flr vaulted great rm*So many special features: Butler's pantry, wine room, 8 FP, Oversized 3 car garage, potting shed, reinforced 3 story barn, glass pavilion, etc!

Single-familyProperty Type

1817Year Built

1.41 acresLot Size

$220Est. Price/Sq.Ft.

3 garage spacesParking

Listed by Andrew Abu • Andrew J. Abu Inc., REALTORS®

Bought with Kristine Wingate Shifrin • Andrew J. Abu Inc., REALTORS®

Redfin checked: a minute ago

•Source:MLS PIN #73036240

Redfin Estimate

$1,265,564

$266K since sold in January 2023$15K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 13.3% higher than the average sale price ($1.12M) of 6 comparable homes.

SOLD APR 23, 2026
$1,283,000
A
4 beds2.5 baths3,808 sq ft
14 Sarsen Stone Way, Southborough, MA 01772
SOLD JUL 8, 2026
$949,900
B
4 beds3.5 baths3,758 sq ft
44 Gilmore Rd, Southborough, MA 01772
SOLD AUG 18, 2026
$890,000
C
3 beds3 baths3,069 sq ft
1 Tara Rd, Southborough, MA 01772
SOLD APR 23, 2026
$1,250,000
D
4 beds3.5 baths5,038 sq ft
15 Jacob Amsden Rd, Westborough, MA 01581
SOLD SEP 29, 2025
$1,126,250
E
4 beds3 baths3,432 sq ft
22 High St, Southborough, MA 01772
SOLD JAN 30, 2026
$1,200,000
F
5 beds3 baths5,022 sq ft
11 Skylar Dr, Southborough, MA 01772

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Earn from this home

Sell

$455,843

Est. take-home

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Refinance

Est. cash available

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Rent

$5,079/mo

Redfin rental estimate

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Market trends in 01772, MA

Last updated August 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

100.0%

1.8% MoM

Median sale price

$982K

$218 MoM

Avg. days on market

25d

5 days MoM

Recently sold homes

1 MoM

New listings for sale

$639,900
3 beds1 bath1,540 sq ft
23 Woodbury Rd, Southborough, MA 01772
$1,199,000
3 beds3.5 baths4,416 sq ft
71 Sears Rd, Southborough, MA 01772
$1,600,000
3 beds3.5 baths3,000 sq ft
12 Wood St, Southborough, MA 01772
$564,897
2 beds1 bath1,461 sq ft
166 Southville Rd Unit A, Southborough, MA 01772
See all

Provided by Redfin

Sale history for 55 Flagg Rd

Year

Property tax

Land + Additions

Assessment*

2023

$15,508 (+15.6%)

$293,700 + $757,000

$1,050,700

2020

$13,421 (−1.3%)

$293,700 + $757,000

$1,050,700

2018

$13,601 (+3.3%)

$214,900 + $627,800

$842,700

2017

$13,166 (+1.6%)

$214,900 + $588,900

$803,800

2016

$12,964 (+2.0%)

$204,900 + $614,600

$819,500

2015

$12,707 (+7.3%)

$190,100 + $603,100

$793,200

2014

$11,847 (+1.2%)

$177,900 + $554,300

$732,200

2013

$11,712 (+1.4%)

$189,600 + $518,500

$708,100

2012

$11,548 (+4.8%)

$185,300 + $530,200

$715,500

2011

$11,014 (+2.4%)

$174,800 + $532,100

$706,900

2009

$10,760

$200,100 + $565,200

$765,300

Tax history for 55 Flagg Rd

Year

Property tax

Land + Additions

Assessment*

2023

$15,508 (+15.6%)

$293,700 + $757,000

$1,050,700

2020

$13,421 (−1.3%)

$293,700 + $757,000

$1,050,700

2018

$13,601 (+3.3%)

$214,900 + $627,800

$842,700

2017

$13,166 (+1.6%)

$214,900 + $588,900

$803,800

2016

$12,964 (+2.0%)

$204,900 + $614,600

$819,500

2015

$12,707 (+7.3%)

$190,100 + $603,100

$793,200

2014

$11,847 (+1.2%)

$177,900 + $554,300

$732,200

2013

$11,712 (+1.4%)

$189,600 + $518,500

$708,100

2012

$11,548 (+4.8%)

$185,300 + $530,200

$715,500

2011

$11,014 (+2.4%)

$174,800 + $532,100

$706,900

2009

$10,760

$200,100 + $565,200

$765,300

*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

2.5

Stories

Lot width

—

Lot depth

—

Lot size

1.41 Acres

Year renovated

—

Sq. Ft.

