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Westside Homes for Sale

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  • /33

    $360,000

    • 3 Beds
    • 2.5 Baths
    • 2,105 Sq Ft

    2524 Leopold Way Unit 7, Sun Prairie, WI 53590

    This home is ready for someone to make it their own while taking advantage of a great opportunity in Sun Prairie's sought-after Smith's Crossing neighborhood! This 3-bed, 2.5-bath condo offers a spacious living room with hardwood floors, 9' ceilings, and a cozy fireplace. The kitchen is loaded with cabinets, stainless steel appliances, a breakfast bar, a pantry, and ample counter space. Upstairs

    Agent Photo

    Jamie Foley

    Relish Realty

    (608) 470-6580

    2524 Leopold Way Unit 7, Sun Prairie, WI 53590
  • /28

    $565,000

    • 3 Beds
    • 2 Baths
    • 1,650 Sq Ft

    338 Bella Way, Sun Prairie, WI 53590

    Welcome to this lovely ranch home in the popular Ironwood Estates! Location is everything, and this neighborhood delivers. Enjoy the convenience of being within walking distance to the local elementary, middle, and high school. Commuters will appreciate the quick access to the interstate and airport, while everyday errands are simplified with endless shopping and dining options just moments away.

    Agent Photo

    Debbie Lindquist

    Keller Williams Lake Country

    (608) 447-6269

    338 Bella Way, Sun Prairie, WI 53590
  • /44

    $499,000

    • 4 Beds
    • 3.5 Baths
    • 2,456 Sq Ft

    2418 Leopold Way, Sun Prairie, WI 53590

    Enjoy stunning views of a nature preserve, pond, and Thoreau Park-one of the few homes in Smiths Crossing that offers this rare backdrop! Main level boasts an open-concept kitchen complete w/ quartz countertops, SS appliances, a sleek hood vent, and spacious island w/ breakfast bar seating. Just off the entryway, you'll find a flexible bonus room & stylish half bath, all enhanced by beautiful LVP

    Andy Kramer Redfin Corporation

    2418 Leopold Way, Sun Prairie, WI 53590
  • /31

    $379,900

    • 3 Beds
    • 3.5 Baths
    • 2,002 Sq Ft

    2537 New Town Dr, Sun Prairie, WI 53590

    Conveniently located just minutes from historic downtown Sun Prairie, Prairie Lakes shopping, east side of Madison and 15 minutes to downtown Madison, this modern, well-maintained townhome offers comfort and style! Features include 9-ft ceilings, gorgeous wood floors, gas fireplace with beautiful mantel, quartz counters, stainless steel appliances, and breakfast bar; the dining area rounds out

    Jason Fowler Century 21 Affiliated

    2537 New Town Dr, Sun Prairie, WI 53590
  • /57

    $500,000 Open Sun 12PM - 1:30PM

    • 3 Beds
    • 2 Baths
    • 1,577 Sq Ft

    1261 Crane Meadow Way, Sun Prairie, WI 53590

    Back on the market at no fault to the seller. Wow!! Built in 2022 & handled with love & care! Stepping inside this 3-bedroom ranch feels like you're in a brand new home. You'll enjoy 9' ceilings & an abundance of natural light throughout. An open concept floor plan offers split bedrooms for maximum convenience. Gorgeous, large kitchen featuring island, quartz countertops, shaker-style cabinets.

    Chanell Abing Coldwell Banker Real Estate Group

    1261 Crane Meadow Way, Sun Prairie, WI 53590
  • /2

    $519,900

    • 4 Beds
    • 3 Baths
    • 2,456 Sq Ft

    167 N Heatherstone Dr, Sun Prairie, WI 53590

    Showings start 8/28. More pictures coming. Located in the desirable Weybridge subdivision, this exceptional ranch-style home offers an abundance of space & natural light. The main level features three bedrooms, including a primary suite with a luxurious, spa-inspired bathroom & a generous walk-in closet. A dedicated laundry room offers ample storage space. The contemporary kitchen is accented by

