357 properties for sale in First Settlement

Downtown condominium ideally located in the heart of Madison, within walking distance to top-rated restaurants & vibrant entertainment. Enjoy easy access to scenic bike trails along Lake Monona, perfect for outdoor enthusiasts. This light-filled unit features abundant natural light throughout and private balcony with a convenient gas outletâideal for grilling or relaxing while taking in the city atmosphere. This unit offers abundant storage space, including an additional bonus storage unit conveniently located on the second floor. Parking space in heated garage has electric charging station

Welcome to the Festner House! Gorgeous Italianate in the First Settlement District built in 1862 and listed on the Madison Historic Registry. Meticulously maintained and thoughtfully restored. From the dentil moldings and newer Marvin windows on the exterior, to the original flooring throughout the main floor. Large chef's kitchen complete with hickory flooring, stainless appliances as well as ample storage and space to entertain. Formal dining area with a parlor room off to the side featuring a full remodeled bath. Upstairs you will find a blend of original and hickory hardwoods, fully remodeled bath as well as a spacious primary bedroom. While away on your front porch and watch the neighborhood go by with views of Lake Monona. Delight in the parking area that includes 6 Parking Spaces in the back. Perfect for personal use and rent out to neighborhood businesses. All mechanicals, roof, chimneys and insulation replaced within the last few years

Welcome to this fully furnished, stylish top-floor corner condo in Madisonâs sought-after near-East Side! This inviting 1-bedroom, open-format home features elegant vaulted ceilings, large windows, abundant natural light, laminate flooring, and a beautiful double-sided gas fireplace that creates a stunning focal point between the living space and spacious bedroom area. The bright kitchen offers a pantry, generous storage, and breakfast bar that flows seamlessly into the living and dining areas. Large sliding glass doors lead to a private, spacious balcony overlooking mature trees, offering a peaceful retreat and excellent privacy. Enjoy a spacious bathroom, in-unit laundry, additional storage, and 1 assigned space in the heated underground garage, plus storage and bike parking. Pet friendly and conveniently located just steps from Tenney Park, bike paths, Lake Mendota, shops and dining, with easy access to major bus lines and the Capitol

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, thereâs immediate upside for the next owner. The property has been well maintained with mostly vinyl windows, 2 parking spaces plus a moped spot, and very little yard maintenance. Tenants cover all expenses, making this an attractive low-maintenance investment opportunity with strong returns. Also available as part of the 120â126 N Franklin portfolio, offering a rare opportunity to acquire a side-by-side 27-bedroom investment property with significant long-term upside and future redevelopment potential

Timeless 1924 Craftsman beautifully blends historic character with exceptional modern updates just two blocks from Tenney Park and only one mile to the Capitol. This stunning 5-bedroom home features gorgeous original woodwork, hardwood floors, glass transom windows, and a cozy gas fireplace. The chef's kitchen is equipped with quartz countertops, a GE Cafà Series range, Bosch refrigerator, and thoughtful design for everyday living and entertaining. Enjoy movie nights in the home theater, then step outside to your private backyard retreat with terraced landscaping, patio, fire pit, new hot tub, and detached 2-car garage. Every update has been tastefully completed while preserving the home's original charm, creating the perfect balance of craftsmanship, comfort, and an unbeatable isthmus location. Brand new roof and recently painted exterior!

First time on the market in 30 years! Great investment opportunity in popular Madison location. 3 total units, (2) two bedroom/ 1 bath units and (1) one bedroom/ 1 bath unit. Detached garage currently used for storage, huge backyard. Unit 2 & 3 are currently being left vacant for possible owner occupied purchase

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 lakefront. Whether you're looking to expand your investment portfolio or own a prime income-producing property in one of Madison's most desirable neighborhoods, this is an exceptional opportunity you won't want to miss

One-of-a-kind downtown Madison penthouse w/breathtaking panoramic views of the Capitol, Lake Mendota & Lake Monona. The grand foyer features marble floors, crown molding, Italian sconces & a lighted ceiling. Floor-to-ceiling windows highlight the spacious living room, while the dining room offers a lighted tray ceiling, balcony access & a fireplace. The well-appointed kitchen includes a generous butlerâs pantry w/ additional appliances & storage. The private primary suite features a gas fireplace, Lake Mendota-facing balcony, two walk-in closets & spa-like bath. Two versatile dens provide exceptional additional living space, including one w/ a fireplace & private bath that could easily serve as a second bedroom or guest suite. Ideally located w/in walking distance of downtown restaurants, shops & entertainment, this exceptional condominium is filled w/ natural light. Abundant storage, 5 fireplaces, 2 parking stalls & a private storage unit complete this truly unique downtown residence

