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$2,699,000
6 Beds ⋅ 5.5 Baths
Located in the Town of Middleton with low taxes, on a breathtaking, mature, wooded, and private 1.5-acre lot, this extraordinary custom residence offers the high-end finishes, craftsmanship, quality, artistry, and natural privacy today?s luxury buyers demand. Situated in the desirable Glacier End neighborhood, this one-of-a-kind home showcases real cherry hardwood floors, custom cherry cabinetry, and premium granite throughout. Luxury features include a 4-car garage, 6 bedrooms with en-suite baths, two primary suites, two gourmet kitchens, including a chef?s kitchen with commercial-grade appliances, two laundry rooms, a main-floor office, Pella windows with built-in blinds, central vac, intercom, surround sound, and a Decra Villa Tile roof. The walkout lower level offers a wet bar, steam room, exercise room, theater, fireplace, and access to a lush, tree-lined backyard. Middleton Schools!

3319 Saracen Way, Middleton

Listing courtesy of Bunbury & Assoc, REALTORS.

$399,000
3 Beds ⋅ 1.5 Baths
Opportunity knocks in the Town of Middleton! Located in a convenient pocket subdivision with lower Town taxes, this 3 bedroom, 1 full/1 half bath home offers great bones and tremendous potential. Features include a 2 car garage, large wooded lot, and an exposed lower level ready for future expansion. The home is livable as-is, but buyers will likely want to update and modernize over time. Priced at $399,000, this is a rare chance to build equity in a highly desirable area

7001 W Old Sauk Road, Middleton

Listing courtesy of Building Equity Development.

$399,900
Land this special doesn't stay available for long, and your dream home deserves the perfect setting. This nearly one-acre homesite offers the rare combination of privacy, space, and prestige, with generous separation from neighboring homes that creates a relaxing and entertaining atmosphere. Located in Middleton's Cherrywood Ridge neighborhood within the acclaimed Middleton-Cross Plains Area School District, this homesite places you minutes from premier shopping, parks, golf courses, and major roadways, all while backing to a pond that adds a natural touch of peace to your backyard. Jason Thomas Homes is ready to partner with you to design and build the home you've always envisioned.

Lot 17 Welcome Drive, Middleton

Listing courtesy of Jason Thomas Homes LLC.

$624,900
3 Beds ⋅ 2.5 Baths
Located in the highly sought-after Middleton School District, this stunning 3-bed, 2.5-bath home offers the perfect blend of comfort, space & functionality. Step in from the front porch into a warm & welcoming main level w/ spacious living area anchored by a charming fireplace perfect for relaxing evenings. The open layout flows seamlessly into the kitchen & dining area w/ room to gather. A versatile flex room on the main level provides endless possibilities for a formal dining, office, craft or play room. Upstairs, find a generous primary suite w/ cathedral ceilings, private ensuite bath w/ tiled shower & walk-in closet, plus 2 additional bedrooms and a full bath. An egress window in the lower level allows potential for a future finished basement. Enjoy peaceful suburban living in this Middleton gem! Photos of a similiar model. Move in ready!

6683 Linnet Lane, Middleton

Listing courtesy of Tim O'Brien Homes LLC.

$626,900
3 Beds ⋅ 2.5 Baths
Located in the heart of the highly sought-after Middleton School District, this stunning 3-bedroom, 2.5-bathroom home offers the perfect blend of comfort, space & functionality. Step in from the large covered front porch to a welcoming spacious living area w/ charming fireplace perfect for relaxing evenings. The open layout flows seamlessly into the kitchen w/ ample counter space, walk in pantry & attached dining area with room to gather.. A generous primary suite w/ ensuite bath w/ tiled shower and walk-in closet, plus 2 additional bedrooms each with walk in closets, a full bath and conveniently located second floor laundry round out this thoughtfully laid out home plan. Plenty of space in the 3 car garage. An egress window in the lower level allows potential for a future finished basement. Don't miss out on this Middleton gem! Photos of similar model.

6625 Junco Drive, Middleton

Listing courtesy of Tim O'Brien Homes LLC.

$614,900
3 Beds ⋅ 2.5 Baths
Located in the heart of the highly sought-after Middleton School District, this stunning 3-bedroom, 2.5-bathroom home offers the perfect blend of comfort, space & functionality. Step in from the covered front porch to a welcoming spacious living area w/ charming fireplace perfect for relaxing evenings. The open layout flows seamlessly into the kitchen w/ ample counter space, walk in pantry & attached dining area with room to gather.. A generous primary suite w/ ensuite bath and walk-in closet, plus 2 additional bedrooms each with walk in closets, a full bath and conveniently located second floor laundry round out this thoughtfully laid out home plan. Plenty of space in the 3 car garage. An egress window in the lower level allows potential for a future finished basement. Don't miss out on this Middleton gem! Photos of similar model. Move in ready!