    Gail Rutkowski Century 21 Affiliated

    167 N Heatherstone Dr, Sun Prairie, WI 53590
  • /2

    $559,900 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,078 Sq Ft

    1221 Orchid Petal Dr, Sun Prairie, WI 53590

    Move-in Ready 11/5/25! This Everest home features a smart, open layout and checks off all your boxes. 4 bedrooms, 2.5 baths with locally crafted cabinetry, and painted trim and doors throughout. Gourmet kitchen w/ island and stainless appliances. Owner’s Suite has a private bath, walk-in closet, and tray ceiling. 2-car garage. Retreat to your deck for some R&R. To top it off, this home offers a

    Paul Treige Stark Company, REALTORS

    1221 Orchid Petal Dr, Sun Prairie, WI 53590
  • /18

    $574,900 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,033 Sq Ft

    2564 Koshkonong Way, Sun Prairie, WI 53590

    Image is representative of home; colors may vary.All prices, promotions and specifications are subject to change at any time without notice based on the discretion of Veridian Homes.

    Builder Photo

    Veridian Homes

    Builder

    2564 Koshkonong Way, Sun Prairie, WI 53590
  • /18

    $524,900 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,861 Sq Ft

    1133 Hickory Hills Dr, Sun Prairie, WI 53590

    Image is representative of home; colors may vary.All prices, promotions and specifications are subject to change at any time without notice based on the discretion of Veridian Homes.

    Builder Photo

    Veridian Homes

    Builder

    1133 Hickory Hills Dr, Sun Prairie, WI 53590
  • /18

    $509,900 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,647 Sq Ft

    2560 Water Lily Cir, Sun Prairie, WI 53590

    Image is representative of home; colors may vary.All prices, promotions and specifications are subject to change at any time without notice based on the discretion of Veridian Homes.

    Builder Photo

    Veridian Homes

    Builder

    2560 Water Lily Cir, Sun Prairie, WI 53590
  • /20

    $599,900 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,203 Sq Ft

    2535 Water Lily Cir, Sun Prairie, WI 53590

    Image is representative of home; colors may vary.All prices, promotions and specifications are subject to change at any time without notice based on the discretion of Veridian Homes.

    Builder Photo

    Veridian Homes

    Builder

    2535 Water Lily Cir, Sun Prairie, WI 53590
  • /68

    $522,500 New Construction

    • 3 Beds
    • 2 Baths
    • 1,572 Sq Ft

    The Harlow Plan at Smiths Crossing - Smith's Crossing McCoy Addition, Sun Prairie, WI 53590

    One look at the owner’s suite in The Harlow and you’ll feel your pulse quicken... Featuring a private bath and a closet big enough to dance in. The kitchen showcases a large island for entertaining and a sunny set of patio doors for a quiet cup of coffee before your busy day begins. Welcome home to The Harlow.All prices, promotions and specifications are subject to change at any time

    Builder Photo

    Veridian Homes

    Builder

    1207 Crane Meadow Way Unit 36789014, Sun Prairie, WI 53590
  • /4

    $537,500 New Construction

    • 3 Beds
    • 2 Baths
    • 1,764 Sq Ft

    The Cooper Plan at Smiths Crossing - Smith's Crossing, Sun Prairie, WI 53590

    You don’t need to be a Texan to own a ranch. Wisconsinites make excellent ranchers too. Round up guests at the kitchen island for an elaborately prepared amuse-bouche paired with the perfect wine. Corral family pets in the mudroom for a quick wipe off before entering the homestead. Then, kick off your cowboy boots and relax, because there won’t be any hills to climb while you’re at home.

    Builder Photo

    Veridian Homes

    Builder

    1207 Crane Meadow Way Unit 36789031, Sun Prairie, WI 53590
  • /6

    $541,400 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,045 Sq Ft

    The Hoffman Plan at Smiths Crossing - Smith's Crossing, Sun Prairie, WI 53590

    Calling all cooks, Booklovers and Decorators! Go ahead, line the shelves with those classic Mark Twain novels or one-of-a-kind treasures. Load up that roomy kitchen with gourmet pans and obscure gadgets. With more space, means more luxury. Meet The Hoffman.All prices, promotions and specifications are subject to change at any time without notice based on the discretion of Veridian Homes.

