20 Gregory Rd, Wakefield, MA 01880
OFF MARKET

20 Gregory Rd
Wakefield, MA 01880

Greenwood
  • 3 Beds
  • 3 Baths
  • 1,848 sqft (on 0.28 acres)

$855,500

Trulia Estimate
as of Aug 25, 2026

$855,500

Trulia Estimate
as of Aug 25, 2026
3 Beds
3 Baths
1,848 sqft
(on 0.28 acres)

Home Value

Trulia Estimate
$856K
Since last month
Decreased$8K (-0.9%)
Since last year
Increased$20K (+2.4%)
Since last sale
Increased$431K (+101.3%)
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 +67% in the last 10 years
MonthEstimated value
2026
August 2026$856K
July 2026$863K
June 2026$874K
May 2026$889K
April 2026$870K
March 2026$862K
February 2026$825K
January 2026$807K
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
29 Gregory Rd, Wakefield, MA
0.04
Single-Family Home
$776,000
09/04/25
3
2.5
1,372
11 Ludlow Ave, Wakefield, MA
0.07
Single-Family Home
$750,000
06/16/26
3
1.5
2,034
19 Fellsmere Ave, Wakefield, MA
0.16
Single-Family Home
$1,050,000
01/30/26
3
2.5
2,560
3 Fellsmere Ave, Wakefield, MA
0.12
Single-Family Home
$750,000
08/11/26
3
3
2,466
25 Fellsmere Ave, Wakefield, MA
0.19
Single-Family Home
$768,000
08/12/26
3
2
1,837
1 Ludlow Ave, Wakefield, MA
0.12
Single-Family Home
$799,000
12/30/25
3
1.5
2,944
15 Belmont Rd, Wakefield, MA
0.14
Single-Family Home
$1,300,000
04/17/26
3
2.5
3,038
24 Myrtle Ave, Wakefield, MA
0.32
Single-Family Home
$849,000
01/08/26
3
3
1,797
19 Belmont Rd, Wakefield, MA
0.14
Single-Family Home
$1,310,000
08/24/26
4
2.5
2,400
24 Gladstone St, Wakefield, MA
0.26
Single-Family Home
$900,000
02/18/26
3
1.5
1,696

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
29 Gregory Rd, Wakefield, MA 01880
0.04
$1,107,800
3
2.5
1,372
Off Market
33 Gregory Rd, Wakefield, MA 01880
0.06
$904,400
3
2.5
2,137
Off Market
16 Gregory Rd, Wakefield, MA 01880
0.02
$925,500
3
2
1,968
Off Market
37 Gregory Rd, Wakefield, MA 01880
0.08
$1,422,600
5
3.5
3,175
Off Market
30 Druid Hill Ave, Wakefield, MA 01880
0.05
$1,173,300
3
2.5
2,417
Off Market
21 Druid Hill Ave, Wakefield, MA 01880
0.05
$1,027,500
3
2.5
2,097
Off Market
8 Michael Rd, Wakefield, MA 01880
0.09
$977,200
4
2.5
2,476
Off Market
11 Ludlow Ave, Wakefield, MA 01880
0.07
$750,000
3
1.5
2,034
Recently Sold
15 Belmont Rd, Wakefield, MA 01880
0.14
$1,300,000
3
2.5
3,038
Recently Sold
19 Belmont Rd, Wakefield, MA 01880
0.14
$1,310,000
4
2.5
2,400
Recently Sold
21 Bonair Ave, Wakefield, MA 01880
0.11
$752,800
3
1
1,383
Off Market
6 Gerry Ln, Wakefield, MA 01880
0.15
$829,200
3
2
1,945
Off Market

Local Information

  • Map ViewExplore the area around 20 Gregory Rd.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1961
Lot Size
0.28 acres
Living Area
1,848 sqft
Price/Sqft
$463
Parking
Garage

About this House

Lovely Raised Ranch in excellent area of Greenwood. Kitchen and baths are older but are in nice condition. Fireplaced living room and fireplaced famly room. Screened porch is in back (unheated). Roof was new in 2010 and chimney rebuilt at same time from roof line up. New gutters and paint in 2010. See Amenities Sheet for property details.
20 Gregory Rd, Wakefield, MA 01880 is a 3 bedroom, 3 bathroom, 1,848 sqft single-family home in Greenwood, built in 1961. It last sold for $425,000 on Jun 29, 2012. It is currently off market. The Trulia Estimate is $855,500, with a rent estimate of $3,992/month.

Home Details for 20 Gregory Rd

Interior Features

Interior Details
BasementNumber of Rooms: 6
Heating & Cooling
Heating: OilHeating Fuel: Oil
Levels, Entrance, & Accessibility
Stories: 1
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1961Year Updated: 1970
Property Type / Style
Property Type: Single Family HomeArchitecture: ranch

Community

Units in Building: 1

Lot Information

Lot Area: 0.28 acres

Price and Tax history

DateEventPrice
Jan 29, 2013
Source: Agent Provided
ListingRemoved
$439,900
Jan 5, 2013
Source: Agent Provided
Listed For Sale
$439,900
Jun 29, 2012
Source: N/A
Sold
$425,000
Jan 24, 2012
Source: Agent Provided
Listed For Sale
$439,900

Market trends in Wakefield

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$809K
$3.25KMoM
Sale-to-List Price
—
Price per sq ft
$490
$22MoM
Available listings
56
2MoM

Around this home

Neighborhood Overview

Greenwood
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Greenwood

At least 19 Trulia users voted on each feature.

