411

Glen Oak Hills Homes

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  • /44

    $500,000

    • 3 Beds
    • 2 Baths
    • 1,736 Sq Ft

    5325 Oak Crest Place, Madison, WI 53705

    Nestled at the end of a peaceful cul-de-sac, this move-in ready home offers comfort, charm & functional updates in all the right places. Step inside to an updated main level featuring a refreshed kitchen/bath, hardwood floors & a spacious owner’s suite w/dbl closets. Downstairs, enjoy a finished LL w/additional full bath, cozy family room & a bonus office or den — easily transformed into a 4th

    Katie Schmitz The Hub Realty

    5325 Oak Crest Place, Madison, WI 53705
  • /18

    $1,550 - $2,575 per month

    The Whitney Reserve

    Studio-2 Beds

    5201 Old Middleton Rd, Madison, WI 53705

    Welcome to The Whitney Reserve. Conveniently located at the stoplight corner of Whitney Way and Old Middleton Road, The Whitney Reserve provides immediate access to all the amenities on Madison’s west side. This upscale 49-unit apartment development has been meticulously integrated into the wooded Glen Oak Hills neighborhood. Step inside and a truly elevated lifestyle welcomes you with

    5201 Old Middleton Rd, Madison, WI 53705
  • /45

    $365,000 Sold Jul 08, 2025

    • 1,137 Sq Ft
    • $321/SF
    • 5 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1958

    1 Mark Twain St, Madison, WI 53705

    Deep in the heart of the best part of the west side lies this quiet 3 bedroom home a short distance to parks, to shopping, to nightlife, to churches, to schools, to work and play. Outside the large open lot is a gardeners delight, just begging to be filled with fruits and vegetables and flowers. Inside there is a an open floor plan, smart use of space, with big windows, lots of light, and new

    Vivienne Andersen Restaino & Associates

    1 Mark Twain St, Madison, WI 53705
    • /27

      Est $376,834 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,376 Sq Ft

      1 Merrill Crest Dr, Madison, WI 53705

      1 Merrill Crest Dr, Madison, WI 53705
  • /38

    $430,000 Pending

    • 2 Beds
    • 2 Baths
    • 1,298 Sq Ft

    401 Merrill Crest Dr, Madison, WI 53705

    SHOWINGS begin Friday after 3PM. This beautifully maintained home offers an ideal blend of indoor comfort & outdoor charm. Inside, the open-concept kitchen and dining area is perfect for everyday living & entertaining. Featuring great flow, natural light, & space to gather. Downstairs, a finished basement room offers flexible space & a cool get away space in the summer. Step outside & fall in

    Christopher Feneis Keller Williams Lake Country

    401 Merrill Crest Dr, Madison, WI 53705
  • /14

    $1,370 per month

    • 2 Beds
    • 1 Bath
    • 780 Sq Ft
    • Apartment for Rent

    5317 Old Middleton Rd Unit "A", Madison, WI 53705

    SHOWING START June 14th - Second Floor Apartment - Freshly painted 2 bedroom unit - LVP flooring throughout - Updated windows - Off street parking - NEW coin laundry in building - Walking distance to Hilldale Mall - Close to bus stop - Close to Glen Oak Hills Park - Close to UW Campus and UW Hospital - Dog friendly (additional fee) - Heat, water, sewer and trash INCLUDED in rent -

    Troy Eickhoff Howard and Williams, INC.-Mdltn

    5317 Old Middleton Rd Unit "A", Madison, WI 53705
  • /63

    $555,000 Sold Apr 10, 2025

    • 1,348 Sq Ft
    • $412/SF
    • 46 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1935

    425 Merrill Crest Dr, Madison, WI 53705

    Delightful Cape Cod home offers charm, convenience + spacious lot in prime location close UW Hospital, downtown + Hilldale Shopping Center. Well-maintained property w/many recent updates including newer roof, dormers + gutters, electrical panel, basement plumbing, insulation, AC, + more! Adorable kitchen features beautiful maple cabinetry. Hardwood floors extend thru living + dining rooms,

