Highland, WI Homes

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  /8

  $45,000 Under Contract

  • Land
  • 0.57 Acre
  • $78,947 per Acre

  515 Valley St, Highland, WI 53543

  This lot is just waiting for you to build your dream home. Seller previously dug a hole to confirm this land did not contain rocky soil and found that is has nice black dirt perfect for building site. It measures at .57 acres and is 1 of the only 2 buildable lots available in Highland. Hurry and snatch it up before someone else does.

  Jody Cody Jon Miles Real Estate

  515 Valley St, Highland, WI 53543
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  /18

  $360,000 Sold Oct 17, 2025

  1051 Cardinal Dr, Highland, WI 53543

  • 4 Beds
  • 5 Baths
  • 3,250 Sq Ft
  • Built 2006

  Last Sold Summary

  • 4% Below List Price
  • $111/SF
  • 7 Days On Market

  Current Estimated Value $364,068

  Last Listing Agent Ed Kraisinger RE/MAX Preferred

  1051 Cardinal Dr, Highland, WI 53543
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  /55

  Est $730,753 Not Listed For Sale

  5555 Farmers Ridge Rd, Highland, WI 53543

  • 5 Beds
  • 3 Baths
  • 2,700 Sq Ft

  5555 Farmers Ridge Rd, Highland, WI 53543

  Last Sold Summary

  • 1% Above List Price
  • $269/SF
  • 30 Days On Market

  Last Sold Price $725,000

  Last Listing Agent Jay Frazier Weiss Realty LLC
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  /90

  $279,900

  • 4 Beds
  • 2 Baths
  • 2,204 Sq Ft

  519 Delaney St, Highland, WI 53543

  Wonderful spaces in this 2-story home offering 4 bedrooms, 2 baths, & updates throughout. A spacious foyer welcomes you into the kitchen w/lots of hickory cabinets, a breakfast bar, skylights, & pantries. Open floor plan expands into a huge living/family room w/vaulted ceiling, picture windows, rich oak woodwork, & a handcrafted stone fireplace w/oak mantle. Enjoy the convenience of a main-level

  Kathy Good Bunbury & Assoc, REALTORS

  519 Delaney St, Highland, WI 53543
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  /24

  $38,000 Sold Sep 26, 2025

  11243 19th Ave E, Highland, WI 54849

  • Land
  • 10 Acres
  • $3,800 per Acre

  Last Sold Summary

  • 9% Above List Price
  • 5 Days On Market

  Last Listing Agent Ronald Walters Dane Arthur Real Estate Agency/Birchwood

  11243 19th Ave E, Highland, WI 54849
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  /27

  Est $258,937 Not Listed For Sale

  1787 Pompeys Pillar Rd, Highland, WI 53543

  • 3 Beds
  • 2 Baths
  • 2,015 Sq Ft
  • Built 1936

  1787 Pompeys Pillar Rd, Highland, WI 53543

  Last Sold Summary

  • 4% Below List Price
  • $133/SF
  • 8 Days On Market

  Last Sold Price $269,000

  Last Listing Agent Paul Halberg Wisconsin.Properties Realty, LLC
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  /5

  $40,000 Under Contract

  • Land
  • 0.55 Acre
  • $72,727 per Acre

  525 Horizon St, Highland, WI 53543

  This lot is just waiting for your dream home. It measure at .55 acres and is 1 of the only 2 buildable lots available in Highland. Hurry and snatch it up before someone else does.

  Jody Cody Jon Miles Real Estate

  525 Horizon St, Highland, WI 53543
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  /22

  $160,000 Sold Apr 07, 2025

  530 Delaney St, Highland, WI 53543

  • 3 Beds
  • 1.5 Baths
  • 1,220 Sq Ft

  Last Sold Summary

  • 3% Above List Price
  • $131/SF
  • 2 Days On Market

  Current Estimated Value $161,828

  Last Listing Agent Michelene Fisher Fisher Realty Group, LLC

  530 Delaney St, Highland, WI 53543
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  /77

  Est $510,795 Not Listed For Sale

  4669 State Road 80, Highland, WI 53543

  • 4 Beds
  • 3 Baths
  • 2,924 Sq Ft
  • Built 1900

  4669 State Road 80, Highland, WI 53543

  Last Sold Summary

  • 17% Below List Price
  • $209/SF
  • 98 Days On Market

  Last Sold Price $612,000

  Last Listing Agent Christina Weitzel RE/MAX Preferred
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  /30

