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$199,900
ACTIVE Status
Welcome HOME to Highland Estates in Pleasant Prairie where community, lifestyle, and location come together! You're close to schools, shopping, restaurants, recreation and minutes to Lake Michigan shoreline....while still coming home to a peaceful neighborhood with plenty of open space. LOT 122 includes 11,911 square feet! Highland Estates...A place where you know your neighbors, where families grow, friendships are made, and the little everyday moments become some of your favorite memories. Conveniently located in between MKE and Chicago! Minutes to Interstate 94! This is more than a place to live. It's a place to call home!!!! DON'T WAIT!

Lt122 Cooper Road, Pleasant Prairie

Listing courtesy of EXP Realty, LLC Kenosha.

$224,900
ACTIVE Status
Welcome HOME to Highland Estates in Pleasant Prairie where community, lifestyle, and location come together! You're close to schools, shopping, restaurants, recreation and minutes to Lake Michigan shoreline....while still coming home to a peaceful neighborhood with plenty of open space. LOT 121 includes 13,998 square feet! Highland Estates...A place where you know your neighbors, where families grow, friendships are made, and the little everyday moments become some of your favorite memories. Conveniently located in between MKE and Chicago! Minutes to Interstate 94! This is more than a place to live. It's a place to call home!!!! DON'T WAIT!

Lt121 Cooper Road, Pleasant Prairie

Listing courtesy of EXP Realty, LLC Kenosha.

$224,900
ACTIVE Status
Welcome HOME to Highland Estates in Pleasant Prairie where community, lifestyle, and location come together! You're close to schools, shopping, restaurants, recreation and minutes to Lake Michigan shoreline....while still coming home to a peaceful neighborhood with plenty of open space. LOT 120 includes 14,082 square feet! Highland Estates...A place where you know your neighbors, where families grow, friendships are made, and the little everyday moments become some of your favorite memories. Conveniently located in between MKE and Chicago! Minutes to Interstate 94! This is more than a place to live. It's a place to call home!!!! DON'T WAIT!

Lt120 Cooper Road, Pleasant Prairie

Listing courtesy of EXP Realty, LLC Kenosha.

$229,900
ACTIVE Status
Welcome HOME to Highland Estates in Pleasant Prairie where community, lifestyle, and location come together! You're close to schools, shopping, restaurants, recreation and minutes to Lake Michigan shoreline....while still coming home to a peaceful neighborhood with plenty of open space. LOT 119 includes 15,124 square feet! Highland Estates...A place where you know your neighbors, where families grow, friendships are made, and the little everyday moments become some of your favorite memories. Conveniently located in between MKE and Chicago! Minutes to Interstate 94! This is more than a place to live. It's a place to call home!!!! DON'T WAIT!

Lt119 Cooper Road, Pleasant Prairie

Listing courtesy of EXP Realty, LLC Kenosha.

$239,900
ACTIVE Status
Welcome HOME to Highland Estates in Pleasant Prairie where community, lifestyle, and location come together! You're close to schools, shopping, restaurants, recreation and minutes to Lake Michigan shoreline....while still coming home to a peaceful neighborhood with plenty of open space. LOT 118 includes 16,338 square feet! Highland Estates...A place where you know your neighbors, where families grow, friendships are made, and the little everyday moments become some of your favorite memories. Conveniently located in between MKE and Chicago! Minutes to Interstate 94! This is more than a place to live. It's a place to call home!!!! DON'T WAIT!

Lt118 Cooper Road, Pleasant Prairie

Listing courtesy of EXP Realty, LLC Kenosha.

$269,900
ACTIVE Status
Welcome HOME to Highland Estates in Pleasant Prairie where community, lifestyle, and location come together! You're close to schools, shopping, restaurants, recreation and minutes to Lake Michigan shoreline....while still coming home to a peaceful neighborhood with plenty of open space. LOT 117 includes 24,941 square feet! Highland Estates...A place where you know your neighbors, where families grow, friendships are made, and the little everyday moments become some of your favorite memories. Conveniently located in between MKE and Chicago! Minutes to Interstate 94! This is more than a place to live. It's a place to call home!!!! DON'T WAIT!

Lt117 51st Court, Pleasant Prairie

Listing courtesy of EXP Realty, LLC Kenosha.

