25

Windsor, WI Homes for Sale under $300,000

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  • L17 Kyla Brooke Ln, Sun Prairie, WI 53590
    L17 Kyla Brooke Ln, Sun Prairie, WI 53590
    L17 Kyla Brooke Ln, Sun Prairie, WI 53590
    /21

    $229,000

    • Land
    • 25,700 Sq Ft
    • $388,136 per Acre

    L17 Kyla Brooke Ln, Sun Prairie, WI 53590

    Lot 17 Windsor Gardens. 2026 Parade of Homes neighborhood! Large country estate lots. Neighborhood features rolling country side views, basketball/tennis court, baseball diamond, state-of-the-art park equipment, a park pavilion and walking trails!

    Kristin Lemke Wisconsin Real Estate Prof, LLC

    L17 Kyla Brooke Ln, Sun Prairie, WI 53590
  • L3 Blue Victoria Dr, Sun Prairie, WI 53590
    L3 Blue Victoria Dr, Sun Prairie, WI 53590
    L3 Blue Victoria Dr, Sun Prairie, WI 53590
    /21

    $299,000

    • Land
    • 1.07 Acres
    • $279,439 per Acre

    L3 Blue Victoria Dr, Sun Prairie, WI 53590

    Lot 3 CSM Windsor Gardens. 2026 Parade of Homes neighborhood! Large country estate lots. Neighborhood features rolling country side views, basketball/tennis court, baseball diamond, state-of-the-art park equipment, a park pavilion and walking trails!

    Kristin Lemke Wisconsin Real Estate Prof, LLC

    L3 Blue Victoria Dr, Sun Prairie, WI 53590
  • L16 Covered Bridge Trail, Sun Prairie, WI 53590
    L16 Covered Bridge Trail, Sun Prairie, WI 53590
    L16 Covered Bridge Trail, Sun Prairie, WI 53590
    /17

    $225,000

    $25K PRICE DROP
    • Land
    • 33,541 Sq Ft
    • $292,208 per Acre

    L16 Covered Bridge Trail, Sun Prairie, WI 53590

    Bring your own builder and create your dream home on this spacious 3⁄4-acre corner lot in the sought-after Windsor Gardens community! Windsor Gardens residents enjoy neighborhood amenities including basketball & tennis courts, a baseball diamond, modern park equipment, a pavilion, & walking trails—all set within a thoughtfully planned community. Located in the DeForest Area School District and

    Hansen Home Team Real Broker LLC

    L16 Covered Bridge Trail, Sun Prairie, WI 53590
  • L2 Blue Victoria Dr, Sun Prairie, WI 53590
    L2 Blue Victoria Dr, Sun Prairie, WI 53590
    L2 Blue Victoria Dr, Sun Prairie, WI 53590
    /21

    $299,000

    • Land
    • 1.07 Acres
    • $279,439 per Acre

    L2 Blue Victoria Dr, Sun Prairie, WI 53590

    Lot 2 CSM Windsor Gardens. 2026 Parade of Homes neighborhood ! Large country estate lots. Neighborhood features rolling country side views, basketball/tennis court, baseball diamond, state-of-the-art park equipment, a park pavilion and walking trails!

    Kristin Lemke Wisconsin Real Estate Prof, LLC

    L2 Blue Victoria Dr, Sun Prairie, WI 53590
  • L128 Lucas Ln, Sun Prairie, WI 53590
    L128 Lucas Ln, Sun Prairie, WI 53590
    L128 Lucas Ln, Sun Prairie, WI 53590
    /21

    $179,000

    • Land
    • 29,620 Sq Ft
    • $263,235 per Acre

    L128 Lucas Ln, Sun Prairie, WI 53590

    Lot 128 Windsor Gardens. 2026 Parade of Homes neighborhood! Large country estate lots. Neighborhood features rolling country side views, basketball/tennis court, baseball diamond, state-of-the-art park equipment, a park pavilion and walking trails!

