Homes for Sale near Milestone Democratic School

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  /70

  $450,000

  • 4 Beds
  • 3 Baths
  • 2,138 Sq Ft

  5 Waywood Cir, Madison, WI 53704

  Welcome to your new home! This spacious, updated 4-bedroom, 3-bathroom home features a 2-car garage, not one but TWO living rooms and a spacious yard that's perfect for relaxing, entertaining, or room for pets to play. The private primary room includes its own en-suite bathroom, creating the perfect retreat at the end of the day. Best of all, this home is move-in ready and waiting for its new

  Kevin Navarro LPT Realty

  5 Waywood Cir, Madison, WI 53704
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  /25

  $249,900

  • 2 Beds
  • 1.5 Baths
  • 1,422 Sq Ft

  902 N Thompson Dr Unit 2, Madison, WI 53704

  Nice 2 bedroom townhome style condo w/great location & easy access in every direction! You'll be just minutes away from the East Towne Mall area for shopping, dining, fitness, and more. Located near trails and easy access to public transit as well. On the main floor, you'll find the kitchen, combined living/dining area with walk-out to your private deck and a powder room. Upstairs you'll find 2

  Steven Schuster RE/MAX Preferred

  902 N Thompson Dr Unit 2, Madison, WI 53704
• 

  Price To Be Determined

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,248 Sq Ft

  The Delafield Plan at Jannah Village, Madison, WI 53718

  The Delafield offers a spacious and versatile layout, perfect for families of all sizes. With 4 bedrooms and 2.5 baths, this 2248 square foot home provides ample living space. Choose from two elegant elevations, featuring optional stone or brick accents, to customize the exterior to your taste.

  Loos Homes Builder

  5805 Bridle Way Unit 39356287, Madison, WI 53718
• 

  Price To Be Determined

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,700 Sq Ft

  The Pilot Home (30 Rosewood Fields) Plan at Rosewood Fields, McFarland, WI 53558

  This thoughtfully crafted pilot home was brought to life by The Veridian Homes Architecture and Design Team to explore new ideas in layout, functionality, and design. Created as a place to introduce and refine innovative features, it allows our team to thoughtfully evaluate how new concepts come together in a real-world setting before they’re incorporated into the Veridian Homes plan portfolio.

  Veridian Homes Builder

  6437 Tuscobia Trail Unit 40971251, McFarland, WI 53558
• 

  Price To Be Determined

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,880 Sq Ft

  The Tennyson Plan at Jannah Village, Madison, WI 53718

  Loos Homes Builder

  5805 Bridle Way Unit 39356299, Madison, WI 53718
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  /72

  $599,900

  • 4 Beds
  • 4 Baths
  • 2,669 Sq Ft

  4727 Catalina Pkwy, Mc Farland, WI 53558

  OPEN SATURDAY 9/5 11:00-1:00! Modern 2669 sqft 2 story McFarland Home! This 4 bdrm, 2full/2half bath home offers class & modern sought after features throughout! Beautiful great rm w/fireplace & custom built-in accented by a big beautiful window flooding the entire area w/natural sunlight! Wide open floor plan draws in the beautiful quartz kitchen featuring new backsplash in 2025, dovetailed soft

  Peggy Acker-Farber RE/MAX Preferred

  4727 Catalina Pkwy, Mc Farland, WI 53558
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  /72

  $1,195,000

  $100K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 4,199 Sq Ft

  2012 Paris Ln, Cottage Grove, WI 53527

  Exceptional custom ranch offering nearly 2,400 sq ft on the main level plus an exposed walkout lower level, enhanced by nearly $200,000 in high-end upgrades. Designed for both everyday living and entertaining, the chef’s kitchen showcases Amish-built cabinetry, quartz waterfall countertops, marble backsplash, Kohler fixtures, a spacious island, and a walk-in pantry with added cabinetry and prep

  Amber Huemmer Capital Edge Realty

  2012 Paris Ln, Cottage Grove, WI 53527
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  /34

  $403,400

  New Construction $3K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,435 Sq Ft

  4834 Suelo Rd, Fitchburg, WI 53711

  Under construction; estimated completion 10/1/26. Welcome to Terravessa! New duplex townhomes featuring all the comforts of home! Main level open concept living includes great room with gas fireplace. Kitchen features granite countertops, stainless steel appliances, and pantry. Main floor powder room and rear foyer includes large walk-in storage closet and bonus bench & coat rail for easy

