Homes for Sale near Milestone Democratic School

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  /32

  $409,900

  Open Sat 11AM - 1PM $2K PRICE INCREASE

  • 3 Beds
  • 2.5 Baths
  • 1,532 Sq Ft

  5730 Tranquility Trail, Madison, WI 53718

  Smarter Living in Autumn Lake! Get the maximum 'bang for your buck' per finished square foot with this like-new construction twin home, delivering incredible affordability and premium quality without compromise! Nestled in Madison’s desirable Autumn Lake Subdivision—zoned for Sun Prairie Schools—this near-mint condition home offers 1,532 finished sq ft, 3 bedrooms, 2.5 baths, and a 2-car attached

  Justin Witkins RE/MAX Preferred

  5730 Tranquility Trail, Madison, WI 53718
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  /24

  $600,000

  $40K PRICE DROP

  • 2,560 Sq Ft

  2069 Winnebago St, Madison, WI 53704

  Prime Near East Side 3-unit investment opportunity just steps from Schenk’s Corners. This well-maintained property offers character, strong rental history, and highly desirable layouts, with hardwood floors, formal dining rooms in the first and second-floor units, inviting porches, a private third-floor balcony, and three off-street parking spaces. Major improvements include electrical updates, a

  Sarah Gabrielse Real Broker LLC

  2069 Winnebago St, Madison, WI 53704
• 

  

  

  /10

  $164,900

  • Land
  • 6,534 Sq Ft
  • $1,099,333 per Acre

  4767 Lacy Rd, Fitchburg, WI 53711

  Build your dream home in Terravessa, a thoughtfully planned Fitchburg community featuring parks, green space, walking and biking trails, and nearby lake access. Conveniently located near shopping, event venues, in-neighborhood dining, cafés, and school. Served by the Oregon School District and connected to the greater Madison trail network, including the Southwest Commuter Trail. Lot sale is

  Aeryn Barry Tim O'Brien Homes LLC

  4767 Lacy Rd, Fitchburg, WI 53711
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  /44

  $449,900

  • 3 Beds
  • 3 Baths
  • 2,664 Sq Ft

  1816 Dondee Rd, Madison, WI 53716

  Welcome home to easy, low-maintenance living in this beautifully maintained duplex condo on Madison’s desirable east side. The inviting interior features two gas fireplaces, creating warm and comfortable gathering spaces to enjoy throughout the year. Relax with your morning coffee, entertain guests, or take in the changing seasons from the bright four-season porch. A recently replaced roof offers

  Chris Alexander NextHome Midwest

  1816 Dondee Rd, Madison, WI 53716
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  /35

  $589,900

  Open Sat 12:30PM - 1:30PM $10K PRICE DROP

  • 7 Beds
  • 3 Baths
  • 2,280 Sq Ft

  114 W Olin Ave, Madison, WI 53715

  Rare opportunity to own one of Madison's few true seven bedroom homes, offering exceptional flexibility for multigenerational living, home offices, or evolving lifestyle needs. Built with enduring quality and meticulously maintained by the same family since it was constructed, this spacious brick home features a floor plan rarely found in today's market. The sun filled main level welcomes you

  Erika Haar CCL Management

  114 W Olin Ave, Madison, WI 53715
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  /33

  $545,000

  $55K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,480 Sq Ft

  415 S Livingston St, Madison, WI 53703

  Welcome to the hearty of Madison's vibrant Willy St neighborhood! This charming two story home offers the perfect blend of historic character and urban convenience, just minutes from the Sylvee, Breese Stevens Field, downtown, the Capitol Square, and countless locally owned restaurants, coffee shops, breweries, and boutiques. Inside, you'll find spacious living areas filled with natural light,

  Chris Alexander NextHome Midwest

  415 S Livingston St, Madison, WI 53703
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  /48

  $839,900

  New Construction $10K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,305 Sq Ft

