Homes for Sale near Milestone Democratic School

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  /33

  $395,000

  $20K PRICE DROP

  • 1,706 Sq Ft

  1913 E Washington Ave Unit 1, Madison, WI 53704

  Looking to break into the investment market or expand your portfolio in Madison? This East Washington Ave 2-flat offers a prime location w/ strong upside potential in a high-demand rental area. Ideal for investors, owner-occupants, or 1st-time multifamily buyers, the property features MTM leases, providing flexibility for future updates & increased income potential. Each unit includes 2 BR, 1 BA,

  Carolyn Doering Bunbury & Assoc, REALTORS

  1913 E Washington Ave Unit 1, Madison, WI 53704
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  /49

  $675,000

  $125K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 4,030 Sq Ft

  514 Fundamental Way, Cottage Grove, WI 53527

  Discover refined living in this beautifully designed, light-filled home. The main level impresses w/ 2 distinct living areas, offering flexibility & style, along with a private office thoughtfully tucked just off the kitchen. The open-concept floor plan showcases a seamless transition from the mudroom into the chef-inspired kitchen & inviting living areas—perfect for effortless everyday living &

  Husky Homes Team Compass Real Estate Wisconsin

  514 Fundamental Way, Cottage Grove, WI 53527
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  /23

  $315,000

  • Land
  • 5,227 Sq Ft
  • $2,625,000 per Acre

  3606 Atwood Ave, Monona, WI 53714

  Enjoy the beautiful views of Lake Monona and the downtown Madison skyline! Olbrich Park is across the street and the Olbrich gardens are a couple of blocks away! This property is a vacant lot with a garden shed. Property is on the bus route and the bike trail is right in front of the property. Build your dream home with a dream view and enjoy all the amenities that this Atwood neighborhood has to

  Jean Adler Restaino & Associates

  3606 Atwood Ave, Monona, WI 53714
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  /11

  $574,900

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,927 Sq Ft

  4736 Romaine 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

  4736 Romaine Rd, Fitchburg, WI 53711
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  /2

  $189,000

  • Land
  • 15,246 Sq Ft
  • $540,000 per Acre

  2008 Wellington Place, Cottage Grove, WI 53527

  Beautiful walkout lot with Eastern backyard exposure. Located in the highly desirable Westlawn Estates neighborhood. Building permit available now.

  Andrew Homburg Homburg Realty Inc

  2008 Wellington Place, Cottage Grove, WI 53527
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  /36

  $515,000

  • 2 Beds
  • 1.5 Baths
  • 1,341 Sq Ft

  1037 Williamson St Unit 302, Madison, WI 53703

  If you're looking for a sun-drenched condo in a phenomenal location, this one is for you! Vaulted ceilings, skylights, and large windows create an open & airy living space. The floor plan is the best of both worlds: Open, yet plenty of room seating, bookshelves, and art. The large primary suite has beautiful arched windows & ample closet space. The second bedroom/den, while non-conforming, offers

  Andrea Bolan Relish Realty

  1037 Williamson St Unit 302, Madison, WI 53703
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  /84

  $2,975,000

  • 5 Beds
  • 4.5 Baths
  • 6,514 Sq Ft

  4338 Mcconnell St, Fitchburg, WI 53711

  On a rare 100-foot mature lot along the shores of Lake Waubesa, this exceptional residence blends intentional design with casually elegant living. Thoughtfully crafted to capture sun exposure throughout the day, the home showcases timeless architecture, high-end finishes, and exceptional craftsmanship, creating a setting that feels both refined and welcoming. Inside and out, the home is designed

  Louisa Enz Collective Real Estate Group

  4338 Mcconnell St, Fitchburg, WI 53711
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  /4

  $550,800

  New Construction

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

  The Emerald Plan at Pheasant Crossing, Middleton, WI 53562

  Ideal for gatherings, gadgets and relaxation. The Emerald offers smart features that cater to your every need. Congregate with family around the kitchen island, dock your devices at the Daily Station and re-charge yourself in its impressive Owner’s Suite. All prices, promotions and specifications are subject to change at any time without notice based on the discretion of Veridian Homes.

