59 Winsor Ave, Watertown, MA 02472
OFF MARKET

59 Winsor Ave
Watertown, MA 02472

  • 3 Beds
  • 3 Baths
  • 2,053 sqft

$1,297,600

Trulia Estimate
as of May 5, 2026
Est. Refi. Payment $7,478/mo*
Refinance Your Home

$1,297,600

Trulia Estimate
as of May 5, 2026
Est. Refi. Payment $7,478/mo*
Refinance Your Home
3 Beds
3 Baths
2,053 sqft

Homes for sale near 59 Winsor Ave

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Local Information

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

Description

On a tree lined street in the much-desired Oakley Country Club area sits this charming Dutch Colonial. Sun streams into this home casting a warm glow onto the gumwood moldings, built-ins and hardwood floors. The eat-in brand new kitchen has granite countertop, tiled, and all new top end stainless steel appliances. This house boasts a gracious, formal dining room, a spacious 24' living room with built-ins and a spectacular sunroom/family room that is flanked on three sides by walls of windows. Among the three bedrooms on the second floor is a 21' master with two closets and a newly build full en suite bathroom. This house has been impeccably updated while losing none of its original charm. Some updates since 2004 include, new roof, new windows, fence, new electrical system, alarm system, stainless appliances, new entry door and granite steps. Updates since 2010 include new hot water tank, new plumbing, fully renovated half bath, main bathroom, a new en suite bathroom in the master bedroom, all new indoor doors, a brand new kitchen with all new top end appliances, hardwood floors throughout the house. This is a lovely one of a kind gem!
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
No Info
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 59 Winsor Ave

Interior Features

Interior Details
BasementAtticNumber of Rooms: 7Types of Rooms: Breakfast Nook, Dining Room, Family Room, Laundry Room, Master Bath, Mud Room, Office, Pantry, Sun RoomCeiling Fan
Heating & Cooling
Heating: Radiant, GasHeating Fuel: Radiant
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Appliances & Utilities
Cable ReadyDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace
Windows, Doors, Floors & Walls
Double Paned Windows
Security
Security System

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: VinylGardenLawn
Parking & Garage
GarageParking Space: 1Parking: Garage Detached

Property Information

Year Built
Year Built: 1915Year Updated: 2011
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 2

Lot Information

Lot Area: 4800 sqft

Price History for 59 Winsor Ave

DatePriceEventSource
08/20/2011$599,000ListingRemovedAgent Provided
10/14/2010$594,000Sold
N/A
08/21/2010$599,000Listed For SaleAgent Provided
06/28/2004$591,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax$11,961
Assessment$1,024,100
Home facts updated by county records

Comparable Sales for 59 Winsor Ave

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
504 Mount Auburn St, Watertown, MA
0.15
Single-Family Home
$840,000
07/23/25
3
1.5
1,796
267 School St, Watertown, MA
0.12
Single-Family Home
$1,475,000
09/15/25
5
2.5
2,735
52 Hillside Rd, Watertown, MA
0.06
Single-Family Home
$1,450,000
05/22/25
4
2.5
2,710
27 Appleton St, Watertown, MA
0.15
Single-Family Home
$1,249,000
11/05/25
5
3.5
2,738
437 Mount Auburn St, Watertown, MA
0.24
Single-Family Home
$1,500,000
05/16/25
3
3.5
2,900
12 Carver Rd, Watertown, MA
0.20
Single-Family Home
$1,400,000
03/12/26
5
2.5
2,935
47 Stults Rd, Belmont, MA
0.40
Single-Family Home
$1,675,000
06/13/25
3
2.5
2,006
61 Oakley Rd, Watertown, MA
0.32
Single-Family Home
$875,000
07/09/25
4
2
1,625
11 Arthur Ter, Watertown, MA
0.22
Single-Family Home
$850,000
07/17/25
2
2
1,294
20 Pequossette Rd, Belmont, MA
0.51
Single-Family Home
$1,150,000
08/08/25
3
2
2,135

Assigned Schools

These are the assigned schools for 59 Winsor Ave.
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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 Watertown

At least 397 Trulia users voted on each feature.

