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Homes for Sale in 05091

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  • /54

    $2,599,000

    • 9 Beds
    • 11 Baths
    • 5,993 Sq Ft

    41 Pleasant St, Woodstock, VT 05091

    This exquisite Victorian invites you to embracequintessential New England living in a charming downtown setting. This property in Woodstock, VT offers a rare blend of historic charm and modern convenience, all within one of Vermont’s most beloved communities. Woodstock is often hailed as “the prettiest small town in America,” and for good reason. The village is a vibrant resort town with

    Agent Photo

    Jennifer Falvey

    KW Vermont Woodstock

    (802) 347-9544

    41 Pleasant St, Woodstock, VT 05091
  • /14

    $158,000

    • Land
    • 16.5 Acres
    • $9,576 per Acre

    000 Chateauguay Rd, Barnard, VT 05031

    Discover a rare opportunity to own a 16.5-acre land parcel nestled in the heart of Barnard, Vermont. This idyllic property features a perfect blend of cleared and wooded areas, providing endless possibilities for your dream home or retreat. Situated on a quiet, town-maintained road, this parcel offers both privacy and accessibility. Imagine waking up to serene pastoral views, surrounded by the

    Agent Photo

    Susan Hickey

    Snyder Donegan Real Estate Group

    (802) 471-2770

    000 Chateauguay Rd, Barnard, VT 05031
  • /31

    $1,195,000 Open Sun 1PM - 3PM

    • 3 Beds
    • 3.5 Baths
    • 2,385 Sq Ft

    26 Mount Peg Rd Unit D, Woodstock, VT 05091

    Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a prime location that offers ease of access to and year-round enjoyment of a plentitude of options for recreating, dining, shopping, theatre, and the arts. A light-filled main level interior with white oak flooring sets the stage

    Mary Mayhew Snyder Donegan Real Estate Group

    26 Mount Peg Rd Unit D, Woodstock, VT 05091
  • /32

    $1,195,000 Open Sun 1PM - 3PM

    • 3 Beds
    • 3.5 Baths
    • 2,592 Sq Ft

    26 Mount Peg Rd Unit A, Woodstock, VT 05091

    Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a prime location that offers ease of access to and year-round enjoyment of a plentitude of options for recreating, dining, shopping, theatre, and the arts. A light-filled main level interior with white oak flooring sets the stage

    Mary Mayhew Snyder Donegan Real Estate Group

    26 Mount Peg Rd Unit A, Woodstock, VT 05091
  • /31

    $995,000 Open Sun 1PM - 3PM

    • 3 Beds
    • 3.5 Baths
    • 2,584 Sq Ft

    26 Mount Peg Rd Unit B, Woodstock, VT 05091

    Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a prime location that offers ease of access to and year-round enjoyment of a plentitude of options for recreating, dining, shopping, theatre, and the arts. A light-filled main level interior with white oak flooring sets the stage

    Mary Mayhew Snyder Donegan Real Estate Group

    26 Mount Peg Rd Unit B, Woodstock, VT 05091
  • /38

    $795,000

    • 4 Beds
    • 3 Baths
    • 2,099 Sq Ft

    6077 Vt Route 12, Barnard, VT 05031

    BARNARD VILLAGE CAPE- This elegant Cape sits in an ideal location in the idyllic village of Barnard, just a short walk to the Barnard General Store and Silver Lake. The perfect blend of original charm, sophistication, and modern amenities, the house is bright and welcoming with lovely natural woodwork and plenty of space for social gatherings or quiet privacy. A large central living room features

    David Donegan Snyder Donegan Real Estate Group

    6077 Vt Route 12, Barnard, VT 05031
  • /28

    $995,000 Open Sun 1PM - 3PM

    • 3 Beds
    • 3.5 Baths
    • 2,584 Sq Ft

    26 Mount Peg Rd Unit C, Woodstock, VT 05091

    Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a prime location that offers ease of access to and year-round enjoyment of a plentitude of options for recreating, dining, shopping, theatre, and the arts. A light-filled main level interior with white oak flooring sets the stage

