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2714 Chamberlain Ave, Madison
$299,900
2 Beds ⋅ 1 Baths ⋅ 2035887 MLS ⋅ ACTIVE Status
Attention seasoned investors, flippers, and contractors! This cozy property offers an incredible opportunity in the high-demand University area. Close to bus stops for a quick commute to campus or downtown, this home is located in one of the city's most walkable and vibrant neighborhoods! Priced to reflect its need for significant updates, the home is ready for a complete transformation. Bring your vision to unlock its full potential. The property is being sold strictly AS-IS with No warranties or representation of condition. Seller will not negotiate repairs or credits. Any remaining personal property will convey. Roof 2010 per city records, HVAC 2018, Water Heater 2020, Water Softener 2021. Due to condition, conventional financing is unlikely; Seller is seeking CASH OFFERS Only. Proof of funds required with all offers. No Offers will be reviewed prior to 11/10/2026. Please Allow a 48 hours response time for binding acceptance by POA.

2714 Chamberlain Ave, Madison

7788 County Road I, Vienna
$1,297,000
5 Beds ⋅ 4 Baths ⋅ 2035752 MLS ⋅ ACTIVE Status
Stunning Prairie-style home with wrap around porch and metal roof set on a nearly 7 acre wooded, fenced lot! Out in the country with multiple outbuildings and STILL within the Deforest School District & Dane County. Exterior features include a newer paved driveway leading to a 5+ car garage with heated golf simulator room, insulted workshop. Outbuilding include a rejuvenated 1860's barn, a NEW 6 stall horse stable with indoor riding arena/storage area plus numerous sheds and a chicken coop! Perfect for hobby farmers! Inside the home you'll find a large, updated living area with cathedral ceilings, open dining and kitchen space with fabulous views of the gorgerous property. Main floor master suite offers a private en suite bathroom and walk-in closet. 3 additional bedrooms upstairs with a full bathroom. Lower level is HUGE with a newly finished full bathroom, rec space, and a work out room. This is a rare find and a must see!

7788 County Road I, Vienna

10873 Smokey Mountain Trl, Blue Mounds
$479,900
3 Beds ⋅ 4 Baths ⋅ 2035728 MLS ⋅ ACTIVE UNDER CONTRACT Status
Showings start 11/2! Charming Cape Cod in beautiful Blue Mounds! You will love the views and this amazing lot backing to the Military Ridge Bike Trail. Added bonus is the neighborhood park also just steps away. The outside has so much to offer including 2 tiered deck overlooking your water garden with fish,a garden shed and green house, plenty of area for gardening or playing in the yard and a large front porch to relax on as well. Inside you will find 3 bedrooms, 3.5 baths, large laundry/mud room off garage, lots of natural light, walkout LL to patio. Added bonus is a separate workshop area for wood working or whatever hobby interests you! Roof and windows were recently redone! Blue Mounds State Park, Brigham Park and Cave of the Mounds are all minutes away! This property has so much to offer!

10873 Smokey Mountain Trl, Blue Mounds

850 Tipperary Rd, Oregon
$515,000
3 Beds ⋅ 3 Baths ⋅ 2035615 MLS ⋅ ACTIVE UNDER CONTRACT Status
Room to roam, views to savor, and possibilities galore! Nestled on 2.76 picturesque acres in the Town of Oregon and surrounded by Hann's Christmas Farm, this unique property offers a peaceful country setting with stunning views in every direction. The home features 3–4 bedrooms, a dedicated office, 2.5 baths, and a walkout lower level. A covered partial wraparound deck provides the perfect spot to relax, entertain, and take in the beautiful surroundings. Two substantial outbuildings add incredible versatility, including a 62' x 40' pole barn and a second building featuring two separate rooms measuring 33' x 11' and 34' x 9'. Whether you're dreaming of a workshop, hobby space, storage for recreational toys, or room to pursue your passions, the possibilities are plentiful. A new roof installed in November 2024 adds peace of mind. A rare opportunity to enjoy country living with space, privacy, and flexibility!

