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501 Clifden Dr, Madison
$815,000
5 Beds ⋅ 3 Baths ⋅ 2023768 MLS ⋅ CLOSED Status
Welcome home to 2,500 sq. ft. of above-grade living space on one of the most desirable streets in Westmorland! This charming 1950s home has been updated and well maintained, featuring a significant 1998 addition that added a large kitchen, mudroom, and a primary ensuite with a full bath. Original red oak flooring, arched doorways, built-ins & alcove windows preserve the home's historic character including a wood-burning fireplace. The main floor includes 2 bedrooms + full bath. Upstairs you'll find 3 additional bedrooms and a bonus room. Fenced yard and attached 2 car garage! Walking distance of the library, local coffee shops, schools, and ice cream. Easy access to the SW bike path leading directly to the UW campus and downtown Madison. Experience summer concert series, 4th of July festivities to winter festivals! Large closets and extensive storage. New metal roof '19, LP SmartSide -'17, windows- '00 & '04, water heater-'20, A/C- '17, furnace '09, 200 amp electrical box.

501 Clifden Dr, Madison
622 Chatham Ter, Madison
$782,000
4 Beds ⋅ 3 Baths ⋅ 2010631 MLS ⋅ CLOSED Status
Tucked on a quiet cul-de-sac in highly sought-after Westmorland, this updated home offers a warm blend of community and comfort. Inside you'll find a large modern kitchen with open flow to the dining room and deck, perfect for hosting or everyday living. Two cozy family rooms, one with a fireplace, create space to spread out, while the expansive fenced backyard is ideal for play and peace of mind—fully visible from the kitchen window. Enjoy two patios for relaxing or entertaining outdoors. Updates include a new roof ('24), finished basement with 4th bedroom ('21), newer windows, and recessed lighting. Just 2 blocks to Westmorland Park and year-round neighborhood events, plus quick access to Monroe St, Hilldale, Schools, and downtown via bike or foot. A Madison gem with room to thrive.

622 Chatham Ter, Madison
614 Chatham Ter, Madison
$750,000
4 Beds ⋅ 2 Baths ⋅ 2019084 MLS ⋅ CLOSED Status
Spacious 4-br, 2-bath home in highly sought-after Westmorland. Tucked in a quiet cul-de-sac on the Near West Side, perfectly positioned in the heart of Madison. Solid hickory hardwood floors upstairs, durable porcelain tile downstairs. Natural light from large windows illuminate the main living room + dining room. Enjoy a spacious kitchen with ample storage, and a 2nd dining area that flows into a family room with sliding doors to the backyard. Primary room + full bath on the main floor. Lower level has a large 3rd living area + 3 br + full bath. Steps to Westmorland Park, coffee, and the SW Bike Path. This home offers a peaceful retreat and a vibrant community, with easy access to amenities including dining, entertainment, grocery, shopping, downtown, schools, libraries, hospitals, UW, main roads (Monroe, Odana, Midvale), lakes and more. Approx $185k invested into landscaping, proper grading + 3 large decks. A must-see home in an excellent location!

614 Chatham Ter, Madison
4026 Paunack Ave, Madison
$715,000
3 Beds ⋅ 2 Baths ⋅ 2016169 MLS ⋅ CLOSED Status
Welcome home to this beautiful solid home in the heart of the highly desirable Westmorland neighborhood—where timeless charm meets thoughtfully designed high-end updates. Refinished hardwood floors, fireplace, abundant natural light, and a layout that feels both warm and functional. The kitchen and baths were fully renovated in 2016, showcasing quality finishes and modern style, while new windows and a new roof (2017) provide peace of mind for years to come. Enjoy outdoor living with a charming front porch with farmhouse vibes, a screened porch for relaxing evenings, and a generous backyard enclosed by an iron rod fence—great for entertaining, pets, or play. A 1-car attached garage adds everyday convenience. Located just steps from Westmorland Park, and within easy walking distance to schools, neighborhood parks, coffee shops, and ice cream, you’ll love being part of a community known for its festivals and unbeatable walkability. Basement could be finished to add more space and bath.

4026 Paunack Ave, Madison
445 Caromar Dr, Madison
$710,000
3 Beds ⋅ 2 Baths ⋅ 2027440 MLS ⋅ CLOSED Status
Accepted offer - Open house cancelled. Meticulously maintained over the years, this home features a thoughtful addition, an updated kitchen, and two full baths and an attached garage! Gleaming with charm, the interior offers versatile living spaces, including a living and dining room w/a bay window, 2nd dining area, cozy den, and a first-floor office. Beautiful red oak hardwood floors run throughout the entire home. The second level includes three nice-sized bedrooms and access to a bonus walk-up attic space for storage or a play area. The outdoor living space is equally impressive, featuring a nice screened porch!Overlooking a large, beautifully landscaped yard, a patio for grilling, a newer storage shed, and a tree house. Proximity to Midvale Elementary, Queen of Peace, Sequoya Library, coffee shops, ice cream. Situated in one of Madison’s desirable neighborhood, known for festivals at Westmorland Park! Appliances '26, Roof '17, windows '09&'11, H2O heater '20, furnace '19, A/C '24.

