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Winston Homes for Sale

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  • /45

    $679,900

    • 4 Beds
    • 3.5 Baths
    • 3,072 Sq Ft

    635 Wil Way, Winston, OR 97496

    One of a kind property that is a true gem. Panoramic views of the Abacela Vineyards, the Wildlife Safari, the beautiful city, and the stunning valleys. While being tucked away at the end of the road for extra privacy. Nestled on over 20 acres, this parcel adjoins the Wildlife Safari. Imagine watching exotic animals from your back yard! The home is a gorgeous 2019 build featuing many high quality

    Agent Photo

    Ashton Faas

    Different Better Real Estate

    (458) 232-3589

    635 Wil Way, Winston, OR 97496
  • /27

    $357,900

    • 3 Beds
    • 2 Baths
    • 1,433 Sq Ft

    380 SE Sunnyside Dr, Winston, OR 97496

    Welcome to 380 Sunnyside! This move-in-ready 3-bedroom, 2-bath home offers comfort, quality updates, and everyday convenience. Vaulted ceilings and peaceful territorial views create a bright, open feel from the moment you step inside. Recent upgrades include fresh interior paint, brand-new LVP flooring, and a newly built spacious deck, giving the home a modern look without the new construction

    Agent Photo

    Rockwell Group

    eXp Realty, LLC

    (458) 224-8911

    380 SE Sunnyside Dr, Winston, OR 97496
  • /28

    $350,000

    • Land
    • 7.4 Acres
    • $47,297 per Acre

    0 Wil Way Unit 24094727, Winston, OR 97496

    Rare investment opportunity! This property features astounding views of Abacela Vineyards and the surrounding valleys. Property has already been approved to be partitioned as either 2 larger parcels or a 28 lot subdivision! Currently no HOA or CC&Rs! Utilities conveniently are available nearby ready to be connected. The 2 parcels are also listed separately. Make an offer today before one or all

    Agent Photo

    Ashton Faas

    Different Better Real Estate

    (458) 310-3411

    0 Wil Way Unit 24094727, Winston, OR 97496
  • /15

    $185,000

    • Land
    • 3.14 Acres
    • $58,917 per Acre

    0 Wil Way Unit 24278136, Winston, OR 97496

    Great investment opportunity! This property features astounding views of Abacela Vineyards and the surrounding valleys. Currently no HOA or CC&Rs! Property has already been approved to be partitioned as a larger parcel or a over a dozen lot subdivision! Utilities conveniently are available nearby ready to be connected. The other parcel is also listed separately. Or both properties are available

    Agent Photo

    Ashton Faas

    Different Better Real Estate

    (458) 224-5797

    0 Wil Way Unit 24278136, Winston, OR 97496
  • /15

    $185,000

    • Land
    • 4.26 Acres
    • $43,427 per Acre

    0 Wil Way Unit 24292479, Winston, OR 97496

    Unique investment opportunity! This property features astounding views of Abacela Vineyards and the surrounding valleys. Currently no HOA or CC&Rs! Property has already been approved to be partitioned as a larger parcel or a over a dozen lot subdivision! Utilities conveniently are available nearby ready to be connected. The other parcel is also listed separately. Or both properties are available

    Agent Photo

    Ashton Faas

    Different Better Real Estate

    (458) 217-1693

    0 Wil Way Unit 24292479, Winston, OR 97496
  • /47

    $499,900

    • 3 Beds
    • 2 Baths
    • 1,928 Sq Ft

    263 Wil Way, Winston, OR 97496

    Welcome to Your Like-New Custom Home in Winston, Oregon!Step inside this beautifully crafted home by Shelby & Miguelena Construction, where quality craftsmanship and thoughtful design are evident in every detail. The open-concept floor plan features soaring vaulted ceilings, beautiful flooring, and a warm, inviting layout that flows effortlessly for both everyday living and entertaining.At the

    Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

    263 Wil Way, Winston, OR 97496
  • /23

    $55,000

    • 1 Bed
    • 1 Bath
    • 384 Sq Ft

    119 Oak Leaf Ln, Winston, OR 97496

    Affordable living in a quiet 55+ community! This cozy 1-bedroom, 1-bath manufactured home offers a functional layout and easy, low-maintenance living. The kitchen comes equipped with a free-standing range and refrigerator, both included in the sale. Located in a peaceful, well-kept neighborhood with a friendly community atmosphere. Conveniently situated near local amenities while maintaining a

    Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

    119 Oak Leaf Ln, Winston, OR 97496
  • /45

    $66,000

    • 2 Beds
    • 2 Baths
    • 1,152 Sq Ft

    125 SE Estate Loop, Winston, OR 97496

    Take in breathtaking views of Umpqua Valley and the surrounding mountains from this spacious manufactured home located in a welcoming 55+ community. Unwind on the large covered front porch. Featuring a metal roof, double-pane vinyl windows, and a sturdy concrete block foundation, this home offers lasting durability. Stay comfortable year-round with the newer heat pump installed in 2022.

    Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

    125 SE Estate Loop, Winston, OR 97496
  • /48

    $265,000

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

    771 SE Hall St, Winston, OR 97496

    Welcome to 771 SE Hall St in Winston where comfort meets convenience in this spacious 3 bedroom 2 bath home featuring 1650 square feet of well designed living space on a 0.16 acre lot. Curb appeal abounds with a freshly painted covered front porch and an expansive driveway providing tons of parking for vehicles or recreational toys. Peace of mind comes included with a newer roof and a newer hot

    Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

    771 SE Hall St, Winston, OR 97496
  • /36

    $409,000

    • 7 Beds
    • 4.5 Baths
    • 3,861 Sq Ft

    2414 Brockway Rd, Winston, OR 97496

    Opportunity awaits! Whether you’re a savvy investor seeking passive income, a large family looking for a multi-generational setup, or a single household wanting a home with the luxury of renting out additional units, this three-home property offers countless possibilities.Located on historic Brockway Road, the property spans .58 acres and is lined with mature trees and lush landscaping, creating

    Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

    2414 Brockway Rd, Winston, OR 97496
  • /41

    $499,900 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,089 Sq Ft

    160 Wil Way, Winston, OR 97496

    OPEN HOUSE! Sunday 3/29 1-3pm New Home by JW Construction Inc.This beautiful one-level home offers just over 2,000 square feet with three bedrooms and two and a half bathrooms. The open great room features vaulted ceilings, luxury vinyl plank flooring, recessed lighting, and a gas fireplace. A large sliding door opens to an expansive deck, perfect for entertaining or relaxing. The kitchen is

    Tyler Head Turning Point Realty Group

    160 Wil Way, Winston, OR 97496
  • /32

    $555,000 Open Sun 1PM - 3PM

    • 4 Beds
    • 3 Baths
    • 2,660 Sq Ft

    102 Sarah Bear Ln, Winston, OR 97496

    Meticulous quality 4 br 3 bath 2660 sq ft home, with real wood floors, 2 gas fireplaces, central vac, top quality custom elegant crown molding. Formal dining, gourmet kitchen, over sized gazebo/pergola, colored stamped concrete, sprinkler system, fenced manicured private backyard with raised beds. Has new astro turf for low maintenance, covered patio. The gourmet kitchen has granite, pantry, new

    Valynn Currie Currieco Real Estate

    102 Sarah Bear Ln, Winston, OR 97496
  • /40

    $499,900 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,999 Sq Ft

    150 Wil Way, Winston, OR 97496

    OPEN HOUSE! Sunday 1-3pm 3/29 New Home by JW Construction Inc.This beautifully crafted 2,143 sq ft home offers 3 bedrooms and 2 1/2 bathrooms with a thoughtful layout and excellent separation of space. Set on a low-maintenance lot with views of trees and the surrounding mountains, 140 Wil Way combines modern design with comfort and convenience.The open-concept main level features high ceilings,

    Tyler Head Turning Point Realty Group

    150 Wil Way, Winston, OR 97496
  • /42

    $599,000

    • 3 Beds
    • 2 Baths
    • 2,431 Sq Ft

    605 Deerwood Ct, Winston, OR 97496

    This custom-built Passive Solar home, constructed in 1979, offers a rare blend of timeless beauty, retro charm, and thoughtful modern updates. This Passive Solar home is thoughtfully designed to work with the sun and climate, providing comfort, efficiency, and sustainability without relying heavily on mechanical systems. Ideally located near local river recreation and just a short drive to the

