Homes for Sale near Milestone Democratic School

• 

  

  

  /25

  $600,000 Open Sat 2PM - 4PM

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft

  129 Dunning St, Madison, WI 53704

  Step into timeless charm w/this beautifully maintained 1925 home, where classic character meets thoughtful modern updates. Nestled on a quiet street, this home offers the perfect blend of historic appeal and today’s conveniences. The refinished hardwood floors showcase the home’s original craftsmanship, adding warmth & elegance thruout. The fully renovated kitchen is a standout feature, complete

  Robin Taylor Restaino & Associates

  129 Dunning St, Madison, WI 53704
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• 

  

  

  /23

  $355,000

  • 1 Bed
  • 1 Bath
  • 945 Sq Ft

  309 W Washington Ave Unit 512, Madison, WI 53703

  Offering the best in modern downtown living in the heart of the city just 3 blocks from the square. Walking distance to farmers mkt, state street restaurants, senior center, Overture, all that! This SW facing unit offers open concept living area with features including maple floors, electric fireplace, in-unit washer/dryer, exceptional kitchen with ample counter space and storage, quartz

  Diana Hause Realty Profiles, LLC

  309 W Washington Ave Unit 512, Madison, WI 53703
• 

  

  

  /34

  $415,000 Open Thu 4PM - 6PM

  • 5 Beds
  • 2.5 Baths
  • 2,350 Sq Ft

  818 Redland Dr, Madison, WI 53714

  Rare opportunity to own a spacious ranch-style home in Madison’s desirable Burke Heights neighborhood, tucked away at the end of a quiet dead-end road. Offering 5 bedrooms and 2.5 bathrooms at this price point, this home delivers exceptional value and flexibility. Inside, you'll find generous living and gathering spaces ideal for entertaining, along with a dedicated office or flex room that could

  Marine Yoo Real Broker LLC

  818 Redland Dr, Madison, WI 53714
• 

  

  

  /16

  $179,000

  • Land
  • 1.03 Acres
  • $173,786 per Acre

  Lot 1 N Star Rd, Cottage Grove, WI 53527

  Photos coming soon. Check out the best available and highest visibility lot in the business park. Zoned commercial. 1.03 acres waiting for your development. Nice level lot that is ready for building. Builder has verified that a 10,000 square foot building will fit on this lot. Convenient location for distribution just east of Madison.

  Paul Addison Stark Company, REALTORS

  Lot 1 N Star Rd, Cottage Grove, WI 53527
• 

  

  

  /57

  $1,800,000

  • 4 Beds
  • 3 Baths
  • 2,778 Sq Ft

  333 W Mifflin St Unit 1251, Madison, WI 53703

  Don’t miss this rare and stunning two-level corner penthouse condo in the heart of Madison. 4 bedrooms, 3 full baths, and almost 2,800 square feet of elegant living space. Courtyard and Lake Monona views from a generous wrap-around deck. Natural stone countertops and backsplash in the contemporary chef’s kitchen with GE Monogram SS appliances. Engineered hardwood floors throughout. Vaulted

  Paul Addison Stark Company, REALTORS

  333 W Mifflin St Unit 1251, Madison, WI 53703
• 

  

  /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
• 

  

  /37

  $349,900

  • 2 Beds
  • 1 Bath
  • 696 Sq Ft

  2513 Moland St, Madison, WI 53704

  Showings begin Wed March 25. Cozy character-filled bungalow in popular Eken Park neighborhood just steps from the Tip Top & Ogden’s. Original hardwood floors throughout, spacious living rm w/ dining area, remodeled kitchen, updated bath & 2 main floor BR’s. Loads of recent upgrades: kitchen (2025), bathroom (2021), roof replaced 2014, updated wiring, outdoor patio (2024), sump pump (2024), water

  Joshua Pelletter Rockwood Realty Group

  2513 Moland St, Madison, WI 53704
• 

  

  /31

  $399,900

  • 1 Bed
  • 1 Bath
  • 1,001 Sq Ft

  1150 Williamson St Unit 204, Madison, WI 53703

  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 bedroom retreat w/ walk-in closet, laundry nook

  Joshua Pelletter Rockwood Realty Group

  1150 Williamson St Unit 204, Madison, WI 53703
• 

  

  /43

  $625,000

  • 1,904 Sq Ft

  5604 Bjelde Ln, Monona, WI 53716

  Monona three unit apartment building offers an opportunity to owner occupy or a solid investment in a growing community! The 1st floor apartment offers three bedrooms, remodeled kitchen w/SS appliances + dishwasher, tile backsplash, new LVP flooring, new a/c unit and remodeled bath (this unit stills needs countertops in kitchen and surround in bathroom to be complete). Unit 2 & 3 have been

  Liz Lauer Lauer Realty Group, Inc.