    Chas Martin Sprinkman Real Estate

    425 Merrill Crest Dr, Madison, WI 53705
    • /45

      Est $740,521 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,582 Sq Ft

      406 Glen Hwy, Madison, WI 53705

      406 Glen Hwy, Madison, WI 53705
  • /54

    $450,000 Under Contract

    • 4 Beds
    • 2 Baths
    • 1,344 Sq Ft

    5425 Gettle Ave, Madison, WI 53705

    Modern luxury with all the classic charm still intact near the UW Hospital! This move in ready gem has so many great features. The bright and sunny main floor has beautiful original hardwood floors, as well as an updated bathroom and dining area. The elegantly remodeled and spacious kitchen offers solid surface countertops, tile backsplash and wood floors. Downstairs is your private ensuite

    Joe Copeland Realty Executives Cooper Spransy

    5425 Gettle Ave, Madison, WI 53705
  • /15

    $410,000 Sold Mar 11, 2025

    • 1,067 Sq Ft
    • $384/SF
    • 4 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1964

    5434 Gettle Ave, Madison, WI 53705

    This sunny & bright all brick 3 bedroom home featuring beautiful hardwood floors, all new interior paint, new ceiling fans, updated bathroom, eat-in kitchen with Silestone solid surface countertops, pantry w/ pull out drawers, gas range & charming breakfast nook w/ custom built-in storage. The spacious LL offers an opportunity for future expansion, laundry, & lots of storage! Sit out in your

    Rachael See Compass Real Estate Wisconsin

    5434 Gettle Ave, Madison, WI 53705
    • /24

      Est $482,014 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,347 Sq Ft

      5518 Belin St, Madison, WI 53705

      5518 Belin St, Madison, WI 53705
  • /28

    $349,900

    • 2 Beds
    • 1 Bath
    • 775 Sq Ft

    5450 Gettle Ave, Madison, WI 53705

    Stop paying Rent - Own your Future! This well-maintained, one owner home is a rare find in the desirable Glen Oaks Hills neighborhood on Madison's west side. Move in ready and full of potential, the clean / dry basement offers the opportunity to add extra living space to fit your lifestyle. Situated on a spacious lot with room to build a garage or create your dream backyard oasis. Whether you're

    Brandon Mortenson Preferred Realty Group

    5450 Gettle Ave, Madison, WI 53705
  • /21

    $255,000 Sold Jan 27, 2025

    • 815 Sq Ft
    • $313/SF
    • 7 Days On Market
    • Built 1923

    5421 Gettle Ave Unit 1, Madison, WI 53705

    2 unit rental property located off Old Middleton Road just 2 miles from UW Hospital and 5 miles from downtown Madison. Unit #1 is 465 sq.ft with 2 bedrooms, 1 full bath, kitchen area and leased out at $1,145/month. Unit #2 is 350 sq.ft with 1 bedroom, 1 full bath, kitchen area and leased out at $925/month. There is a detached 1 car garage, a large fenced in backyard, laundry hookups onsite, 2

    James Stopple Madison Property Management, Inc.

    5421 Gettle Ave Unit 1, Madison, WI 53705
    • /25

      Est $376,709 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,071 Sq Ft

      305 N Rosa Rd, Madison, WI 53705

      305 N Rosa Rd, Madison, WI 53705
  • /29

    $375,000

    • 3 Beds
    • 1 Bath
    • 1,152 Sq Ft

    5529 Belin St, Madison, WI 53705

    Beautifully updated 3-bedroom ranch with an detached 2-car garage and a full, unfinished basement—ready for your future expansion or storage needs. The spacious kitchen offers abundant cabinetry and room to gather. Nestled on a corner lot, the home features a low-maintenance backyard with a quiet brick patio—perfect for relaxing or entertaining. Enjoy an unbeatable location within walking

    Seth Pfaehler The McGrady Group, LLC

    5529 Belin St, Madison, WI 53705
  • /36

    $365,000 Sold Dec 23, 2024

    • 1,280 Sq Ft
    • $285/SF
    • 149 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1957

    426 Oak Crest Ave, Madison, WI 53705

    Discover the potential in this beloved 1950s 3-bedroom, 1-bath ranch in one of Madison's most sought-after locations! Situated on a generous lot near UW Hospital, downtown, and Hilldale Shopping Center, this property offers unmatched convenience and opportunity. Whether you're ready to roll up your sleeves for a renovation or envision building something new, the possibilities are endless. A prime

