Glen Oak Hills Homes

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  /65

  $362,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,317 Sq Ft

  5449 Old Middleton Rd, Madison, WI 53705

  Make 53705 your new zip code! Voted 1 of the top zip codes in Madison! The main floor, freshly painted ceilings/rooms. Relax, this home comes w/14 month Home Warranty & is ready for its new owner! When entering through front door, hardwood floor from TN greet you in the Living R w/gas fireplace. This home has several places to retreat to. Spacious screened porch w/skylight & marine-grade, roll-up

  Kelly Gilboy Restaino & Associates

  5449 Old Middleton Rd, Madison, WI 53705
• 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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  /45

  $365,000 Sold Jul 08, 2025

  1 Mark Twain St, Madison, WI 53705

  • 3 Beds
  • 1 Bath
  • 1,137 Sq Ft
  • Built 1958

  Last Sold Summary

  • 12% Above List Price
  • $321/SF
  • 5 Days On Market

  Current Estimated Value $364,375

  Last Listing Agent Vivienne Andersen Restaino & Associates

  1 Mark Twain St, Madison, WI 53705
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  /36

  Est $389,726 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,280 Sq Ft

  426 Oak Crest Ave, Madison, WI 53705

  426 Oak Crest Ave, Madison, WI 53705
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  /34

  $524,900

  • 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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  /15

  $1,300 per month

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

  5317 Old Middleton Rd Unit C, Madison, WI 53705

  AVAILABLE NOW is this clean 2-bedroom apartment with private entry features a updated bathroom with a spacious shower, LVP flooring throughout and updated windows. Off-street parking INCLUDED in rent (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 eateries. Close to UW Hospital

  Troy Eickhoff Howard and Williams, INC.-Mdltn

  5317 Old Middleton Rd Unit C, Madison, WI 53705
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  $480,000 Sold Sep 10, 2025

  5325 Oak Crest Place, Madison, WI 53705

  • 3 Beds
  • 2 Baths
  • 1,736 Sq Ft
  • Built 1956

  Last Sold Summary

  • 4% Below List Price
  • $276/SF
  • 39 Days On Market

  Current Estimated Value $482,215

  Last Listing Agent The Hub Team The Hub Realty

  5325 Oak Crest Place, Madison, WI 53705
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  /45

  Est $667,364 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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  /90

  $450,000

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

  401 Merrill Crest Dr, Madison, WI 53705

  Explore this beautifully renovated home in Glen Oak Hills! The interior showcases fresh paint, modern lighting, and updated appliances. An open kitchen and dining area bathe in natural light, creating a warm, inviting atmosphere. The finished lower level offers flexible living space and an additional bathroom. Step outside to a spacious, fenced backyard featuring a storage shed, two patios, and

  Jenny Bunbury-Johnson Bunbury & Assoc, REALTORS

  401 Merrill Crest Dr, Madison, WI 53705
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  /14

  $1,295 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. - 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 (additional fee) - Heat, water, sewer and trash and 1

  Troy Eickhoff Howard and Williams, INC.-Mdltn

  5317 Old Middleton Rd Unit "A", Madison, WI 53705
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  $305,000 Sold Dec 01, 2025

  5450 Gettle Ave, Madison, WI 53705

  • 2 Beds
  • 1 Bath
  • 775 Sq Ft
  • Built 1958

  Last Sold Summary

  • 13% Below List Price
  • $394/SF
  • 113 Days On Market

  Last Listing Agent Brandon Mortenson Preferred Realty Group

  5450 Gettle Ave, Madison, WI 53705
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  /24

  Est $482,131 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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  /15

  $410,000 Sold Mar 11, 2025

  5434 Gettle Ave, Madison, WI 53705

  • 3 Beds
  • 1 Bath
  • 1,067 Sq Ft
  • Built 1964

  Last Sold Summary

  • 6% Above List Price
  • $384/SF
  • 4 Days On Market

  Current Estimated Value $410,504

  Last Listing Agent Rachael See Compass Real Estate Wisconsin

  5434 Gettle Ave, Madison, WI 53705
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  /25

  Est $372,169 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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  $555,000 Sold Apr 10, 2025