  5604 Bjelde Ln, Monona, WI 53716
• 

  

  /80

  $415,000

  • 3 Beds
  • 1.5 Baths
  • 1,489 Sq Ft

  5152 Felland Rd, Madison, WI 53718

  Showings begin after the first open house on March 29, 2026 at 1pm. Welcome to this charming 3-bedroom ranch set on a full acre in a highly desirable location between Cottage Grove, Sun Prairie, and Madison. This well-maintained home features hardwood floors and numerous updates throughout, offering both comfort and functionality. Enjoy relaxing or entertaining in the spacious screened-in porch

  Lynette Porior-Arcel First Weber Inc

  5152 Felland Rd, Madison, WI 53718
• 

  

  /14

  $199,900

  • 2 Beds
  • 1 Bath
  • 667 Sq Ft

  3701 Margaret St, Madison, WI 53714

  Walk to Olbrich Park!! Nearly $100,000 below assessment! Home needs a lot of work but has great potential! Located near Olbrich Gardens, Olbrich Park, and all of the popular Atwood restaurants and shops. Great backyard and some updated windows. Home is a pre-approved short sale. Due to condition may need to be a cash sale. No RECR available. Agent has no information of age of mechanicals or any

  Jeff olson RE/MAX Preferred

  3701 Margaret St, Madison, WI 53714
• 

  

  /17

  $519,900

  • 2,520 Sq Ft

  5802 Sauk Ln, Mc Farland, WI 53558

  Vacant and ready for immediate occupancy—set rents at market value. Rare side-by-side duplex in the heart of McFarland with strong rental potential in a walkable location near coffee shops, restaurants, and local amenities. Unit 1 offers 3 bedrooms and 2 bathrooms; Unit 2 features 2 bedrooms and 1.5 bathrooms—ideal for owner-occupants or investors. Both units feature fresh paint and new

  Becca Hamilton RL Realty Group

  5802 Sauk Ln, Mc Farland, WI 53558
• 

  

  /13

  $750,000

  • 2,000 Sq Ft

  1043 Jenifer St, Madison, WI 53703

  1043 Jenifer Street is located in Madison’s highly desirable Willy Street neighborhood. This rental property offers a great investment opportunity featuring 4 spacious units and 8 off-street parking spots. Current rents are well below market. The building has a strong rental history with consistent demand driven by the area’s vibrant mix of local shops, restaurants, parks and walkability. Whether

  Robert Grether Weichert, Realtors- Lakepoint

  1043 Jenifer St, Madison, WI 53703
• 

  

  /20

  $229,000 Open Thu 4:30PM - 6PM

  • 2 Beds
  • 1.5 Baths
  • 1,425 Sq Ft

  4154 Alvarez Ave, Madison, WI 53714

  Showings begin 4.3.26. Townhouse condo framed by lush front and back courtyards, creating a rare sense of privacy and greenery on both sides of the home. A private entrance leads into an updated kitchen and spacious condo. The new bathroom will impress. The eat-in kitchen includes all appliances, a breakfast bar, and ample room for casual dining. Patio doors extend the living area outdoors, while

  Lori Schilling Sprinkman Real Estate

  4154 Alvarez Ave, Madison, WI 53714
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  /4

  $2,300,000

  • 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
• 

  

  /12

  $1,050,000

  • 3,182 Sq Ft

  1054 Williamson St, Madison, WI 53703

  1054 Williamson Street is a mixed-use rental property featuring two residential units and one established restaurant. This property offers immediate stability and strong tenant demand. The below market rents present significant upside for investors seeking value-add potential. Situated on Willy and Ingersol, tenants and patrons enjoy walkable access to popular dining, local shops, parks, and Lake

  Robert Grether Weichert, Realtors- Lakepoint

  1054 Williamson St, Madison, WI 53703
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  /34

  $185,000

  • 2 Beds
  • 1 Bath
  • 852 Sq Ft

  15 Sherman Terrace Unit 1, Madison, WI 53704

  Tenney Park Sherman Terrace first floor condo sits in a great locale at the end of the cul de sac w/greenspace surrounding the unit. The interior is ready for some updates while offering updated low-e windows, laminate wood flooring in living and dining, kitchen was opened to dining and walks out to greenspace with Paw Paw tree that bears fruit in October. Bedrooms have tile floors and spacious

  Liz Lauer Lauer Realty Group, Inc.