    Builder Photo

    Veridian Homes

    Builder

    1207 Crane Meadow Way Unit 36789037, Sun Prairie, WI 53590
  • /4

    $515,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,650 Sq Ft

    The Emerald Plan at Smiths Crossing - Smith's Crossing McCoy Addition, Sun Prairie, WI 53590

    Ideal for gatherings, gadgets and relaxation. The Emerald offers smart features that cater to your every need. Congregate with family around the kitchen island, dock your devices at the Daily Station and re-charge yourself in its impressive Owner’s Suite.All prices, promotions and specifications are subject to change at any time without notice based on the discretion of Veridian Homes.

    Builder Photo

    Veridian Homes

    Builder

    1207 Crane Meadow Way Unit 36450354, Sun Prairie, WI 53590
  • 2543 Water Lily Cir, Sun Prairie, WI 53590

    $519,900 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,861 Sq Ft

    2543 Water Lily Cir, Sun Prairie, WI 53590

    Image is representative of home; colors may vary.All prices, promotions and specifications are subject to change at any time without notice based on the discretion of Veridian Homes.

    Builder Photo

    Veridian Homes

    Builder

    2543 Water Lily Cir, Sun Prairie, WI 53590
  • 2553 Koshkonong Way, Sun Prairie, WI 53590

    $539,900 New Construction

    • 3 Beds
    • 2 Baths
    • 1,572 Sq Ft

    2553 Koshkonong Way, Sun Prairie, WI 53590

    Image is representative of home; colors may vary.All prices, promotions and specifications are subject to change at any time without notice based on the discretion of Veridian Homes.

    Builder Photo

    Veridian Homes

    Builder

    2553 Koshkonong Way, Sun Prairie, WI 53590
  • 1157 Hickory Hills Dr, Sun Prairie, WI 53590

    $519,900 New Construction

    • 3 Beds
    • 2 Baths
    • 1,584 Sq Ft

    1157 Hickory Hills Dr, Sun Prairie, WI 53590

    Image is representative of home; colors may vary.All prices, promotions and specifications are subject to change at any time without notice based on the discretion of Veridian Homes.

    Builder Photo

    Veridian Homes

    Builder

    1157 Hickory Hills Dr, Sun Prairie, WI 53590
  • /49

    $420,000

    • 3 Beds
    • 4 Baths
    • 1,962 Sq Ft

    1475 Wild Iris St, Sun Prairie, WI 53590

    Welcome to Smith's Crossing! Beautiful 3 bedroom 2 story home nestled just a block away from walking trails, playground, and green space at Thoreau Park. Enter inside to find an open concept floor plan w/ living room and well appointed kitchen w/ all stainless steel appliances, tile backsplash, breakfast bar/island & dining area w/ walkout to wood deck - great for grilling. Upstairs enjoy all 3

    Kaitlin Solomon MHB Real Estate

    1475 Wild Iris St, Sun Prairie, WI 53590
  • /44

    $389,900

    • 3 Beds
    • 3 Baths
    • 2,150 Sq Ft

    3095 Rebel Dr, Sun Prairie, WI 53590

    Move-in ready, meticulously maintained Ranch-style condo is ready for its next owner! Enter inside to find soaring vaulted ceilings w/ skylights allowing natural light to fill living rm w/ cozy gas fp & kitchen boasting updated corian counters, SS apps, & dining area w/ walkout to sun-filled deck w/ built-in sunsetter. Main lvl office/den is perfect for an in-home workspace/craft room, plus 2

    Erin Flesch MHB Real Estate

    3095 Rebel Dr, Sun Prairie, WI 53590
  • /44

    $500,000 Open Sun 12:30PM - 2PM

    • 3 Beds
    • 2.5 Baths
    • 2,456 Sq Ft

    326 N Heatherstone Dr, Sun Prairie, WI 53590

    Welcome home to your perfect retreat! This is the one you've been waiting for! From the moment you walk in, you’ll fall in love with the airy, updated spaces—gleaming new floors, freshly painted white trim, a stunning new kitchen with white cabinets, high end stainless appliances, quartz counters, and a cozy stone fireplace for quiet nights in. Step onto the new composite deck and soak in the

