Winter Homes under $500,000

Your turnkey Northwoods lakefront getaway is ready and waiting on Lake Winter! Situated on 1.55 acres with 126 feet of waterfront, this charming 2-bedroom, 1-bath cabin offers a level lot, beautiful northern-exposure lake views, and an incredible opportunity to start enjoying lake life from day one. Built in 1993, the 708 sq. ft. cabin has been recently updated with new kitchen cabinets and appliances, new LVP flooring throughout, updated lighting fixtures, a new water heater, and a new stackable washer and dryer. Inside, you'll find an inviting open floor plan with vaulted ceilings, ceiling fans, and a cozy freestanding electric fireplace. Patio doors showcase the beautiful lake views and lead to an updated deck wrapping around two sides of the cabin, the perfect place to relax, entertain, or simply take in the peaceful Northwoods setting. An attached two-car garage provides plenty of additional space for vehicles, lake toys, and storage. Best of all, this property comes with an impressive list of inclusions! The dock and boat lift, 2010 Lund boat with 90 HP motor, 2025 Massimo Buck UTV, most furnishings in the cabin and garage, grill, deck furniture, and appliances are all included, making this a truly turnkey opportunity. Lake Winter is a 733-acre lake with a maximum depth of 22 feet and public boat landings for convenient access. Anglers can enjoy fishing for musky, walleye, largemouth and smallmouth bass, panfish, and more. Whether you're looking for a weekend escape, summer lake retreat, or your own place to enjoy everything the Winter area has to offer, this property makes it easy, just bring your bags and start enjoying life at the lake!

5982 W Dobbert Road, Winter

Listing courtesy of NWWI, LLC.

$440,000

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status

Your turnkey Northwoods lakefront getaway is ready and waiting on Lake Winter! Situated on 1.55 acres with 126 feet of waterfront, this charming 2-bedroom, 1-bath cabin offers a level lot, beautiful northern-exposure lake views, and an incredible opportunity to start enjoying lake life from day one. Built in 1993, the 708 sq. ft. cabin has been recently updated with new kitchen cabinets and appliances, new LVP flooring throughout, updated lighting fixtures, a new water heater, and a new stackable washer and dryer. Inside, you'll find an inviting open floor plan with vaulted ceilings, ceiling fans, and a cozy freestanding electric fireplace. Patio doors showcase the beautiful lake views and lead to an updated deck wrapping around two sides of the cabin, the perfect place to relax, entertain, or simply take in the peaceful Northwoods setting. An attached two-car garage provides plenty of additional space for vehicles, lake toys, and storage. Best of all, this property comes with an impressive list of inclusions! The dock and boat lift, 2010 Lund boat with 90 HP motor, 2025 Massimo Buck UTV, most furnishings in the cabin and garage, grill, deck furniture, and appliances are all included, making this a truly turnkey opportunity. Lake Winter is a 733-acre lake with a maximum depth of 22 feet and public boat landings for convenient access. Anglers can enjoy fishing for musky, walleye, largemouth and smallmouth bass, panfish, and more. Whether you're looking for a weekend escape, summer lake retreat, or your own place to enjoy everything the Winter area has to offer, this property makes it easy, just bring your bags and start enjoying life at the lake!

5982 W Dobbert Road, Winter

Listing courtesy of Northwest Wisconsin Realty Team.

$300,000

1 Beds ⋅ 1 Baths ⋅ ACTIVE Status

A Piece of Paradise on Barber Lake! Step into the timeless charm of this adorable three-season cabin, perfectly situated on the shores of Barber Lake with beautiful lakefront views. Lovingly cared for for decades, this cozy getaway offers the character and warmth that make a true Wisconsin cabin special. The generously sized kitchen features abundant cabinetry and plenty of countertop space, making meal preparation and entertaining a breeze. In the living room, a vaulted log ceiling creates a warm, rustic atmosphere that takes you back to the grand tradition of classic log-home living. The cabin comfortably sleeps six, making it an ideal retreat for family and friends. Step outside onto the expansive deck, perfect for relaxing, enjoying your morning coffee, grilling, or entertaining while taking in the peaceful lake views. With the water just steps away, you?ll feel like you can practically fish from the living room! Opportunities to find this kind of authentic cabin charm in a beautiful lakefront setting are hard to come by. Make this special Barber Lake retreat your own and start creating unforgettable Wisconsin getaway memories!

