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4965 Championship Cir, Westport
$2,850,000
3 Beds ⋅ 4 Baths ⋅ 2020779 MLS ⋅ CLOSED Status
Set in the gated Woods Neighborhood in The Community of Bishops Bay, this stunning home sits on the 9th fairway of The Bishops Bay Country Club Golf Course, while offering unparalleled views of Lake Mendota, the North Mendota Wildlife Area Prairie Unit and the Holy Wisdom Monastery Woodlands. With 4,300 square feet of living space and more than 1,000 square feet of outdoor deck area, this residence seamlessly blends natural beauty with sleek, modern comfort. Step inside to discover a refined open-concept interior grounded by wide-plank oak flooring, custom-designed cabinetry throughout, and expansive floor-to-ceiling windows that frame breathtaking lake and golf course vistas from nearly every room. The heart of the home is a state-of-the-art chef’s kitchen featuring bespoke cabinetry and top-tier Sub-Zero and Wolf appliances, including 36” designer refrigerator and freezer columns. Lower level provides a recreation room for social gatherings. Showings begin April 18th at noon.

4965 Championship Cir, Westport

4606 Signature Dr, Westport
$1,925,000
5 Beds ⋅ 6 Baths ⋅ 2017302 MLS ⋅ CLOSED Status
Nestled on a serene, private wooded lot in the gated community of Bishops Bay, this exceptional residence embodies refined elegance and effortless comfort. A grand foyer unfolds into an expansive great room w/wet bar, equally suited for sophisticated entertaining and evenings by the fire. The open design transitions seamlessly to a sun-filled sunroom just off the formal dining area, creating a warm, inviting atmosphere year-round. The luxurious primary suite offers a private sitting room with its own fireplace, along with custom dual walk-in closets. Upstairs, three generously sized bedrooms and two full baths provide space and privacy. The walk-out lower level is designed for both relaxation and hosting, featuring a media room, secluded guest suite, and a private patio complete with hot tub. This home also boasts three separate unfinished basement areas offering over 2,000 square feet of storage space. A heated 4+ car garage with epoxy floors adds both function and distinction.

4606 Signature Dr, Westport

3931 S Meadow Dr, Westport
$1,925,000
4 Beds ⋅ 6 Baths ⋅ 2006430 MLS ⋅ CLOSED Status
Nestled on 3.5 private acres in Fox Bluff, this stunning French Country estate blends refined elegance with natural beauty. Enjoy serene views and your own orchard bordering the peaceful Holy Wisdom Monastery. Inside, exceptional craftsmanship shines from the grand two-story foyer and open staircase to the library with custom built-ins. The gourmet kitchen showcases granite countertops, high-end appliances, rich cherry cabinetry, and a hearth room centered around a beautiful fireplace. The main-level primary suite features French doors to the deck, soaking tub, sauna, and a cedar closet. A guest suite with bonus room is upstairs along with two more bedrooms. A new roof was installed in 2025. The adjacent parcel (Lot #343 of Bishops Bay’s The Woods development) is included with the sale.

3931 S Meadow Dr, Westport

5928 Burning Prairie Dr, Westport
$1,740,000
5 Beds ⋅ 4 Baths ⋅ 2015194 MLS ⋅ CLOSED Status
Stunning Soft Modern backing to trees and private park. An infusion of light through Marvin windows/two story living room w/exposed beams. Expansive kitchen w/hidden pantry, Amish cabinets, quartz, Cove, Wolf, Sub Zero, Chef's island w/custom walnut table, wood floors on the main level, LVP lower, stairs are hand welded railings w/custom solid wood treads, master w/heated floor/glass & tile walk-in shower, double sinks & large custom closet, expansive laundry/mud room w/pull out drying racks, raised built-in washer&dryer built-in benches off huge garage w/epoxy flr. Upper level w/Loft + 2 large bedrooms & beautiful bath. LL w/huge rec room, built-in bar/kitchenette, glass enclosed wine room, 4th bdrm/loft (non conforming), massive Exercise/play room. EZ Breeze screen sun room, back deck opens to mature trees and trails to a private park

5928 Burning Prairie Dr, Westport

6128 Imperial Dr, Westport
$1,425,000
5 Beds ⋅ 3 Baths ⋅ 2025890 MLS ⋅ CLOSED Status
Set on a private hilltop lot with exceptional views and wooded acreage, this four acre country estate is now available for sale. The pool, expansive patio area and fire pit all open to an incredible tree line in the back of the property. Views east from the first floor four-season sunroom bring in morning sunlight, while western views of the sunset over the countryside are part of the evening views. The open concept large kitchen, sunroom, and living room showcase beautiful views of the pool and backyard. A formal dining room, office, primary bedroom with ensuite and a guest bedroom complete the first floor. The lower level includes two additional bedrooms, full bathroom and a large rec room with wet bar. A private exercise room is part of the lower level which can be easily converted to a 5th bedroom. The home was quality constructed by Greg Hensen Builders and has been exceptionally maintained, with extensive remodeling throughout. Home and setting are truly remarkable!

