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Woodstock, CT Homes for Sale

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  • /31

    $999,000

    • 4 Beds
    • 3 Baths
    • 3,480 Sq Ft

    19 Hiawatha Heights, Woodstock Valley, CT 06282

    Price Improvement!!! RARE PRIVATE LAKEFRONT GEM: PICTURE WINDOWS FRAME PANORAMIC VIEWS & A COVETED SECLUDED FLAT LOT! Welcome to your sanctuary on Lake Bunggee in Woodstock, CT. This 3,480 sq ft fully renovated 4BR/3BA home offers unparalleled private living. Boasting 113 ft of direct, private lake frontage and a coveted flat lot for effortless water access. Expansive picture windows frame

    Agent Photo

    Kimberly Amundarain

    Executive Real Estate Inc.

    (860) 370-3421

    19 Hiawatha Heights, Woodstock Valley, CT 06282
  • /40

    $549,900 Open Sun 10AM - 11:30AM

    • 4 Beds
    • 2.5 Baths
    • 1,887 Sq Ft

    71 Rawson Rd, Woodstock, CT 06281

    Discover a timeless blend of history and modern comfort at 71 Rawson Road, a lovingly modernized 1800s Colonial-style farmhouse located off a serene country road in Woodstock, CT. This distinguished "gentleman's farm" encompasses 1,887 sq ft of living space with 4 well-appointed bedrooms and 2 1/2 baths-perfectly poised for today's lifestyle while retaining classical New England charm. Step

    Agent Photo

    James Duffer

    RISE REC

    (860) 787-8530

    71 Rawson Rd, Woodstock, CT 06281
  • /17

    $235,000

    • Land
    • 5.11 Acres
    • $45,988 per Acre

    00 Joy Rd, Woodstock, CT 06281

    "Life is a Joy on Joy Road" Nestled in the heart of Woodstock, CT, this stunning 5.11-acre building lot offers the perfect balance of peaceful seclusion and easy access to modern conveniences. Surrounded by lush woodlands and gently rolling terrain, this property provides an idyllic setting for your dream home, offering privacy, natural beauty, and a connection to nature. Despite its serene

    Agent Photo

    Elizabeth Scranton

    Kazantzis Real Estate, LLC

    (860) 846-4563

    00 Joy Rd, Woodstock, CT 06281
  • /37

    $420,000 Open Sun 1PM - 3PM

    • 4 Beds
    • 1.5 Baths
    • 1,412 Sq Ft

    47 Little Bungee Hill Rd, Woodstock Valley, CT 06282

    Welcome home to this charming 1,412 sq ft ranch just a stone's throw from sparkling Lake Bunggee! Inside, an airy open floor plan unites a sun-splashed living room with a stylish kitchen and dining area-granite counters, generous cabinetry, and sight-lines that make entertaining a breeze. Three comfortable bedrooms plus a flexible fourth (ideal for an office, playroom, or guest room) share 1 1/2

    Agent Photo

    Carol Ryniewicz

    CR Premier Properties

    (860) 846-7110

    47 Little Bungee Hill Rd, Woodstock Valley, CT 06282
  • /39

    $450,000 Open Sun 1PM - 3PM

    • 4 Beds
    • 1.5 Baths
    • 1,412 Sq Ft

    47 Little Bungee Hill Rd Unit A, Woodstock Valley, CT 06282

    Welcome home to this charming 1,412 sq ft ranch just a stone's throw from sparkling Lake Bunggee! Inside, an airy open floor plan unites a sun-splashed living room with a stylish kitchen and dining area-granite counters, generous cabinetry, and sight-lines that make entertaining a breeze. Three comfortable bedrooms plus a flexible fourth (ideal for an office, playroom, or guest room) share 1 1/2

    Agent Photo

    Carol Ryniewicz

    CR Premier Properties

    (860) 507-9745

    47 Little Bungee Hill Rd Unit A, Woodstock Valley, CT 06282
  • /11

    $925,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 3,500 Sq Ft

    0 Joy Rd, Woodstock, CT 06281

    Luxury Ranch-Style Home To Be Built by DHS Copeland Builders - Woodstock, Ct Offered on a Private 5-Acre Parcel - Bring Your Plans or Use Ours! Discover the perfect blend of elegance and tranquility with this to-be-built luxury ranch-style home by the renowned DHS Copeland Builders. Centrally located in the heart of Woodstock, CT, this rare 5-acre parcel offers the ideal canvas for your dream