445 Caromar Dr, Madison
9 Frederick Cir, Madison
$709,000
4 Beds ⋅ 2 Baths ⋅ 2018648 MLS ⋅ CLOSED Status
Charming 1953 gem in the heart of Westmorland! This beautifully maintained 4-bedroom, 2 full bath home blends timeless character with thoughtful updates. Sunlight pours in from south, east, and west exposures, highlighting the gorgeous hardwood floors, built-ins, and stunning corner windows that give this home its unmistakable charm.The inviting kitchen features granite countertops, a gas range, and functional layout. The main living space is spacious and boast french glass doors leading to the deck overlooking the landscaped yard which backs up to the SW bike path. Inside, enjoy the convenience of a mudroom, abundant storage with closets galore, and a finished lower level living room with a cozy gas fireplace. The attached 2-car garage and new windows add both comfort and practicality. Tucked on a quiet court, this home offers a peaceful setting in a neighborhood known for it's festivals, and close to coffee shops, restaurants, parks, schools, close to the Arb! Easy commute to UW!

9 Frederick Cir, Madison
588 Park Ln, Madison
$700,000
4 Beds ⋅ 2 Baths ⋅ 2010959 MLS ⋅ CLOSED Status
Sold Comp.

588 Park Ln, Madison
506 Holly Ave, Madison
$675,000
4 Beds ⋅ 2 Baths ⋅ 2020375 MLS ⋅ CLOSED Status
No showings until Open House Sunday, April 12, 11 a.m – 2 p.m. This well-maintained 4-bedroom, 2-bath Cape Cod offers quiet, tree-lined living in the heart of Westmorland. Updates include ‘26 furnace, ‘18 roof, 200-amp electrical, windows, chimney, gutters/downspouts & R50 attic insulation. The inviting living room features a wood-burning fireplace, while the large sun-filled family room opens to a deck and fenced backyard with storage shed. Over 600 sq ft of flexible lower-level space includes a rec room, billiard room, and ample storage—perfect for workouts, game nights, or a home office. Walk the “secret path” to Sequoya Library, schools, parks, and cafes, and hop on the SW bike path for easy access to campus and downtown. Join this vibrant Near West neighborhood in time for its annual Fourth of July festival and many other community gatherings!

506 Holly Ave, Madison
555 Glen Dr, Madison
$657,000
4 Beds ⋅ 2 Baths ⋅ 2014526 MLS ⋅ CLOSED Status
Come home to this gorgeous mid-century solar roof ranch in beloved Westmorland. Backing to the SW commuter bike path, green space to the east, enjoy serene living in this private wooded setting just moments from Monroe St + the UW Arboretum! Expansive light windows, wood burning FP, stunning hardwd flrs and built-in shelving. Entertain+create culinary delights in the Cooks kitchen w/ gas range, ample prep space, pantry, brkfst bar+sitting/pet nook. Unwind in the Owners BR w/ open closet dressers, BR 2 w/ built-in shelves. Perfect for cheers+chilling, BR 3 is ideal as a den/playroom/office w/ walk-out to spacious deck overlooking the trees. The fully built-out walk-out lower-level functions as a private one-BR apartment w/ kitchenette, dining, family rm, and dual vanity shower BA. Previously an Airbnb hosting space, it offers excellent potential for income, teens, guests, or multigenerational living. A separate artist studio/playhouse/yoga/music escape completes this truly unique home.

555 Glen Dr, Madison
560 Toepfer Ave, Madison
$645,000
4 Beds ⋅ 2 Baths ⋅ 2029170 MLS ⋅ CLOSED Status
Charming 4-bedroom, 2-story home in the heart of the Westmorland neighborhood filled with beautiful natural light and thoughtful updates throughout. The bright living room features a wood-burning fireplace and bay windows, while the remodeled kitchen boasts brand-new appliances, cherry cabinetry, a floating island, and tile flooring. Enjoy the dining area with French doors leading to a four-season sunroom (currently used as a playroom) and a main bathroom with whirlpool tub. Major updates include fresh interior paint (2021), renovated and newly insulated attached garage (2021), new water heater (2025), and roof and A/C (2017). The legal fourth bedroom upstairs has been recently refinished and is currently used as a den/office. Relax in the backyard oasis with mature landscaping, brick patio, and covered garden shed. Steps from a direct path to Westmorland Park! Walk to ice cream, coffee, library or hop on the SW bike path for a quick commute to DT and Campus! Walk to Elementary school