  15 Sherman Terrace Unit 1, Madison, WI 53704
• 

  

  /40

  $500,000

  • 2 Beds
  • 1.5 Baths
  • 1,150 Sq Ft

  4512 Larson St, Mc Farland, WI 53558

  Welcome to 4512 Larson Street in McFarland—where lifestyle, location, and opportunity come together. Located less than 200 feet from Lake Waubesa, this home puts you just steps from the water, making it perfect for enjoying all your spring and summer lake activities. Inside, you’ll find a functional open layout, spacious living areas, and a comfortable primary suite. The home also features a

  Jo Ferraro EXP Realty, LLC

  4512 Larson St, Mc Farland, WI 53558
• 

  

  /27

  $1,550,000

  • 3 Beds
  • 2.5 Baths
  • 2,764 Sq Ft

  4911 Tonyawatha Trail, Monona, WI 53716

  Rare Lake Monona home on level lot, designed for comfortable living, offering breathtaking views of Madison's Capitol Skyline and Stunning Sunsets. This charming Lake Home, offers a large, flat entertainment lawn between the home and water. Inside the redesigned floorpan provides true main-level living with kitchen, living, dining, laundry, 3 bdrms and 2 full baths- all on the same level. A third

  Gary Pressentin Pressentin Company LLC

  4911 Tonyawatha Trail, Monona, WI 53716
• 

  

  /23

  $559,000

  • 1 Bed
  • 1.5 Baths
  • 1,038 Sq Ft

  404 S Blount St Unit 303, Madison, WI 53703

  Wake up to sunrise views over Lake Monona in this bright, top-floor condo at the coveted Fauerbach. Perfectly positioned between downtown and the lakefront, this updated home offers a walkable, bike-friendly lifestyle. Open, sun-filled layout with windows framing Lake Monona and the Monona Terrace skyline. The living and dining areas open to a private balcony, ideal for morning coffee or evening

  Seth Pfaehler The McGrady Group, LLC

  404 S Blount St Unit 303, Madison, WI 53703
• 

  

  /34

  $400,000 Open Sat 11AM - 1PM

  • 2 Beds
  • 2.5 Baths
  • 2,342 Sq Ft

  6132 Culpepper Ln, Madison, WI 53718

  Ranch-style half duplex in the desirable Richmond Hills neighborhood! This legally established condominium has no active association or condo fees. Featuring an open-concept layout with vaulted ceilings, a split 2-bedroom design, and 2 full bathrooms on the main level. The updated kitchen offers quartz countertops, stainless steel appliances, and an optional washer/dryer hookup in the pantry. The

  Jo Ferraro EXP Realty, LLC

  6132 Culpepper Ln, Madison, WI 53718
• 

  

  /18

  $1,250,000

  • 3,000 Sq Ft

  1718 Onsgard Rd, Madison, WI 53704

  Conveniently located on Madison's East Side - all apartments in this 8-unit building have been beautifully remodeled! Each unit is two beds and 1 bathroom, with in-unit laundry.

  Danica Rademacher Patriot Properties

  1718 Onsgard Rd, Madison, WI 53704
• 

  

  /30

  $434,900

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

  6136 Ragan St, Madison, WI 53718

  Beautiful, open Ranch home in popular Grandview Commons North offers main floor living at its finest. The 1,653 sq ft layout features 9-ft ceilings, an open kitchen/dining/great room with LVP flooring, Auburn Ridge cabinets, and a center island. A large mud/laundry room comes with washer and dryer included, and the primary suite offers a double vanity full bath and walk-in closet. The attached

  Brian Callahan Madison Abodes LLC

  6136 Ragan St, Madison, WI 53718
• 

  

