38

Windsor, CT Houses for Sale

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  • /27

    $329,925

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

    41 Chestnut Dr, Windsor, CT 06095

    Welcome to 41 Chestnut Drive, a charming and well-maintained Cape Cod style home nestled in a quiet Windsor neighborhood, perfect for those seeking comfort, convenience, and classic New England character. This bright and inviting residence has 2 spacious bedrooms with a possible 3rd, 2 full baths, with a flexible floor plan that blends functionality and warmth. A spacious kitchen with ample

    Agent Photo

    Jason Kemp

    Five Stars Realty

    (860) 981-0837

    41 Chestnut Dr, Windsor, CT 06095
  • /2

    $259,900

    • 3 Beds
    • 2.5 Baths
    • 1,194 Sq Ft

    99 Pepperbush Way, Windsor, CT 06095

    3-bedroom, 2.5-bath raised ranch offering comfort and convenience in a desirable setting. This home features a 2-car attached garage, natural gas heat, and public utilities for ease of living. The lower level offers even more living space with a family room, half bath, laundry, and direct access to the garage. With its functional floor plan and sought-after utilities, this home is ready for its

    Agent Photo

    Amy Rio

    Executive Real Estate Inc.

    (860) 300-2726

    99 Pepperbush Way, Windsor, CT 06095
  • /28

    $449,900

    • 3 Beds
    • 3 Baths
    • 1,848 Sq Ft

    680 Kennedy Rd, Windsor, CT 06095

    Welcome Home to a Stunning, freshly renovated ranch that combines modern style with classic comfort. This move-in-ready home features a brand-new roof and siding, offering excellent curb appeal and peace of mind for years to come. Inside, you'll find a bright and airy layout with new flooring, fresh paint, and thoughtful finishes throughout. The updated kitchen boasts sleek countertops, stainless

    Timothy Faucher eXp Realty

    680 Kennedy Rd, Windsor, CT 06095
  • /40

    $424,900

    • 4 Beds
    • 1.5 Baths
    • 2,564 Sq Ft

    16 Crabapple Rd, Windsor, CT 06095

    Discover exceptional living in this pristine and stunning four bedroom New England Colonial home, nestled on a gorgeous .42 acre lot. Boasting modern updates and classic charm, this property combines elegance and convenience in a peaceful and sought after neighborhood. The fully remodeled kitchen features an abundance of maple cabinetry, granite counter tops, stainless steel appliances, tile back

    John Waters Berkshire Hathaway NE Prop.

    16 Crabapple Rd, Windsor, CT 06095
  • /36

    $469,900

    • 3 Beds
    • 2 Baths
    • 1,850 Sq Ft

    29 Quail Hollow Dr, Windsor, CT 06095

    Welcome home! This beautifully maintained Raised Ranch offers the perfect blend of comfort, style, and outdoor luxury. When you step outside, prepare to be wowed! A two-tiered deck overlooks a fully fenced-in, expansive backyard designed for pure enjoyment. Take a dip in the heated in-ground saltwater pool, unwind in the hot tub, or host unforgettable gatherings on the stamped concrete pool deck

    Michael Zizzamia William Raveis Real Estate

    29 Quail Hollow Dr, Windsor, CT 06095
  • /31

    $489,999

    • 4 Beds
    • 3 Baths
    • 2,208 Sq Ft

    9 Meadowlark Dr, Windsor, CT 06095

    Welcome to this beautifully refreshed Cape-style home offering 4 spacious bedrooms and 3 full bathrooms. This home features a bright and welcoming interior and is move-in ready! The main level includes a comfortable bedroom and a full bathroom, perfect for flexible living arrangements. You'll also find an inviting living area, dining room, family room, a well-appointed kitchen with ample

    Maritza Zavala Naples Realty Group, LLC

    9 Meadowlark Dr, Windsor, CT 06095
  • /36

    $390,000

    • 3 Beds
    • 2.5 Baths
    • 1,189 Sq Ft

    145 Park Ave, Windsor, CT 06095

    Look no Further! As this Move in Ready, meticulously maintained beautiful raised Ranch home with stunning curb appeal, carefully designed opened concept floor plan, is a great home for you!.This wonderful Home boasts 3 spacious bedrooms, with each room having lots of closet space.The main Bedroom features it's own bathroom,Home has 2.5 beautiful and fully renovated baths, gleaming Hardwood floors

