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6671 S Chickahauk Trl, Middleton
$789,000
4 Beds ⋅ 4 Baths ⋅ 2034086 MLS ⋅ ACTIVE Status
Wake up to some of the most spectacular views in Middleton. Overlooking the Pheasant Branch Conservancy, this stand-alone condo offers a rare blend of privacy, comfort, and connection to nature. Expansive windows fill the home with natural light while showcasing beautiful views year-round. Warm oak floors welcome you into the open-concept main level, where a spacious living room with a gas fireplace flows into the dining area and kitchen. Designed for everyday living and entertaining, the kitchen features a center island with seating, and a walk-in pantry. Meticulously maintained and move-in ready, the home offers multiple living spaces. The bright walk-out family room opens to a private patio, while the spacious primary suite features abundant natural light, a large walk-in closet, soaking tub, and separate walk-in shower. Enjoy low-maintenance condo living, near parks, trails, schools, shopping, and dining in one of Middleton's most scenic settings.

6671 S Chickahauk Trl, Middleton
6230 Middleton Springs Dr Unit 6230, Middleton
$284,000
2 Beds ⋅ 2 Baths ⋅ 2033394 MLS ⋅ ACTIVE Status
Open floor plan lit by the sun at several angles. Upper level 2 bedroom, 2 bath with private deck. Great location with easy access to shopping. Private garage and laundry. Middleton schools.

6230 Middleton Springs Dr Unit 6230, Middleton
7237 Lily Ln, Middleton
$899,900
3 Beds ⋅ 3 Baths ⋅ 2033288 MLS ⋅ ACTIVE UNDER CONTRACT Status
Step into easy, upscale condo living with exceptional attention to detail throughout. The main level features a showstopping quartz island and backsplash, upgraded cabinetry, KitchenAid stainless appliances, cooktop and hood vent, and an open layout connecting the kitchen, dining and living areas. Wide arches, hardwood floors and thoughtful finishes add timeless appeal. The primary suite offers a private bath with quartz vanity, tiled shower with bench and a walk-in closet with built-ins. A flexible office/2nd bedroom, full bath and convenient laundry room with washer/dryer and folding counter complete the main level. Enjoy a maintenance-free deck overlooking Graber Pond and Conservancy/walking path. The finished lower level adds a 3rd bedroom with built-ins, full bath, game room w/wet bar, rec room with fireplace and game area, plus a dedicated office/wine display room with cellar. A rare combination of style, space and functionality; just a short walk to Pheasant Branch Conservancy!

7237 Lily Ln, Middleton
2051 Allen Blvd Unit 401, Middleton
$254,900
2 Beds ⋅ 1 Baths ⋅ 2033126 MLS ⋅ ACTIVE Status
Great location in the Middleton-Cross Plains School District and just minutes from downtown Madison! This well-maintained, 2 bedroom, Condo features a gourmet kitchen with cherry cabinets, granite countertops, tile backsplash & stainless steel appliances. Convenient in-unit washer/dryer. Enjoy the spacious balcony with beautiful views of Lake Mendota and Marshall Park. Walk to Lakeview Park with splash pad, tennis courts, and baseball fields. A wonderful combination of location, convenience and views!

2051 Allen Blvd Unit 401, Middleton
5019 Prairie Rose Ct, Middleton
$724,000
3 Beds ⋅ 3 Baths ⋅ 2033044 MLS ⋅ ACTIVE Status
SPECTACULAR RANCH STYLE CONDO IN DESIRABLE BISHOPS BAY NEIGHBORHOOD. One level living (primary bedroom, laundry, deck all on main floor). Located on a cul-de-sac for extra privacy. New roof September 2026. Andersen windows. Main level with cathedral ceiling, many large windows, maple wood flooring and a solar tube give this area an abundance of sunlight. LIVING ROOM (gas fireplace w/ tile surround, patio doors to maintenance free deck, decorative ceiling fan, built in cabinetry), KITCHEN (Island, breakfast bar, gas cook top, SS appliances, solid surface countertops, spectacular cabinetry, tile backsplash), DINING AREA (room for large table), PRIMARY BEDROOM (new LVP flooring, ceiling fan, walk-in closet, ensuite bathroom w/ double sinks, soaking tub, walk-in shower), LAUNDRY ROOM (washer, dryer included, tile floor), POWDER ROOM (guest bathroom). The Lower Level w/ new LVP flooring; BEDROOM #2 and BEDROOM #3. FULL BATHROOM (cabinetry). REC ROOM (access to patio) Large storage room.