    Lisa Ollivant RE/MAX Integrity

    605 Deerwood Ct, Winston, OR 97496
  • /2

    $95,000

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft

    130 Stephanie Ct, Winston, OR 97496

    Well-maintained 3-bedroom, 2-bath double-wide manufactured home located in the desirable Rosewood Park Place community in Winston. Offering 1,344 sq ft of comfortable single-level living, this home features a functional floor plan with a spacious living area, a well-equipped kitchen complete with pantry, built-in microwave, dishwasher, and all appliances included. The interior offers a blend of

    Jason Mann J Mann Realty

    130 Stephanie Ct, Winston, OR 97496
  • /20

    $230,000

    • 2 Beds
    • 1 Bath
    • 1,323 Sq Ft

    381 SE Gregory Dr, Winston, OR 97496

    Seize this opportunity with this charming single-story 1948 ranch style home boasting 2 bedrooms, 1 bath, and about 1,323 sq ft of living space on a generous 0.61-acre lot. Surrounded by mature trees and offering a peaceful, rural-suburban feel in the heart of Douglas County. This mid-century gem features timeless details like a prominent brick chimney, large picture windows for natural light,

    Nile Stark RE/MAX Integrity

    381 SE Gregory Dr, Winston, OR 97496
  • /44

    $699,500

    • 4 Beds
    • 2 Baths
    • 2,240 Sq Ft

    411 Woodland Dr, Roseburg, OR 97471

    Discover a lifestyle rooted in fresh air, room to roam, and time spent outside. This two-story ranch sits above sweeping views of Abacela Vineyard and offers Lookingglass Creek frontage with irrigation rights, K-line system, and pump already in place. Enjoy your own private swimming hole, raised-bed fenced garden, and greenhouse—perfect for growing, tinkering, and staying active year-round.The

    Nataly Mattox RE/MAX Integrity

    411 Woodland Dr, Roseburg, OR 97471
  • /15

    $229,000

    • 2 Beds
    • 2 Baths
    • 924 Sq Ft

    90 SE Darrell Ave, Winston, OR 97496

    This charming 2-bedroom, 2-bathroom manufactured home in Winston, Oregon offers comfortable, modern living in a convenient location close to shopping, dining and other local amenities. Nestled on its own land, this home combines privacy with easy access to town.Inside, you’ll love the open-design floor plan that creates a bright, spacious feel throughout the living room, dining area and

    Rebekah Sexauer eXp Realty, LLC

    90 SE Darrell Ave, Winston, OR 97496
  • /20

    $60,000

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

    271 SE Robinson St, Winston, OR 97496

    Build Your Dream Home on This Prime Lot!Nice Lot – Prime Location – All Utilities – Investment Opportunity!Discover the perfect canvas for your future home. This spacious lot comes with full utilities—water, electricity, and sewer—ready for you to build. Nestled in a good location, it’s ideal for families, investors, or anyone looking to live in town. Don’t miss out on this incredible

    Kayla Wehe Lamonte Real Estate Professionals

    271 SE Robinson St, Winston, OR 97496
  • /11

    $312,000

    • Land
    • 13.5 Acres
    • $23,111 per Acre

    0 NW Brockway Rd, Winston, OR 97496

    Premier 13.5 Mixed-Use Development Opportunity! A trifecta of buildability and prestige. Position your next project in the path of progress with this exceptional parcel. Located strategically within the Urban Growth Area and zoned as mixed use (CHIS), this site offers density potential combined with the unparalleled natural beauty of the region which include mountain and vineyard views. The

    Cynthia Beach The Neil Company Real Estate

    0 NW Brockway Rd, Winston, OR 97496
  • /15

    $149,900

    • 2 Beds
    • 2 Baths
    • 1,130 Sq Ft

    463 SE Gregory Dr, Winston, OR 97496

    1993 manufactured home with addition. Has 1130 sq ft with deck. On .21 acre lot. 3 br 2 baths. Includes range, refrig, microwave, dishwasher, trash compactor, washer/dryer. Assumable VA loan. Has playhouse and storage building.

