14 Winthrop Rd, Wellesley, MA 02482
Property image
Property image
OFF MARKET

14 Winthrop Rd
Wellesley, MA 02482

  • 4 Beds
  • 2.5 Baths
  • 2,481 sqft (on 0.33 acres)

$2,620,700

Trulia Estimate
as of Jul 5, 2026
Est. Refi. Payment $15,171/mo*
Refinance Your Home

$2,620,700

Trulia Estimate
as of Jul 5, 2026
Est. Refi. Payment $15,171/mo*
Refinance Your Home
4 Beds
2.5 Baths
2,481 sqft
(on 0.33 acres)

Local Information

  • Map ViewExplore the area around 14 Winthrop Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Character and opportunity abound in this 1929 brick, colonial-farmhouse on long-admired Dana Hall cul-de-sac. Details of the era including fireplaced-living room with original built-ins and dramatic light. Marble & stainless kitchen, beautiful hardwood floors and fabulous mud room. Expansion potential and privacy all overlooking the scenic Brook Path. Walk to town, train, schools and Wellesley College. Enjoy the combination of lush, quiet, natural environment with in-town feel at the "split rock"! Come see the possibilities.
14 Winthrop Rd, Wellesley, MA 02482 is a 4 bedroom, 3 bathroom, 2,481 sqft single-family home built in 1929. It last sold for $1,385,000 on Oct 27, 2015. It is currently off market. The Trulia Estimate is $2,620,700, with a rent estimate of $7,360/month.

Home Highlights

Parking
No Info
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 14 Winthrop Rd

Interior Features

Heating & Cooling
Heating: Other, GasAir ConditioningHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 7
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1929
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Exterior Features

Exterior Home Features
Exterior: Brick

Community

Units in Building: 1

Lot Information

Lot Area: 0.33 acres

Price History for 14 Winthrop Rd

DatePriceEventSource
10/27/2015$1,385,000Sold
N/A
08/21/2015$1,499,000PendingAgent Provided
06/12/2015$1,499,000PriceChange
Agent Provided
06/03/2015$1,525,000Listed For SaleAgent Provided
10/24/2014$1,100,000Sold
N/A

Market trends in Wellesley

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
111
3MoM
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Property Tax and Assessment

Year2025
Tax$20,498
Assessment$1,994,000
Home facts updated by county records

Comparable Sales for 14 Winthrop Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
145 Grove St, Wellesley, MA
0.19
Single-Family Home
$1,560,000
08/04/25
4
2.5
2,054
29 Denton Rd, Wellesley, MA
0.35
Single-Family Home
$1,520,000
10/16/25
4
2.5
2,956
57 Cottage St, Wellesley, MA
0.19
Single-Family Home
$1,525,000
12/01/25
3
1.5
1,522
3 Midland Rd, Wellesley, MA
0.18
Single-Family Home
$1,405,000
03/30/26
5
3
2,630
194 Grove St, Wellesley, MA
0.26
Single-Family Home
$2,600,000
08/21/25
4
2.5
3,620
29 Brook St, Wellesley, MA
0.64
Single-Family Home
$1,730,000
08/15/25
4
3
2,405
16 Denton Rd, Wellesley, MA
0.39
Single-Family Home
$2,400,000
06/11/26
5
2.5
3,176
4 Arden Rd, Wellesley, MA
0.32
Single-Family Home
$2,300,000
07/15/25
5
3.5
4,826
4 Hampden St, Wellesley, MA
0.60
Single-Family Home
$1,951,000
07/21/25
4
2.5
2,860
20 Arden Rd, Wellesley, MA
0.35
Single-Family Home
$3,000,000
04/28/26
5
3.5
2,875

Nearby homes

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Assigned Schools

These are the assigned schools for 14 Winthrop Rd.
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
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  • 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
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  • 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
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  • 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
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  • 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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Homes for sale near 14 Winthrop Rd

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Off Market Homes Near 14 Winthrop Rd

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