  /32

  $850,000

  • 2,316 Sq Ft

  508 W Mifflin St, Madison, WI 53703

  Solid two-flat investment property in the heart of campus housing! This classic multi-unit property has a flexible layout and is currently rented as a single house with one lease at $4,570 per month. Two parking spots are currently leased at $135 each per month. The 2026/27 lease is signed for $4,800 per month with one parking spot at $135 per month. Tenants pay their own gas, electrical and

  Caleb Payne Madcityhomes.Com

  508 W Mifflin St, Madison, WI 53703
• 

  

  /5

  $99,900

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft

  65 Rustic Pkwy Unit 129, Madison, WI 53713

  It's not every day you find a home like this at a price like this. Welcome to Highland Manor-a pristine, well-kept community where comfort, value, and curb appeal come together. Now available: a 2022 home with 1232 sq. ft., 3 bedrooms, and 2 bathrooms for just $860.00/month, including site fees. This is the kind of opportunity that doesn't stay on the market long. Schedule your tour today. Staged

  Tori Coil Highland Manor

  65 Rustic Pkwy Unit 129, Madison, WI 53713
• 

  

  /32

  $420,000 Open Sat 11AM - 12:30PM

  • 3 Beds
  • 2.5 Baths
  • 1,615 Sq Ft

  2135 Autumn Lake Pkwy, Madison, WI 53718

  Picture-perfect and move-in ready, this lovely 2 year old Veridian Gramercy model in the highly desirable Autumn Lake neighborhood blends style, comfort, and smart design. The open concept layout is perfect for everyday living and entertaining, featuring a gourmet kitchen with a large island breakfast bar, quartz countertops, custom cabinetry, and stainless steel appliances. The kitchen flows

  Annette Tande Riemer First Weber Inc

  2135 Autumn Lake Pkwy, Madison, WI 53718
• 

  

  /34

  $269,000 Open Sat 10AM - 12PM

  • 2 Beds
  • 1.5 Baths
  • 1,270 Sq Ft

  5334 Lake Park Blvd, Madison, WI 53713

  Beautifully situated just two blocks from Lake Monona, this updated 2-bedroom townhouse offers stylish comfort in a highly walkable location. The bright living room features new wood flooring, while the foyer, kitchen, and bathrooms showcase elegant new tile. Both bathrooms have been thoughtfully renovated with modern finishes, and new light fixtures throughout the home add a fresh, contemporary

  Stacy Ozanne First Weber, Inc

  5334 Lake Park Blvd, Madison, WI 53713
• 

  

  /28

  $499,900

  • 3 Beds
  • 2 Baths
  • 2,082 Sq Ft

  4174 Brian St, Mc Farland, WI 53558

  Step inside this beautiful McFarland home that blends comfort and versatility. A bright living room with fireplace flows into spacious dining and kitchen areas for easy connection. The large family room with wet bar and storage is perfect for entertaining or relaxing. Upstairs, find three bedrooms, offering flexibility for rest, work, or guests. Enjoy the deck overlooking your spacious yard and

  Dan Chin Homes Team Real Broker LLC

  4174 Brian St, Mc Farland, WI 53558
• 

  

  /32

  $535,000

  • 4 Beds
  • 3 Baths
  • 2,151 Sq Ft

  5915 Running Deer Trail, Mc Farland, WI 53558

  Showings start 3/5. Highly functional floor plan & fresh, modern updates throughout! The main living area welcomes you with newly refinished hardwood floors & soaring vaulted ceilings, creating a bright open feel anchored by a floor-to-ceiling stone gas FP. Stylishly updated bathrooms & a stunning kitchen elevate the home’s appeal, while the finished walk-out LL expands your living options w/

  Hansen Home Team Real Broker LLC

  5915 Running Deer Trail, Mc Farland, WI 53558
• 

  

  /56

  $799,900

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

  517 Buss Rd, Cottage Grove, WI 53527

  VPR: $799,900-839,900. Spacious and versatile, this impressive 5-bedroom, 3.5-bath two-story offers over 4,100 sq ft above grade with an unfinished lower level ready for future expansion, complete with egress window and bath rough-in. The main level features a private primary suite plus a potential second suite upstairs, ideal for multi-generational living. Enjoy soaring 18-ft ceilings and walls

  Amber Huemmer LPT Realty

  517 Buss Rd, Cottage Grove, WI 53527
• 

  

  /16

  $279,900

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft

  2617 Hoard St, Madison, WI 53704

  Well maintained 2 bed, 1 bath home near Eken park. All the heavy lifting has been done: new roof, new furnace, electrical upgrade, new siding , carpeting, walls have been primed awaiting your design choices. Great location, situated right between the vibrant Eastside and the developing Northside. Walkable to restaurants, parks, coffee shops. Easy access to bus line.