    Mary Mayhew Snyder Donegan Real Estate Group

    26 Mount Peg Rd Unit C, Woodstock, VT 05091
  • /49

    $1,595,000

    • 5 Beds
    • 3.5 Baths
    • 3,648 Sq Ft

    1522 Barnard Rd, Woodstock, VT 05091

    Just 2 miles from Woodstock Village, this gracious brick cape on 6 open acres offers space, comfort, and classic Vermont charm. The expanded chef’s kitchen opens to a gracious gathering room ideal for entertaining, while 3 fireplaces—wood-burning, brick, and gas-ready—provide cozy warmth throughout. Upstairs, find 3–4 bedrooms including one with its own fireplace, plus a private guest room or

    Keri Cole Williamson Group Sothebys Intl. Realty

    1522 Barnard Rd, Woodstock, VT 05091
  • /41

    $1,495,000

    • 4 Beds
    • 2.5 Baths
    • 2,532 Sq Ft

    7 Slayton Terrace, Woodstock, VT 05091

    A rare in-village offering, 7 Slayton Terrace combines walkability, views, and beautifully renovated interiors—just steps from the heart of Woodstock. Sited on an oversized .79-acre lot overlooking Billings Farm, this 4-bedroom home offers the space and flexibility rarely found so close to the village center. The main house features a stunning new kitchen with high-end finishes and beautifully

    Keri Cole Williamson Group Sothebys Intl. Realty

    7 Slayton Terrace, Woodstock, VT 05091
  • /43

    $1,600,000

    • 4 Beds
    • 3 Baths
    • 6,014 Sq Ft

    15 Central St, Woodstock, VT 05091

    15 Central Street is one of the finest commercial locations in Woodstock with two of the most creative and successful businesses as the anchor tenants. The property has adapted to changes of the course of its long history of uses including residential shop owner, a barber shop, a dance & pool hall, law office, architectural services and a variety of mercantile endeavors. Notably, the building

    Laird Bradley Williamson Group Sothebys Intl. Realty

    15 Central St, Woodstock, VT 05091
  • /60

    $2,395,000

    • 6 Beds
    • 5 Baths
    • 3,645 Sq Ft

    1362 Barnard Rd, Woodstock, VT 05091

    Gilbert’s Hill, the very best of Vermont living - Iconic, 112-acre estate with a storybook history as the first “modern” ski run in the US. Located two miles from the village center of Woodstock, the “prettiest small town in America", experience rural peace with convenient access to great restaurants and shops. Turnkey, fully-restored Vermont farmstead - a picturesque family compound with 7

    Chris Lang

    1362 Barnard Rd, Woodstock, VT 05091
  • /60

    $1,300,000

    • 4 Beds
    • 5 Baths
    • 3,195 Sq Ft

    125 Shurtleff Ln, Woodstock, VT 05091

    Beautifully sited just a short walk from Woodstock Village, this 2015 custom-built home blends modern comfort with timeless Vermont charm. Thoughtfully designed for everyday living and entertaining, the main level features an open, light-filled layout, a well-appointed kitchen, and seamless access to a sunny three-season room overlooking the landscaped grounds. The sought-after first-floor

    Keri Cole Williamson Group Sothebys Intl. Realty

    125 Shurtleff Ln, Woodstock, VT 05091
  • /45

    $1,450,000

    • 8 Beds
    • 5 Baths
    • 3,814 Sq Ft

    7030 U S 4, Bridgewater, VT 05034

    Situated between historic Woodstock Vermont and the ski slopes of Killington, 7030 US Route 4 provides easy access to the best amenities of the area. The Property has two separate spaces, a standalone two-level garage with ample storage area below, and sits on 6 acres with direct river access. The "Apartment” first floor has an open design with a kitchen, living area, and tucked away bathroom.

