Winter, WI Homes for Sale (23 Real Estate Listings)

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$1,800,000 LAKE OF THE PINES

N3874 Lake Of The Pines Rd, Winter

4 Beds 4 Baths Single Family MLS® # 213570

Exquisite one of a kind property on Lake of the Pines! Too much to actually list. Need room? Come take a look at this 4bd, 3ba home with a fully finished 3bd, 1ba living area above the detac...

THE MOXI AGENCY LLC

$799,800 Winter Lake

↓ $100

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 YOUR OWN ISLAND! FULLY furnished property totally turn key includes current AirB&B revenue, or just enjoy yourself. Easy 2-minute boat ride from incl...

Copper Key Realty & Waterfront

$749,900

↓ $100,000

7756w Old Highway 70, Winter

3 Beds 1 Bath 115 Acres 1,786 SqFt Single Family MLS® # 1595588

Over 114 acres of pure privacy and outdoor beauty! Tucked 1,500 feet back from the road, this 3 bedroom, 1 bathroom log home offers a serene setting with a pond view, fruit trees, and trails...

Biller Realty

$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 REALTY

$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

$699,000 WINTER

↓ $140,900

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

$699,000 Lake Winter

↓ $140,900

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./Phillips

$499,000

↓ $26,000

6960 N County Highway Gg, Winter

3 Beds 2 Baths 1 Acres 1,700 SqFt Single Family MLS® # 1593025

Unique opportunity to live and work in one location! This custom-built 3 bedroom, 1.5 bath home sits on a commercially zoned lot and features a sprawling 3,000 sq ft workshop—perfect for a b...

Keller Williams Realty Diversified

New

$474,900 Lake Barker

6733w Golf Course Rd, Winter

5 Beds 1 Bath Single Family MLS® # 214479

(228/KTG) Wait! Stop and Look now!! Are you searching for that perfect slice of the Northwoods to establish your legacy? A once in a lifetime opportunity for this “Family Compound” with 700+...

BIRCHLAND REALTY, INC. - PHILLIPS

$474,900 Barker Lake

6733w Golf Course Road, Winter

5 Beds 1 Bath 3 Acres 1,420 SqFt Single Family MLS® # 1596013

(228/KTG) Wait! Stop and Look now!! Are you searching for that perfect slice of the Northwoods to establish your legacy? A once in a lifetime opportunity for this “Family Compound” with 700+...

Birchland Realty Inc./Phillips

$445,000 Winter Lake

↓ $5,000

5168 N Vermedal Road, Winter

2 Beds 2 Baths 1 Acres 1,322 SqFt Single Family MLS® # 1593272

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...

Julie Brown Real Estate Group

$388,000

↓ $1,000

7803n N Cricket Lane, Winter

1 Bed 1 Bath 15 Acres 864 SqFt Single Family MLS® # 1592035

If you are looking for that perfect getaway either seasonal or year round, this is property is perfect for you. 15 acres that borders over 650 acres of public hunting and is 1 mile from sta...

Lesik Realty Group

$373,000 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 Team

$369,000

7043 W Fadness Road, Winter

3 Beds 2 Baths 10 Acres 1,300 SqFt Single Family MLS® # 1590654

Rare opportunity to own over 10 acres of beautiful Northwoods land! This property is a hobby farmer’s dream, featuring a barn and space to raise animals, along with some trails winding throu...

Biller Realty

$345,000 Lake Chippewa

↓ $14,000

4878n Fur Farm Trail, Winter

3 Beds 2 Baths 2 Acres 2,220 SqFt Single Family MLS® # 1592330

Your beautiful getaway awaits! This 3 bed, 2 bath home offers one level living with zero entry at the front of the home and only a couple of steps on the back deck to the large, open yard. 2...

CB Brenizer/Rice Lake

$300,000

3480 Hwy 70, Winter

3 Beds 4 Baths Single Family MLS® # 210827

The Loretta Steakhouse offers the perfect blend of comfort and opportunity, nestled in the scenic Northwoods between Park Falls and Winter, and just down the road from the scenic N Fork of t...

RE/MAX NEW HORIZONS REALTY LLC

$299,000

↓ $500

5158 South Main Street, Winter

2 Beds 4 Baths 0 Acres 5,216 SqFt Single Family MLS® # 1567939

This restaurant has been a staple in Winter for generations. The restaurant, kitchen, storage areas, restrooms, and apartment units have all been meticulously maintained and cared for by the...

Biller Realty

$242,000

6305 N Dam Road, Winter

3 Beds 2 Baths 2 Acres 1,385 SqFt Single Family MLS® # 1590635

Northwoods Living on Dam Rd, 1.8 miles from Big Chip Flowage boat launch, mins from the Wannigan Bar, this 3-bed, 2-bath home sits on 1.8 acres & offers year-round access to everything the N...

Keller Williams Realty Diversified

1 2

Winter, WI Real Estate Statistics

Average Price	$298K
Lowest Price	$14.9K
Highest Price	$1.8M
Total Listings	65
Avg. Days On Market	107
Avg. Price/SQFT	$240

Property Types (active listings)

As of October 15, 2025 there are 23 active Winter, WI real estate listings for sale with an average listing price of $487,974. The highest-priced property listing is $1,800,000, while the lowest priced property can be purchased for $129,000. Winter, WI homes for sale have an average price of $269 per square foot, based on listings with an average of 3.0 bedrooms, 2.0 bathrooms, and 1,298 square feet of living space.

Winter, WI Homes for Sale (23 Real Estate Listings)

$1,800,000 LAKE OF THE PINES

N3874 Lake Of The Pines Rd, Winter

$799,800 Winter Lake

6009 W Dobbert Road, Winter

$749,900

7756w Old Highway 70, Winter

$735,000 Connors Lake

3094n Johnson Road, Winter

$735,000 CONNORS

3094n Johnson Rd, Winter

$699,000 WINTER

5167n Doak Rd, Winter

$699,000 Lake Winter

5167n Doak Road, Winter

$499,000

6960 N County Highway Gg, Winter

$474,900 Lake Barker

6733w Golf Course Rd, Winter

$474,900 Barker Lake

6733w Golf Course Road, Winter

$445,000 Winter Lake

5168 N Vermedal Road, Winter

$388,000

7803n N Cricket Lane, Winter

$373,000 Lake Chippewa

4840 N County Road G, Winter

$369,000

7043 W Fadness Road, Winter

$345,000 Lake Chippewa

4878n Fur Farm Trail, Winter

$300,000

3480 Hwy 70, Winter

$299,000

5158 South Main Street, Winter

$242,000

6305 N Dam Road, Winter

Related Pages

Winter, WI Real Estate Statistics

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