5259 N Winthrop Ave #2, Chicago, IL 60640
Property image
Property image
OFF MARKET

5259 N Winthrop Ave #2
Chicago, IL 60640

Edgewater
  • 2 Beds
  • 1 Bath

$322,600

Trulia Estimate
as of Jul 30, 2026
Est. Refi. Payment $2,268/mo*
Refinance Your Home

$322,600

Trulia Estimate
as of Jul 30, 2026
Est. Refi. Payment $2,268/mo*
Refinance Your Home
2 Beds
1 Bath

Local Information

  • Map ViewExplore the area around 5259 N Winthrop Ave #2.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Condo
Year Built
1917

About this House

This condo is located at 5259 N Winthrop Ave #2, Chicago, IL. 5259 N Winthrop Ave #2 is in the Edgewater neighborhood in Chicago, IL and in ZIP code 60640. This property has 2 bedrooms and 1 bathroom. This property has a lot size of 0.34 acres and was built in 1917.
5259 N Winthrop Ave #2, Chicago, IL 60640 is a 2 bedroom, 1 bathroom condo in Edgewater, built in 1917. It last sold for $203,000 on May 25, 2019. It is currently off market. The Trulia Estimate is $322,600, with a rent estimate of $2,378/month.

Home Details for 5259 N Winthrop Ave #2

Interior Features

Levels, Entrance, & Accessibility
Stories: 4Floors: Hardwood
Interior Details
Types of Rooms: Dining Room
Appliances & Utilities
DishwasherDisposalRefrigerator
Fireplace & Spa
Fireplace
Security
Security System

Property Information

Year Built
Year Built: 1917
Property Type / Style
Property Type: Condo

Exterior Features

Exterior Home Features
Exterior: BrickPorch
Parking & Garage
Parking Space: 1

Community

Units in Building: 25

Lot Information

Lot Area: 0.34 acres

Price History for 5259 N Winthrop Ave #2

DatePriceEventSource
05/25/2019$203,000Sold
N/A
05/25/2018$203,000Sold
MRED as distributed by MLS GRID #09914695
05/17/2002$175,500Sold
N/A

Market trends in Edgewater

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$280K
$9.25KMoM
Sale-to-List Price
100.0%
0.5%MoM
Price per sq ft
$260
$5MoM
Available listings
148
9MoM
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Property Tax and Assessment

Year2024
Tax$4,992
Assessment$248,470
Home facts updated by county records

Comparable Sales for 5259 N Winthrop Ave #2

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
5100 N Sheridan Rd #410, Chicago, IL
0.20
Condo
$180,000
03/26/26
2
1
1,250
902 W Winona St, Chicago, IL
0.28
Condo
$225,000
03/20/26
2
1
1,000
1059 W Foster Ave #1C, Chicago, IL
0.12
Condo
$200,000
04/28/26
1
1
-
5219 N Winthrop Ave #1, Chicago, IL
0.07
Condo
$460,000
10/29/25
2
2
1,400
1057 W Berwyn Ave #1, Chicago, IL
0.00
Condo
$330,000
07/15/26
2
1
1,312
1258 W Winona St #2C, Chicago, IL
0.29
Condo
$219,500
05/07/26
1
1
652
1309 W Foster Ave #2, Chicago, IL
0.30
Condo
$461,000
05/11/26
2
1
1,200
5245 N Winthrop Ave #3, Chicago, IL
0.01
Condo
$475,000
08/18/25
3
2
12,748
5317 N Kenmore Ave #2A, Chicago, IL
0.09
Condo
$300,000
01/21/26
2
1
-
5114 N Kenmore Ave, Chicago, IL
0.15
Condo
$446,000
06/01/26
3
1.5
1,500

Nearby homes

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Assigned Schools

These are the assigned schools for 5259 N Winthrop Ave #2.
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.

Neighborhood Overview

Edgewater
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Edgewater

At least 265 Trulia users voted on each feature.