  Veridian Homes Builder

  6801 S Towne Dr Unit 39464875, Middleton, WI 53562
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  /3

  $1,600,000

  • Land
  • 16.5 Acres
  • $96,970 per Acre

  3058 County Highway Bb -, Cottage Grove, WI 53718

  Located immediately east of the City of Madison, Great Visibility to Cottage Grove Road. Land is planned to be annexed to the City of Madison upon development. Potential location for a Residential, Retail, Hospitality or Office development, upon municipal approvals. Layout for land division is flexible per Seller.

  Dan Scardino Point Real Estate

  3058 County Highway Bb -, Cottage Grove, WI 53718
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  /2

  $165,000

  • Land
  • 12,196 Sq Ft
  • $589,286 per Acre

  2995 Wellington Place, Cottage Grove, WI 53527

  Gorgeous interior lot w mature trees and open space behind it. Partial rear exposure of 3-4' available. Fully served lot in the growing community of Cottage Grove in a lovely, highly desirable neighborhood.

  Andrew Homburg Homburg Realty Inc

  2995 Wellington Place, Cottage Grove, WI 53527
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  /21

  $529,900

  New Construction $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,663 Sq Ft

  5817 Bridle Way, Madison, WI 53718

  New Construction - Ready in June! Discover the perfect blend of comfort and convenience with this new ranch-style construction home in the desirable Jannah Village Subdivision in Madison. Enjoy the spaciousness of a split ranch coupled with the practicality of a 3-car garage. Inside, be greeted by the elegance of Cathedral ceilings and ample countertop and cabinet space. A luxurious Master

  Ryan Prellwitz Loos Custom Homes

  5817 Bridle Way, Madison, WI 53718
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  /102

  $617,500

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,446 Sq Ft

  The Atwood Plan at Rosewood Fields, McFarland, WI 53558

  Here’s a home centered on being the life of the party. The Atwood’s sophisticated curb appeal will immediately draw in your guests. Stash coats away in the foyer closet. Keep everyone in the conversation, while seated around the angled kitchen island. And you know that dining bump-out is going to come in handy for dinner parties. Just make sure you’ve stocked the walk-in pantry with the good

  Veridian Homes Builder

  6437 Tuscobia Trail Unit 40337563, McFarland, WI 53558
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  /4

  $112,900

  • Land
  • 4,791 Sq Ft
  • $1,026,364 per Acre

  4787 Brassica 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

  4787 Brassica Rd, Fitchburg, WI 53711
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  /23

  $265,000

  $4K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,098 Sq Ft

  704 Herndon Dr Unit 201, Madison, WI 53718

  Beautifully maintained top-floor unit at Alta Green! Featuring two spacious bedrooms, two full baths, and filled with natural light. Enjoy the many amenities the association has to offer, such as underground heated parking, a dedicated storage unit, and a well-designed layout that maximizes comfort and functionality. The perfect balance of quiet and convenience, being near the Door Creek

  Sam Jessup Pinnacle Real Estate Group LLC

  704 Herndon Dr Unit 201, Madison, WI 53718
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  /4

  $112,900

  • Land
  • 4,791 Sq Ft
  • $1,026,364 per Acre

  4786 Brassica 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

  4786 Brassica Rd, Fitchburg, WI 53711
• 

  

  /3

  $112,900

  • Land
  • 4,791 Sq Ft
  • $1,026,364 per Acre

  4791 Brassica 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

  4791 Brassica Rd, Fitchburg, WI 53711
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  /43

  $424,000

  $36K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,860 Sq Ft

  5911 E Open Meadow, Mc Farland, WI 53558

  Bright, spacious 3 bed, 2.5 bath half-duplex in sought-after McFarland, tucked on a quiet cul-de-sac and backing to a scenic pond and bike path. The inviting living room features soaring vaulted ceilings and abundant natural light. Enjoy a large eat-in kitchen with breakfast bar—perfect for everyday living or entertaining. Convenient main-floor laundry just off the garage entry. Upstairs you will

