Winter, WI Homes for Sale (35 Real Estate Listings)

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5167n Doak Rd, Winter

$839,900 WINTER

↓ $60,000

5167n Doak Rd, Winter

4 Beds 2 Baths Single Family MLS® # 210019

(226/IK) - Located 4 mi. from Winter, WI on Doak Rd or 30 min. from Hayward on a 733 acre Class A Musky Lake, this Lake Winter home in the middle of a recreationalist’s slice of heaven await...

BIRCHLAND REALTY, INC. - PHILLIPS

Active
5167n Doak Road, Winter

$839,900 Lake Winter

↓ $60,000

5167n Doak Road, Winter

4 Beds 2 Baths 1 Acres 1,700 SqFt Single Family MLS® # 1587591

(226/IK) - Located 4 mi. from Winter, WI on Doak Rd or 30 min. from Hayward on a 733 acre Class A Musky Lake, this Lake Winter home in the middle of a recreationalist’s slice of heaven await...

Birchland Realty Inc./PhillipsRegional Multiple Listing Service of Minnesota Logo

Active
6009 W Dobbert Road, Winter

$799,900 Winter Lake

↓ $100,000

6009 W Dobbert Road, Winter

5 Beds 2 Baths 5 Acres 2,000 SqFt Single Family MLS® # 1590455

Not just a cabin on an island, LITERALLY OWN YOUR OWN ISLAND! FULLY furnished property totally turn key for AirB&B w instant revenue, or just enjoy yourself. Easy 2-minute boat ride from inc...

Copper Key Realty & WaterfrontRegional Multiple Listing Service of Minnesota Logo

Active
3094n Johnson Road, Winter

$735,000 Connors Lake

↓ $64,900

3094n Johnson Road, Winter

4 Beds 1 Acres 2,967 SqFt Single Family MLS® # 22501691

This beautifully crafted custom home is nestled on 100 feet of frontage offering a stunning setting on pristine Connors Lake, desired for its clear waters, deep fishing, & full recreational ...

NORTHWOODS REALTYRegional Multiple Listing Service of Minnesota Logo

Active
3094n Johnson Rd, Winter

$735,000 CONNORS

↓ $64,900

3094n Johnson Rd, Winter

4 Beds 4 Baths Single Family MLS® # 211645

This beautifully crafted custom home is nestled on 100 feet of frontage offering a stunning setting on pristine Connors Lake, desired for its clear waters, deep fishing, & full recreational ...

NORTHWOODS REALTY

Active
5044 Clayton Road, Winter

$679,000 Winter Lake

↓ $20,000

5044 Clayton Road, Winter

2 Beds 2 Baths 4 Acres 1,600 SqFt Single Family MLS® # 1590778

Welcome to your dream getaway! Nestled on over 4 wooded acres with direct lake frontage, this stunning log home offers the perfect blend of rustic charm and modern comfort. Many newer update...

NextHome WISCO SuccessRegional Multiple Listing Service of Minnesota Logo

Active
8800n Sams Lane, Winter

$650,000 Fishtrap

↓ $49,000

8800n Sams Lane, Winter

3 Beds 3 Baths 1 Acres 1,628 SqFt Single Family MLS® # 1590534

Nestled along the serene shores of Fishtrap Lake and bordering national forest, this immaculate estate offers a blend of luxury and rustic charm. The main residence, meticulously maintained,...

Northwest Wisconsin Realty TeamRegional Multiple Listing Service of Minnesota Logo

Active
New
5872w Otter Ln, Winter

$649,900 WINTER

5872w Otter Ln, Winter

4 Beds 2 Baths Single Family MLS® # 212577

This stunning 4-bedroom, 2-bath chalet-style home sits on the serene shores of beautiful Lake Winter, offering the perfect blend of comfort, privacy and natural beauty. Fully turn-key and so...

NORTHWOODS REALTY

Active
New
5872w Otter Lane, Winter

$649,900

5872w Otter Lane, Winter

4 Beds 2 Acres 2,000 SqFt Single Family MLS® # 22502596

This stunning 4-bedroom, 2-bath chalet-style home sits on the serene shores of beautiful Lake Winter, offering the perfect blend of comfort, privacy and natural beauty. Fully turn-key and so...

NORTHWOODS REALTYRegional Multiple Listing Service of Minnesota Logo

Pending
7267w Lanice Lane, Winter

$649,900 Lake Chippewa

7267w Lanice Lane, Winter

3 Beds 2 Baths 2 Acres 1,350 SqFt Single Family MLS® # 1590484

This private retreat sits on the remote southeastern edge of the Chippewa Flowage, just 6 miles from Winter and 31 miles from Hayward. Surrounded by wilderness and bordered by DNR and Chequa...