850 Tipperary Rd, Oregon

2880 Siggelkow Rd, Cottage Grove
$1,200,000
4 Beds ⋅ 4 Baths ⋅ 2035450 MLS ⋅ ACTIVE Status
1st show OH 10/29 @ 5pm. Designed around breathtaking backyard sunsets, this custom ranch offers privacy & thoughtful design on 2.5 acres, minutes from the Beltline & interstate. A backyard oasis features a heated saltwater pool w/auto cover, firepit, hot tub hookup, in-ground trampoline & established landscaping that makes this home better than new. Enjoy the views from the 3-season porch w/vinyl windows & gas fireplace. Inside, a brilliant split-bedroom layout offers 4 spacious main-floor bedrooms, including a luxurious primary suite w/dedicated laundry & pocket office. The secondary wing offers 2 full baths & a second laundry area. Custom conveniences include an oversized walk-in pantry w/appliance garage & garage access, dog-washing station & premium lighting. A 532 SF finished bonus room adds recreation space, while the 2,000+ SF unfinished basement features 9' ceilings, future bath plumbing, full windows & garage access. The best of both worlds: rural serenity, city convenience!

2880 Siggelkow Rd, Cottage Grove

1910 Swainson Dr, Madison
$709,900
4 Beds ⋅ 3 Baths ⋅ 2035505 MLS ⋅ ACTIVE Status
Experience luxury, comfort, and convenience in this exceptional home! Stunning 4-bedroom exposed ranch in desirable Hawks Valley with a legal 5th bedroom! Built in 2017, this move-in-ready home offers nearly 3,000 finished sq ft of stylish living space. Enjoy vaulted ceilings, an open-concept design, expansive windows, and a striking floor-to-ceiling stone fireplace. The chef’s kitchen features an oversized island, ample cabinetry, and a walk-in pantry. Relax in the private owner’s suite with a spa-inspired bath and spacious walk-in closet. The finished exposed lower level offers a generous rec room and flexible space for guests, a home office, gym, or 5th bedroom. Ready for entertaining and everyday living! Conveniently located near scenic trails, parks, golf courses, Epic, downtown Verona, and Madison’s west side amenities.

1910 Swainson Dr, Madison

4335 Missouri Rd, Deerfield
$440,000
1 Beds ⋅ 1 Baths ⋅ 2035482 MLS ⋅ ACTIVE Status
Country-Style One-Bedroom Farmette on 3.362-Acres!! The home is charming with spacious rooms, a large eat-in kitchen, and wonderful views. There is an inspired L-shaped deck on the east and south sides that lets you enjoy your own private property. (There is a second floor to the home which is over 700 square feet and was used for bedrooms. Presently it is used for attic storage but has insulation and a radiant heat system and could be re-built for additional living area.) The site is a nicely rolling piece of rural land well set-up for projects, horses, or carrots. There is a modern metal shed that is 30 feet by 45 feet and a classic barn with box stalls, a good hayloft, and a metal roof. Right across the road is the westerly boundary of Goose Lake Drumlins Reserve Area with over 2,200 acres of nature including a great stand of tamaracks, many hardwood forested areas, prairie grasslands, and some wonderful marshes. Enjoy!!!

4335 Missouri Rd, Deerfield

6923 Dominion Dr, Madison
$464,900
3 Beds ⋅ 3 Baths ⋅ 2035365 MLS ⋅ ACTIVE Status
Welcome home to this inviting 3-bedroom, 2.5 bath home situated on a spacious lot! Step inside to discover beautiful wood floors, impressive 9-foot ceilings, and a thoughtfully designed layout offering both comfort and functionality. The primary suite features stunning cathedral ceilings, creating an open and airy retreat. Enjoy the convivence of a wider driveway & an attached garage with an additional 4 ft of space, perfect for extra storage, tools, or rec equipment. Just off the back of the home, the three-season room provides wonderful space to relax, entertain or enjoy the views of the backyard. With its generous lot size, desirable features, and inviting living spaces, this home offers a great combination of charm, comfort and practicality!