  • 100 % Say it's dog friendly

  • 97 % Say there's holiday spirit

  • 96 % Say parking is easy

  • 96 % Say kids play outside

  • 89 % Say they plan to stay for at least 5 years

  • 88 % Say people would walk alone at night

  • 86 % Say there are sidewalks

  • 83 % Say it's walkable to restaurants

  • 83 % Say streets are well-lit

  • 80 % Say yards are well-kept

  • 75 % Say neighbors are friendly

  • 73 % Say car is needed

  • 71 % Say it's quiet

  • 56 % Say there are community events

  • 52 % Say there's wildlife

  • 29 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "been here 6 years and my neighbors and the neighborhood is the best. We all watch out for one another. It is a very peaceful area and very safe."
    0
    Flag
  • Trulia User
    "digs and walkers are always around. very friendly and secure neighborhood. everyone looks out for each other."
    0
    Flag
  • Trulia User
    "Dog owners love this neighborhood low traffic, and plenty of sidewalk space plenty of places to let the dog off the leash and run parks etc"
    0
    Flag
  • Trulia User
    "Many families in the area, with great fields, parks, and stores within walking distance. All this but still private little neighborhoods."
    0
    Flag
  • Trulia User
    "Lots of people walk their dogs around. Always friendly. Nice fields to let them loose in. Everyone is respectful"
    0
    Flag
  • Kaitlyn S.
    "Halloween is a big event . Every house is a party . My husband and I know just about everyone on our street!! We have bbq and fires with the neighbors all summer ."
    0
    Flag
  • Kaitlyn S.
    "I’ve lived in this area for 5 years now . It’s like it’s own tiny community. Everyone is very friendly and knows one another . The elementary school is excellent and the commuter rail in a walk away "
    0
    Flag
  • Sam C.
    "We are huge dog lovers and there are great places to take them for long walks."
    0
    Flag
  • Sam C.
    "The commute is very simple. There are many different ways you can use to get to the heart of Greenwood."
    0
    Flag
  • Sam C.
    "It is a small little community within a bigger town."
    0
    Flag
  • Sam C.
    "It is a GREAT place to raise kids and the school is an awesome place to learn."
    0
    Flag
  • Rebecca R.
    "We do like dogs."
    0
    Flag
  • Rebecca R.
    "It's very beautiful with nice people."
    0
    Flag
  • David S.
    "There are lots of areas to walk dogs in Greenwood, and there is access to 20 acres of town owned. Ther are woods that you can access through the playground. Veterinary services are available in Wakefield, Melrose, Stoneham, Saugus, and Reading, and most are only a few miles from Greenwood."
    0
    Flag
  • David S.
    "The rail and bus service can take you to Boston and the easy access to major highways makes commuting easy."
    0
    Flag
  • David S.
    "Quiet area, friendly neighbors, suburban bordering on rural, not crowded, lots of small businesses, but no heavy industry. Lots of trees, nice homes and scenery. Easy access to major highways, lots of places to eat or shop, no crime, fire station nearby, prompt police response if needed, & good roads. Also, local bank has a Greenwood office, and you don't have to go far to find what you need. Just a nice environment to live in. Plus, rail service to Boston, and to points North as well."
    0
    Flag
  • David S.
    "It is NOT a rough neighborhood, nor any criminal activity here. Children are safe here. We all look out for each other. Preschool and grammar school are centrally located, and bus service is provided."
    0
    Flag
  • Huyen N.
    "Beautiful wood areas with many hiking trails. Generally quiet and pretty safe neighborhood with nice neighbors."
    0
    Flag
  • Jennifer
    "Lakes, friendly, clean, close to major highways, good schools, amazing restaurants, youth sports, lovely people "
    0
    Flag
  • Ruth J.
    "Very dog friendly and most people pick up after their dogs. There is also a dog park on Main Street and when I drive by, I always look to see if anyone is there and it puts a smile on my face."
    0
    Flag
  • Ruth J.
    "Very easy to get by through any means of transportation. There is a bus line and the commuter rail and I've been seeing a lot of bike riding."
    0
    Flag
  • Ruth J.
    "There's Greenwood Plaza which has much to offer."
    0
    Flag
  • Ruth J.
    "The school system is very good. They also have Kumon Learning Center, which I sent my two children to for math and reading comprehension."
    0
    Flag
  • Ehlocke
    "I actually know my neighbors. Kids walk to school together. I get a text if I leave my garage door open. Very friendly area. "
    0
    Flag
  • Mj S.
    "Desirable Greenwood neighborhood is walkable and family friendly. Wonderful neighborhood community. Walking distance (5-10 minutes) to Greenwood Station commuter rail to downtown Boston. Town plows sidewalk in front of house. "
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 20 Gregory Rd

  • What is 20 Gregory Rd estimated to be worth?
    Trulia's estimated value for 20 Gregory Rd in Wakefield, MA is $855,500.
  • What is the price history for 20 Gregory Rd?
    20 Gregory Rd in Wakefield, MA last sold for $425,000 in June 2012.
  • Is Wakefield a buyer's or seller's market?
    Wakefield is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Wakefield?
    The median sale price in Wakefield is $809K. That is up $3.25K from the prior month.
  • How big is the lot at 20 Gregory Rd?
    The lot at 20 Gregory Rd in Wakefield, MA is about 0.28 acres (12,166 sq ft).
  • Does 20 Gregory Rd have a garage?
    Yes, 20 Gregory Rd in Wakefield, MA has a garage.

Explore by feature - Pet Friendly

16 pet-friendly rentals in Wakefield, MA

Explore by feature - Garage

10 rentals with a garage in Wakefield, MA

Explore by feature - Air Conditioning

25 rentals with air conditioning in Wakefield, MA

Explore by feature - Washer/dryer

27 rentals with a washer/dryer in Wakefield, MA

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 20 Gregory Rd

Skip to last item
Skip to first item

Homes for sale near 20 Gregory Rd

Skip to last item
Skip to first item
Skip to last item
  • Results are loading
Skip to first item