  2017 Wellington Place, Cottage Grove, WI 53527

  This stunning, custom-built, brand-new ranch-style home by Maverick Homes offers 2,305 square feet of modern living space designed for both comfort and elegance. Situated on a generous lot, the property provides ample space for outdoor activities and future landscaping opportunities. The three-car garage offers plenty of room for vehicles and additional storage. The spacious, unfinished lower

  Matt Winzenried Realty Executives Cooper Spransy

  2017 Wellington Place, Cottage Grove, WI 53527
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  /90

  $764,999

  $20K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 4,118 Sq Ft

  517 Buss Rd, Cottage Grove, WI 53527

  Motivated seller, relocating, price reduction. This immaculate colonial 5 bdrm, 3.5 bath, offers over 4100 sqft, plus a full unfinished lower level that includes a bath rough in & an egress window. This open floor plan offers a very large kitchen w/lots of beautiful maple cabinets, walk-in pantry, upgraded GE SS appliances, an oversized island bar & lovely morning room. Open & airy living/family

  Nancy Riemenapp First Weber, Inc

  517 Buss Rd, Cottage Grove, WI 53527
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  /51

  $795,000

  Open Sun 11AM - 1PM $55K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 2,184 Sq Ft

  4001 Monona Dr Unit 204, Monona, WI 53716

  Lake Monona waterfront condo w/panoramic view of the Capitol and downtown skyline. Enjoy sunrise and sunsets from your sunroom and expansive windows overlooking the lake. One boat slip avail to new owner. First floor building entry. Foyer with large closet, spacious living space with incredible views, 3-sided gas fireplace, formal dining, office & sunroom. Spacious kitchen offers plenty of

  Jaclyn Cunningham First Weber Inc

  4001 Monona Dr Unit 204, Monona, WI 53716
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  /12

  $5,990,000

  • Land
  • 9.8 Acres
  • $611,224 per Acre

  3080 County Road Mm, Fitchburg, WI 53711

  REDEVELOPMENT OPPORTUNITY - Prime location on the corner of Clayton Rd. & Highway MM in Fitchburg, WI. Priced at just $5,990,000, this 9.8-acre parcel offers endless potential for redevelopment. Situated on a beautiful hilltop, with breathtaking views of downtown Madison, Lake Monona, and the surrounding countryside, the property is just minutes away from the proposed development of the Dane

  James Stopple Madison Property Management, Inc.

  3080 County Road Mm, Fitchburg, WI 53711
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  /61

  $2,999,999

  • 4 Beds
  • 3 Baths
  • 3,578 Sq Ft

  155 E Wilson St Unit 702, Madison, WI 53703

  Architect-owned dual-level penthouse offers a serene retreat where high modernism meets panoramic lake views. Personally designed by renowned architect Kenton Peters, the home focuses on airy, expansive, environmentally layered spaces with carefully curated interiors that balance grand entertaining with intimate living. A main-level bedroom suite offers exceptional flexibility, complete with an

  Maria Antoinette Cannarella Restaino & Associates

  155 E Wilson St Unit 702, Madison, WI 53703
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  /54

  $400,000

  $35K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,463 Sq Ft

  1001 Glacier Hill Dr, Madison, WI 53704

  Set on a desirable corner lot in Ridgewood neighborhood with mature trees and unobstructed views of Glacier Hill Park. Enjoy the privacy of the backyard retreat, perfect for relaxing or entertaining, with a dinette featuring a patio door that opens directly to the outdoor space. Major improvements provide peace of mind, including a new roof (2023), new furnace and A/C (2023), and water heater

  Ikbal Bieff Restaino & Associates

  1001 Glacier Hill Dr, Madison, WI 53704
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  /59

  $400,000

  $25K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,466 Sq Ft

  400 Frost Woods Rd, Monona, WI 53716

  COME HOME TO COMFORT! This well-maintained classic ranch is now available. The bright living room includes a large picture window, solid hard wood floors, and plenty of room for large gatherings. Step into the eat in kitchen with freshly painted cabinets. Three bedrooms on the main floor sit next to the updated main bathroom with 2 sinks. Downstairs offers a versatile rec room, half bathroom,

