421 Deerpath Dr, Winthrop Harbor, IL 60096
OFF MARKET

$467,700

Trulia Estimate
  • 4 Beds
  • 3 Baths
  • 2,800 sqft (on 0.49 acres)

421 Deerpath Dr, Winthrop Harbor, IL 60096

Refinance Your Home
Currently Off Market - Sold Jun 7, 2001 for $340,000

Home Value

Trulia Estimate
$468K
Since last month
Decreased$2K (-0.5%)
Since last year
Increased$35K (+8.1%)
Since last sale
Increased$128K (+37.7%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +99% in the last 10 years
MonthEstimated value
2026
August 2026$468K
August 2026$467K
July 2026$471K
June 2026$476K
May 2026$469K
April 2026$457K
March 2026$446K
February 2026$435K
January 2026$430K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
521 Deerpath Dr, Winthrop Harbor, IL
0.11
Single-Family Home
$322,500
10/16/25
4
2.5
2,464
1636 Deerpath Cir, Winthrop Harbor, IL
0.16
Single-Family Home
$451,000
03/13/26
4
3.5
2,399
231 Oakdale Ave, Winthrop Harbor, IL
0.27
Single-Family Home
$316,000
07/01/26
3
2
1,014
1810 5th St, Winthrop Harbor, IL
0.29
Single-Family Home
$310,000
01/22/26
2
1.5
1,365
508 Cavin Ave, Winthrop Harbor, IL
0.84
Single-Family Home
$400,000
10/15/25
3
2.5
1,764
802 Kirkwood Ave, Winthrop Harbor, IL
0.61
Single-Family Home
$345,000
06/16/26
3
2.5
1,580
535 Thompson Ave, Winthrop Harbor, IL
0.68
Single-Family Home
$356,000
05/21/26
4
2
1,232
411 Thompson Ave, Winthrop Harbor, IL
0.68
Single-Family Home
$375,000
08/07/26
3
2
1,700
5001 9th St, Winthrop Harbor, IL
0.79
Single-Family Home
$415,000
09/15/25
5
3
2,400
214 Garnett Ave, Winthrop Harbor, IL
0.82
Single-Family Home
$360,000
04/01/26
4
3
1,380

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
401 Ravine Dr, Winthrop Harbor, IL 60096
0.08
$485,500
4
2.5
-
Off Market
311 Deerpath Dr, Winthrop Harbor, IL 60096
0.08
$541,300
4
3.5
6,050
Off Market
511 Deerpath Dr, Winthrop Harbor, IL 60096
0.10
$468,100
4
3
4,680
Off Market
521 Deerpath Dr, Winthrop Harbor, IL 60096
0.11
$421,000
4
2.5
2,464
Off Market
1600 Deerpath Cir, Winthrop Harbor, IL 60096
0.12
$372,600
2
2.5
1,588
Off Market
535 Ravine Dr #535, Winthrop Harbor, IL 60096
0.16
$372,400
3
3
2,922
Off Market
1636 Deerpath Cir, Winthrop Harbor, IL 60096
0.16
$451,000
4
3.5
2,399
Recently Sold
1503 3rd St, Winthrop Harbor, IL 60096
0.22
$294,700
3
2
2,136
Off Market
612 N Park Ave, Winthrop Harbor, IL 60096
0.26
$201,600
2
1
672
Off Market
630 Park Ave, Winthrop Harbor, IL 60096
0.26
$264,100
2
1.5
1,824
Off Market
528 Sheridan Rd, Winthrop Harbor, IL 60096
0.27
$241,800
3
2
1,556
Off Market
346 Sheridan Rd, Winthrop Harbor, IL 60096
0.27
$849,000
4
3
2,673
For Sale

Local Information

  • Map ViewExplore the area around 421 Deerpath Dr.
  • Schools1 Preschool School2 Elementary Schools1 Middle School2 High Schools
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1994
Lot Size
0.49 acres
Living Area
2,800 sqft
Price/Sqft
$167
Parking
Garage

About this House

THIS IS YOUR OPPORTUNITY TO LIVE IN THE SECLUDED PINES SUBDIVISION! BACKING TO A LARGE, EXPANSIVE WOODED RAVINE, THIS CUSTOM 2 STORY FEATURES QUALITY THRU-OUT. RECENTLY FINISHED WALKOUT BASEMENT ADDS OVER 1000 SF OF ADDITIONAL LUXURY LIVING. THIS IS A MUST SEE AND WON'T LAST LONG. NORTH POINT MARINA IS WITHIN MINUTES!
421 Deerpath Dr, Winthrop Harbor, IL 60096 is a 4 bedroom, 3 bathroom, 2,800 sqft single-family home built in 1994. It last sold for $340,000 on Jun 7, 2001. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $467,700, with a rent estimate of $3,654/month.

Home Details for 421 Deerpath Dr

Interior Features

Interior Details
Basement
Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: OtherDeck
Parking & Garage
GarageParking Space: 1Parking: Garage Attached

Property Information

Year Built
Year Built: 1994Year Updated: 1995
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 0.49 acres

Price and Tax history

DateEventPrice
Oct 14, 2009
Source: Agent Provided
ListingRemoved
$435,000
Jun 27, 2009
Source: Agent Provided
PriceChange
$435,000
Price decreased by 5%
Apr 4, 2009
Source: Agent Provided
Listed For Sale
$459,000
Jun 7, 2001
Source: N/A
Sold
$340,000
Jan 24, 1995
Source: N/A
Sold
$317,000

Market trends in Winthrop Harbor

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
20

Around this home

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

  • 51 % 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • Maria G.
    "You see dogs everywhere being walked by there owners. Very dog friendly area. This neighborhood is great!"
    0
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 421 Deerpath Dr

  • What is 421 Deerpath Dr estimated to be worth?
    Trulia's estimated value for 421 Deerpath Dr in Winthrop Harbor, IL is $467,700.
  • What is the price history for 421 Deerpath Dr?
    421 Deerpath Dr in Winthrop Harbor, IL last sold for $340,000 in June 2001.
  • Is Winthrop Harbor a buyer's or seller's market?
    Winthrop Harbor is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Winthrop Harbor?
    Residents describe Winthrop Harbor, IL as dog-friendly, easy to park in, and well-kept. Most residents say you need a car. See recently sold homes in Winthrop Harbor, IL.
  • Does 421 Deerpath Dr have air conditioning?
    Yes, 421 Deerpath Dr in Winthrop Harbor, IL has air conditioning.
  • How big is the lot at 421 Deerpath Dr?
    The lot at 421 Deerpath Dr in Winthrop Harbor, IL is about 0.49 acres (21,344 sq ft).

Apartments for Rent

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Off Market Homes Near 421 Deerpath Dr

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