335 Chestnut Cir, Winthrop Harbor, IL 60096
Property image
Property image
OFF MARKET

335 Chestnut Cir
Winthrop Harbor, IL 60096

  • 3 Beds
  • 3.5 Baths
  • 2,630 sqft (on 0.53 acres)

$478,600

Trulia Estimate
as of Jul 7, 2026
Est. Refi. Payment $2,501/mo*
Refinance Your Home

$478,600

Trulia Estimate
as of Jul 7, 2026
Est. Refi. Payment $2,501/mo*
Refinance Your Home
3 Beds
3.5 Baths
2,630 sqft
(on 0.53 acres)

Local Information

  • Map ViewExplore the area around 335 Chestnut Cir.
  • Schools1 Preschool School2 Elementary Schools1 Middle School2 High Schools
  • Shop & Eat
-- mins to
Commute Destination

Description

Minutes away from Lake Michigan you will find this stunning home sitting on a hillside surrounded by mature trees and nature life. As you walk inside, the main floor features a modern high-end white kitchen equipped with brand new black stainless steel appliances including a stove, fridge, dishwasher, microwave, quartz countertop, ceramic backsplash, island, and Bluetooth accessed speakers in the kitchen and living room. The Living room and master bathroom feature high ceilings with 7 Skylights together made by the highly rated "VELUX Skylights". Laminate wood floors, new stairs and railings, freshly painted walls and outlets with USB ports. The master bedroom has its own glass sliding doors to a deck and a double vanity connecting to a separate style bathroom where the bath will give you the extra space for a luxurious and comfortable bathing experience, without the taps and shower screen inhibiting your space. The second floor features a sizable loft, connecting 2 large bedrooms with ensuite baths, vaulted ceilings, & large closets. The basement features a recreation room, outdoor patio, extra washer and dryer machines, unfinished rooms that could easily be turned into a storage room, workout room & much more. The Utility room contains a sump pump (2019), water heater(2019), electrical wiring and plumbing were recently updated. Outside are 2 decks and a concrete patio ready to be used for gatherings with family and friends. Long and wide driveway right up to the huge 2.5 car garage that has strong concrete blocks, a new garage door and motion sensor lights. The whole house was renewed in 2021. If nature and water in a peaceful and quite circle call your name you found the right place!
335 Chestnut Cir, Winthrop Harbor, IL 60096 is a 3 bedroom, 4 bathroom, 2,630 sqft single-family home built in 1989. It last sold for $369,000 on Sep 29, 2022. It is currently off market. The Trulia Estimate is $478,600, with a rent estimate of $3,540/month.

Home Highlights

Parking
Garage
Outdoor
Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 335 Chestnut Cir

Interior Features

Interior Details
BasementNumber of Rooms: 10Types of Rooms: Dining Room
Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Floors: Tile, Carpet

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Other
Parking & Garage
GarageParking Spaces: 6Parking: Garage Attached

Property Information

Year Built
Year Built: 1989Year Updated: 1989
Property Type / Style
Property Type: Single Family HomeArchitecture: Contemporary

Community

Units in Building: 1

Lot Information

Lot Area: 0.53 acres

Price History for 335 Chestnut Cir

DatePriceEventSource
09/29/2022$369,000Sold
MRED as distributed by MLS GRID #11471769
09/10/2022$369,000ContingentMRED as distributed by MLS GRID #11471769
09/06/2022$369,000PendingToActiveMRED as distributed by MLS GRID #11471769
07/25/2022$369,000ContingentMRED as distributed by MLS GRID #11471769
07/22/2022$369,000Listed For SaleMRED as distributed by MLS GRID #11471769
09/10/2018$210,000Sold
MRED as distributed by MLS GRID #10048247
08/18/2018$209,500PendingAgent Provided
08/10/2018$209,500Listed For SaleAgent Provided
06/06/2018$158,359ListingRemovedAgent Provided
03/30/2018$0Listed For SaleAgent Provided
01/16/2018$170,000ListingRemovedAgent Provided
05/04/2017$170,000PendingAgent Provided
04/06/2017$170,000PriceChange
Agent Provided
08/23/2016$234,999Listed For SaleAgent Provided
07/06/2016$245,000ListingRemovedAgent Provided
06/09/2016$245,000PriceChange
Agent Provided
03/21/2016$249,500PriceChange
Agent Provided
02/23/2016$254,000Listed For SaleAgent Provided
09/18/2015$259,999ListingRemovedAgent Provided
03/11/2015$259,999Listed For SaleAgent Provided
09/24/2014$260,000ListingRemovedAgent Provided
09/03/2014$260,000PriceChange
Agent Provided
07/31/2014$265,000PriceChange
Agent Provided
07/22/2014$272,000Listed For SaleAgent Provided
06/17/2014$305,000ListingRemovedAgent Provided
07/18/2002$309,000Sold
N/A
05/10/1996$275,000Sold
N/A