  The Lavik Home Team EXP Realty, LLC

  400 Frost Woods Rd, Monona, WI 53716
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  /43

  $579,900

  • 3 Beds
  • 2 Baths
  • 2,003 Sq Ft

  5514 Maddy Pass, Madison, WI 53718

  Like new and absolutely stunning, this 3-bedroom ranch offers the perfect blend of style and comfort. Vaulted ceilings and abundant natural light create a bright, open feel throughout the thoughtfully designed floor plan. The elegant kitchen features stainless steel appliances, a sleek tile backsplash, and quartz center island that overlooks the spacious living and dining area, making

  Dustin Laufenberg MHB Real Estate

  5514 Maddy Pass, Madison, WI 53718
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  /20

  $405,000

  $10K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 952 Sq Ft

  405 Rogers St, Madison, WI 53703

  Charming 2-bedroom, 1-bath home in the heart of Madison's vibrant East Side! This prime location puts you within walking distance of some of the city's best restaurants, entertainment, and the lake; perfect for enjoying everything Madison has to offer right outside your door. Whether you're grabbing coffee at a neighborhood cafe, catching a show, or taking a sunset stroll along the water, this

  Tiffany Malone Compass Real Estate Wisconsin

  405 Rogers St, Madison, WI 53703
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  /10

  $169,900

  • Land
  • 6,534 Sq Ft
  • $1,132,667 per Acre

  4759 Lacy Rd, Fitchburg, WI 53711

  Build your dream home in Terravessa, a thoughtfully planned Fitchburg community featuring parks, green space, walking and biking trails, and nearby lake access. Conveniently located near shopping, event venues, in-neighborhood dining, cafés, and school. Served by the Oregon School District and connected to the greater Madison trail network, including the Southwest Commuter Trail. Lot sale is

  Aeryn Barry Tim O'Brien Homes LLC

  4759 Lacy Rd, Fitchburg, WI 53711
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  /2

  $579,900

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,045 Sq Ft

  5919 Rosewood Dr, Mc Farland, WI 53558

  Renderings are for illustrative purposes only. Final colors, finishes, and landscaping will differ.All prices, promotions and specifications are subject to change at any time without notice based on the discretion of Veridian Homes.

  Veridian Homes Builder

  5919 Rosewood Dr, Mc Farland, WI 53558
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  /10

  $117,900

  • Land
  • 6,534 Sq Ft
  • $786,000 per Acre

  4766 Lacy Rd, Fitchburg, WI 53711

  Build your dream home in Terravessa, a thoughtfully planned Fitchburg community featuring parks, green space, walking and biking trails, and nearby lake access. Conveniently located near shopping, event venues, in-neighborhood dining, cafés, and school. Served by the Oregon School District and connected to the greater Madison trail network, including the Southwest Commuter Trail. Lot sale is

  Aeryn Barry Tim O'Brien Homes LLC

  4766 Lacy Rd, Fitchburg, WI 53711
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  /69

  $399,900

  $30K PRICE DROP

  • 1,565 Sq Ft

  3414 Richard St, Madison, WI 53714

  SO MANY OPTIONS! Well-maintained side-by-side duplex! Ideal for multigenerational living, extended guests, or future income potential. Features include separate entrances, central A/C, shared laundry, dedicated off-street parking, and a brand-new Lifetime OC Flex Roof (Class 4) with new wood in June 2026. Near Olbrich Park & Gardens, the Lake Monona Bike Loop, and just a short walk across the new

  Matt Kornstedt Stark Company, REALTORS

  3414 Richard St, Madison, WI 53714
• 

  

  /23

  $900,000

  • 2,697 Sq Ft

  124 N Franklin St, Madison, WI 53703

  Rarely do you find a 2-flat with this much size, income, and upside all in one package! Located right next to James Madison Park, this 8-bedroom property is already generating over $7,100/month with potential to push rents beyond $8,200/month. The oversized units, off-street parking, unbeatable location, and classic charm make these apartments incredibly easy to rent year after year. Well