5,756

Year built

1700

Style

Single Family Residential

County

Worcester County

APN

1663326

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 20, 2023.

Property details

Parking

Parking Information
Has Garage
Has Open Parking
# of Garage Spaces: 3
# of Covered Spaces: 3
Parking Spaces: 10
AttachedGarageYN: Yes
Parking Features: Attached, Storage, Barn, Paved Drive, Off Street, Stone/Gravel, Paved

Interior

Master Bedroom Information
Level: Second
Features: Beamed Ceilings,Vaulted Ceiling(s),Walk-In Closet(s),Closet,Flooring - Wood,Balcony - Exterior,Deck - Exterior,Dressing Room,Gas Stove,Lighting - Overhead

Bedroom #2 Information
Level: Second
Features: Closet,Flooring - Wood

Bedroom #3 Information
Level: Second
Features: Fireplace,Closet,Flooring - Wood

Bedroom #4 Information
Level: Second
Features: Fireplace,Closet,Flooring - Wood

Bathroom Information
# of Bathrooms (Full): 2
# of Bathrooms (Half): 2
Master Bathroom Features: Yes

Bathroom #1 Information
Level: First
Features: Bathroom - Half,Flooring - Marble,Countertops - Stone/Granite/Solid,Recessed Lighting

Bathroom #2 Information
Level: Second
Features: Bathroom - Tiled With Tub & Shower,Flooring - Marble,Lighting - Sconce,Crown Molding,Pedestal Sink

Bathroom #3 Information
Level: Second
Features: Bathroom - Double Vanity/Sink,Bathroom - Tiled With Tub & Shower,Beamed Ceilings,Flooring - Wood,Jacuzzi / Whirlpool Soaking Tub,Low Flow Toilet,Cabinets - Upgraded

Living Room Information
Level: First
Features: Flooring - Hardwood,Chair Rail,Recessed Lighting,Wainscoting,Gas Stove,Crown Molding

Family Room Information
Level: First
Features: Wood / Coal / Pellet Stove,Beamed Ceilings,Flooring - Wood,French Doors,Recessed Lighting,Wainscoting

Dining Room Information
Level: First
Features: Closet/Cabinets - Custom Built,Flooring - Hardwood,French Doors,Gas Stove,Lighting - Overhead,Crown Molding

Kitchen Information
Level: First
Features: Flooring - Wood,Dining Area,Pantry,Countertops - Stone/Granite/Solid,French Doors,Kitchen Island,Breakfast Bar / Nook,Recessed Lighting,Gas Stove,Lighting - Overhead,Crown Molding

Basement Information
Basement: Full, Partially Finished, Interior Entry, Bulkhead, Sump Pump, Concrete

Laundry Information
Laundry Features: Fireplace, Laundry Closet, Flooring - Wood, Attic Access, Electric Dryer Hookup, Second Floor, Washer Hookup

Fireplace Information
Has Fireplace
# of Fireplaces (Total): 8
Fireplace Features: Family Room, Kitchen, Living Room, Master Bedroom, Bedroom

Interior Features
# of Rooms (Total): 11
Door Features: French Doors
Window Features: Storm Window(s), Screens
Flooring: Wood, Tile, Marble, Hardwood, Vinyl / VCT, Flooring - Wood, Flooring - Vinyl, Flooring - Hardwood
Interior Features: Vaulted Ceiling(s), Wainscoting, Lighting - Overhead, Bathroom - Half, Lighting - Sconce, Crown Molding, Beamed Ceilings, Study, Play Room, Bathroom, Game Room, Foyer, Walk-Up Attic, Internet Available - Broadband

