4,367

Woodstock, CT Homes

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  • 429 New Sweden Rd, Woodstock, CT 06281
    429 New Sweden Rd, Woodstock, CT 06281
    429 New Sweden Rd, Woodstock, CT 06281
    /38

    $625,000

    $21K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,478 Sq Ft

    429 New Sweden Rd, Woodstock, CT 06281

    Step back in time and discover the charm of this beautifully preserved 2,400 sq. ft. farmhouse, originally built in 1805. (Renovated in 1980) Rich in character and timeless appeal, this property offers the perfect blend of country living and modern convenience. Whether you dream of cultivating extensive gardens, raising animals, creating a self-sustaining homestead, or simply enjoying wide-open

    Agent Photo

    Elizabeth Scranton

    Kazantzis Real Estate, LLC

    429 New Sweden Rd, Woodstock, CT 06281
  • 29 Braaten Hill Rd, Woodstock, CT 06281

    $699,000

    Sold Jul 31, 2026

    29 Braaten Hill Rd, Woodstock, CT 06281

    • 3 Beds
    • 3 Baths
    • 2,702 Sq Ft
    • Built 1979

    Last Sold Summary

    • $259/SF
    • 34 Days On Market

    Current Estimated Value $714,673

    Last Listing Agent Stephen Daly KW Legacy Partners

    29 Braaten Hill Rd, Woodstock, CT 06281
    • 18 Jeans Ct, Woodstock, CT 06281

      Est $699,610

      Not Listed For Sale

      18 Jeans Ct, Woodstock, CT 06281

      • 4 Beds
      • 2.5 Baths
      • 2,880 Sq Ft
      • Built 2006
      18 Jeans Ct, Woodstock, CT 06281

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Lynn Converse RE/MAX Bell Park Realty

  • 36 Olde Meadow Rd, Woodstock, CT 06281
    36 Olde Meadow Rd, Woodstock, CT 06281
    36 Olde Meadow Rd, Woodstock, CT 06281
    /11

    $79,700

    • Land
    • 1.92 Acres
    • $41,510 per Acre

    36 Olde Meadow Rd, Woodstock, CT 06281

    Rare opportunity to secure the last premium homesite in one of Woodstock's most desirable areas, Eastwood Estates. This approved building lot is being offered as part of a custom home package with a local established builder. It is not being offered for sale as "land only" and requires a build contract with the designated builder, PMR Home Design and Expansion. Buyers may choose from thoughtfully

    Agent Photo

    Tina Lajoie

    Signature Properties of N.E.

    36 Olde Meadow Rd, Woodstock, CT 06281
  • 140 Tripp Rd, Woodstock, CT 06281

    $360,000

    Sold Jun 26, 2026

    140 Tripp Rd, Woodstock, CT 06281

    • 2 Beds
    • 1 Bath
    • 1,274 Sq Ft
    • Built 1840

    Last Sold Summary

    • 4% Below List Price
    • $283/SF
    • 3 Days On Market

    Current Estimated Value $368,644

    Last Listing Agent Heather Sawyer William Pitt Sotheby's Int'l

    140 Tripp Rd, Woodstock, CT 06281
    • 123 Laurel Hill Dr, Woodstock Valley, CT 06282

      Est $682,967

      Not Listed For Sale

      123 Laurel Hill Dr, Woodstock Valley, CT 06282

      • 3 Beds
      • 2 Baths
      • 1,944 Sq Ft
      • Built 1958
      123 Laurel Hill Dr, Woodstock Valley, CT 06282

      Last Sold Summary

      • 30 Days On Market

      Last Listing Agent Chris Farrell Carbutti & Co., Realtors

  • 57 Beaver Dam Rd, Woodstock Valley, CT 06282
    57 Beaver Dam Rd, Woodstock Valley, CT 06282
    57 Beaver Dam Rd, Woodstock Valley, CT 06282
    /25

    $355,000

    $24K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 888 Sq Ft

    57 Beaver Dam Rd, Woodstock Valley, CT 06282

    Adorable year-round home on Lake Bunggee, ideally located across from a private beach with stunning lake views. The main level features vaulted ceilings and an open-concept layout connecting the living room, dining area, and kitchen. There are two bedrooms on the main floor, along with a finished room on the lower level for added space. Enjoy not only the beautiful lake views but also a private