  Imani Jones EXIT Realty HGM

  124 N Franklin St, Madison, WI 53703
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  /63

  $719,000

  $31K PRICE DROP

  • 1,730 Sq Ft

  137 Proudfit St, Madison, WI 53715

  Opportunity awaits with this charming 2-unit investment property in a highly desirable Madison location! Featuring a vacant 4-bedroom, 2-bath unit, this property offers excellent flexibility for an owner-occupant or the ability to maximize rental income with a new tenant. The second unit is a cozy 1-bedroom, 1-bath apartment, providing an additional income stream. Full of timeless character and

  Rose Freidel First Weber Inc

  137 Proudfit St, Madison, WI 53715
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  /22

  $417,900

  $25K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,020 Sq Ft

  309 W Washington Ave Unit 212, Madison, WI 53703

  This condo in the heart of downtown offers floor to ceiling windows, balcony and beautiful views. Open concept kitchen features breakfast bar, quartz counters, gas range and GE stainless appliances. Engineered wood flooring in main living area. Primary bedroom has walk-in closet and organizers. Large bathroom with dual vanity, separate tub and tiled walk-in shower. Storage unit located on same

  Marc Gerothanas First Weber Inc

  309 W Washington Ave Unit 212, Madison, WI 53703
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  /2

  $189,000

  • Land
  • 14,374 Sq Ft
  • $572,727 per Acre

  2994 London Ave, Cottage Grove, WI 53527

  Beautiful wooded walk-out lot with a full South backyard exposure. Located in the highly desirable Westlawn neighborhood. Building permit available now.

  Andrew Homburg Homburg Realty Inc

  2994 London Ave, Cottage Grove, WI 53527
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  /8

  $125,000

  • Land
  • 7,840 Sq Ft
  • $694,444 per Acre

  237 Wyalusing Dr, Madison, WI 53718

  Rare opportunity in Madison’s sought-after Reston Heights Subdivision! Hard-to-find single-family lots in a master-planned community with parks, greenspace, and trails. Lots will be ready to build by mid-November — bring your own builder and design your dream home! Enjoy green space bordering these lots and a large park across the street. Prime location near the Door Creek Corridor, new schools,

  Mark Nortman First Weber Inc

  237 Wyalusing Dr, Madison, WI 53718
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  /8

  $125,000

  • Land
  • 7,405 Sq Ft
  • $735,294 per Acre

  241 Wyalusing Dr, Madison, WI 53718

  Rare opportunity in Madison’s sought-after Reston Heights Subdivision! Hard-to-find single-family lots in a master-planned community with parks, greenspace, and trails. Lots will be ready to build by mid-November — bring your own builder and design your dream home! Enjoy green space bordering these lots and a large park across the street. Prime location near the Door Creek Corridor, new schools,

  Mark Nortman First Weber Inc

  241 Wyalusing Dr, Madison, WI 53718
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  /55

  $475,000

  $15K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,164 Sq Ft

  5606 Kalas St, Madison, WI 53716

  Remodeled and updated 3 bedroom, 2 full bathroom open concept home in the City of Madison with an attached 3 car garage, game room, massive deck and fenced in backyard! This bi-level/raised ranch property will amaze you as soon as you walk in and see the remodeled and updated living room and kitchen complete with wood floors, custom cabinets, quartz countertops, a large island, double oven, gas

  Brandon Housley Artisan Graham Real Estate

  5606 Kalas St, Madison, WI 53716
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  /42

  $463,500

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,572 Sq Ft

  The Harlow Plan at Autumn Lake - Woods, Madison, WI 53718

  One look at the primary suite in The Harlow and you’ll feel your pulse quicken... an inviting retreat with a private bath and a closet spacious enough to dance in. The kitchen steals the show with a generous island perfect for entertaining, paired with a sunny set of patio doors that welcome in morning light for a quiet cup of coffee before the day begins. This thoughtfully designed single-level

