Realty.com
Buy

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
Sell

Selling Options

  • 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
Home Loans
Find an Agent
Save searchAdvertiseSign In
Saved homesSaved searchesYour toursYour inquiriesRecently viewedAccount settings

Save search

Map layers

Safety

Safety & registry resources

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
Homes Under $500K in Winter, WI
Realty.com
Buy

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
Save searchAdvertiseSign In
Saved homesSaved searchesYour toursYour inquiriesRecently viewedAccount settings
  • Commercial

28 listings
Sell

Selling Options

  • 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
Home Loans
Find an Agent
Save search

Homes Under $500K in Winter, WI

Homes Under $500K in Winter, WI

Hide Map
20 of 28 Listings
Map

Homes Under $500K in Winter, WI

20 of 28 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #58131-90

Call Thomas
  1. 3778W Indian Way — photo42Active

    $84,900

    1 bd · 0 ba · 405 sqft

    3778W Indian Way, Winter, WI

    IR KINSLEY GROUP · BIRCHLAND REALTY, INC. - PHILLIPS

  2. 7953N Blaisdell Lake Rd — photo45Active

    $229,900

    4 bd · 1 ba · 1,500 sqft

    7953N Blaisdell Lake Rd, Winter, WI

    IR KINSLEY GROUP · BIRCHLAND REALTY, INC. - PHILLIPS

  3. 3674 W County Highway W — photo37Active

    $159,500

    3 bd · 1 ba · 836 sqft

    3674 W County Highway W, Winter, WI

    Biller Realty

  4. 5982 W Dobbert Road — photo29Active

    $440,000

    2 bd · 1 ba · 708 sqft

    5982 W Dobbert Road, Winter, WI

    Heidi Gill · NWWI, LLC

  5. 5982 W Dobbert Road — photo30Active

    $440,000

    2 bd · 1 ba · 708 sqft

    5982 W Dobbert Road, Winter, WI

    NWWI, LLC

  6. 6945N Pike Haven Road — photo30Active

    $300,000

    1 bd · 1 ba · 704 sqft

    6945N Pike Haven Road, Winter, WI

    Jennifer Schaidler · Area North Realty Inc

  7. 6563 W Railroad Avenue — photo26Active

    $77,500

    2 bd · 1 ba · 720 sqft

    6563 W Railroad Avenue, Winter, WI

    Matthew Biller · Biller Realty

  8. 5063 W Tower Road — photo60Active

    $349,000

    3 bd · 2 ba · 1,796 sqft

    5063 W Tower Road, Winter, WI

    Bradi Kasparec · Northern Chase Real Estate

  9. 5399 W Perch Lake Road — photo38Active

    $489,000

    4 bd · 2 ba · 1,980 sqft

    5399 W Perch Lake Road, Winter, WI

    Joseph Donnellan · Area North Realty Inc

  10. 7154 W McDermott Road — photo44Active

    $319,500

    2 bd · 1 ba · 864 sqft

    7154 W McDermott Road, Winter, WI

    Matthew Biller · Biller Realty

  11. 7295W Hemlock Haven Rd — photoPrice Reduced38Active

    $279,999

    2 bd · 2 ba · 1,176 sqft

    7295W Hemlock Haven Rd, Winter, WI

    KRAIG WHALEN · BIRCHLAND REALTY, INC. - PHILLIPS

  12. 6960N Cth Gg — photo99Active

    $439,900

    3 bd · 2 ba · 1,663 sqft

    6960N Cth Gg, Winter, WI

    COTY FLESSERT · NORTHWOODS REALTY

  13. W5907 Bauer Rd — photoPrice Reduced29Active

    $264,900

    3 bd · 2 ba · 1,391 sqft

    W5907 Bauer Rd, Winter, WI

    IR KINSLEY GROUP · BIRCHLAND REALTY, INC. - PHILLIPS

  14. 3555 Birch Lane — photo48Active

    $309,000

    3 bd · 2 ba · 1,440 sqft

    3555 Birch Lane, Winter, WI

    April Johnson · Route 63 Realty LLC

  15. 3598N Old J Rd — photoPrice Reduced28Active

    $249,900

    1 bd · 1 ba · 720 sqft

    3598N Old J Rd, Winter, WI

    IR KINSLEY GROUP · BIRCHLAND REALTY, INC. - PHILLIPS

  16. 5650W Tower Rd — photo69Active

    $269,900

    3 bd · 2 ba · 1,456 sqft

    5650W Tower Rd, Winter, WI

    CALA NEU · NORTHWOODS REALTY

  17. 9159N Chippewa Pines Way — photoPrice Reduced53Active

    $359,900

    2 bd · 1 ba · 1,120 sqft

    9159N Chippewa Pines Way, Winter, WI

    IR KINSLEY GROUP · BIRCHLAND REALTY, INC. - PHILLIPS

  18. 5321N Lake Winter Road — photo59Active

    $429,000

    3 bd · 1 ba · 960 sqft

    5321N Lake Winter Road, Winter, WI

    Audrey Miller · Northwest Wisconsin Realty Team

  19. 5170N Vermedal Road — photo42Active

    $399,000

    2 bd · 1 ba · 960 sqft

    5170N Vermedal Road, Winter, WI

    Bradi Kasparec · Northern Chase Real Estate

  20. 4091W Clover Rd N — photo39Active

    $424,900

    2 bd · 1 ba · 1,024 sqft

    4091W Clover Rd N, Winter, WI

    DEBRA WEINBERGER · BIRCHLAND REALTY, INC - PARK FALLS

12
Realty.com

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

Equal Housing OpportunityEqual Housing Lender

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.

© 2026 Realty.com. All rights reserved.·Privacy·Terms·California Privacy Rights·Accessibility·Licensing

Listing data & MLS disclosures

FargoMoorhead Area Association of REALTORS
The data relating to real estate for sale on this website comes in part from the Internet Data exchange (IDX) program of the FMAAR MLS. Real estate listings held by brokerage firms other than Realty.com are marked with the listing office name. IDX information is provided exclusively for consumers' 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 deemed reliable but not guaranteed. Copyright ©2026 Fargo-Moorhead Area Association of REALTORS®. No reproduction, compilation, retransmission or distribution of this data is permitted in any manner without the express, written permission of the Fargo-Moorhead Area Association of REALTORS®.
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: 2026-10-23 19:57:20 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.
  • Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #58131-90

    Call Thomas

    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