1,669

Chester, CT Homes

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  • 47 E Kings Hwy, Chester, CT 06412
    47 E Kings Hwy, Chester, CT 06412
    47 E Kings Hwy, Chester, CT 06412
    /40

    $2,200,000

    • 4 Beds
    • 3.5 Baths
    • 3,957 Sq Ft

    47 E Kings Hwy, Chester, CT 06412

    A once-in-a-generation opportunity to become the steward of one of the Connecticut River Valley's most important historic estates. Built in 1798 by Jonathan Warner-founder of the Chester-Hadlyme Ferry, merchant, ship owner, farmer, Constable, Justice of the Peace, civic leader, and director of the Middlesex Turnpike-the Warner-Brooks House stands as a remarkable testament to early American

    Agent Photo

    Al Chiarito

    Chiarito Real Estate LLC

    47 E Kings Hwy, Chester, CT 06412
  • 159 W Main St Unit B, Chester, CT 06412
    159 W Main St Unit B, Chester, CT 06412
    159 W Main St Unit B, Chester, CT 06412
    /15

    $1,900 Per Month

    • 2 Beds
    • 1 Bath
    • 750 Sq Ft
    • Apartment for Rent

    159 W Main St Unit B, Chester, CT 06412

    LARGE 2 BEDROOM APARTMENT WITH NEWLY REDONE HARDWOOD FLOORS / FRESHLY PAINTED / UNIT HAS IT'S OWN FULL SIZE STACK WASHER & DRYER / UNIT IS RANCH ON THE SECOND FLOOR

    Tom Clancy William Pitt Sotheby's Int'l

    159 W Main St Unit B, Chester, CT 06412
  • 28 Hoop Pole Hill Rd, Chester, CT 06412

    $760,000

    Sold Nov 03, 2025

    28 Hoop Pole Hill Rd, Chester, CT 06412

    • 4 Beds
    • 3.5 Baths
    • 3,396 Sq Ft
    • Built 2008

    Last Sold Summary

    • 5% Below List Price
    • $224/SF
    • 83 Days On Market

    Current Estimated Value $815,621

    Last Listing Agent Teri Lewis William Pitt Sotheby's Int'l

    28 Hoop Pole Hill Rd, Chester, CT 06412
    • 75 Pinnacle Ln, Chester, CT 06412

      Est $926,204

      Not Listed For Sale

      75 Pinnacle Ln, Chester, CT 06412

      • 4 Beds
      • 3 Baths
      • 3,033 Sq Ft
      • Built 2006
      75 Pinnacle Ln, Chester, CT 06412

      Last Sold Summary

      • 20 Days On Market

      Last Listing Agent Kristen Butts Century 21 Clemens Group

  • 112 Oakwood Trail, Chester, CT 06412
    112 Oakwood Trail, Chester, CT 06412
    112 Oakwood Trail, Chester, CT 06412
    /39

    $599,900

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

    112 Oakwood Trail, Chester, CT 06412

    A distinctive offering in Chester's only 55+ condominium community, privately set along a quiet cul-de-sac. This beautifully appointed two-bedroom, two-and-a-half-bath residence pairs custom details with an open, light-filled design and a well-planned first-floor layout. The main living space features hardwood floors, abundant windows, and a gas fireplace creating a warm architectural focal

    Agent Photo

    Kelly Puorro

    Puorro Realty Group

    112 Oakwood Trail, Chester, CT 06412
  • 138 W Main St, Chester, CT 06412
    138 W Main St, Chester, CT 06412
    138 W Main St, Chester, CT 06412
    /13

    $1,695

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 700 Sq Ft
    • House for Rent

    138 W Main St, Chester, CT 06412

    Spacious one bedroom apartment in small quiet complex close to the quaint village of Chester. New kitchen, new carpet, wide plank floors, large windows, exposed beams in this antique colonial style restored barn, all set on well manicured grounds including stone walls and gardens; laundry in building; no dogs; easy access to I95 and Route 9. Tenant pays for electricity/heat/hot water. Rent $1695

