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Windsor, WI Homes for Sale under $500,000

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  • 4743 Bellflower Dr, de Forest, WI 53532
    4743 Bellflower Dr, de Forest, WI 53532
    4743 Bellflower Dr, de Forest, WI 53532
    /33

    $445,000

    New Construction $5K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,901 Sq Ft

    4743 Bellflower Dr, de Forest, WI 53532

    OPEN HOUSES WILL BE HELD AT OUR FURNISHED MODEL AT 4741 BELLFLOWER DR. Approx. completion end of July 2026. Quality built 2 story townhouses with 1,900 sq ft, 3 bedrooms, 2 1/2 baths, spacious kitchen & dining area with solid surface countertops, Amish custom cabinets, stainless steel appliances, great room with gas fireplace and large window with tons of natural light, owners suite with huge

    Agent Photo

    Kelly Bennett

    First Weber Inc

    4743 Bellflower Dr, de Forest, WI 53532
  • Unit 5.1 Bellflower Dr, Deforest, WI 53532
    Unit 5.1 Bellflower Dr, Deforest, WI 53532
    Unit 5.1 Bellflower Dr, Deforest, WI 53532
    /27

    $460,000

    New Construction $15K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,901 Sq Ft

    Unit 5.1 Bellflower Dr, Deforest, WI 53532

    OPEN HOUSES WILL BE HELD AT OUR FURNISHED MODEL AT 4741 BELLFLOWER DR. Approx. completion end of June 2026. Quality built 2 story townhouses with 1,900 sq ft, 3 bedrooms, 2 1/2 baths, spacious kitchen & dining area with solid surface countertops, Amish custom cabinets, stainless steel appliances, great room with gas fireplace and large window with tons of natural light, owners suite with huge

    Agent Photo

    Kelly Bennett

    First Weber Inc

    Unit 5.1 Bellflower Dr, Deforest, WI 53532
  • 6551 Linden Cir, Windsor, WI 53598
    6551 Linden Cir, Windsor, WI 53598
    6551 Linden Cir, Windsor, WI 53598
    /37

    $475,000

    • 3 Beds
    • 2 Baths
    • 2,449 Sq Ft

    6551 Linden Cir, Windsor, WI 53598

    Imagine coming home to the peaceful charm of the Lake Windsor neighborhood! Set on a beautiful 0.68-acre lot with a fenced-in yard, this inviting home offers the space, comfort, and setting you’ve been searching for. Inside, gather around the cozy fireplace or out in the screened porch overlooking the private backyard. The finished lower level adds even more flexibility, offering an ideal space

    Spencer Schumacher Spencer Real Estate Group

    6551 Linden Cir, Windsor, WI 53598
  • L23 Colton Way, Windsor, WI 53590
    L23 Colton Way, Windsor, WI 53590
    L23 Colton Way, Windsor, WI 53590
    /21

    $249,000

    • Land
    • 27,007 Sq Ft
    • $401,613 per Acre

    L23 Colton Way, Windsor, WI 53590

    Lot 23 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

    L23 Colton Way, Windsor, WI 53590
  • 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
  • L117 Naomi Trail, Sun Prairie, WI 53590
    L117 Naomi Trail, Sun Prairie, WI 53590
    L117 Naomi Trail, Sun Prairie, WI 53590
    /20

    $229,000

    • Land
    • 30,492 Sq Ft
    • $327,143 per Acre

    L117 Naomi Trail, Sun Prairie, WI 53590

    Lot 117 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

    L117 Naomi Trail, 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
  • 6659 Ramshorn Dr, Windsor, WI 53532
    6659 Ramshorn Dr, Windsor, WI 53532
    6659 Ramshorn Dr, Windsor, WI 53532
    /15

    $499,900

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,902 Sq Ft

    6659 Ramshorn Dr, Windsor, WI 53532

    Welcome to Lot 285 in Bear Tree Farms, featuring the newly built Topaz Plan! This 3-bedroom, 2-bath ranch offers over 1,900 sq ft of thoughtfully designed living space just minutes from Madison. Enjoy upscale finishes throughout, including open railings with black iron balusters, oversized 5" base trim, stainless steel appliances, granite countertops, soft-close cabinetry, 42" upper cabinets, a

    Kyle Carrier Best Realty of Edgerton

    6659 Ramshorn Dr, Windsor, WI 53532
  • 6683 Charlie Grimm Rd, Windsor, WI 53598
    6683 Charlie Grimm Rd, Windsor, WI 53598
    6683 Charlie Grimm Rd, Windsor, WI 53598
    /32

    $269,900

    $5K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,104 Sq Ft

    6683 Charlie Grimm Rd, Windsor, WI 53598

    Enjoy carefree living with no condo fees in this beautifully updated half-duplex overlooking picturesque Lake Windsor Country Club and the Yahara River. The bright, open-concept design features luxury flooring, fresh paint, and large windows that fill the home with natural light while showcasing peaceful golf course views. The remodeled kitchen offers granite countertops, subway tile backsplash,

    Eric Breidel Investment Realty Services LLC

    6683 Charlie Grimm Rd, Windsor, WI 53598
  • 6823 Parkside Cir, de Forest, WI 53532
    6823 Parkside Cir, de Forest, WI 53532
    6823 Parkside Cir, de Forest, WI 53532
    /36

    $215,000

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

    6823 Parkside Cir, de Forest, 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

    6823 Parkside Cir, de Forest, WI 53532
  • 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
  • 0 N Towne Rd Unit 2029450, Windsor, WI 53598
    0 N Towne Rd Unit 2029450, Windsor, WI 53598
    /2

    $449,900

    • Land
    • 1.14 Acres
    • $394,649 per Acre

    0 N Towne Rd Unit 2029450, Windsor, WI 53598

    Commercial lot in Growing Windsor! Great location near new Windsor Fire Station, Gingerbread House an The Windsor Restaurant.