    Jo Ferraro EXP Realty, LLC

    326 N Heatherstone Dr, Sun Prairie, WI 53590
  • /43

    $775,000

    • 5 Beds
    • 3.5 Baths
    • 4,677 Sq Ft

    279 N Mallard Dr, Sun Prairie, WI 53590

    Extensively upgraded 5-bed, 3.5-bath home in desirable West Prairie Village, just steps from the park and walking distance to Royal Oaks Elementary & Prairie View Middle. Main level features a chef’s kitchen with quartz countertops, 9-ft island, SS appliances, 5 burner gas cooktop, wall oven, and walk-in pantry. Sun-filled dining area with vaulted ceiling, great room with gas fireplace,

    Paul Haviland Stark Company, REALTORS

    279 N Mallard Dr, Sun Prairie, WI 53590
  • /68

    $699,000

    • 4 Beds
    • 4 Baths
    • 3,921 Sq Ft

    1276 Fairhaven Rd, Sun Prairie, WI 53590

    Step inside to an inviting open floor plan featuring a spacious living room and a beautifully designed kitchen with a large island and elegant granite countertops. A versatile flex room and full bathroom on the main floor adds convenience, whether you need a home office or guest space. Bedrooms are arranged in a split layout w/ primary suite featuring: walk-in shower & soaking tub for ultimate

    Kevin Navarro EXP Realty, LLC

    1276 Fairhaven Rd, Sun Prairie, WI 53590
  • /4

    $85,000

    • Land
    • 0.17 Acre
    • $500,000 per Acre

    3240 Prospect Dr, Sun Prairie, WI 53590

    Discover the perfect opportunity to build your dream home on this exceptional lot in the charming Providence subdivision. Ideally positioned, this prime location offers easy access to shopping, top-rated schools, scenic walking trails, and a variety of local amenities. With the option to build to suit, you can partner with your builder to craft a home that reflects your unique vision. Embrace the

    Dick Quinn Stark Company, REALTORS

    3240 Prospect Dr, Sun Prairie, WI 53590
  • /32

    $399,900

    • 3 Beds
    • 2 Baths
    • 1,488 Sq Ft

    3298 Box Hill Rd, Sun Prairie, WI 53590

    Charming 3 bedroom ranch. Open concept layout with cathedral ceilings. Chef's kitchen equipped with SS appliances, granite top island, and pantry. Large primary suite with door to walk out patio & deck. Lower level has rec room, 3/4 bath and 3rd bedroom. Plenty of storage space. 2 car attached garage. Deck structurally renovated including new deck flooring in June 2025. New Washer and Dryer in

    Lou Elson EXIT Realty HGM

    3298 Box Hill Rd, Sun Prairie, WI 53590
  • /9

    $110,000

    • Land
    • 0.14 Acre
    • $785,714 per Acre

    218 S City Station Dr, Sun Prairie, WI 53590

    Sun Prairie lot close to Costco, Woodman's, UW East Hospital and many more essentials. Established neighborhood with curb, gutter and sidewalk in place. An ideal building location; don't miss out on this one!

    Gina Kloostra Cotter Realty LLC

    218 S City Station Dr, Sun Prairie, WI 53590
  • /35

    $325,000 Open Sun 11AM - 1PM

    • 2 Beds
    • 3.5 Baths
    • 2,000 Sq Ft

    573 Kelvington Dr Unit 1, Sun Prairie, WI 53590

    Welcome to this stunning end-unit condo on a spacious corner lot in West Sun Prairie, just off Hwy 19—ideal for an easy commute. This two-bedroom, three-and-a-half-bath home features vaulted ceilings, natural light, and a gas fireplace. The finished lower level includes a full bath and a window that brings in natural light—ideal for a guest suite, home office, additional living space, or flex

    Alan Mikkelson EXP Realty, LLC

    573 Kelvington Dr Unit 1, Sun Prairie, WI 53590
  • /5

    $110,000

    • Land
    • 0.13 Acre
    • $846,154 per Acre

    2693 Hazelnut Trail, Sun Prairie, WI 53590

    Sun Prairie lot close to Costco, Woodman's, UW East Hospital and many more essentials. Established neighborhood with curb, gutter and sidewalk in place. An ideal building location; don't miss out on this one!