Rare opportunity to own a 4-unit investment property in Madison's highly desirable Mansion Hill neighborhood. Excellent location near the Capitol, UW-Madison campus, State Street and downtown amenities. Property features a desirable unit mix consisting of one 3-bedroom, one 2-bedroom and two 1-bedroom apartments, plus a 2-car garage and 2 additional surface parking spaces. Proforma gross annual income of $81,422 with leases in place through August 14, 2027. Historic 1882 property features hardwood floors and ornate woodwork along with recent improvements including exterior painting (2026), new furnace (2025), EPDM roof and railing above garage (2024), partial roof shingle replacements and coin-operated dryer. Legacy property held by current ownership for 18 years

Experience downtown Madison living at its finest! This stunning end-unit condo offers breathtaking rooftop terrace views of the Capitol and Lake Mendota, where spectacular sunrises and sunsets create an unforgettable backdrop year-round. Located just steps from James Madison Park, State Street, the Capitol Square, and Madison's best dining, shopping, and entertainment, the location simply can't be beat. Inside, the thoughtfully designed floor plan blends comfort and sophistication with abundant natural light, treetop views, and exceptional privacy. High-end finishes and premium windows enhance every space, while multiple living areas and generous storage make everyday living effortless. This second-floor walk-up includes a private 5' x 8' storage unit and boasts an incredible Walk Score of 96, putting the very best of Madison right outside your door

Stylish 2-bed, 2-bath condo with a versatile den at Metropolitan Place! This light-filled unit offers hard surface counters, stainless steel appliances, and low-maintenance flooring throughout. Enjoy built-in bookshelves in the living area and custom built-ins in the second bedroom. The spacious primary suite features tile flooring and a single sink, while a deep pantry off the dining area adds valuable storage. Step out to a large private balcony for fresh air, city views, and beautiful sunsets. Ultimate convenience with an exercise room, parking, and storage all on the same floor. Relax or entertain at the rooftop garden with gazebo and grills. Just blocks from the Capitol, library, restaurants, nightlife, and museums

Penthouse #1001 at one of downtown Madisonâs most sought-after condominium residences. This fully renovated unit captures sweeping lake views and the Capitol skyline along a prized downtown setting. Walls of glass draw the water into the living and dining areas, kitchen, and bedrooms, creating a bright, ever-changing backdrop. Two private verandas extend the living space outdoors, a rare offering in the downtown condo market, while a generous in-unit laundry, two parking spaces, and a dedicated storage unit adds uncommon functionality. Enjoy an elevated lifestyle with immediate access to the energy of downtown dining, events, and the lakefront path. Two parking spaces and a storage unit are included in the sale

1904 Dutch Colonial in Madisonâs historic Vilas neighborhood. Set in a quiet residential pocket known for beautiful historic homes, mature trees, exceptional walkability and easy access to some of Madisonâs best-loved destinations. This 3-bedroom home offers a wonderful opportunity to thoughtfully restore and update a piece of Madison history while making it your own, with renovation loan options available to help bring your vision to life. Original details include natural woodwork, built-ins, oak hardwood floors beneath the carpeting on the main level and maple floors upstairs. Enjoy the large screened front porch, spacious yard and walk-up attic with potential for future finished living space. Driveway access from Madison St, alley access and room to add a garage offer flexibility. Just one block from Monroe St, with easy access to Vilas Park, the zoo, Lake Wingra, Wingra Beach, the Arboretum, UWâMadison, bike paths, bus service, shops and restaurants!

Lakefront living on Monona Bay takes center stage at this fully remodeled and meticulously maintained home with 40 feet of frontage, a private dock and captivating Capitol views. Inside, warm hardwood floors and a stunning stone fireplace bring character to the inviting living spaces, while the layout is designed to make the most of its exceptional setting. The main level opens naturally to a deck for outdoor dining and lakefront relaxation, while an extra-large second-floor screen porch extends the living space into the open air. The entire upper level is dedicated to a private primary suite, complete with a walk-in closet and en suite bath, creating a peaceful retreat above it all. Thoughtful updates provide peace of mind, including a new roof (2023), furnace (2023), air conditioner (2024) and more. Just minutes from downtown Madison, this is a rare opportunity to enjoy direct access to the water with the city skyline and Capitol as your backdrop

New roof, furnace, ac & dishwasher summer of 2026! Set in the remarkable Vilas neighborhood, this four-bedroom home places Camp Randall, Henry Vilas Zoo, and Trader Joe's within easy reach. Inside, nine-foot ceilings and hardwood floors create timeless appeal, while a sunlit sunroom off the kitchen invites slow mornings. A formal dining room adds elegance, and the finished attic offers flexible space for your plans. Step out to a deck overlooking lovely gardens, with an oversized two-car garage nearby. Extra paving means football Saturday parking income. Schedule your showing today!