    Valynn Currie Currieco Real Estate

    463 SE Gregory Dr, Winston, OR 97496
  • /15

    $180,000

    • 2 Beds
    • 1 Bath
    • 784 Sq Ft

    101 NE Darrell Ave, Winston, OR 97496

    Charming affordable singlewide manufacture home on .18 of an acre, located on a corner lot. This 2 bedroom, 1 bath home has a covered front porch and back deck with a chain link fenced yard. Storage shed and off street parking.

    Nancy Wood Oregon Life Homes

    101 NE Darrell Ave, Winston, OR 97496
  • /21

    $195,000

    • 2 Beds
    • 2 Baths
    • 1,120 Sq Ft

    751 SE Meadowood Dr, Winston, OR 97496

    1995 Double-wide manufactured home on a good sized lot in Winston. Not perfect but a lot of home for the money. Central heat and air conditioning, carport and lots of room for a garden. A great home for the money. Affordable living, close to park and community center. Roof has just been replaced.

    Timothy A Smith RE/MAX Integrity

    751 SE Meadowood Dr, Winston, OR 97496
  • /22

    $375,000 Open Sat 1PM - 3PM

    • 3 Beds
    • 2 Baths
    • 1,452 Sq Ft

    182 Woodduck St, Winston, OR 97496

    Quality contemporary 3 bedroom, 2 bath 1452 sq ft home built in 2005 in Hunters Crossing. Has Double garage, vaulted ceilings, appliances included. Newly painted. Laminate floors throughout, covered patio in private fenced yard low maintenance. Will finance all ways. Turn key ready. RV Parking/boat parking.

    Valynn Currie Currieco Real Estate

    182 Woodduck St, Winston, OR 97496
  • /34

    $359,000 Open Sat 12PM - 2PM

    • 4 Beds
    • 2 Baths
    • 1,710 Sq Ft

    380 NW Cary St, Winston, OR 97496

    Open house April 11th from 12 - 2pm.Schedule your private tour today of this adorable 4bd 2ba open floor plan home, located on a generous lot, with an extra deep garage and additional off-street parking for your RV or Boat. Just a 15-minute drive to Roseburg, close to local schools and just down the street from the Wildlife Safari.

    Willow Pearson Oregon Life Homes

    380 NW Cary St, Winston, OR 97496
  • /11

    $199,900

    • 3 Beds
    • 2 Baths
    • 1,188 Sq Ft

    1580 Winston Section Rd, Winston, OR 97496

    This 3-bedroom, 2-bathroom "fixer upper" sits on a peaceful 0.18-acre corner lot, offering a quiet atmosphere and beautiful mountain views right from your doorstep. While the home is ready for interior renovation, the floor plan features three bedrooms, two bathrooms, laundry room, large kitchen, creating a cozy feeling once restored. A standout is the 576 sqft detached garage/shop, where half

    Cynthia Beach The Neil Company Real Estate

    1580 Winston Section Rd, Winston, OR 97496
  • /23

    $90,000

    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft

    124 Country Side Ln, Winston, OR 97496

    Welcome home to this charming home located in a beautifully maintained 55+ community! With 3 bedrooms, 2 baths, and 1,296 sq. ft. of inviting living space, this home features vaulted ceilings, a bright open layout, and a manicured corner lot. The walk-through kitchen includes a breakfast bar, built-in microwave, stove, refrigerator, and a brand-new dishwasher. The spacious primary suite offers

    Jason Mann J Mann Realty

    124 Country Side Ln, Winston, OR 97496
  • /16

    $850,000

    • Land
    • 37.86 Acres
    • $22,451 per Acre

    0 Danielle Dr Unit 122251646, Winston, OR 97496

    Prime development opportunity in Winston, Oregon! This expansive 38-acre property has potential for 90 buildable residential lots, perfect for a new housing community. Situated in a peaceful location with easy access to local amenities, this land offers a great investment potential for developers. Ideal for those looking to create a vibrant neighborhood in a growing area. Don’t miss out on this

    Jeremy Parmenter TLC Realty

    0 Danielle Dr Unit 122251646, Winston, OR 97496
  • /4

    $2,000,000

    • 4 Beds
    • 2 Baths
    • 1,992 Sq Ft

    80 NW Lost Ln, Winston, OR 97496

    Great Property for future Developing. 2007 Manufactured Home on .68 of a Ac. City Water and Sewer.