6671 Linnet Lane, Middleton

Listing courtesy of Tim O'Brien Homes LLC.

$215,000
2 Beds ⋅ 2 Baths
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 Avenue Unit 3, Middleton

Listing courtesy of Restaino & Associates.

$195,000
2 Beds ⋅ 1 Baths
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 Boulevard Unit 3, Middleton

Listing courtesy of Pinnacle Real Estate Group LLC.

$369,900
Build your dream custom home with Jason Thomas Homes on Lot 36 in Pioneer Pointe, a top golf community offering scenic views and luxury homes. This spacious lot offers a flexible building area backing to the golf course, with views of the green on hole 4 at Pioneer Pointe Golf Course, making it perfect for a thoughtfully designed home that suits your lifestyle. Live in a desirable neighborhood with easy access to Verona, Middleton, and Madison, along with nearby recreation and amenities. Work directly with Jason Thomas Homes to design and build your dream home on this outstanding lot (walkout possible).

Lot 36 Eden Court, Middleton

Listing courtesy of Jason Thomas Homes LLC.

$185,000
Rare opportunity for the purchase of a 2nd floor walk-up office condo in Middleton! Unit faces University Ave., and has a fair amount of windows and natural light. Great option for a business owner who is tired of paying rent and wanting to build equity. Size: Approx. 1,500 sq. ft. (Buyer to verify sq. ft. if desired). Layout: 4 offices, work/conf. room, storage, in-suite sink and restroom, reception, some open work area. Condo Fees: $2,674.00 (2025). Parking: Off-street and guest parking

6629 University Avenue Unit 206, Middleton

Listing courtesy of Plato Commercial Real Estate, LLC.

$160,000
1 Beds ⋅ 1 Baths
Fresh, modern, and completely turnkey! This beautifully updated Middleton condo features renovations throughout, offering a clean, move-in ready space you'll love coming home to. includes a dedicated storage unit for added convenience. Set in a vibrant, going community close to shopping, dining, and more- this is low-maintenance living at its best. (Free off-street parking, too!) Please note: some of these images have been digitally altererd.

7401 Century Place Unit 103B, Middleton

Listing courtesy of First Weber Inc - Delafield.

$1,000,000
3 Beds ⋅ 2 Baths
Two lots create a rare opportunity along a quiet channel with direct access to Lake Mendota, inviting a range of possibilities from thoughtful renovation to a ground-up custom build. The existing home sits between two buildable parcels, allowing for expanded outdoor space, future development, or a private lakeside retreat tailored to your vision. Spend mornings on the water boating or fishing, then return to a backyard dock, with a nearby boat launch adding everyday ease. The setting balances a sense of retreat with practical convenience, just off Century Avenue and minutes from local grocers, dining, and daily essentials. Downtown Madison is an easy 20-minute drive, making this an ideal blend of waterfront living and city access.

2809 Dewey Court, Middleton

Listing courtesy of Sprinkman Real Estate.

$57,860
Strategic Office Opportunity in Middleton! Discover a premier professional environment at 1424 N High Point Rd, perfectly situated to elevate your business in the thriving Greater Madison market. This modern office suite offers 2,893 SF of versatile workspace designed to accommodate a variety of operational needs.The floor plan is intentionally designed for adaptability, featuring flexible layouts with the potential to divide larger spaces for a customized fit. The interior is fully equipped for a modern team, boasting: Private Office Suites: 8 Private Individual Offices to accommodate the whole team. Collaborative Bullpen: An open-concept area perfect for team synergy and productivity. Executive Amenities: A dedicated kitchen area and a generous conference room for high-level meetings and presentations. On-Site Features: Private bathrooms inclusive of a shower, ideal for those who bike to work or need a mid-day refresh. This location offers exceptional value at a lease rate of $20.00

1424 N High Point Road Unit 1424, Middleton

Listing courtesy of RE/MAX Preferred.

$2,100,000
Prime Beltline visibility! This 1.52 acre site is perfectly positioned for maximum exposure with 187,000 vehicles per day and surrounded by a good mix of local and national retail and service businesses. Existing building is serviceable for an incoming business - or could be removed to make room for a new concept. Located in an island of the Town of Middleton, the site is currently served by well water. This island is slated to be incorporated into the City of Madison in the future and the option exists to attach to municipal water ahead of schedule. Billboard is on an easement and is not a part of this sale. 2022 Phase II and DNR No Action Required letter are on file. All dimensions are approximate - buyer to verify.