Well-built home used as a 2-flat for many years. (See MLS #2032-). Great potential for converting to an owner occupied residence Newer refinished wood floors on main level. Large welcoming covered front porch, double entry with original front door. Formal dining room on main formerly used as primary BR. New roof and gutter guards ('26). Newer vinyl windows and siding, newer boiler. Large 3-season porch with many windows on upper, as well as large kitchen on upper which could be converted to a 4th BR. New toilet and flooring in upper bath ('22). Sewer lateral and concrete replacement on driveway apron and sidewalk. Great location near Tenney Park, buses, schools, shopping. Ultimate UHP Warranty. (Room names and locations can vary if converted to an owner occupied residence). Currently vacant and ready for some updates. Purchase for a rental or as owner occupied. New 50-gallon water heater installed 9/24/26

Fresh Opportunity. New market adjustment offers exceptional buy! Stunning classical w/endless upgrades & amenities. Seller's travels to Europe, especially Italy & Greece, inspired his design of the classic elements of the home. I define it as a masterpiece; unique & truly one of a kind! Enjoy 3 levels of living. MAIN: Laundry, Half Bath, Office, DR is open to the $350k Kitchen Remodel w/high end appls & large Island, beautiful gardens & lake views from the Sitting Area & Great Rm. SECOND: Mother-In-Law Suite w/Kitchenette, private Bath & Balcony, 2 add'l bdrms & full ba-the tile & design will amaze you. THIRD: THE Primary Suite w/skylights, Kitchenette, fplace, luscious full ba w/Jacuzzi, lg 2 person steam shower w/multiple shower heads, sitting area & private balcony to enjoy lake views. LL-Small intimate sitting area. Work Shop. Add'l parking spaces in driveway, closer to the house. A creation of love that took 49 years to perfect! Pre-Listing Inspection. UHP Ultimate Home Warranty

Live in the heart of downtown Madison, just three blocks from Capitol Square. Rarely available, 2-bedroom, 2-bath residences with two parking stalls at Capitol West seldom come to market, making this a unique opportunity to enjoy one of the city's most sought-after condominium communities. Thoughtfully appointed interiors pair warm oak flooring and cabinetry with granite countertops, and Kohler fixtures throughout. The kitchen is both stylish and functional, featuring a gas range, vent hood, and GE Profile stainless steel appliances. The primary bath is designed for comfort with a double vanity and a walk-in shower. Tandem parking and a storage unit provide added convenience, while Capitol West amenities include an on-site manager, fitness center, and business center. A polished urban retreat in one of Madison's most walkable neighborhoods

A+ location for this campus investment property! This two-flat is in the heart of downtown Madison. It has two apartments, each with 4 bedrooms and 1 bath and a huge back parking lot. The tenants pay their own electricity and there is substantial income from the separately leased parking spots. 5,615 in rent, $80 in laundry income, and $405 in parking yields a gross annual income of $73,200. This is a solid investment in prime real estate

Excellent investment opportunity near UWâMadison campus! This 5-bedroom, 2-bath home offers a strong rental setup with convenient access to campus, amenities, and everything Madison has to offer. Recent updates include new LVP flooring and all new windows in 2023, a new furnace in 2025, AC updated in 2019 and water heater in 2026. The property is currently leased through 8/14/27 at $3,250/month, providing an established rental arrangement for the next owner. 2-3 parking spaces available for use as well! A great opportunity to add a well-located, updated property to your investment portfolio!

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 existing circular flow, amazing storage (6'x4' walk-in pantry, wall of cabinets in laundry, lots of built-ins), & peace-of-mind updates. All allowing you to get creative for your own living needs. Conveniently located underground parking spot w/personal EV charger & room to hang bikes, plus a separate storage unit for the'extras'. You will LOVE your new downtown Madison way of life in a warm community. Enjoy lobby movie nights with your neighbors, as well as countless restaurants, shops, Overture, Farmer's Market. All right outside your door. Welcome home!

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 your favorite beverage after a long day or go to the roof top patio and take in the sights in front of a fire or cook out on one of the grills. The courtyard is another private area to stroll or sit and soak up the sun. There is a storage room down the hall from this unit plus you have 2 parking spaces. Now is the time to start living your best life without the hassles of the up keep of a home

Two flat in great near-west location is an amazing opportunity for an owner-occupant or add to your income property portfolio. Upper unit currently being held vacant, but could be quickly filled in this high demand neighborhood. Just a block from St. Mary's or the Arboretum; a few blocks from the zoo, Monona Bay, Meriter, Park Street eating and entertainment locations; quick bike to campus or the Square. Features include hardwood floors, formal dining, yard space for gardening or possibly a future garage, individual laundry hookups. First showing only Unit 2. Unit 1 has a slightly smaller living room (because of hallway placement), otherwise identical layout. Property in an Estate; no RECR and limited income/expense history available