    Kristin Lemke Wisconsin Real Estate Prof, LLC

    L128 Lucas Ln, Sun Prairie, WI 53590
  • L2 Kyla Brooke Ln, Sun Prairie, WI 53590
    L2 Kyla Brooke Ln, Sun Prairie, WI 53590
    L2 Kyla Brooke Ln, Sun Prairie, WI 53590
    /21

    $219,000

    • Land
    • 29,185 Sq Ft
    • $326,866 per Acre

    L2 Kyla Brooke Ln, Sun Prairie, WI 53590

    Lot 2 Windsor Gardens. 2026 Parade of Homes neighborhood! Large country estate lots. Neighborhood features rolling country side views, basketball/tennis court, baseball diamond, state-of-the-art park equipment, a park pavilion and walking trails!

    Kristin Lemke Wisconsin Real Estate Prof, LLC

    L2 Kyla Brooke Ln, Sun Prairie, WI 53590
  • L125 Lucas Ln, Sun Prairie, WI 53590
    L125 Lucas Ln, Sun Prairie, WI 53590
    L125 Lucas Ln, Sun Prairie, WI 53590
    /21

    $289,000

    • Land
    • 1.33 Acres
    • $217,293 per Acre

    L125 Lucas Ln, Sun Prairie, WI 53590

    Lot 125 Windsor Gardens. 2026 Parade of Homes neighborhood! Large country estate lots. Neighborhood features rolling country side views, basketball/tennis court, baseball diamond, state-of-the-art park equipment, a park pavilion and walking trails!

    Kristin Lemke Wisconsin Real Estate Prof, LLC

    L125 Lucas Ln, Sun Prairie, WI 53590
  • 6801 Parkside Cir, Deforest, WI 53532
    6801 Parkside Cir, Deforest, WI 53532
    6801 Parkside Cir, Deforest, WI 53532
    /41

    $215,000

    • 2 Beds
    • 2 Baths
    • 1,098 Sq Ft

    6801 Parkside Cir, Deforest, WI 53532

    Join Parkside Village 55+ Retirement Community. Parkside Village offers Residents the opportunity to Purchase their unit through a Limited Life Estate Grant. Parkside Village offers numerous amenities: a clubhouse, library, fitness center, movie room, billiards room, common grilling station, on-site management and on-site maintenance, Common Area House Keeping. No property taxes! The monthly

    Alex Filkouski Madison Commercial Real Estate LLC

    6801 Parkside Cir, Deforest, WI 53532
  • L143 Lucas Ln, Sun Prairie, WI 53590
    L143 Lucas Ln, Sun Prairie, WI 53590
    L143 Lucas Ln, Sun Prairie, WI 53590
    /21

    $199,000

    • Land
    • 28,314 Sq Ft
    • $306,154 per Acre

    L143 Lucas Ln, Sun Prairie, WI 53590

    Lot 143 Windsor Gardens. 2026 Parade of Homes neighborhood ! Large country estate lots. Neighborhood features rolling country side views, basketball/tennis court, baseball diamond, state-of-the-art park equipment, a park pavilion and walking trails!

    Kristin Lemke Wisconsin Real Estate Prof, LLC

    L143 Lucas Ln, Sun Prairie, WI 53590
  • Lot 28 Colton Way, Windsor, WI 53590
    Lot 28 Colton Way, Windsor, WI 53590
    Lot 28 Colton Way, Windsor, WI 53590
    /3

    $250,000

    • Land
    • 27,442 Sq Ft
    • $396,825 per Acre

    Lot 28 Colton Way, Windsor, WI 53590

    Build your dream home on this scenic, tree-lined lot overlooking a beautiful open field on Lot 28 in Windsor Gardens. Enjoy nearby parks and walking paths, plus easy access to shopping, dining, and the interstate. A perfect blend of nature and convenience. Lot sale is subject to a separate building agreement with Willow Ridge Design Build.