$475,000
ACTIVE Status
A Private Wisconsin Sanctuary - 9.8 Acres of Wooded Beauty, Creekside Views & Endless Possibilities! Discover nearly 10 breathtaking acres in Pleasant Prairie, where privacy, natural beauty and opportunity come together. Mature trees surround this peaceful property while a meandering creek creates picturesque views and a tranquil setting for a future dream estate, family retreat or development vision. An abundance of Wisconsin wildlife can be enjoyed throughout the property. Field wetland delineation work was completed by Heartland Ecological Group in 2023, and conceptual development plans are available for review. Imagine a home designed to embrace the beauty of the land while remaining close to modern conveniences. A rare opportunity to own a truly special piece of Wisconsin.

Sheridan Road, Pleasant Prairie

Listing courtesy of RE/MAX Plaza.

$239,900
ACTIVE Status
Welcome HOME to Highland Estates in Pleasant Prairie where community, lifestyle, and location come together! You're close to schools, shopping, restaurants, recreation and minutes to Lake Michigan shoreline....while still coming home to a peaceful neighborhood with plenty of open space. LOT 116 includes 16,599 square feet! Highland Estates...A place where you know your neighbors, where families grow, friendships are made, and the little everyday moments become some of your favorite memories. Conveniently located in between MKE and Chicago! Minutes to Interstate 94! This is more than a place to live. It's a place to call home!!!! DON'T WAIT!

Lt116 51st Court, Pleasant Prairie

Listing courtesy of EXP Realty, LLC Kenosha.

$249,900
ACTIVE Status
Welcome HOME to Highland Estates in Pleasant Prairie where community, lifestyle, and location come together! You're close to schools, shopping, restaurants, recreation and minutes to Lake Michigan shoreline....while still coming home to a peaceful neighborhood with plenty of open space. LOT 115 includes 20,362 square feet! Highland Estates...A place where you know your neighbors, where families grow, friendships are made, and the little everyday moments become some of your favorite memories. Conveniently located in between MKE and Chicago! Minutes to Interstate 94! This is more than a place to live. It's a place to call home!!!! DON'T WAIT!

Lt115 51st Court, Pleasant Prairie

Listing courtesy of EXP Realty, LLC Kenosha.

$224,900
ACTIVE Status
Welcome HOME to Highland Estates in Pleasant Prairie where community, lifestyle, and location come together! You're close to schools, shopping, restaurants, recreation and minutes to Lake Michigan shoreline....while still coming home to a peaceful neighborhood with plenty of open space. LOT 112 includes 17,993 square feet! Highland Estates...A place where you know your neighbors, where families grow, friendships are made, and the little everyday moments become some of your favorite memories. Conveniently located in between MKE and Chicago! Minutes to Interstate 94! This is more than a place to live. It's a place to call home!!!! DON'T WAIT!

Lt112 Cooper Road, Pleasant Prairie

Listing courtesy of EXP Realty, LLC Kenosha.

$219,900
ACTIVE Status
POND VIEW!! Welcome HOME to Highland Estates in Pleasant Prairie where community, lifestyle, and location come together! You're close to schools, shopping, restaurants, recreation and minutes to Lake Michigan shoreline....while still coming home to a peaceful neighborhood with plenty of open space. LOT 110 includes 14,494 square feet! Highland Estates...A place where you know your neighbors, where families grow, friendships are made, and the little everyday moments become some of your favorite memories. Conveniently located in between MKE and Chicago! Minutes to Interstate 94! This is more than a place to live. It's a place to call home!!!! DON'T WAIT!

Lt110 Cooper Road, Pleasant Prairie

Listing courtesy of EXP Realty, LLC Kenosha.

$259,900
ACTIVE Status
Welcome HOME to Highland Estates in Pleasant Prairie where community, lifestyle, and location come together! You're close to schools, shopping, restaurants, recreation and minutes to Lake Michigan shoreline....while still coming home to a peaceful neighborhood with plenty of open space. LOT 111 includes 20,278 square feet! Highland Estates...A place where you know your neighbors, where families grow, friendships are made, and the little everyday moments become some of your favorite memories. Conveniently located in between MKE and Chicago! Minutes to Interstate 94! This is more than a place to live. It's a place to call home!!!! DON'T WAIT!