6945N Pike Haven Road, Winter

Listing courtesy of Area North Realty Inc.

$77,500

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status

Discover an excellent opportunity to own a cozy 2-bedroom, 1-bath single-family home right in the heart of Winter! Offering approximately 720 square feet, this property combines a convenient in-town location with easy access to some of the area's best Northwoods recreation. Located just off the Tuscobia Trail and within close proximity to multiple lakes, this property is perfectly positioned for ATVing, snowmobiling, boating, fishing, and enjoying everything the Northwoods has to offer. Whether you're looking for a year-round home, recreational getaway, or investment opportunity, this home provides a number of possibilities. Step inside and you'll find an interior that has been well maintained, offering a comfortable and inviting space that's ready to enjoy. The home comes fully furnished with everything included, making it an especially convenient option for someone looking for an affordable property without worrying about interior maintenance. The exterior could use some renovation, providing an opportunity for a new owner to add their own improvements, enhance curb appeal, and build equity over time. The roof was replaced in 2022, providing an important recent improvement. With its central Winter location, proximity to the Tuscobia Trail and area lakes, turnkey furnished interior, and potential to add value through exterior improvements, this property offers an affordable way to experience the Northwoods lifestyle. Year built is approximate. Buyer and buyer's agent to verify all information, measurements, condition, and other property details. Schedule your showing today before it's gone!

6563 W Railroad Avenue, Winter

Listing courtesy of Biller Realty.

$349,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status

If you have been looking for privacy, land, and storage- this could be it. The property has over 15 acres and adjoins approximately 14,000 acres of public land. There is a huge 40x48 pole building with floor-to-ceiling sliding doors on both sides and an attached lean-to for additional storage. The property also has a detached two-car garage located close to the house. The sellers have a newer garage door that they have not gotten around to installing, and it will be included in the sale. There is a large cleared area measuring approximately 250x800 feet that has previously been fenced for animals. Many of the posts are still there, but some work would be needed to fully enclose it again. The horseshoe driveway makes it easy to pull in, drive through, and head back out. The property features a drilled well, mound system, forced air furnace, as well as central AC. Inside, you will enter through the breezeway foyer, which connects to the kitchen and open-concept dining and living area. The main level has two bedrooms with a full bathroom between them. The lower level has a family room, a nonconforming bedroom, and a spacious 15x19 walkout primary suite with a huge closet. The lower-level bathroom already has a toilet and vanity, plus a large walk-in shower ready to be finished. The tile will be included with the sale. Several updates have already been completed, including a gorgeous newly decked and shingled roof, a new 200-amp breaker panel, new flooring in two bedrooms, attic insulation, a new water heater, a drywalled basement ceiling, and a new induction stove and hood. All other appliances have also been replaced within the past five years. The outdoor hot tub will stay too.

5063 W Tower Road, Winter

Listing courtesy of Northern Chase Real Estate.

$489,000

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status

TURN-KEY PERCH LAKE RETREAT WITH OVER 300 FEET OF FRONTAGE! This beautiful and well-maintained 4-bedroom, 1-bath lake home offers the perfect Northwoods getaway on crystal-clear Perch Lake. Set on 2.34 private acres with over 300 feet of lake frontage, this property provides an exceptional combination of privacy, beautiful water views, and easy access to all your favorite outdoor activities. Many updates have been completed throughout the property, allowing you to enjoy the lake lifestyle without the hassle of taking on a major project. The home offers plenty of space for family and guests, making it ideal as a year-round residence, vacation home, or investment property. Step outside and take in the beautiful views from the patio or deck while enjoying your morning coffee or relaxing after a day on the water. One of the standout features is the private boat landing, providing convenient access to beautiful Perch Lake right from your own property. Located in a fantastic recreational area, you'll be surrounded by opportunities for fishing, boating, ATV/UTV riding, snowmobiling, hunting, hiking, and countless other Northwoods adventures. Whether you're looking for a place to escape for weekends or a property where you can enjoy the Northwoods year-round, this turn-key Perch Lake property is ready for you to enjoy!