    Molli Babler Keller Williams Realty

    Lot 28 Colton Way, Windsor, WI 53590
  • Lot 417 Whistle Rock Cir, Deforest, WI 53532
    Lot 417 Whistle Rock Cir, Deforest, WI 53532
    Lot 417 Whistle Rock Cir, Deforest, WI 53532
    /8

    $143,900

    • Land
    • 15,246 Sq Ft
    • $411,143 per Acre

    Lot 417 Whistle Rock Cir, Deforest, WI 53532

    Build your future in Bear Tree Farms, a master-planned community located between DeForest, Windsor, and Sun Prairie with quick access to Hwy 51 and the Madison metro. This destination neighborhood offers generously sized lots, modern new homes, and exceptional amenities. Residents enjoy a 22-acre community park with splash pad, playgrounds, tennis, basketball and pickleball courts, plus walking

    Aeryn Barry Tim O'Brien Homes LLC

    Lot 417 Whistle Rock Cir, Deforest, WI 53532
  • L138 Colton Way, Sun Prairie, WI 53590
    L138 Colton Way, Sun Prairie, WI 53590
    L138 Colton Way, Sun Prairie, WI 53590
    /20

    $179,000

    • Land
    • 21,780 Sq Ft
    • $358,000 per Acre

    L138 Colton Way, Sun Prairie, WI 53590

    Lot 138 Windsor Gardens. 2026 Parade of Homes neighborhood ! Large country estate lots. Neighborhood features rolling country side views, basketball/tennis court, baseball diamond, state-of-the-art park equipment, a park pavilion and walking trails!

    Kristin Lemke Wisconsin Real Estate Prof, LLC

    L138 Colton Way, Sun Prairie, WI 53590
  • L18 Kyla Brooke Ln, Sun Prairie, WI 53590
    L18 Kyla Brooke Ln, Sun Prairie, WI 53590
    L18 Kyla Brooke Ln, Sun Prairie, WI 53590
    /21

    $229,000

    • Land
    • 25,264 Sq Ft
    • $394,828 per Acre

    L18 Kyla Brooke Ln, Sun Prairie, WI 53590

    Lot 18 Windsor Gardens. 2026 Parade of Homes neighborhood! Large country estate lots. Neighborhood features rolling country side views, basketball/tennis court, baseball diamond, state-of-the-art park equipment, a park pavilion and walking trails!

    Kristin Lemke Wisconsin Real Estate Prof, LLC

    L18 Kyla Brooke Ln, Sun Prairie, WI 53590
  • 6836 Parkside Cir, Deforest, WI 53532
    6836 Parkside Cir, Deforest, WI 53532
    6836 Parkside Cir, Deforest, WI 53532
    /29

    $140,000

    $10K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 818 Sq Ft

    6836 Parkside Cir, Deforest, WI 53532

    Join Parkside Village 55+ Retirement Community. Parkside Village offers Residents the opportunity to Purchase their unit through a Limited Life Estate Grant. Parkside Village offers numerous amenities: a clubhouse, library, fitness center, movie room, billiards room, common grilling station, on-site management and on-site maintenance, Common Area House Keeping. No property taxes! The monthly

    Alex Filkouski Madison Commercial Real Estate LLC

    6836 Parkside Cir, Deforest, WI 53532
  • L130 Blue Victoria Dr, Sun Prairie, WI 53590
    L130 Blue Victoria Dr, Sun Prairie, WI 53590
    L130 Blue Victoria Dr, Sun Prairie, WI 53590
    /21

    $199,000

    • Land
    • 26,571 Sq Ft
    • $326,230 per Acre

    L130 Blue Victoria Dr, Sun Prairie, WI 53590

    Lot 130 Windsor Gardens. 2026 Parade of Homes neighborhood ! Large country estate lots. Neighborhood features rolling country side views, basketball/tennis court, baseball diamond, state-of-the-art park equipment, a park pavilion and walking trails!

    Kristin Lemke Wisconsin Real Estate Prof, LLC

    L130 Blue Victoria Dr, Sun Prairie, WI 53590
  • 6687 Florance Ruth Ln, Windsor, WI 53590
    6687 Florance Ruth Ln, Windsor, WI 53590
    6687 Florance Ruth Ln, Windsor, WI 53590
    /21

    $169,000

    • Land
    • 23,086 Sq Ft
    • $318,868 per Acre

    6687 Florance Ruth Ln, Windsor, WI 53590

    Lot 3 Windsor Gardens Field of Dreams. Beautiful country estate lots within minutes of Sun Prairie!! A 2026 Parade of Homes neighborhood , this country subdivision features basketball/tennis court, baseball diamond, state-of-the-art park equipment, a park pavilion and walking trails!