6128 Imperial Dr, Westport

5786 Derby Downs Dr, Westport
$1,420,000
5 Beds ⋅ 5 Baths ⋅ 2015390 MLS ⋅ CLOSED Status
Luxury meets function in this meticulously finished Carriage Ridge home. Soaring foyer leads to a light-filled great room with hardwood floors & eye catching chevron shiplap fireplace. Open-concept gourmet kitchen & eating area overlook a tranquil, wooded private backdrop, while the formal dining room & three-season porch are great for entertaining. ML primary ensuite with a spa-like bath and office. UL offers 3 generous bdrms & 2 full baths. Partially finished LL expands living space with a media room & additional bedrooms with full bath. Bonus features include mudroom, laundry room & a pet grooming station. The backyard has a nice patio space and is an open slate with a large yard, offering ample space for the creation of a pool or outdoor dining & kitchen.

5786 Derby Downs Dr, Westport

5663 Cottontail Dr, Westport
$1,383,500
5 Beds ⋅ 5 Baths ⋅ 2029445 MLS ⋅ CLOSED Status
Luxury meets timeless design in this exceptional custom home, thoughtfully crafted with premium finishes and impeccable attention to detail. The chef's kitchen by Dream Kitchens features Wolf and Sub-Zero appliances, custom cabinetry, and an expansive island that opens to inviting living spaces with a gas fireplace and elegant tray ceilings. Designed for both everyday living and entertaining, the home offers 5 bedrooms, 4.5 baths, two versatile bonus rooms, and a beautifully finished lower level complete with a wet bar and fitness room. Step outside to enjoy a screened porch, composite grilling deck, stamped concrete patio, fire pit, and professionally landscaped, fully fenced yard. With Canadian hardwood floors, Hunter Douglas window treatments, a home theatre, countless thoughtful upgrades, and a location just steps from neighborhood parks, this move-in-ready home offers luxury living at its finest.

5663 Cottontail Dr, Westport

5732 Tuscany Ln, Westport
$1,375,000
5 Beds ⋅ 6 Baths ⋅ 2008425 MLS ⋅ CLOSED Status
Located in the popular Tuscany Ridge neighborhood! Featuring open, flowing layout, blending quality, elegance & comfort w/over 6000 sqft of beautifully designed space backing up to a conservancy. Stunning chef’s kitchen w/cherry cabinetry, Wolf cooktop, dry bar, island, granite counter tops & walk-in pantry. Gleaming birch flooring, flr to ceiling fireplace, main flr executive office w/fireplace, primary suite you will love, 2nd bdrm ensuite, integrated audio system, huge screened porch & deck. Gather family & friends! Expansive walkout LL features an amazing theatre rm, rec rm, bar rm, 2-way fireplace, wine rm & more! 4 zone HVAC system, in-floor radiant heat for LL, garage & primary bath. Stairs from garage to LL. Low Westport taxes! More details in doc section.

5732 Tuscany Ln, Westport

5738 Tuscany Ln, Westport
$1,300,000
5 Beds ⋅ 4 Baths ⋅ 2022673 MLS ⋅ CLOSED Status
Showings begin May 13. Set on 1.25 acres in sought-after Tuscany Ridge, this custom-built home offers over 4,400 sq ft of thoughtfully designed living space with the flexibility and features today’s buyers are looking for. The open main level showcases vaulted ceilings, a stunning great room with fireplace, and a beautifully designed kitchen featuring soft-close Amish cabinetry, oversized island, pantry, and touch faucet. The main floor primary suite includes a spa-like bath and spacious walk-in closet, while the finished lower level adds additional living, entertaining, fitness, and guest space. Enjoy evenings around the backyard fire pit or relax in the three-season room overlooking the private setting. The oversized 3-car garage is a standout with a 12’ third stall door and enough depth to accommodate a 26’ camper or boat. Smart home features, exposed lower level windows, wet bar, and quality custom finishes throughout complete this exceptional Waunakee property.