5399 W Perch Lake Road, Winter

Listing courtesy of Area North Realty Inc.

$319,500

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status

Your private Northwoods escape awaits! Tucked among towering trees on 38.77 beautifully secluded acres, this 2-bedroom, 1-bath property offers the perfect blend of peace, privacy, recreation, and convenience. Located on a quiet dead-end road just 5 minutes from the Town of Winter, this is a rare opportunity to own a private slice of the Northwoods where adventure begins right outside your front door. What you see is what you get - this property is being offered fully furnished and ready to enjoy. Built in 2000, this well-kept home offers comfortable Northwoods living surrounded by nature and opportunities with Knapp Stout Creek running through the West end. Major updates include a well, septic system, and electrical wiring installed in 2018. Dual heat sources - a wall furnace and wood stove - provide warmth and flexibility throughout the seasons, while two built-in air conditioners help keep the home comfortable during the warmer months. A driveway winds through the property, creating a true sense of seclusion while providing access to the expansive acreage. Established hunting blinds are included, presenting hunting opportunities just steps from your front door. Outdoor enthusiasts will appreciate the 220-amp RV hookup, offering added flexibility for recreational equipment, campers, or visiting guests. Approximately seven cords of firewood come with the property, making it easy to enjoy cozy evenings around your wood stove or outdoor fire pit. With its immaculate privacy, towering trees, established food plots, creek access, abundant wildlife, and convenient location, this property delivers the Northwoods lifestyle you've been waiting for. Quiet, secluded, and full of recreational possibilities, this is more than a home - it's your own private outdoor sanctuary. Skip the trip to the bank! Seller financing offered with 15% down - 10-year balloon amortized over 30 years at 7% interest. Reach out to schedule your private showing before it's gone!

7154 W Mcdermott Road, Winter

Listing courtesy of Biller Realty.

$279,999

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status

(122/KW)**Motivated Seller** Welcome to the ultimate cabin retreat, with direct access to ATV and snowmobile trails as well as the Chequamegon National Forest. This 2-bedroom, 2-bath home with a loft offers the perfect blend of rustic charm and modern comfort situated on a +/- .96-acre lot, giving you access to thousands of acres of outdoor adventure. Built just 4 years ago and immaculately maintained, the property is an ideal year-round getaway for outdoor enthusiasts. With approx. 1,176 finished square feet, the cabin comfortably accommodates family and guests. Inside, you?ll find vaulted ceilings, warm rustic finishes, and an open, airy floor plan centered around a cozy wood-burning fireplace?perfect for gathering after a day outdoors. The home includes two bedrooms, including a primary suite with a private en-suite bath. A bright, welcoming sunroom provides a peaceful place to relax, while a large storage closet offers convenient space for gear and seasonal items. In-floor radiant heat ensures year-round comfort. The property is being sold partially furnished, with most furniture available for negotiation, making it easy to move in and start enjoying cabin life right away. Outside, there is plenty of room to store recreational equipment, including an insulated, heated garage with an attached lean-to for boat storage, plus a separate storage shed. With nearly an acre of land and direct access to endless outdoor recreation, this turnkey cabin is ready for your next adventure?whether as a weekend getaway, hunting retreat, vacation rental, or year-round home. Price reduced to $279,999! (30-40N-05W Prt NWSW, lying south of road)

7295W Hemlock Haven Road, Winter

Listing courtesy of Birchland Realty Inc./Phillips.