6923 Dominion Dr, Madison

269 Goede Rd, Albion
$469,000
3 Beds ⋅ 2 Baths ⋅ 2034695 MLS ⋅ ACTIVE Status
Enjoy the space and privacy of 1.88 acres with this beautifully updated ranch home! Major updates have already been taken care of, including new siding, windows, metal roof, flooring throughout, fresh paint, A/C and furnace. Original character shines through with charming arched doorways and timeless details. The finished lower level offers additional living space with a walkout to the patio and hot tub, plus a spacious backyard fire pit area perfect for entertaining. Convenient laundry is available on both the main and lower levels. A new 24X27 Cleary 2-car detached garage/workshop, built in 2025, provides plenty of space for vehicles, hobbies, storage, and more, with 220-amp service. This property offers the perfect combination of updates, character, acreage, and functionality!

269 Goede Rd, Albion

5302 Camilla Rd, Madison
$450,000
3 Beds ⋅ 2 Baths ⋅ 2035282 MLS ⋅ ACTIVE Status
Immaculate home in peaceful neighborhood, over $80K in updates added in last two years! New in 2026: roof, AC, kitchen cabinets, quartz countertop, backsplash, bathrooms, all appliances, LVP, carpet and pad, paint, base trim, lighting and plumbing fixtures. Furnace new in 2025. Step inside to professional craftsmanship in the oak floors, railings, and crown molding. The kitchen features quartz counters, an undermount sink, timeless subway tile backsplash, soft-close cabinets, and beautiful stainless-steel appliances. A dining area flows to the living room, and a sitting room with a wood-burning fireplace overlooks the huge backyard. Upstairs are three bedrooms, including a primary with two closets, one a walk-in, and a full bath with dual entry. Both baths, including the main-level half, have new fixtures, quartz, and LVP flooring. Relax on the covered porch or large back deck. The lower level has a clean shop room and space to finish or use as storage. Small shed in back yard.

5302 Camilla Rd, Madison

3234 Clove Dr, Madison
$424,900
4 Beds ⋅ 3 Baths ⋅ 2035174 MLS ⋅ ACTIVE Status
5.5% Assumable VA Loan Available! Situated on a spacious half-acre lot backing to greenspace, this 4-bedroom, 3-bath home offers plenty of space and potential! The living room features vaulted ceilings, a wood-burning fireplace, and hardwood floors that extend into the dining room, with access to a wraparound deck overlooking the backyard. The main-level primary bedroom includes vaulted ceilings and a private en-suite bathroom. The finished walkout lower level offers additional living space with a large rec room, fourth bedroom, full bathroom, and direct access to the backyard. Enjoy a generous yard with room for entertaining, gardening, or relaxing, plus a storage shed. Just steps from Westchester Gardens Park and minutes from shopping, dining, and everything Madison's east side has to offer. Bring your ideas and make this home your own!

3234 Clove Dr, Madison

8456 Messerschmidt Dr, Springdale
$1,200,000
3 Beds ⋅ 3 Baths ⋅ 2035160 MLS ⋅ ACTIVE UNDER CONTRACT Status
Set on over 15 acres of rolling Wisconsin countryside, this exceptional property offers privacy, sweeping views and room to roam, all just minutes from Verona and an easy drive to Madison. A 36x78 barn offers endless possibilities for equestrian use, equipment or hobbies, while a dedicated wood shop is ideal for projects of every scale. The open grounds are perfect for gardens, pasture or recreation. Inside, enjoy formal living and dining rooms, a spacious family room, eat-in kitchen, private primary suite, home office and well-appointed mudroom. A valuable land-split option adds to the property’s appeal. Whether you envision an artisan’s retreat or private country sanctuary, this unique estate offers space and versatility in a coveted location. See feature sheet for a complete list of improvements.

