197

Pleasant Prairie, WI Homes for Sale

Section Image Section Image
  • /10

    $199,900

    • Land
    • 13,503 Sq Ft
    • $644,839 per Acre

    Lt107 Highland Place, Pleasant Prairie, WI 53158

    Welcome to Highland Estate Development, Pleasant Prairie's most exciting new residential community! Lot 107 is a generously sized homesite offering 13,698 square feet with spacious viewsperfect for bringing your dream home to life. Phase 1 is officially underway, giving you the opportunity to bring your own builder or work with one of our trusted partners. Designed with lifestyle and livability

    Scott Gettleman Keller Williams North Shore West

    Lt107 Highland Place, Pleasant Prairie, WI 53158
  • /30

    $499,900

    Open Sun 11AM - 2PM
    • 3 Beds
    • 2 Baths
    • 1,614 Sq Ft

    8791 83rd Place, Pleasant Prairie, WI 53158

    First time on the market. Lovely one owner home in Pleasant Prairie awaits new owners. 3 bedrooms, 2 full baths, open concept, stainless steel appliances, 1st floor laundry. Full basement with full size windows perfect for adding additional square footage. Backyard features large composite deck, nicely landscaped with plenty of mature trees. This is an estate.

    Douglas Jackson RE/MAX ELITE

    8791 83rd Place, Pleasant Prairie, WI 53158
  • /25

    $249,900

    Pending
    • 2 Beds
    • 2 Baths
    • 1,170 Sq Ft

    6709 102nd St Unit 9AA, Pleasant Prairie, WI 53158

    WOW!! Location, Location describe this sought after 1st Floor Condo in Highly Desirable Pleasant Prairie. This BEAUTY of a Condo in the Meadowlands complex features 9 Ft Ceilings, A Huge Master Bedroom w/Walk-in Closets and a Master Bathroom. This BEAUTY also boasts a generous sized second bedroom w/Sliding Door to step out onto your Patio for your Coffee on a warm summer day in the morning or

    Gary Frederick Epique Realty

    6709 102nd St Unit 9AA, Pleasant Prairie, WI 53158
  • /48

    $630,000

    • 3 Beds
    • 2.5 Baths
    • 2,792 Sq Ft

    8108 E Ridge Dr, Pleasant Prairie, WI 53158

    Welcome to this spacious 2,792 sq. ft. ranch where comfort, updates, and year-round fun come together. Featuring new windows, a newer roof, and updated A/C, this home offers peace of mind from day one. The true showstopper is the indoor swimming pool--perfect for entertaining, relaxing, exercising, or enjoying a private retreat no matter the season. With generous living space and a unique amenity

    Bradley Lois RE/MAX Premier Properties

    8108 E Ridge Dr, Pleasant Prairie, WI 53158
  • /9

    $239,900

    • Land
    • 18,295 Sq Ft
    • $571,190 per Acre

    Lt 80 Highland Place, Pleasant Prairie, WI 53158

    Welcome to Highland Estate Development, Pleasant Prairie's most exciting new residential community! Lot 80 is a generously sized corner homesite offering over 18,160 square feet with spacious views-perfect for bringing your dream home to life. Phase 1 is officially underway, giving you the opportunity to bring your own builder or work with one of our trusted partners. Designed with lifestyle and