Market trends in Winthrop Harbor

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
27
13MoM
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Property Tax and Assessment

Year2023
Tax$13,056
Assessment$365,466
Home facts updated by county records

Comparable Sales for 335 Chestnut Cir

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
521 Deerpath Dr, Winthrop Harbor, IL
0.27
Single-Family Home
$322,500
10/16/25
4
2.5
2,464
1636 Deerpath Cir, Winthrop Harbor, IL
0.25
Single-Family Home
$451,000
03/13/26
4
3.5
2,399
511 Deerpath Dr, Winthrop Harbor, IL
0.27
Single-Family Home
$437,500
07/22/25
4
3
4,680
1416 3rd St, Winthrop Harbor, IL
0.13
Single-Family Home
$295,000
07/10/25
3
2
1,136
1810 5th St, Winthrop Harbor, IL
0.22
Single-Family Home
$310,000
01/22/26
2
1.5
1,365
520 Holdridge Ave, Winthrop Harbor, IL
0.56
Single-Family Home
$455,000
08/15/25
3
3.5
3,876
508 Cavin Ave, Winthrop Harbor, IL
0.74
Single-Family Home
$400,000
10/15/25
3
2.5
1,764
818 Geddes Ct, Winthrop Harbor, IL
0.71
Single-Family Home
$359,900
07/25/25
4
2.5
2,896
530 Thompson Ave, Winthrop Harbor, IL
0.62
Single-Family Home
$375,000
07/30/25
3
3
1,323
802 Kirkwood Ave, Winthrop Harbor, IL
0.64
Single-Family Home
$345,000
06/16/26
3
2.5
1,580

Nearby homes

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Assigned Schools

These are the assigned schools for 335 Chestnut Cir.
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 Winthrop Harbor

At least 50 Trulia users voted on each feature.

  • 94 % Say it's dog friendly

  • 93 % Say parking is easy

  • 92 % Say yards are well-kept

  • 89 % Say car is needed

  • 76 % Say there's holiday spirit

  • 76 % Say there's wildlife

  • 69 % Say kids play outside

  • 64 % Say people would walk alone at night

  • 61 % Say it's walkable to restaurants

  • 61 % Say it's quiet

  • 52 % Say neighbors are friendly

  • 50 % Say they plan to stay for at least 5 years

  • 49 % Say there are sidewalks

  • 32 % Say it's walkable to grocery stores

  • 32 % Say there are community events

  • 17 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.
  • Bng7gwkkjj
    "Any events at North Point Marina during summer. Also having the pool right by Lake Michigan and a few other activities available at the Marina "
    0
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  • Nicole F.
    "I've lived here off and one since I was 19, I'm 34 now and still love it. Pleasant quiet neighborhood."
    0
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  • Jasmin M.
    "short 5 to 15 min commutes top most places. Stores, depots, restaurants, and industrial parks. As well as night life and amusement parks"
    0
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  • Maria G.
    "You see dogs everywhere being walked by there owners. Very dog friendly area. This neighborhood is great!"
    0
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  • Gracie W.
    "you see dogs walking a lot all around the park is paved and there is doggy poop bag stations located around the park "
    0
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  • Cheryldlandry
    "Super safe small town with great schools and sports organizations. They have a park, skate park and recreation center in the middle of town. Food that delivers and great police. "
    4
    Flag
  • Miller2225
    "Perfect location for family or empty nesters. Safe, quite and clean."
    1
    Flag
  • Turn1318
    "We have lived in this neighborhood for 17 years and it is a great place to live and raise a family. It is conveniently located to the Metra train station as well as North Point Marina, the largest marina on the Great Lakes). Perfect location for boaters and/or commuters."
    0
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  • mwieboldt5
    "Winthrop Harbor is conveniently located halfway between Chicago and Milwaukee. 45 minutes to either O'Hare or Mitchell airports. Metra station (Union North Line) within walking distance. Minutes to tollroad. Recreational opportunities abound! One mile to Northpoint Marina and Illinois Beach State Park biking trails. "
    1
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Apartments for Rent

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Homes for sale near 335 Chestnut Cir

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Off Market Homes Near 335 Chestnut Cir

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