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3452 Crestwood Dr, Shorewood Hills
$2,756,241
4 Beds ⋅ 5 Baths ⋅ 2019822 MLS ⋅ CLOSED Status
OPEN HOUSE CANCELED. Perfectly positioned hilltop in Shorewood Hills, this iconic quarry stone Tudor offers timeless architecture + exceptional setting just moments from UW, hospitals & Lake Mendota. Rich in character w/ hardwood floors, handcrafted millwork & luxury finishes, the home seamlessly blends historic charm w/ extensive updates. Designer kitchen showcases La Cornue + SubZ appliances & dinette w/ fireplace, while refined living spaces feature French château mantel, turreted bedroom + beautifully finished LL. Lovely screened porch overlooks gardens & bubbling stream + Koi pond, offering tranquil setting perfect for morning coffee or relaxed evening entertaining. UL provides 3 beds, 3 baths, large bonus room + laundry for flexible, comfortable living. Elevated design details shine through w/custom tile, finishes, wallpaper, + hand-painted murals. Outdoors, curated gardens feature a bluestone patio, ponds, + private, enclosed grounds. Beautiful slate roof & rare 3 car garage.

3452 Crestwood Dr, Shorewood Hills
2933 Colgate Rd, Shorewood Hills
$1,950,000
4 Beds ⋅ 4 Baths ⋅ 2028689 MLS ⋅ CLOSED Status
SOLD COMP

2933 Colgate Rd, Shorewood Hills
3610 Sunset Dr, Shorewood Hills
$1,865,000
4 Beds ⋅ 3 Baths ⋅ 2018137 MLS ⋅ CLOSED Status
Outstanding location in Shorewood Hills, this 4 bed, 2.5 bath exceptional home offers high-end updates while keeping the old world charm + unbeatable setting overlooking scenic fairways of Blackhawk Country Club. Beautifully updated residence showcases impressive craftsmanship + thoughtfully curated finishes thru-out, creating warm + inviting living spaces. Sun-filled interiors highlight character + elegance, while extensive renovations bring modern comfort + elevated style. Remodeled kitchen + living areas flow seamlessly, reflecting quality materials, refined details + a sense of enduring sophistication. Outdoor living is equally special. Newly built deck creates a perfect place to watch sunsets or relax with lake views. Lovely landscaped yards frame the home w/ lush greenery + colorful plantings, offering privacy, beauty & a tranquil backdrop thru-out seasons. Just moments from Lake Mendota, parks, bike paths, pool + retail.

3610 Sunset Dr, Shorewood Hills
1015 Yale Rd, Shorewood Hills
$1,500,000
4 Beds ⋅ 3 Baths ⋅ 2029375 MLS ⋅ CLOSED Status
SOLD COMP.

1015 Yale Rd, Shorewood Hills
3425 Crestwood Dr, Shorewood Hills
$1,495,000
4 Beds ⋅ 4 Baths ⋅ 2006216 MLS ⋅ CLOSED Status
Completely remodeled and move-in ready, this beautiful home in Shorewood Hills sits hilltop with great views. Recent updates include a new roof, Marvin windows, and LP Smart Siding for exceptional durability and curb appeal. Kitchen boasts stainless steel appliances, quartz countertops, custom cabinetry, and a stylish tiled backsplash. Convenient main-floor mudroom and laundry add everyday ease, while all bathrooms have been beautifully updated. 4 bedrooms up with a primary suite and additional full bath. Enjoy the black iron fenced backyard with stamped concrete patio and professional landscaping—perfect for entertaining. The newly finished lower level offers a spacious rec room, workout area/flex space, full bath, and a unique speakeasy space for memorable gatherings.