    Scott Gettleman Keller Williams North Shore West

    Lt 80 Highland Place, Pleasant Prairie, WI 53158
  • /2

    $209,900

    • Land
    • 14,810 Sq Ft
    • $617,353 per Acre

    Lt105 Highland Place, Pleasant Prairie, WI 53158

    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

    Nicole Clark Korndoerfer Homes LLC

    Lt105 Highland Place, Pleasant Prairie, WI 53158
  • /5

    $249,000

    • Land
    • 11,325 Sq Ft
    • $957,692 per Acre

    Lt15,Bk34 Lakeshore Dr, Pleasant Prairie, WI 53158

    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

    Shiela Heg Lake to Lake Realty LLC

    Lt15,Bk34 Lakeshore Dr, Pleasant Prairie, WI 53158
  • /77

    $1,249,700

    $125K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 6,946 Sq Ft

    11641 Old Green Bay Rd, Pleasant Prairie, WI 53158

    BREATHTAKING Newer Const., on 1 acre in coveted Pleasant Prairie, waiting for YOU! Home features almost 7000 sq ft!! Lg master sanctuary & ensuite w/dual vanity, quartz tops, stand alone tub, tiled walk-in show. & luxurious custom-built walk in closets. Chef's Kit. quartz tops. Bosh app. walk-in pantry. 4 add. BR, one on MF, one w/private ensuite. Massive 2 story Living w/gorgeous FP. LVP

    Karen Brown RE/MAX ELITE

    11641 Old Green Bay Rd, Pleasant Prairie, WI 53158
  • /28

    $379,900

    $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,472 Sq Ft

    10034 28th Ave, Pleasant Prairie, WI 53158

    Just listed in Pleasant Prairie! This updated 3-bedroom, 2-bath home sits on a spacious .76-acre lot and offers an open-concept layout with a bright living room flowing into the eat-in kitchen. The large primary bedroom features a private bathroom and generous closet space. Recent updates include new luxury vinyl plank flooring (2026), new roofs on the house and detached 2.5-car garage (2025),

    Alivia Londre Londre Real Estate and Property Management

    10034 28th Ave, Pleasant Prairie, WI 53158
  • /14

    $574,140

    New Construction $5K PRICE INCREASE
    • 4 Beds
    • 2 Baths
    • 2,386 Sq Ft

    9412 53rd Ave, Pleasant Prairie, WI 53158

    The entryway leads to the first level of this new two-story home, where a versatile living room can be found off the foyer while the family room, dining room and kitchen share an open-concept design for seamless everyday living. Upstairs, four bedrooms provide enough space for a growing family.

    Lennar Builder
    9412 53rd Ave, Pleasant Prairie, WI 53158
  • /31

    $569,900

    New Construction $40K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,850 Sq Ft

    12212 Sheridan Rd, Kenosha, WI 53158

    Brand New 3 Bedroom 2.5 bath Ranch in Pleasant Prairie. Home offers a large master bedroom with Tray ceiling large walk-in closet a master on suite with Double vanities with quartz top, Kitchen offers slow shut doors and drawers, stainless steel appliances, nice large Island and a pantry. 1st Floor laundry. Garage has 220V electric car outlet.

    Douglas Anderson Epique Realty

    12212 Sheridan Rd, Kenosha, WI 53158
  • /16

    $441,900

    $10K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,434 Sq Ft

    9200 66th Ave Unit 124, Pleasant Prairie, WI 53158

    Nestled in the heart of Pleasant Prairie, Creekside Crossing Condominiums offers beautifully designed units, each tailored for luxury and comfort. These condominiums feature modern amenities, refined finishes, 9' ceilings, and an open floor plan. This specific condo also includes a full basement and pond view. Located in a serene neighborhood with convenient access to local attractions, Creekside

    Todd Stanich Stanich Realty, LLC

    9200 66th Ave Unit 124, Pleasant Prairie, WI 53158
  • /10

    $239,900

    • Land
    • 18,295 Sq Ft
    • $571,190 per Acre

    Lt80 Highland Place, Pleasant Prairie, WI 53158

    Welcome to Highland Estate Development, Pleasant Prairie's most exciting new residential community! Lot 80 is a generously sized corner homesite offering over 18,160 square feet with spacious viewsperfect for bringing your dream home to life. Phase 1 is officially underway, giving you the opportunity to bring your own builder or work with one of our trusted partners. Designed with lifestyle and