5738 Tuscany Ln, Westport

5596 Surrey Ln, Westport
$1,250,000
4 Beds ⋅ 5 Baths ⋅ 2016354 MLS ⋅ CLOSED Status
Waunakee Schools-Discover this exceptional 2-story custom home by architect E. Edward Linville, located in the charming Equestrian community of Carriage Ridge. Enjoy a contemporary layout featuring soaring cathedral ceilings and exquisite custom finishes. The striking two-way stone fireplace beautifully links the modern living and dining areas to the gourmet kitchen and breakfast nook. The main level boasts a private and spacious owner’s suite, while the upstairs hosts two additional bedrooms with baths and a cozy lofted sitting area. Outside, entertain in style with a beautiful private in-ground salt water pool, expansive deck, and fire pit. This remarkable home is a must-see! Low Westport Taxes. Miles of beautiful walking trails thought out the subdivision.

5596 Surrey Ln, Westport

5774 Tuscany Ln, Westport
$1,200,000
5 Beds ⋅ 5 Baths ⋅ 2009932 MLS ⋅ CLOSED Status
Here it is! This one is so elegant and classy, yet exudes so much warmth and comfort.  Sunshine absolutely streams in from the wall of windows in the 2-story great rm. This is one of my favorite floor plans ever, w/really gorgeous finish choices - it's just perfect. Stunning kitchen has been quality-tested for both large gatherings and for sweet family breakfasts at the big island. The porch is a cozy spot with the coolest-ever, smooth-sliding accordion door. Entire wall opens to welcome in the outdoors (and friends) on a cool fall night by the fire, or on every summer day. Don't miss the gaming bunker! Since they are relocating, Lauren and JJ are including the upgrade package of truly wonderful neighbors who have become family. Features like that are priceless, and not always available.

5774 Tuscany Ln, Westport

5119 Reynolds Ave, Westport
$1,200,000
5 Beds ⋅ 4 Baths ⋅ 2001405 MLS ⋅ CLOSED Status
This custom built home backs up to Governor Nelson State Park and is just across from Lake Mendota. The main level features a spacious living room with a stunning stone wood-burning fireplace, formal and informal dining areas, a den/office, dual mudrooms, and a convenient laundry room. The kitchen is a chef’s dream with stainless appliances, granite countertops, a copper farmhouse sink, walk-in pantry, and breakfast bar. The main-level primary offers a walk-in closet, ensuite featuring a jetted tub, walk-in tile shower, and separate toilet room. The lower level is exposed and ready to be finished. Enjoy the outdoors from the screened wraparound porch or low-maintenance deck. An out building provides additional storage. The attached 3-car garage is a bonus.

5119 Reynolds Ave, Westport

5606 Shenandoah Dr, Westport
$1,197,000
5 Beds ⋅ 4 Baths ⋅ 2009013 MLS ⋅ CLOSED Status
Welcome to this stunning 2021-built home in the sought-after Carriage Ridge neighborhood. Designed with modern finishes and an open layout, the space is perfect for entertaining, flooded with natural light. The chef’s kitchen boasts high-end appliances, a prep area, and walk-in pantry, seamlessly flowing into the two-story living room with floor-to-ceiling windows, a stone surround fireplace, and custom built-ins. Ideal for remote work, the home offers two dedicated offices. Upstairs, a catwalk leads to the luxurious primary suite featuring a walk-in closet and a spa-like shower room with a soaker tub. The newly finished basement includes a pub room, sunken workout room w/sauna, and a prepped area for a future walk-in safe. Oversized 3+ car garage includes basement access.

5606 Shenandoah Dr, Westport

4857 Autumn Leaf Ct, Westport
$1,035,000
6 Beds ⋅ 5 Baths ⋅ 2015349 MLS ⋅ CLOSED Status
Waunakee Schools. An exceptional custom-built Waunakee home on a quiet cul-de-sac, set on a private 0.79-acre lot. This 6-bedroom, 4.5-bath residence showcases beautiful wood floors and elevated finishes through out the home. huge Main-level boasts primary suite w/heated floors and steam shower, home office, and a chef’s kitchen open to the dining area, 15x7 walk in butlers pantry, morning room and grand living room with 12’ ceilings, beautiful and cozy stone fireplace, and south facing wall of windows with tons of light leading to the large deck. 4 bedrooms up, one is an ensuite .The expansive walkout lower level offers an expansive Family room/rec room, exercise room, bedroom, and full bath—with heated floors, ideal for entertaining or multi-generational living. Storage is amazing. A rare blend of space, comfort, and privacy!Low Westport taxes.3 car garage.

