14 HIGHLAND DR
Valuation
Tax & Assessment
Climate Risk
Scores 0–100; higher = greater projected risk.
Property Facts
Transaction History(3)
Sales and refinances filed with the county for this home. Not every transfer is a normal sale, so check the type before comparing prices.Assigned SchoolsThe public schools this address is zoned for. Boundaries change, so confirm with the district before you count on it.
District: Berkshire Hills School District
Neighborhood · ZIP 01230These are comparison scores, not percentages. 100 equals the national average, so 150 means about 50% above average.
Index scale: 100 = US average (tick). Lower is better.
Owner Tools
Data by ATTOM. Valuations are automated estimates, not appraisals. Photos from Google Street View and may not depict the current property state.
How this home compares
14 Highland Dr measured against every home in its neighborhood, its ZIP code and its county, using county assessor records refreshed nightly. A home can stand out in one of those areas and look ordinary in another, because each one holds a different mix of homes.
- Worth more than 87% of homes in Berkshire County
- Costs more per square foot than 78% of homes in Berkshire County
- Bigger than 77% of homes in Berkshire County
- Newer than 70% of homes in Berkshire County
What homes are worth in Great Barrington 01230
Each bar is how many homes fall in that price range. The marker is this home.
This home is worth more than 63% of homes in Great Barrington 01230.
How it measures up in Great Barrington 01230
The dot is this home. The mark in the middle is the typical home in Great Barrington 01230.
Pricier than 63% of homes nearby
Pricier than 38% of homes nearby
Bigger than 69% of homes nearby
Bigger than 39% of homes nearby
Newer than 59% of homes nearby
| Measure | This home | Great Barrington 01230 | Berkshire County |
|---|---|---|---|
| Estimated valuepricier than | $798,210 | 63% of homes | 87% of homes |
| Price per ft²pricier than | $341 | 38% of homes | 78% of homes |
| Living areabigger than | 2,344 ft² | 69% of homes | 77% of homes |
| Lot sizebigger than | 0.91 ac | 39% of homes | 62% of homes |
| Year builtnewer than | 1974 | 59% of homes | 70% of homes |
About 14 Highland Dr
How much is 14 Highland Dr, Great Barrington, MA worth?
The TopHap Estimate for 14 Highland Dr, Great Barrington, MA is $798,210 as of Sep 24, 2026. The likely range is $714,538 to $881,882. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.
When did 14 Highland Dr, Great Barrington, MA last sell?
14 Highland Dr, Great Barrington, MA last sold on Oct 31, 2005 for $420,000, according to the county's recorded deed.
How big is 14 Highland Dr, Great Barrington, MA?
14 Highland Dr, Great Barrington, MA has 4 bedrooms, 2 bathrooms, 2,344 square feet of living space and a 0.91-acre lot.
When was 14 Highland Dr, Great Barrington, MA built?
14 Highland Dr, Great Barrington, MA was built in 1974, making it 52 years old. It is a colonial home. The building has 2 stories.
What schools serve 14 Highland Dr, Great Barrington, MA?
14 Highland Dr, Great Barrington, MA is assigned to Monument Valley Regional Middle School (middle), rated C+; Muddy Brook Regional Elementary School (elementary), rated A; Monument Mountain Regional High School (high), rated C+. All sit in Berkshire Hills School District. Attendance boundaries change — confirm with the district before relying on an assignment.
How does 14 Highland Dr, Great Barrington, MA compare to other homes in Great Barrington 01230?
Among the 4,687 homes in Great Barrington 01230, it is worth more than 63% of them ($798,210 against a typical $655,686), its price per square foot is higher than 38% of them ($341 against a typical $375), it is bigger than 69% of them (2,344 ft² against a typical 1,868 ft²), its lot is bigger than 39% of them (0.91 ac against a typical 1.32 ac) and it is newer than 59% of them (1974 against a typical 1962). Measured against all of Berkshire County, it is worth more than 87% of homes there. These shares are recounted nightly from the full county assessor record for each area, not from active listings.
What are the property taxes on 14 Highland Dr, Great Barrington, MA?