  $219,900

  • 2 Beds
  • 1 Bath
  • 1,095 Sq Ft

  517 High St, Highland, WI 53543

  Lovely two bedroom ranch home, well maintained and ready for you to make it your own. Well maintained throughout. Modern touches to the finish details provide a delightful updated living space. Enjoy the comfort and warmth of baseboard hot water heat. Large living room open to dining area and kitchen with lots of cabinets. Bathroom has been updated including a large walk-in shower. The addition

  Jonathan Miles Jon Miles Real Estate

  517 High St, Highland, WI 53543
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  /2

  $37,000 Sold Feb 20, 2026

  0000 19th Ave E, Highland, WI 54849

  • Land
  • 10 Acres
  • $3,700 per Acre

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Sara Haakenson Re/Max 4 Seasons, LLC

  0000 19th Ave E, Highland, WI 54849
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  /27

  Est $192,243 Not Listed For Sale

  242 Dodgeville St, Highland, WI 53543

  • 3 Beds
  • 1.5 Baths
  • 1,288 Sq Ft
  • Built 1967

  242 Dodgeville St, Highland, WI 53543

  Last Sold Summary

  • 3% Above List Price
  • $144/SF
  • 20 Days On Market

  Last Sold Price $186,000

  Last Listing Agent Joe VanMatre EXP Realty, LLC
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  /26

  $515,000 Sold Oct 27, 2025

  445 Busch Rd, Highland, WI 53543

  • Land
  • 68.8 Acres
  • $7,485 per Acre

  Last Sold Summary

  • 2% Below List Price
  • 8 Days On Market

  Last Listing Agent Tyler Wilkinson Wilkinson Auction & Realty Co.

  445 Busch Rd, Highland, WI 53543
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  /15

  Est $168,557 Not Listed For Sale

  1111 Dodgeville St, Highland, WI 53543

  • 3 Beds
  • 2 Baths
  • 2,124 Sq Ft

  1111 Dodgeville St, Highland, WI 53543

  Last Sold Summary

  • 23% Above List Price
  • $65/SF
  • 24 Days On Market

  Last Sold Price $137,000

  Last Listing Agent Bobbi Jo Bomkamp Drone Century 21 Affiliated
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  /2

  $260,000 Sold Aug 01, 2025

  744 Main St, Highland, WI 53543

  • 3 Beds
  • 2 Baths
  • 1,568 Sq Ft

  Last Sold Summary

  • $166/SF
  • 0 Days On Market

  Current Estimated Value $250,910

  Last Listing Agent Michelene Fisher Fisher Realty Group, LLC

  744 Main St, Highland, WI 53543
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  /18

  Est $273,881 Not Listed For Sale

  1270 Dodgeville St, Highland, WI 53543

  • 3 Beds
  • 1.5 Baths
  • 2,480 Sq Ft

  1270 Dodgeville St, Highland, WI 53543

  Last Sold Summary

  • 7% Above List Price
  • $103/SF
  • 46 Days On Market

  Last Sold Price $256,000

  Last Listing Agent Bobbi Jo Bomkamp Drone Century 21 Affiliated
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  /6

  $262,600 Sold Jun 24, 2025

  342 Grand St, Highland, WI 53543

  • 4 Beds
  • 1.5 Baths
  • 1,500 Sq Ft
  • Built 1968

  Last Sold Summary

  • 1% Below List Price
  • $175/SF
  • 0 Days On Market

  Current Estimated Value $271,766

  Last Listing Agent Bobbi Jo Bomkamp Drone Century 21 Affiliated

  342 Grand St, Highland, WI 53543
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  /22

  Est $154,610 Not Listed For Sale

  316 Main St, Highland, WI 53543

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Built 1940

  316 Main St, Highland, WI 53543

  Last Sold Summary

  • 3% Above List Price
  • $125/SF
  • 153 Days On Market

  Last Sold Price $150,000

  Last Listing Agent Ed Kraisinger RE/MAX
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  /13

  $250,000 Sold Aug 13, 2025

  1370 Dodgeville St, Highland, WI 53543

  • 3 Beds
  • 1.5 Baths
  • 1,500 Sq Ft

  Last Sold Summary

  • 3% Below List Price
  • $167/SF
  • 8 Days On Market

  Current Estimated Value $242,781

  Last Listing Agent Bobbi Jo Bomkamp Drone Century 21 Affiliated

  1370 Dodgeville St, Highland, WI 53543
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  /23

  Est $149,833 Not Listed For Sale

  506 Dodgeville St, Highland, WI 53543

  • 2 Beds
  • 1.5 Baths
  • 1,224 Sq Ft
  • Built 1962

  506 Dodgeville St, Highland, WI 53543

  Last Sold Summary

  • 7% Above List Price
  • $114/SF
  • 17 Days On Market

  Last Sold Price $139,900

  Last Listing Agent Risa Topper Realty of America, LLC
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  /11