Lt111 Cooper Road, Pleasant Prairie

Listing courtesy of EXP Realty, LLC Kenosha.

$219,900
ACTIVE Status
POND VIEW! Welcome HOME to Highland Estates in Pleasant Prairie where community, lifestyle, and location come together! You're close to schools, shopping, restaurants, recreation and minutes to Lake Michigan shoreline....while still coming home to a peaceful neighborhood with plenty of open space. LOT 109 includes 14,838 square feet! Highland Estates...A place where you know your neighbors, where families grow, friendships are made, and the little everyday moments become some of your favorite memories. Conveniently located in between MKE and Chicago! Minutes to Interstate 94! This is more than a place to live. It's a place to call home!!!! DON'T WAIT!

Lt109 Cooper Road, Pleasant Prairie

Listing courtesy of EXP Realty, LLC Kenosha.

$214,900
ACTIVE Status
Welcome HOME to Highland Estates in Pleasant Prairie where community, lifestyle, and location come together! You're close to schools, shopping, restaurants, recreation and minutes to Lake Michigan shoreline....while still coming home to a peaceful neighborhood with plenty of open space. LOT 108 includes 16,492 square feet! Highland Estates...A place where you know your neighbors, where families grow, friendships are made, and the little everyday moments become some of your favorite memories. Conveniently located in between MKE and Chicago! Minutes to Interstate 94! This is more than a place to live. It's a place to call home!!!! DON'T WAIT!

Lt108 Highland Place, Pleasant Prairie

Listing courtesy of EXP Realty, LLC Kenosha.

$209,900
ACTIVE Status
Welcome HOME to Highland Estates in Pleasant Prairie where community, lifestyle, and location come together! You're close to schools, shopping, restaurants, recreation and minutes to Lake Michigan shoreline....while still coming home to a peaceful neighborhood with plenty of open space. LOT 101 includes 15,030 square feet!Highland Estates...A place where you know your neighbors, where families grow, friendships are made, and the little everyday moments become some of your favorite memories. Conveniently located in between MKE and Chicago! Minutes to Interstate 94! This is more than a place to live. It's a place to call home!!!! DON'T WAIT!

Lt101 49th Court, Pleasant Prairie

Listing courtesy of EXP Realty, LLC Kenosha.

$209,900
ACTIVE Status
Welcome HOME to Highland Estates in Pleasant Prairie where community, lifestyle, and location come together! You're close to schools, shopping, restaurants, recreation and minutes to Lake Michigan shoreline....while still coming home to a peaceful neighborhood with plenty of open space. LOT 96 includes 15,481 square feet! Highland Estates...A place where you know your neighbors, where families grow, friendships are made, and the little everyday moments become some of your favorite memories. Conveniently located in between MKE and Chicago! Minutes to Interstate 94! This is more than a place to live. It's a place to call home!!!! DON'T WAIT!

Lt96 49th Court, Pleasant Prairie

Listing courtesy of EXP Realty, LLC Kenosha.

$209,900
ACTIVE Status
Welcome HOME to Highland Estates in Pleasant Prairie where community, lifestyle, and location come together! You're close to schools, shopping, restaurants, recreation and minutes to Lake Michigan shoreline....while still coming home to a peaceful neighborhood with plenty of open space. LOT 95 includes 15,214 square feet!Highland Estates...A place where you know your neighbors, where families grow, friendships are made, and the little everyday moments become some of your favorite memories. Conveniently located in between MKE and Chicago! Minutes to Interstate 94! This is more than a place to live. It's a place to call home!!!! DON'T WAIT!

Lt95 49th Court, Pleasant Prairie

Listing courtesy of EXP Realty, LLC Kenosha.

$209,900
ACTIVE Status
Welcome HOME to Highland Estates in Pleasant Prairie where community, lifestyle, and location come together! You're close to schools, shopping, restaurants, recreation and minutes to Lake Michigan shoreline....while still coming home to a peaceful neighborhood with plenty of open space. LOT 94 includes 15,248 square feet! Highland Estates...A place where you know your neighbors, where families grow, friendships are made, and the little everyday moments become some of your favorite memories. Conveniently located in between MKE and Chicago! Minutes to Interstate 94! This is more than a place to live. It's a place to call home!!!! DON'T WAIT!