    Scott Gettleman Keller Williams North Shore West

    Lt80 Highland Place, Pleasant Prairie, WI 53158
  • /26

    $574,990

    New Construction $5K PRICE INCREASE
    • 4 Beds
    • 2.5 Baths
    • 2,608 Sq Ft

    Wren Plan at Highland Estates, Pleasant Prairie, WI 53158

    This two-story home combines modern comfort with convenience. Found off the foyer is a flex space for versatile needs, followed by a cohesive open main living area with direct access to the backyard for indoor-outdoor activities. In a private corner of the first floor is a study ideal for at-home work. Upstairs are three secondary bedrooms and the spacious owner’s suite with a full-sized bathroom.

    Lennar Builder
    5315 94th St Unit 40753948, Pleasant Prairie, WI 53158
  • /9

    $199,900

    • Land
    • 13,503 Sq Ft
    • $644,839 per Acre

    Lt 107 Highland Place, Pleasant Prairie, WI 53158

    Welcome to Highland Estate Development, Pleasant Prairie's most exciting new residential community! Lot 107 is a generously sized homesite offering 13,698 square feet with spacious views-perfect for bringing your dream home to life. Phase 1 is officially underway, giving you the opportunity to bring your own builder or work with one of our trusted partners. Designed with lifestyle and livability

    Scott Gettleman Keller Williams North Shore West

    Lt 107 Highland Place, Pleasant Prairie, WI 53158
  • /8

    $249,900

    • Land
    • 19,166 Sq Ft
    • $567,955 per Acre

    Lt 82 50th Ct, Pleasant Prairie, WI 53158

    Welcome to Highland Estate Development, Pleasant Prairie's most exciting new residential community! Lot 82 is a generously sized parcel offering 19,319 square feet with spacious views, ideally situated on a quiet cul-de-sac-perfect for bringing your dream home to life. Phase 1 is officially underway, giving you the opportunity to bring your own builder or work with one of our trusted partners.

    Scott Gettleman Keller Williams North Shore West

    Lt 82 50th Ct, Pleasant Prairie, WI 53158
  • /9

    $209,900

    Pending
    • Land
    • 15,246 Sq Ft
    • $599,714 per Acre

    Lt 88 49th Ct, Pleasant Prairie, WI 53158

    Welcome to Highland Estate Development, Pleasant Prairie's most exciting new residential community! Lot 88 is a generously sized homesite offering 15,156 square feet and scenic views of the nearby retention pond-an ideal setting to bring your vision to life. Phase 1 is officially underway, giving you the opportunity to bring your own builder or work with one of our trusted partners. Thoughtfully

    Scott Gettleman Keller Williams North Shore West

    Lt 88 49th Ct, Pleasant Prairie, WI 53158
  • /2

    $399,900

    $100K PRICE DROP
    • Land
    • 3.4 Acres
    • $117,618 per Acre

    Lt0 Green Bay Rd, Kenosha, WI 53158

    In the path of much future progress. High visibility and 2 separate accesses to property. This is ready for your new building!!! 3+ acres is available, and the possibilities are endless.

    Melissa Roach-Zievers RE/MAX ELITE

    Lt0 Green Bay Rd, Kenosha, WI 53158
  • /10

    $209,900

    • Land
    • 15,681 Sq Ft
    • $583,056 per Acre

    Lt96 49th Ct, Pleasant Prairie, WI 53158

    Welcome to Highland Estate Development, Pleasant Prairie's most exciting new residential community! Lot 96 is a generously sized homesite offering over 15,481 square feet with spacious views, ideally situated on a quiet cul-de-sacperfect for bringing your dream home to life. Phase 1 is officially underway, giving you the opportunity to bring your own builder or work with one of our trusted

