40 Winter St, Natick, MA 01760
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Property image
OFF MARKET

40 Winter St
Natick, MA 01760

  • 4 Beds
  • 5 Baths
  • 5,200 sqft (on 1.31 acres)

$2,395,000

Trulia Estimate
as of Aug 15, 2026
Est. Refi. Payment $14,315/mo*
Refinance Your Home

$2,395,000

Trulia Estimate
as of Aug 15, 2026
Est. Refi. Payment $14,315/mo*
Refinance Your Home
4 Beds
5 Baths
5,200 sqft
(on 1.31 acres)

Home Value

Trulia Estimate
$2.4M
Since last month
Decreased$55K (-2.2%)
Since last year
Increased$29K (+1.2%)
Since last sale
Increased$1M (+77.7%)
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$2.39M
July 2026$2.41M
June 2026$2.45M
May 2026$2.44M
April 2026$2.42M
March 2026$2.42M
February 2026$2.33M
January 2026$2.3M
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
6 Briar Ln, Natick, MA
0.18
Single-Family Home
$2,350,000
06/04/26
5
6.5
5,000
3 Rathbun Rd, Natick, MA
0.28
Single-Family Home
$1,429,000
08/25/25
4
2.5
3,413
1 Winter St, Natick, MA
0.46
Single-Family Home
$1,475,000
01/30/26
4
4.5
3,809
16 Wayland Hills Rd, Wayland, MA
0.58
Single-Family Home
$1,365,000
06/27/26
4
2.5
2,964
17 Smokey Hill Rd, Wayland, MA
0.68
Single-Family Home
$1,660,000
12/02/25
4
3
3,660
43 Sherburn Cir, Weston, MA
0.58
Single-Family Home
$1,700,000
06/10/26
3
2.5
2,554
5 Wayland Hills Rd, Wayland, MA
0.64
Single-Family Home
$1,140,000
07/07/26
4
2.5
2,522
12 Nancy Rd, Natick, MA
0.29
Single-Family Home
$950,000
02/04/26
3
2.5
2,200
58 Rice Rd, Wayland, MA
0.78
Single-Family Home
$2,045,000
04/07/26
4
5.5
4,587
7 Whitney Cir, Natick, MA
0.58
Single-Family Home
$1,480,000
07/30/26
4
3
2,818

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
1 Jennison Cir, Natick, MA 01760
0.06
$2,034,900
5
3.5
4,504
Off Market
42 Winter St, Natick, MA 01760
0.04
$2,262,300
5
4.5
6,500
Off Market
6 Nonesuch Dr, Natick, MA 01760
0.10
$2,055,400
5
4.5
4,950
Off Market
72 Winter St, Natick, MA 01760
0.15
$1,508,300
4
3.5
3,480
Off Market
13 Oak Hill Rd, Natick, MA 01760
0.16
$1,237,900
4
2.5
2,930
Off Market
304 Pondview Pl, Tyngsboro, MA 01879
0.16
$394,700
2
1.5
1,586
Off Market
6 Briar Ln, Natick, MA 01760
0.18
$2,350,000
5
6.5
5,000
Recently Sold
9 Oak Hill Rd, Natick, MA 01760
0.19
$1,640,900
5
4.5
4,200
Off Market
28 Winter St, Natick, MA 01760
0.23
$1,105,600
4
3.5
2,800
Off Market
74 Winter St, Natick, MA 01760
0.20
$1,204,100
4
2.5
2,261
Off Market
12 Cabot St, Natick, MA 01760
0.19
$951,300
4
3
2,312
Off Market
26 Winter St, Natick, MA 01760
0.25
$1,048,100
4
2.5
4,284
Off Market

Local Information

  • Map ViewExplore the area around 40 Winter St.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2000
Lot Size
1.31 acres
Living Area
5,200 sqft
Price/Sqft
$461
Parking
Garage