  Veridian Homes Builder

  1803 Autumn Lake Pkwy Unit 36468679, Madison, WI 53718
• 

  Price To Be Determined

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,977 Sq Ft

  The Vienna Plan at Jannah Village, Madison, WI 53718

  Loos Homes Builder

  5805 Bridle Way Unit 39356499, Madison, WI 53718
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  /46

  $629,900

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,503 Sq Ft

  5616 Divine St, Madison, WI 53718

  Estimated completion 9/15/2026. New pictures coming soon! Brand New Construction in a desirable East Madison location within the Sun Prairie School District! This spacious 4-bedroom home offers modern design, quality finishes, and room to grow. Luxury vinyl plank flooring flows throughout the entire home, creating a stylish and low maintenance finish. The open concept layout features a

  Lindsay Hagens Compass Real Estate Wisconsin

  5616 Divine St, Madison, WI 53718
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  /36

  $799,900

  • 3,474 Sq Ft

  2109-2113 Spring Dreams Ln, Madison, WI 53718

  Built in 2023, this modern twin-style duplex in the Village at Autumn Lake presents an outstanding investment or owner-occupant opportunity. Each spacious unit offers 3 bedrooms, 2.5 baths and a bright, open layout with contemporary finishes throughout. The main level features a generous great room, dining area, well-appointed kitchen and convenient in-unit laundry. Each side also includes a

  R3bel Real Estat Group Century 21 Affiliated

  2109-2113 Spring Dreams Ln, Madison, WI 53718
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  /54

  $199,000

  $12K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 852 Sq Ft

  6 Sherman Terrace Unit 5, Madison, WI 53704

  Wasting your money on rent every month? Making your landlord rich? Here is an affordable condo in Sherman Terrace. On the bus line, convenient to Downtown and UW, stone's throw from Lake Mendota, Tenney Park. Is this condo in top condition? No. Does it need some upgrades? Yes. Seller is moving out of town. Is this an opportunity for you? Yes! A smart opportunity to build equity while creating a

  Matt Kornstedt Stark Company, REALTORS

  6 Sherman Terrace Unit 5, Madison, WI 53704
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  /67

  $1,550,000

  • 4 Beds
  • 3 Baths
  • 3,649 Sq Ft

  3022 Waubesa Ave, Madison, WI 53711

  Experience exceptional Lake Waubesa living with 50 feet of coveted frontage and sweeping water views. This thoughtfully designed 4-bedroom, 3-bath home features a bright, open-concept main level ideal for daily living and entertaining. The four-season porch opens to a spacious lakeside deck, perfect for morning coffee or sunset gatherings. The serene primary suite includes lake views, a walk-in

  Lisa Piekarski-Knutson Real Broker LLC

  3022 Waubesa Ave, Madison, WI 53711
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  /55

  $450,000

  $109K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,650 Sq Ft

  2146 Winnebago St, Madison, WI 53704

  Many items are updated including siding, roofing, windows, doors, carpets, floors, screen porch, light fixtures and receptacles, central AC and furnace. Make this house on home on well known Winnebago street, which close to many small businesses. Room dimensions are estimated. Owner is a broker.

  Koua Vang Koua Vang

  2146 Winnebago St, Madison, WI 53704
• 

  

  /10

  $169,900

  • Land
  • 7,840 Sq Ft
  • $943,889 per Acre

  4775 Lacy Rd, Fitchburg, WI 53711

  Build your dream home in Terravessa, a thoughtfully planned Fitchburg community featuring parks, green space, walking and biking trails, and nearby lake access. Conveniently located near shopping, event venues, in-neighborhood dining, cafés, and school. Served by the Oregon School District and connected to the greater Madison trail network, including the Southwest Commuter Trail. Lot sale is