Lt94 49th Court, Pleasant Prairie

Listing courtesy of EXP Realty, LLC Kenosha.

$209,900
ACTIVE Status
Welcome HOME to Highland Estates in Pleasant Prairie where community, lifestyle, and location come together! You're close to schools, shopping, restaurants, recreation and minutes to Lake Michigan shoreline....while still coming home to a peaceful neighborhood with plenty of open space. LOT 92 includes 15,013 square feet!Highland Estates...A place where you know your neighbors, where families grow, friendships are made, and the little everyday moments become some of your favorite memories. Conveniently located in between MKE and Chicago! Minutes to Interstate 94! This is more than a place to live. It's a place to call home!!!! DON'T WAIT!

Lt92 49th Court, Pleasant Prairie

Listing courtesy of EXP Realty, LLC Kenosha.

$209,900
ACTIVE Status
Welcome HOME to Highland Estates in Pleasant Prairie where community, lifestyle, and location come together! You're close to schools, shopping, restaurants, recreation and minutes to Lake Michigan shoreline....while still coming home to a peaceful neighborhood with plenty of open space. LOT 91 includes 15,100 square feet!Highland Estates...A place where you know your neighbors, where families grow, friendships are made, and the little everyday moments become some of your favorite memories. Conveniently located in between MKE and Chicago! Minutes to Interstate 94! This is more than a place to live. It's a place to call home!!!! DON'T WAIT!

Lt91 49th Court, Pleasant Prairie

Listing courtesy of EXP Realty, LLC Kenosha.

$223,900
ACTIVE Status
Welcome HOME to Highland Estates in Pleasant Prairie where community, lifestyle, and location come together! You're close to schools, shopping, restaurants, recreation and minutes to Lake Michigan shoreline....while still coming home to a peaceful neighborhood with plenty of open space. LOT 90 includes 16,879 square feet!Highland Estates...A place where you know your neighbors, where families grow, friendships are made, and the little everyday moments become some of your favorite memories. Conveniently located in between MKE and Chicago! Minutes to Interstate 94! This is more than a place to live. It's a place to call home!!!! DON'T WAIT!

Lt90 49th Court, Pleasant Prairie

Listing courtesy of EXP Realty, LLC Kenosha.

$214,900
ACTIVE Status
Welcome HOME to Highland Estates in Pleasant Prairie where community, lifestyle, and location come together! You're close to schools, shopping, restaurants, recreation and minutes to Lake Michigan shoreline....while still coming home to a peaceful neighborhood with plenty of open space. LOT 84 includes 15,958 square feet! Highland Estates...A place where you know your neighbors, where families grow, friendships are made, and the little everyday moments become some of your favorite memories. Conveniently located in between MKE and Chicago! Minutes to Interstate 94! This is more than a place to live. It's a place to call home!!!! DON'T WAIT!

Lt84 50th Court, Pleasant Prairie

Listing courtesy of EXP Realty, LLC Kenosha.

$209,900
ACTIVE Status
FINALLY! YOU'VE WAITED FOR A NEW HOME IN PLEASANT PRAIRIE! Welcome HOME to Highland Estates in Pleasant Prairie where community, lifestyle, and location come together! You're close to schools, shopping, restaurants, recreation and minutes to Lake Michigan shoreline....while still coming home to a peaceful neighborhood with plenty of open space. LOT 81 includes 15,447 square feet!Highland Estates...A place where you know your neighbors, where families grow, friendships are made, and the little everyday moments become some of your favorite memories. Conveniently located in between MKE and Chicago! Minutes to Interstate 94! This is more than a place to live. It's a place to call home!!!! DON'T WAIT!

Lt81 50th Court, Pleasant Prairie

Listing courtesy of EXP Realty, LLC Kenosha.

$239,900
ACTIVE Status
Welcome HOME to Highland Estates in Pleasant Prairie where community, lifestyle, and location come together! You're close to schools, shopping, restaurants, recreation and minutes to Lake Michigan shoreline....while still coming home to a peaceful neighborhood with plenty of open space. LOT 80 includes 18,160 square feet!Highland Estates...A place where you know your neighbors, where families grow, friendships are made, and the little everyday moments become some of your favorite memories. Conveniently located in between MKE and Chicago! Minutes to Interstate 94! This is more than a place to live. It's a place to call home!!!! DON'T WAIT!