8456 Messerschmidt Dr, Springdale

3572 Rankin Rd, Blooming Grove
$400,000
3 Beds ⋅ 3 Baths ⋅ 2034528 MLS ⋅ ACTIVE Status
Showings begin 10/24. Inviting home full of character on a spacious lot with mature trees backing to a park in McFarland’s sought after April Hills neighborhood. A public easement on the east side prevents building there, preserving privacy. The open layout creates an easy flow for entertaining and everyday living. Unwind in your private bedroom with a full ensuite bath. The finished lower level features a family room for movie or game nights and a walkout to the backyard. Spend warm weather days on the deck or patio overlooking the expansive, fenced-in backyard, ideal for summer BBQs and gatherings. A 26 foot deep two car attached garage offers extra room for a workshop or storage. Enjoy bird watching from your kitchen with a custom bird feeder display mount. Meticulously maintained, with low Blooming Grove taxes in the highly rated McFarland School District. A fantastic opportunity to enjoy comfort and convenience.

3572 Rankin Rd, Blooming Grove

4713 Fond Du Lac Trl, Madison
$1,350,000
4 Beds ⋅ 3 Baths ⋅ 2035148 MLS ⋅ ACTIVE Status
Welcome to 4713 Fond du Lac Trail! Offering 4 bedrooms, 2.5 baths, and over 3,500 square feet, this spacious home sits on a beautiful, tree-lined lot in an established Madison neighborhood. Inside, you will find hardwood floors, a generous living room with fireplace, formal dining room, and a spacious kitchen with ample cabinetry. The finished lower level provides additional space for entertaining, recreation, or hobbies. Outside, enjoy the screened porch, expansive backyard, and gazebo with patio seating area added in 2024, perfect for relaxing or hosting gatherings. Owned solar panels and an electric vehicle charger add modern convenience, while updated mechanicals, including the furnace, A/C, and water heater, offer added peace of mind. A fantastic combination of space, comfort, and outdoor living!

4713 Fond Du Lac Trl, Madison

2006 Cameron Dr, Madison
$409,900
3 Beds ⋅ 2 Baths ⋅ 2035128 MLS ⋅ ACTIVE Status
Conveniently located near schools, numerous parks, walking paths, a library, shops, and restaurants, this 3-bedroom home offers easy access to many of Madison’s everyday amenities. With the Beltline just 1.5 miles away, commuting around the area is simple and convenient. Inside, the open kitchen connects easily with the main living spaces, including an additional living room that provides flexibility for everyday living or entertaining. The finished basement adds even more usable space with a rec room ideal for relaxing, games, or hobbies. Outside, enjoy a fenced yard, screened porch, yard shed, and a large attached 2-car garage offering plenty of room for vehicles and storage. A comfortable home with flexible living space in a well-connected Madison location.

2006 Cameron Dr, Madison

6661 Charlie Grimm Rd, Windsor
$349,500
3 Beds ⋅ 2 Baths ⋅ 2035112 MLS ⋅ ACTIVE Status
NOT YOUR COOKIE-CUTTER CONDO! This unique multi-level half-duplex offers character, style, and spacious living overlooking Lake Windsor Golf Course! Soaring vaulted ceilings and abundant natural light highlight the open living and dining areas, featuring a gas log brick fireplace. The versatile layout includes 3 bedrooms, a primary bedroom loft, generous dining room with deck access, and an eat-in kitchen with patio doors to a fenced backyard retreat. Enjoy the stamped concrete patio, fire pit, storage shed, and golf course views! Updates include stainless steel kitchen appliances, front-load stackable washer/dryer, vinyl plank flooring, carpeting, central air, windows, and patio doors. Features include first-floor laundry, a 2-car garage, Ring doorbell and security system. Conveniently located near Lake Windsor Country Club and Windsor Athletic Club, with easy access to Madison, I-39/90/94, and Dane County Regional Airport. Unique style and space make this home a must-see!

