Winter Real Estate

Nestled in the picturesque county of Sawyer in the state of Wisconsin, Winter is a charming city that offers a tranquil and idyllic setting for residents and visitors alike. Surrounded by nature's beauty, this city is a haven for outdoor enthusiasts seeking adventure and relaxation.

Winter is renowned for its stunning natural landscapes, with lush forests, sparkling lakes, and rolling hills dotting the area. The city's proximity to the Chequamegon-Nicolet National Forest provides ample opportunities for hiking, camping, and wildlife spotting. Outdoor enthusiasts can also enjoy fishing, boating, and kayaking in the nearby lakes and rivers.

In addition to its natural beauty, Winter boasts a rich history and vibrant community. The city is home to various cultural events and festivals throughout the year, showcasing the local arts, music, and cuisine. Residents can explore the charming downtown area, which features unique shops, restaurants, and cafes.

For those seeking a close-knit community with a slower pace of life, Winter offers an ideal escape. The city's friendly atmosphere and strong sense of community make it a welcoming place to call home. With its affordable real estate options, including cozy cabins and spacious homes, Winter provides a range of housing choices for individuals and families.

Whether you're looking to embrace the great outdoors or enjoy the warmth of a tight-knit community, Winter, Wisconsin, is a city that offers a little something for everyone.

Newest Listings in Winter

$274,900

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status

(125/KG) Check out this charming, beautiful home just 4.25 miles east of Winter. This 1391+\- sq ft home has 3 bedrooms and 2 bathrooms. Located on 1+/-acres. This single level home has an LP gas, field stone fireplace in the family room with plenty of pine walls to give that wonderful Northwoods feel along with a cozy living room just off the kitchen with dining area. It also features a master bedroom with ensuite. Highlights include 2 outdoor garages?one metal 24X48 pole shed and one 36X24 stick built garage that includes a workshop area, heated with a pellet stove. This property is just down the road from the Lake Winter (Class A Musky Lake) boat landing. Enjoy easy access to the ATV Trails including the famous Tuscobia Trail. This property is worth the look for that up north cabin with room to store your toys or maybe that retirement home with an easy to care for yard that is close to town. Just $274,900. 2025 Taxes: $1,256.86 (34-39N-05W Prt NESW Lot 1 CSM 35/169 #8280)

W5907 Bauer Road, Winter

Listing courtesy of Birchland Realty Inc./Phillips.

$339,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status

Enjoy peaceful waterfront living on this 3-bedroom, 2-bath home situated on approximately 0.46 acres with 100 feet of frontage on the beautiful Radisson Flowage. Located on a quiet dead-end road, this property offers exceptional privacy and breathtaking, permanently protected views across the water. The opposite shoreline is owned by the power company, ensuring the natural scenery will remain undeveloped for years to come. The home features spacious bedrooms, comfortable living areas, and endless potential to make it your own. Step outside to enjoy boating, fishing, kayaking, or simply relaxing from your private shoreline. The Radisson Flowage connects to the Chippewa Flowage system, giving anglers access to the outstanding fishing the area is known for, including musky, walleye, northern pike, bass, panfish, and more. The Deepest part of the lake is about 20' from dock. A detached two-car garage provides ample storage for vehicles, tools, and lake toys. Major updates include a new well system and water heater installed approximately five years ago. Whether you're searching for a year-round residence, vacation retreat, or investment opportunity, this waterfront property offers a rare combination of privacy, scenic views, and access to one of Wisconsin's premier fishing and recreational areas. Don't miss your chance to own this peaceful slice of Northwoods paradise! This property is thirty minutes to Hayward or Ladysmith. The Tuscobia State Trail system is less than a quarter mile ATV/UTV ride from the house.

3555 Birch Lane, Winter

Listing courtesy of Route 63 Realty LLC.

