809 Gregory Way, Winnebago, IL 61088
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Property image
OFF MARKET

809 Gregory Way
Winnebago, IL 61088

  • 4 Beds
  • 3.5 Baths
  • 3,250 sqft (on 0.38 acres)

$382,400

Trulia Estimate
as of Jul 30, 2026
Est. Refi. Payment $2,777/mo*
Refinance Your Home

$382,400

Trulia Estimate
as of Jul 30, 2026
Est. Refi. Payment $2,777/mo*
Refinance Your Home
4 Beds
3.5 Baths
3,250 sqft
(on 0.38 acres)

Local Information

  • Map ViewExplore the area around 809 Gregory Way.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1994
Lot Size
0.38 acres
Living Area
3,250 sqft
Price/Sqft
$118
Parking
Garage

About this House

One owner custom built home in desirable Winnebago sub. This 4 bedroom, 3.5 bath home offers more than 3,200 sq ft on 3 levels. Formal dining and living room w/french doors leading into the fam. room w/hardwoods and gas fireplace. Large eat-in kitchen w/42" cabinets, granite counters, SS appliances and sliders out to sunroom. Upstairs there are 4 bedrooms including the master w/private full bath w/new floor and walk in closet. Full walk out LL w/rec room, 2 bonus rooms and full bath. New roof, gutters, and some siding. Newer furnace, water heater, softener and custon front door!
809 Gregory Way, Winnebago, IL 61088 is a 4 bedroom, 4 bathroom, 3,250 sqft single-family home built in 1994. It last sold for $270,000 on Apr 23, 2021. It is currently off market. The Trulia Estimate is $382,400, with a rent estimate of $3,581/month.

Home Details for 809 Gregory Way

Interior Features

Interior Details
BasementAtticNumber of Rooms: 12Types of Rooms: Walk In Closet, Breakfast Nook, Dining Room, Family Room, Laundry Room, Master Bath, Pantry, Recreation Room, Sun RoomCeiling Fan
Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Carpet, Hardwood
Appliances & Utilities
Cable ReadyDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
FireplaceJetted Bath Tub
Windows, Doors, Floors & Walls
Double Paned Windows

Exterior Features

Exterior Home Features
Roof: CompositionDeckExterior: Shingle, Vinyl, Brick, CompositionLawnPatioPorch
Parking & Garage
GarageParking Spaces: 4Parking: Garage Attached, Off Street, On Street

Property Information

Year Built
Year Built: 1994
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 0.38 acres

Price History for 809 Gregory Way

DatePriceEventSource
04/23/2021$270,000Sold
NorthWest Illinois Alliance of REALTORS® #202100792
03/18/2021$269,900PendingKeller Williams #202100792
03/15/2021$269,900Listed For SaleKeller Williams #202100792

Market trends in Winnebago

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
11
3MoM
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Property Tax and Assessment

Year2024
Tax
Assessment$318,573
Home facts updated by county records

Comparable Sales for 809 Gregory Way

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
919 Gregory Way, Winnebago, IL
0.19
Single-Family Home
$265,000
01/23/26
4
3
2,652
606 Jarvis Dr, Winnebago, IL
0.16
Single-Family Home
$255,000
08/21/25
4
2.5
2,000
924 Jessica Trl, Winnebago, IL
0.23
Single-Family Home
$369,000
08/01/25
4
3.5
2,600
621 David Dr, Winnebago, IL
0.22
Single-Family Home
$250,000
07/31/25
4
3
1,400
714 Greenlee Ct, Winnebago, IL
0.32
Single-Family Home
$335,000
03/18/26
3
2.5
2,700
510 Zierke Ct, Winnebago, IL
0.19
Single-Family Home
$159,000
05/20/26
3
2.5
1,780
702 Jarvis Dr, Winnebago, IL
0.18
Single-Family Home
$174,000
04/20/26
4
3
1,824
608 S Church St, Winnebago, IL
0.43
Single-Family Home
$265,000
08/12/25
3
2
1,981
1470 Lamson Dr, Winnebago, IL
0.52
Single-Family Home
$273,000
11/26/25
3
1.5
2,209
603 S Church St, Winnebago, IL
0.47
Single-Family Home
$210,000
10/24/25
3
2
2,092

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Assigned Schools

These are the assigned schools for 809 Gregory Way.
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 Winnebago

At least 16 Trulia users voted on each feature.

  • 100 % Say parking is easy

  • 95 % Say kids play outside

  • 88 % Say it's dog friendly

  • 84 % Say people would walk alone at night

  • 81 % Say there's wildlife

  • 81 % Say there's holiday spirit

  • 79 % Say it's quiet

  • 78 % Say car is needed

  • 77 % Say there are sidewalks

  • 76 % Say yards are well-kept

  • 75 % Say neighbors are friendly

  • 58 % Say it's walkable to grocery stores

  • 56 % Say they plan to stay for at least 5 years

  • 38 % Say it's walkable to restaurants

  • 35 % Say streets are well-lit

  • 33 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Xr67gzm4gy
    "I have lived here for 32 years, neighbors are nice and I feel safe walking at all times of day/night by Myself!"
    0
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  • Richiesparling
    "Bedroom Community with many professionals who travel in to work in Rockford but want the peace of living outside the city. "
    0
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  • Ryanroeser1
    "school buses are the only buses. Some side streets dont have side walks. Plenty of miles of a bike/ jog path. "
    1
    Flag
  • Chick_025
    "Very friendly neighborhood. This house is a great location on a golf course, with a walk out patio. You can watch the sun rise every morning when you wake up. The neighbors are wonderful and the community is very involved in the upkeep and maintenance of the neighborhood. This location is only a 8 min walk from the community pool, lake and playground. The master suite is very large with 2 walk in closets a dream house! "
    0
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  • brainwashed711
    "You have to drive too far to go anywhere."
    0
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Apartments for Rent

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Homes for sale near 809 Gregory Way

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Off Market Homes Near 809 Gregory Way

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