  • 91 % Say there are sidewalks

  • 88 % Say it's dog friendly

  • 81 % Say parking is easy

  • 77 % Say it's walkable to restaurants

  • 76 % Say people would walk alone at night

  • 74 % Say streets are well-lit

  • 70 % Say there's holiday spirit

  • 69 % Say car is needed

  • 65 % Say it's walkable to grocery stores

  • 62 % Say kids play outside

  • 59 % Say yards are well-kept

  • 56 % Say neighbors are friendly

  • 56 % Say it's quiet

  • 49 % Say there's wildlife

  • 46 % Say they plan to stay for at least 5 years

  • 29 % Say there are community events

Learn more about our methodology.
  • Joetacheck
    "Everyone is in bed by 9pm. It’s eerily quiet at night. I hardly ever see my neighbors. Not even the ones that live in my apartment. "
    0
    Flag
  • Tirson.pena
    "Watertown is a good town to live in , very safe and clean a friendly community. There a lot of activities and events that happen every year "
    0
    Flag
  • Trisha Timpug
    "I’ve lived in Watertown for four years on and off. I absolutely love it! The neighborhood is clean, friendly, and safe. Lots of hidden gems in the neighborhood for restaurants. The biking trail is perfect for my dogs. Watertown will always have a special place in my heart."
    0
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  • Maryam Akbari
    "I live in this area for more than 20 years and I am and my family safe, and Watertown is Multicultural and the all restaurants from different culture are here, you can meet people from all unique backgrounds and cultures, these are all the reasons "
    0
    Flag
  • Trulia User
    "It’s a beautiful area full of seasonal activities and nice people. I love all the businesses and eateries. "
    0
    Flag
  • Trulia User
    "Lots of local shops, arsenal yards is a nice area to go and the paths along the river are nice spaces to visit. "
    0
    Flag
  • Mike S
    "We live near great walking paths so it’s convenient for dog owners. There are no dog parks in this neighborhood. "
    0
    Flag
  • Trulia User
    "I hardly have a hall mile to drive to work and most days it takes 15-20 minutes. Most days I could walk quicker, but I’m super lazy so I don’t."
    1
    Flag
  • Trulia User
    "there are a lot of parks and a couple dog parks nearby. there are also lots of rabbits to chase. there's great night life for dogs and plenty of options for coffee. lots of good workspaces for dogs that telecommute "
    3
    Flag
  • Trulia User
    "I don't have a dog but there are large yards and lots of parks for dog walkers. and bunnies which i think dogs probably like"
    0
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  • Alicia B.
    "plenty of parks and sidewalks to walkand play with your dog. plenty of other dogs in the neighborhood and people are friendly with your dogs"
    2
    Flag
  • Donna C.
    "Sense of community and safety old town feel I’m most neighborhoods, small businesses still airing the area "
    0
    Flag
  • Michelle D.
    "I’ve grown up here and love it. Easy proximity to the city but with kore space! Lots of families and dogs!"
    0
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  • Kenia M.
    "Loved this place, looking for apartment, quiet city, lovely peoples, just love and live here for many years "
    0
    Flag
  • Alicia B.
    "lots of dogs, common areas and walking paths. many dog owners in the neighborhood who pick up after their dogs"
    0
    Flag
  • Annette
    "This neighborhood is great. We watch out for each other like a little family. Everyone is super friendly and easy to talk to. "
    0
    Flag
  • Taylorcassamas F.
    "nice parks getting to be a little crowded. sleepy little town turning into Cambridge. increase in local traffic as results."
    0
    Flag
  • Alia B.
    "Great community. Safe area for families and children. Many public transportation routes including express busses to boston."
    0
    Flag
  • Annetta J. W.
    "I've lived in this neighborhood for a handful of months, it's quiet, and people are kind. We feel safe, people have been helpful as well as kind. "
    0
    Flag
  • Natalia
    "Neighbors helping each other with snow removal. People are respectful and quiet for the most part. A lot of people walking their dogs or out with their kids....great place to live!"
    1
    Flag
  • Aliza P.
    "It’s great, tons of nice and friendly people! Good schools. I think it’s perfect for a new family. There are places to show within half mile, walking distance."
    0
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  • Tina P.
    "Love the feel of the neighborhood. Close to Boston. Also close to plenty of stores and restaurants and shops, but far enough away from downtown to still have a neighborhood feel. very safe feel. definitely love all of the older homes"
    8
    Flag
  • Ilana Z.
    "easy access to downtown Boston and other parts of the city and surrounding areas. weekend buses can be scarce sometimes so plan ahead."
    0
    Flag
  • AnaH
    "It’s a great place to live , family environment, clean neighborhood and several parks and good restaurants around. "
    0
    Flag
  • Joe E.
    "Springer and summer time events like fairs and things like that on the Weekends are very attractive. I used to live on Arlington street Watertown where there are many things to do: go to gym, ride a bike, playing soccer, walk around the park, and many other things. "
    0
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  • Monica
    "Lots of public transit and family friendly. There are many young families which make this a good place to raise young children. "
    0
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  • Paul p.
    "The dog park , dogs walking around the neighborhood with out being leashed not going out too when it can jump the gates Or the fences themselves m going after other dogs or other people in the neighborhood "
    1
    Flag
  • Flomostudio
    "Beautiful homes. Great stores. Cafes and bakeries. Quiet, safe, perfect and close to Harvard square and T line "
    0
    Flag
  • Katie B.
    "Greek festival every summer, Armenian festival, all the food festivals are great and highlight all this great neighborhood has to offer "
    0
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  • Yudith0214
    "my neighborhood has very good access to public transportation is a very nice, clean and quite and very good for you to walk your dog, friendly neighbors."
    1
    Flag
  • David S.
    "East watertown is centrally located between two bus lines, easy to get to Harvard, lots of shopping, parks, and good family neighborhood "
    0
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Homes for rent near 59 Winsor Ave

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Off Market Homes Near 59 Winsor Ave

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59 Winsor Ave, Watertown, MA 02472 is a 3 bedroom, 3 bathroom, 2,053 sqft single-family home built in 1915. This property is not currently available for sale. 59 Winsor Ave was last sold on Oct 14, 2010 for $594,000. The current Trulia Estimate for 59 Winsor Ave is $1,297,600.