$649,500

6 Beds ⋅ 3 Baths ⋅ ACTIVE Status

Motivated Seller! Experience Northwoods living at its finest in this beautifully crafted 3,300-square-foot home situated on 4 private acres just blocks from Barker Lake and approximately 5 miles from the renowned Chippewa Flowage. Located only 25 minutes from Hayward, this property offers the perfect combination of modern comfort, outdoor recreation, and peaceful country living. This spacious home features 6 bedrooms and 2.5 bathrooms, with a thoughtfully designed handicap-accessible layout. Every component of the home and property is less than one year old, providing the peace of mind and efficiency of brand-new construction. The primary suite serves as a private retreat with a luxurious walk-in shower and Jacuzzi tub. Comfort is ensured year-round with in-floor heat throughout the main level, electric baseboard heat in every upstairs room, a new mini-split heat pump providing efficient heating and air conditioning, and fiber optic internet recently installed. Outdoor living is highlighted by a massive timber-frame covered porch complete with overhead lighting and a ceiling fan, creating the perfect space to relax and enjoy the surrounding hardwood forest. Additional property features include: ? 30' x 48' attached heated garage with in-floor heat ? 50-amp electrical service for a welder and 30-amp service for an air compressor ? 8' x 30' storage area ? Brand-new conventional (hybrid) septic system ? Newly drilled well ? Brand-new on-demand hot water heater ? Locally sourced lumber used throughout construction, harvested and milled within 20 minutes of the property Whether you're seeking a year-round residence, recreational retreat, or investment opportunity in Wisconsin's premier lake and forest country, this exceptional property offers unmatched quality, space, and location.

7107 W County Highway B, Winter

Listing courtesy of Biller Realty.

$299,900

1 Beds ⋅ 1 Baths ⋅ ACTIVE Status

(917/KG) Your new Recreational Headquarters await! 45+/- Acres with an Off-Grid cabin located south of Winter on Old J Rd makes for the complete package. Whether you are looking for a relaxing get away or for a hunting camp, STOP and look at this property. Bring the generator and take the winding driveway to the cabin which is complete with a composting toilet and shower so that you can have all the comforts of home but still have that rustic appeal. The cabin has an open concept design to fit a crowd to make more memories with friends including a main level bedroom and a sleeping loft. Carefree metal siding and roofing make this a maintenance dream. Sit on the covered porch to hear nature at its finest to help you relax from the stress of life. The property has an excellent wooded forest with some winding trails for you to develop more hunting experiences than a single person can handle, including a small part-time creek for all wildlife to enjoy. Not far to the Tuscobia Trail and many different routes and trails for summer and winter time enjoyment. Many Lakes and rivers in a short drive for all your fishing needs. This one is the real deal! Asking $299,900. 2025 Taxes:$1076.13 (20-38N-05W SENW & Maple Hill Lots 1 & 2)

3598N Old J Road, Winter

Listing courtesy of Birchland Realty Inc./Phillips.

$449,500

3 Beds ⋅ 1 Baths ⋅ ACTIVE Status

Set along the shores of 733-acre Lake Winter, this 3 bedroom, 1 bath cabin offers an exceptional lakefront setting with over 500 feet of frontage, level elevation to the water, and wide lake and year round sunset views. The open kitchen, living and dining area features amazing water views. The property totals nearly 4 acres per county records, with a portion of that acreage extending into the lake, creating a rare shoreline opportunity in the Winter area. Designed for easy lake enjoyment, the property features an expansive yard with plenty of room for a fire pit, outdoor dining, yard games, and gatherings after a day on the water. The included dock provides a great place to fish, relax, and access the lake. Lake Winter is recognized as a Class A musky fishing lake, and the water access can accommodate any size boat, making this a strong fit for anglers, boaters, and outdoor enthusiasts. The 2-car detached garage (24'W x 26L) with concrete floor offers practical storage for vehicles, tools, fishing gear, ATVs, snowmobiles, and lake equipment. Recent updates (in the last 5 years) include Marvin windows and doors in the entire cabin, high efficiency furnace, and new septic (in 2025). There is a back up generator that is included as well. Located just 5 minutes from Winter, WI, and with direct ATV and snowmobile trail access, this property offers convenient access to year-round Northwoods recreation. With short-term rental potential, this cabin is well-suited as a personal lake retreat, recreational basecamp, or flexible investment property.

5321N Lake Winter Road, Winter

Listing courtesy of Northwest Wisconsin Realty Team.

