27 Jackson Rd, Wellesley, MA 02481
OFF MARKET

27 Jackson Rd
Wellesley, MA 02481

  • 5 Beds
  • 3 Baths
  • 4,500 sqft (on 0.34 acres)

$2,442,600

Trulia Estimate
as of Aug 16, 2026
Est. Refi. Payment $14,618/mo*
Refinance Your Home

$2,442,600

Trulia Estimate
as of Aug 16, 2026
Est. Refi. Payment $14,618/mo*
Refinance Your Home
5 Beds
3 Baths
4,500 sqft
(on 0.34 acres)

Home Value

Trulia Estimate
$2.44M
Since last month
Decreased$42K (-1.7%)
Since last year
Increased$27K (+1.1%)
Since last sale
Increased$1M (+156.8%)
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 +68% in the last 10 years
MonthEstimated value
2026
August 2026$2.44M
July 2026$2.46M
June 2026$2.48M
May 2026$2.47M
April 2026$2.43M
March 2026$2.41M
February 2026$2.32M
January 2026$2.27M
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
42 Jackson Rd, Wellesley, MA
0.07
Single-Family Home
$1,625,000
06/04/26
3
2.5
1,996
78 Hunnewell St, Wellesley, MA
0.27
Single-Family Home
$1,930,000
01/02/26
5
4.5
4,043
14 Hunnewell St, Needham, MA
0.26
Single-Family Home
$2,165,000
11/05/25
4
4.5
4,691
15 Standish Cir, Wellesley, MA
0.32
Single-Family Home
$2,833,000
05/19/26
4
3.5
4,151
21 Madison Rd, Wellesley, MA
0.33
Single-Family Home
$2,130,000
08/03/26
4
3.5
2,609
70 Briarwood Cir, Needham, MA
0.42
Single-Family Home
$2,325,000
05/08/26
5
4.5
4,281
310 Oakland St, Wellesley, MA
0.26
Single-Family Home
$3,125,000
02/20/26
6
5.5
5,993
34 Sheridan Rd, Wellesley, MA
0.21
Single-Family Home
$1,250,000
08/03/26
3
1.5
1,478
98 Hunnewell St, Needham, MA
0.42
Single-Family Home
$2,625,000
01/30/26
5
5.5
4,881
22 Standish Rd, Wellesley, MA
0.52
Single-Family Home
$1,525,000
08/03/26
3
2.5
2,290

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
24 Jackson Rd, Wellesley, MA 02481
0.03
$3,690,500
6
4.5
5,317
Off Market
42 Jackson Rd, Wellesley, MA 02481
0.07
$1,625,000
3
2.5
1,996
Recently Sold
48 Jackson Rd, Wellesley, MA 02481
0.08
$2,360,400
4
2.5
3,674
Off Market
282 Oakland St, Wellesley, MA 02481
0.19
$1,235,700
3
2
1,859
Off Market
287 Oakland St, Wellesley, MA 02481
0.20
$2,543,000
5
5
4,800
Off Market
34 Sheridan Rd, Wellesley, MA 02481
0.21
$1,250,000
3
1.5
1,478
Recently Sold
19 Sheridan Rd, Wellesley, MA 02481
0.22
$3,936,500
5
5.5
6,240
Off Market
29 Sheridan Rd, Wellesley, MA 02481
0.22
$2,707,200
4
3.5
3,815
Off Market
36 Sheridan Rd, Wellesley, MA 02481
0.23
$3,130,700
5
4.5
5,496
Off Market
14 Hunnewell St, Needham, MA 02494
0.26
$2,165,000
4
4.5
4,691
Recently Sold
310 Oakland St, Wellesley, MA 02481
0.26
$3,125,000
6
5.5
5,993
Recently Sold
392 Wellesley Ave, Wellesley, MA 02481
0.29
$1,611,400
4
2
2,247
Off Market

Local Information

  • Map ViewExplore the area around 27 Jackson Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1946
Lot Size
0.34 acres
Living Area
4,500 sqft
Price/Sqft
$543
Parking
Garage

About this House

This single-family home is located at 27 Jackson Rd, Wellesley, MA. 27 Jackson Rd is in Wellesley, MA and in ZIP code 02481. This property has 5 bedrooms, 3 bathrooms and approximately 4,500 sqft of floor space. This property has a lot size of 0.34 acres and was built in 1946.
27 Jackson Rd, Wellesley, MA 02481 is a 5 bedroom, 3 bathroom, 4,500 sqft single-family home built in 1946. It last sold for $950,000 on Aug 12, 2004. It is currently off market. The Trulia Estimate is $2,442,600, with a rent estimate of $7,737/month.