    Agent Photo

    Carol Ryniewicz

    CR Premier Properties

    57 Beaver Dam Rd, Woodstock Valley, CT 06282
  • 234 Pole Bridge Rd, Woodstock, CT 06281

    $715,000

    Sold Aug 11, 2026

    234 Pole Bridge Rd, Woodstock, CT 06281

    • 4 Beds
    • 2 Baths
    • 2,016 Sq Ft
    • Built 2010

    Last Sold Summary

    • 5% Below List Price
    • $355/SF
    • 54 Days On Market

    Current Estimated Value $736,768

    Last Listing Agent Matthew Huberdault Byrnes Real Estate Company

    234 Pole Bridge Rd, Woodstock, CT 06281
    • 342 County Rd, Woodstock, CT 06281

      Est $432,806

      Not Listed For Sale

      342 County Rd, Woodstock, CT 06281

      • 3 Beds
      • 2 Baths
      • 1,170 Sq Ft
      • Built 1963
      342 County Rd, Woodstock, CT 06281

      Last Sold Summary

      • 28 Days On Market

      Last Listing Agent Kimberly Frasier Real Broker CT, LLC

  • 69 Meadowside Rd, Woodstock, CT 06281
    69 Meadowside Rd, Woodstock, CT 06281
    69 Meadowside Rd, Woodstock, CT 06281
    /17

    $69,500

    $16K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 592 Sq Ft

    69 Meadowside Rd, Woodstock, CT 06281

    Your seasonal escape is waiting at Meadowside of Woodstock - a private, gated 100-site co-op campground in Connecticut's Quiet Corner. Lot 69 features TWO structures: a 1999 40-foot Retreat park model with central air, new refrigerator, new deck, and new grill, PLUS a 12x16 log cabin on a concrete slab with electric fireplace and AC. Sleeps 6 total. Fully furnished including brand new sofa.

    Agent Photo

    Robbie Greene Santos

    RE/MAX One

    69 Meadowside Rd, Woodstock, CT 06281
  • 50 Old Sawmill Rd, Woodstock, CT 06281

    $400,000

    Sold Jun 24, 2026

    50 Old Sawmill Rd, Woodstock, CT 06281

    • 3 Beds
    • 2.5 Baths
    • 1,632 Sq Ft
    • Built 1968

    Last Sold Summary

    • 1% Above List Price
    • $245/SF
    • 26 Days On Market

    Current Estimated Value $399,793

    Last Listing Agent Darius Baturo Berkshire Hathaway NE Prop.

    50 Old Sawmill Rd, Woodstock, CT 06281
    • 853 Pole Bridge Rd, Woodstock, CT 06281

      Est $428,064

      Not Listed For Sale

      853 Pole Bridge Rd, Woodstock, CT 06281

      • 3 Beds
      • 1.5 Baths
      • 1,803 Sq Ft
      • Built 1982
      853 Pole Bridge Rd, Woodstock, CT 06281

      Last Sold Summary

      • 19 Days On Market

      Last Listing Agent Mary Collins Berkshire Hathaway NE Prop.

  • 00 Ide Perrin Rd, Woodstock, CT 06281
    00 Ide Perrin Rd, Woodstock, CT 06281
    00 Ide Perrin Rd, Woodstock, CT 06281
    /22

    $299,900

    • Land
    • 79 Acres
    • $3,796 per Acre

    00 Ide Perrin Rd, Woodstock, CT 06281

    On a private road surrounded by unspoiled natural beauty, this remarkable 79-acre property offers exceptional privacy and endless potential. Two brooks enhance the landscape - Lebanon Brook along the western boundary and Porter Pond Brook to the east. The land features a mix of wetlands and highlands, heavily wooded with abundant timber resources. Create your secluded homestead in the wilderness

    Agent Photo

    Catherine Howard

    Berkshire Hathaway NE Prop.