    138 W Main St, Chester, CT 06412
  • 15 Hazen St, Chester, CT 06412

    $220,000

    Sold Apr 21, 2026

    15 Hazen St, Chester, CT 06412

    • 3 Beds
    • 1 Bath
    • 748 Sq Ft
    • Built 1900

    Last Sold Summary

    • 10% Above List Price
    • $294/SF
    • 14 Days On Market

    Current Estimated Value $222,309

    Last Listing Agent Anthony La Penna Exceptional Real Estate LLC

    15 Hazen St, Chester, CT 06412
    • 22 Hickory Hill Dr, Chester, CT 06412

      Est $571,542

      Not Listed For Sale

      22 Hickory Hill Dr, Chester, CT 06412

      • 3 Beds
      • 2.5 Baths
      • 1,838 Sq Ft
      • Built 1985
      22 Hickory Hill Dr, Chester, CT 06412

      Last Sold Summary

      • 49 Days On Market

      Last Listing Agent John Oliveri Property Works New England

  • 55 Wig Hill Rd, Chester, CT 06412
    55 Wig Hill Rd, Chester, CT 06412
    55 Wig Hill Rd, Chester, CT 06412
    /38

    $499,900

    • 3 Beds
    • 2 Baths
    • 1,774 Sq Ft

    55 Wig Hill Rd, Chester, CT 06412

    Set in the charming town of Chester, this three-bedroom, two-bath home offers a versatile layout with thoughtfully updated spaces throughout. The main level features an updated kitchen, wood floors, and an inviting living room anchored by a striking raised gas fireplace that serves as a beautiful focal point. Recent improvements include a new roof and new central air conditioning condenser,

    Agent Photo

    Kelly Puorro

    Puorro Realty Group

    55 Wig Hill Rd, Chester, CT 06412
  • 6 Pleasant St Unit 2, Chester, CT 06412
    6 Pleasant St Unit 2, Chester, CT 06412
    6 Pleasant St Unit 2, Chester, CT 06412
    /12

    $1,750 Per Month

    • 2 Beds
    • 1 Bath
    • 800 Sq Ft
    • House for Rent

    6 Pleasant St Unit 2, Chester, CT 06412

    CLEAN AND SPACIOUS 2 BEDROOM W/ LARGE EAT-IN KITCHEN / PAINTED AND REDONE HARDWOOD FLOORS / NEW REFRIGERATOR AND NEW ELECTRIC OVEN RANGE / HEAT, WATER & TRASH INCLUDED, PLUS A ONE CAR GARAGE!!! DOUBLE PANE INSULATED WINDOWS NICE OUTSIDE COVERED FRONT PORCH ~ I WOULD NOT WAIT ON THIS ONE!!

    Tom Clancy William Pitt Sotheby's Int'l

    6 Pleasant St Unit 2, Chester, CT 06412
  • 14 Ferry Rd, Chester, CT 06412

    $420,000

    Sold Sep 24, 2025

    14 Ferry Rd, Chester, CT 06412

    • 4 Beds
    • 1.5 Baths
    • 2,025 Sq Ft
    • Built 1950

    Last Sold Summary

    • 5% Above List Price
    • $207/SF
    • 35 Days On Market

    Current Estimated Value $440,772

    Last Listing Agent Ian Sacks Coldwell Banker Realty

    14 Ferry Rd, Chester, CT 06412
    • 69 Spring St, Chester, CT 06412

      Est $722,327

      Not Listed For Sale

      69 Spring St, Chester, CT 06412

      • 3 Beds
      • 1.5 Baths
      • 1,702 Sq Ft
      • Built 1883
      69 Spring St, Chester, CT 06412

      Last Sold Summary

      • 30 Days On Market

      Last Listing Agent Rachel Welch William Raveis Real Estate

  • 136 Goose Hill Rd, Chester, CT 06412
    136 Goose Hill Rd, Chester, CT 06412
    136 Goose Hill Rd, Chester, CT 06412
    /40

    $825,000

    $170K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 3,343 Sq Ft

    136 Goose Hill Rd, Chester, CT 06412

    Welcome to 136 Goose Hill Rd. This home has been tastefully redesigned inside and out with no expense spared. Featuring 4 bedroom, 3 full bathroom, over 3,300 sq ft of beautifully finished living space sitting on just over 2 acres. Step inside to discover all-new hardwood flooring throughout the main level and a thoughtfully designed open-concept layout ideal for both everyday living and