560 Toepfer Ave, Madison
460 Glenway St, Madison
$643,000
3 Beds ⋅ 2 Baths ⋅ 2009913 MLS ⋅ CLOSED Status
Endless charm awaits in this classic 3 bed Cape Cod in the most desirable Westmorland! Step inside to find gorgeous hardwoods leading you through the living rm w/ cozy gas fp & stunning views to golf course directly across the street! Sleek updated kitchen w/ granite counters, SS apps, ceramic tile flooring & window to your formal dining w/ walkout to deck. Main lvl also boasts a spacious bedroom w/ private en-suite bath perfect for the option of single-story living. Upstairs find 2 add’l beds & full bath w/ tile shower/tub. Outside enjoy dinners on your back deck overlooking the fenced in yard w/ dog run & custom shed. Plus 1 car attached garage, walking distance to bike path, mins to Downtown & so many thoughtful updates (‘21 AC/Furnace, ‘24 water heater & more) See docs for more info!

460 Glenway St, Madison
509 Westmorland Blvd, Madison
$596,000
3 Beds ⋅ 3 Baths ⋅ 2007454 MLS ⋅ CLOSED Status
Timeless charm meets modern comfort in this beautifully maintained 3 bed, 2.5 bath Cape Cod nestled in the heart of Westmorland. Original hardwood trim, gleaming floors and graceful arched doorway are a few of the things that highlight the home’s character and warmth. The spacious upper-level primary suite offers privacy and a full bath, while a convenient half bath in one of the main floor bedrooms provides ideal flexibility for guests or a home office. Thoughtful updates include brand new siding, epoxy-coated basement floor and fresh interior paint. A rare find in this sought-after neighborhood–an attached 2-car garage adds convenience, value and ease of everyday living.

509 Westmorland Blvd, Madison
4125 Meyer Ave, Madison
$580,305
3 Beds ⋅ 3 Baths ⋅ 2015583 MLS ⋅ CLOSED Status
Discover this delightful Westmorland home at 4125 Meyer Avenue in Madison! This charming property features an attached garage and a partially finished lower level; perfect for flexible living space, a home office, or added storage. A rare highlight for this neighborhood, the property offers two off-street parking spaces that comfortably fit full-sized vehicles. The spacious backyard provides plenty of room to relax or entertain, while the adaptable floor plan suits a variety of lifestyles. The home is in great overall condition and presents an excellent opportunity for cosmetic updates to enhance value. Enjoy living in a vibrant neighborhood close to parks, dining, and everyday conveniences.

4125 Meyer Ave, Madison
3917 Mineral Point Rd, Madison
$580,000
3 Beds ⋅ 3 Baths ⋅ 2012171 MLS ⋅ CLOSED Status
Charming Cape Cod in Madison’s sought-after Westmorland neighborhood! This beautifully updated home features wood floors, stainless steel appliances, and a new gas fireplace for cozy living. With three full baths and a serene primary suite that feels like a private oasis, comfort meets style throughout. Enjoy a two-car detached garage (potential ADU), convenient turnaround driveway, and peaceful outdoor space. Ideally located near Glenway Golf Course, Hilldale, and bike paths—offering easy access to recreation, shopping, and dining. A perfect blend of character, location, and modern updates—welcome home to 3917 Mineral Point Road!

3917 Mineral Point Rd, Madison
3918 St Clair St, Madison
$575,000
4 Beds ⋅ 2 Baths ⋅ 2010350 MLS ⋅ CLOSED Status
Welcome to Westmorland! This meticulously cared for 4 bed, 2 bath home has been thoughtfully remodeled with attention to every detail. Beautifully updated kitchen & bathrooms, remodeled lower level, and new windows throughout. Hardwood floors and abundant natural light create a warm, inviting atmosphere. Relax on the charming covered front porch, entertain on the patio, or reap the rewards of the surrounding garden beds (there's more space than you might think!) The spacious 2.5 car garage offers ample storage and convenience. Friendly neighbors & an annual block party! Just 1 block to Westmorland Park, the SW Commuter Bike Trail, Glen Golf Park, the Arboretum, Monroe St, UW campus, & hospitals. Easy access to a variety of shopping, cafes, pubs, restaurants, & schools!

3918 St Clair St, Madison
429 S Midvale Blvd, Madison
$550,000
3 Beds ⋅ 2 Baths ⋅ 2020336 MLS ⋅ CLOSED Status
Westmorland classic! Don’t miss your chance to see this meticulously maintained 3 bed 2 bath in one of Madison’s most coveted neighborhoods. This corner lot home has been thoughtfully updated and modernized, including all brand-new exterior doors, newly refinished hardwood floors, and fresh paint throughout. The backyard has been fully revamped with a brand-new composite deck and enclosed with a new vinyl fence, perfect for enjoying a private outdoor space. The lower level features an expansive finished space that easily flexes as a home office, workout area, playroom, or TV lounge. The home's best room, the sun porch, features vintage windows and updated flooring, perfect for relaxing or enjoying a meal. Located in a walkable neighborhood with parks, local eateries, and coffee shops, this home offers a strong sense of community in an unbeatable location.