    00 Ide Perrin Rd, Woodstock, CT 06281
  • 37 Pulpit Rock Rd, Woodstock, CT 06281

    $625,000

    Sold Sep 22, 2025

    37 Pulpit Rock Rd, Woodstock, CT 06281

    • 4 Beds
    • 2.5 Baths
    • 2,682 Sq Ft
    • Built 1968

    Last Sold Summary

    • 7% Below List Price
    • $233/SF
    • 129 Days On Market

    Last Listing Agent Carol Ryniewicz CR Premier Properties

    37 Pulpit Rock Rd, Woodstock, CT 06281
    • XO Pole Bridge Rd, Woodstock, CT 06281
      XO Pole Bridge Rd, Woodstock, CT 06281
      XO Pole Bridge Rd, Woodstock, CT 06281
      /42

      Not Listed For Sale

      XO Pole Bridge Rd, Woodstock, CT 06281

      XO Pole Bridge Rd, Woodstock, CT 06281

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Dennis Duga Dr. LAND

  • 259 Quarry Rd, Woodstock, CT 06281
    259 Quarry Rd, Woodstock, CT 06281
    259 Quarry Rd, Woodstock, CT 06281
    /24

    $595,000

    • Land
    • 100 Acres
    • $5,950 per Acre

    259 Quarry Rd, Woodstock, CT 06281

    Discover the possibilities on this exceptional 100-acre parcel on Quarry Road in scenic Woodstock, Connecticut. Boasting approximately 1,900 feet of road frontage, this expansive property offers a rare combination of privacy, natural beauty, and development potential. The current owner has already cleared three beautiful potential building sites, each positioned to take advantage of the

    Agent Photo

    Carol Ryniewicz

    CR Premier Properties

    259 Quarry Rd, Woodstock, CT 06281
  • 36 Dunleavy Dr, Woodstock, CT 06281

    $524,000

    Sold Oct 20, 2025

    36 Dunleavy Dr, Woodstock, CT 06281

    • 3 Beds
    • 2 Baths
    • 2,036 Sq Ft
    • Built 1960

    Last Sold Summary

    • 5% Below List Price
    • $257/SF
    • 62 Days On Market

    Current Estimated Value $544,389

    Last Listing Agent Diane White Berkshire Hathaway NE Prop.

    36 Dunleavy Dr, Woodstock, CT 06281
    • 51 Tayler Trail, Woodstock Valley, CT 06282

      Est $460,515

      Not Listed For Sale

      51 Tayler Trail, Woodstock Valley, CT 06282

      • 3 Beds
      • 2.5 Baths
      • 1,950 Sq Ft
      • Built 2016
      51 Tayler Trail, Woodstock Valley, CT 06282

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Nathan Daniel Boston MetroWest, LLC

  • 36 Olde Meadow Rd, Woodstock, CT 06281
    36 Olde Meadow Rd, Woodstock, CT 06281
    36 Olde Meadow Rd, Woodstock, CT 06281
    /13

    $799,900

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,900 Sq Ft

    36 Olde Meadow Rd, Woodstock, CT 06281

    TO BE CONSTRUCTED | Starting at $799,900 Welcome to Eastwood Estates, where luxury living meets the natural beauty and tranquility of Woodstock. Set on a picturesque 1.92-acre homesite bordering protected open space and framed by classic New England stone walls, this offering provides a rare opportunity to BUILD a custom home in one of the area's most desirable neighborhoods. Partner with an

    Agent Photo

    Tina Lajoie

    Signature Properties of New England

    36 Olde Meadow Rd, Woodstock, CT 06281
  • 250 Child Rd, Woodstock, CT 06281

    $413,000

    Sold Mar 09, 2026

    250 Child Rd, Woodstock, CT 06281

    • 3 Beds
    • 2 Baths
    • 2,326 Sq Ft
    • Built 1981

    Last Sold Summary

    • 18% Above List Price
    • $178/SF
    • 2 Days On Market

    Current Estimated Value $434,528

    Last Listing Agent Joseph Murphy CR Premier Properties

    250 Child Rd, Woodstock, CT 06281
    • 41 Crooked Trail, Wood Stock, CT 06281

      Est $494,948

      Not Listed For Sale

      41 Crooked Trail, Wood Stock, CT 06281

      • 4 Beds
      • 2 Baths
      • 1,834 Sq Ft
      • Built 1972
      41 Crooked Trail, Wood Stock, CT 06281