3425 Crestwood Dr, Shorewood Hills
3309 Tally Ho Ln, Shorewood Hills
$1,400,000
5 Beds ⋅ 5 Baths ⋅ 2017341 MLS ⋅ CLOSED Status
Rare opportunity to own this never before listed 5 bedroom 2 story in Shorewood Hills! Beautifully renovated over the years this home truly has it all - enter inside to find the bright and open main lvl complete w/ mud & powder room, 2 in-home offices, window filled living/dining room, & kitchen w/ stainless apps, breakfast bar, & dining nook! Brand new 2023 upper level addition is sure to impress w/ 3 beds, a loft & laundry room, and owners suite w/ huge WIC w/ built-ins, stunning en-suite w/ dbl vanity, soaking tub, walk-in tile shower & heated floors! Walkout/exposed basement allows for even more living/entertaining space boasting a spacious family/rec room & 5th bed w/ own private en-suite perfect for hosting guests. Amazing lot w/ no back yard neighbors, deck, stamped patio, & partially fenced in yard suited for a dogs/chickens! 2 car garage & ALL mechanicals/roof replaced in 2023. See docs for more info!

3309 Tally Ho Ln, Shorewood Hills
1007 Edgehill Dr, Shorewood Hills
$1,380,000
4 Beds ⋅ 4 Baths ⋅ 2027052 MLS ⋅ CLOSED Status
SOLD COMP

1007 Edgehill Dr, Shorewood Hills
3415 Blackhawk Dr, Shorewood Hills
$1,200,000
4 Beds ⋅ 2 Baths ⋅ 2021961 MLS ⋅ CLOSED Status
This beautifully updated mid-century modern home offers timeless design in exceptional setting. Filled w/ natural light, home showcases warm hardwood floors, clean architectural lines, + expansive windows that bring the outdoors in. Inviting living room features fireplace, wall of bookcases & an oversized picture window capturing garden views. Thoughtfully updated kitchen w/ large center island offers a seamless flow for both everyday living + entertaining. Updated baths provide a fresh, modern feel, while the loft bedroom impresses w/ vaulted ceiling, creating a bright & airy retreat. Step outside to a spacious deck w/neighborhood views. Perfect for relaxing or hosting gatherings. Ideally located near Shorewood Elementary, Four Corners Park & Blackhawk Country Club, this home offers a rare combination of style, updates and an unbeatable SH lifestyle.

3415 Blackhawk Dr, Shorewood Hills
923 Swarthmore Ct, Shorewood Hills
$1,200,000
3 Beds ⋅ 2 Baths ⋅ 1999656 MLS ⋅ CLOSED Status
Shorewood Hills masterpiece awaits you! Highly sought after location near the Elementary school and the Shorewood pool. The special features awaiting you are skylights in almost every room, a spacious open floor plan, tiled floors and heated floors in the living room, master bedroom and master bath. The circular driveway only enhances the unique attributes including stucco craftsmanship, ranch design, and 2,200+ square ft of quality craftsmanship enhanced by a new Sub-Zero refrigerator and Bose sound system in the home. Heated floors in the Livingroom, Master Bedroom and Master bath. Expect to be impressed! I am confident you will be impressed.

923 Swarthmore Ct, Shorewood Hills
1226 Sweetbriar Rd, Shorewood Hills
$1,175,000
3 Beds ⋅ 3 Baths ⋅ 2012928 MLS ⋅ CLOSED Status
Set on a mature lot in sought-after Shorewood Hills, this charming 2-story Colonial blends historic character with thoughtful modern updates. Built in 1916, the home features 3 bedrooms, 2.5 baths, and approximately 2,000 sq ft of beautifully refinished living space. The main level offers a brand-new semi-custom kitchen with Sub-Zero refrigerator and induction cooktop, cozy family room with natural wood fireplace, and a spacious formal dining room. Upstairs includes three bedrooms and an owners’ suite with a fully tiled bath and heated floors. Extensive updates include new roof, furnace, water heater, plumbing, electrical, skylights, and more. A stabilized 1-car garage, refreshed landscaping, and timeless setting complete this exceptional offering.