429 S Midvale Blvd, Madison
4013 Meyer Ave, Madison
$535,500
4 Beds ⋅ 3 Baths ⋅ 2001530 MLS ⋅ CLOSED Status
This 4 bed, 3 bath multi-level 2-story is like an adult jungle gym—in the best way! Three beds and a full bath on the main level, plus a big open kitchen and dining area with views of your private backyard. Step down into the living room that opens to a patio, fenced yard, deck, and the ultimate she-shed studio! Upstairs, the primary suite is a retreat all its own with a flex space for lounging or working, a reading nook in the trees, and a newly remodeled bath with stand-up shower, tiled floor, and new vanity. Electric fireplace included in the primary bedroom! Bonus: the lower level has a full bath and space for your gym and workshop! UHP Ultimate Home Warranty for peace!

4013 Meyer Ave, Madison
4306 Rolla Ln, Madison
$519,000
4 Beds ⋅ 3 Baths ⋅ 2010129 MLS ⋅ CLOSED Status
Ranch home with 30-year roof placed in 2006. Solar Panels installed December 2011. Large Living Room and Dining Rooms with hardwood floors and 2-way wood burning fireplace. Main bath with double sinks. 4 bedrooms including one in the basement with a Scapewell window and 3/4 bathroom added in 2005. Hardwood floors also in the 3 bedrooms on the main floor; 2 bedrooms with built-in drawers. Fenced-in back yard.

4306 Rolla Ln, Madison
4017 Meyer Ave, Madison
$513,250
4 Beds ⋅ 2 Baths ⋅ 2028878 MLS ⋅ CLOSED Status
Welcome home to one of Madison's most sought-after neighborhoods! This charming bungalow blends timeless character with today's must-have updates. Gleaming hardwood floors, wood-burning fireplace, beautiful built-ins, and skylights creating an inviting atmosphere filled with natural light. Kitchen features granite countertops, SS appliances & gas range. The Showstopper is the incredible Screened Porch—your favorite spot for morning coffee, summer dinners, or relaxing with friends. Enjoy a spacious yard! Large 1 car gar. New Rubber Roof on main part of the house in '26. Upper Bdrm features patio doors leading to small deck! New FP in '23. House painted in '21. Full basement offers extra storage! Unbeatable location just minutes from parks, UW, top-rated schools, recreation, Hilldale Shopping, grocery, coffee shops, and some of Madison's best restaurants. A rare opportunity to own a classic home in! The perfect blend of timeless character and modern convenience awaits.

4017 Meyer Ave, Madison
4202 St Clair St, Madison
$460,000
2 Beds ⋅ 1 Baths ⋅ 2033733 MLS ⋅ CLOSED Status
FSBO Sold Comp

4202 St Clair St, Madison
3902 Winnemac Ave, Madison
$400,000
3 Beds ⋅ 1 Baths ⋅ 2029790 MLS ⋅ CLOSED Status
Rare opportunity in Westmorland on Madison’s near west side! Set on an expansive .25 acre (90x120) lot, this property offers flexibility for renovation or a future rebuild. Enjoy a prime, walkable and bike-friendly location near Westmorland Park, the Southwest Commuter Path, Trader Joe’s, coffee shops, restaurants, the library, farmers market, wooded trails, and The Glen Golf Park. You’ll be minutes from UW Hospital, the UW-Madison campus, and Camp Randall Stadium. Municipal street improvements by the City of Madison are projected for 2028.

3902 Winnemac Ave, Madison
3901 Meyer Ave, Madison
$370,000
3 Beds ⋅ 2 Baths ⋅ 2008631 MLS ⋅ CLOSED Status
This charming Cape Cod situated in the convenient Westmorland neighborhood near the Glen Golf Course/Park, bike path, bus routes, Sequoya Library and vibrant Monroe St, is ready for new owners after 70+ years of family ownership and your vision for updating. The home features wood floors in the living and bedrooms, arched doorways and a large family/dining room addition with fireplace. A screened porch overlooks the deep backyard ready for your gardening and landscaping. Note that the attached garage has no direct access to inside the home and the basement has a bathroom ready for updating, but no other finished areas at this time with assessor noting a former 300 sq ft basement rec room that was removed for a clean start. Priced below assessed value. Listing Agent related to Seller.

3901 Meyer Ave, Madison

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.