      Last Sold Summary

      • 41 Days On Market

      Last Listing Agent Sandie Terenzi KW Legacy Partners

  • 0 Child Dome Rd Unit 24183833, Woodstock, CT 06281
    0 Child Dome Rd Unit 24183833, Woodstock, CT 06281
    /2

    $179,000

    • Land
    • 3.29 Acres
    • $54,407 per Acre

    0 Child Dome Rd Unit 24183833, Woodstock, CT 06281

    Rare opportunity to own a large tract of land in Woodstock, CT. This stunning location is one of the highest points in Woodstock. Surrounded by conservatory farmland, the views are for miles. The ride to this property, through the sparsely populated countryside, will surely give you the feel of the natural surroundings. Although located "far from the crowd" you are centrally located to Hartford,

    Bob Seele Coldwell Banker Realty

    0 Child Dome Rd Unit 24183833, Woodstock, CT 06281
  • 53 Prospect St, Woodstock, CT 06281

    $450,000

    Sold Jun 24, 2026

    53 Prospect St, Woodstock, CT 06281

    • 3 Beds
    • 2.5 Baths
    • 1,736 Sq Ft
    • Built 1956

    Last Sold Summary

    • 6% Above List Price
    • $259/SF
    • 14 Days On Market

    Current Estimated Value $424,809

    Last Listing Agent Skyla Gagnon RE/MAX Bell Park Realty

    53 Prospect St, Woodstock, CT 06281
    • 00 Child Rd, Woodstock, CT 06281

      Not Listed For Sale

      00 Child Rd, Woodstock, CT 06281

      00 Child Rd, Woodstock, CT 06281

      Last Sold Summary

      • 56 Days On Market

      Last Listing Agent Gary Pruitt Century 21 Classic Homes

  • 70 Hawkins Rd, Woodstock Valley, CT 06282
    70 Hawkins Rd, Woodstock Valley, CT 06282
    70 Hawkins Rd, Woodstock Valley, CT 06282
    /38

    $349,999

    $25K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 864 Sq Ft

    70 Hawkins Rd, Woodstock Valley, CT 06282

    Welcome to this charming 2-bedroom, 1.5-bath home that offers the perfect blend of comfort and convenience. Ideal for empty nesters, downsizers, or anyone looking for a fantastic condo alternative, this home provides the privacy of single-family living without the hassle HOA. Step inside and enjoy a warm and inviting layout with comfortable living spaces that make the home feel instantly

    Joyce Teixeira Dream Living Realty, LLC

    70 Hawkins Rd, Woodstock Valley, CT 06282
  • 40 Old Sawmill Rd, Woodstock, CT 06281

    $340,000

    Sold Jul 25, 2026

    40 Old Sawmill Rd, Woodstock, CT 06281

    • 3 Beds
    • 1.5 Baths
    • 960 Sq Ft
    • Built 1988

    Last Sold Summary

    • 3% Below List Price
    • $354/SF
    • 44 Days On Market

    Current Estimated Value $346,943

    Last Listing Agent John Downs Berkshire Hathaway NE Prop.

    40 Old Sawmill Rd, Woodstock, CT 06281
    • 429 Child Rd, Woodstock, CT 06281

      Est $745,135

      Not Listed For Sale

      429 Child Rd, Woodstock, CT 06281

      • 3 Beds
      • 4 Baths
      • 3,076 Sq Ft
      • Built 2008
      429 Child Rd, Woodstock, CT 06281

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Jared Meehan RE/MAX Bell Park Realty

  • 0 Child Dome Rd Unit 24183838, Woodstock, CT 06281
    0 Child Dome Rd Unit 24183838, Woodstock, CT 06281
    0 Child Dome Rd Unit 24183838, Woodstock, CT 06281
    /3