4857 Autumn Leaf Ct, Westport

5654 Cobblestone Ln, Westport
$1,025,000
5 Beds ⋅ 4 Baths ⋅ 2014822 MLS ⋅ CLOSED Status
Carriage Ridge ~ Waunakee Schools + Town of Westport Low Property Taxes! METICULOUSLY MAINTAINED HOME ON OVER A 3/4 ACRE PRIVATE MATURE LOT! Executive 2-Story Home w/5 Bedrooms (1ST FLOOR OWNER'S SUITE), 1st Floor Office, 3.5 Baths, 1st Floor Laundry + 3 Car Garage w/Steps to the Basement! GORGEOUS Kitchen w/Maple Cabinets+Maple Floors, Granite Countertops, Large Walk-in Pantry, Work Island+Huge Dinette Area that Opens to Great Room w/Soaring Ceilings, Fireplace + Tons of Windows w/an Abundance of Natural Light! MAIN LEVEL BOASTS A PRIVATE & SPACIOUS OWNER'S SUITE W/a Large Walk-in Closet, STUNNING Remodeled Walk-in Shower+Soaking Tub while the Upstairs hosts 4 Additional Bedrooms! AMAZING Family Room in Exposed L/L w/2nd Fireplace+Wet Bar...Perfect for Entertaining! New Furnace-2023! NEW Roof-2020! NEW A/C 2019! Miles of Beautiful Walking Trails+Close to Lake Mendota & Governor Nelson Park...

5654 Cobblestone Ln, Westport

5476 Walden Bay Dr, Westport
$875,000
4 Beds ⋅ 4 Baths ⋅ 2022409 MLS ⋅ CLOSED Status
Bring your boat! This stunning 3705 sqft, 4 bdrm, 3.5 bath includes a boat slip on Lake Mendota! All the amenities of lake life without high taxes! Extensively landscaped gated entrance frames this magnificent 2 story on a quiet private street on the banks of sought after Lake Mendota! Walk in & be drawn to a magnificent great rm featuring a high cathedral ceiling, gas fireplace & large windows flooding natural light through the wide open flr plan which draws in the large granite & stainless steel kitchen w/an abundance of cabinets, pantry, & huge island! Relaxing screen porch w/access to a spacious deck overlooking the 1/3 acre lot w/lawn irrigation. French drs & elegant white woodwork accent the first flr office. Open staircase leads to a charming reading loft. Retreat to a King size Owner Suite-unwind with a whirlpool bath. Wonderful LL family rm w/wet bar, Guest Suite & bath. Enjoy Lake Life at an affordable price in top rated Waunakee School district! $270/mo condo fee

5476 Walden Bay Dr, Westport

4960 Prairie Spring Ct, Westport
$834,000
4 Beds ⋅ 3 Baths ⋅ 2015469 MLS ⋅ CLOSED Status
An exceptional opportunity to own in The Prairie at Bishops Bay, within the Waunakee School District. This thoughtfully designed ranch, positioned on a corner cul-de-sac lot, blends comfort and sophistication with open main-level living, a well-appointed cook’s kitchen, inviting fireplace, screened porch, and a calming primary suite with tiled shower. The finished lower level is intentionally designed, offering a spacious family room, private guest bedroom, and full bath with finishes that echo the main level. An expansive unfinished area with double doors provides exceptional storage and exciting potential for a home gym or future flex space. Outdoors, enjoy a fenced yard and patio for everyday living or entertaining. A 3-car garage adds convenience, while neighborhood amenities include a beautifully designed community center, fitness facilities, and pool—an elevated, low-maintenance way to experience Bishops Bay living.

4960 Prairie Spring Ct, Westport

4872 Trantin Ct, Westport
$815,000
3 Beds ⋅ 3 Baths ⋅ 2021756 MLS ⋅ CLOSED Status
Tucked on a quiet cul-de-sac just moments from Lake Mendota, this beautifully updated Waunakee home blends comfort, function, and style. Enjoy the ease of main floor living with a spacious primary suite, convenient laundry hookups, and thoughtfully remodeled baths. The inviting layout offers 3 bedrooms, 2.5 baths, functional mudroom, and generous living spaces designed for everyday living and entertaining alike. Step outside to a large patio perfect for summer gatherings, morning coffee, or relaxing evenings. Additional highlights include a newer roof and an oversized 3-car garage with ample storage. Located near parks, trails, and all Waunakee/Middleton have to offer, this move-in ready home delivers an ideal mix of location, updates, and lifestyle.