  Cari Wuebben Encore Real Estate Services, I

  4834 Suelo Rd, Fitchburg, WI 53711
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  /63

  $749,900

  • 5 Beds
  • 3 Baths
  • 4,717 Sq Ft

  308 Southing Grange, Cottage Grove, WI 53527

  Exceptional 5 bedroom plus office, 3 bath custom ranch in Cottage Grove! Offering 4,717 sq. ft. of finished living space on a private .80 acre lot with large yard and perennial garden backing onto creek. The main level features a formal living room, a family room, primary bedroom and two additional bedrooms. The lower level boasts a 420 sq. ft. dance floor, rec room, two more bedrooms and plenty

  Caleb Payne Madcityhomes.Com

  308 Southing Grange, Cottage Grove, WI 53527
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  /30

  $260,000

  Open Sat 12PM - 2PM

  • 1 Bed
  • 1 Bath
  • 737 Sq Ft

  334 Amoth Ct Unit D, Madison, WI 53704

  Open floor plan condo with a large deck that sits behind mature pine trees and looks over the Capitol City Trail. Walk-in closet & laundry off the bedroom. Deeded parking spot. 100+ sq ft large private storage in basement. Recent serious capital improvements include -- new roof for entire association. Inside the unit is new HVAC (forced air) -- less than 1 year old. Ecobee Smart Thermostat

  Caleb Payne Madcityhomes.Com

  334 Amoth Ct Unit D, Madison, WI 53704
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  /65

  $520,400

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,675 Sq Ft

  4817 Suelo Rd, Fitchburg, WI 53711

  Welcome to Terravessa! Single-level, ranch style living made easy! Enjoy the spacious great room with large windows & gas fireplace. Kitchen features quartz countertops, granite sink, ceramic tile backsplash, stainless steel appliances, and walk-in pantry. Primary bedroom suite includes walk-in closet and private bath with tile shower & dual sinks. Main floor laundry/mud room off garage and large

  Encore Homes, Inc Builder

  4817 Suelo Rd, Fitchburg, WI 53711
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  /16

  $469,900

  $30K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,700 Sq Ft

  5000 Felland Rd, Madison, WI 53718

  Convenient access to amenities, dining, and recreation -Bedroom, 2.5-Bath Home with Secluded Privacy and Convenient Location Enjoy the best of both worlds in this beautifully situated 3-bedroom, 2.5-bath home. Tucked away in a private, peaceful setting, this property offers a hidden retreat. Just 5 minutes to Madison, Sun Prairie, and Cottage Grove, A rare opportunity to enjoy country-like

  Tiffany Esau Metro Brokers/Duane Reed

  5000 Felland Rd, Madison, WI 53718
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  /24

  $529,900

  New Construction $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,849 Sq Ft

  4401 Crested Owl Ln, Madison, WI 53718

  Custom built open concept ranch home in Madison! This sunny home has 3 bedrooms, 2 baths and an office. The main level features a contemporary living room / kitchen layout with a huge kitchen island. The primary bedroom has an en-suite bath with tile shower and big walk-in closet. Also on the main floor are two more bedrooms and another full bath with bathtub, and an office/den. The lower level

  Caleb Payne Madcityhomes.Com

  4401 Crested Owl Ln, Madison, WI 53718
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  /26

  $949,900

  $150K PRICE DROP

  • 4,320 Sq Ft

  1002 Severson Dr, Madison, WI 53718

  This spacious, well-maintained duplex on Madison’s East Side offers a fantastic opportunity for investors and/or homeowners! Each side features 4 bedrooms and 3 full bathrooms, including a private en-suite with double vanities and walk-in closets in the main bedrooms. The open-concept living and dining areas provide ample space, while a second living room in the lower level adds flexibility. Both

  Jason Berning Realty Executives Cooper Spransy

  1002 Severson Dr, Madison, WI 53718
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  /35

  $322,500

  • 2 Beds
  • 1 Bath
  • 722 Sq Ft

  333 W Mifflin St Unit 2050, Madison, WI 53703

  Experience urban living at Metropolitan Place! This sought-after second-floor condo is a true original, offered by the first owners who hand-picked this unit for its ideal layout and placement when the development was built. Featuring two distinct bedrooms, it provides a versatile, functional space perfect for guests, roommates, or a home office. The floor plan is exceptionally convenient, with