    $179,000

    • Land
    • 2.9 Acres
    • $61,724 per Acre

    0 Child Dome Rd Unit 24183838, Woodstock, CT 06281

    Rare opportunity to own a large buildable lot in Woodstock, CT. This serene rear lot is located on one of the highest elevations in Woodstock. Surrounded by conservatory farmland, the views are for miles. The ride to this property, through the sparsely populated countryside, will surely give you the feel of the natural surroundings. Although located "far from the crowd" you are centrally located

    Bob Seele Coldwell Banker Realty

    0 Child Dome Rd Unit 24183838, Woodstock, CT 06281
  • 894 Route 169, Woodstock, CT 06281

    $357,000

    Sold Jun 26, 2026

    894 Route 169, Woodstock, CT 06281

    • 2 Beds
    • 1.5 Baths
    • 960 Sq Ft
    • Built 1975

    Last Sold Summary

    • 8% Above List Price
    • $372/SF
    • 3 Days On Market

    Current Estimated Value $337,642

    Last Listing Agent Valerie MacNeil Kazantzis Real Estate, LLC

    894 Route 169, Woodstock, CT 06281
    • 208 Baxter Rd, Woodstock, CT 06281

      Not Listed For Sale

      208 Baxter Rd, Woodstock, CT 06281

      • 2 Beds
      • 0.5 Baths
      • 480 Sq Ft
      • Built 1947
      208 Baxter Rd, Woodstock, CT 06281

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Kathleen Holland KW Legacy Partners

  • 0 Baxter Rd Unit 24177023, Woodstock, CT 06281
    0 Baxter Rd Unit 24177023, Woodstock, CT 06281
    0 Baxter Rd Unit 24177023, Woodstock, CT 06281
    /4

    $74,900

    $10K PRICE DROP
    • Land
    • 21,780 Sq Ft
    • $149,800 per Acre

    0 Baxter Rd Unit 24177023, Woodstock, CT 06281

    Build your dream home near the lake! This unique offering includes two adjoining parcels being sold together for a combined total of approximately 0.7 acres. The primary 0.5-acre parcel features a beautiful cleared and level homesite with open grassy space, ideal for new construction. Previous perc testing and a site development plan in 2008 outlines proposed home placement, septic system, and

    Donna Bertram Signature Properties of N.E.

    0 Baxter Rd Unit 24177023, Woodstock, CT 06281
  • 1226 Route 169, Wood Stock, CT 06281

    $199,900

    Sold Jul 24, 2026

    1226 Route 169, Wood Stock, CT 06281

    • 2 Beds
    • 1 Bath
    • 1,248 Sq Ft
    • Built 1890

    Last Sold Summary

    • $160/SF
    • 57 Days On Market

    Current Estimated Value $195,902

    Last Listing Agent Amy Vinal Pine Knoll Real Estate

    1226 Route 169, Wood Stock, CT 06281
    • 3 Holmeslea Ct, Woodstock, CT 06281

      Est $671,319

      Not Listed For Sale

      3 Holmeslea Ct, Woodstock, CT 06281

      • 5 Beds
      • 2.5 Baths
      • 3,526 Sq Ft
      • Built 1850
      3 Holmeslea Ct, Woodstock, CT 06281

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Mary Collins Berkshire Hathaway NE Prop.

  • 1250 Route 171, Woodstock, CT 06281
    1250 Route 171, Woodstock, CT 06281
    1250 Route 171, Woodstock, CT 06281
    /40

    $245,000

    $105K PRICE DROP Under Contract
    • 3 Beds
    • 1.5 Baths
    • 1,640 Sq Ft

    1250 Route 171, Woodstock, CT 06281

    Welcome to this charming colonial with stenciled details that add character & style! This delightful antique property is the perfect fixer upper and features 3 bedrooms, 1 and a 1/2 bathrooms, and a clapboard exterior. Situated on a 0.9 acre lot, this home boasts a garden in the side yard and a large backyard, perfect for outdoor enjoyment. Additionally, a shed provides convenient storage for

    Kara Mazzola First Choice Realty

    1250 Route 171, Woodstock, CT 06281
  • 43 Hiawatha Heights, Woodstock Valley, CT 06282

    $789,000

    Sold Aug 15, 2025

    43 Hiawatha Heights, Woodstock Valley, CT 06282

    • 2 Beds
    • 2 Baths
    • 1,918 Sq Ft
    • Built 1988

    Last Sold Summary

    • $411/SF
    • 42 Days On Market

    Current Estimated Value $827,157

    Last Listing Agent Jennie Kesselman Berkshire Hathaway NE Prop.