    Chris Torrez RE/MAX One

    136 Goose Hill Rd, Chester, CT 06412
  • 100 W Main St Unit A, Chester, CT 06412
    100 W Main St Unit A, Chester, CT 06412
    100 W Main St Unit A, Chester, CT 06412
    /18

    $2,300 Per Month

    • 1 Bed
    • 1 Bath
    • 750 Sq Ft
    • Apartment for Rent

    100 W Main St Unit A, Chester, CT 06412

    9/1/26 Move in! Taking applications. Something special is happening at 100 W Main. These brand-new residences bring together thoughtful design, beautiful finishes and the ease of modern living, all just minutes from the heart of Chester Village. Each home has its own personality, with carefully chosen kitchens and baths, warm wood tones, beautiful tilework, quality cabinetry and finishes that

    Aschly Daggett VC Property Group, LLC

    100 W Main St Unit A, Chester, CT 06412
  • 16 Sypher Rd, Chester, CT 06412

    $616,000

    Sold Jul 14, 2026

    16 Sypher Rd, Chester, CT 06412

    • 2 Beds
    • 2.5 Baths
    • 1,726 Sq Ft
    • Built 2004

    Last Sold Summary

    • 5% Above List Price
    • $357/SF
    • 42 Days On Market

    Current Estimated Value $581,237

    Last Listing Agent Peg Mitchel Coldwell Banker Realty

    16 Sypher Rd, Chester, CT 06412
    • 41 Railroad Ave, Chester, CT 06412

      Est $453,601

      Not Listed For Sale

      41 Railroad Ave, Chester, CT 06412

      • 2 Beds
      • 1 Bath
      • 1,771 Sq Ft
      • Built 1952
      41 Railroad Ave, Chester, CT 06412

      Last Sold Summary

      • 46 Days On Market

      Last Listing Agent Philip Warner William Pitt Sotheby's Int'l

  • 0 Turkey Hill Rd, Chester, CT 06412
    0 Turkey Hill Rd, Chester, CT 06412
    0 Turkey Hill Rd, Chester, CT 06412
    /19

    $75,000

    $25K PRICE DROP
    • Land
    • 1 Acre
    • $75,000 per Acre

    0 Turkey Hill Rd, Chester, CT 06412

    Discover the perfect setting to build your dream home in the desirable Wig Hill area of Chester, Connecticut. Located near Cockaponset Sate Forest and the scenic Connecticut River valley. This beautiful one-acre level building lot features approximately 211 feet of road frontage and dimensions of roughly 200 x 200 feet, offering ample space and flexibility to bring your custom plans and ideas to

    Charles Kroopneck Charles Kroopneck Real Estate

    0 Turkey Hill Rd, Chester, CT 06412
  • 100 W Main St Unit B, Chester, CT 06412
    100 W Main St Unit B, Chester, CT 06412
    100 W Main St Unit B, Chester, CT 06412
    /20

    $2,500 Per Month

    • 1 Bed
    • 1.5 Baths
    • 800 Sq Ft
    • Apartment for Rent

    100 W Main St Unit B, Chester, CT 06412

    Available 9/1/26! Taking applications now. Something special is happening at 100 W Main. This brand-new residence brings together thoughtful design, beautiful finishes, and the ease of modern living, all just minutes from the heart of Chester Village. **Unit B** has a style all its own. The bright, open living space centers around a beautifully finished kitchen with quartz countertops, a generous

    Aschly Daggett VC Property Group, LLC

    100 W Main St Unit B, Chester, CT 06412
  • 42 Straits Rd, Chester, CT 06412

    $460,000

    Sold Aug 21, 2026

    42 Straits Rd, Chester, CT 06412

    • 3 Beds
    • 2.5 Baths
    • 2,068 Sq Ft
    • Built 2003

    Last Sold Summary

    • 7% Below List Price
    • $222/SF
    • 6 Days On Market

    Current Estimated Value $498,378

    Last Listing Agent Stephanie Stone William Raveis/First Town RE

    42 Straits Rd, Chester, CT 06412
    • 248 Middlesex Ave, Chester, CT 06412

      Est $1,182,015

      Not Listed For Sale

      248 Middlesex Ave, Chester, CT 06412

      • 4 Beds
      • 3.5 Baths
      • 4,862 Sq Ft
      • Built 2007
      248 Middlesex Ave, Chester, CT 06412