$249,900

1 Beds ⋅ ACTIVE Status

Welcome to a little slice of heaven on earth! This one of a kind property offers 10.5 wooded acres with 270 feet of frontage on Winter Lake. You can bow hunt and fish just steps from your door! There is a well cared for 2 car garage with a studio apartment. This great piece of ground is ready for you to build that dream cabin or house on. Winter Lake is about 730 acres with an average depth of 22'. This lake is known for Musky, Walley and Bass fishing. Come explore the great outdoors!

5807 Strom Road, Winter

Listing courtesy of C21 Affiliated.

$417,000

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status

Nestled on approximately 2 acres with an impressive 242 feet of owned frontage, this Lake Winter property offers a larger lot on the lake with nearly double the frontage of many surrounding properties. The level to gently sloping lot leads right to the water's edge with a sandy bottom, low elevation, and dock already in place. The home offers 2 bedrooms, 1 bathroom, approximately 960 sq ft, one floor, an open concept layout, electric baseboard heat, wood burning stove, laundry area wall AC unit, and easy, low maintenance living. Enjoy morning coffee and beautiful sunrises from the deck overlooking the large front yard and lake views as the property faces east. Recent updates include windows, doors, fascia, roof, deck, log siding, plus additional updates to the living room and bathroom completed by the current owner. Storage is a huge bonus here with two detached garages including a 24x24 insulated garage and an additional 26x36 garage with plenty of room for boats, snowmobiles, ATVs, tools, and lake toys. Located on a private road, this property sits on Lake Winter, known as one of the area's premier fishing lakes and well known as a Class A musky lake. As one of the larger lakes in the area, it offers excellent recreation while still being part of the welcoming small community of Winter. Whether you're looking for a year round home, cabin, or up north getaway, opportunities with this much frontage, acreage, and garage space do not come around often. Priced to sell.

5170N Vermedal Road, Winter

Listing courtesy of Northern Chase Real Estate.

$599,000

ACTIVE Status

Experience exceptional privacy and true Northwoods living on this 110-acre estate in northeast Sawyer County. Designed for those who value seclusion, natural beauty, and outdoor recreation, this property combines a custom chalet-style home with rolling terrain, flowing water, and thoughtfully managed habitat. The land is primarily wooded with a mix of hardwood ridges, conifer wetlands, and transitional habitat supporting abundant wildlife. Deer Creek winds through the center of the property, enhancing both scenery and ecological diversity. Located less than one mile from a public boat landing on a 340-acre Class A muskie lake, with nearby ATV and snowmobile trail access. Custom half-log sided chalet built in 2005 with Amish craftsmanship, offering approx. 1,500 sq ft with 2 bedrooms plus loft, main level living with laundry, gas fireplace, radiant in-floor heat, R60 insulation, Starlink internet, and recent exterior stain and deck updates. Pre-listing inspection completed. Professionally managed land includes established trail system, open areas suitable for food plots, hardwood ridges, conifer wetlands, and an active forest management plan. Ideal for enjoying frequent wildlife sightings including deer, turkey, grouse, bear, and waterfowl. Approximately 30 minutes to Park Falls, 45 minutes to Hayward and Ladysmith, and about 1 hour to Copper Falls State Park and St. Peter?s Dome. Low taxes and turnkey condition make this a rare opportunity to own a private Northwoods retreat. Additional acreage across the road for sale (shown in photos)

8225 N Blaisdell Lake, Winter

Listing courtesy of Century 21 Affiliated.

$699,900

5 Beds ⋅ 2 Baths ⋅ ACTIVE Status

Did you ever dream of owning your own island? Well this beautiful home on Lake Winter, LITERALLY COMES WITH YOUR OWN ISLAND! A Fully furnished property, totally turn-key. Current AirB&B (revenue forwarded to you at closing), or just enjoy it for yourself if you prefer. Easy 2-minute boat ride from your access lot on shore. Access lot is included with this purchase (parks 6 cars). Property & chalet have been entirely updated (pex plumbing & water-saving fixtures, central air, furnace, trails cut, & much more). This property is very well maintained & needs nothing to start enjoying. Optional seasonal revenue approx $50,000 (June-Sept) w much higher potential. Desirable Lake Winter, Class A Musky fishing, ski/tube/jetski. Rustic Lodge (food and bar) accessible by boat. Near Tuscobia Trail, golf course & restaurants. Includes: 2023 Sylvan Mirage Pontoon, pavilion, fish cleaning station, dog wash station, swimming area, trails around the island, kayaks, canoe, paddleboat, docks, lawn equip, outdoor furniture, picnic tables etc. Fast wifi streams multiple devices. Everything runs on electric for maximum convenience (central air & furnace are a newer electric heat pump), the power company installed a line underwater and is responsible for maintaining. Year-round access via 2026 Wilcraft amphibious vehicle (drives like a side-by-side, but is enclosed and goes on water or ice-not included). Seller will consider accepting your property in trade toward purchase. Life is short, this is a once in a lifetime opportunity to start a family legacy for generations!