    43 Hiawatha Heights, Woodstock Valley, CT 06282
    • 739 Route 171, Woodstock, CT 06281

      Est $685,136

      Not Listed For Sale

      739 Route 171, Woodstock, CT 06281

      • 3 Beds
      • 2 Baths
      • 2,277 Sq Ft
      • Built 1977
      739 Route 171, Woodstock, CT 06281

      Last Sold Summary

      • 20 Days On Market

      Last Listing Agent Mary Collins Berkshire Hathaway NE Prop.

  • 186 Brickyard Rd, Woodstock, CT 06281
    186 Brickyard Rd, Woodstock, CT 06281
    186 Brickyard Rd, Woodstock, CT 06281
    /30

    $579,000

    $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,970 Sq Ft

    186 Brickyard Rd, Woodstock, CT 06281

    Enjoy the beautiful landscaping of this custom oversized ranch. Located on 6 acres, Recently cleared, private back yard perfect for entertaining, recreation and maybe a chicken or two. Double deck off the kitchen, that leads to above ground pool. This is your perfect summer spot! Kitchen with breakfast nook updated cabinets and stainless appliances, tile... Dining room follows kitchen to a one

    Amy Vinal Pine Knoll Real Estate

    186 Brickyard Rd, Woodstock, CT 06281
  • 16 Walnut Rd, Woodstock, CT 06281

    $409,900

    Sold Jul 31, 2026

    16 Walnut Rd, Woodstock, CT 06281

    • 3 Beds
    • 2 Baths
    • 1,242 Sq Ft
    • Built 2006

    Last Sold Summary

    • 3% Above List Price
    • $330/SF
    • 5 Days On Market

    Current Estimated Value $403,512

    Last Listing Agent Conrad Allen RE/MAX Professional Associates

    16 Walnut Rd, Woodstock, CT 06281
    • 1115 Route 169, Woodstock, CT 06281
      1115 Route 169, Woodstock, CT 06281
      1115 Route 169, Woodstock, CT 06281
      /39

      Est $515,121

      Not Listed For Sale

      1115 Route 169, Woodstock, CT 06281

      • 3 Beds
      • 2 Baths
      • 2,644 Sq Ft
      • Built 1986
      1115 Route 169, Woodstock, CT 06281

      Last Sold Summary

      • 214 Days On Market

      Last Listing Agent VIvian Kozey CR Premier Properties

  • 25 Woodstock Meadows, Woodstock, CT 06281
    25 Woodstock Meadows, Woodstock, CT 06281
    25 Woodstock Meadows, Woodstock, CT 06281
    /40

    $260,000

    Under Contract
    • 2 Beds
    • 1.5 Baths
    • 1,080 Sq Ft

    25 Woodstock Meadows, Woodstock, CT 06281

    Tucked away in the sought-after Woodstock Meadows community, this beautifully maintained townhouse offers the perfect balance of comfort, convenience, and small-town charm. Opportunities to own in this desirable neighborhood are few and far between, making this an exceptional place to be home. Enjoy the best of Woodstock living with historic Roseland Park and Golf Course just moments away, where

    Alexandria Kebalo RE/MAX One

    25 Woodstock Meadows, Woodstock, CT 06281

Showing Results 1 - 40, Page 1 of 18

Connecticut Windham County

Real Estate & Homes

Home Prices in Woodstock, CT

The median home sale price in Woodstock, CT is $437,500, up 2% year-over-year. Homes in Woodstock sell in 36 days on average, compared to the national average of 56 days.

Home Price Trends

Median Sale Price
$437,500
Median Single Family Sale Price
$466,000
Median 2 Bedroom Sale Price
$349,500
Median 1 Bedroom Sale Price
$268,000
Average Price Per Sq Ft
$299
Number of Homes for Sale
15
Last 12 months Home Sales
106
Months of Supply
1.70
Median List Price
$449,950
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
2%
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