    Gina Kloostra Cotter Realty LLC

    2693 Hazelnut Trail, Sun Prairie, WI 53590
  • /6

    $350,000

    • Land
    • 2.16 Acres
    • $162,037 per Acre

    2908-2936 Lucky Charms Cir, Sun Prairie, WI 53590

    Builders or Developers. Here is your chance to purchase 4 residential lots backing up to conservancy area on Sun Prairie's West side. Lots feature possible exposure and many views of wildlife. Most utilities are to lot except gas which is across the street. Lot sizes range from .42 to .72 acres. Parcels included 0810-111-0122-2, 0810-111-0111-2, 0810-111-0100-2, 0810-111-0089-2

    Scott Suchomel First Weber Inc

    2908-2936 Lucky Charms Cir, Sun Prairie, WI 53590
  • /49

    $649,900

    • 4 Beds
    • 3.5 Baths
    • 3,612 Sq Ft

    2893 Hazelnut Trail, Sun Prairie, WI 53590

    4 bed, 3.5 bath in the popular Fox Point neighborhood of Sun Prairie! This contemporary two-story home features a large open concept living room flooded with natural light from the south-facing windows. The kitchen has granite counters, stainless appliances, tile backsplash, island with breakfast bar & generous pantry. Off the living room are french doors to a den/office. Also on the main level,

    Caleb Payne Madcityhomes.Com

    2893 Hazelnut Trail, Sun Prairie, WI 53590
  • /2

    $84,900

    • Land
    • 0.20 Acre
    • $424,500 per Acre

    1116 Fairhaven Rd, Sun Prairie, WI 53590

    This prime lot is located in the Providence subdivision conveniently located near shopping, schools, walking trails and other amenities. Build to suit, bring your own builder. Create your dream home in this thriving community.

    Jeremiah Sullivan Real Broker LLC

    1116 Fairhaven Rd, Sun Prairie, WI 53590
  • /2

    $89,900

    • Land
    • 0.16 Acre
    • $561,875 per Acre

    3085 Triumph Dr, Sun Prairie, WI 53590

    This prime lot is located in the Providence subdivision conveniently located near shopping, schools, walking trails and other amenities. Build to suit, bring your own builder. Create your dream home in this thriving community.

    Jeremiah Sullivan Real Broker LLC

    3085 Triumph Dr, Sun Prairie, WI 53590
  • /2

    $89,900

    • Land
    • 0.16 Acre
    • $561,875 per Acre

    3149 Hope St, Sun Prairie, WI 53590

    This prime lot is located in the Providence subdivision conveniently located near shopping, schools, walking trails and other amenities. Build to suit, bring your own builder. Create your dream home in this thriving community.

    Jeremiah Sullivan Real Broker LLC

    3149 Hope St, Sun Prairie, WI 53590
  • /2

    $89,900

    • Land
    • 0.16 Acre
    • $561,875 per Acre

    3129 Hope St, Sun Prairie, WI 53590

    This prime lot is located in the Providence subdivision conveniently located near shopping, schools, walking trails and other amenities. Build to suit, bring your own builder. Create your dream home in this thriving community.

    Jeremiah Sullivan Real Broker LLC

    3129 Hope St, Sun Prairie, WI 53590
  • /21

    $349,000

    • Land
    • 1.11 Acres
    • $314,414 per Acre

    3012 Prospect Dr, Madison, WI 53777

    Professional and drone photos are coming soon! Prime opportunity in the heart of Sun Prairie! Ideally located near Prairie Lakes and American Parkway, offering unmatched accessibility and visibility. All permits have been pulled, and the lots are ready for digging—streamlining your development timeline. Designed for versatile multi-family units with commercial space on the lower level, the

    Ashley Jacobs Real Broker LLC

    3012 Prospect Dr, Madison, WI 53777
  • /25

    $325,000

    • Land
    • 0.47 Acre
    • $691,489 per Acre

    3011 Prospect Dr, Sun Prairie, WI 53590

    Professional and drone photos are coming soon! Prime opportunity in the heart of Sun Prairie! Ideally located near Prairie Lakes and American Parkway, offering unmatched accessibility and visibility. All permits have been pulled, and the lots are ready for digging—streamlining your development timeline. Designed for versatile multi-family units with commercial space on the lower level, the

    Ashley Jacobs Real Broker LLC

    3011 Prospect Dr, Sun Prairie, WI 53590
  • /3

    $1,227,870

    • Land
    • 0.94 Acre
    • $1,306,245 per Acre

    Lot 2 S Thompson Dr, Sun Prairie, WI 53590

    New plat map with outline of Lot 2. Great location for a drive-thru, located across from the new HyVee in Sun Prairie.