  Greg Stroupe Real Broker LLC

  333 W Mifflin St Unit 2050, Madison, WI 53703
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  /27

  $395,000

  • 1 Bed
  • 1 Bath
  • 1,017 Sq Ft

  309 W Washington Ave Unit 412, Madison, WI 53703

  Downtown living at its finest. This condo places you just one block from Concerts on the Square and the Dane County Farmers' Market, and a 5-minute walk to the UW campus. Expansive windows bring natural light into the open great room, anchored by a gas fireplace. The kitchen offers ample counter space and a large breakfast bar. One of the largest one-bedroom floor plans in Capitol West, this unit

  Amaya Boman Compass Real Estate Wisconsin

  309 W Washington Ave Unit 412, Madison, WI 53703
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  /39

  $330,000

  • 2 Beds
  • 1.5 Baths
  • 1,204 Sq Ft

  3810 E Washington Ave, Madison, WI 53704

  Welcome home to 3810 E. Washington Ave! This well-maintained property offers a perfect blend of character, comfort, and convenience. Inside, you'll find bright, inviting living spaces filled with natural light, a functional layout, and plenty of room to make it your own. Whether you're a first-time buyer, looking to downsize, or searching for an investment opportunity, this home checks all the

  Josh Page Sprinkman Real Estate

  3810 E Washington Ave, Madison, WI 53704
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  /33

  $680,000

  $30K PRICE DROP

  • 3,192 Sq Ft

  14 N Franklin St, Madison, WI 53703

  Classic downtown 3-unit in an unbeatable location! New roof. Just blocks from the Capitol Square and James Madison Park, this well-maintained property offers the perfect combination of historic charm and investment potential. Residents will love the inviting front and back decks, ideal for relaxing or entertaining, while enjoying easy access to downtown dining, shopping, entertainment, and the

  Jeffrey Cullen Weichert, Realtors- Lakepoint

  14 N Franklin St, Madison, WI 53703
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  /42

  $345,000

  • 2 Beds
  • 2 Baths
  • 1,485 Sq Ft

  100 Femrite Dr Unit 106, Monona, WI 53716

  Welcome to this inviting first-floor end-unit condo in a convenient Monona location! Enjoy peaceful views of the community gazebo and greenspace from the tiled, screened-in porch—perfect for relaxing or entertaining. The open kitchen and dining area features durable laminate flooring, a newer refrigerator, and plenty of natural light. Ceiling fans throughout add comfort and airflow. The spacious

  Alison Kane Stark Company, REALTORS

  100 Femrite Dr Unit 106, Monona, WI 53716
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  /47

  $458,000

  $9K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,068 Sq Ft

  4807 Monona Dr, Monona, WI 53716

  Fall in love with the timeless charm of this beautifully preserved 1930s Craftsman, where character and comfort blend effortlessly. Sunlight pours through updated windows, highlighting the gleaming refinished hardwood floors and the cozy bay window that invites you to slow down with your morning coffee. The thoughtfully remodeled kitchen and updated baths offer modern convenience while honoring

  Andy Kramer Redfin Corporation

  4807 Monona Dr, Monona, WI 53716
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  /2

  $180,000

  • Land
  • 14,374 Sq Ft
  • $545,455 per Acre

  2992 Wellington Place, Cottage Grove, WI 53527

  Beautiful full walk-out with Southwesterly facing backyard. Located in the highly desirable Westlawn Estates neighborhood. Building permit available now.

  Andrew Homburg Homburg Realty Inc

  2992 Wellington Place, Cottage Grove, WI 53527
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  /29

  $344,900

  $55K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 1,001 Sq Ft

  1150 Williamson St Unit 204, Madison, WI 53703

  Priced $45,000 below the 2025 appraised value! Stylish 1 BR Condo immersed in one of Madison's most iconic neighborhoods! Soaring ceilings & gorgeous maple hardwood floors create an open, airy vibe. Large windows fill the expansive living area w/ natural light, perfect for relaxing or entertaining. Double-sided fireplace, sleek modern kitchen w/ granite countertops & updated appliances. Spacious

  Joshua Pelletter Rockwood Realty Group

  1150 Williamson St Unit 204, Madison, WI 53703
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  /23

  $309,000

  $10K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,595 Sq Ft

  1813 Conservation Place, Madison, WI 53713

  From the moment you enter, you’ll be welcomed by an abundance of natural light pouring in through oversized windows on all three levels. Enjoy not one, but TWO patio spaces - perfect for morning coffee or evening cocktails. With three bedrooms plus a bonus office, there’s plenty of room to live, work, and entertain. Recent updates include a dishwasher and washer and dryer. A private garage, wood

  Kaitlin Solomon MHB Real Estate

  1813 Conservation Place, Madison, WI 53713
• 

  Price To Be Determined

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,240 Sq Ft

  The Lyndon Plan at Jannah Village, Madison, WI 53718

  The Lyndon offers a spacious and thoughtfully designed layout, perfect for families or those who love to entertain. With 3 bedrooms and 2.5 baths, this floor plan provides ample space for comfortable living.