6530 Seybold Road, Middleton

Listing courtesy of Acres Realty.

$1,150,000
5 Beds ⋅ 4 Baths
Discover timeless Mid-Century Modern ranch living in the heart of Middleton. This nearly 3,500 sqft home offers exceptional space & a premier location just one block from the conservancy. This unique 5BR/4BA residence is designed for flexible living. Occupy the spacious 4BR main level while generating income from the private-entry MIL suite w/ indoor parking. A separate LL apartment with its own entrance provides add'l privacy, ideal for multigenerational living or rental. Inside, vaulted timber ceilings, pine floors & expansive windows create a bright, light-filled interior. A stunning stone fireplace anchors the main living area, with a 2nd fireplace in the LL. Located near top-rated schools, parks & 2 blocks from the bus line, this home perfectly blends comfort, flexibility & location.

6644 Columbus Drive, Middleton

Listing courtesy of Mahler Sotheby's International Realty.

$350,000
Premier lot in the Town of Middleton. Glaciers Trail Subdivision. Just steps away from the Ice Age Trail and Town Trails. Adjacent to and across from greenspace. It?s time to build your dream home in one of Madison?s best suburbs. Quiet street with spectacular homes. Great far west side location and Middleton Schools. Bring your own builder.

Lot 15 White Cedar Drive, Middleton

Listing courtesy of First Weber Inc.

$1,975,000
Prime redevelopment opportunity in Middleton along the Parmenter Street corridor. 1.107 acre high-visibility corner lot at Parmenter St & Century Ave located within Tax Increment Financing (TIF) District #5. Zoned Mixed-Use Avenue (MU-A) with Future Land Use designated Urban Mixed Use, supporting higher-density residential mixed-use development. City guidance indicates a mixed-use building with approximately 33% ground floor commercial component at this corner location. Existing building and site improvements allow immediate planning, feasibility, and entitlement work while redevelopment is pursued. Strong frontage, access, and proximity to major commuter routes, employment centers, and west Madison retail amenities. TIF assistance may be available for eligible project costs subject to City approval and development agreement. Ideal for multifamily, mixed-use rental, or condominium development. Buyer responsible for all due diligence, zoning verification, and municipal approvals.

3415 Parmenter Street, Middleton

Listing courtesy of NextHome Metro.

$179,900
2 Beds ⋅ 1 Baths
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 Boulevard Unit 4, Middleton

Listing courtesy of Homecoin.com.

$469,480
3 Beds ⋅ 2.5 Baths
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 Drive, Middleton

Listing courtesy of Encore Real Estate Services, I.

$473,360
3 Beds ⋅ 2.5 Baths
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 Drive, Middleton

Listing courtesy of Encore Real Estate Services, I.

$471,323
3 Beds ⋅ 2.5 Baths
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 Drive, Middleton

Listing courtesy of Encore Real Estate Services, I.

$471,323
3 Beds ⋅ 2.5 Baths
Monthly condo fee $190. Welcome to Canna Lily Cottages at Redtail Ridge-featuring Middleton Schools! Kitchen includes quartz countertops, granite sink, stainless appliances & pantry. Primary bedroom features walk-in closet & 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. Staged interior photos are of a similar model.

4317 Goldeneye Gateway Drive, Middleton

Listing courtesy of Encore Real Estate Services, I.

$469,480
3 Beds ⋅ 2.5 Baths
Monthly condo fee $167. Welcome to Canna Lily Cottages at Redtail Ridge--featuring Middleton Schools! Kitchen includes granite countertops & sink, large island, tile backsplash, stainless appliances, and pantry. Primary bedroom suite features walk-in closet & private bath with tile shower & dual sinks. 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. Interior staged photos are of a similar model.

4303 Goldeneye Gateway Drive, Middleton

Listing courtesy of Encore Real Estate Services, I.

$473,360
3 Beds ⋅ 2.5 Baths
Monthly condo fee $190. Welcome to Canna Lily Cottages at Redtail Ridge-featuring Middleton Schools! Open concept home features great room w/ fireplace & additional flex area. Kitchen includes quartz countertops, large island, granite sink, stainless appliances & pantry. Primary bedroom 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. Staged interior photos are of a similar model.

4307 Goldeneye Gateway Drive, Middleton

Listing courtesy of Encore Real Estate Services, I.

