27 Chicago Ave, Bay Shore, NY 11706
OFF MARKET

27 Chicago Ave
Bay Shore, NY 11706

  • 5 Beds
  • 4 Baths

$749,200

Trulia Estimate
as of May 25, 2026
Est. Refi. Payment $4,897/mo*
Refinance Your Home

$749,200

Trulia Estimate
as of May 25, 2026
Est. Refi. Payment $4,897/mo*
Refinance Your Home
5 Beds
4 Baths

Local Information

Map showing home location
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-- mins to
Commute Destination

Description

Islip Schools! 5 Bedroom 3.5 Bath Colonial Built In 2001. Centrally Located On Private & Peaceful Cul De Sac. Hardwood Floors, Large Master Bedroom With Master Bath, 4 Bedrooms, Large Full Bath Upstairs, Eik, Dr, Lr, Den W/ Sliding Glass Doors To Yard, 2 Car Garage Attached, Full Finished Basement W/ Inside & Outside Entrance & Great Backyard! Open House Sat 2/12/11 12-2Pm
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
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Outdoor
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HOA
None
Price/Sqft
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Listed
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Home Details for 27 Chicago Ave

Property Information

Year Built
Year Built: 2001
Property Type / Style
Property Type: Single Family Home

Price History for 27 Chicago Ave

DatePriceEventSource
02/14/2011$369,999ListingRemovedAgent Provided
01/31/2011$369,999Listed For SaleAgent Provided
09/29/2010$399,990ListingRemovedAgent Provided
09/24/2010$399,990Listed For SaleAgent Provided
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Comparable Sales for 27 Chicago Ave

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1210 Saxon Avenue, Bay Shore, NY
0.05
Single-Family Home
$700,000
06/10/25
4
2.5
1,638
1222 Saxon Avenue, Bay Shore, NY
0.14
Single-Family Home
$760,000
09/05/25
5
2.5
2,380
70 Cleveland Street, Bay Shore, NY
0.06
Single-Family Home
$620,000
09/05/25
3
2
1,335
112 Cleveland Street, Bay Shore, NY
0.16
Single-Family Home
$655,000
01/30/26
4
2
1,800
60 Danbury Street, Bay Shore, NY
0.10
Single-Family Home
$560,000
07/29/25
3
2
939
1373 Saint Louis Avenue, Bay Shore, NY
0.32
Single-Family Home
$710,000
11/05/25
5
2
2,358
58 Elliot Street, Islip, NY
0.34
Single-Family Home
$775,000
07/15/25
5
2
2,232
75 Moody Avenue, Islip, NY
0.43
Single-Family Home
$750,000
07/21/25
4
2.5
1,912
70 Moody Avenue, Islip, NY
0.45
Single-Family Home
$710,000
07/03/25
4
3
3,007
100 Root Avenue, Islip, NY
0.57
Single-Family Home
$1,150,000
12/29/25
4
3
3,000

Nearby homes

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Assigned Schools

These are the assigned schools for 27 Chicago Ave.
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 Bay Shore

At least 379 Trulia users voted on each feature.