    Agent Photo

    Elizabeth Scranton

    Kazantzis Real Estate, LLC

    (860) 813-2921

    0 Joy Rd, Woodstock, CT 06281
  • /18

    $895,000 New Construction

    • 4 Beds
    • 3.5 Baths
    • 2,925 Sq Ft

    36 Olde Meadow Rd, Woodstock, CT 06281

    TO BE CONSTRUCTED: Welcome to Eastwood Estates - Luxury Living in the Heart of Woodstock! Discover the elegance and tranquility of Eastwood Estates. If you're looking for privacy, this 1.92 acre lot borders open space with lovely stone walls. Modern Farmhouse home design is stunning with timeless curb appeal. Some exterior features: white clapboard siding, gabled dormers, and a welcoming covered

    Agent Photo

    Tina Lajoie

    William Raveis Real Estate

    (860) 407-5265

    36 Olde Meadow Rd, Woodstock, CT 06281
  • /40

    $659,900

    • 4 Beds
    • 3.5 Baths
    • 4,536 Sq Ft

    101 Center Rd, Woodstock, CT 06281

    This beautiful sprawling custom colonial is set on 9 acres of land at the end of a winding long driveway and surrounded by open area. Grand living spaces with cathedral ceilings and a floor to ceiling fireplace, tons of natural light, 4 bedrooms & 3.5 bathrooms, a 1500 sqft in-law suite with additional bedroom, new appliances, spacious 2 car garage, and an out building with electricity and

    Jeff Valentine William Pitt Sotheby's Int'l

    101 Center Rd, Woodstock, CT 06281
  • /40

    $719,900

    • 4 Beds
    • 5 Baths
    • 3,795 Sq Ft

    64 May Brook, Woodstock, CT 06281

    Welcome to 64 May Brook, a beautiful home set on a cul-de-sac in Woodstock with one of the healthiest lawns you'll find, complete with fruit trees, a playscape, and more. Step into the open foyer with a graceful turned staircase. To the right, a convenient first-floor suite awaits, while to the left a cozy den connects seamlessly to the formal dining room. The heart of the home is the kitchen,

    Jared Meehan RE/MAX Bell Park Realty

    64 May Brook, Woodstock, CT 06281
  • /27

    $875,000

    • 3 Beds
    • 2.5 Baths
    • 2,160 Sq Ft

    28 Lake View Dr, Woodstock, CT 06281

    The Lake Home That Truly Has It All. This is more than just a charming waterfront- it's the home that checks every box! Set on beautiful Lake Bunggee, this year-round 3-bedroom retreat pairs panoramic water views with irresistible curb appeal and a storybook sense of charm in one of the lake's most desirable locations. Cathedral ceilings flood the home with natural light, while the gourmet

    Jennie Kesselman Berkshire Hathaway NE Prop.

    28 Lake View Dr, Woodstock, CT 06281
  • /40

    $565,000

    • 5 Beds
    • 3.5 Baths
    • 4,172 Sq Ft

    4 Perrin Rd, Woodstock, CT 06281

    Welcome to the exquisite Ebenezer Stoddard house built in 1800 once an inn for travelers on an early state route. This 4100 sq ft home is filled with character, history and updates for modern convenience, while saving the historic charm! The home resides on an 1.2 acre lot, mostly cleared with plenty of room for family gatherings of any size! Entering the home into an official mudroom - leave

    Kerri Mullen CR Premier Properties

    4 Perrin Rd, Woodstock, CT 06281
  • /40

    $595,000

    • 4 Beds
    • 2 Baths
    • 2,160 Sq Ft

    23 Little Bungee Hill Rd, Woodstock Valley, CT 06282

    The pictures really tell the story with this one. Down a quiet road on a 1.22 acre lot within sight of Lake Bunggee, this 2160 sq ft, 4 Br, 2 Ba home has been rebuilt from the floor joists up. Rich with custom touches and all new electrical, plumbing, insulation, roofing, etc. Pull up the double wide driveway (paved in 2023) to a two car garage (575 sq ft, plus loft), where you'll never get