5019 Prairie Rose Ct, Middleton
3550 Valley Ridge Rd, Middleton
$385,000
3 Beds ⋅ 2 Baths ⋅ 2032423 MLS ⋅ ACTIVE Status
Welcome to Orchid Heights Townhomes! Close to beautiful Lake Mendota, walking trails and the scenic 682 acres of Pheasant Branch Conservancy. Enjoy low-maintenance living with lawn care and snow removal included, community pool and picnic area. This beautifully updated townhome features a completely renovated kitchen, updated bathrooms, updated flooring and new carpet on the upper level. Spacious kitchen offers plentiful cabinetry, granite counters, formal dining area flows into the inviting living room. Step out to a private patio to relax and enjoy amazing views and breathtaking sunsets. Upstairs are three spacious bedrooms with ample closet space. The finished lower level includes, a large rec room, a freestanding shower, and plenty of storage. An oversized one-car garage, guest parking across from the unit, and an unbeatable location make this move-in-ready home one you won’t want to miss! New Roof and Gutters September 2026, New Garage doors being installed in October.

3550 Valley Ridge Rd, Middleton
2814 Pleasant View Rd Unit 202, Middleton
$250,000
2 Beds ⋅ 1 Baths ⋅ 2031873 MLS ⋅ ACTIVE UNDER CONTRACT Status
Enjoy easy condo living in a fantastic Middleton location! This bright and spacious 2nd-floor unit sits directly across from Firefighter’s Memorial Park and features abundant natural light and an open-concept layout perfect for everyday living and entertaining. Step outside to your private balcony for morning coffee or a relaxing evening outdoors. Both bedrooms offer generous space, including a walk-in closet in the primary. Additional conveniences include in-unit laundry, a private garage, and an extra-large storage unit. Located in the sought-after Middleton-Cross Plains School District with quick access to parks, shopping, schools, dining, and the Beltline. Professionally managed condo association with pets and rentals allowed. A great opportunity to enjoy space, convenience, and a prime Middleton location!

2814 Pleasant View Rd Unit 202, Middleton
2004 Butler Ct, Middleton
$599,999
3 Beds ⋅ 3 Baths ⋅ 2031089 MLS ⋅ ACTIVE Status
PRICE REDUCED! Assumable 5.7% FHA Mortgage rate with qualification! Welcome to 2004 Butler Court, a beautifully appointed, free-standing condo tucked away on a quiet Middleton cul-de-sac. This light-filled home offers 3 bedrooms, 2.5 baths and a fabulously low condo fee. The open main level features hardwood floors, a gas fireplace, patio access and a flexible office or den. The spacious kitchen boasts granite countertops, an island, abundant cabinetry and an oversized walk-in pantry. The main-level primary suite includes a walk-in closet and tiled walk-in shower. The exposed lower level adds a second living area, 2 bedrooms and a full bath—ideal for guests or recreation. Additional highlights include paneled doors, custom blinds, ample storage and a new roof installed 8/26 all just minutes from downtown Middleton, Lake Mendota, Pheasant Branch Conservancy, shopping, restaurants, UW–Madison and UW Hospital. Measurements are approximate; buyer to verify.

2004 Butler Ct, Middleton
6404 Maywood Ave, Middleton
$324,500
3 Beds ⋅ 2 Baths ⋅ 2030173 MLS ⋅ ACTIVE UNDER CONTRACT Status
Invest in your future and build equity with this 3-bedroom, 2-bath half-duplex in the heart of highly desirable Middleton! This inviting home features an updated & stylish kitchen, two separate living areas affording plenty of room to spread out, split bedrooms for home office or guest space, and an attached garage. Take advantage of yard space and an outstanding location within walking distance off Pheasant Branch Conservancy, schools, parks, Lake Mendota, restaurants, and more! This home combines space, convenience, opportunity, and an exceptional location - welcome home!