    Kristin Lemke Wisconsin Real Estate Prof, LLC

    6687 Florance Ruth Ln, Windsor, WI 53590
  • L22 Colton Way, Windsor, WI 53590
    L22 Colton Way, Windsor, WI 53590
    L22 Colton Way, Windsor, WI 53590
    /21

    $249,000

    • Land
    • 27,442 Sq Ft
    • $395,238 per Acre

    L22 Colton Way, Windsor, WI 53590

    Lot 22 Windsor Gardens. 2026 Parade of Homes neighborhood ! Large country estate lots. Neighborhood features rolling country side views, basketball/tennis court, baseball diamond, state-of-the-art park equipment, a park pavilion and walking trails!

    Kristin Lemke Wisconsin Real Estate Prof, LLC

    L22 Colton Way, Windsor, WI 53590
  • 6828 Parkside Cir, Windsor, WI 53532
    6828 Parkside Cir, Windsor, WI 53532
    6828 Parkside Cir, Windsor, WI 53532
    /46

    $220,000

    • 2 Beds
    • 2 Baths
    • 1,132 Sq Ft

    6828 Parkside Cir, Windsor, WI 53532

    Join Parkside Village 55+ Retirement Community. Parkside Village offers Residents the opportunity to Purchase their unit through a Limited Life Estate Grant. Parkside Village offers numerous amenities: a clubhouse, library, fitness center, movie room, billiards room, common grilling station, on-site management and on-site maintenance, Common Area House Keeping. No property taxes! The monthly

    Alex Filkouski Madison Commercial Real Estate LLC

    6828 Parkside Cir, Windsor, WI 53532
  • L129 Lucas Ln, Sun Prairie, WI 53590
    L129 Lucas Ln, Sun Prairie, WI 53590
    L129 Lucas Ln, Sun Prairie, WI 53590
    /21

    $179,000

    • Land
    • 23,958 Sq Ft
    • $325,455 per Acre

    L129 Lucas Ln, Sun Prairie, WI 53590

    Lot 129 Windsor Gardens. 2026 Parade of Homes neighborhood! Large country estate lots. Neighborhood features rolling country side views, basketball/tennis court, baseball diamond, state-of-the-art park equipment, a park pavilion and walking trails!

    Kristin Lemke Wisconsin Real Estate Prof, LLC

    L129 Lucas Ln, Sun Prairie, WI 53590
  • L137 Colton Way, Sun Prairie, WI 53590
    L137 Colton Way, Sun Prairie, WI 53590
    L137 Colton Way, Sun Prairie, WI 53590
    /20

    $179,000

    • Land
    • 23,522 Sq Ft
    • $331,481 per Acre

    L137 Colton Way, Sun Prairie, WI 53590

    Lot 137 Windsor Gardens. 2026 Parade of Homes neighborhood ! Large country estate lots. Neighborhood features rolling country side views, basketball/tennis court, baseball diamond, state-of-the-art park equipment, a park pavilion and walking trails!

    Kristin Lemke Wisconsin Real Estate Prof, LLC

    L137 Colton Way, Sun Prairie, WI 53590
  • L3 Kyla Brooke Ln, Sun Prairie, WI 53590
    L3 Kyla Brooke Ln, Sun Prairie, WI 53590
    L3 Kyla Brooke Ln, Sun Prairie, WI 53590
    /21

    $209,000

    • Land
    • 27,442 Sq Ft
    • $331,746 per Acre

    L3 Kyla Brooke Ln, Sun Prairie, WI 53590

    Lot 3 Windsor Gardens. 2026 Parade of Homes neighborhood! Large country estate lots. Neighborhood features rolling country side views, basketball/tennis court, baseball diamond, state-of-the-art park equipment, a park pavilion and walking trails!