    Alan Berman Signature Properties of NewEng

    23 Little Bungee Hill Rd, Woodstock Valley, CT 06282
  • /40

    $659,999

    • 3 Beds
    • 3.5 Baths
    • 3,078 Sq Ft

    39 Grey Fox Landing, Woodstock, CT 06281

    This meticulously cared-for Colonial is nestled in a desirable neighborhood and offers the perfect blend of comfort and versatility. The spacious room above the garage has been beautifully finished, making it ideal for an in-law suite, guest space, or bonus room. The kitchen features granite countertops, stainless steel appliances(all approximately 5 years old), and flows seamlessly into the main

    Andrea Kazantzis, CCIM Kazantzis Real Estate, LLC

    39 Grey Fox Landing, Woodstock, CT 06281
  • /38

    $570,000

    • 4 Beds
    • 2.5 Baths
    • 2,016 Sq Ft

    104 Pulpit Rock Rd, Woodstock, CT 06281

    This is a MUST SEE, you will absolutely LOVE this 4 Bedroom 2.5 bath meticulously maintained Colonial style home! Offering a seamless blend of classic charm and modern comfort creating an inviting and functional living environment. High ceilings and abundant natural light illuminate the rich engineered wood floors and detailed crown molding throughout. Enjoy this beautiful kitchen featuring

    Belinda Culp Berkshire Hathaway NE Prop.

    104 Pulpit Rock Rd, Woodstock, CT 06281
  • /40

    $679,000

    • 3 Beds
    • 2 Baths
    • 2,669 Sq Ft

    402 Perrin Rd, Woodstock, CT 06281

    Welcome to this charming 2.7-acre property, where functionality meets potential. Perfectly suited for horse enthusiasts, this small yet mighty property provides endless possibilities-whether you're looking to house your own horses, run a boarding business, or provide training. The beautifully remodeled antique home exudes warmth and character, featuring a cozy living room with a wood stove, a

    Kelly Ryan William Raveis Real Estate

    402 Perrin Rd, Woodstock, CT 06281
  • /20

    $339,500 Open Sat 1PM - 4PM

    • 2 Beds
    • 2 Baths
    • 1,541 Sq Ft

    42 Woodstock Meadows Unit 42, Woodstock, CT 06281

    No more leaf-raking, mowing, gutter clean-outs or snowplowing for you! Experience the ease of the friendly Woodstock Meadows condo community within walking distance to Roseland Park & Golf course, and only ten minutes to Putnam shops and hospital. This is the "Cape" style, one level, south-facing end unit of a duplex, with two large bedrooms, two full baths. The primary bedroom has two large

    Derek Greene Derek Greene

    42 Woodstock Meadows Unit 42, Woodstock, CT 06281
  • /15

    $190,000

    • 2 Beds
    • 1 Bath
    • 888 Sq Ft

    9 Sherman Rd, Woodstock, CT 06281

    Investor Opportunity in Woodstock! Set on a corner lot on a quiet country road, this 2-bedroom ranch offers strong potential for renovation or redevelopment. The home features a classic layout with a spacious living room, fireplace, eat-in kitchen, and full bath. A detached red barn adds charm and versatility - ideal for workshop, horse paddock, storage, or possible conversion. The interior

    Ryan Braunagel Keller Williams Realty Prtnrs.

    9 Sherman Rd, Woodstock, CT 06281
  • /39

    $549,000

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

    101 Child Hill Rd, Woodstock, CT 06281

    Step back in time with this one-of-a-kind 1830 Greek Revival farmhouse, offering 2,150 sq ft of character and charm on a picturesque 0.90-acre lot surrounded by farm land. Just down the hill from historic Woodstock Hill and the Academy, this setting is as scenic as it is convenient. Inside, wide plank floors and distinctive windows frame beautiful country views, while the front entry showcases

    Kristen Kaskela Berkshire Hathaway NE Prop.