$448,500
3 Beds ⋅ 3.5 Baths
Move-in ready! Welcome to Redtail Ridge Townhomes--featuring Middleton Schools! New townhomes with unimpeded views of 4 acre park across the street! Main level open concept living with stainless/granite kitchens and baths. 3 beds & 2 baths upstairs, 2-car attached garage & ample storage space. Finished basement INCLUDED. Garage enters at basement level. Shared maintenance agreement means that you?ll never need to worry about snow removal or landscape care--all taken care of for you! Shared maintenance fee also includes your homeowners insurance coverage & your Redtail Ridge Master Homeowners Association fee. 10yr builder's limited warranty & 15yr dry basement warranty included! Interior photos & tour are of a similar model. Plans & design selections available upon request.

6854 Belle Fontaine Boulevard, Middleton

Listing courtesy of Encore Real Estate Services, I.

$448,500
3 Beds ⋅ 3.5 Baths
Move-in ready! Welcome to Redtail Ridge Townhomes--featuring Middleton Schools! New townhomes with unimpeded views of 4 acre park across the street! Main level open concept living with stainless/granite kitchens and baths. 3 beds & 2 baths upstairs, 2-car attached garage & ample storage space. Finished basement INCLUDED. Garage enters at basement level. Shared maintenance agreement means that you?ll never need to worry about snow removal or landscape care--all taken care of for you! Shared maintenance fee also includes your homeowners insurance coverage & your Redtail Ridge Master Homeowners Association fee. 10yr builder's limited warranty & 15yr dry basement warranty included! Interior photos & tour are of a similar model. Plans & design selections available upon request.

6850 Belle Fontaine Boulevard, Middleton

Listing courtesy of Encore Real Estate Services, I.

$458,500
3 Beds ⋅ 3.5 Baths
Move-in ready! Welcome to Redtail Ridge Townhomes--featuring Middleton Schools! New townhomes with unimpeded views of 4 acre park across the street! Main level open concept living with stainless/granite kitchens and baths. 3 beds & 2 baths upstairs, 2-car attached garage & ample storage space. Finished basement INCLUDED. Garage enters at basement level. Shared maintenance agreement means that you?ll never need to worry about snow removal or landscape care--all taken care of for you! Shared maintenance fee also includes your homeowners insurance coverage & your Redtail Ridge Master Homeowners Association fee. 10yr builder's limited warranty & 15yr dry basement warranty included! Interior photos & tour are of a similar model. Plans & design selections available upon request. END UNIT, INCLUDES FIREPLACE!

6846 Belle Fontaine Boulevard, Middleton

Listing courtesy of Encore Real Estate Services, I.

$1,399,000
4 Beds ⋅ 4.5 Baths
RECENTLY UPDATED RED BIRCH FLOORS, NEW ROOF, DECK RAILINGS & MORE! Timeless architecture meets modern sophistication in sought-after Middleton Hills. This exceptional 4+ bedroom, 4.5 bath home offers over 4,600 sq ft across three expansive levels, featuring two spacious primary suites with walk-in closets. The premium open-concept kitchen features high-end appliances and flows seamlessly into inviting living and entertaining spaces. The light-filled lower level includes a theater, fireplace, kitchenette, and guest suite. Two offices provide ideal work-from-home flexibility. Enjoy prized green space on two sides, and a screened porch and patio for outdoor living. Luxury bath features include a heated floor, a wall-mounted toilet, walk-in showers, jet tubs, plus laundry on two levels. EV-ready 3+car side-entry garage. Walk to schools, parks, trails, groceries and shops.

6833 Phil Lewis Way, Middleton

Listing courtesy of MHB Real Estate.

$899,000
Excellent Investment Opportunity in prime Middleton Location! Well-maintained duplex in the heart of Middleton, minutes from Downtown Middleton and Greenway Station. Property features two spacious units: both 3 bed, 2.5 baths, fully finished basements for additional living space, and sunroom/office that could be used as a 4th bedroom. Units have private entrance, their own 2 car garage, and are metered separately. Strong rental demand due to location near shopping, dining, parks, and major commuter routes. Ideal for investors or owner-occupants seeking long-term value in a sought-after area. Updates include furnace for both units (2018), 1214 water heater (2024), 1216 water heater (2013). UHP Home Warranty included!

1214-1216 N High Point Road, Middleton

Listing courtesy of MHB Real Estate.

$1,750,000
Beltline frontage with signage! This 14,500 SF multi-unit property is available for the first time in 28 years. Currently occupied with 2 tenants - both with a showroom and warehouse - a new owner will benefit from immediate cash flow. Major tenant vacating at the end of 2027 provides the opportunity for an owner to occupy at that time or re-tenant at market rate. Additional warehouse space is also available across Seybold to the south. Property is a condo unit along with one other neighboring condo on the parcel. Take advantage of this irreplaceable location!

6524 Seybold Road, Middleton

Listing courtesy of Acres Realty.

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