  • 97 % Say it's dog friendly

  • 96 % Say there are sidewalks

  • 93 % Say it's walkable to restaurants

  • 91 % Say it's walkable to grocery stores

  • 84 % Say streets are well-lit

  • 73 % Say people would walk alone at night

  • 67 % Say there's holiday spirit

  • 64 % Say kids play outside

  • 58 % Say neighbors are friendly

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

  • 52 % Say it's quiet

  • 45 % Say there are community events

  • 44 % Say yards are well-kept

  • 40 % Say parking is easy

  • 39 % Say there's wildlife

  • 31 % Say car is needed

Sourced by Trulia users. Learn more about our methodology.
  • Jex
    "There are kids of all ages around the neighborhood. You may have trouble finding parking for school events, but public transportation is ample."
    0
    Flag
  • Roberto Ron
    "It’s small and quiet, people are vigilant. I lived here for 13 years and it’s getting better and nicer. "
    2
    Flag
  • Ds5g7yrgps
    "My neighborhood has a beautiful historic district less than a block from the lake. Multiple CTA options several bus routes a few express lines to Michigan Ave and downtown. The redline is conveniently located just east of Broadway, and the renovations are coming along quickly!! Many great restaurants located on Broadway, and grocery stores Jewel, Whole Foods and Aldi. The area is great for a stroll through the neighborhood or a bike ride along the lakeshore."
    3
    Flag
  • Flakin12000
    "The public transportation is great. Very accessible and easy to use. Every corner there’s a bus stop. "
    1
    Flag
  • Davis Kendrick
    "Be careful on the streets, people will breeze through here without looking but other than that it’s a very safe and fun area for kids"
    1
    Flag
  • Trulia User
    "because we are community and we share with share and take care all of us we are together and we watch for everyone"
    6
    Flag
  • Trulia User
    "very nice and quiet area. close to the lake which is for me very important. I'll recommend this area. "
    1
    Flag
  • Trulia User
    "My neighborhood is so nice ,nearby public transportation. there are a nice people beautiful community "
    1
    Flag
  • Trulia User
    "it's nice. block parties in summer. quiet for the most part. there is a school and churches close. there is a mixture of some college kids and families. there are more students closer to loyola."
    2
    Flag
  • Trulia User
    "I've lived here since the beginning of the pandemic and been able to watch it evolve, the community comes together and is very open to others"
    5
    Flag
  • Trulia User
    "It’s quiet and near amazing public transit. Close enough to the beach and perfectly placed between downtown chicago and Evanston "
    4
    Flag
  • Trulia User
    "Edgewater id such an amazing beautiful quiet place. There are a lot of friendly people. I’m new here only been here since October 2021 and it’s now December and I love it! It’s very safe and many dog walkers every time you step outside! Great place to raise a family. Schools are close and many grocery stores. I have not been to any community events but they do have virtual ones on book clubs because I received an invitation in the mail. I’m sure anyone who moves here will love it! The only downfall is the parking lol. This neighborhood is very special and I’m sure it will forever be a safe place. "
    1
    Flag
  • Trulia User
    "Great access to the city with any means of transportation. Good access to beautiful beaches and parks. "
    1
    Flag
  • Trulia User
    "Accessible to everything. Short walk to grocery stores. Commute to downtown only takes 15 minutes. Beauty of Lake Michigan is a plus "
    1
    Flag
  • Trulia User
    "The beach is always a hit! Cycling is easy here and is both good for commuting and good exercise. Good restaurants and shopping is all near."
    1
    Flag
  • Trulia User
    "Sheridan Road is horrific! Dangerous intersections because of careless drivers. Big open spaces for kids to play near the lake is available and ideal for children. "
    1
    Flag
  • Trulia User
    "A nice diverse neighborhood plenty of shopping centers friendly people close to the beach very friendly neighborhood"
    0
    Flag
  • Matt K.
    "Lots of dogs and open spaces for them. Many dog parks and dog friendly beaches in and around the neighborhood."
    0
    Flag
  • Joeymarra12345