    101 Child Hill Rd, Woodstock, CT 06281
  • /40

    $525,000 Open Sun 12PM - 2PM

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

    31 Deer Meadow Ln, Woodstock, CT 06281

    Welcome to Deer Meadow - one of the area's most desirable cul-de-sac neighborhoods! This solid, classic Colonial sits in an open-space subdivision with a shared recreational area for everyone to enjoy. Inside, sunlight fills the inviting living room with hardwood floors and a cozy fireplace. The spacious eat-in kitchen features solid wood cabinetry, Corian counters, a center island, and sliders

    Mary Collins Berkshire Hathaway NE Prop.

    31 Deer Meadow Ln, Woodstock, CT 06281
  • /31

    $430,000

    • 3 Beds
    • 2.5 Baths
    • 1,560 Sq Ft

    15 Windswept Dr, Woodstock, CT 06281

    Welcome to this inviting 3-bedroom, 3-bathroom home nestled on a quiet cul-de-sac in Woodstock, CT. Bursting with curb appeal, this property blends comfort, character, and convenience. It's just 7 minutes to the Massachusetts border and 6 minutes to Bigelow Hollow State Park, offering the best of both privacy and easy access to nature and amenities. Inside, you'll find a welcoming layout with a

    Ashley Walker Brunet and Company Real Estate

    15 Windswept Dr, Woodstock, CT 06281
  • /3

    $149,900

    • Land
    • 3.96 Acres
    • $37,854 per Acre

    0 Connecticut 169, Woodstock, CT 06281

    This parcel features over 700 feet of road frontage on Route 169. Slopes from road and flattens as you approach Bentley Sport Complex to the rear. Will need to perc test. Woodstock Hill location across from The Inn at Woodstock Hill. Nice view.

    Richard Loomis RE/MAX Bell Park Realty

    0 Connecticut 169, Woodstock, CT 06281
  • /31

    $448,500

    • 4 Beds
    • 1.5 Baths
    • 1,904 Sq Ft

    381 Bungay Hill Rd, Woodstock, CT 06281

    Situated in tranquil Woodstock, this spacious four bedroom Cape is the ultimate hidden treasure. It's calm, tree-lined 4.23 acres opens up to offer a large yard to allow space for all of your outdoor activities. Inside, you will be met with a smooth-flowing layout, 9ft ceilings, and plenty of natural lighting. The first level homes two sizeable bedrooms that transition into the main living space

    Anna Marsh BHHS Realty Professionals

    381 Bungay Hill Rd, Woodstock, CT 06281
  • /21

    $71,000

    • 2 Beds
    • 1 Bath
    • 775 Sq Ft

    6 Meadowside Rd, Woodstock, CT 06281

    Welcome to beautiful Meadowside of Woodstock, CT Campground, your home away from home! This is a rare opportunity to own your very own campsite along with this 1986 Regal Prowler 34 Model with a custom additional living room/bedroom space that has been added on. Enjoy peace and serenity with this spacious lot bordering the Thompson town line with a beautiful stone wall. Lots of work has been done

    Diane White CR Premier Properties

    6 Meadowside Rd, Woodstock, CT 06281
  • /35

    $375,000

    • 3 Beds
    • 2 Baths
    • 1,536 Sq Ft

    328 County Rd, Woodstock, CT 06281

    Charming Farmhouse located on a picturesque 1.2 acre corner lot in Woodstock CT! This 3 bedroom, 2 bath home blends historic charm with modern comfort. Featuring hardwood floors throughout, a spacious living room with cozy fireplace, and a large dining room perfect for gatherings. The cozy kitchen opens to a low-maintenance Trex deck, which is ideal for relaxing or entertaining while enjoying

    Shiloh Therrien The Neighborhood Realty Group

    328 County Rd, Woodstock, CT 06281
  • /18

    $450,000

    • 4 Beds
    • 1 Bath
    • 1,144 Sq Ft

    285 E Quasset Rd, Woodstock, CT 06281

    Discover the charm of lakeside living on peaceful Quasset Lake in Woodstock, CT. This cozy 4-bedroom, 1-bathroom cottage offers the perfect blend of comfort and country serenity. Set on a 0.84-acre lot with apx. 150 feet of private shoreline, it's an ideal retreat for boating, fishing, or simply enjoying peaceful waterfront views. The finished walk-out lower level extends the living space, making