  Melissa Dix United Country Midwest Lifesty

  5911 E Open Meadow, Mc Farland, WI 53558
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  /34

  $345,000

  $20K PRICE INCREASE

  • 3 Beds
  • 2.5 Baths
  • 1,536 Sq Ft

  5501 Prairie Place Dr, McFarland, WI 53558

  Nestled in McFarland's Prairie Place community with easy access to Madison, this end-unit townhome looks out over open green space, a pond, and walking trails. No parking lot in sight, just landscape. The open layout flows naturally from a kitchen with an island and stainless appliances into a living area warmed by a gas fireplace. The primary bedroom comes with its own ensuite, and stylish

  Dan Chin Homes Team Real Broker LLC

  5501 Prairie Place Dr, McFarland, WI 53558
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  /27

  $895,000

  $55K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 2,720 Sq Ft

  135 S Brittingham Place, Madison, WI 53715

  Timeless charm meets modern sophistication in this beautifully updated home just steps from downtown, yet tucked away from the downtown bustle. Enjoy sweeping views of Monona Bay and Brittingham Park from nearly every room, creating a stunning natural backdrop year-round. Originally built in 1916, the home was thoughtfully renovated in recent years and expanded to include an additional 700 square

  Steve Gilbertson Building Equity Development

  135 S Brittingham Place, Madison, WI 53715
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  /4

  $112,900

  • Land
  • 4,791 Sq Ft
  • $1,026,364 per Acre

  4783 Sorrel Dr, 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

  4783 Sorrel Dr, Fitchburg, WI 53711
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  /33

  $335,000

  • 1 Bed
  • 1 Bath
  • 720 Sq Ft

  360 W Washington Ave Unit 712, Madison, WI 53703

  Set in a coveted downtown location just steps from dining, shopping, entertainment, and the Capitol corridor, this thoughtfully designed one-bedroom condo pairs city convenience with refined comfort. A well-designed layout creates a polished, move-in-ready interior, while the spacious private patio extends the living space outdoors. The bath includes a jacuzzi tub for a more relaxed daily

  Lori Schilling Sprinkman Real Estate

  360 W Washington Ave Unit 712, Madison, WI 53703
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  /3

  $112,900

  • Land
  • 4,791 Sq Ft
  • $1,026,364 per Acre

  4788 Brassica 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

  4788 Brassica Rd, Fitchburg, WI 53711
• 

  

  /19

  $524,900

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,482 Sq Ft

  1812 August Moon Dr, Madison, WI 53718

  Image is representative of home; colors may vary. All prices, promotions and specifications are subject to change at any time without notice based on the discretion of Veridian Homes.

  Veridian Homes Builder

  1812 August Moon Dr, Madison, WI 53718
• 

  

  /4

  $112,900

  • Land
  • 5,227 Sq Ft
  • $940,833 per Acre

  4793 Brassica 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

  4793 Brassica Rd, Fitchburg, WI 53711
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  /13

  $2,100,000

  $200K PRICE DROP

  • 3,007 Sq Ft

  820 E Dayton St Unit 1, Madison, WI 53703

  Rare 4-parcel, 7-unit portfolio in Madison’s core Isthmus - the city’s most walkable, in-demand location. Combines true neighborhood feel w/immediate access to downtown, restaurants, grocery, entertainment, parks, major employers & the Capitol 8 blocks away. Includes 820, 822, 824 & 828 E Dayton St. Compelling opportunity for investors seeking current income+upside, multifamily developers

  William Butcher Conrad Development LLC

  820 E Dayton St Unit 1, Madison, WI 53703
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  /36

  $559,000

  $20K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,191 Sq Ft

  615 W Main St Unit 207, Madison, WI 53703

  With a price reduction of over $10k and also the seller offering a 2 year UHP Home Warranty... Well to say we are offering a fantastic deal is an understatement. Come see this beautiful Downtown Condo. Fantastic opportunity to enjoy downtown Madison living in this modern and spacious 2-bedroom, 2-bath condo ideally located near the University of Wisconsin campus, State Street, and The Kohl

