40 Winter St, Natick, MA 01760
OFF MARKET

40 Winter St
Natick, MA 01760

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

$2,444,000

Trulia Estimate
as of May 18, 2026
Est. Refi. Payment $14,542/mo*
Refinance Your Home

$2,444,000

Trulia Estimate
as of May 18, 2026
Est. Refi. Payment $14,542/mo*
Refinance Your Home
4 Beds
5 Baths
5,200 sqft
(on 1.31 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

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.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

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 History for 40 Winter St

DatePriceEventSource
06/13/2014$1,345,000Sold
N/A
02/12/2014$1,350,000Listed For SaleAgent Provided
12/21/2000$1,250,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax$23,233
Assessment$1,942,600
Home facts updated by county records

Comparable Sales for 40 Winter St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
9 Oak Hill Rd, Natick, MA
0.19
Single-Family Home
$1,660,000
07/31/25
5
4.5
4,200
3 Rathbun Rd, Natick, MA
0.28
Single-Family Home
$1,429,000
08/25/25
4
2.5
3,413
3 Jennison Cir, Natick, MA
0.09
Single-Family Home
$2,200,000
08/29/25
8
6.5
8,000
3 Drumlin Rd, Weston, MA
0.46
Single-Family Home
$3,199,000
07/22/25
5
4.5
6,930
1 Winter St, Natick, MA
0.46
Single-Family Home
$1,475,000
01/30/26
4
4.5
3,809
6 Hickory Rd, Natick, MA
0.57
Single-Family Home
$1,530,000
08/07/25
4
3.5
3,686
242 Oak St, Natick, MA
0.50
Single-Family Home
$1,785,000
06/26/25
5
5
4,546
17 Smokey Hill Rd, Wayland, MA
0.68
Single-Family Home
$1,660,000
12/02/25
4
3
3,660
12 Cabot St, Natick, MA
0.19
Single-Family Home
$945,000
06/13/25
4
3
2,312
12 Nancy Rd, Natick, MA
0.29
Single-Family Home
$950,000
02/04/26
3
2.5
2,200

Assigned Schools

These are the assigned schools for 40 Winter St.
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 Natick

At least 180 Trulia users voted on each feature.

  • 91 % Say it's dog friendly

  • 86 % Say parking is easy

  • 81 % Say car is needed

  • 79 % 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

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
    Flag
  • 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
    Flag
  • 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
    Flag
  • Michelly Petroni
    "Everything Natick is wonderful I loved every second i lived there. You will have everything around your house"
    0
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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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40 Winter St, Natick, MA 01760 is a 4 bedroom, 5 bathroom, 5,200 sqft single-family home built in 2000. This property is not currently available for sale. 40 Winter St was last sold on Jun 13, 2014 for $1,345,000. The current Trulia Estimate for 40 Winter St is $2,444,000.