6404 Maywood Ave, Middleton
9110 Waterside St, Middleton
$525,000
4 Beds ⋅ 3 Baths ⋅ 2029928 MLS ⋅ ACTIVE Status
This four-bedroom luxury ranch features a spacious open floor plan with plenty of natural light. The great room features cathedral ceilings, skylights, a fireplace with a wood mantel, and sliding patio doors leading to a fully enclosed three-season room. The kitchen comes fully equipped with all appliances, a pantry, and a built-in desk. The primary suite offers vaulted ceilings, two closets, and a private bath with a double-sink vanity. Downstairs, the finished exposed lower level includes a second family room, two additional bedrooms, and a full bath.

9110 Waterside St, Middleton
5021 Prairie Rose Ct, Middleton
$724,900
3 Beds ⋅ 3 Baths ⋅ 2029323 MLS ⋅ ACTIVE Status
Spacious, updated ranch-style condo in Bishop's Bay with a main-level primary suite and a new roof. The open-concept kitchen and living room feature bamboo flooring and a gas fireplace, while the eat-in kitchen offers solid surface counters, a gas range with hood vent, and abundant storage. Step outside to the private, covered composite deck — perfect for grilling or fresh air. The large primary suite impresses with custom built-ins, a walk-in shower, jetted tub, and an oversized walk-in closet. Downstairs, brand-new carpet runs throughout the expansive walk-out living space, complete with a second gas fireplace and a concrete patio. Two additional bedrooms, a full bath, and a private office round out the lower level. Recent updates include a new furnace, A/C, and water heater ('23) and new lower-level flooring('26). Topping it all off is a rare, oversized 4 car garage — plenty of room for cars, boats, and all your toys. There's simply too much to list — schedule your showing

5021 Prairie Rose Ct, Middleton
707 Cricket Ln Unit 5, Middleton
$325,000
2 Beds ⋅ 3 Baths ⋅ 2027562 MLS ⋅ ACTIVE Status
Move right into this end-unit condo in the highly sought-after Middleton School District! Ideally located just minutes from Blackhawk Park, West Towne Mall, and the Beltline, this home offers the perfect blend of comfort and convenience. The open-concept main level features a spacious living room with a cozy gas fireplace, dining area, and kitchen complete with stainless steel appliances. Upstairs, you'll find two generously sized bedrooms, each with its own private en-suite bathroom, plus conveniently located second-floor laundry. Step outside to the Trex deck, perfect for grilling or relaxing on warm summer evenings. Complete with a 2-car attached garage and low-maintenance condo living, this home is ready for you to enjoy!

707 Cricket Ln Unit 5, Middleton
2051 Allen Blvd Unit 201, Middleton
$249,000
2 Beds ⋅ 1 Baths ⋅ 2027352 MLS ⋅ ACTIVE Status
Conveniently located near shopping, restaurants, and the bus line, this beautifully updated end-unit condo offers comfort, convenience, and investment potential. Featuring 2 bedrooms, 1 full bath, an open layout, in-unit washer and dryer, and a spacious private balcony, this home is move-in ready. Enjoy the convenience of heated underground parking with one assigned space, elevator access, and secure building amenities. Currently operating as a successful short-term rental, this property offers rental income potential through the remainder of the year. The established short-term rental business and all furnishings are available for purchase separately, providing a turnkey investment opportunity or a fully furnished personal retreat. Don't miss this versatile property in an exceptional location!

2051 Allen Blvd Unit 201, Middleton
7305 Donna Dr, Middleton
$379,500
2 Beds ⋅ 2 Baths ⋅ 2026790 MLS ⋅ ACTIVE Status
NEW ROOF 10/26. Enjoy Vibrant Living in this sunny & spacious 2BR/1.5BA plus Lofted den/office Condo. Loft is perfect for working from home or a welcoming guest space. Easy Condo living in desirable Woodridge Condo Community w/ vaulted ceilings, 2 stories of windows, beautiful wood floors, skylights, gas fireplace, attached 2 car garage, private entrance & no shared walls. Tranquil back deck with Southern Exposure overlooking Pheasant Branch Conservancy w/ miles of trails to explore. Only 25 minutes to downtown Madison & 20 minutes to Verona, 5 minutes to beltline. 1.3 miles (30 minute walk) to downtown Middleton w/unique shops, restaurants/bars and the Mustard Museum. Several updates and Improvements. Enjoy an open plan ideal for everyday living, Spot local wildllife, enjoy Green Space & Container Gardening on your sunny back deck. Live Inspired, work from home, host friends, move in and make it yours!