The 2025 property tax bill for 14 Highland Dr, Great Barrington, MA was $8,431. The county assessed it at $611,400.
More homes on Highland Dr
- 4 Highland Dr$912K3 bd · 2 ba · 1,750 ft² · Sold Jan 2026
- 11 Highland Dr$615K3 bd · 2 ba · 1,533 ft² · Sold $550K · Jan 2025
- 15 Highland Dr$938K4 bd · 3 ba · 2,328 ft² · Sold $720K · Aug 2023
- 12 Highland Dr$675K3 bd · 1 ba · 1,370 ft² · Sold $250K · Oct 2021
- 19 Highland Dr$1M3 bd · 2.5 ba · 2,096 ft² · Sold $585K · Jan 2021
- 10 Highland Dr$1.6M5 bd · 4 ba · 3,430 ft² · Sold $1M · Oct 2020
- 16 Highland Dr$1M5 bd · 4 ba · 1,896 ft² · Sold $655K · Sep 2020
- 7 Highland Dr$811K4 bd · 3 ba · 2,596 ft² · Sold $425K · Dec 2015
- 2 Highland Dr$932K4 bd · 3 ba · 2,682 ft² · Sold $428K · May 2012
- 9 Highland Dr$574K3 bd · 2 ba · 1,144 ft² · Sold Aug 2010
- 8 Highland Dr$750K4 bd · 3 ba · 1,866 ft² · Sold $269K · Feb 2005
- 5 Highland Dr$849K4 bd · 3 ba · 2,080 ft² · Sold $347K · Jun 2004
Closest homes
- 16 Highland Dr$1M167 ft · 5 bd · 4 ba · 1,896 ft² · Sold $655K · Sep 2020
- 12 Highland Dr$675K198 ft · 3 bd · 1 ba · 1,370 ft² · Sold $250K · Oct 2021
- 7 Haley Rd292 ft · 3 bd · 3 ba · 2,352 ft² · Sold $275K · Jan 2021
- 17 Highland Dr$777K247 ft · 3 bd · 2 ba · 1,568 ft²
- 19 Highland Dr$1M252 ft · 3 bd · 2.5 ba · 2,096 ft² · Sold $585K · Jan 2021
- 15 Highland Dr$938K301 ft · 4 bd · 3 ba · 2,328 ft² · Sold $720K · Aug 2023
- 10 Highland Dr$1.6M391 ft · 5 bd · 4 ba · 3,430 ft² · Sold $1M · Oct 2020
- 21 Highland Dr$680K344 ft · 3 bd · 2 ba · 1,400 ft²
More homes in Great Barrington 01230
- 298 Park St$620K4 bd · 3.5 ba · 1,814 ft² · Sold $620K · Sep 2026
- 44c Mt Washington Rd$400K2 bd · 1 ba · 1,044 ft² · Sold $345K · Sep 2026
- 250 Long Pond Rd$6M9 bd · 5 ba · 11,714 ft² · Sold $6M · Sep 2026
- 117 Creamery Rd$1.3M4 bd · 3 ba · 2,156 ft² · Sold $1.3M · Sep 2026
- 905 West Rd$1.2M3 bd · 2.5 ba · 2,204 ft² · Sold $1.2M · Sep 2026
- 386 N Plain Rd$370K2 bd · 1 ba · 1,092 ft² · Sold $370K · Sep 2026
- 34 Fairview Ter$289K3 bd · 1.5 ba · 960 ft² · Sold $274K · Sep 2026
- 34 Millard Rd$2.7M4 bd · 4.5 ba · 3,185 ft² · Sold $2.7M · Sep 2026
- 18 Westminster Rd$687K4 bd · 3 ba · 1,930 ft² · Sold $140K · Sep 2026
- 18 Hilltop Rd$1.7M4 bd · 2.5 ba · 1,504 ft² · Sold $1.7M · Sep 2026
- 42 Mt Washington Rd$379K3 bd · 1.5 ba · 1,364 ft² · Sold $379K · Sep 2026
- 506 Main St4 bd · 2 ba · 2,498 ft² · Sold $225K · Sep 2026
Assigned schools
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