    Scott Gettleman Keller Williams North Shore West

    Lt96 49th Ct, Pleasant Prairie, WI 53158
  • /57

    $629,000

    $32K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,916 Sq Ft

    8715 108th Ave, Pleasant Prairie, WI 53158

    Highly desirable River Oaks Subdivision, this home perfectly situated on private yard backing to protected natural land. This property includes full access to River Oaks Lake Russo & Park, within walking distance. 4 bedroom 3-1/2 bath home has wood floors throughout and a spacious great room addition with Cathedral ceilings and walls of windows that fill the space with natural light and showcase

    Sheri Clark Southport Realty

    8715 108th Ave, Pleasant Prairie, WI 53158
  • /10

    $184,990

    $7K PRICE INCREASE
    • Land
    • 19,166 Sq Ft
    • $420,432 per Acre

    Lt25 Cedar Ridge Ct, Pleasant Prairie, WI 53158

    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

    Nicole Clark Korndoerfer Homes LLC

    Lt25 Cedar Ridge Ct, Pleasant Prairie, WI 53158
  • /10

    $215,900

    • Land
    • 16,117 Sq Ft
    • $583,514 per Acre

    Lt104 Highland Place, Pleasant Prairie, WI 53158

    Welcome to Highland Estate Development, Pleasant Prairie's most exciting new residential community! Lot 104 is a generously sized homesite offering over 16,127 square feet and spacious viewsan ideal setting to bring your vision to life. Phase 1 is officially underway, giving you the opportunity to bring your own builder or work with one of our trusted partners. Thoughtfully designed with

    Scott Gettleman Keller Williams North Shore West

    Lt104 Highland Place, Pleasant Prairie, WI 53158
  • /14

    $49,999

    $15K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft

    7801 88th St Unit 171, Pleasant Prairie, WI 53158

    Must see this well-maintained manufactured home in Westwood Estates in desirable Pleasant Prairie! This 3BR, 2 full bath home features a spacious living room open to the kitchen with an eat-in area. Affordable monthly costs: sewer/well approx. $25–$35 and personal property tax approx. $17. Pet-friendly community allows up to 2 pets (1 cat/1 dog or 2 cats; dogs subject to HOA approval, no breed

    Chris Slinker Berkshire Hathaway HomeServices Water City Realty

    7801 88th St Unit 171, Pleasant Prairie, WI 53158
  • /24

    $230,000

    • 2 Beds
    • 2 Baths
    • 1,080 Sq Ft

    8200 Lexington Place Unit 12, Pleasant Prairie, WI 53158

    Second floor, 2 bedroom, 2 bath open concept condo with great balcony view. Just south of Hwy 50 easy access to I-94 and shopping and restaurants. Offering a country feel and green space park in the middle of the cul de sac outside the building. Vaulted living room ceiling with wood floors. Newer washer, dryer, dishwasher, and light fixtures. 1/1/2 attached garage with opener at the back of the

    Susan Anderson Shorewest Realtors, Inc.

    8200 Lexington Place Unit 12, Pleasant Prairie, WI 53158
  • /50

    $749,900

    • 4 Beds
    • 3.5 Baths
    • 3,214 Sq Ft

    4388 86th St, Kenosha, WI 53142

    Beautifully maintained home in sought after Pleasant Prairie offering oversized living spaces, thoughtful updates throughout, and a resort style backyard that backs up to open space. This home perfectly blends comfort, functionality, and outdoor enjoyment. Featuring bamboo flooring, new carpet (2025), updated kitchen (2021), private backyard with in-ground pool (new liner in 2021), expansive

    Lisa Fabiano EXP Realty, LLC Kenosha

    4388 86th St, Kenosha, WI 53142
  • /10

    $209,900

    • Land
    • 15,681 Sq Ft
    • $583,056 per Acre

    Lt 96 49th Ct, Pleasant Prairie, WI 53158

    Welcome to Highland Estate Development, Pleasant Prairie's most exciting new residential community! Lot 96 is a generously sized homesite offering over 15,481 square feet with spacious views, ideally situated on a quiet cul-de-sac-perfect for bringing your dream home to life. Phase 1 is officially underway, giving you the opportunity to bring your own builder or work with one of our trusted