About this House

Amazing newer home sited on over an acre of sweeping lawns, majestic trees and specimen plantings. Elegant interior detailing with 30 foot entry ceiling and dramatic staircase and hardwood floors throughout. Gracious formal rooms, banquet size dining room with bay windows overlooking professional landscaped back yard and gazebo, library/home office, gourmet kitchen with large center island and separate pantry. Family room stone fireplace, and custom cabinetry. Enchanting master suite with sitting area, gas fireplace and spa like bathroom with fireplace. Three additional bedrooms, one en suite, one with Jack and Jill bathroom and laundry room, great room/media room with vaulted ceilings. Lower level of approx. 2000 SF with media/rec room, exercise room, wine cellar, wine tasting area, large pantry and full bath. A traditional home built for today's lifestyle. Integrated sound system, large deck off kitchen and family room, 3 car garage, central air, central vac and security system.
40 Winter St, Natick, MA 01760 is a 4 bedroom, 5 bathroom, 5,200 sqft single-family home built in 2000. It last sold for $1,345,000 on Jun 13, 2014. It is currently off market. The Trulia Estimate is $2,395,000, with a rent estimate of $7,964/month.

Home Details for 40 Winter St

Interior Features

Heating & Cooling
Heating: Forced Air, GasAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 11
Fireplace & Spa
Fireplace

Exterior Features

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

Property Information

Year Built
Year Built: 2000
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 1.31 acres

Price and Tax history

DateEventPrice
Jun 13, 2014
Source: N/A
Sold
$1,345,000
Feb 12, 2014
Source: Agent Provided
Listed For Sale
$1,350,000
Dec 21, 2000
Source: N/A
Sold
$1,250,000

Market trends in Natick

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$841K
$5.33KMoM
Sale-to-List Price
101.1%
0.3%MoM
Price per sq ft
$477
$3MoM
Available listings
81
23MoM
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Around this home

What Locals Say about Natick

At least 180 Trulia users voted on each feature.