    Jason Saphire www.HomeZu.com

    285 E Quasset Rd, Woodstock, CT 06281
  • /7

    $85,000

    • Land
    • 0.88 Acre
    • $96,591 per Acre

    0 Aplin Hill Ln, Woodstock, CT 06282

    The perfect blend of privacy and community. Lot 4 is the only rear lot in this quiet Woodstock Valley cul-de-sac, a rare chance to build in a growing neighborhood while enjoying the privacy of a wooded .88-acre setting. Conservation land borders the northern and eastern edges, creating a natural buffer that sets this lot apart from the rest. With construction now underway on neighboring Lots 3, 5

    Kristen Kaskela Berkshire Hathaway NE Prop.

    0 Aplin Hill Ln, Woodstock, CT 06282
  • /39

    $524,900

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

    36 Dunleavy Dr, Woodstock, CT 06281

    Discover this charming colonial Lakefront home on Roseland Lake, offering 2,036 sq ft of lovely updated living space. Boasting 3 to 4 bedrooms and 2 full baths, this residence combines classic elegance with modern comforts. The home features a spacious 2 1/2 car garage, an oversized shed for ample storage, and was renovated and expanded in 2017, ensuring contemporary finishes and functional

    Diane White CR Premier Properties

    36 Dunleavy Dr, Woodstock, CT 06281
  • /37

    $549,900

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

    1 Laurel Hill Dr, Woodstock Valley, CT 06282

    Pride of ownership shines in this wonderful year-round ranch nestled in a peaceful cove on fully recreational Lake Bungee!Whether you're looking to fish,swim,kayak,ski,or ice fish this home offers four seasons of fun right from your backyard-complete with your own private dock and stunning view of the nearby waterfall! Thoughtfully updated in 2025 the entire house was given a fresh new look!

    Pat Malek First Choice Realty

    1 Laurel Hill Dr, Woodstock Valley, CT 06282
  • /40

    $1,100,000

    • 5 Beds
    • 4 Baths
    • 5,079 Sq Ft

    76 Mill Brook Ln, Woodstock, CT 06281

    Tucked away on 6.5 private acres in the prestigious MillBrook Estates, this 5,000+ sq ft custom home offers an exceptional blend of elegance, functionality, and luxury. A long paved drive leads to this stately residence, featuring 5 bedrooms, multiple living areas, and rich architectural details throughout. The grand foyer with a hydraulic chandelier sets the tone for the craftsmanship found

    Katie Totten William Raveis Real Estate

    76 Mill Brook Ln, Woodstock, CT 06281
  • /29

    $449,900

    • 3 Beds
    • 2.5 Baths
    • 1,682 Sq Ft

    70 Laurel Hill Dr, Woodstock Valley, CT 06282

    Get ready to fall in love with this fully renovated colonial, just one minute from the beach and offering stunning water views! What was once a charming 1,200 sq ft Cape has been recently completely reimagined into a spacious 1,600 sq ft Colonial. This like-new home now boasts 3 bedrooms, 2.5 bathrooms, and a fresh, modern layout perfect for everyday living and entertaining. The heart of the home

    Katelyn Battista Real Broker CT, LLC

    70 Laurel Hill Dr, Woodstock Valley, CT 06282
  • /39

    $1,250,000

    • 2 Beds
    • 2 Baths
    • 2,340 Sq Ft

    1669 Route 169, Woodstock, CT 06281

    Welcome to Hilltop Meadows-a one-of-a-kind, 60-acre luxury hay farm nestled in Connecticut's scenic "Quiet Corner." Set high above Route 169 in North Woodstock, this breathtaking property offers rolling meadows, mature forests, and serene privacy just 60 miles from Boston and 150 from Manhattan. The heart of the property is a newly updated 2-bed, 2-bath, 2,340 sq ft farmhouse blending historic

    Ryan De Lello William Pitt Sotheby's Internatiomal Realty

    1669 Route 169, Woodstock, CT 06281
  • /39

    $1,836,000

    • 4 Beds
    • 3.5 Baths
    • 5,104 Sq Ft

    175 Pulpit Rock Rd, Woodstock, CT 06281

    A once-in-a-generation opportunity. Please visit this stunning Georgian estate situated on 55 hilltop acres in desirable Woodstock, CT. Enjoy breathtaking long views all the way to Rhode Island! A few of the exceptional assets offered include an elegant in-law apartment, a large 6 stall horse barn with office, an inviting in-ground pool, and 25 acres of fenced open pasture. As you approach the

    John Downs Berkshire Hathaway NE Prop.