  Brian Huegel Restaino & Associates

  615 W Main St Unit 207, Madison, WI 53703
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  /2

  $500,100

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,516 Sq Ft

  The Olivia Plan at Autumn Lake - Village, Madison, WI 53718

  Say hello to easy living. Open, airy, and thoughtfully designed on one level, The Olivia makes everyday life feel beautifully uncomplicated. Get lost preparing your favorite recipe in the kitchen, curl up with a good book in the great room, then retreat to the serenity of your private primary suite. From quiet mornings to restful evenings, The Olivia is designed to bring comfort, balance, and

  Veridian Homes Builder

  1803 Autumn Lake Pkwy Unit 36465814, Madison, WI 53718
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  /52

  $1,295,000

  • 2 Beds
  • 2 Baths
  • 1,694 Sq Ft

  211 S Henry St Unit 603, Madison, WI 53703

  Experience elevated downtown living in this stunning modern luxury condominium overlooking Lake Monona and the iconic Wisconsin State Capitol. Designed with sophistication and comfort in mind, this exceptional residence features soaring 10-foot ceilings, dramatic floor-to-ceiling windows, serene sleeping porch perfectly positioned to capture breathtaking lake views and evening sunsets. A rare

  Maria Antoinette Cannarella Restaino & Associates

  211 S Henry St Unit 603, Madison, WI 53703
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  /59

  $419,900

  • 3 Beds
  • 2 Baths
  • 1,756 Sq Ft

  3033 Artesian Ln, Madison, WI 53713

  Nature, trails, and everyday comfort come together in this inviting Madison ranch. Welcome home to this well-maintained 3-bedroom, 2-bath ranch tucked away on a quiet cul-de-sac. Real oak floors, vaulted ceilings, & a gas fireplace create warmth & character throughout the main living area. The kitchen features a breakfast bar and center island for everyday living and entertaining. The updated

  Matt Kornstedt Stark Company, REALTORS

  3033 Artesian Ln, Madison, WI 53713
• 

  

  /16

  $639,900

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,446 Sq Ft

  1816 August Moon Dr, Madison, WI 53718

  Front door will be yellow to match side window panels. All prices, promotions and specifications are subject to change at any time without notice based on the discretion of Veridian Homes.

  Veridian Homes Builder

  1816 August Moon Dr, Madison, WI 53718
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  /32

  $1,670,000

  • 5,544 Sq Ft

  120 N Franklin St, Madison, WI 53703

  120-122 N Franklin St is a rare opportunity to own a high-performing 3-flat investment property with an incredible 14 bedrooms in one of Madison’s most desirable rental locations. Currently generating over $13,500/month in income with potential to exceed $14,500/month, this property offers immediate cash flow and strong upside potential. Located steps from James Madison Park, tenants love the

  Imani Jones EXIT Realty HGM

  120 N Franklin St, Madison, WI 53703
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  /52

  $676,000

  • 2,550 Sq Ft

  2027 E Washington Ave, Madison, WI 53704

  Fully remodeled 4 unit just minutes from the Capitol Square. Building includes one 2 bed, one 1 bed and two studios. Ample dedicated parking in back. Published rents include utility and pet fees. Unit 1 - $1,925 thru 7-31-26, Unit 2 - vacant most recent rent $1,100, Unit 3 - $1,645 thru 5-31-27, Unit 4 - $1,355 thru 5-31-27. On site coin operated laundry & landlord currently pays all utilities.

