53 Gregory Rd, Holliston, MA 01746
OFF MARKET

$772,300

Trulia Estimate
  • 3 Beds
  • 2.5 Baths
  • 2,830 sqft (on 0.46 acres)

53 Gregory Rd, Holliston, MA 01746

Est. Refi. Payment $4,642/mo*
Refinance Your Home
Currently Off Market - Sold Aug 15, 2018 for $421,000

Home Value

Trulia Estimate
$772K
Since last month
Decreased$12K (-1.6%)
Since last year
Increased$20K (+2.7%)
Since last sale
Increased$353K (+83.8%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +60% in the last 10 years
MonthEstimated value
2026
August 2026$774K
August 2026$774K
July 2026$786K
June 2026$785K
May 2026$796K
April 2026$779K
March 2026$776K
February 2026$743K
January 2026$738K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
99 Goulding St, Holliston, MA
0.17
Single-Family Home
$673,550
04/24/26
3
2.5
1,624
31 Cold Spring Rd, Holliston, MA
0.19
Single-Family Home
$640,000
07/10/26
4
2
1,793
154 Holly Ln, Holliston, MA
0.31
Single-Family Home
$837,000
06/18/26
4
3
2,397
563 Norfolk St, Holliston, MA
0.33
Single-Family Home
$675,000
05/29/26
4
1.5
1,728
36 Appleyard Ln, Holliston, MA
0.38
Single-Family Home
$650,000
09/24/25
3
1.5
1,391
110 Goulding St, Holliston, MA
0.16
Single-Family Home
$1,240,000
07/15/26
4
3
3,727
54 Shaw Farm Rd, Holliston, MA
0.33
Single-Family Home
$560,000
08/05/26
2
1.5
1,008
140 Goulding St, Holliston, MA
0.19
Single-Family Home
$1,070,000
07/27/26
4
3
4,130
128 Goulding St, Holliston, MA
0.17
Single-Family Home
$1,051,000
07/09/26
4
3
3,889
625 Norfolk St, Holliston, MA
0.23
Single-Family Home
$642,500
02/06/26
3
2
1,772

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
40 Alden Rd, Holliston, MA 01746
0.06
$660,900
3
2.5
1,744
Off Market
36 Gregory Rd, Holliston, MA 01746
0.06
$611,100
3
1
1,248
Off Market
35 Dudley Rd, Holliston, MA 01746
0.10
$819,500
4
2.5
2,379
Off Market
9 Gregory Rd, Holliston, MA 01746
0.12
$697,000
3
1.5
1,086
Off Market
19 Alden Rd, Holliston, MA 01746
0.13
$703,600
3
2.5
1,876
Off Market
120 Goulding St, Holliston, MA 01746
0.15
-
5
6
6,134
Off Market
15 Dudley Rd, Holliston, MA 01746
0.12
$667,200
4
2.5
1,641
Off Market
110 Goulding St, Holliston, MA 01746
0.16
$1,240,000
4
3
3,727
Recently Sold
128 Goulding St, Holliston, MA 01746
0.17
$1,051,000
4
3
3,889
Recently Sold
53 Goulding St, Holliston, MA 01746
0.15
$713,500
3
2
1,968
Off Market
99 Goulding St, Holliston, MA 01746
0.17
$673,550
3
2.5
1,624
Recently Sold
140 Goulding St, Holliston, MA 01746
0.19
$1,070,000
4
3
4,130
Recently Sold

Local Information

  • Map ViewExplore the area around 53 Gregory Rd.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1963
0.46 acre lot
2,830 sqft
$273/sqft