Exterior

Building Information
Building Area (Total): 5,756
Foundation Details: Stone, Granite
Construction Materials: Brick, Post & Beam
Year Built Source: Owner
Year Built Details: Approximate,Renovated Since,Unknown/Mixed
Color: brick/whit

Exterior Features
Roof: Shingle
Patio And Porch Features: Deck - Roof, Deck - Wood, Patio
Exterior Features: Deck - Roof, Deck - Wood, Patio, Pool - Inground Heated, Cabana, Rain Gutters, Barn/Stable, Paddock, Professional Landscaping, Screens, Gazebo, Garden, Outdoor Shower, Stone Wall, Outdoor Gas Grill Hookup

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

Property Information
Accessibility Features: No
PropertySubType: Single Family Residence
Green Energy Efficient : Thermostat
Security Features: Security System
Other Structures: Cabana, Barn/Stable, Gazebo

Lot Information
Lot Size (Acres): 1.41
Lot Features: Corner Lot, Underground Storage Tank, Cleared, Level
Road Surface Type: Paved
Road Frontage Type: Public
Road Responsibility: Public Maintained Road

Financial

Tax Information
Tax Annual Amount: $14,551
Tax Year: 2022

Utilities

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

Heating & Cooling
Has Heating
Has Cooling
Heating: Baseboard, Steam, Oil, Propane, Pellet Stove
Cooling: Window Unit(s), Wall Unit(s), 3 or More

Location

Location Information
Directions: Take Rt 30 west of center to Deerfoot, bear R onto Flagg or take 9 West to R on Flagg
UnparsedAddress: 55 Flagg Rd, Southborough MA 01772

Community Information
Senior CommunityYN: No
Horse Amenities: Paddocks

Public facts

Beds: 5
Baths: 2.5
Sq. Ft.: 5,756
Stories: 3.0
Lot Size: 1.41 acres
Style: Single Family Residential
Year Built: 1700
Year Renovated: —
County: Worcester County
APN: 1663326

Home facts updated by county records on Jul 20, 2023

Other

Miscellaneous Information
Heat Zones: 7

Listing Information
StandardStatus: Closed

Around this home

Schools

Margaret Neary Elementary School

Public 4-5 • Assigned • 0.9mi

8/10

P. Brent Trottier Middle School

Public 6-8 • Assigned • 0.8mi

8/10

Algonquin Regional High School

Public 9-12 • Assigned • 3.6mi

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

1/10 Fire Factor

Unlikely to be 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

27% chance of strong winds in next 30 years

2/10 Air Factor

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

Provided by First Street

Historical weather

Southborough, MA • 01772

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

8.9 hrs

4.4 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$1.20M – $1.46M

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Nearby similar homes

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Lot 6 Lincoln St, Hopkinton, MA 01748

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New listings for sale in 01772

$639,900

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23 Woodbury Rd, Southborough, MA 01772

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3 beds3.5 baths4,416 sq ft

71 Sears Rd, Southborough, MA 01772

$1,600,000

3 beds3.5 baths3,000 sq ft

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Home values near 55 Flagg Rd

Data from public records.

Address	Redfin Estimate
48 Flagg Rd, Southborough, MA 4 Beds \| 1.5 Baths \| 1247 Sq. Ft.	$674,374
49 Flagg Rd, Southborough, MA 3 Beds \| 2 Baths \| 2436 Sq. Ft.	$889,692

Address	Redfin Estimate
44 Flagg Rd, Southborough, MA 3 Beds \| 2 Baths \| 1692 Sq. Ft.	$755,076
59 Flagg Rd, Southborough, MA 4 Beds \| 2.5 Baths \| 2344 Sq. Ft.	$720,888

Address	Redfin Estimate
42 Flagg Rd, Southborough, MA 4 Beds \| 2 Baths \| 1852 Sq. Ft.	$840,021
61 Flagg Rd, Southborough, MA 4 Beds \| 2.5 Baths \| 1276 Sq. Ft.	$740,190

Property information provided by MLS PIN when last listed in 2022. 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 01772, MA

Sale history for 55 Flagg Rd

Tax history for 55 Flagg Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 01772

Home values near 55 Flagg Rd

More real estate resources