  Ryan Schmitz The Hub Realty

  2027 E Washington Ave, Madison, WI 53704
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  /42

  $549,900

  $10K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,238 Sq Ft

  409 Coyle Pkwy, Cottage Grove, WI 53527

  Charming & move-in ready 3 bedroom / 2.5 bathroom with only ONE owner. Enter inside to find the vaulted living room w/ cozy stone surrounded gas fireplace & eat-in kitchen w/ all stainless appliances, breakfast bar, pantry, & dining area w/ walkout to patio. Solid-core doors throughout. All 3 beds on the main level include the primary bedroom with walk-in closet equipped with built-in shelving &

  Erin Flesch MHB Real Estate

  409 Coyle Pkwy, Cottage Grove, WI 53527
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  /2

  $194,000

  • Land
  • 15,246 Sq Ft
  • $554,286 per Acre

  2010 Wellington Place, Cottage Grove, WI 53527

  Beautiful walk-out lot with a pond and open space adjacent and Eastern backyard exposure. Located in the highly desirable Westlawn Estates neighborhood. Building permit available now.

  Andrew Homburg Homburg Realty Inc

  2010 Wellington Place, Cottage Grove, WI 53527
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  /8

  $125,000

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

  Lot 5 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

  Lot 5 Wyalusing Dr, Madison, WI 53718
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  /2

  $194,000

  • Land
  • 20,037 Sq Ft
  • $421,739 per Acre

  2986 London Ave, Cottage Grove, WI 53527

  Beautiful wooded walkout lot with a full South backyard exposure. Located in the highly desirable Westlawn neighborhood. Building permit available now. Lot is located on a bump-out cul-de-sac.

  Andrew Homburg Homburg Realty Inc

  2986 London Ave, Cottage Grove, WI 53527
• 

  

  /17

  $250,000

  • Land
  • 4,356 Sq Ft
  • $2,500,000 per Acre

  929 Williamson St, Madison, WI 53703

  Incredible deep lot with tons of possibilities!! Amazing location on eclectic Willy Street! See combined listing with house (928 Jenifer St). Seller prefers to sell both parcels together but will sell separately if house gets accepted offer first. Zoned residential but potential to rezone to commercial (buyer to verify with city of Madison). Owner added footpath from the property line to

  Asher Masino Lauer Realty Group, Inc.

  929 Williamson St, Madison, WI 53703
• 

  

  /34

  $350,000

  • 3 Beds
  • 2.5 Baths
  • 1,653 Sq Ft

  5124 Merwood Ln, Madison, WI 53718

  OFFER-BUMP as of 5/22/26. Stylish end unit condominium townhome in a sought after neighborhood conveniently located between Monona and McFarland. The open layout creates an inviting flow for entertaining and everyday living. Unwind in your private bedroom featuring an expansive walk in closet and ensuite bath with a luxurious walk in shower. Spend cozy winter evenings relaxing by the fireplace.

  Dan Chin Homes Team Real Broker LLC

  5124 Merwood Ln, Madison, WI 53718
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  /35

  $525,000

  $25K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 2,700 Sq Ft

  4484 Beale St, Madison, WI 53711

  No showings until open house Saturday, 5/30/26! Location, location, location! Country living meets lake life, just minutes from everything! Just open the door and head out for a walk, a game of hoops, a bike ride, a swim, some fishing, you name it! A true outdoor lovers paradise. Located just across the street from Lake Waubesa, you will find this nicely updated five bed, two bath, ranch home,

  Jessica Schroeder Berkshire Hathaway HomeServices True Realty

  4484 Beale St, Madison, WI 53711
• 

  

  /13

  $650,000

  • 5 Beds
  • 2 Baths
  • 1,742 Sq Ft

  126 N Franklin St, Madison, WI 53703

  Income properties this close to downtown Madison rarely pencil this well. Just around the corner from James Madison Park, this 5-bed, 2-bath rental is consistently easy to lease thanks to its unbeatable location near campus, downtown restaurants, nightlife, and the lake. Currently rented at $4,295/month with projected rents up to $4,750/month, there’s immediate upside for the next owner. The

  Imani Jones EXIT Realty HGM

  126 N Franklin St, Madison, WI 53703

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