  Loos Homes Builder

  5805 Bridle Way Unit 39356045, Madison, WI 53718
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  /28

  $347,500

  Open Fri 4:30PM - 6PM $2K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,372 Sq Ft

  203 Wyalusing Dr, Madison, WI 53718

  Meticulously maintained & updated, this alluring 2-story townhouse is conveniently located on Madison’s Eastside. This exceptional walk-up impresses w/ lofty ceilings, elegant hardwood floors & brilliant natural light. Enjoy great conversations in the spacious living room, or cozy up for movie night in front of the gas fireplace at night. Dazzle dinner guests in the modern kitchen w/ a sizable

  Kaitlin Solomon MHB Real Estate

  203 Wyalusing Dr, Madison, WI 53718
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  /46

  $660,000

  • 2,676 Sq Ft

  5802 Sauk Ln, Mc Farland, WI 53558

  Outstanding investment opportunity in the highly desirable McFarland School District! This fully remodeled duplex backs directly to Woodland Estates Park, offering an attractive combination of location, quality, and long-term appeal. Ideal for investors looking to grow their portfolio or owner-occupants seeking the benefits of rental income. For added flexibility, each side is also available for

  Erin Bickelhaupt Realty Executives Capital City

  5802 Sauk Ln, Mc Farland, WI 53558
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  /26

  $613,900

  New Construction $10K PRICE DROP

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

  515 Fundamental Way, Cottage Grove, WI 53527

  Welcome to this charming two-story farmhouse-style home in Cottage Grove, ideally located near schools. A large covered front porch offers the perfect spot to relax. Inside, this thoughtfully designed home features 3 bedrooms and 2.5 bathrooms, blending classic style with modern comfort. The spacious primary suite boasts soaring cathedral ceilings, a generous walk-in closet, and a private ensuite

  Aeryn Barry Tim O'Brien Homes LLC

  515 Fundamental Way, Cottage Grove, WI 53527
• 

  Price To Be Determined

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,741 Sq Ft

  The Princeton Plan at Jannah Village, Madison, WI 53718

  Loos Homes Builder

  5805 Bridle Way Unit 39356143, Madison, WI 53718
• 

  

  /10

  $117,900

  • Land
  • 5,227 Sq Ft
  • $982,500 per Acre

  4758 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

  4758 Lacy Rd, Fitchburg, WI 53711
• 

  

  /13

  $2,249,000

  • 4 Beds
  • 2.5 Baths
  • 3,421 Sq Ft

  2894 Waubesa Ave, Madison, WI 53711

  Set along 105' of Lake Waubesa shoreline, this east facing, lake-level property pairs expansive water frontage with a thoughtful, flexible layout designed for both everyday living and lake life. The lower level has full exposure, bringing natural light into the finished living spaces, while two separate living rooms provide room to gather, relax, or spread out. The main-level primary suite adds

  Lori Schilling Sprinkman Real Estate

  2894 Waubesa Ave, Madison, WI 53711
• 

  

  /13

  $614,900

  $15K PRICE DROP

  • 3,000 Sq Ft

  701 Pinecrest Dr, Madison, WI 53714

  FULLY Occupied! Turn-key cash-flow on Madison’s East Side! This all-brick 4-unit building offers immediate rental income and low-maintenance upkeep. All four units are already leased through mid-2027, providing rock-solid stability from day one. Every unit features durable, turnover-friendly hard-surface flooring throughout (no carpet to replace!). Conveniently located near parks, dining, and

  Jessica Janssen Design Realty LLC

  701 Pinecrest Dr, Madison, WI 53714
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  /74

  $539,900

  New Construction $2K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,695 Sq Ft

  4814 Romaine Rd, Fitchburg, WI 53711

  Move-in ready! Welcome to Terravessa! Open concept cottage home features great room with fireplace & additional flex area. Kitchen includes quartz countertops, granite sink, ceramic tile backsplash, stainless steel appliances, and pantry. Owners suite features walk-in closet and private bath with tile shower & dual sinks. Main floor laundry and powder room. Rear foyer includes built-in wood