Home Details for 27 Jackson Rd

Interior Features

Interior Details
BasementNumber of Rooms: 12Types of Rooms: Walk In Closet, Breakfast Nook, Dining Room, Family Room, Master Bath, Mud Room
Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Appliances & Utilities
DishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: WoodLawnPatioSprinkler System
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1946Year Updated: 2014
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 0.34 acres

Price and Tax history

DateEventPrice
Aug 12, 2004
Source: N/A
Sold
$950,000

Market trends in Wellesley

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$2.15M
$161KMoM
Sale-to-List Price
100.6%
0.4%MoM
Price per sq ft
$666
$18MoM
Available listings
87
25MoM
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Around this home

View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Wellesley

At least 124 Trulia users voted on each feature.

  • 92 % Say it's dog friendly

  • 87 % Say parking is easy

  • 85 % Say people would walk alone at night

  • 84 % Say yards are well-kept

  • 80 % Say car is needed

  • 79 % Say there are sidewalks

  • 76 % Say kids play outside

  • 75 % Say there's holiday spirit

  • 74 % Say streets are well-lit

  • 73 % Say there's wildlife

  • 72 % Say it's quiet

  • 70 % Say they plan to stay for at least 5 years

  • 67 % Say it's walkable to restaurants

  • 66 % Say neighbors are friendly

  • 65 % Say there are community events

  • 63 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Mike Holiday
    "Everyone walks their dogs and lets their dogs say hello, most often. People know each other. It’s a great community"
    0
    Flag
  • Emilyperrottet
    "Nothing. It’s a changing neighborhood with a mix of old and new homes. Most of the homes are old and run down. "
    0
    Flag
  • Emilyperrottet
    "I take the Commuter rail from Wellesley to the T subway. 1.5 hours to Cambridge from south station. "
    0
    Flag
  • Trulia User
    "Lots of trails and other dogs in the area, many pet stores in the area as well. Dogs are well behaved and friendly. "
    0
    Flag
  • Shirley L.
    "The walking paths and yearly town celebrations are wonderful! A great sense of community and great schools. "
    0
    Flag
  • Sdipietro369
    "I am a visitor to this area. The neighborhood seems very nice with Babson College right around the corner. Shops within a close distance. "
    3
    Flag
  • Katrina C.
    "You feel you're kids are safe here in town. Everyone is friendly and we're all neighbors. It's a lovely town with a community feeling. "
    2
    Flag
  • Jamie.solomon1
    "I lived in Weston for two years and it’s a delightful town, with gorgeous land and large houses. Usually at least an acre"
    1
    Flag
  • Cmt138
    "Great access to commuter rail from either Wellesley Square or Wellesley Hills. Easy 10-15 min walk. Better parking from Wellesley Square. Usually takes about 1/2 hour to Back Bay. Driving into Boston can take a little more time with traffic to cross town to Mass Pike."
    2
    Flag
  • Laura M.
    "There are lots of dogs in our neighborhood- people walk them all the time. Dogs are welcome at Morse’s pond in the off season. "
    1
    Flag
  • Bruce C.
    "Lots of other dog owners who walk their dogs all the time. Also plenty of space to run with dogs on a trail or away from streets. "
    1
    Flag
  • Keith S.
    "Lots of trails and public spaces. Nationally acclaimed colleges. Variety of great shops and restaurants."
    0
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  • Srodousakis
    "Wellesley is a beautiful but very privileged neighborhood. It is very safe and people are friendly. Schools are great! There is a cute downtown and generally it’s a great place to raise kids. "
    0
    Flag
  • Molly R.
    "i love my neighborhood. everyone is so kind and welcoming. we often times have little gatherings or block parties. everyone knows each other and we are a very close community. "
    0
    Flag
  • Victoria V.
    "That I live on route 16 and nobody lets me out of my driveway in the morning and I have to leave for work an hour early just because of that."
    0
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Apartments for Rent

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Explore by feature - Pet Friendly

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Homes for sale near 27 Jackson Rd

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Off Market Homes Near 27 Jackson Rd

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Frequently asked questions about 27 Jackson Rd

  • What is 27 Jackson Rd estimated to be worth?
    Trulia's estimated value for 27 Jackson Rd in Wellesley, MA is $2,442,600.
  • What is the price history for 27 Jackson Rd?
    27 Jackson Rd in Wellesley, MA last sold for $950,000 in August 2004.
  • Is Wellesley a buyer's or seller's market?
    Wellesley is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Wellesley?
    The median sale price in Wellesley is $2.15M. That is up $161K from the prior month.
  • Does 27 Jackson Rd have air conditioning?
    Yes, 27 Jackson Rd in Wellesley, MA has air conditioning.
  • Does 27 Jackson Rd have laundry facilities?
    Yes, 27 Jackson Rd in Wellesley, MA has in-unit laundry.