    Oi Kommavang First Weber, Inc

    426 Oak Crest Ave, Madison, WI 53705
    • /36

      Est $450,011 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,713 Sq Ft

      14 Glen Hwy, Madison, WI 53705

      14 Glen Hwy, Madison, WI 53705
  • /40

    $474,900

    • 3 Beds
    • 1 Bath
    • 1,501 Sq Ft

    5410 Park Way, Madison, WI 53705

    Welcome home! Tucked into a peaceful subdivision, this unique 3 bedroom two-story home offers charm and serenity nestled in a parklike setting . Surrounded by mature trees, it feels like a retreat while being just moments away from shopping, dining, public transit and popular walking and biking trails. Inside you will find inviting cozy living spaces. Should you be enjoying your morning coffee on

    Kristin Vomhof Realty Executives Capital City

    5410 Park Way, Madison, WI 53705
  • /36

    $376,600 Sold Dec 04, 2024

    • 1,462 Sq Ft
    • $258/SF
    • 5 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1954

    5349 Frosty Ln, Madison, WI 53705

    Discover timeless charm in this adorable 1950's ranch nestled close to the UW campus, hospitals, and the bustling Hilldale Mall. This 2-bedroom home features an additional office space, complete with a sliding door that fills the room with natural light and provides easy access to the fenced backyard. With classic hardwood floors throughout, a thoughtfully designed layout, and a cozy, single

    Christine McCorvie First Weber Inc

    5349 Frosty Ln, Madison, WI 53705
    • /22

      Est $349,270 Not Listed For Sale

      • 1 Bed
      • 1 Bath
      • 616 Sq Ft

      5402 Park Way, Madison, WI 53705

      5402 Park Way, Madison, WI 53705
  • /37

    $420,000

    • 3 Beds
    • 2 Baths
    • 1,328 Sq Ft

    5449 Old Middleton Rd, Madison, WI 53705

    Seller is offering a Basic Home Warranty with the purchase of this delightful 3-bedroom, 2-bath home featuring 1,088 sq ft above grade and an additional 240 sq ft of finished space below. The walkout lower level opens to a fully fenced, landscaped backyard complete with an 8' x 11' powered shed—perfect for storage, hobbies, or a small workshop. Enjoy the screened-in porch year-round, equipped

    Kevin Grinvalsky Rodina Real Estate LLC

    5449 Old Middleton Rd, Madison, WI 53705
  • /37

    $380,000 Sold Oct 24, 2024

    • 1,316 Sq Ft
    • $289/SF
    • 8 Days On Market
    • 4 Beds
    • 1 Bath
    • Built 1957

    26 Wakeman St, Madison, WI 53705

    Show 9/11. Nestled in the desirable Glen Oak Hills neighborhood on Madison’s west side, this delightful & well-maintained ranch-style home is what you’ve been waiting for. You’ll love the open floor plan, hardwood floors throughout, spacious living room & kitchen, plentiful windows, loads of natural light, oversized pantry and fenced backyard. Recent updates include: roof (2017) with a 50-year

    Alise Wasserburger Realty Executives Cooper Spransy

    26 Wakeman St, Madison, WI 53705
    • /60

      Est $353,908 Not Listed For Sale

      • 1 Bed
      • 1 Bath
      • 928 Sq Ft

      5405 Shaw Ct, Madison, WI 53705

      5405 Shaw Ct, Madison, WI 53705
  • /15

    $455,000 Under Contract

    • 3 Beds
    • 1 Bath
    • 1,386 Sq Ft

    5526 Terre Haute Ave, Madison, WI 53705

    This beautifully remodeled 3-bedroom, 1-bath home offers modern updates with classic charm. The brand-new kitchen opens to a cozy enclosed porch, perfect for morning coffee or evening relaxation. Hardwood flooring flows throughout, complementing the home's bright and inviting atmosphere. Enjoy peace of mind with newer windows and a well-maintained exterior. The expansive yard provides ample space

    Denise Holmes Bunbury & Assoc, REALTORS

    5526 Terre Haute Ave, Madison, WI 53705
  • /48

    $520,000 Sold Aug 28, 2024

    • 1,682 Sq Ft
    • $309/SF
    • 48 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1963