      Last Sold Summary

      • 21 Days On Market

      Last Listing Agent Tammy Tinnerello William Pitt Sotheby's Int'l

  • 92 Water St, Chester, CT 06412
    92 Water St, Chester, CT 06412
    92 Water St, Chester, CT 06412
    /30

    $284,900

    • 3 Beds
    • 1 Bath
    • 1,217 Sq Ft

    92 Water St, Chester, CT 06412

    Charming 1927 Colonial offering a rare chance to own directly on the water in the heart of Chester. This 3-bedroom, 1-bath home spans 1,217 sq ft across two stories, with a classic layout featuring a living room and dining room on the main level and three bedrooms upstairs. Set on a 0.27-acre lot with vinyl siding and a paved driveway, the home sits right on the water with tranquil river views -

    Ryan O'Keeffe Salzillo Realty Company

    92 Water St, Chester, CT 06412
  • 7 Hickory Hill Dr, Chester, CT 06412

    $549,000

    Sold Mar 24, 2026

    7 Hickory Hill Dr, Chester, CT 06412

    • 3 Beds
    • 2.5 Baths
    • 2,202 Sq Ft
    • Built 1984

    Last Sold Summary

    • $249/SF
    • 6 Days On Market

    Current Estimated Value $564,416

    Last Listing Agent Craig Milton Re/Max Valley Shore

    7 Hickory Hill Dr, Chester, CT 06412
    • 25 Deep Hollow Rd, Chester, CT 06412

      Est $577,868

      Not Listed For Sale

      25 Deep Hollow Rd, Chester, CT 06412

      • 3 Beds
      • 2.5 Baths
      • 1,710 Sq Ft
      • Built 1993
      25 Deep Hollow Rd, Chester, CT 06412

      Last Sold Summary

      • 18 Days On Market

      Last Listing Agent Craig Milton Re/Max Valley Shore

  • 59 Maple St, Chester, CT 06412
    59 Maple St, Chester, CT 06412
    59 Maple St, Chester, CT 06412
    /37

    $1,995,000

    $105K PRICE DROP Under Contract
    • 11 Beds
    • 12 Baths
    • 8,500 Sq Ft

    59 Maple St, Chester, CT 06412

    A mixed-use and multifamily package located in Chester and Deep River, two of the most desirable towns in the Lower Connecticut River Valley. The offering includes: 59 Maple Street (Chester): 7-unit multifamily asset with an additional ~1,500 SF commercial warehouse on 2.5+ acres. 163 Main Street (Deep River): 5-unit mixed-use property positioned at the gateway to the downtown retail corridor.

    Connor Wenchell VC Property Group, LLC

    59 Maple St, Chester, CT 06412
  • 3 Kirtland Ave, Chester, CT 06412

    $233,600

    Sold Jul 23, 2026

    3 Kirtland Ave, Chester, CT 06412

    • 2 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Built 2025

    Last Sold Summary

    • 17% Below List Price
    • $174/SF
    • 52 Days On Market

    Current Estimated Value $290,329

    Last Listing Agent Sherry Price Realhome Services & Solutions

    3 Kirtland Ave, Chester, CT 06412
    • 31 Parkers Point Rd, Chester, CT 06412

      Est $2,988,425

      Not Listed For Sale

      31 Parkers Point Rd, Chester, CT 06412

      • 3 Beds
      • 3.5 Baths
      • 4,727 Sq Ft
      • Built 2010
      31 Parkers Point Rd, Chester, CT 06412

      Last Sold Summary

      • 27 Days On Market

      Last Listing Agent Colette Harron William Pitt Sotheby's Int'l

  • 288 Middlesex Ave, Chester, CT 06412
    288 Middlesex Ave, Chester, CT 06412
    288 Middlesex Ave, Chester, CT 06412
    /38

