Glen Oak Hills Homes

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  /44

  $500,000 Pending

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

  5325 Oak Crest Place, Madison, WI 53705

  NO OPEN HOUSE 8/3 - ACCEPTED OFFER! 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

  Katie Schmitz The Hub Realty

  5325 Oak Crest Place, Madison, WI 53705
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  Explore Glen Oak Hills

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  /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
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  /29

  $375,000 Sold Aug 29, 2025

  • 1,152 Sq Ft
  • $326/SF
  • 29 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1971

  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
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  /45

  Est $737,493 Not Listed For Sale

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

  406 Glen Hwy, Madison, WI 53705

  406 Glen Hwy, Madison, WI 53705
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  /38

  $399,900 Under Contract

  • 4 Beds
  • 1 Bath
  • 1,310 Sq Ft

  5521 Gettle Ave, Madison, WI 53705

  Showings start 9/5. Welcoming bungalow close to Madison's Hilldale area and west side! Bold maple floors on main level and thoughtful details create a warm, inviting feel. You'll love the gorgeous exposed brick chimney! 2 bedrooms on main level, plus two additional up! The sunroom flows to a private fenced yard with beautiful landscaping and patio—ideal for relaxing or entertaining! An oversized

  Jason Fowler Century 21 Affiliated

  5521 Gettle Ave, Madison, WI 53705
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  /15

  $1,550 per month

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

  5317 Old Middleton Rd Unit C, Madison, WI 53705

  AVAILABLE NOW!!!: First-floor unit with walk-out to parking lot. Clean 2-bedroom apartment featuring a updated bathroom with a spacious shower, LVP flooring throughout and updated windows. Off-street parking at no extra cost (1 space per unit). New coin laundry available in building. Conveniently located near bus stop and within walking distance to Hilldale Mall, Glen Oak Hills Park, and

  Troy Eickhoff Howard and Williams, INC.-Mdltn

  5317 Old Middleton Rd Unit C, Madison, WI 53705
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  /38

  $475,000 Sold Aug 22, 2025

  • 1,298 Sq Ft
  • $366/SF
  • 3 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1952

  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
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  /24

  Est $484,653 Not Listed For Sale

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

  5518 Belin St, Madison, WI 53705

  5518 Belin St, Madison, WI 53705
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  /25

  $450,000

  • 6 Beds
  • 2 Baths
  • 1,777 Sq Ft

  5517 Terre Haute Ave, Madison, WI 53705

  In the heart of Madison’s west side, just steps from Glen Oak Hills Park and Owen Conservation Park, this home offers space, character, and endless opportunity. Minutes from Hilldale, Middleton, and a short drive downtown, the location is hard to beat. Inside, you’ll find 6 spacious bedrooms, with hardwood floors in the main level ones, along with timeless details like built-in shelves, cabinets,

  Mari Slobounov Keller Williams Realty

  5517 Terre Haute Ave, Madison, WI 53705
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  /16

  $1,500 per month

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft
  • Condo for Rent

  5317 Old Middleton Rd Unit 1, Madison, WI 53705

  Property Id: 2112426Apartment available to sublease/lease takeover for October 1st-July 31 (option to move-in as soon as September 5 if desired!) Option to renew the lease! Apartment location in Madison, close to Hilldale Mall , provides easy access to bus routes, the beltline highway, UW Madison and Madison College Campuses.Very sad to leave this apartment. Management is fantastic.Water,

  5317 Old Middleton Rd Unit 1, Madison, WI 53705
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  /54

  $440,000 Sold Aug 18, 2025

  • 1,344 Sq Ft
  • $327/SF
  • 71 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1916

  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
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  /25

  Est $384,277 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
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  /35