  Encore Homes, Inc Builder

  4814 Romaine Rd, Fitchburg, WI 53711
• 

  Price To Be Determined

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,748 Sq Ft

  The Benton Plan at Jannah Village, Madison, WI 53718

  Loos Homes Builder

  5805 Bridle Way Unit 39356190, Madison, WI 53718
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  /30

  $595,000

  • 2 Beds
  • 2 Baths
  • 1,716 Sq Ft

  360 W Washington Ave, Madison, WI 53703

  Downtown living is waiting for you. Conveniently located minutes from the capital square. You will enjoy all the envents that happen around the square, the restaurants, shopping and more. Located in a secure building this 2 bedroom 2 bath garden condo offers an open floor plan, in unit laundry, den/office, solid surface kitchen counter, large balcony to relax on enjoying you morning coffee or

  Lorri & Tanya Team Restaino & Associates

  360 W Washington Ave, Madison, WI 53703
• 

  Price To Be Determined

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,604 Sq Ft

  The Baymont Plan at Jannah Village, Madison, WI 53718

  Loos Homes Builder

  5805 Bridle Way Unit 39356009, Madison, WI 53718
• 

  

  /49

  $593,600

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,879 Sq Ft

  The Sawyer Plan at Pheasant Crossing, Middleton, WI 53562

  A home as resourceful as you are. The flex room may be the perfect home office today, but it can easily transform into a creative craft studio tomorrow. The kitchen offers ample space for preparing elegant feasts, and the island is ready for quick morning routines. When it’s time to unwind, retreat to the spacious primary suite, complete with a private bath designed for comfort and calm. Welcome

  Veridian Homes Builder

  6801 S Towne Dr Unit 38928406, Middleton, WI 53562
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  /38

  $595,000

  • 2 Beds
  • 2 Baths
  • 1,716 Sq Ft

  360 W Washington Ave Unit 215, Madison, WI 53703

  Downtown living is waiting for you. Conveniently located minutes from the capital square. You will enjoy all the events that happen around the square, the restaurants, shopping and more. Located in a secure building this 2 bedroom 2 bath garden condo offers an open floor plan, in unit laundry, den/office, solid surface kitchen counter, large balcony to relax on enjoying you morning coffee or your

  Lorri & Tanya Team Restaino & Associates

  360 W Washington Ave Unit 215, Madison, WI 53703
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  /47

  $564,900

  • 1 Bed
  • 1 Bath
  • 1,314 Sq Ft

  123 W Washington Ave Unit 311, Madison, WI 53703

  A home that appeals to full- or part-time residents alike, this is a see-it-to-believe-it pied-a-terre in the iconic Loraine Hotel! One-of-a-kind sunroom AND personal patio off of the spacious living room offer al fresco dining, gardening, & fluid entertaining - all w/the ability to connect to & utilize the community courtyard - you benefit from the best of both worlds! Inside you will enjoy the

  Mary Duff Stark Company, REALTORS

  123 W Washington Ave Unit 311, Madison, WI 53703
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  /2

  $415,500

  • Land
  • 21,780 Sq Ft
  • $831,000 per Acre

  2747 Ski Ln, Madison, WI 53713

  .46 ACRES ON A COMMERCIALLY ZONED LOT, RECENTLY ANNEXED BY CITY OF FITCHBURG, CONTAINS 1 HOUSE, APPROXIMATELY 800 SQ FT, FULL BASEMENT , 1 BR 1 BA. RENTED ON A MO/MO LEASE

  Tom Jacobs Jacobs Cooperage, LLC

  2747 Ski Ln, Madison, WI 53713
• 

  

  /28

  $1,750,000

  • 3 Beds
  • 3 Baths
  • 2,839 Sq Ft

  1610 Waunona Way, Madison, WI 53713

  Set along a remarkable stretch of Lake Monona shoreline, this architecturally significant residence offers a rare blend of historic design, privacy, + breathtaking Capitol views. Designed in 1937 by acclaimed Madison architects Beatty & Strang, the Toby Curtis House is a striking example of International Style architecture inspired by the Bauhaus movement. Positioned at the quiet end of Waunona

  Chas Martin Sprinkman Real Estate

  1610 Waunona Way, Madison, WI 53713

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