59 Bailey Rd, Watertown, MA 02472
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Property image
OFF MARKET

59 Bailey Rd
Watertown, MA 02472

  • 4 Beds
  • 2.5 Baths
  • 2,910 sqft (on 0.30 acres)

$2,004,600

Trulia Estimate
as of Aug 6, 2026
Est. Refi. Payment $12,057/mo*
Refinance Your Home

$2,004,600

Trulia Estimate
as of Aug 6, 2026
Est. Refi. Payment $12,057/mo*
Refinance Your Home
4 Beds
2.5 Baths
2,910 sqft
(on 0.30 acres)

Local Information

  • Map ViewExplore the area around 59 Bailey Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1923
Lot Size
0.3 acres
Living Area
2,910 sqft
Price/Sqft
$689
Parking
Garage

About this House

Oakley Country Club. Classic 1920's brick and shingle Gambrel Colonial on one of the finest streets in town. Beautifully maintained and thoughtfully expanded with an oversized first floor family room and a spacious first floor master bedroom suite, ideal for the extended family or today's modern lifestyle. Lovely period details including unspoiled millwork, fireplaces, heated sunroom, formal dining room with wainscotting and oak hardwood floors throughout. Private level back yard, sunny front mudroom and side-entrance mudroom, walk-up attic and a fantastic poured concrete basement that is ideal for a playroom or workshop. Updates included high-efficiency direct-vent gas heating system with 5 zones, 200amp electrical and full French Drain system. 1st Open House Saturday and Sunday, October 1st & 2nd from 12-2:00pm
59 Bailey Rd, Watertown, MA 02472 is a 4 bedroom, 3 bathroom, 2,910 sqft single-family home built in 1923. It last sold for $1,060,000 on Nov 30, 2016. It is currently off market. The Trulia Estimate is $2,004,600, with a rent estimate of $6,245/month.

Home Details for 59 Bailey Rd

Interior Features

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

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Brick
Parking & Garage
GarageParking: Garage Detached

Property Information

Year Built
Year Built: 1923
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 0.30 acres

Price History for 59 Bailey Rd

DatePriceEventSource
11/30/2016$1,060,000Sold
N/A
11/01/2016$1,095,000PendingAgent Provided
10/25/2016$1,095,000PriceChange
Agent Provided
09/30/2016$1,150,000Listed For SaleAgent Provided
10/05/1993$335,000Sold
N/A

Market trends in Watertown

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$780K
$59.85KMoM
Sale-to-List Price
100.1%
Price per sq ft
$535
$12MoM
Available listings
83
5MoM
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Property Tax and Assessment

Year2025
Tax$19,041
Assessment$1,630,200
Home facts updated by county records

Comparable Sales for 59 Bailey Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
22 Stoneleigh Cir, Watertown, MA
0.05
Single-Family Home
$1,126,013
09/15/25
3
1.5
2,298
43 Bailey Rd, Watertown, MA
0.03
Single-Family Home
$2,000,000
09/26/25
5
3
3,750
68 Barnard Ave, Watertown, MA
0.23
Single-Family Home
$1,350,000
12/08/25
5
4.5
4,537
23 Columbia St, Watertown, MA
0.28
Single-Family Home
$1,900,000
06/09/26
4
3
3,135
107 Stoneleigh Rd, Watertown, MA
0.22
Single-Family Home
$1,400,000
08/11/25
5
2.5
2,723
100 Garfield St, Watertown, MA
0.13
Single-Family Home
$2,050,000
08/21/25
3
3.5
2,701
32 Marcia Rd, Watertown, MA
0.27
Single-Family Home
$1,365,000
06/30/26
4
2.5
2,093
25 Barnard Ave, Watertown, MA
0.25
Single-Family Home
$1,830,000
03/31/26
4
3.5
2,906
22 Robbins Rd, Watertown, MA
0.31
Single-Family Home
$1,500,000
09/08/25
3
3
2,626
122 Garfield St, Watertown, MA
0.15
Single-Family Home
$2,650,000
07/15/26
4
3.5
4,498

Nearby homes

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Assigned Schools

These are the assigned schools for 59 Bailey 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 Watertown

At least 398 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

  • 69 % Say car is needed

  • 69 % Say there's holiday spirit

  • 65 % Say it's walkable to grocery stores

  • 61 % 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

Sourced by Trulia users. 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
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  • 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
    Flag
  • 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
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  • 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
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  • 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
    Flag
  • 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
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  • 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
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  • 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
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  • 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
    Flag
  • 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 sale near 59 Bailey Rd

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Off Market Homes Near 59 Bailey Rd

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