    Dadrie Broderick Coldwell Banker Realty

    145 Park Ave, Windsor, CT 06095
  • /30

    $420,000

    • 3 Beds
    • 2.5 Baths
    • 1,912 Sq Ft

    190 Prospect Hill Rd, Windsor, CT 06095

    Welcome to this lovely 3-bedroom, 2.5-bath colonial nestled in a quiet Windsor neighborhood. A welcoming front porch awaits your finishing touches - the perfect spot to greet guests or enjoy a morning coffee. Inside, you'll find an updated kitchen that opens seamlessly into the living room, featuring a cozy fireplace, perfect for relaxing or entertaining. The oversized primary bedroom offers a

    Shannon King Cozy Homes Real Estate

    190 Prospect Hill Rd, Windsor, CT 06095
  • /40

    $499,900

    • 4 Beds
    • 2.5 Baths
    • 2,360 Sq Ft

    10 Cleary Ln, Windsor, CT 06095

    Nestled on a quiet cul-de-sac, this beautiful 4-bedroom, 2.1-bath ranch offers over 2,300 sq. ft. of stylish living space. The sunken living room is a true showstopper, featuring dramatic floor-to-ceiling windows that flood the space with natural light. A spacious dining room overlooks the living area, creating an open and inviting layout perfect for gatherings. The master suite and family room

    Tammy Ferrauola Eagle Eye Realty PLLC

    10 Cleary Ln, Windsor, CT 06095
  • /24

    $399,900

    • 4 Beds
    • 2 Baths
    • 1,603 Sq Ft

    28 Sunnyfield Dr, Windsor, CT 06095

    Welcome to 28 Sunnyfield Drive, a beautifully renovated 4-bedroom, 2-bath Colonial in the heart of Windsor. Every detail has been thoughtfully updated, offering over 1,600 sq. ft. of modern living space plus a finished basement. The brand-new kitchen shines with stylish finishes and flows seamlessly into bright, open living areas. Enjoy the convenience of an official laundry room and relax on one

    Christian Rivas Plata Complete Real Estate

    28 Sunnyfield Dr, Windsor, CT 06095
  • /19

    $405,000

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

    119 Joshua Hill, Windsor, CT 06095

    Welcome home to 119 Joshua Hill! This contemporary 3 bedroom, 2 bath home is located in one of Windsor's most sought-after neighborhoods and offers a bright and functional layout. The main level features a welcoming foyer, spacious living room, dining room, and eat-in kitchen with ample cabinetry and counter space. The upper level is dedicated to the primary bedroom and full bath, while the

    Nicole Crenshaw Barile Realty Group

    119 Joshua Hill, Windsor, CT 06095
  • /38

    $399,900

    • 4 Beds
    • 2 Baths
    • 1,804 Sq Ft

    1476 Poquonock Ave, Windsor, CT 06095

    Welcome to 1476 Poquonock Avenue in Windsor! This meticulously maintained Colonial offers the perfect blend of character and space. Featuring 4 bedrooms and 2 full bathrooms, this home showcases beautiful hardwood floors throughout. The partially finished attic offers flexible space, ideal for a home office, playroom, or guest retreat. The basement is also partially finished, complete with a

    Kervin Figaro Five Stars Realty

    1476 Poquonock Ave, Windsor, CT 06095
  • /28

    $421,000

    • 4 Beds
    • 3 Baths
    • 2,738 Sq Ft

    957 Palisado Ave, Windsor, CT 06095

    Welcome to this charming 1773 center chimney colonial in the highly desirable town of Windsor ,CT built on over an acre of land. This classic property blends old-world charm with modern conveniences. Upon arrival you will enter a spacious, updated eat-in country kitchen with a beehive oven for family gatherings. French doors open from the kitchen out onto a large slate patio with a beautiful