6661 Charlie Grimm Rd, Windsor

6021 Raymond Rd, Madison
$350,000
3 Beds ⋅ 2 Baths ⋅ 2035108 MLS ⋅ ACTIVE UNDER CONTRACT Status
Welcome home to this inviting 3 bedroom, 1.5 bathroom ranch situated on a large lot in a convenient westside location. Hardwood floors flow throughout the main level, complemented by newer paint and updated light fixtures. The kitchen features a new refrigerator and microwave, both replaced in 2026. The updated bathrooms include a convenient private half bath attached to the primary bedroom. Additional improvements include a new dryer in 2025, washer in 2026 & hot water heater in 2022. The spacious basement is a fun flashback to the home’s 1960s roots and offers plenty of room to use your imagination and bring the space back to life. Inside, the home feels comfortable and quiet, while the fenced backyard and patio provide a peaceful, private retreat. An attached 2 car garage completes this well maintained home with easy access to shopping, dining, parks and everyday conveniences.

6021 Raymond Rd, Madison

8042 County Road G, Springdale
$549,900
3 Beds ⋅ 3 Baths ⋅ 2035103 MLS ⋅ ACTIVE UNDER CONTRACT Status
Escape to quiet country living just outside Verona on a peaceful 1.27-acre lot. Completely renovated in 2019, this bright, sun-filled home offers an inviting open-concept layout where the kitchen, dining and living areas flow together beautifully. The kitchen is a true showpiece, featuring handcrafted Amish-made cabinetry, abundant storage, a classic farmhouse sink, granite countertops and stainless steel appliances. Retreat to the private primary suite, complete with two walk-in closets and an en suite bath with a tiled shower and dual vanities. A second main-level bedroom and a main bath with tub round out the main floor. The finished lower level offers a cozy family room made for relaxing, plus an additional bedroom and a third full bath. With newer mechanicals, roof and pressure tank, this home pairs country tranquility with true peace of mind.

8042 County Road G, Springdale

738 Western Ave, Madison
$519,900
3 Beds ⋅ 2 Baths ⋅ 2035021 MLS ⋅ ACTIVE Status
LOCATION! LOCATION! LOCATION! Sought after Dungeon Monroe Neighborhood ACROSS FROM ARBORETUM! NEAR EDGEWOOD! THE BIKE Trl IS RIGHT THERE!! 1 HOUSE UP FROM VIBRANT MONROE ST! Minutes to All, Madison Hospitals-Perfect for Residence's and traveling nurses! Jump on the Cap City bike path to UW University & Edgewood School & College! Huge demand for this area right off Monroe St across from Wingra School! This One Owner has space for Everyone to Enjoy! Walk-in and notice the large Hardwood front living rm! Kitchen, Dinette and Sitting room overlook a private mature fenced back yard! Take a few steps up to the bedroom wing offering 3 generous hardwood bedrooms and a full bath! 2nd bath & nice bsmt for storage! May be room to build a garage behind home. There is a Nice concrete drive give plenty of parking and easy access to 2nd entrance offering convenient direct access to the kitchen! See message from the City of Madison regarding building a garage! A must see!

738 Western Ave, Madison

437 Yahara St, Deforest
$429,900
4 Beds ⋅ 2 Baths ⋅ 2035008 MLS ⋅ ACTIVE Status
Pride of Ownership Shines Throughout This Beautiful Colonial! Lovingly owned by this family for 53 years, this pampered two-story Colonial is a wonderful place to call home! Offering 4 bedrooms, 2 full baths & numerous updates, this home combines timeless charm w/comfortable living spaces. The spacious, updated kitchen features plenty of room for meal preparation & includes a dinette area, while the formal dining room is perfect for entertaining. Relax in the inviting living room or the spacious main-floor sunroom, offering a wonderful spot to enjoy the changing seasons. A breezeway & screened porch add even more charm & versatility. The finished LL provides additional living & recreation space, with convenient exterior access. Major updates include a newer Furnace, C/A, and Roof. Outside, you'll love the spacious backyard featuring mature trees with a handy storage building. A special home that has been exceptionally cared for & is ready for its next chapter!