  $549,900

  • 4 Beds
  • 4 Baths
  • 2,293 Sq Ft

  5422 Gettle Ave, Madison, WI 53705

  Spacious one-owner home on Madison's West Side - Meticulously maintained by the original owner, this spacious home in the desirable Glen Oaks neighborhood offers comfort, flexibility and a prime location. Featuring 4 bds / 2 full baths and 2 half baths, a large main level bonus room/office space, there's room for everyone and everything. The partially finished basement provides additional space

  Brandon Mortenson Preferred Realty Group

  5422 Gettle Ave, Madison, WI 53705
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  /14

  $1,460 per month

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

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

  Available NOW is this cozy 2 bedroom apartment with a ground level private entry. 1 bedroom would work excellent as an office if you choose. Sign by Sept 1st, get December rent at 1/2 price! - Freshly painted throughout - LVP flooring throughout - Updated windows - NEW coin laundry in building - Close to bus stop, Hilldale Mall, Glen Oak Hills Park, UW Campus and UW Hospital - Dog friendly

  Troy Eickhoff Howard and Williams, INC.-Mdltn

  5317 Old Middleton Rd Unit "A", Madison, WI 53705
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  /15

  $455,000 Sold Aug 01, 2025

  • 1,386 Sq Ft
  • $328/SF
  • 4 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1954

  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
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  /36

  Est $465,337 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,713 Sq Ft

  14 Glen Hwy, Madison, WI 53705

  14 Glen Hwy, Madison, WI 53705
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  /28

  $319,900

  • 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
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  /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
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  /60

  Est $358,392 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 928 Sq Ft

  5405 Shaw Ct, Madison, WI 53705

  5405 Shaw Ct, Madison, WI 53705
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  /58

  $399,000

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

  5449 Old Middleton Rd, Madison, WI 53705

  West Side Comfort with Private Backyard Retreat. Discover charm and convenience in this move-in ready 3BR/2BA ranch, perfectly situated on Madison’s west side just minutes from Hilldale, parks, bus lines, and the UW campus. Enjoy peaceful mornings or summer evenings in the screened-in porch with marine-grade roll-up weather shades, overlooking a fully fenced, landscaped yard. The walkout lower

  Kevin Grinvalsky Rodina Real Estate LLC

  5449 Old Middleton Rd, Madison, WI 53705
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  /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
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  /39

  Est $402,137 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 996 Sq Ft

  405 Hilldale Ct, Madison, WI 53705

  405 Hilldale Ct, Madison, WI 53705
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  /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
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  /29

  Est $391,755 Not Listed For Sale

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

  413 Hilldale Ct, Madison, WI 53705

  413 Hilldale Ct, Madison, WI 53705
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  /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
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  /21

  Est $462,003 Not Listed For Sale

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

  417 Hilldale Ct, Madison, WI 53705

  417 Hilldale Ct, Madison, WI 53705
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  /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
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  /54

  Est $360,897 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 912 Sq Ft

  501 Hilldale Ct, Madison, WI 53705

  501 Hilldale Ct, Madison, WI 53705
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  /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
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  /25

  Est $333,289 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 788 Sq Ft

  509 Hilldale Ct, Madison, WI 53705

  509 Hilldale Ct, Madison, WI 53705
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  /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
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  /30

  Est $387,731 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
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  /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
• 

  

  /39

  Est $322,544 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 672 Sq Ft

  5522 Gettle Ave, Madison, WI 53705

  5522 Gettle Ave, Madison, WI 53705
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  /27

  Est $388,516 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
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  /32

  Est $619,018 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
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  /48

  Est $551,011 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,682 Sq Ft

  101 N Kenosha Dr, Madison, WI 53705

  101 N Kenosha Dr, Madison, WI 53705
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  /50

  Est $548,532 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
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  /34

  Est $402,638 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 869 Sq Ft

  5307 Frosty Ln, Madison, WI 53705

  5307 Frosty Ln, Madison, WI 53705
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  /28

  Est $423,617 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,012 Sq Ft

  510 Merrill Crest Dr, Madison, WI 53705

  510 Merrill Crest Dr, Madison, WI 53705

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