    Steven Koleno Beycome of Connecticut

    957 Palisado Ave, Windsor, CT 06095
  • /33

    $409,000 Open Sat 12PM - 2PM

    • 3 Beds
    • 1.5 Baths
    • 1,533 Sq Ft

    1492 Poquonock Ave, Windsor, CT 06095

    Welcome to a rare and exceptional opportunity to own a ranch-style home that combines timeless charm, solid construction, and the serene privacy of over 4 sprawling acres. Set against the backdrop of natural beauty and open skies, this well-maintained property offers the perfect blend of rural living and modern comfort-making it a true haven for those seeking space, tranquility, and functionality

    Brielle Browne William Pitt Sotheby's Int'l

    1492 Poquonock Ave, Windsor, CT 06095
  • /37

    $400,000 Open Sun 1PM - 3PM

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

    21 Long Hill Rd, Windsor, CT 06095

    Step inside this beautifully maintained raised ranch offering 3 comfortable bedrooms and 2.5 bathrooms in a bright, inviting space. The main level features an open concept living and dining area perfect for everyday living and entertaining. The kitchen provides plenty of counter space with granite countertops, under cabinet lighting, Bosch double ovens for all your cooking or baking needs, as

    Paul Striefler LPT Realty

    21 Long Hill Rd, Windsor, CT 06095
  • /31

    $334,900

    • 3 Beds
    • 1 Bath
    • 1,670 Sq Ft

    25 Maude Cir, Windsor, CT 06095

    Welcome to this charming well-maintained 3-bedroom, 1-bath single-family ranch nestled at the end of a peaceful cul-de-sac. This home offers 1,152 sq ft of comfortable living space with an additional 518 sq ft of partially finished basement-perfect for a home office, gym, or playroom. Step inside to find beautiful hardwood floors throughout the main level, and a bright, airy layout that includes

    Sharon Fox Carl Guild & Associates

    25 Maude Cir, Windsor, CT 06095
  • /39

    $319,900

    • 3 Beds
    • 1.5 Baths
    • 1,440 Sq Ft

    580 W Wolcott Ave, Windsor, CT 06095

    Charming brick home nestled on 2.7 acres of beautiful level lot. to create your own peaceful oasis. 3 spacious bedrooms (with 1 on the main level). The main floor welcomes you with sunny and bright cozy living room with a fireplace. The dining room is open to the recently remodeled beautiful kitchen with granite counter tops, stainless steel appliances and a eat-in kitchen island. The upper

    Ola Aly Berkshire Hathaway NE Prop.

    580 W Wolcott Ave, Windsor, CT 06095
  • /39

    $374,900

    • 4 Beds
    • 2.5 Baths
    • 1,526 Sq Ft

    94 Clubhouse Rd, Windsor, CT 06095

    Waterfront Living on the Farmington River! This Custom Contemporary Home Delivers The Lifestyle Most Only Dream About. Wake Up To Sparkling River Views And End Your Day With Sunsets Over The Water. Step Inside And Be Amazed At Just How Spacious This Home Is! The Open-Concept Main Level Is Perfect For Gathering, With A Sun-Filled Living Area, Kitchen and 2 Bedrooms ~ One With A Private Deck Where

    Eden Wimpfheimer Berkshire Hathaway NE Prop.

    94 Clubhouse Rd, Windsor, CT 06095
  • /28

    $309,900

    • 3 Beds
    • 2 Baths
    • 1,181 Sq Ft

    3 Saville St, Windsor, CT 06095

    This renovated 3-bedroom, 2-bathroom home offers the perfect blend of comfort, functionality, and location. Step inside to discover a warm and welcoming layout with spacious living areas and a finished basement that adds valuable bonus space - perfect for a home office, gym, or media room. This home also features an attached garage for added convenience. You'll also enjoy being just a short walk

    Fabian Weir PrefeQ Realty

    3 Saville St, Windsor, CT 06095
  • /19

    $329,900

    • 3 Beds
    • 2.5 Baths
    • 1,352 Sq Ft

    107 Sunnyfield Dr, Windsor, CT 06095

    Scenic setting for this 7 room, 3 bedroom, 2.5-bath raised ranch with lower-level rec room. A paver driveway and walkways lead to the home. The fully fenced backyard features a 16' x 16' deck and a storage shed. Interior will need updating and has a strong cigarette odor. Central air and forced hot air systems are not operational; the hot water boiler is currently functioning. Property is being