    $2,995,000

    • 4 Beds
    • 6 Baths
    • 4,926 Sq Ft

    288 Middlesex Ave, Chester, CT 06412

    Set along a coveted and historic stretch of the Connecticut River, East View is a rare waterfront compound where extraordinary frontage, architectural integrity and Connecticut River Valley charm converge. Just over one mile from the village, this turnkey 2.65-acre estate offers 285 feet of direct river frontage, protected views and deep-water access. The river is the focal point framed by

    Nancy Mesham Coldwell Banker Realty

    288 Middlesex Ave, Chester, CT 06412
  • 25 Spring St, Chester, CT 06412

    $860,000

    Sold Sep 17, 2025

    25 Spring St, Chester, CT 06412

    • 3 Beds
    • 2.5 Baths
    • 2,344 Sq Ft
    • Built 1860

    Last Sold Summary

    • 4% Below List Price
    • $367/SF
    • 38 Days On Market

    Current Estimated Value $833,985

    Last Listing Agent Susan Malan William Pitt Sotheby's Int'l

    25 Spring St, Chester, CT 06412
    • 32 Gilbert Hill Rd, Chester, CT 06412

      Est $1,005,788

      Not Listed For Sale

      32 Gilbert Hill Rd, Chester, CT 06412

      • 3 Beds
      • 3 Baths
      • 3,788 Sq Ft
      • Built 1986
      32 Gilbert Hill Rd, Chester, CT 06412

      Last Sold Summary

      • 70 Days On Market

      Last Listing Agent Steve Q Exclusive Properties

  • 11 Castle View Dr, Chester, CT 06412
    11 Castle View Dr, Chester, CT 06412
    11 Castle View Dr, Chester, CT 06412
    /28

    $496,900

    Pending
    • 3 Beds
    • 2 Baths
    • 2,103 Sq Ft

    11 Castle View Dr, Chester, CT 06412

    Offered for sale for the very first time, this lovingly cared-for home is a rare opportunity in the welcoming Castle View Drive neighborhood, just moments from Chester Center. While the manicured lawn, mature gardens, and meticulous exterior maintenance create an excellent first impression, this home is much larger than it appears from the front elevation. Step inside and discover a spacious

    Cortney Emshwiller-Swokla Coldwell Banker Realty

    11 Castle View Dr, Chester, CT 06412
  • 12 Deep Hollow Rd, Chester, CT 06412

    $319,900

    Sold Jan 20, 2026

    12 Deep Hollow Rd, Chester, CT 06412

    • 3 Beds
    • 1 Bath
    • 912 Sq Ft
    • Built 1960

    Last Sold Summary

    • $351/SF
    • 52 Days On Market

    Current Estimated Value $329,476

    Last Listing Agent Craig Milton Re/Max Valley Shore

    12 Deep Hollow Rd, Chester, CT 06412
    • 137 Main St, Chester, CT 06412

      Est $607,931

      Not Listed For Sale

      137 Main St, Chester, CT 06412

      • 3 Beds
      • 1.5 Baths
      • 1,570 Sq Ft
      • Built 1915
      137 Main St, Chester, CT 06412

      Last Sold Summary

      • 15 Days On Market

      Last Listing Agent Teri Lewis William Pitt Sotheby's Int'l

  • 90 Water St, Chester, CT 06412
    90 Water St, Chester, CT 06412
    90 Water St, Chester, CT 06412
    /24

    $269,900

    • 1 Bed
    • 1 Bath
    • 1,034 Sq Ft

    90 Water St, Chester, CT 06412

    Rare opportunity to own directly on the water in the heart of Chester. This 1950-built ranch offers 1,034 sq ft with a flexible layout - currently set up as a 1-bedroom, the spacious family room (10'3" x 20'10") could easily convert to a second bedroom or home office. The oversized living room (13'6" x 20'10") anchors the home, while the combined kitchen/dining area (10'5" x 16'2") and

    Ryan O'Keeffe Salzillo Realty Company

    90 Water St, Chester, CT 06412
  • 30 Bokum Rd, Chester, CT 06412

    $442,500

    Sold Oct 20, 2025

    30 Bokum Rd, Chester, CT 06412

    • 3 Beds
    • 2 Baths
    • 1,198 Sq Ft
    • Built 1930

    Last Sold Summary

    • 4% Above List Price
    • $369/SF
    • 59 Days On Market

    Current Estimated Value $445,425

    Last Listing Agent Max Gill Puorro Realty Group

    30 Bokum Rd, Chester, CT 06412
    • 12 Liberty St, Chester, CT 06412

      Est $723,383

      Not Listed For Sale

      12 Liberty St, Chester, CT 06412

      • 3 Beds
      • 2.5 Baths
      • 2,713 Sq Ft
      • Built 1925
      12 Liberty St, Chester, CT 06412