  • 90 % Say it's dog friendly

  • 86 % Say parking is easy

  • 81 % Say car is needed

  • 80 % Say there are sidewalks

  • 77 % Say yards are well-kept

  • 76 % Say people would walk alone at night

  • 76 % Say kids play outside

  • 72 % Say there's holiday spirit

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

  • 66 % Say it's quiet

  • 60 % Say there's wildlife

  • 58 % Say streets are well-lit

  • 56 % Say neighbors are friendly

  • 52 % Say it's walkable to restaurants

  • 50 % Say it's walkable to grocery stores

  • 49 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Claudia Sigler
    "Is a great town but overpriced. Schools are good, everything’s is close. It is a great location overall and safe "
    0
    Flag
  • Regina silva
    "I like the neighborhood, is safe and secure to walk all time at st, the people are so nice and friendly "
    0
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  • Marievetter
    "I drive pretty much everywhere I need to go. Public transportation is not a viable option for where I live. The drive is often on very congested roads, especially Speen Street."
    0
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  • Dlandry
    "I don’t know what dog owners would like or not like about living in this neighborhood. But I do know that cat owners like living here."
    0
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  • Michelly Petroni
    "Everything Natick is wonderful I loved every second i lived there. You will have everything around your house"
    0
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  • Maura Cusick
    "Natick is a lovely family friendly community teeming with events, local gatherings, and local activities. Nice access to parks & wildlife yet Convenient to transit to boston. Beautiful library. "
    1
    Flag
  • Trulia User
    "Very quiet dead end road, wonderful forest and nature trails at the end of the road. Close to all shopping destinations, awesome location. Yet still very quiet and surrounded by nature"
    2
    Flag
  • Paul A.
    "Natick Days on the common. The sensible school system and well run town government host many community events."
    2
    Flag
  • Ed J.
    "Great community and friendly neighbors, down to earth, too. Network is also very centrally located and therefore makes it easy to get anywhere in New England"
    1
    Flag
  • Clwagner1
    "Nice and quiet place to live. Good neighbors. Good schools.nice downtown. Community events, good restaurants, close to public transportation "
    1
    Flag
  • Ed J.
    "Dogs being walked all the time. If you own a dog and you live in this neighborhood I think you’ll both be very happy"
    3
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  • Ed J.
    "Living here is like living in Mayberry. We’ve been here 20 years and have loved every minute of it. Very fine schools and reasonable property taxes, too."
    2
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  • Andrea.danilowicz
    "I take the train each morning and it’s very convenient. There’s great restaurants in the area and can be quiet, yet vibrant. "
    0
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  • Katie .
    "It’s very quiet, no matter the time of year. I like living near all the hiking trails and being so close to the commuter rail. Route 9 can be busy during certain times of day. "
    1
    Flag
  • Redmen vs Flyers ‘07
    "I live in the area, there are many families that live around here. There are some great hiking areas in nearby towns. Majority of families have dogs. Kids play in the street. No street lights to speak of. Some areas are unsidewalked. Very small town feel about everything."
    4
    Flag
  • Mahashraya S.
    "Natick is the best of both worlds with a residential feel but with lots to do nearby. It’s also convenient to get groceries and necessities nearby with Natick Mall being just a stone’s throw from the neighborhood."
    0
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  • Jasonnewberg19
    "Drive into Boston. Quite horrific on most days and it will only get worse once school starts. Have to leave around 6:30/6:45am to beat most of the AM rush hour. "
    3
    Flag
  • Zuribel D. M.
    "I absolutely love Natick, prices are high for rent but the schools are awasome. The library is great."
    3
    Flag
  • Zuribel D. M.
    "Quiet and secure neighborhood, public places are clean and secure, good for kids of all ages. Good for walking and public transportation is near by."
    3
    Flag
  • Shopkerri
    "Awful going east unless you leave at 5:50 AM and come back at 3. Very congested. I have become a home body!"
    0
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  • Jondeso0743
    "I have lived in this neighborhood for 50 years..Friendly neighbors, easy access to shopping, Roache Bros. supermarket is 3/10th. of a mile from house..Lovely residential area."
    5
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  • Cupham
    "It’s a great place for dogs. You always see someone out walking their pup. It’s a great way to meet people. My dog loves it here. "
    1
    Flag
  • Gferrelli
    "Great community. Good, hardworking people. Very down to earth people. A great place to raise a family. "
    2
    Flag
  • Mrosenberg
    "This neighborhood is located near several great schools! It is close to the supermarket, major roads and is about thirty minutes from Boston. "
    2
    Flag
  • Mauricio U.
    "small town and friendly people. the area is safe and family friendly. most people have pets, which makes it easy to have a pet around people. "
    4
    Flag
  • Nicholas56
    "Gorgeous house on street of victorian beauties in the historic area known as Walnut Hill. Love to take walks here. Close to train, town and the well regarded Walnut Hill School."
    0
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  • Unspecified
    "This area is PERFECT for families! Cross street is easy walking distance to Natick Center where there is always something going on. Restaurants, ice cream parlors, church, coffee shops, and library are just a few things that are close by. The area is great for taking the dog for a walk, with many families doing the same, there is always someone new for your dog to sniff!"
    0
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  • Taylors
    "We have lived here for 7 years and love the closeness and walkability to downtown shops and parks. A close community with lots of artists and music, farmers market and summer concerts. Schools are exceptional. Commuter rail to Boston is right in downtown. We don't want to go anywhere else."
    0
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Homes for sale near 40 Winter St

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Off Market Homes Near 40 Winter St

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Frequently asked questions about 40 Winter St

  • What is 40 Winter St estimated to be worth?
    Trulia's estimated value for 40 Winter St in Natick, MA is $2,395,000.
  • What is the price history for 40 Winter St?
    40 Winter St in Natick, MA last sold for $1,345,000 in June 2014.
  • Is Natick a buyer's or seller's market?
    Natick is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Natick?
    The median sale price in Natick is $841K. That is up $5.33K from the prior month.
  • How big is the lot at 40 Winter St?
    The lot at 40 Winter St in Natick, MA is about 1.3 acres.
  • Does 40 Winter St have a garage?
    Yes, 40 Winter St in Natick, MA has a garage.