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  • The buying timeline

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3 beds
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New construction
With a pool
Homes Under $500K in Winter, WI
30 listings

Homes Under $500K in Winter, WI

Homes Under $500K in Winter, WI

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17 of 30 Listings
Map

Homes Under $500K in Winter, WI

17 of 30 Listings

  1. 7154 W McDermott Road — photo44Active

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #58131-90

Call Thomas

$319,500

2 bd · — ba · 864 sqft

7154 W McDermott Road, Winter, WI

Matthew Biller · Biller Realty

  • 7295W Hemlock Haven Rd — photo37Active

    $324,900

    2 bd · 2 ba · 1,176 sqft

    7295W Hemlock Haven Rd, Winter, WI

    KRAIG WHALEN · BIRCHLAND REALTY, INC. - PHILLIPS

  • 9146N Chippewa Pines Way — photo58Active

    $434,900

    3 bd · — ba · 1,745 sqft

    9146N Chippewa Pines Way, Winter, WI

    Mary Rufledt · Elite Realty Group, LLC

  • 9146 Chippewa Pines Way — photo70Active

    $434,900

    3 bd · 2 ba · 1,745 sqft

    9146 Chippewa Pines Way, Winter, WI

    Elite Realty Group, LLC

  • 9139 N Chippewa Pines Way — photo68Active

    $434,900

    3 bd · 2 ba · 1,745 sqft

    9139 N Chippewa Pines Way, Winter, WI

    MARY RUFLEDT · ELITE REALTY GROUP, LLC

  • 6960N Cth Gg — photo99Active

    $439,900

    3 bd · 2 ba · 1,663 sqft

    6960N Cth Gg, Winter, WI

    COTY FLESSERT · NORTHWOODS REALTY

  • W5907 Bauer Rd — photo29Active

    $274,900

    3 bd · 2 ba · 1,391 sqft

    W5907 Bauer Rd, Winter, WI

    IR KINSLEY GROUP · BIRCHLAND REALTY, INC. - PHILLIPS

  • W5907 Bauer Road — photo26Active

    $274,900

    3 bd · — ba · 1,391 sqft

    W5907 Bauer Road, Winter, WI

    Ida Kinsley · Birchland Realty Inc./Phillips

  • 9146N Chippewa Pines Way — photo58Active

    $469,900

    3 bd · — ba · 1,745 sqft

    9146N Chippewa Pines Way, Winter, WI

    Mary Rufledt · Elite Realty Group, LLC

  • 3598N Old J Road — photo25Active

    $249,900

    1 bd · — ba · 720 sqft

    3598N Old J Road, Winter, WI

    Ida Kinsley · Birchland Realty Inc./Phillips

  • 5650W Tower Rd — photo69Active

    $269,900

    3 bd · 2 ba · 1,456 sqft

    5650W Tower Rd, Winter, WI

    CALA NEU · NORTHWOODS REALTY

  • 9159N Chippewa Pines Way — photo49Active

    $369,900

    2 bd · — ba · 1,120 sqft

    9159N Chippewa Pines Way, Winter, WI

    Ida Kinsley · Birchland Realty Inc./Phillips

  • 4858 County Road G — photo36Active

    $426,000

    3 bd · — ba · 1,860 sqft

    4858 County Road G, Winter, WI

    Heidi Kringle · Northwest Wisconsin Realty Team

  • 5321N Lake Winter Road — photo59Active

    $449,500

    3 bd · — ba · 960 sqft

    5321N Lake Winter Road, Winter, WI

    Audrey Miller · Northwest Wisconsin Realty Team

  • 4091 W North Clover Road — photo36Active

    $424,900

    2 bd · — ba · 1,024 sqft

    4091 W North Clover Road, Winter, WI

    Debra Weinberger · Birchland Realty Inc./Park Falls

  • 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

  • 5527N Lake Winter Road — photo60Active

    $349,000

    2 bd · — ba · 748 sqft

    5527N Lake Winter Road, Winter, WI

    Bradi Kasparec · Northern Chase Real Estate

  • 12

    Explore Winter homes

    By price

    • Under $300K
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    • Under $700K
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    By bedrooms

    • 2 beds
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    By type

    • Single family
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    • New construction
    • With a pool
    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.

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    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #58131-90

    Call Thomas

    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: 2026-09-01 21:40:00 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.

    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