    Ben Castonguay Sentry Real Estate

    107 Sunnyfield Dr, Windsor, CT 06095
  • /36

    $359,000

    • 4 Beds
    • 3 Baths
    • 1,790 Sq Ft

    25 Patriot Rd, Windsor, CT 06095

    Welcome to 25 Patriot Road, a beautifully updated raised ranch located in a quiet Windsor neighborhood. This move-in-ready home features new windows, refinished hardwood floors, and a bright, open layout perfect for modern living. The spacious living room flows into the dining area and an inviting kitchen with access to the back deck - ideal for entertaining or enjoying your morning coffee. The

    Reza Abbassi New Door Realty

    25 Patriot Rd, Windsor, CT 06095
  • /36

    $279,900

    • 3 Beds
    • 1.5 Baths
    • 1,495 Sq Ft

    20 Sage Park Rd, Windsor, CT 06095

    Great location. Walk to school and parks.

    Joe Aloisa Coldwell Banker Realty

    20 Sage Park Rd, Windsor, CT 06095
  • /34

    $334,900

    • 4 Beds
    • 1 Bath
    • 1,305 Sq Ft

    8 Aramamet St, Windsor, CT 06095

    Beautifully Updated Craftsman Home This classic Craftsman home welcomes you with a wide covered front porch framed by tapered columns-perfect for morning coffee or evening relaxation. Inside, you'll find sun-filled rooms with gleaming hardwood floors, rich wood trim, and original built-ins that showcase timeless character. The kitchen offers modern convenience with ample storage and counter

    Gregory Wright Great Estates, CT

    8 Aramamet St, Windsor, CT 06095
  • /37

    $370,000

    • 3 Beds
    • 1.5 Baths
    • 1,558 Sq Ft

    41 Hale Dr, Windsor, CT 06095

    Welcome to this stunning split-level home tucked away on a quiet cul-de-sac! Fully renovated in 2018, this home offers a modern, spacious feel with perfectly designed separate 'zones'. From the bedroom zone, step onto the open balcony overlooking the bright and airy main living zone. Just a few steps down, you'll find the open-concept kitchen with granite countertops flowing beautifully into the

    Jeffrey Hiser Berkshire Key Realty

    41 Hale Dr, Windsor, CT 06095
  • /25

    $250,000

    • 3 Beds
    • 1.5 Baths
    • 1,253 Sq Ft

    39 Warham St, Windsor, CT 06095

    Welcome to 39 Warham Street, a warm and inviting home that blends classic charm with everyday comfort. With over 1,250 square feet, this well-laid-out colonial features three bedrooms, one and a half bathrooms, and plenty of space both inside and out. Step onto the welcoming front porch and into a home filled with natural light and character. To the left is a cozy family room, perfect for

    Mark Mermelstein eXp Realty

    39 Warham St, Windsor, CT 06095
  • /33

    $489,000

    • 5 Beds
    • 2.5 Baths
    • 2,741 Sq Ft

    27 Valley View Dr, Windsor, CT 06095

    This colonial oversize colonial has all the space to grow and build new memories within. Close to major highways this property blends both proximity to peace, quiet and active lifestyle

    Andre Holloman KW Legacy Partners

    27 Valley View Dr, Windsor, CT 06095
  • /40

    $335,000

    • 3 Beds
    • 1 Bath
    • 1,128 Sq Ft

    175 E Pershing St, Bloomfield, CT 06002

    Welcome to 175 E Pershing Street-a beautifully renovated home nestled on a dead end street in one of Windsor's most charming neighborhoods. This turn-key, move-in ready property features 3 spacious bedrooms and a modern open-concept kitchen, living, and dining area-perfect for today's lifestyle and entertaining. Every detail has been thoughtfully updated, from the brand-new roof and gutters to

    Christian Flores mygoodagent

    175 E Pershing St, Bloomfield, CT 06002
  • /31

    $574,900

    • 6 Beds
    • 4 Baths
    • 2,984 Sq Ft

    30 Parkwood Dr, Windsor, CT 06095

    Welcome to 30 Parkwood Drive, an expansive and beautifully Dutch colonial home offering 6 bedrooms, 2 full baths, and 2 half baths sitting at the end of a cul de sac in Windsor. This versatile and spacious layout is perfect for today's lifestyles whether you need multiple home offices, guest rooms, or space for extended guest. Step inside to find sun-filled living areas and a kitchen featuring