  $135,000 Sold Mar 26, 2026

  409 Spring St, Highland, WI 53543

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  Last Sold Summary

  • 2% Below List Price
  • $96/SF
  • 40 Days On Market

  Last Listing Agent Bobbi Jo Bomkamp Drone Century 21 Affiliated

  409 Spring St, Highland, WI 53543
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  /24

  Est $179,537 Not Listed For Sale

  511 Dodgeville St, Highland, WI 53543

  • 3 Beds
  • 1.5 Baths
  • 1,152 Sq Ft

  511 Dodgeville St, Highland, WI 53543

  Last Sold Summary

  • 1% Above List Price
  • $155/SF
  • 6 Days On Market

  Last Sold Price $178,000

  Last Listing Agent Risa Topper Realty of America, LLC
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  /15

  $145,000 Sold May 07, 2025

  1231 Dodgeville St, Highland, WI 53543

  • 4 Beds
  • 1.5 Baths
  • 1,760 Sq Ft

  Last Sold Summary

  • 19% Below List Price
  • $82/SF
  • 134 Days On Market

  Current Estimated Value $162,290

  Last Listing Agent Tammy McGuire McGuire Realty Group, LLC

  1231 Dodgeville St, Highland, WI 53543
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  /67

  Est $160,970 Not Listed For Sale

  344 Isabell St, Highland, WI 53543

  • 3 Beds
  • 2 Baths
  • 2,123 Sq Ft
  • Built 1900

  344 Isabell St, Highland, WI 53543

  Last Sold Summary

  • 13% Above List Price
  • $67/SF
  • 7 Days On Market

  Last Sold Price $142,500

  Last Listing Agent Jonathan Miles Jon Miles Real Estate
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  /18

  $170,000 Sold Feb 20, 2026

  904 Dodgeville St, Highland, WI 53543

  • 3 Beds
  • 2 Baths
  • 1,665 Sq Ft

  Last Sold Summary

  • 21% Below List Price
  • $102/SF
  • 80 Days On Market

  Current Estimated Value $172,607

  Last Listing Agent Michelene Fisher Fisher Realty Group, LLC

  904 Dodgeville St, Highland, WI 53543
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  /8

  Est $262,230 Not Listed For Sale

  535 Spring St, Highland, WI 53543

  • 7 Beds
  • 3.5 Baths
  • 3,150 Sq Ft

  535 Spring St, Highland, WI 53543

  Last Sold Summary

  • 11% Above List Price
  • $75/SF
  • 202 Days On Market

  Last Sold Price $237,000

  Last Listing Agent Tammy McGuire McGuire Realty Group, LLC
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  /27

  $198,000 Sold Dec 12, 2025

  916 Diagonal St, Highland, WI 53543

  • 3 Beds
  • 1 Bath
  • 2,100 Sq Ft

  Last Sold Summary

  • 12% Below List Price
  • $94/SF
  • 104 Days On Market

  Current Estimated Value $196,233

  Last Listing Agent Emily Lins RE/MAX Preferred

  916 Diagonal St, Highland, WI 53543
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  /24

  Est $202,979 Not Listed For Sale

  314 Spring St, Highland, WI 53543

  • 3 Beds
  • 2.5 Baths
  • 1,900 Sq Ft
  • Built 1980

  314 Spring St, Highland, WI 53543

  Last Sold Summary

  • 21% Above List Price
  • $88/SF
  • 5 Days On Market

  Last Sold Price $168,000

  Last Listing Agent Michelene Fisher Fisher Realty Group, LLC
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  /44

  $203,000 Sold Jul 11, 2025

  207 Dodgeville St, Highland, WI 53543

  • 1,700 Sq Ft
  • Built 1996

  Last Sold Summary

  • $119/SF
  • 3 Days On Market

  Current Estimated Value $217,254

  Last Listing Agent Kathi Schmidt Keller Williams Realty

  207 Dodgeville St, Highland, WI 53543
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  /21

  Est $185,512 Not Listed For Sale

  504 Spring St, Highland, WI 53543

  • 5 Beds
  • 1 Bath
  • 1,884 Sq Ft

  504 Spring St, Highland, WI 53543

  Last Sold Summary

  • $99/SF
  • 9 Days On Market

  Last Sold Price $185,900

  Last Listing Agent Jacqueline Benish First Weber Inc
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  /32