  425 Merrill Crest Dr, Madison, WI 53705

  • 3 Beds
  • 2 Baths
  • 1,348 Sq Ft
  • Built 1935

  Last Sold Summary

  • 11% Above List Price
  • $412/SF
  • 46 Days On Market

  Current Estimated Value $533,224

  Last Listing Agent Chas Martin Sprinkman Real Estate

  425 Merrill Crest Dr, Madison, WI 53705
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  /36

  Est $463,349 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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  /20

  $255,000 Sold Jan 27, 2025

  5421 Gettle Ave Unit 1, Madison, WI 53705

  • 3 Beds
  • 2 Baths
  • 1,079 Sq Ft
  • Built 1923

  Last Sold Summary

  • 11% Below List Price
  • $236/SF
  • 7 Days On Market

  Current Estimated Value $269,485

  Last Listing Agent James Stopple Madison Property Management, Inc.

  5421 Gettle Ave Unit 1, Madison, WI 53705
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  /37

  Est $397,702 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 1,316 Sq Ft

  26 Wakeman St, Madison, WI 53705

  26 Wakeman St, Madison, WI 53705
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  /38

  $415,000 Sold Oct 01, 2025

  5521 Gettle Ave, Madison, WI 53705

  • 4 Beds
  • 1 Bath
  • 1,310 Sq Ft
  • Built 1935

  Last Sold Summary

  • 4% Above List Price
  • $317/SF
  • 2 Days On Market

  Last Listing Agent Jason Fowler Century 21 Affiliated

  5521 Gettle Ave, Madison, WI 53705
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  /60

  Est $353,035 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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  $375,000 Sold Aug 29, 2025

  5529 Belin St, Madison, WI 53705

  • 3 Beds
  • 1 Bath
  • 1,152 Sq Ft
  • Built 1971

  Last Sold Summary

  • $326/SF
  • 29 Days On Market

  Current Estimated Value $382,910

  Last Listing Agent Seth Pfaehler The McGrady Group, LLC

  5529 Belin St, Madison, WI 53705
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  /39

  Est $393,244 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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  $440,000 Sold Aug 18, 2025

  5425 Gettle Ave, Madison, WI 53705

  • 4 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 1916

  Last Sold Summary

  • 16% Below List Price
  • $327/SF
  • 71 Days On Market

  Current Estimated Value $437,813

  Last Listing Agent Joe Copeland Realty Executives Cooper Spransy

  5425 Gettle Ave, Madison, WI 53705
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  /29

  Est $387,839 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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  /2

  $280,000 Sold Jul 11, 2025

  6 Mark Twain St, Madison, WI 53705

  • 2 Beds
  • 1 Bath
  • 700 Sq Ft
  • Built 1955

  Last Sold Summary

  • $400/SF
  • 0 Days On Market

  Current Estimated Value $286,177

  Last Listing Agent Matt Winzenried Realty Executives Cooper Spransy

  6 Mark Twain St, Madison, WI 53705
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  /21

  Est $453,676 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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  /15

  $455,000 Sold Aug 01, 2025

  5526 Terre Haute Ave, Madison, WI 53705

  • 3 Beds
  • 1 Bath
  • 1,386 Sq Ft
  • Built 1954

  Last Sold Summary

  • $328/SF
  • 4 Days On Market

  Current Estimated Value $436,513

  Last Listing Agent Denise Holmes Collective Real Estate Group

  5526 Terre Haute Ave, Madison, WI 53705
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  /54

  Est $351,824 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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  /25

  Est $318,912 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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  /30

  Est $384,731 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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  /39

  Est $312,096 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 $383,945 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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  /48

  Est $534,871 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 $524,108 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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  /36

  Est $395,514 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,462 Sq Ft

  5349 Frosty Ln, Madison, WI 53705

  5349 Frosty Ln, Madison, WI 53705
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  /28

  Est $411,333 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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  /64

  Est $462,286 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,916 Sq Ft

  5318 Frosty Ln, Madison, WI 53705

  5318 Frosty Ln, Madison, WI 53705
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  /30

  Est $443,991 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,667 Sq Ft

  5332 Frosty Ln, Madison, WI 53705

  5332 Frosty Ln, Madison, WI 53705
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  /45

  Est $675,838 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,555 Sq Ft

  414 Wynnwood Way, Madison, WI 53705

  414 Wynnwood Way, Madison, WI 53705
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  /42

  Est $508,384 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,478 Sq Ft

  5220 Langlois St, Madison, WI 53705

  5220 Langlois St, Madison, WI 53705

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