    175 Pulpit Rock Rd, Woodstock, CT 06281
  • /32

    $475,000

    • 3 Beds
    • 1.5 Baths
    • 1,008 Sq Ft

    56 Laurel Hill Dr, Woodstock Valley, CT 06282

    Charming 3-Bedroom Home on Double Lot - Lake Bunggee Waterfront Access! Discover the potential of this charming 3-bedroom home nestled in the heart of Connecticut's Quiet Corner, just steps from beautiful Lake Bunggee. Set on a spacious double lot, this property is waiting for your personal touches-bring your tools and imagination to make it your own! Enjoy lake life year-round with a walk-out

    Vivian Kozey CR Premier Properties

    56 Laurel Hill Dr, Woodstock Valley, CT 06282
  • /2

    $99,900

    • Land
    • 12 Acres
    • $8,325 per Acre

    00 Prospect St, Woodstock, CT 06281

    Discover the perfect canvas for your dream home or private retreat on this stunning 12-acre parcel located in scenic Woodstock, Connecticut. This unique piece of land offers a peaceful setting with a blend of rolling topography, mature trees, and a beautiful pond-ideal for nature lovers, homesteaders, or anyone seeking privacy and serenity. The land features varied elevations, providing

    Mateusz Chojnicki CR Premier Properties

    00 Prospect St, Woodstock, CT 06281
  • /2

    $260,000 Open House 10/04

    • 1 Bed
    • 1 Bath
    • 1,536 Sq Ft

    17 Woodstock Meadows, Woodstock, CT 06281

    **Professional Photos Coming Soon. Location is everything! Welcome to 17 Woodstock Meadows, a beautifully updated condominium in the heart of Woodstock, Connecticut, set in one of the town's most desirable neighborhoods. Just a short stroll away, you'll find historic Roseland Park and Golf Course, where wooded trails, open fields, and recreational opportunities are waiting to be enjoyed. Rarely

    Tracie Gagnon Berkshire Hathaway NE Prop.

    17 Woodstock Meadows, Woodstock, CT 06281

Why Live in Woodstock

When successful New York businessman Henry Bowen built a pink summer home in the countryside of Woodstock, he started a trend that continues in the Connecticut town today. Transplants and visitors from across the Northeast, particularly New York, ...

Frequently Asked Questions

What is the average home price in Woodstock, CT?
Homes for sale in Woodstock, CT have an average home price of $577,572.
How many homes have sold over the last 12 months in Woodstock, CT?
91 homes have sold in Woodstock, CT over the last 12 months.
What are the most popular zip codes in Woodstock, CT?
The most popular zip codes in Woodstock, CT include 06281, 06282, 01550, 06255 and 01571.
How much do you need to make to afford a house in Woodstock?
The median home price in Woodstock is $549,000. If you put a 20% down payment of $109,800 and had a 30-year fixed mortgage with an interest rate of 6.26%, your estimated principal and interest payment would be $2,710 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $116K a year to afford the median home price in Woodstock.
How are the schools in Woodstock, CT?
Woodstock, CT has highly rated public and private schools. Some of the best schools in Woodstock based on Niche Grades are Tantasqua Regional High School, The Woodstock Academy and Union Elementary School. Browse all the schools in Woodstock, CT to learn more.

Home Trends in Woodstock, CT

Housing Trends

Median Sale Price
$475,000
Median Single Family Sale Price
$539,500
Median Townhouse Sale Price
$299,166
Median 1 Bedroom Sale Price
$260,000
Average Price Per Sq Ft
$271
Number of Homes for Sale
23
Last 12 months Home Sales
91
Months of Supply
3.00
Median List Price
$549,000
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
13%
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