    101 N Kenosha Dr, Madison, WI 53705

    Welcome home!!! This well-maintained, mid-century home is calling! This lovely abode has only had two owners in its lifetime and is located in a prime near west location, close to Hilldale, UW Hospital, restaurants, shopping and walking/biking trails. It has a cool, easy flow and boasts a gorgeous fireplace, loads of natural light, spacious room sizes, a huge yard, lots of storage and overlooks

    Sue Janowitsch Restaino & Associates

    101 N Kenosha Dr, Madison, WI 53705
    • /39

      Est $394,772 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 996 Sq Ft

      405 Hilldale Ct, Madison, WI 53705

      405 Hilldale Ct, Madison, WI 53705
  • /45

    $380,000 Sold Aug 15, 2024

    • 1,094 Sq Ft
    • $347/SF
    • 4 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1951

    413 Merrill Crest Dr, Madison, WI 53705

    Location, location, location! Charming 1951 bungalow on .38 acre lot in sought-after 53705! Features include 3BR/2BA, formal LR/DR, screen porch, hdwd flrs, archways, built-ins, newer furnace, central AC + newer deck! Freshly repainted interior & new fans/lighting throughout, new doorknobs & all new switches/outlets! Charming breeseway & attached garage w/attic access. Huge bsmt w/ample storage

    Jolenta Averill Lake & City Homes Realty

    413 Merrill Crest Dr, Madison, WI 53705
    • /29

      Est $391,439 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,035 Sq Ft

      413 Hilldale Ct, Madison, WI 53705

      413 Hilldale Ct, Madison, WI 53705
  • /2

    $280,000 Sold Jul 11, 2025

    • 700 Sq Ft
    • $400/SF
    • 0 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1955

    6 Mark Twain St, Madison, WI 53705

    sold comp

    Matt Winzenried Realty Executives Cooper Spransy

    6 Mark Twain St, Madison, WI 53705
    • /21

      Est $456,428 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,462 Sq Ft

      417 Hilldale Ct, Madison, WI 53705

      417 Hilldale Ct, Madison, WI 53705
  • /2

    $450,000 Sold Aug 16, 2024

    • 1,589 Sq Ft
    • $283/SF
    • 3 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1950

    5376 Park Way, Madison, WI 53705

    Sold Comp

    Pat Powers Restaino & Associates

    5376 Park Way, Madison, WI 53705
    • /54

      Est $355,599 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 912 Sq Ft

      501 Hilldale Ct, Madison, WI 53705

      501 Hilldale Ct, Madison, WI 53705
    • /25

      Est $336,312 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 788 Sq Ft

      509 Hilldale Ct, Madison, WI 53705

      509 Hilldale Ct, Madison, WI 53705
    • /30

      Est $372,871 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,260 Sq Ft

      410 Hilldale Ct, Madison, WI 53705

      410 Hilldale Ct, Madison, WI 53705
    • /39

      Est $316,718 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 672 Sq Ft

      5522 Gettle Ave, Madison, WI 53705

      5522 Gettle Ave, Madison, WI 53705
    • /27

      Est $378,144 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 785 Sq Ft

      10 Merrill Crest Dr, Madison, WI 53705

      10 Merrill Crest Dr, Madison, WI 53705
    • /32

      Est $605,158 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,968 Sq Ft

      17 N Kenosha Dr, Madison, WI 53705

      17 N Kenosha Dr, Madison, WI 53705
    • /50

      Est $533,793 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,722 Sq Ft

      109 N Kenosha Dr, Madison, WI 53705

      109 N Kenosha Dr, Madison, WI 53705
    • /45

      Est $479,780 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,518 Sq Ft

      414 Merrill Crest Dr, Madison, WI 53705

      414 Merrill Crest Dr, Madison, WI 53705
    • /34

      Est $394,818 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 869 Sq Ft

      5307 Frosty Ln, Madison, WI 53705

      5307 Frosty Ln, Madison, WI 53705

Showing Results 1 - 40, Page 1 of 11

Home Trends in Glen Oak Hills, WI

Housing Trends

Median Sale Price
$550,000
Number of Homes for Sale
0
Last 12 months Home Sales
1
Months of Supply
0.00
Median List Price
$549,900
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
87%
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