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Homes Under $500K in Winter, WI

Start here

Homes for sale by state
Home buying tips
Before you start looking
The buying timeline

Afford it

Today's mortgage rates
Mortgage calculator
How much can I afford?
Get pre-approved

Make the deal

Writing a winning offer
Inspections & appraisals
Closing costs, itemized
Find a buyer's agent

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Review official public-safety information for any area from these government sources:

U.S. Dept. of Justice National Sex Offender Public Website (NSOPW)
FBI: state sex-offender registry directory

29 listings

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What's my home worth?
Compare selling options
Get an instant cash offer
Buy before you sell

Resources

How selling works
When should I sell?
Home selling tips
Pricing your home
What's worth fixing first
Find a seller's agent

New construction

Homes Under $500K in Winter, WI

Homes Under $500K in Winter, WI

17 of 29 Listings

Homes Under $500K in Winter, WI

17 of 29 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #58131-90

33Active
$324,900
2 bd · — ba · 1,176 sqft
7295W Hemlock Haven Road, Winter, WI
Kraig Whalen · Birchland Realty Inc./Phillips
58Active
$434,900
3 bd · — ba · 1,745 sqft
9146N Chippewa Pines Way, Winter, WI
Mary Rufledt · Elite Realty Group, LLC
70Active
$434,900
3 bd · 2 ba · 1,745 sqft
9146 Chippewa Pines Way, Winter, WI
Elite Realty Group, LLC

68Active
$434,900
3 bd · 2 ba · 1,745 sqft
9139 N Chippewa Pines Way, Winter, WI
MARY RUFLEDT · ELITE REALTY GROUP, LLC
99Active
$439,900
3 bd · 2 ba · 1,663 sqft
6960N Cth Gg, Winter, WI
COTY FLESSERT · NORTHWOODS REALTY
29Active
$274,900
3 bd · 2 ba · 1,391 sqft
W5907 Bauer Rd, Winter, WI
IR KINSLEY GROUP · BIRCHLAND REALTY, INC. - PHILLIPS
26Active
$274,900
3 bd · — ba · 1,391 sqft
W5907 Bauer Road, Winter, WI
Ida Kinsley · Birchland Realty Inc./Phillips
58Active
$469,900
3 bd · — ba · 1,745 sqft
9146N Chippewa Pines Way, Winter, WI
Mary Rufledt · Elite Realty Group, LLC
25Active
$249,900
1 bd · — ba · 720 sqft
3598N Old J Road, Winter, WI
Ida Kinsley · Birchland Realty Inc./Phillips
69Active
$269,900
3 bd · 2 ba · 1,456 sqft
5650W Tower Rd, Winter, WI
CALA NEU · NORTHWOODS REALTY
49Active
$369,900
2 bd · — ba · 1,120 sqft
9159N Chippewa Pines Way, Winter, WI
Ida Kinsley · Birchland Realty Inc./Phillips
36Active
$426,000
3 bd · — ba · 1,860 sqft
4858 County Road G, Winter, WI
Heidi Kringle · Northwest Wisconsin Realty Team
59Active
$449,500
3 bd · — ba · 960 sqft
5321N Lake Winter Road, Winter, WI
Audrey Miller · Northwest Wisconsin Realty Team
36Active
$424,900
2 bd · — ba · 1,024 sqft
4091 W North Clover Road, Winter, WI
Debra Weinberger · Birchland Realty Inc./Park Falls
39Active
$424,900
2 bd · 1 ba · 1,024 sqft
4091W Clover Rd N, Winter, WI
DEBRA WEINBERGER · BIRCHLAND REALTY, INC - PARK FALLS
58Active
$349,000
2 bd · — ba · 748 sqft
5527N Lake Winter Road, Winter, WI
Bradi Kasparec · Northern Chase Real Estate
Price Reduced23Active
$290,000
3 bd · 4 ba · 3,604 sqft
3480 Hwy 70, Winter, WI
ROXI PLATH · THE MOXI AGENCY LLC

1 2

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L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

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Listing data & MLS disclosures

NorthstarMLS: Based on information submitted to the MLS GRID as of 2026-08-23 10:22:16 UTC. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
Greater Northwoods MLS: IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Information is deemed reliable but not guaranteed.
Listing information ©2026 Greater Northwoods MLS, Inc®. All Rights Reserved. Last Updated: 2026-08-24 17:46:08 UTC
Wisconsin Real Estate Exchange (WIREX): IDX information is provided exclusively for consumers’ personal non-commercial use, may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and is deemed reliable but is not guaranteed by the MLS.

New construction
With a pool

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #58131-90

Winter, WI community profile

Population: 338
Median income: $48,043
Housing units: 292
People per sq. mi.: 0.8
Area: 424.4 sq. mi.

Source: HJN community data