    Dawn Trapalis Harcourts Integrity Team Real Estate Services, LLC.

    80 NW Lost Ln, Winston, OR 97496
  • /21

    $127,000

    • 3 Beds
    • 2 Baths
    • 1,404 Sq Ft

    180 Twin Oaks Loop, Winston, OR 97496

    application and park requirements, No other fees to HOA except basic space rent 604$+121$ w/s/g Property Listing: 180 Twin Oaks Loop, Winston, OR Renovated 3-Bedroom,2-Bathroom Double Wide in 55+ Community Welcome to this beautifully renovated 3-bedroom, 2-bathroom home located in the sought-after Twin Oaks Mobile Park Estates, a quiet and well-maintained 55+ community in Winston, OR. This

    Raymond Coburn eXp Realty, LLC

    180 Twin Oaks Loop, Winston, OR 97496
  • /10

    $249,500

    • Land
    • 0.45 Acre
    • $554,444 per Acre

    0 SW Main St, Winston, OR 97496

    Looking for a retail, office or hospitality location in Winston? This lot is strategically located near the intersection of Hwy 42 & Hwy 99 with easy access to I-5 and on the route to Oregon's coastal destinations! This lot is the best that Winston has to offer...

    Jody Tatone RE/MAX Integrity

    0 SW Main St, Winston, OR 97496
  • /29

    $412,500

    • 3 Beds
    • 2.5 Baths
    • 1,874 Sq Ft

    241 SE Johnson St, Winston, OR 97496

    Almost-new two-story home offering 3 bedrooms, 2.1 baths, and 1,874 sq. ft. of comfortable living space, gently occupied for just two years. Enjoy both front and back porches—ideal for relaxing or entertaining. The kitchen features soft-close cabinets and a gas range, while the extra-large laundry/utility room adds everyday convenience. Additional features include ductless heating and A/C, a gas

    Mandy Parker Oregon Life Homes

    241 SE Johnson St, Winston, OR 97496
  • /8

    $2,125,000

    • Land
    • 15.05 Acres
    • $141,196 per Acre

    215 Parkinson Rd, Winston, OR 97496

    Lovely acreage on South Umpqua River. Zoned agriculture. Water rights from 1953. 44x60 barn has been partially renovated. Running water at barn. Use your imagination on the uses for this wonderful acreage on the river. Buyer to do all due diligence regarding every aspect of the property. Seller makes no disclosures.

    Nick Knight Knight Realty Group LLC

    215 Parkinson Rd, Winston, OR 97496
  • /19

    $77,500

    • 3 Beds
    • 2 Baths
    • 1,188 Sq Ft

    235 Twin Oaks Loop, Winston, OR 97496

    Cozy residence that's located in the 55+ Winston Twin Oaks Mobile Estates community! This manufactured double-wide home offers three bedrooms and 2 baths, with features including a spacious primary bedroom and bath, large living room, dining area, kitchen with appliances, laundry room, and a carport with shed. Space rent includes water, sewer, and garbage, for $725 a month (there is an

    Kimberly Krebs Stellar Realty Northwest

    235 Twin Oaks Loop, Winston, OR 97496
  • /39

    $160,000

    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft

    157 NW Bree Dr, Winston, OR 97496

    Pride of ownership shows in this 3 bedroom, 2 bath manufactured home in an all-ages park with low space rent. This one is truly move-in ready with a lot of the big stuff already done—newer roof, water heater, appliances, and even a shed for extra storage. The layout just makes sense with good living space, tons of natural light, and a separate office that works great for working from home or

