Showing Sat/Sun 12-2pm. Luxurious, Hopkinton Highlands estate nestled on 5.79 bucolic acres featuring 13 rooms, 4+ beds, 5.5 baths over 6200 sq. ft. of living. $600K of improvements! New Chef's kitchen w oversized breakfast bar, high-end appliances, Wolf gas cooking, steam/conv ovens, radiant heated floors & wall of windows opening to stunning yard, like no other. Sunken family room w custom gas-burning stone fireplace & built-ins. 1st fl office/bedroom w adjacent 1/2 bath. Hubbardton Forge lighting, detailed millwork, solid core doors/hardware & custom speakers. Four en suite bedrooms w walk-in closets/private baths. Posh walkout LL w 9' ceil, kitchen, wine cellar, family room w gas fireplace, bed/bath, workout area w infrared sauna, game room & sound-proof music studio. Amazing Outdoor Living! Bluestone patio, gas kitchen, bar & fireplace, pastoral grounds, 2+ acre invis. dog fence & your own trail system. Moments to Hop. State Park, Southboro Rail & top schools. Tranquility awaits
Award winning design Coventry Federal Coln with everything you want in a home 5+ privt acres around grand brick-front home w/ 3-car garage. Many amenities & upgrades such as double staircase, 2nd entry to kitchen & laundry, sunny breakfast area & well appointed kitchen, 1st floor office & sunken living room. Expansive Master ste has private den w/coffered ceiling, walk-in closet, & spacious master bath. 9 foot ceilings through-out 1st & 2nd floors. Additional bedrooms have own full bath
Year
Property tax
Land + Additions
Assessment*
2025
$29,449 (+5.2%)
$527,100 + $1,549,700
$2,076,800
2024
$28,002 (+60.3%)
$504,400 + $1,412,200
$1,916,600
2023
$17,470 (+1.4%)
$424,700 + $680,300
$1,105,000
2022
$17,236 (+2.8%)
$390,300 + $621,800
$1,012,100
2021
$16,769 (+4.1%)
$380,700 + $601,100
$981,800
2020
$16,112 (+0.8%)
$372,900 + $585,000
$957,900
2019
$15,990 (+4.2%)
$348,900 + $582,400
$931,300
2018
$15,342 (+3.1%)
$342,800 + $565,000
$907,800
2017
$14,885 (+1.2%)
$335,000 + $551,000
$886,000
2016
$14,704
$328,400 + $535,000
$863,400
2015
$14,704 (+3.4%)
$320,200 + $498,500
$818,700
2014
$14,222 (+21.0%)
$320,200 + $486,500
$806,700
2013
$11,752 (−0.2%)
$296,200 + $382,300
$678,500
2012
$11,778 (+1.9%)
$308,300 + $382,500
$690,800
2011
$11,557 (+1.8%)
$308,300 + $382,500
$690,800
2010
$11,354 (−19.3%)
$336,300 + $384,100
$720,400
2009
$14,061
$463,000 + $472,500
$935,500
Tax history for 5 Overlook Rd
Year
Property tax
Land + Additions
Assessment*
2025
$29,449 (+5.2%)
$527,100 + $1,549,700
$2,076,800
2024
$28,002 (+60.3%)
$504,400 + $1,412,200
$1,916,600
2023
$17,470 (+1.4%)
$424,700 + $680,300
$1,105,000
2022
$17,236 (+2.8%)
$390,300 + $621,800
$1,012,100
2021
$16,769 (+4.1%)
$380,700 + $601,100
$981,800
2020
$16,112 (+0.8%)
$372,900 + $585,000
$957,900
2019
$15,990 (+4.2%)
$348,900 + $582,400
$931,300
2018
$15,342 (+3.1%)
$342,800 + $565,000
$907,800
2017
$14,885 (+1.2%)
$335,000 + $551,000
$886,000
2016
$14,704
$328,400 + $535,000
$863,400
2015
$14,704 (+3.4%)
$320,200 + $498,500
$818,700
2014
$14,222 (+21.0%)
$320,200 + $486,500
$806,700
2013
$11,752 (−0.2%)
$296,200 + $382,300
$678,500
2012
$11,778 (+1.9%)
$308,300 + $382,500
$690,800
2011
$11,557 (+1.8%)
$308,300 + $382,500
$690,800
2010
$11,354 (−19.3%)
$336,300 + $384,100
$720,400
2009
$14,061
$463,000 + $472,500
$935,500
*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.
Public record
Beds
4
Baths
5.5
Stories
2
Lot width
—
Lot depth
—
Lot size
5.79 Acres
Year renovated
2020
Sq. Ft.
4,381
Year built
2003
Style
Single Family Residential
County
Middlesex County
APN
4383505
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Jul 16, 2026.
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, Paved Drive, Off Street, Paved
UnparsedAddress: 5 Overlook Road, Hopkinton MA 01748
Community Information
Senior CommunityYN: No
Community Features: Public Transportation, Shopping, Pool, Tennis Court(s), Park, Walk/Jog Trails, Stable(s), Golf, Medical Facility, Bike Path, Conservation Area, Highway Access, Private School, Public School, T-Station, University
Public facts
Beds: 4
Baths: 5.5
Sq. Ft.: 4,381
Stories: 2.0
Lot Size: 5.79 acres
Style: Single Family Residential
Year Built: 2003
Year Renovated: 2020
County: Middlesex County
APN: 4383505
Home facts updated by county records on Jul 16, 2026
Other
Miscellaneous Information
Heat Zones: 3
Listing Information
Exclusions: Washer And Dryer.
StandardStatus: Closed
Around this home
Schools
Elmwood Elementary School
Public 2-3 • Assigned • 2.3mi
9/10
Hopkinton Middle School
Public 6-8 • Assigned • 2.9mi
9/10
Hopkinton High School
Public 9-12 • Assigned • 3.0mi
10/10
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, 15 days in 30 years
6/10 Wind Factor
40% 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
Hopkinton, MA • 01748
Average low and high temperatures (°F)
32
19
35
20
50
31
60
40
68
50
80
60
84
65
80
58
74
55
63
45
51
35
37
23
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
$2.11M – $2.56M
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