    Kervin Figaro Five Stars Realty

    30 Parkwood Dr, Windsor, CT 06095
  • /30

    $425,000

    • 3 Beds
    • 2 Baths
    • 1,715 Sq Ft

    16 Hilltop Rd, Windsor, CT 06095

    Updated Raised Ranch on 0.75 Acres in Windsor! Beautifully remodeled in 2017 and meticulously maintained, this 3-bedroom, 2-bath Raised Ranch offers move-in-ready comfort with all major updates complete. The main level features an open-concept layout with a remodeled kitchen showcasing granite countertops, an island, and stainless steel appliances, seamlessly flowing into the dining and living

    Joe Coelho Coldwell Banker Realty

    16 Hilltop Rd, Windsor, CT 06095
  • /16

    $344,900

    • 4 Beds
    • 2 Baths
    • 2,402 Sq Ft

    39 Loren Cir, Windsor, CT 06095

    Spacious 4-bedroom, 2-bathroom Contemporary home on a cul-de-sac. The open floor plan includes over 2400 sq ft with a grand entrance view of the upper loft. Features include a primary bedroom suite with a walk-in closet, 1st floor and 2nd floor bedrooms, a large extra room with woodstove and slider leading to the private level back yard. Enjoy the CAir on these hot summer days. Newer hot water

    Lavasha Bester CENTURY 21 AllPoints Realty

    39 Loren Cir, Windsor, CT 06095
  • /36

    $436,000

    • 3 Beds
    • 2.5 Baths
    • 1,952 Sq Ft

    58 Amanda Cir, Windsor, CT 06095

    PRICED TO SELL: MAJOR DISCOUNT & FLEXIBLE PRICING! Seller is relocating out of state and wants a FAST closing! A great deal on a HEALTHY home. Key Features and Upgrades: -Solid and Move-In Ready: Roof has 15+ years of life remaining, heating system recently serviced, and all appliances in great condition. -Energy Efficient and Secure: Solar panels with backup solar generator, real-time monitored

    Steven Koleno Beycome of Connecticut

    58 Amanda Cir, Windsor, CT 06095
  • /37

    $579,900 New Construction

    • 3 Beds
    • 2 Baths
    • 1,880 Sq Ft

    318 Capen St, Windsor, CT 06095

    COOK HILL - Windsor Development! "The Cindy Lou MODEL!" Gorgeous Ranch style home w/covered front porch and back porch. Open Kitchen, Living Room and Dining Room w/Cathedral ceilings. Unique second suite and office. Large mudroom with Laundry, Master suite w/Cathedral ceilings and Huge walk-in closet. Wonderful Open Floor Plan, Rare Find with plentiful Living space, granite countertops in

    Lori Gabriel Coldwell Banker Realty

    318 Capen St, Windsor, CT 06095
  • /6

    $569,900 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,800 Sq Ft

    342 Capen St, Windsor, CT 06095

    Desirable Cook Hill - Don't Miss Out! "The Darlene Model" Offers 1,800SF of thoughtfully designed Living with 3 Bedrooms, 2.5 Baths, a 2-Car Garage, second-floor Laundry, and a versatile Office Nook. Each home features a Ready-Finish Basement/Foundation, making it easy to finish the lower level for a future Mancave, Family room, or extra Living space. Built for Energy Efficiency and modern

    Lori Gabriel Coldwell Banker Realty

    342 Capen St, Windsor, CT 06095
  • /5

    $579,900 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,800 Sq Ft

    26 Cook Hill Rd, Windsor, CT 06095

    NEW CONSTRUCTION COLONIAL! Don't miss this RARE OPPORTNITY to own the Brand-new Darlene Model in the highly sought-after Cook Hill neighborhood! This thoughtfully designed 1,800 SF home offers 3 spacious Bedrooms, 2.5 Baths, a 2-Car Garage, 2nd-floor Laundry, and a versatile large Office Nook/Loft, perfect for modern Family living or remote work. Inside, you'll find Modern Lighting, white doors