437 Yahara St, Deforest

6306 Jacobs Way, Madison
$430,000
3 Beds ⋅ 2 Baths ⋅ 2034923 MLS ⋅ ACTIVE Status
Welcome to Prairie Hills Neighborhood! This inviting two-story Colonial offers comfort, character, and a convenient location near parks and bike trails. The kitchen features solid surface countertops, quality cabinetry, ample storage, and updated overhead lighting. LVP flooring flows throughout the main level, where a cozy wood burning fireplace creates a warm atmosphere. The living room connects to the dining room, offering a welcoming space for everyday living and entertaining, with a convenient half bath nearby. Step outside to an oversized, secluded backyard surrounded by mature trees, complete with a spacious deck for relaxing or gathering with friends. Upstairs, you’ll find three bedrooms and a full bath, with fresh paint throughout the second floor and new carpeting. The lower level bonus room is perfect for a playroom or TV room. Enjoy nearby parks, bike trails, and local wildlife, you might even spot wild turkeys or flying squirrels!

6306 Jacobs Way, Madison

4554 Sandpiper Trl, Cottage Grove
$499,000
4 Beds ⋅ 3 Baths ⋅ 2034861 MLS ⋅ ACTIVE Status
SELLER IS WILLING TO BUY DOWN YOUR INTEREST RATE! Enjoy the space, flexibility, and charm of ranch-style living on a generous 0.73-acre lot in Cottage Grove! Offering 4 bedrooms, 3 bathrooms, and approximately 2,186 square feet, this home features two inviting living spaces and a bonus lower level with a bar, creating plenty of room to relax, entertain, and gather. Recent improvements include a new roof, garage door, washer and dryer, and dishwasher in 2026, along with a Kohler sink and disposal updated in 2025. Step outside to enjoy the deck, patio pavers, firepit, large garden, shed, and spacious yard, with room to make the most of outdoor living. There is even an invisible fence in the front and back yards. If you prefer a physical fence, you can have one installed. With its versatile layout, substantial lot, and valuable updates, this home offers a wonderful opportunity to settle in and make it your own!

4554 Sandpiper Trl, Cottage Grove

465 Caromar Dr, Madison
$700,000
4 Beds ⋅ 2 Baths ⋅ 2034853 MLS ⋅ ACTIVE Status
Welcome home to this charming, light filled home in Madison's highly desirable Westmorland neighborhood! Full of character and thoughtfully updated throughout, this home offers beautiful hardwood floors and a surprisingly open, inviting floor plan. A new timeless kitchen with the perfect touches will surly impress. With spacious living areas flowing into the sunroom/family room, where you can step outside to the deck and enjoy the beautiful fenced backyard, perfect for entertaining or relaxing. A convenient half bath completes the main level. Upstairs, you'll find four generously sized bedrooms and the updated full bath. Many updates including siding, roof, kitchen, baths, and more add to the appeal. Enjoy the charm of an established neighborhood with shopping, dining, parks, the library and everyday conveniences. This one truly feels like home.

465 Caromar Dr, Madison

1942 Vahlen St, Madison
$299,000
2 Beds ⋅ 1 Baths ⋅ 2034839 MLS ⋅ ACTIVE Status
Welcome to this charming well maintained cape cod on Madison's north east side. This two bedroom home is move-in ready for its next owners — no deferred maintenance projects! The large backyard has a gorgeous established garden with much more room to garden, entertain, or simply unwind. This lovely home has a new roof (‘24), gutters (‘24), central ac (‘24), water softener, water heater, cedar privacy fence, energy efficient attic insulation, and more. An attached one car garage adds everyday convenience. The unfinished walk-up attic provides potential for increasing space, and even has plumbing roughed in for this future potential. Currently, added insulation in the attic helps keep this home very energy efficient and saves on heating and cooling expenses.

1942 Vahlen St, Madison

This information, provided by seller, listing broker, and other parties, may not have been verified. Copyright 2026 South Central Wisconsin MLS Corporation. All rights reserved. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify perspective properties consumers may be interested in purchasing.

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