Northwest Wisconsin Realty TeamRegional Multiple Listing Service of Minnesota Logo

Active
6841 W Golf Course Road, Winter

$599,900 Lake Barker

6841 W Golf Course Road, Winter

4 Beds 6 Baths 1 Acres 4,020 SqFt Single Family MLS® # 1589720

Endless potential awaits with this property – whether you're looking to make it a permanent residence or a second home. Currently operating as a bar and restaurant on a scenic golf course, t...

Elite Realty Group, LLCRegional Multiple Listing Service of Minnesota Logo

Active
New
5044 Clayton Road, Winter

$530,000 Winter Lake

5044 Clayton Road, Winter

2 Beds 2 Baths 2 Acres 1,600 SqFt Single Family MLS® # 1592731

Welcome to your dream getaway! Nestled on over 2 wooded acres with direct lake frontage, this stunning log home offers the perfect blend of rustic charm and modern comfort. Many newer update...

NextHome WISCO SuccessRegional Multiple Listing Service of Minnesota Logo

Active
6306w Hunter Lake Road, Winter

$479,900 Hunter

↓ $20,100

6306w Hunter Lake Road, Winter

2 Beds 2 Baths 2 Acres 1,239 SqFt Single Family MLS® # 1588953

This charming, hand-scribed, furnished log cabin with 157’ of pristine frontage on Hunter Lake, offers the perfect Northwoods escape. The cozy retreat features an open-concept design highlig...

Edina Realty, Inc. - HaywardRegional Multiple Listing Service of Minnesota Logo

Active
5170 N Vermedal Road, Winter

$470,000 Winter Lake

↓ $25,000

5170 N Vermedal Road, Winter

2 Beds 1 Bath 2 Acres 960 SqFt Single Family MLS® # 1590722

Experience breathtaking sunrises from this year-round log-sided cabin on Lake Winter. This well-maintained home features a newer roof, windows, siding, as well as updated bathroom and living...

Area North Realty IncRegional Multiple Listing Service of Minnesota Logo

Active
5168 N Vermedal Road, Winter

$450,000 Winter Lake

5168 N Vermedal Road, Winter

2 Beds 2 Baths 1 Acres 1,322 SqFt Single Family MLS® # 1590733

Tucked off the main road, this 2-bedroom lake home offers a peaceful retreat on a .57-acre lot with 100 feet of frontage on Lake Winter, a Class A Musky lake known for great fishing, boating...

RE/MAX ResultsRegional Multiple Listing Service of Minnesota Logo

Active
5945 W Lee Road, Winter

$449,900 Barber Lake

↓ $49,100

5945 W Lee Road, Winter

1 Bed 2 Baths 2 Acres 1,156 SqFt Single Family MLS® # 1590468

Welcome to your serene retreat on Barber Lake! This 2022 fully remodeled 2BDR/2BTH cabin w/2-car attached garage boasts stellar lake views from almost every room, LP Smartside exterior, and ...

Woodland Developments & RealtyRegional Multiple Listing Service of Minnesota Logo

Pending
5968 Lake Winter Rd, Winter

$445,000

5968 Lake Winter Rd, Winter

3 Beds 2 Baths Single Family MLS® # 211727

Enjoy serene living on 3.38 acres across from Lake Winter and just down the road from the public boat landing. This meticulously maintained ranch-style home is surrounded by perennial garden...

RE/MAX NEW HORIZONS REALTY LLC

Active
4840 N County Road G, Winter

$399,000 Lake Chippewa

↓ $26,000

4840 N County Road G, Winter

3 Beds 2 Baths 1 Acres 1,248 SqFt Single Family MLS® # 1588561

Escape to this stunning 3-bed, 2 bath, 4 season log home nestled along over 150 feet of level frontage on the picturesque Chippewa River! Main floor features 2 cozy bedrooms, full bath, din...

Northwest Wisconsin Realty TeamRegional Multiple Listing Service of Minnesota Logo

Winter, WI Real Estate Statistics

Average Price $315K
Lowest Price $22.9K
Highest Price $1.2M
Total Listings 71
Avg. Days On Market 62
Avg. Price/SQFT $271

Property Types (active listings)


As of June 19, 2025 there are 35 active Winter, WI real estate listings for sale with an average listing price of $455,537. The highest-priced property listing is $839,900, while the lowest priced property can be purchased for $89,900. Winter, WI homes for sale have an average price of $284 per square foot, based on listings with an average of 2.9 bedrooms, 2.0 bathrooms, and 1,459 square feet of living space.

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