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Rick Weiner William Pitt Sotheby's Int'l

  • 0 Goose Hill Rd Unit 24180404, Chester, CT 06412
    0 Goose Hill Rd Unit 24180404, Chester, CT 06412
    0 Goose Hill Rd Unit 24180404, Chester, CT 06412
    /6

    $145,000

    Under Contract
    • Land
    • 4.91 Acres
    • $29,532 per Acre

    0 Goose Hill Rd Unit 24180404, Chester, CT 06412

    New to the market! Discover the perfect canvas for your dream home on this beautiful, private 4.91-acre wooded lot. Nestled within a private 8-lot subdivision just off Goose Hill Road, this parcel offers a rare blend of ultimate privacy and convenience, featuring excellent frontage on a paved, private road. The location is truly unbeatable, sitting just over a mile from the charming, historic

    Amy Graham William Pitt Sotheby's Int'l

    0 Goose Hill Rd Unit 24180404, Chester, CT 06412
  • 14 Maple St, Chester, CT 06412

    $810,000

    Sold Nov 14, 2025

    14 Maple St, Chester, CT 06412

    • 3 Beds
    • 3.5 Baths
    • 2,322 Sq Ft
    • Built 1755

    Last Sold Summary

    • 1% Above List Price
    • $349/SF
    • 6 Days On Market

    Current Estimated Value $834,210

    Last Listing Agent Deborah Rowe William Raveis Real Estate

    14 Maple St, Chester, CT 06412
    • 230 W Main St, Chester, CT 06412

      Est $423,629

      Not Listed For Sale

      230 W Main St, Chester, CT 06412

      • 2 Beds
      • 1.5 Baths
      • 1,530 Sq Ft
      • Built 1986
      230 W Main St, Chester, CT 06412

      Last Sold Summary

      • 24 Days On Market

      Last Listing Agent Siobhan McLaughlin William Raveis Real Estate

  • 135 Middlesex Ave, Chester, CT 06412
    135 Middlesex Ave, Chester, CT 06412
    135 Middlesex Ave, Chester, CT 06412
    /35

    $499,000

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

    135 Middlesex Ave, Chester, CT 06412

    NEW PRICE!! Beautiful view from this WATERFRONT home on Chester Cove! Steps to fishing or kayaking just out your door. Enjoy watching the wildlife from the 20x10 deck directly off the kitchen/dining/living rooms. Wonderful light enters through the abundant windows on the first floor with its open floor plan, kitchen with granite, newer appliances and a window over the kitchen sink you won't want

    Lisa Genovali Re/Max Valley Shore

    135 Middlesex Ave, Chester, CT 06412
  • 6 Jagger Ln, Chester, CT 06412

    $805,000

    Sold Sep 01, 2026

    6 Jagger Ln, Chester, CT 06412

    • 2 Beds
    • 2.5 Baths
    • 2,428 Sq Ft
    • Built 1901

    Last Sold Summary

    • $332/SF
    • 89 Days On Market

    Current Estimated Value $787,222

    Last Listing Agent Maddy Mattson Coldwell Banker Realty

    6 Jagger Ln, Chester, CT 06412

Showing Results 1 - 40, Page 1 of 18

Connecticut Middlesex County

Real Estate & Homes

Home Prices in Chester, CT

The median home sale price in Chester, CT is $565,000, up 5% year-over-year. Homes in Chester sell in 63 days on average, compared to the national average of 55 days.

Home Price Trends

Median Sale Price
$565,000
Median Single Family Sale Price
$550,000
Median 2 Bedroom Sale Price
$565,000
Median 1 Bedroom Sale Price
$269,900
Average Price Per Sq Ft
$337
Number of Homes for Sale
8
Last 12 months Home Sales
38
Months of Supply
2.50
Median List Price
$567,500
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
5%
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