    Michael Herl Madison Commercial Real Estate LLC

    Lot 2 S Thompson Dr, Sun Prairie, WI 53590
  • /2

    $89,900

    • Land
    • 0.16 Acre
    • $561,875 per Acre

    3128 Prospect Dr, Sun Prairie, WI 53590

    This prime lot is located in the Providence subdivision conveniently located near shopping, schools, walking trails and other amenities. Build to suit, bring your own builder. Create your dream home in this thriving community.

    Jeremiah Sullivan Real Broker LLC

    3128 Prospect Dr, Sun Prairie, WI 53590
  • /2

    $84,900

    • Land
    • 0.16 Acre
    • $530,625 per Acre

    3148 Prospect Dr, Sun Prairie, WI 53590

    This prime lot is located in the Providence subdivision conveniently located near shopping, schools, walking trails and other amenities. Build to suit, bring your own builder. Create your dream home in this thriving community.

    Jeremiah Sullivan Real Broker LLC

    3148 Prospect Dr, Sun Prairie, WI 53590
  • /17

    $489,900 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,647 Sq Ft

    1125 Hickory Hills Dr, Sun Prairie, WI 53590

    Image is representative of home; colors may vary.All prices, promotions and specifications are subject to change at any time without notice based on the discretion of Veridian Homes.

    Builder Photo

    Veridian Homes

    Builder

    1125 Hickory Hills Dr, Sun Prairie, WI 53590

Showing Results 1 - 40, Page 1 of 2

Why Live in Westside

Westside is the epitome of modern growth, with single-family homes, apartments and townhouses filling empty fields and farms. Sun Prairie , a suburban city outside Madison , has a growing population. Westside is its largest and newest neighborhood, taking on ...

Frequently Asked Questions

Is Westside a good place to live?
Westside is a good place to live. Westside is considered somewhat walkable and bikeable. Westside is a cul de sac neighborhood. Westside has 1 park for recreational activities. It has a median age of 36. The average household income is $115,320 which is above the national average. College graduates make up 57.3% of residents. A majority of residents in Westside are renters, with 51.4% of residents renting and 48.6% of residents owning their home. A local real estate agent serving Westside can help you decide if this neighborhood is the right one for you. Learn more on our Westside neighborhood guide.
How much do you need to make to afford a house in Westside?
The median home price in Westside is $479,900. If you put a 20% down payment of $96,000 and had a 30-year fixed mortgage with an interest rate of 6.58%, your estimated principal and interest payment would be $2,450 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $105K a year to afford the median home price in Westside. The average household income in Westside is $115K.
What are the best public schools in Westside?
The best public schools that serve Westside are:
What are the best private schools in Westside?
The best private schools that serve Westside are:
What are the most popular zip codes in Westside, Sun Prairie, WI?
The most popular zip codes in Westside, Sun Prairie, WI include 53590, 53718, 53532, 53704 and 53575.
What are the most popular neighborhoods near Westside, Sun Prairie, WI?
The most popular neighborhoods near Westside, Sun Prairie, WI are Northeast Madison, South Central Sun Prairie, Westwynde, Central Sun Prairie and Old Village.

Home Trends in Westside, WI

Housing Trends

Median Sale Price
$455,000
Median Single Family Sale Price
$479,438
Median 2 Bedroom Sale Price
$300,000
Median 1 Bedroom Sale Price
$230,000
Average Price Per Sq Ft
$239
Number of Homes for Sale
46
Last 12 months Home Sales
145
Months of Supply
3.80
Median List Price
$479,900
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
1%
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