    Scott Gettleman Keller Williams North Shore West

    Lt 96 49th Ct, Pleasant Prairie, WI 53158
  • /28

    $490,000

    • 3 Beds
    • 4 Baths
    • 2,678 Sq Ft

    4258 91st Place, Kenosha, WI 53142

    Very rare, side by side, 2 story condo in Pleasant Prairie! Beautifully landscaped, extremely well maintained & packed with character. Riveting pride of ownership. Huge great room w vaulted ceilings, gas fireplace, picturesque staircase, & large windows. Natural light beams into the eat-in kitchen; complete w tasteful wood cabinets, tons of counterspace, & room for kitchen table. Spend most of

    Zach Ostergaard Realty ONE Group Boardwalk

    4258 91st Place, Kenosha, WI 53142
  • /26

    $750,000

    Under Contract
    • 4 Beds
    • 2.5 Baths
    • 2,267 Sq Ft

    8610 Lakeshore Dr, Pleasant Prairie, WI 53158

    This Craftsman-style ranch in the Carol Beach Estates subdivision of Pleasant Prairie sits on a corner lot just steps from Lake Michigan. The open-concept main level features a kitchen with white cabinetry, granite countertops, stainless steel appliances, and a large island with breakfast bar. The living room offers a cathedral ceiling, recessed lighting, gas fireplace, and access to the

    Jackson Sanderson Berkshire Hathaway HomeServices Chicago

    8610 Lakeshore Dr, Pleasant Prairie, WI 53158
  • /10

    $180,990

    $8K PRICE INCREASE
    • Land
    • 19,166 Sq Ft
    • $411,341 per Acre

    Lt19 Cedar Ridge Ct, Pleasant Prairie, WI 53158

    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

    Kim Maksimik Korndoerfer Homes LLC

    Lt19 Cedar Ridge Ct, Pleasant Prairie, WI 53158
  • /26

    $541,990

    New Construction $5K PRICE INCREASE
    • 4 Beds
    • 2.5 Baths
    • 2,193 Sq Ft

    Starling Plan at Highland Estates, Pleasant Prairie, WI 53158

    This two-story home provides modern comfort and ample room to grow. Upon entry is a flex room well-suited for hosting guests, followed by a spacious open layout for seamless family living and relaxing. Separate from the downstairs main living area, the second level hosts all four bedrooms to provide great personal space and privacy. The sprawling owner’s suite is a serene haven with a full-sized

    Lennar Builder
    5315 94th St Unit 40753951, Pleasant Prairie, WI 53158
  • /10

    $209,900

    • Land
    • 15,246 Sq Ft
    • $599,714 per Acre

    Lt99 49th Ct, Pleasant Prairie, WI 53158

    Welcome to Highland Estate Development, Pleasant Prairie's most exciting new residential community! Lot 99 is a generously sized homesite offering over 15,078 square feetan ideal setting to bring your vision to life. Phase 1 is officially underway, giving you the opportunity to bring your own builder or work with one of our trusted partners. Designed with lifestyle and livability in mind,

    Scott Gettleman Keller Williams North Shore West

    Lt99 49th Ct, Pleasant Prairie, WI 53158
  • /22

    $239,900

    Pending
    • 2 Beds
    • 2 Baths
    • 1,080 Sq Ft

    8055 Lexington Place Unit 12, Pleasant Prairie, WI 53158

    Welcome to this private-entry, second-floor luxury condominium featuring 2 bedrooms and 2 full bathrooms, ideally located in the highly desirable Lexington Village community. Enjoy peaceful views of a tranquil lake and backyard from your private balcony. Has been extensively updated with High quality new carpeting and flooring throughout, along with fresh, whole-house interior paint. The

