66 Winter St, Natick, MA 01760
OFF MARKET

66 Winter St
Natick, MA 01760

  • 4 Beds
  • 3 Baths
  • 2,532 sqft (on 1.05 acres)

$1,279,600

Trulia Estimate
as of Jul 23, 2026
Est. Refi. Payment $7,609/mo*
Refinance Your Home

$1,279,600

Trulia Estimate
as of Jul 23, 2026
Est. Refi. Payment $7,609/mo*
Refinance Your Home
4 Beds
3 Baths
2,532 sqft
(on 1.05 acres)

Local Information

  • Map ViewExplore the area around 66 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
1978
Lot Size
1.05 acres
Living Area
2,532 sqft
Price/Sqft
$505
Parking
Garage

Description

Country cape on lovely flat wooded acre.
Gorgeous state scenic road with many high end homes.
Down the street from the Weston border.
Front garden with hemlock privacy.
Large flat backyard.

Neighborhood Description

Winter Street is a gorgeous winding state scenic road that dates back to the 1700's. The 1738 Jennison Farm is just up the street as is a 19th Century farmhouse. The excellent Rivers private school is down the street in Weston. We have beautiful Nonesuch Pond with a community pond association for summer swimming.
66 Winter St, Natick, MA 01760 is a 4 bedroom, 3 bathroom, 2,532 sqft single-family home built in 1978. It last sold for $630,000 on Aug 8, 2012. It is currently off market. The Trulia Estimate is $1,279,600, with a rent estimate of $5,744/month.

Home Details for 66 Winter St

Interior Features

Interior Details
BasementAtticIn-law unitNumber of Rooms: 8Types of Rooms: Walk In Closet, Dining Room, Family Room, Master Bath, Office
Heating & Cooling
Heating: Baseboard, Forced Air, OilAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2Floors: Carpet, Hardwood
Appliances & Utilities
Cable ReadyDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace
Windows, Doors, Floors & Walls
Double Paned Windows

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Shingle, WoodGardenLawnPatioPorch
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 1978Year Updated: 2009
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Community

Units in Building: 1

Lot Information

Lot Area: 1.05 acres

Price History for 66 Winter St

DatePriceEventSource
08/08/2012$630,000Sold
N/A
06/07/2012$647,900PriceChange
Agent Provided
04/05/2012$659,000Listed For SaleAgent Provided
07/10/1996$292,500Sold
N/A

Market trends in Natick

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$836K
$13KMoM
Sale-to-List Price
100.8%
Price per sq ft
$473
$2MoM
Available listings
104
19MoM
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Property Tax and Assessment

Year2025
Tax$11,953
Assessment$999,400
Home facts updated by county records

Comparable Sales for 66 Winter St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
3 Rathbun Rd, Natick, MA
0.17
Single-Family Home
$1,429,000
08/25/25
4
2.5
3,413
34 Clubhouse Ln, Wayland, MA
0.52
Single-Family Home
$915,000
08/12/25
3
3
2,104
43 Sherburn Cir, Weston, MA
0.47
Single-Family Home
$1,700,000
06/10/26
3
2.5
2,554
12 Nancy Rd, Natick, MA
0.38
Single-Family Home
$950,000
02/04/26
3
2.5
2,200
7 Linn Ln, Wayland, MA
0.60
Single-Family Home
$825,000
04/14/26
3
3
1,566
5 Wayland Hills Rd, Wayland, MA
0.74
Single-Family Home
$1,140,000
07/07/26
4
2.5
2,522
9 Oak Hill Rd, Natick, MA
0.08
Single-Family Home
$1,660,000
07/31/25
5
4.5
4,200
16 Wayland Hills Rd, Wayland, MA
0.66
Single-Family Home
$1,365,000
06/27/26
4
2.5
2,964
6 Briar Ln, Natick, MA
0.08
Single-Family Home
$2,350,000
06/04/26
5
6.5
5,000
4 Hickory Rd, Natick, MA
0.59
Single-Family Home
$775,000
06/25/26
4
2
1,757

Nearby homes

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Assigned Schools

These are the assigned schools for 66 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

  • 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
    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
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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
    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
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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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Apartments for Rent

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Explore by feature - Pet Friendly

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Homes for sale near 66 Winter St

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Off Market Homes Near 66 Winter St

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