Lt80 Highland Place, Pleasant Prairie

Listing courtesy of EXP Realty, LLC Kenosha.

$2,500,000
ACTIVE Status
Approximately 8.69 acres with two PINs offering exceptional investment and development potential along the Highway 50 corridor. Nearly 440 feet of frontage provides outstanding visibility in a rapidly growing commercial area near Green Bay Rd. Existing farmhouse is set well back from the highway and may provide interim residential, rental, or office use while future plans are developed. Agricultural acreage is currently farmed by a neighboring farmer. Opportunity may be enhanced through assemblage with neighboring properties for increased size and additional access. Recent survey available. Seller may consider terms.

7115 75th Street, Pleasant Prairie

Listing courtesy of Keller Williams North Shore West.

$189,900
ACTIVE Status
Located in the heart of Pleasant Prairie, Cedar Ridge offers a serene and welcoming environment with a perfect blend of nature and convenience. This picturesque neighborhood features spacious, fully improved lots with municipal water and sewer services. The community is surrounded by green spaces and offers easy access to local amenities, including nearby shopping, dining, and recreational options. Cedar Ridge is just minutes from major highways, making commuting to surrounding cities effortless. Experience the tranquility of suburban living with the convenience of urban amenities just a short drive away. Lot 26 offers a walkout exposure with pond frontage.

Lt26 Cedar Ridge Court, Pleasant Prairie

Listing courtesy of Korndoerfer Homes LLC.

$8,575,000
ACTIVE Status
prime land for future development on the SE Corner of Hwy 31 & 165also includes the parcel located at 10540 Old Green Bay Rd

10630 Old Green Bay Road, Pleasant Prairie

Listing courtesy of Pitts Brothers & Associates, LLC.

$249,000
ACTIVE Status
Lake Michigan defines this pristine Carol Beach Estates lot. Lake Michigan moderates the air, for cooler Summers and warmer Winters. Lake Michigan stuns with wonderful vistas over more than 320' of unbuilt lake shore across the road (not included). Abutting and amid State-owned conservancy, an ample green buffer from neighbors comes at no extra cost...priceless! Commute to Chicago's Loop by rail from Kenosha or Waukegan. Owner attests wetland conditions do not exist on property nor does the floodplain. Per the Village buildablity is the responsibility of the Owner, who says It's fully buildable!!!

Lt15,Bk34 Lakeshore Drive, Pleasant Prairie

Listing courtesy of Lake to Lake Realty LLC.

$569,900
ACTIVE Status
Two adjacent parcels totaling approximately 17.95 acres in desirable Pleasant Prairie, WI offer an incredible opportunity for a private homestead, hobby farm, or future development. Parcel 1 consists of 8.95 acres and Parcel 2 consists of 9.0 acres. Currently zoned Residential, this property provides flexibility for a variety of potential uses while still offering the peace and space of country living. Enjoy the chance to build your dream home, establish a private retreat, or explore development possibilities. All data and information sourced from Kenosha County Interactive Mapping. Buyer responsible for verifying all information.

Lt0 93rd Street, Pleasant Prairie

Listing courtesy of @properties.

$209,900
ACTIVE Status
Highland Estates offers the perfect blend of everyday convenience and peaceful neighborhood charm in beautiful Pleasant Prairie. Ideally located just 2 miles from the WI-IL border and approx. 3.5 miles from I-94, the community provides easy access to both Milwaukee and Chicago. Residents enjoy proximity to the RecPlex, Pleasant Prairie Premium Outlets, Lake Michigan, parks, trails, dining, and golf. Located in the Kenosha Unified School District, Highland Estates is a place where life feels relaxed, comfortable, and connected. Per the Master Declaration of Restrictions for Highland Estates, construction must begin within one year of closing.

Lt100 49th Court, Pleasant Prairie

Listing courtesy of Korndoerfer Homes LLC.

Copyright 2026 WIREX Multiple Listing Service. All rights reserved. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All information is deemed reliable, but not guaranteed. Information is supplied by seller and other third parties and has not been verified.

Copyright 2026 WIREX Multiple Listing Service. All rights reserved. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All information is deemed reliable, but not guaranteed. Information is supplied by seller and other third parties and has not been verified.