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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.

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

$750,000

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!

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

$715,000

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.

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

$710,000

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.

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

$709,000

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!

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

$675,000

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!

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

$645,000

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

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

$550,000

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.

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

$513,250

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.

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

$460,000

FSBO Sold Comp

2 Beds ⋅ 1 Baths ⋅ 2033733 MLS ⋅ CLOSED Status

FSBO Sold Comp

4202 St Clair St, Madison

$400,000

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.

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