About this House

Don't miss this opportunity to own a meticulously maintained split-level home located on a quiet tree lined street in a pristine Holliston neighborhood. Gourmet kitchen w/cathedral ceiling, Cherry cabinets, Quartz countertops, stainless appliances, a gas cooktop including pot filler, an 8x4 island & full-length glass door leading to the wrap-around deck & backyard oasis perfect for outdoor entertaining. This home features a decorative fireplace in the living room, crown molding, newly finished hardwood floors throughout & three generous-sized bedrooms. Freshly painted, low maintenance vinyl siding, double pane vinyl windows, 50 gal stainless H20 heater, 3 zone gas (a/c ready) hepa heating system & a full finished lower level with a wood burning stove that is a perfect private space for in-law use or a teen suite. All bathrooms have been updated. Just minutes from restaurants, shops & public transportation. No showings until OH Sun 7/1 from 1-3 pm.
53 Gregory Rd, Holliston, MA 01746 is a 3 bedroom, 3 bathroom, 2,830 sqft single-family home built in 1963. It last sold for $421,000 on Aug 15, 2018. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $772,300, with a rent estimate of $4,044/month.

Home Details for 53 Gregory Rd

Interior Features

Heating & Cooling
Heating: Forced Air, OilAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1
Interior Details
Number of Rooms: 7
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood

Property Information

Year Built
Year Built: 1963Year Updated: 2006
Property Type / Style
Property Type: Single Family HomeArchitecture: ranch

Lot Information

Lot Area: 0.46 acres

Price and Tax history

DateEventPrice
Aug 15, 2018
Source: N/A
Sold
$421,000
Jul 3, 2018
Source: Agent Provided
Pending
$399,900
Jun 29, 2018
Source: Agent Provided
Listed For Sale
$399,900
Jun 30, 1995
Source: N/A
Sold
$157,500
Mar 7, 1989
Source: N/A
Sold
$158,000

Market trends in Holliston

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$679K
Sale-to-List Price
—
Price per sq ft
$375
Available listings
31
9MoM

Around this home

What Locals Say about Holliston

At least 47 Trulia users voted on each feature.

  • 94 % Say it's dog friendly

  • 93 % Say parking is easy

  • 89 % Say car is needed

  • 85 % Say kids play outside

  • 83 % Say it's quiet

  • 81 % Say there's holiday spirit

  • 78 % Say there's wildlife

  • 77 % Say yards are well-kept

  • 73 % Say people would walk alone at night

  • 72 % Say neighbors are friendly

  • 68 % Say they plan to stay for at least 5 years

  • 56 % Say there are sidewalks

  • 54 % Say there are community events

  • 47 % Say streets are well-lit

  • 33 % Say it's walkable to restaurants

  • 26 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Jayne J.
    "This neighborhood has tons of dogs and kids. A great place to walk your dog. Sidewalks and wood trails are close by. "
    5
    Flag
  • Mglwood
    "Our school district is progressive and does not teach to the test. Instead we teach our kids to think!"
    0
    Flag
  • Molly M.
    "The town encourages kids to play in sports summer camp at the lake . The town has a fabulous school system with school choice."
    1
    Flag
  • Molly M.
    "A quite neighborhood with many children, we have a neighborhood block party once a year. Lake Winthrop is across the street"
    0
    Flag
  • Molly M.
    "Block parties and trick or treat adult get together, as well as neighborhood watch and the proximity to the Lake and all that goes along with that,summer camp and swimming lesson."
    0
    Flag
  • tylerrdunnn
    "everyone knows everyone and we are a tight knit community. there may not be the fanciest stores, or the best night life, but its a very cute town with lots to do, recommended to families and singles, lots of variety in home sizes and styles as well"
    0
    Flag
  • Owner
    "Private but neighborly. Wild grasses, hills trees surround well maintained and large lots, which themselves surround a terrific fishing pond. Estate like setting but with down to earth people."
    1
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 53 Gregory Rd

  • What is 53 Gregory Rd estimated to be worth?
    Trulia's estimated value for 53 Gregory Rd in Holliston, MA is $772,300.
  • What is the price history for 53 Gregory Rd?
    53 Gregory Rd in Holliston, MA last sold for $421,000 in August 2018.
  • Is Holliston a buyer's or seller's market?
    Holliston is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Holliston?
    The median sale price in Holliston is $679K.
  • How big is the lot at 53 Gregory Rd?
    The lot at 53 Gregory Rd in Holliston, MA is about 0.46 acres (20,037 sq ft).

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