7305 Donna Dr, Middleton
2134 Allen Blvd Unit 2, Middleton
$183,000
2 Beds ⋅ 1 Baths ⋅ 2026336 MLS ⋅ ACTIVE Status
Cozy first floor 2bd/1bth garden condo features a easy access to downtown Middleton, beautiful cottonwood filled green space, and a patio view of Lake Mendota! Complex just had all roofs replaced! Condo fee includes heat, water/sewer, and hot water! Affordable and convenient, this cute condo is waiting for you.

2134 Allen Blvd Unit 2, Middleton
6253 Middleton Spring Dr, Middleton
$234,900
1 Beds ⋅ 1 Baths ⋅ 2025815 MLS ⋅ ACTIVE UNDER CONTRACT Status
One-bedroom condo with a hard to find private attached one car garage, outside private patio and private main entrance. (With low condo fees of only $255 a month) This condo is centrally located to restaurant's, Coffee Shop, Fitness center, Hardware Store, Pheasant Branch Trail, and Lake Mendota. This end unit condo offers an open floor plan with the kitchen, living room, dining area all overlooking the private patio. nice size bedroom with a large closet, and in unit Washer and dryer. Included in the sale all the appliances- refrigerator, dishwasher, washer, dryer and window coverings. All stated room measurements are estimated, if important to buyer, buyer is to verify.

6253 Middleton Spring Dr, Middleton
5548 Century Ave Unit 4, Middleton
$215,000
2 Beds ⋅ 2 Baths ⋅ 2022646 MLS ⋅ ACTIVE Status
Conveniently located in Middleton’s desirable Rolling Hills Condo Association, this bright & welcoming 2-bed, 2-bath condo offers a true escape from the daily grind. Sunlight streams into the spacious open-concept living area, which opens onto a private balcony overlooking rolling green lawns, mature trees, & the community pool. The well-designed galley kitchen provides ample cabinetry, counter space & room for friends & family to gather while you cook. The primary suite features a private ensuite bath, generous walk-in closet & peaceful views. A second bedroom, additional full bath, in-unit laundry & 2-car tandem garage complete the thoughtful layout. Residents enjoy exclusive access to the sparkling pool, scenic walking trails, BBQ & picnic areas & the serene surroundings of the Rolling Hills community. Ready to move in & enjoy effortless living & a strong sense of community in one of Middleton’s most convenient associations.

5548 Century Ave Unit 4, Middleton
5522 Century Ave Unit 3, Middleton
$215,000
2 Beds ⋅ 2 Baths ⋅ 2020669 MLS ⋅ ACTIVE UNDER CONTRACT Status
This 2-bed, 2-bath condo offers the perfect quiet park-like setting nestled near the Pheasant Branch Conservancy. This Garden style unit features plank flooring, a bright open concept with a private balcony overlooking the pool and gardens. The kitchen features natural wood cabinets, a brand new refigerator & Microwave, a dedicated dining space as well as a smaller breakfast area. The primary suite includes an updated ensuite bath, walk-in closet and additional closet. The second bedroom has 2 closets, main full bath is updated with a tile tub surround and granite countertops, in-unit laundry and 1-car garage with storage unit. Enjoy the beautiful pool or take a walk on the trails or use the BBQ area. Enjoy this wonderful location to shops, and restaurants, Mendota County Park!

5522 Century Ave Unit 3, Middleton
2140 Allen Blvd Unit 3, Middleton
$189,900
2 Beds ⋅ 1 Baths ⋅ 2020794 MLS ⋅ ACTIVE Status
Welcome to this beautifully updated 2-bedroom, 1-bath condo in an unbeatable Middleton location. The refreshed kitchen features quartz countertops, white cabinetry and stainless steel appliances, flowing seamlessly into a bright and comfortable living space. Enjoy a quiet, private setting from your balcony that feels like you’re nestled in the trees, perfect for morning coffee or evening unwinding. Ideally located directly across the street from Marshall Park on the shores of Lake Mendota, offering easy access to trails, green space and waterfront activities. Additional highlights include a private 1-car garage, ample surface parking for residents and guests and a dedicated storage unit. HOA dues cover heat and hot water, adding convenience and value to this exceptional opportunity.