6009 W Dobbert Road, Winter

Listing courtesy of Copper Key Realty & Waterfront.

$450,000

ACTIVE Status

(73/KG) Looking for the perfect Opportunity! Looking for the perfect reason to escape to the Northwoods and be your own BOSS! Well, here is an opportunity that is worth investigating. Located on Highway 70 in the Village of Winter, just off the famous Tuscobia trail for snowmobile, ATV/UTV traffic. Near enough to the famous Chippewa Flowage and Lake Winter and numerous other lakes to attract fisher people off the lakes to enjoy breakfast/lunch/dinner and maybe a cocktail or two? Well known locally for their famous Friday night fish fry. This Bar/Grill/2-unit Motel offers the best of all worlds. Spacious room in the bar and dining room to accommodate a crowd. Or enjoy the outdoors under the pavilion for entertainment on the large outdoor stage for live bands and cocktails at the tiki bar for the volleyball leagues and the horseshoe tournaments. This opportunity is waiting for you to come and make it yours? It comes turnkey so the only thing that is missing is YOU! 2025 Taxes: $3443.31 (32-39N-05W Prt NENE Lot 1 CSM 15/63 #3763)

6542W State Highway 70, Winter

Listing courtesy of Birchland Realty Inc./Phillips.

$159,000

ACTIVE Status

A beautiful 1.72 acre level lot, 161 feet of frontage, and western exposure on Winter Lake. Per the DNR, this lake is 733 acres, has a maximum depth of 22 feet. Fish include Musky, Panfish, Largemouth Bass, Smallmouth Bass and Walleye.

Lot 11 Lake Winter Road, Winter

Listing courtesy of C21 Woods to Water.

$649,900

5 Beds ⋅ 3 Baths ⋅ ACTIVE Status

New Construction in the Heart of the Northwoods | Winter, WI | 5 Bed | 3 Bath | 2.26 Acres | $649,900 Some homes check boxes. This one earns its place. Built in 2025 and finished with the kind of craftsmanship you don't expect at this price point, this 5-bedroom, 3-bath home sits on 2.26 private acres just minutes from the Lake Winter boat landing ? and it's ready for whatever you're looking for: full-time residence, Northwoods retreat, or smart investment in Sawyer County. At 2,996 finished square feet, the layout is open and purposeful. Vaulted ceilings draw the eye up. Custom cabinetry, detailed trim work, and durable vinyl plank flooring ground the space. The kitchen and living area flow together naturally ? equally comfortable on a quiet Tuesday morning or a Saturday night with a full house. The details matter here. Tile-surround showers. Copper bathroom sinks. A private upper-level loft suite with its own bedroom and full bath ? ideal for guests, a home office, or a space that adapts as your needs do. The finished lower level adds flexible living space, and in-floor heat runs through both the lower level and the attached garage, so comfort doesn't stop at the front door. The garage itself reflects the same thoughtfulness: floor drain, insulated walls, blown fiberglass ceiling insulation, and a finished drywall interior. Spray foam insulation throughout the exterior walls and ceilings keeps energy costs in check year-round, alongside central AC, a durable metal roof, and low-maintenance vinyl siding. Step outside and the property opens up. A covered front porch for morning coffee. A back deck for evenings after a day out on the lakes. And beyond the lot lines ? public boat landings, trails, fishing, and everything that makes this corner of Wisconsin worth coming back to. This is what new construction in the Northwoods should look like ? priced at $649,900.

4795N Lake Winter Road, Winter

Listing courtesy of Century 21 Affiliated.

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