  $147,000 Sold Jul 14, 2025

  604 Isabell St, Highland, WI 53543

  • 4 Beds
  • 1.5 Baths
  • 1,504 Sq Ft

  Last Sold Summary

  • 1% Below List Price
  • $98/SF
  • 8 Days On Market

  Current Estimated Value $163,454

  Last Listing Agent Heather McNeill Lori Droessler Real Estate, In

  604 Isabell St, Highland, WI 53543
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  /15

  Est $150,456 Not Listed For Sale

  608 Spring St, Highland, WI 53543

  • 2 Beds
  • 1 Bath
  • 1,100 Sq Ft

  608 Spring St, Highland, WI 53543

  Last Sold Summary

  • 23% Above List Price
  • $111/SF
  • 48 Days On Market

  Last Sold Price $122,000

  Last Listing Agent Kim Seifert EXP Realty, LLC
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  /86

  $675,000 Sold Jan 16, 2026

  4700 Hazy Ln, Highland, WI 53543

  • 3 Beds
  • 2 Baths
  • 2,578 Sq Ft
  • Built 1996

  Last Sold Summary

  • 16% Below List Price
  • $262/SF
  • 60 Days On Market

  Current Estimated Value $672,918

  Last Listing Agent Michael Brennan First Weber Inc

  4700 Hazy Ln, Highland, WI 53543
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  /50

  Est $331,957 Not Listed For Sale

  539 Prospect St, Highland, WI 53543

  • 4 Beds
  • 3.5 Baths
  • 3,300 Sq Ft
  • Built 2003

  539 Prospect St, Highland, WI 53543

  Last Sold Summary

  • 1% Above List Price
  • $100/SF
  • 2 Days On Market

  Last Sold Price $330,000

  Last Listing Agent Christina Weitzel RE/MAX Preferred
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  /2

  $245,000 Sold Jun 13, 2025

  1045 E Circle Dr, Highland, WI 53543

  • 4 Beds
  • 3 Baths
  • 1,900 Sq Ft
  • Built 1999

  Last Sold Summary

  • $129/SF
  • 3 Days On Market

  Current Estimated Value $268,522

  Last Listing Agent MHB Real Estate Team MHB Real Estate

  1045 E Circle Dr, Highland, WI 53543
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  /28

  Est $193,098 Not Listed For Sale

  520 Stone St, Highland, WI 53543

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  520 Stone St, Highland, WI 53543

  Last Sold Summary

  • 21% Above List Price
  • $100/SF
  • 98 Days On Market

  Last Sold Price $160,000

  Last Listing Agent Daniel Tenney MHB Real Estate
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  /37

  $475,000 Sold Sep 19, 2025

  110 Grand St, Highland, WI 53543

  • 3 Beds
  • 2.5 Baths
  • 3,160 Sq Ft
  • Built 2021

  Last Sold Summary

  • 5% Below List Price
  • $150/SF
  • 23 Days On Market

  Current Estimated Value $471,370

  Last Listing Agent Michelene Fisher Fisher Realty Group, LLC

  110 Grand St, Highland, WI 53543
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  /14

  Est $172,825 Not Listed For Sale

  915 Dodgeville St, Highland, WI 53543

  • 3 Beds
  • 1.5 Baths
  • 1,300 Sq Ft
  • Built 1956

  915 Dodgeville St, Highland, WI 53543

  Last Sold Summary

  • 12% Above List Price
  • $119/SF
  • 4 Days On Market

  Last Sold Price $154,900

  Last Listing Agent Bobbi Jo Bomkamp Drone Century 21 Affiliated
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  /21

  Est $154,821 Not Listed For Sale

  518 Main St, Highland, WI 53543

  • 3 Beds
  • 1 Bath
  • 2,176 Sq Ft
  • Built 1900

  518 Main St, Highland, WI 53543

  Last Sold Summary

  • 105% Above List Price
  • $35/SF
  • 128 Days On Market

  Last Sold Price $75,500

  Last Listing Agent Chausti Weinbrenner RE/MAX Preferred
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  Est $140,543 Not Listed For Sale

  522 Main St, Highland, WI 53543

  • 2 Beds
  • 2.5 Baths
  • 1,300 Sq Ft
  • Built 1900

  522 Main St, Highland, WI 53543

  Last Sold Summary

  • 404 Days On Market

  Last Listing Agent Gina Affinito Christie's Real Estate Westchester & Hudson Valley

Showing Results 1 - 40, Page 1 of 18