    "This is a great community, I really feel like I know most of my neighbors. There is a real sense of community and it is very safe as Chicago PD and Loyola PD patrol the area "
    2
    Flag
  • Bornactor56
    "It's a very dog friendly neighborhood, but picking up after your pet is absolutely mandatory. We like to keep a very clean neighborhood around here."
    5
    Flag
  • Unspecified
    "The love the fact that our Community does Festivals, farmers market, Street sales walk sales, Close side roads for restaurants"
    1
    Flag
  • Joeymarra12345
    "There are several perks around the neighborhood and many have stations with complimentary waste bags "
    2
    Flag
  • Joseph Y.
    "It’s a great residential area and I see people from all walks of life represented here. The quick access to the lakefront path is a great retreat if you live in a small place. "
    3
    Flag
  • Mikhayla S.
    "It’s quiet and very safe. Everyone minds their own business but they aren’t afraid to say hello and get to know you."
    19
    Flag
  • Zelaznickitomasz
    "location, neighborhood, easy access to the public beach, nice restaurants, 20 minutes to the downtown and any places in Chicago "
    7
    Flag
  • Trulia User
    "the beach parties, fireworks during summer & beautiful scenery at Berger park by Sheridan & granville. "
    2
    Flag
  • Jennifer B.
    "Great neighborhood. Love it. Very friendly. Store are very close Jewel, Aldi , Target , Mariano. And a variety of other store. Nice variety of restaurants chipotle, mc Donald’s, Sonic. Papa Johns. "
    5
    Flag
  • Mel W.
    "farmers market, summerfest, Halloween, great restaurants, parks and schools . lovely family neighborhood....."
    2
    Flag
  • Jennifer B.
    "Great cultural neighborhood. Cultural friendly. A very LGBQT friendly neighborhood. Love that the beach is close by. "
    4
    Flag
  • Cute C.
    "dogs are always friendly and welcomed to this neighborhood, it make you secured and happy that you can walk out your dog with no judgement from other people cause everyone in this neighborhood is friendly and kind"
    2
    Flag
  • Dschust88
    "It’s a great area for dog owners. Dog park near by for the puppies to play around in and a beach as well. A dog groomer in the area that is trust worthy. Plenty of walking room for you and your puppy. Don’t know if many dislikes in the area but I’m sure there might be some but I can’t think of any and can only think of all the wonderful and great things about loving wth a dog in this neighborhood. "
    2
    Flag
  • G_requejo
    "Edgewater became the most amazing area in Chicago. We have the lake closer, gym, supermarkets and plenty of multicultural restaurants. I♥️Edgewater "
    1
    Flag
  • Sam.reid.barnes
    "Quiet, Affordable, On the lake and Red line.A real hidden gem in Chicago. Parking is easy. Quick to downtown but also quick to Evanston too."
    1
    Flag
  • Monica R. N.
    "There are a lot of dog owners around the neighborhood. Bad thing some of them they don’t pick up after their pets."
    1
    Flag
  • Jane
    "tons parks. close to beaches. good schools. We have 1 drug dealer and a few druggies who are for the most part harmless. they just beg a lot. strong police presence keeps things in check. other than that... awesome neighborhood with mostly fun loving LGBTQ community and people from everywhere: Africa, Thailand, Etc. incredible food is everywhere too. "
    0
    Flag
  • Monica R. N.
    "There are great parks and playgroups around the area. The beach is so close that’s always a plus in the summer!"
    1
    Flag
  • Wendyaschmidt
    "Perhaps that places aren’t big enough and not many have yards but the walking possibilities are great."
    0
    Flag
  • Gift
    "public transportation, biking, and walking mostly. cta is never a problem really. don’t need a car much"
    0
    Flag
  • Michael K.
    "Completely unfamiliar with any neighborhood events. Just a peaceful part of Chicago to live away from any action. "
    1
    Flag
  • Mukund R. A.
    "I love this area . Peaceful & nice lake view 15 min drive to downtown . One of the my favorite neighborhood in Chicago."
    1
    Flag

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Homes for sale near 5259 N Winthrop Ave #2

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Off Market Homes Near 5259 N Winthrop Ave #2

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