1226 Sweetbriar Rd, Shorewood Hills
3329 Tally Ho Ln, Shorewood Hills
$1,108,000
4 Beds ⋅ 3 Baths ⋅ 2016564 MLS ⋅ CLOSED Status
Move-in ready, modern home in Shorewood Hills. Beautifully updated home blends character, comfort, and walkable convenience, just steps to the pool, park, groceries, and restaurants, and minutes to UW–Madison & area hospitals. Stylish kitchen features professional-grade appliances, island, custom cabinetry and opens to a bright living area w/walk-out to deck & connects to family room with fireplace & natural stone surround. Four bedrooms, including a private primary suite, plus a second-floor office with architect-designed roof detail. Finished LL with rec room, flex space, and full bath. High-end lighting & finishes, custom cabinetry & all the details have been added to make this beautiful move-in ready home. Spacious deck, walk-out patio, professional hardscaping, 2-car garage. Yard has more than 100 native plant species w/beautiful trees and shrubs. New roof (2024). Solar panels to be reinstalled.

3329 Tally Ho Ln, Shorewood Hills
1219 Wellesley Rd, Shorewood Hills
$1,100,000
4 Beds ⋅ 2 Baths ⋅ 2011997 MLS ⋅ CLOSED Status
Meticulously maintained mid-century ranch in Shorewood Hills. This beautifully cared-for home features an open dining and living area with vaulted ceilings and a striking brick wall fireplace—perfect for everyday living and entertaining. The spacious primary bedroom offers comfort, while flexible spaces provide potential for up to four additional bedrooms or ideal areas for work, fitness, or hobbies. The lower-level has large family area w/ brick wall fireplace and 3-season room that opens to a large deck and a beautifully landscaped yard, creating a seamless indoor-outdoor connection. Situated in the perfect location to walk to schools, the community pool, hospitals, parks, and more—this home combines mid-century charm, modern comfort, and the best of Shorewood Hills living.

1219 Wellesley Rd, Shorewood Hills
3223 Topping Rd, Shorewood Hills
$1,000,000
4 Beds ⋅ 2 Baths ⋅ 2018995 MLS ⋅ CLOSED Status
Charming Cape Cod on nearly 1/3 acre in an unbeatable Madison location! This 3BR/1.5BA home blends timeless character with thoughtful updates, featuring hardwood floors, original built-ins, and vintage hardware. The lovingly updated kitchen offers an adjacent dining area and easy flow for everyday living. A sun-drenched sunroom overlooks the backyard—perfect for relaxing or entertaining. The bright, open main level includes a primary bedroom, full bath, and second bedroom. Upstairs, you’ll find two adorable bedrooms with built-ins and a convenient half bath. The exposed walk-out lower level features a rec room, bonus room, and laundry area—ready for your personal touches. Oversized 2-car garage and spacious yard complete the package. Ideal location just steps to the elementary school, pool, tennis courts, Blackhawk Country Club, UW Hospital, and nearby shops and restaurants. A true storybook setting for your next chapter.

3223 Topping Rd, Shorewood Hills
3400 Tally Ho Ln, Shorewood Hills
$970,000
2 Beds ⋅ 2 Baths ⋅ 2021337 MLS ⋅ CLOSED Status
Own a piece of Shorewood Hills history with this one-of-a-kind home built in 1854! Step into the bright, airy kitchen, an addition that connects the garage to the original home, blending modern updates with its historic style. The formal dining room is loaded with windows and has access to a deck and a large private yard. The main level has a full bath and 2 bedrooms, including a spacious primary with a walk-in. The fully exposed lower level invites you in with the huge windows and breathtaking views of the surrounding woodland gardens. A charming reading nook leads to a versatile space perfect for an office. The cozy den anchored by an efficient wood-burning stove is the perfect spot on chilly days. Outside, relax on the patios and decks, then stroll along winding paths to discover peaceful spots to pause and take in the scenery. This home stays true to its history, showcasing original details and character throughout. Will you be the next owner to continue its legacy?