2140 Allen Blvd Unit 3, Middleton
2142 Allen Blvd Unit 4, Middleton
$179,900
2 Beds ⋅ 1 Baths ⋅ 2017985 MLS ⋅ ACTIVE Status
This 2-bedroom condo offers a recently updated kitchen, comfortable living spaces, and a fantastic location just minutes from Madison. This condo is conveniently located across from Marshall Park! A bus stop right outside the building to take you directly into downtown Madison. Inside, you will find a bright and functional layout designed for everyday ease. Additional highlights include a private 1-car garage, ample surface parking, a separate storage unit, and a balcony overlooking the peaceful wooded green space. New roof installed in 2026. The condo HOA includes heat, water, sewer, and snow and garbage removal. A convenient card/coin-operated laundry machine is located in the basement. Well-located, affordable, and move-in ready.

2142 Allen Blvd Unit 4, Middleton
4303 Goldeneye Gateway Dr, Middleton
$469,480
3 Beds ⋅ 3 Baths ⋅ 2017812 MLS ⋅ ACTIVE Status
Welcome to Canna Lily Cottages at Redtail Ridge-featuring Middleton Schools! Kitchen features granite countertops & sink, large island, tile backsplash, stainless appliances & pantry. Primary bedroom suite features walk-in closet & private bath with tile shower & dual sinks. Main floor laundry & powder room. Built-in wood cubbies in rear foyer. 2-car attached garage w/ extra storage! 10yr builder's limited warranty & 15yr dry basement warranty included! Condo fee includes private road, driveway & sidewalk snow removal, lawn care, liability insurance, officer & director coverage, and third party manager. Radon mitigation system is passive. Interior staged photos are of a similar model.

4303 Goldeneye Gateway Dr, Middleton
4307 Goldeneye Gateway Dr, Middleton
$473,360
3 Beds ⋅ 3 Baths ⋅ 2017809 MLS ⋅ ACTIVE Status
Welcome to Canna Lily Cottages at Redtail Ridge--featuring Middleton Schools! Open concept home features great room with fireplace & additional flex area. Kitchen includes quartz countertops, large island, granite sink, stainless appliances & pantry. Primary bedroom suite features walk-in closet and private bath with dual sinks. 2-car attached garage with extra storage! 10yr builder's limited warranty & 15yr dry basement warranty included! Condo fee includes private road, driveway & sidewalk snow removal, lawn care, liability insurance, officer & director coverage, and third party manager. Radon mitigation system is passive.

4307 Goldeneye Gateway Dr, Middleton
4317 Goldeneye Gateway Dr, Middleton
$471,323
3 Beds ⋅ 3 Baths ⋅ 2017808 MLS ⋅ ACTIVE Status
Welcome to Canna Lily Cottages at Redtail Ridge--featuring Middleton Schools! Kitchen includes quartz countertops, large island, granite sink, stainless appliances, and pantry. Primary bedroom suite features walk-in closet and private bath with tile shower & dual sinks. Main floor laundry & powder rooms. Built-in wood cubbies in rear foyer. 2-car attached garage with extra storage! 10yr builder's limited warranty & 15yr dry basement warranty included! Condo fee includes private road, driveway & sidewalk snow removal, lawn care, liability insurance, officer & director coverage, and third party manager. Radon mitigation system is passive.

4317 Goldeneye Gateway Dr, Middleton
9395 Old Sauk Rd, Middleton
$459,900
3 Beds ⋅ 3 Baths ⋅ 2015879 MLS ⋅ ACTIVE Status
Elegance and style are showcased in the lovely 3 bed, 2 1/2 bath end unit townhouse condo in the Middleton School District! Beautifully appointed with soaring ceilings, dramatic windows, clean architectural lines and open concept. Thoughtfully designed kitchen with white cabinets, quartz counters, kitchen island/breakfast bar, tile backsplash, stainless appliances and separate dining space. Gleaming wood floors and gas fireplace enhance the warmth of the main level great room. Primary suite with tray ceiling, en suite full bath with double sinks and walk in closet. Two additional sunny bedrooms, another full bath and in unit laundry complete the upper level. Updated lighting, paint and carpet throughout. 2-car attached garage. The perfect combination of design, quality and location!

9395 Old Sauk Rd, Middleton

This information, provided by seller, listing broker, and other parties, may not have been verified. Copyright 2026 South Central Wisconsin MLS Corporation. All rights reserved. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify perspective properties consumers may be interested in purchasing.