  Aeryn Barry Tim O'Brien Homes LLC

  4775 Lacy Rd, Fitchburg, WI 53711
• 

  /2

  $160,000

  • Land
  • 12,632 Sq Ft
  • $551,724 per Acre

  2993 Wellington Place, Cottage Grove, WI 53527

  Beautiful partial exposure lot on the corner of Wellington and Meadowlark in the highly desirable Westlawn Estates neighborhood in the Village of Cottage Grove. Walk or take the paths and sidewalks to the respected Glacial Drumlin Middle School and Granite Ridge 3-5 school. Exceptionally built custom homes abound in this neighborhood. Work with a custom builder of your choosing and come see

  Andrew Homburg Homburg Realty Inc

  2993 Wellington Place, Cottage Grove, WI 53527
• 

  

  /47

  $239,900

  Open Sun 1PM - 3PM $10K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,185 Sq Ft

  141 Metro Terrace Unit 203, Madison, WI 53718

  Whether you're buying your first home, looking for low-maintenance living & community, or hoping to offset your mortgage w/ a roommate, Unit 203 at 141 Metro Terrace, conveniently located for your commute & daily needs, is an affordable, natural choice for YOU! This 2 bed, 2 bath, thoughtfully designed condo, w/ newer carpet, light fixtures & windows, in unit laundry, an updated balcony, &

  Tiffany Shields Century 21 Affiliated

  141 Metro Terrace Unit 203, Madison, WI 53718
• 

  

  /62

  $445,000

  • 4 Beds
  • 2.5 Baths
  • 2,218 Sq Ft

  414 Jubilee Ln, Madison, WI 53718

  Welcome home to this beautifully maintained 4-bedroom-plus residence, set on over 1/3 of an acre with mature trees, beautiful flowers & inviting outdoor spaces. The main level offers 4 comfortable bedrooms, including a spacious Primary Bedroom & a large Great Room creating an open, welcoming atmosphere. The kitchen & dining area flow seamlessly into the Family Room, providing an ideal layout for

  Liz Potter RE/MAX Preferred

  414 Jubilee Ln, Madison, WI 53718
• 

  

  /10

  $546,900

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,556 Sq Ft

  4790 Suelo Rd, Fitchburg, WI 53711

  Healthy, Energy-Efficient, NEW Construction, Built for the way you live! Discover easy living in Terravessa, a vibrant community just 12 minutes from the heart of downtown w/ convenient access to local shops and amenities. Nestled beside a stunning 170-acre nature preserve with scenic walking trails, this home offers the perfect blend of comfort and nature. This charming home features an

  Aeryn Barry Tim O'Brien Homes LLC

  4790 Suelo Rd, Fitchburg, WI 53711
• 

  

  /4

  $158,900

  • Land
  • 7,405 Sq Ft
  • $934,706 per Acre

  2936 Parsnip Dr, Fitchburg, WI 53711

  Build your dream home with Tim O'Brien Homes on a lot with a private rear yard lined with mature trees. Terravessa is a thoughtfully planned Fitchburg community featuring parks, green space, walking and biking trails, and nearby lake access. Conveniently located near shopping, event venues, in-neighborhood dining, cafés, and school. Served by the Oregon School District and connected to the

  Aeryn Barry Tim O'Brien Homes LLC

  2936 Parsnip Dr, Fitchburg, WI 53711
• 

  

  /24

  $335,000

  • 3 Beds
  • 2 Baths
  • 1,320 Sq Ft

  5804 Sauk Ln, Mc Farland, WI 53558

  Welcome home to this beautifully renovated half-duplex condo located in the highly desirable McFarland School District! Perfectly situated w/ Woodland Estates Park right in your backyard, you'll enjoy peaceful views & convenient access to green space & outdoor recreation. This move-in ready home features 3 bed/2 bath w/ updates throughout. The completely remodeled interior boasts all new

  Erin Bickelhaupt Realty Executives Capital City

  5804 Sauk Ln, Mc Farland, WI 53558

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