    Anthony Beckham Different Better Real Estate

    157 NW Bree Dr, Winston, OR 97496
  • /27

    $357,900

    • 3 Beds
    • 2 Baths
    • 1,433 Sq Ft

    380 Sunnyside Dr, Winston, OR 97496

    Welcome to 380 Sunnyside! This move-in-ready 3-bedroom, 2-bath home offers comfort, quality updates, and everyday convenience. Vaulted ceilings and peaceful territorial views create a bright, open feel from the moment you step inside.Recent upgrades include fresh interior paint, brand-new LVP flooring, and a newly built spacious deck, giving the home a modern look without the new construction

    Chase Lee eXp Realty, LLC

    380 Sunnyside Dr, Winston, OR 97496
  • /8

    $590,000

    • Land
    • 4.77 Acres
    • $123,690 per Acre

    350 View Point Terrace, Winston, OR 97496

    Excellent investment opportunity! 31 platted lots prime for development in the growth seeking city of Winston! This early 1980's subdivision is prominently located next to a newer construction community to strengthen the potential development value. Pacific Power just confirmed power is available! Call Winston city manager with all your building/development questions as he will accommodate all

    Michael Fischer Oregon Life Homes

    350 View Point Terrace, Winston, OR 97496
  • /47

    $342,500

    • 3 Beds
    • 1 Bath
    • 1,434 Sq Ft

    10 SE Kegler Ave, Winston, OR 97496

    Set on a full acre at the edge of town, this property blends flexibility, functionality, and a 1,200 sq ft shop that’s hard to ignore! The 3-bedroom, 1-bath home includes an oversized living room with exposed wood accents and rustic-style posts that bring a bit of texture and charm. Heating and cooling are handled with ductless systems, and there’s a gas fireplace to keep things cozy. The kitchen

    Anthony Beckham Different Better Real Estate

    10 SE Kegler Ave, Winston, OR 97496
  • /4

    $210,000

    • Land
    • 0.71 Acre
    • $295,775 per Acre

    0 SE Gregory Dr, Winston, OR 97496

    Ready to go multifamily with construction plans. See attached plans for 3 triplex buildings. Utilities are to property line. Water & sewer available. Great opportunity for a hard to find multifamily property. CLA for more information

    Larry KW Alberts Keller Williams Realty Eugene and Springfield

    0 SE Gregory Dr, Winston, OR 97496

Frequently Asked Questions Why Live in Winston

Is Winston a good place to live?
Winston is a good place to live. Winston is considered car-dependent and somewhat bikeable with some transit options. Winston is a neighborhood with a crime score of 2, making it safer than the average neighborhood in the U.S. Winston has 1 park for recreational activities. It has a median age of 43. The average household income is $66,222 which is below the national average. College graduates make up 13.7% of residents. A majority of residents in Winston are home owners, with 31.2% of residents renting and 68.8% of residents owning their home. A local real estate agent serving Winston can help you decide if this neighborhood is the right one for you. Learn more on our Winston neighborhood guide.
Is Winston, OR a safe neighborhood?
Winston, OR is safer than the average neighborhood in the United States. It received a crime score of 2 out of 10.
How much do you need to make to afford a house in Winston?
The median home price in Winston is $372,000. If you put a 20% down payment of $74,400 and had a 30-year fixed mortgage with an interest rate of 6.46%, your estimated principal and interest payment would be $1,870 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $80K a year to afford the median home price in Winston. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Winston is $66K.
What are the best public schools in Winston?
The best public schools that serve Winston are:
What are the most popular zip codes in Winston, Winston, OR?
The most popular zip codes in Winston, Winston, OR include 97496, 97471, 97457, 97470 and 97416.
What are the most popular neighborhoods near Winston, Winston, OR?
The most popular neighborhoods near Winston, Winston, OR are Green, West Harvard, Hucrest, Melrose and Roseburg North.

Home Trends in Winston, OR

Housing Trends

Median Sale Price
$325,000
Median Single Family Sale Price
$355,000
Average Price Per Sq Ft
$230
Number of Homes for Sale
16
Last 12 months Home Sales
63
Months of Supply
3.00
Median List Price
$372,000
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
-6%
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