    Lori Gabriel Coldwell Banker Realty

    26 Cook Hill Rd, Windsor, CT 06095
  • /22

    $499,990 Pre-Foreclosure

    • 3 Beds
    • 3.5 Baths
    • 2,673 Sq Ft

    1 Deanne Lynn Cir, Windsor, CT 06095

    Come home every day to this spectacular custom-built contemporary set on a beautiful .65-acre lot in the prestigious Kendrick Place neighborhood. The dramatic open foyer features marble flooring, an elegant staircase, and a balcony that overlooks the stunning great room with its 16-foot vaulted ceiling, fireplace, and expansive windows that flood the space with southern light. The updated

    Kostas Travisano Sailpoint Property Group

    1 Deanne Lynn Cir, Windsor, CT 06095
  • /36

    $325,000 Coming Soon

    • 4 Beds
    • 2 Baths
    • 2,520 Sq Ft

    351 Rainbow Rd, Windsor, CT 06095

    Tucked away off the road in historic Windsor, CT, this charming antique home sits gracefully on a private half-acre lot. Steeped in character, it features unique original wood flooring throughout most of the home, preserving its timeless appeal, with updated surfaces in the kitchen and baths for modern comfort. The spacious, eat-in kitchen offers an abundance of cabinets and generous counter

    Diane Q McHugh Berkshire Hathaway NE Prop.

    351 Rainbow Rd, Windsor, CT 06095
  • /32

    $300,000 Open Sat 1:30PM - 2:30PM

    • 3 Beds
    • 2.5 Baths
    • 1,532 Sq Ft

    2 Sandra Dr, Bloomfield, CT 06002

    This 1982 saltbox style home is on a corner lot in a quiet part of Bloomfield. It has a large, flat yard, with a backyard that's fenced-in. The long driveway has space for up to 8 cars, so parking will never be a problem. Gleaming hardwood floors on the main level. Plenty of space with its four bedrooms and two and a half bathrooms. The finished lower level is fully above-grade with full-sized

    Austin Miglin Realty Negotiations LLC

    2 Sandra Dr, Bloomfield, CT 06002
  • /11

    $990,000

    • 2 Beds
    • 3 Baths
    • 1,974 Sq Ft

    49 Seymour Rd, East Granby, CT 06026

    A Equestrian lovers delight- a unique opportunity to own 32 acres complete with renovated colonial style home and 15 stall barn with second story finished loft. This 1,925 square foot single family home has 2 bedrooms extra room that can be used as an extra bedroom and 3.0 bathrooms with a 2 car garage. There is a separate apartment above stalls and a room to add half bath in stall area. Large

    George Agnelli Agnelli Real Estate

    49 Seymour Rd, East Granby, CT 06026

Why Live in Windsor

Windsor, Connecticut, known for its historical significance as one of the first towns in the state, offers a mix of established and new homes, including Cape Cod, Colonial Revival, and ranch-style designs. The community is conveniently located near major highways like I-91 and I-291, providing easy access to New York and Hartford. Windsor's downtown features diverse dining options such as Dom’s for breakfast, Windsor Asian Bistro for Asian cuisine, and Union Street Tavern, a converted firehouse pub that hosts charity events. Residents enjoy various things to do, including summer concerts at the Town Green and Halloween festivities like Nightmare on Broad Street. Windsor Public Schools are highly rated, with John F. Kennedy School, Sage Park Middle School, Windsor High School, and Oliver Ellsworth School all earning commendable grades. Recreational opportunities abound with the Keney Park Golf Course and Windsor Meadows State Park offering outdoor activities. The city is well-connected with CT Transit bus lines, a local train station, and proximity to Bradley International Airport. Homes in Windsor range from historical properties to contemporary builds, often situated on spacious lots without sidewalks.

Home Trends in Windsor, CT

Housing Trends

Median Sale Price
$355,000
Median Single Family Sale Price
$367,265
Median Townhouse Sale Price
$350,000
Median 2 Bedroom Sale Price
$326,950
Median 1 Bedroom Sale Price
$105,000
Average Price Per Sq Ft
$230
Number of Homes for Sale
39
Last 12 months Home Sales
333
Months of Supply
1.40
Median List Price
$349,950
Median Change From 1st List Price
-3%
Median Home Sale Price YoY Change
4%
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