Garden-style condo living in the heart of downtown Madison, just a few blocks from the Capitol! This top-floor, one-bedroom, one-bath home offers an inviting open floor plan, abundant natural light, and beautiful park views. The kitchen features stainless steel appliances, oversized island, and plenty of room for entertaining. Spacious primary bedroom with a full bath, featuring a double vanity. Enjoy a private deck and convenient in-unit laundry. Resort-style amenities include a large community room, roof top terrace, gym, and sauna, while one covered and heated parking space is located on the same level as the unit for added convenience. Ideally situated within walking distance of Madisonâs best restaurants, shops, grocery stores, parks, and everything downtown has to offer

Beautifully maintained home in the heart of Tenney-Lapham awaits a new owner! This lovingly cared for 3 bed/1.5 bath home blends original character with thoughtful updates throughout. Hardwood floors flow through the home, while the updated kitchen with breakfast bar opens nicely to the dining room. The freshly renovated four season sunroom provides a bright, inviting space to relax year round. Outside, the massive 2-car garage is a rare find, with a finished studio above featuring updated electrical, heating, and views over the home and yard. This detached studio is perfect for an office, creative space, or hangout. New roof and gutters ('26), H2O heater ('26), and other updates provide added peace of mind. Close to Tenney Park, Lake Mendota, schools, the bustling E Johnson corridor, and everything downtown Madison has to offer. A truly special home in one of Madison's most sought after neighborhoods!

An exceptional opportunity in downtown Madison, WI, this 3-unit, 9-bedroom is the closest house on Mifflin to campus with great southern light, full front decks, and rear exit decks. Each unit in this turn-key property is leased thru 08/2027 and offers a spacious and practical layout, including a full kitchen, three bedrooms, one bathroom, and a comfortable living area. Tenants appreciate the updated basement with storage and laundry. Additional income is generated through four on-site parking spaces. Tenants are responsible for electricity, garbage/recycling, cleaning, and snow removal. With gross income of $108,900 for 2026/2027 and several rents below market, a new buyer has the potential to earn an even greater return on their investment through future lease adjustments. Cap rate of 8.36% per seller

Steps from the Capitol Square, State St, Overture Center & all your favorite Madison hangouts â this downtown condo puts you right in the middle of the action, with a peaceful retreat to come home to. You get 2 secure parking spaces PLUS a storage unit, all on the same level as your unit â no hauling groceries up stairs! Freshly painted with brand-new bedroom carpet, this place feels like'yours' from day one. The kitchen is a showstopper: sleek SS appliances, barstool seating & updated hardware make it perfect for entertaining. A floor-to-ceiling balcony door floods the living space with natural light, while the smart layout keeps the bedrooms private with roomy closets to spare. In-unit laundry=everyday ease, and a brand-new AC means you're set for summer. When you're not out soaking up Madison, unwind in the outdoor courtyard or get a workout in at the exercise room â year-round perks, right at home. Come see it for yourself!

Ultra-rare opportunity to purchase five contiguous parcels on the 500 block of West Mifflin and West Dayton Streets! Each of these five parcels has a multi-unit property earning solid rents and large back parking lots for additional income. The four Mifflin properties make a rectangle of approximately 130 x 120 feet. The abutting Dayton Street parcel makes this a unique opportunity for redevelopment with driveway access to both streets. Most of the parcels have 4 parking stalls and that income is not included in the rent data above. This is a once-in-a-generation opportunity to get this much land in a top-tier campus housing location. 535 W Dayton rent is $5,615 and has 7 bedrooms. Five parcels: 534 W Mifflin St. 070923124-, 536 W Mifflin St. 070923124-, 538 W Mifflin St. 070923124-, 540 W Mifflin St. 070923124-, 535 W Dayton St. 070923124

Great downtown 3-unit in an unbeatable location! New roof in 2025, newer furnace and updated electrical which are separately metered. Just blocks from the Capitol Square, James Madison Park & Kohl Center. Residents will love the inviting front porches ideal for entertaining, with easy access to downtown dining, shopping, entertainment, and the lakefront. Fully rented until August of 2027. This is a wonderful opportunity for investors to add to their portfolio or new investors just getting started to own in a wonderful neighborhood

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 Madisonâs 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 oversized units, available parking, outdoor porches, and classic charm that make these apartments exceptionally easy to rent year after year. The property has been well maintained, including a newer boiler installation, making it an attractive option for investors seeking stability and long-term appreciation. Large unit sizes, premium location, and strong rental demand make this a truly rare Madison investment opportunity. The property is also being offered as part of the 120-126 N Franklin st portfolio. A rare side-by-side 27 bedroom opportunity with significant development potential