    Mark Pawlowsky Stark Company, REALTORS

    0 N Towne Rd Unit 2029450, Windsor, WI 53598
  • 6614 Ramshorn Dr, Deforest, WI 53532
    6614 Ramshorn Dr, Deforest, WI 53532
    6614 Ramshorn Dr, Deforest, WI 53532
    /23

    $479,999

    $55K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,872 Sq Ft

    6614 Ramshorn Dr, Deforest, WI 53532

    Beautiful Ranch Home in Bear Tree Farms, three bedroom, two bath Home including finished lower level family room, custom kitchen with quartz counters, vaulted ceilings & white trim/cabinet package. Property is at a spacious corner lot with wonderful views of the woods in the distance. Just steps away from the Windsor Park & bike/walking trail.

    Josh Lamp Berkshire Hathaway HomeServices True Realty

    6614 Ramshorn Dr, Deforest, WI 53532
  • 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
  • 6715 Firehouse Dr, Windsor, WI 53598
    6715 Firehouse Dr, Windsor, WI 53598
    /2

    $334,900

    • Land
    • 28,749 Sq Ft
    • $507,424 per Acre

    6715 Firehouse Dr, Windsor, WI 53598

    Commercial lot in Growing Windsor. Great location near Windsor Fire Station, Gingerbread House and The Windsor Restaurant.

    Mark Pawlowsky Stark Company, REALTORS

    6715 Firehouse Dr, Windsor, WI 53598
  • L1 Blue Victoria Dr, Sun Prairie, WI 53590
    L1 Blue Victoria Dr, Sun Prairie, WI 53590
    L1 Blue Victoria Dr, Sun Prairie, WI 53590
    /21

    $239,000

    $10K PRICE INCREASE
    • Land
    • 33,976 Sq Ft
    • $306,410 per Acre

    L1 Blue Victoria Dr, Sun Prairie, WI 53590

    Lot 1 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

    L1 Blue Victoria Dr, 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
  • 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
  • L28 Colton Way, Sun Prairie, WI 53590
    L28 Colton Way, Sun Prairie, WI 53590
    /2

    $250,000

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

    L28 Colton Way, Sun Prairie, WI 53590

    Imagine building your dream home on a beautiful, large, tree-lined and farm field country lot in the sought-after Windsor Gardens neighborhood. With very few tree lined lots left, the chance to create a truly custom home on an exceptional homesite surrounded by mature trees and peaceful country views could be yours. Bring your vision or let the builder help you with a building plan. Opportunity

    Molli Babler Keller Williams Realty

    L28 Colton Way, Sun Prairie, WI 53590
  • 4351 Windsor Rd, Windsor, WI 53598
    4351 Windsor Rd, Windsor, WI 53598
    4351 Windsor Rd, Windsor, WI 53598
    /28

    $450,000

    $15K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 1,141 Sq Ft

    4351 Windsor Rd, Windsor, WI 53598

    Charming 4-Bedroom Home with Modern Updates – Sold As-Is Step into this spacious 4-bedroom, 2.5-bath home that blends recent upgrades with room for your personal touch. The remodeled kitchen, bathrooms, and finished basement offer a fresh, modern feel, while major mechanical updates provide peace of mind — new furnace (2024), water heater (2024), roof (2022), and windows (2025). Inside, you’ll

    Stephanie Payne Realty of America, LLC

    4351 Windsor Rd, Windsor, WI 53598
  • 118 Renata Ct, de Forest, WI 53532
    118 Renata Ct, de Forest, WI 53532
    118 Renata Ct, de Forest, WI 53532
    /39

    $345,000

    $5K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft

    118 Renata Ct, de Forest, WI 53532

    Wonderful opportunity to own in DeForest! This well-maintained half duplex offers a great combination of comfort, convenience and value in a fantastic location close to schools, parks and everything DeForest has to offer. Step inside to a welcoming and functional layout with plenty of space to make your own. Updated mechanicals provide added peace of mind, while the attached 2-car garage offers

    Ken Brenner Stark Company, REALTORS

    118 Renata Ct, de Forest, WI 53532
Wisconsin Dane County

Real Estate & Homes in Windsor, WI under $500,000

Home Prices in Windsor, WI

The median home sale price in Windsor, WI is $540,000, up 1% year-over-year. Homes in Windsor sell in 35 days on average, compared to the national average of 55 days.

Home Price Trends

Median Sale Price
$540,000
Median Single Family Sale Price
$539,455
Median 2 Bedroom Sale Price
$288,500
Median 1 Bedroom Sale Price
$77,500
Average Price Per Sq Ft
$234
Number of Homes for Sale
11
Last 12 months Home Sales
43
Months of Supply
3.10
Median List Price
$539,950
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
1%
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