4872 Trantin Ct, Westport

5576 Huntingwood Way, Westport
$800,000
4 Beds ⋅ 3 Baths ⋅ 2008152 MLS ⋅ CLOSED Status
Imagine living in a mid-century modern designed home on .9 acres & 125' of frontage with the Six Mile Creek running behind it. A natural waterway known for its recreational activities & fishing. Now imagine this same cedar & stone home nestled on a spectacular lot with mature hardwoods. You will love the deck, patios & 2 screened porches so perfect for listening to the many varieties of birds while watching wildlife go by. You don't have to imagine anymore because this spectacular home exists! This 4 bedroom, 3 bath home includes 3,700 sq. ft., 2 fireplaces, remodeled kitchen & plenty of room to sit back & relax. Beautiful mature gardens welcome you as you head up the long driveway to the house. This is a must see & so close to all of the activities in Madison, Waunakee & Sun Prairie.

5576 Huntingwood Way, Westport

5829 Prairie Cloud Ct, Westport
$750,000
5 Beds ⋅ 4 Baths ⋅ 2000448 MLS ⋅ CLOSED Status
Stunning 3-year-old ranch in Bishops Bay with vaulted/10 ft ceilings on the main level & 10 ft ceilings in the finished lower level. Bright and open throughout! Enjoy an open-concept kitchen, dining, and living area with fireplace, plus a flex room/4th main lvl bed & deck--all ideal for entertaining! New LVP flooring! Chef's kitchen features granite counters, SS appliances, and vent hood over gas stove. The private primary suite includes a jetted tub, tiled shower, and massive walk-in closet. Mudroom with laundry and cubbies! Newly renovated lower level offers a huge rec room, 5th bedroom, kitchenette, fireplace, and two bonus rooms for hobbies or workouts. Walk out to the backyard patio, perfect for bonfires! Close to Governor Nelson state park, golf courses, and community trails!

5829 Prairie Cloud Ct, Westport

5494 Sunset Trl, Westport
$665,000
3 Beds ⋅ 3 Baths ⋅ 2011764 MLS ⋅ CLOSED Status
This stunning custom-built 3bed, 3bth ranch sits on a spacious, wooded ¾acre lot, offering privacy and tranquility with the benefit of low Westport taxes & top-rated Waunakee schools. Inside, you’ll find a large open-concept kitchen w/ granite countertops & newer appliances, perfect for cooking and entertaining. Formal dining rm (currently a den/office) provides flexible living space. The huge primary suite features dual walk-in closets & a luxurious bath with double vanities, a walk-in shower, & jetted tub. Enjoy the convenience of main-level laundry & large finished, exposed lower level with a family room, exercise rm & space to add a 4th bdrm. Car enthusiasts & hobbyists will love the oversized, heated 3+car garage. Step outside to a large deck, perfect for relaxing or entertaining.

5494 Sunset Trl, Westport

5566 Mary Lake Rd, Westport
$650,000
5 Beds ⋅ 3 Baths ⋅ 2020299 MLS ⋅ CLOSED Status
Welcome to this beautifully updated home in a peaceful Waunakee setting, offering space, comfort, and style throughout. The main level shines with a fully remodeled kitchen featuring Amish-built cabinetry, soft-close features, a large island, and modern finishes, all opening to a spacious living area filled with natural light. A cozy sunroom surrounded by windows creates the perfect spot to relax and enjoy views of the expansive yard. The remodeled lower level offers additional living space with a warm, inviting feel and great flexibility. Enjoy an extra-large garage, abundant storage throughout, and a backyard complete with a shed, composite deck, and firepit—ideal for everyday living and entertaining. Ideally located near parks, trails, and Waunakee schools with low Westport taxes.

5566 Mary Lake Rd, Westport

5974 River Rd, Westport
$625,000
3 Beds ⋅ 3 Baths ⋅ 2008968 MLS ⋅ CLOSED Status
Ready for immediate occupancy(virtually staged.) RARE FIND! 3.86 ACRES! Low Westport Taxes! Waunakee Schools! Jaw dropping 64x32 detached HEATED OUTBUILDING (Holds 8-10 cars) plus home has attached 2car garage! Nestled between Country Day School & Drumlin Winery & lot of Conservancy land on River Rd, you’ll find this lovingly cared-for country delight! Huge front Living rm, Dining, Family Rm & Awesome 3-story tower that boasts countryside views! This home has had many updates over the years including: NEWER siding, roof & windows apprx. 15 years ago, Updated kitchen with hickory cabinets &granite countertops apprx 19 yrs, refrigerator 5-6 yrs, & much more! No HOA-Bring your 4 wheeler, snowmobiles, camper, boat, & trailers- You're in the Country!

5974 River Rd, Westport

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