$319,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status

Discover Waterfront Living on the Radisson Flowage! Tucked away at the end of a quiet dead-end road, this 3-bedroom, 2-bath home offers the perfect blend of privacy, recreation, and breathtaking waterfront views. With 100 feet of frontage on the Radisson Flowage. Step inside to a bright, inviting floor plan featuring spacious living areas, generously sized bedrooms?perfect for relaxing after a day on the water. The detached two-car garage provides plenty of room for vehicles, boats, and recreational gear. One of this property's most unique features is the permanently protected view across the water. The opposite shoreline is owned by the power company, ensuring your scenic backdrop remains beautifully undeveloped for years to come. Whether you're searching for a year-round residence, vacation getaway, or investment opportunity, this property delivers the Northwoods lifestyle you've been dreaming of. Conveniently located just minutes from Hayward and Lac du Flambeau, you'll have easy access to restaurants, shopping, golf, ATV and snowmobile trails, and the expansive trail systems that make Sawyer County a four-season destination. Don't miss your opportunity to own this peaceful waterfront retreat?where every day feels like a getaway!

3555 Birch Lane, Winter

Listing courtesy of Route 63 Realty LLC.

$249,900

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! Price improved to $249,900. 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.

$429,000

3 Beds ⋅ 1 Baths ⋅ ACTIVE Status

Set along the shores of 733-acre Lake Winter, this 3 bedroom, 1 bath year-round lake property offers privacy, peaceful Northwoods surroundings, and an exceptional waterfront setting. With over 500 feet of frontage, level elevation to the water, and wide lake and year-round sunset views, it is well-suited as a vacation home, recreational retreat, potential short-term rental, or comfortable full-time residence. The open kitchen, living, and dining area features beautiful water views, while the expansive yard provides plenty of room for a fire pit, outdoor dining, yard games, and gatherings after a day on the lake. The property totals nearly 4 acres per county records, with a portion of the acreage extending into the lake, creating a rare shoreline opportunity in the Winter area. The included dock provides a great place to fish, relax, and access the water. Lake Winter is recognized as a Class A musky fishing lake, making this a strong fit for anglers, boaters, and outdoor enthusiasts. The 2-car detached garage (24'W x 26'L) with concrete floor offers practical storage for vehicles, tools, fishing gear, ATVs, snowmobiles, and lake equipment. Updates completed within the last 5 years include Marvin windows and doors throughout the home and a high-efficiency furnace, along with a new septic system in 2025. A backup generator is also included. Located only 2 minutes from the Village of Winter, the property combines a quiet lakefront setting with convenient access to everyday necessities. Direct access from the driveway to the multiuse Tuscobia Trail connects you to miles of ATV and snowmobile riding, adding to the property?s appeal as a four-season Northern Wisconsin getaway.

5321N Lake Winter Road, Winter

Listing courtesy of Northwest Wisconsin Realty Team.

$299,900

ACTIVE Status

(323/KTG) Looking for an investment opportunity or want to live the Northwoods dream of owning your own business with time to play, located in the Village of Winter with a southern exposure of Doc Smith Park is this wonderful 3-4 apt building that may be right up your alley. One apartment is a 3 bedroom/2 bath unit being used as a short-term rental that sleeps up to 8. Apt #2 is a 1 bedroom 1.5 bath unit that was remodeled in the last few years. Apt #3 is a 2 bedroom, 1bath home with a woodburning fireplace. While Apt #4 is in the basement and has 3 bedrooms and 1 bath that needs a little TLC. There is ample outside parking along with a 3 bay garage, one heated for convenient access to make all those necessary repairs. There is also a 30x30 pole building for additional storage. The building is in a great location and backs right up to the Tuscobia Trail for all of your ATV/Snowmobile/recreational needs. The Chequamegon National Forest and other public hunting grounds nearby. Asking $299,900. Taxes 2025:$1731.00 (32-39N-05W Prt SWNE Lot 1 CSM 36/55 #8380)

6628W Marion Street Unit 1-4, Winter

Listing courtesy of Birchland Realty Inc./Phillips.

Winter Homes under $500,000

Newest Winter Homes under $500,000

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