    Guangfu Jia Harbin Realty Management LLC

    8055 Lexington Place Unit 12, Pleasant Prairie, WI 53158
  • /2

    $249,900

    • Land
    • 24,393 Sq Ft
    • $446,250 per Acre

    Lt17 29th St, Kenosha, WI 53142

    1 of 2 extremely private cul de sac lots with over .5 acres. Nestled in the newly approved Tirawoods Subdivision on Kenosha's desirable Northside, this exceptional lot offers the freedom to build with the builder of your choice. Several lots are available, including options ideal for daylight and walk-out basements. Enjoy rare privacy with over 8 acres of vacant land stretching behind the

    AJ Swartz Berkshire Hathaway Home Services Epic Real Estate

    Lt17 29th St, Kenosha, WI 53142
  • /39

    $639,000

    Under Contract
    • 4 Beds
    • 2.5 Baths
    • 2,199 Sq Ft

    9026 62nd Ave, Pleasant Prairie, WI 53158

    Desirable 4-bedroom, 2.5-bath home in sought-after Pleasant Prairie offering space, comfort, and an exceptional layout! A welcoming foyer opens to a formal living room and dining room, perfect for entertaining or everyday living. The inviting family room showcases a stunning floor-to-ceiling stone fireplace and flows seamlessly into the eat-in kitchen. Upstairs, enjoy 4 generous bedrooms,

    Laura Stoner Keller Williams Milwaukee South Shore

    9026 62nd Ave, Pleasant Prairie, WI 53158
  • /10

    $209,900

    • Land
    • 15,246 Sq Ft
    • $599,714 per Acre

    Unlisted Address

    Welcome to Highland Estate Development, Pleasant Prairie's most exciting new residential community! Lot 94 is a generously sized homesite offering over 15,248 square feet with spacious views, ideally situated on a quiet cul-de-sac-perfect for bringing your dream home to life. Phase 1 is officially underway, giving you the opportunity to bring your own builder or work with one of our trusted

    Scott Gettleman Keller Williams North Shore West

    Unlisted Address
  • /4

    $114,000

    • 3 Beds
    • 2 Baths
    • 1,141 Sq Ft

    7801 88th Ave Unit 62, Pleasant Prairie, WI 53158

    Welcome to Westwood Estates, an all age active and vibrant community, where you can find yourself in your dream home. We have a stunning, brand new, 2025 3 bed, 2 bath home for sale featuring 1141 sq ft of beautifully designed living space. Located in Pleasant Prairie, this property offers the perfect blend of modern amenities and timeless charm. Step inside to find an open-concept floor plan,

    Amanda Zambrano_Gomez Westwood Estates

    7801 88th Ave Unit 62, Pleasant Prairie, WI 53158
  • /31

    $514,900

    $20K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,856 Sq Ft

    8004 103rd Ave, Pleasant Prairie, WI 53158

    New Price on this Prestigious Prairie Ridge subdivision. Larger 4 bed, 3.5 bath home. situated on top of circle and ready for immediate occupancy. Finished rec room with full bath adds for additional living space. Nice patio for outdoor entertaining, eat-in kitchen, gas fireplace in family room, formal dining and living rooms. 1st floor laundry, and super large primary suite on upper level.

    Melissa Roach-Zievers RE/MAX ELITE

    8004 103rd Ave, Pleasant Prairie, WI 53158
  • /34

    $549,900

    $10K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,700 Sq Ft

    4401 122nd St, Pleasant Prairie, WI 53158

    Well-maintained and ideal Pleasant Prairie location, this 2,700 SF home offers comfort, functionality, and everyday convenience. Step inside to a bright, inviting layout with spacious living areas and a natural flow perfect for both relaxing and entertaining. The kitchen with island provides ample cabinet space and connects seamlessly to the main living area. Generous sized 3 bedrooms offer

    Thomas Sauer Lake Country Flat Fee

    4401 122nd St, Pleasant Prairie, WI 53158

Showing Results 81 - 120, Page 3 of 5

How to Buy a Home How to Finance a Home How to Sell a Home