  • 87 % Say car is needed

  • 81 % Say it's dog friendly

  • 81 % Say yards are well-kept

  • 80 % Say parking is easy

  • 76 % Say there's holiday spirit

  • 63 % Say it's quiet

  • 63 % Say kids play outside

  • 61 % Say people would walk alone at night

  • 60 % Say there are sidewalks

  • 59 % Say it's walkable to restaurants

  • 58 % Say they plan to stay for at least 5 years

  • 55 % Say neighbors are friendly

  • 55 % Say streets are well-lit

  • 50 % Say it's walkable to grocery stores

  • 40 % Say there are community events

  • 37 % Say there's wildlife

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "Bay Shore is really the heart of the South Shore. With access to multiple beaches and a healthy mix of young and old, it’s one of the best places to raise your kids "
    0
    Flag
  • Scarlett Rosario Fernndez
    "It’s a save area, good people, good schools, stores, supermarkets hospitals church parks I love bay shore"
    0
    Flag
  • Daniel Rodriguez
    "I work in the area and grew up in the area I now live a little east of the town now, my commute to work is about a20 minute drive . Not to bad because I work nights "
    0
    Flag
  • Daniel Rodriguez
    "It’s a good place for kids with a good school system I went to as a child. Also many activities and state and local parks to visit "
    0
    Flag
  • Salvador Varela
    "Nice food restaurants all over and the mini malls … very welcoming and pet friendly I’m looking for a nice 1st floor apt "
    0
    Flag
  • Trulia User
    "I bought my house 3 years ago and absolutely love bay shore. The Main Street in town has so many new restaurants. There are lots of people walking around and it definitely feels safe in most parts."
    2
    Flag
  • Trulia User
    "Bay Shore is a big town with a small town feel. Everyone knows each other and helps each other out. It’s one of the most diverse towns on Long Island but in Bay Shore we are all family "
    0
    Flag
  • Jennifer.titmus
    "Vibrant downtown, close to parks and beaches, just across the bay from Fire Island. Amazing School District. Great options for child care and Summer Camp through the YMCA. "
    8
    Flag
  • Jennifer.titmus
    "My neighborhood has great access to public transportation and a great downtown. The Bay Shore Train Station is well kept and very clean. You can get a train to Babylon Train Station as well if you prefer the Babylon line but want to use Bay Shore Train Station’s easy parking. "
    1
    Flag
  • Curtzjackson
    "The public library and other facilities offer events in cooperation with Suffolk County administration. Many of the occasions are mainstream such as holidays and military events. Someone as me may feel detached socially if you don’t go with the crowd."
    1
    Flag
  • Jennygarcia1982
    "Bay shore very quiet. There also a lot of stores to do shopping including the Bay Shore mall. very little to no crime."
    1
    Flag
  • Dianetellez5
    "Yard sales BBQ Bay shore it’s very safe the neighborhood help every one that needs help the community is very friendly "
    1
    Flag
  • Camelle
    "Kids learn early about acceptance and it is a theme that transcends throughout the community. My children love the school and the YMCA is amazing!"
    1
    Flag
  • Camelle
    "Dogs are always on a leash and owners often stop to allow kids to pet or play with their pets when asked."
    1
    Flag
  • Betsymoran.3
    "Our neighborhood is super friendly. Sidewalks line the streets to create an extra safe walking environment. Having an elementary school nearby adds to our neighborhood charm "
    5
    Flag
  • Camelle
    "Never traffic and things flow smoothly even if a traffic light is out on the rare occasion. I ride my bike often with my two children and always feel safe doing so. "
    1
    Flag
  • Lisa B.
    "Drivers tend to ignore stop signs while traveling at excessive rates of speed which is very concerning for children riding bikes. "
    2
    Flag
  • Bmailhowel
    "Lirr to the city . It takes about an hour ride.driving in the neighborhood is not bad before 5pm. Easy access to the southern state parkway and the sunrise highway. The Long Island express way is not far and easy access."
    1
    Flag
  • L1vyh
    "Some dog owners don’t pick up after their dogs, some do. In the area I live in they mainly don’t until we tell them too."
    0
    Flag
  • Lydia O. F.
    "It’s quiet, safe and very beautiful. I do not regret moving to bay Shore. Neighbors mind there businesses and are very quiet. "
    7
    Flag
  • Curtzjackson
    "The Long Island Railroad system is often efficient, that might be the best for Suffolk County public transport. The buses along their routes handling their schedules vary in performance; from fairly good to average to awful. It can become costly to use the trains daily, for example, you may pay upward 32 dollars round trip Bay Shore to New York. Discounts and lowered fares exist according to circumstance, in addition for those disabled, elderly, and local college students. My general commute is 25 minutes or less, traveling by auto from Bay Shore to Ronkonkoma. Weather, auto accidents, road construction could have immediate impact causing delays, closures , and traffic jams. The county improved in fixing pot holes. They are remaining problematic in frequency of occurrences."
    0
    Flag
  • Dboyddan99
    "I lived her 20 years. Diverse, great schools, great restaurants in town, close to beaches and fire island."
    9
    Flag
  • Sandyanthony M.
    "School district is great to have kids go to school. There’s a lot of places to choose to shop. Plenty of bars and restaurants along main st."
    2
    Flag
  • Kathleen A. G.
    "The schools in Bay Shore are excellent. Downtown Bay Shore is thriving. Ocean beaches are a short drive away."
    1
    Flag
  • Michelle S.
    "We have a dog park and we have a bunch of restaurants .............................................."
    0
    Flag
  • Jennifer.titmus
    "My husband works in Manhattan and uses the LIRR out of Bay Shore to Penn and it is almost always on or close to schedule with very little disruptions or cancellations. "
    0
    Flag
  • Michael D.
    "Very good with public transportation An commuting I would say that the area is fantastic an excellent "
    0
    Flag
  • Dominican_papi800
    "Nice area, a lot to see and recreational areas around, close to the beach and to mayor the mayors roads "
    1
    Flag
  • David W.
    "Very dog friendly , there an elementary school with a large property, there's side walks, few cars, wide streets. "
    1
    Flag
  • Stephanie B.
    "It’s a great neighborhood. Good neighbors. Within walking distance to restaurants on Main Street. Great place to live."
    0
    Flag
  • Curtzjackson
    "Public transport is available but problematic, especially the county’s buses. Many benefit daily from the provision, the drivers are often professional and courteous. The schedules can be disrupted, buses run late weekly. Depending on the destination, the LIRR trains are costly and may be delayed according to circumstances. "
    0
    Flag
  • Sharon L.
    "There’s a lot of traffic and many blocks don’t have sidewalks so walking my dog gets a little hairy at times"
    1
    Flag
  • Kcervantes329
    "The schools in this district are amazing. Mary G Clarkson and Gardiner Manor have so many different programs for the kids to take advantage of. "
    0
    Flag
  • L c.
    "All dogs are leashed and picked up after. Very diverse community and mostly small to medium dogs. Only downside is there’s no dog park. "
    1
    Flag
  • Olganancy
    "we honor a lot of culturally diverse communities religions and backgrounds we have parades we have festivals it's really nice to see the community come together"
    1
    Flag
  • Mikerossiello
    "Dogs are always being walked through out my neighborhood. Leashed and owners pick up after them with bags"
    0
    Flag
  • Julie P.
    "They would like it very much. There is even a dog park for them to go to. Lots of open spaces to walk the dogs. Plenty of parks as well."
    1
    Flag

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27 Chicago Ave, Bay Shore, NY 11706 is a 5 bedroom, 4 bathroom single-family home built in 2001. This property is not currently available for sale. The current Trulia Estimate for 27 Chicago Ave is $749,200.