  Amy Bua First Weber Inc

  2617 Hoard St, Madison, WI 53704
• 

  

  /22

  $929,900

  • 3 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
• 

  

  /69

  $1,295,000

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

  2012 Paris Ln, Cottage Grove, WI 53527

  Stunning custom ranch with nearly 2,400 sq ft on the main level & an exposed walkout lower level, showcasing nearly $200K in upgrades throughout. Gourmet chef’s kitchen features Amish cabinetry, quartz waterfall countertops, marble backsplash, Kohler fixtures, walk-in pantry with cabinetry & counters, and a large island with breakfast seating. Open dining & living room with coffered ceiling and

  Amber Huemmer LPT Realty

  2012 Paris Ln, Cottage Grove, WI 53527
• 

  

  /19

  $469,000

  • 3 Beds
  • 2 Baths
  • 1,490 Sq Ft

  2175 Autumn Lake Pkwy, Madison, WI 53718

  Welcome to the Village at Autumn Lake, a new and highly desirable east Madison neighborhood! This inviting ranch has a great open-concept layout where the living room flows seamlessly into the kitchen and dining area which is ideal for everyday living and entertaining. The main level features a spacious primary suite with a walk-in closet and ensuite bath. The main level also features 2

  Paul Haviland Stark Company, REALTORS

  2175 Autumn Lake Pkwy, Madison, WI 53718
• 

  

  /59

  $825,000

  • 4 Beds
  • 2.5 Baths
  • 3,785 Sq Ft

  1314 Manassas Trail, Madison, WI 53718

  Stunning, single-owner custom home in desirable Richmond Hill, beautifully situated on a mature lot backing up to rolling fields. New hardwood floors span the main living areas, complementing the formal living room with fireplace, window seat, & crown molding, as well as the formal dining room with crown molding. French doors leading to a private den. The updated kitchen features SS appliances,

  Denise Holmes Collective Real Estate Group

  1314 Manassas Trail, Madison, WI 53718
• 

  

  /23

  $1,100,000

  • 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
• 

  

  /52

  $319,900 Open Thu 2PM - 4PM

  • 3 Beds
  • 1 Bath
  • 783 Sq Ft

  2926 Milwaukee St, Madison, WI 53704

  Charming Updated Bungalow with Modern Comfort & Classic Character! This 3-bed bungalow blends timeless charm with extensive updates. The 1st floor bedroom opens to the living area, while the upstairs walk-through bedroom is perfect for a nursery, office, or large WIC. The kitchen has new cabinets, countertops, sink, and appliances. Major systems include a new furnace & central air (2025) and

  Matt Kornstedt Stark Company, REALTORS

  2926 Milwaukee St, Madison, WI 53704
• 

  

  /19

  $999,900

  • 3,200 Sq Ft

  914 N Oak St, Madison, WI 53704

  Excellent investment opportunity! This six-unit apartment building features spacious 2-bedroom, 1-bathroom units, each designed for comfortable living. With all units currently rented, the property generates over $97,000 in annual income. Well-maintained and ideally located, this income-producing property is perfect for both seasoned investors and those looking to start or expand their portfolio.

  Eric Breidel Investment Realty Services LLC

  914 N Oak St, Madison, WI 53704
• 

  

  /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
• 

  

  /50

  $256,900 Open Thu 5PM - 7PM

  • 2 Beds
  • 2 Baths
  • 1,198 Sq Ft

  101 Metro Terrace Unit 102, Madison, WI 53718

  Imagine a home that finally keeps pace with your lifestyle. This 2-bed, 2-bath retreat trades clutter for clarity, offering a crisp, intentional floor plan where every room serves a purpose. Sunlight anchors the open living area, flowing naturally toward a sleek kitchen and breakfast bar designed for effortless hosting. Slide open the doors to your private garden-side patio, the perfect sanctuary

  Matt Kornstedt Stark Company, REALTORS

  101 Metro Terrace Unit 102, Madison, WI 53718

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