    Kristin Lemke Wisconsin Real Estate Prof, LLC

    L3 Kyla Brooke Ln, Sun Prairie, WI 53590
  • 3171 Lymans Run, Sun Prairie, WI 53590
    3171 Lymans Run, Sun Prairie, WI 53590
    3171 Lymans Run, Sun Prairie, WI 53590
    /21

    $199,000

    • Land
    • 28,749 Sq Ft
    • $301,515 per Acre

    3171 Lymans Run, Sun Prairie, WI 53590

    Lot 162 Windsor Gardens. Windsor Gardens has beautiful country estate lots within minutes of Sun Prairie!! Country Subdivision features basketball/tennis court, baseball diamond, state-of-the-art park equipment, a park pavilion and walking trails!

    Kristin Lemke Wisconsin Real Estate Prof, LLC

    3171 Lymans Run, Sun Prairie, WI 53590
  • 6558 Hickory Glade Dr, Deforest, WI 53532
    6558 Hickory Glade Dr, Deforest, WI 53532
    6558 Hickory Glade Dr, Deforest, WI 53532
    /8

    $143,900

    • Land
    • 22,651 Sq Ft
    • $276,731 per Acre

    6558 Hickory Glade Dr, Deforest, WI 53532

    Build your future in Bear Tree Farms, a master-planned community located between DeForest, Windsor, and Sun Prairie with quick access to Hwy 51 and the Madison metro. This destination neighborhood offers generously sized lots, modern new homes, and exceptional amenities. Residents enjoy a 22-acre community park with splash pad, playgrounds, tennis, basketball and pickleball courts, plus walking

    Aeryn Barry Tim O'Brien Homes LLC

    6558 Hickory Glade Dr, Deforest, WI 53532
  • 3175 Lymans Run, Sun Prairie, WI 53590
    3175 Lymans Run, Sun Prairie, WI 53590
    3175 Lymans Run, Sun Prairie, WI 53590
    /21

    $199,000

    • Land
    • 28,749 Sq Ft
    • $301,515 per Acre

    3175 Lymans Run, Sun Prairie, WI 53590

    Lot 161 Windsor Gardens. Windsor Gardens has beautiful country estate lots within minutes of Sun Prairie!! Country Subdivision features basketball/tennis court, baseball diamond, state-of-the-art park equipment, a park pavilion and walking trails!

    Kristin Lemke Wisconsin Real Estate Prof, LLC

    3175 Lymans Run, Sun Prairie, WI 53590
  • Lot 413 Whistle Rock Cir, Deforest, WI 53532
    Lot 413 Whistle Rock Cir, Deforest, WI 53532
    Lot 413 Whistle Rock Cir, Deforest, WI 53532
    /8

    $129,900

    • Land
    • 12,196 Sq Ft
    • $463,929 per Acre

    Lot 413 Whistle Rock Cir, Deforest, WI 53532

    Build your future in Bear Tree Farms, a master-planned community located between DeForest, Windsor, and Sun Prairie with quick access to Hwy 51 and the Madison metro. This destination neighborhood offers generously sized lots, modern new homes, and exceptional amenities. Residents enjoy a 22-acre community park with splash pad, playgrounds, tennis, basketball and pickleball courts, plus walking

    Aeryn Barry Tim O'Brien Homes LLC

    Lot 413 Whistle Rock Cir, Deforest, WI 53532
Wisconsin Dane County Windsor

Real Estate & Homes in Windsor, WI under $300,000

Home Prices in Windsor, WI

The median home sale price in Windsor, WI is $538,910, down 2% year-over-year. Homes in Windsor sell in 37 days on average, compared to the national average of 57 days.

Home Price Trends

Median Sale Price
$538,910
Median Single Family Sale Price
$549,900
Median 2 Bedroom Sale Price
$288,500
Average Price Per Sq Ft
$233
Number of Homes for Sale
7
Last 12 months Home Sales
55
Months of Supply
1.50
Median List Price
$555,090
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-2%
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