3400 Tally Ho Ln, Shorewood Hills
1514 Wood Ln, Shorewood Hills
$900,000
3 Beds ⋅ 2 Baths ⋅ 2008313 MLS ⋅ CLOSED Status
Tucked into a serene, nature-filled lot, this charming home blends warmth, character + comfort in Shorewood Hills. Surrounded by mature trees, the setting offers a peaceful retreat while still being moments from community amenities, parks + schools. Inside, you’ll find a spacious living room filled w/natural light, creating a welcoming space for gathering. Bright sunroom brings the outdoors in year-round, while the screened porch offers the perfect spot to enjoy morning coffee or summer evenings surrounded by nature. A ML bedroom or convenient home office, provides flexible living options to fit your lifestyle. Upstairs offers 2 addtl bed + full bath & LL features large laundry area + rec room. Surrounded by parks w/ walking trails & a 5 minute walk to the lake. Make it what you want!

1514 Wood Ln, Shorewood Hills
1234 Sweetbriar Rd, Shorewood Hills
$885,000
3 Beds ⋅ 2 Baths ⋅ 2025022 MLS ⋅ CLOSED Status
Welcome home to Shorewood Hills! This historic home offers over 2,000 square feet of living space on a level, one-third-acre lot. The welcoming foyer opens to a spacious living room featuring a wood fireplace, original built-in cabinets and access to the private backyard. The charming kitchen offers great counterspace and storage. Entertaining is easy in the formal dining room. The classic details continue upstairs in the bedrooms with custom dormer windows, woodwork, and built-ins. Primary bedroom with attached bonus room. The original hardwood floors add character and timeless appeal throughout much of the home, while the functional layout provides flexibility. With large rooms, 1.5 baths, and a premier location near parks, schools, and shopping, this is a rare opportunity to create your dream home in one of the area's most sought-after neighborhoods.

1234 Sweetbriar Rd, Shorewood Hills
1111 Amherst Dr, Shorewood Hills
$855,000
3 Beds ⋅ 2 Baths ⋅ 2026462 MLS ⋅ CLOSED Status
Nestled in the heart of Shorewood Hills, this classic two-story Colonial offers the perfect blend of character, comfort, and location. Hardwood floors flow throughout the home, creating a warm and inviting atmosphere. The kitchen features solid-surface countertops, and an island that opens to the dining area. The main level also includes a living room with a gas fireplace and built-in bookcases, a separate family room overlooking the backyard, and a convenient half bath. Step outside to a secluded backyard with a hot tub and direct adjacency to Bradley Park. Upstairs you'll find three bedrooms and a full bath. Enjoy the convenience of walking or biking to UW Hospital, the University of Wisconsin campus, Picnic Point, neighborhood restaurants, shops, parks, community pool, sled hill, and Lake Mendota. Experience all that Shorewood Hills has to offer in one of Madison's most sought-after communities.

1111 Amherst Dr, Shorewood Hills
1006 Edgehill Dr, Shorewood Hills
$800,000
3 Beds ⋅ 2 Baths ⋅ 2021060 MLS ⋅ CLOSED Status

1006 Edgehill Dr, Shorewood Hills
3209 Topping Rd, Shorewood Hills
$525,000
3 Beds ⋅ 1 Baths ⋅ 2025350 MLS ⋅ CLOSED Status
Nestled in the heart of sought-after Shorewood Hills, this charming home offers the perfect blend of timeless character and an unbeatable location. Plan for a beautiful remodel and customize your layout and finishes This investment holds many possibilities. Enjoy tree-lined streets, nearby parks, and the vibrant community atmosphere that makes Shorewood Hills so desirable. Just minutes from the University of Wisconsin–Madison campus, downtown Madison, Lake Mendota, local schools, shopping, coffee shops, and neighborhood dining. Easy access to bike paths, recreation, and cultural attractions adds to the appeal. A rare opportunity to enjoy convenience, charm, and one of the Madison area’s most beloved neighborhoods.

3209 Topping Rd, Shorewood Hills

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.