    Eric Benvenuti

    7030 U S 4, Bridgewater, VT 05034
  • /47

    $8,000,000

    • 3 Beds
    • 3.5 Baths
    • 5,384 Sq Ft

    115 Eastman Rd, Woodstock, VT 05091

    Sorgenfrei, or "Carefree," was built by Ennis Construction in 2015, and this extraordinary property truly embodies that sobriquet. A stunning and uncommon confluence of the finest materials and the most energy efficient techniques, this home was carefully constructed to maximize worry-free enjoyment. The most advanced systems and a focused commitment to the highest quality make this home a

    Keri Cole Williamson Group Sothebys Intl. Realty

    115 Eastman Rd, Woodstock, VT 05091
  • /11

    $190,000

    • 2 Beds
    • 1.5 Baths
    • 1,200 Sq Ft

    99 Safford Commons Way, Woodstock, VT 05091

    These 1200 sq. ft., 2-bedroom, 1.5-bathroom condos are being sold for less than half of their fair market value! Available for immediate move-in, each condo has an open-concept kitchen, dining room, and living room, which are on the airy and light-filled second floor. There is a small deck off the living room. The two cozy bedrooms are on the first floor. Electricity bills will be offset by solar

    Jane Darrach Martha E. Diebold/Hanover

    99 Safford Commons Way, Woodstock, VT 05091
  • /3

    $215,000

    • Land
    • 64 Acres
    • $3,359 per Acre

    251 Garvin Hill Rd, Hartland, VT 05048

    64 acres of land in Hartland, Vermont featuring a small pond and a peaceful country setting. This property offers plenty of space for building, recreation, farming, or enjoying the outdoors. A great opportunity to own a large parcel with privacy and natural beauty. The sale of this property being listed is contingent upon the proposed Seller (or "Owner") completing his/her/its purchase of this

    Derek Greene Derek Greene

    251 Garvin Hill Rd, Hartland, VT 05048
  • /11

    $779,000

    • Land
    • 6.46 Acres
    • $120,588 per Acre

    0 Barnard Rd Unit 20.002, Woodstock, VT 05091

    A truly unique 6 acre parcel of land conveniently located in the heart of Woodstock! Tremendous development potential! Zoning allows both COMMERCIAL and RESIDENTIAL use! The 6 acres visually divide into 2 components with 2 diverse personalities. The 1st component is an extraordinary private building lot in the heart of Woodstock! Access to this 4 acre component initially leads through a pleasant

    John Wetmore Wetmore Real Estate

    0 Barnard Rd Unit 20.002, Woodstock, VT 05091
  • /17

    $825,000

    • Land
    • 150 Acres
    • $5,500 per Acre

    0 Walker Hill Rd Unit 5039522, Bridgewater, VT 05091

    150 acres of recreational paradise! Absolute and total privacy! Enjoy long views of mountain peaks showing criss crossed ski trails, pristine cascading streams with mesmerizing waterfalls over large rock outcroppings, mature woodland which hasn't been logged in over 50 years, a fully equipped camper trailer with propane fired generator for off grid living and even a 4 wheeler outfitted with

    John Wetmore Wetmore Real Estate

    0 Walker Hill Rd Unit 5039522, Bridgewater, VT 05091
  • /45

    $725,000

    • 5 Beds
    • 3 Baths
    • 3,028 Sq Ft

    137 Laughlin Rd, Woodstock, VT 05091

    Charming property located just minutes from historic Woodstock Green. The main house first floor features 3 bedrooms/ 1bath with formal dining room, living room and kitchen on first level anchored by an expansive deck for entertaining or enjoying the afternoon sun. Handsome hardwood floors throughout, stainless appliances in the kitchen accented with granite countertops. The lower level is walk

    Gretchjen Smith Williamson Group Sothebys Intl. Realty

    137 Laughlin Rd, Woodstock, VT 05091
  • /60

    $825,000

    • 5 Beds
    • 5 Baths
    • 3,886 Sq Ft

    3961 Hartland Hill Rd, Woodstock, VT 05091

    NEW PRICE! This lovely,expanded Cape sits just a half mile from Woodstock Village's East End.Surrounded by rolling green fields and wooded hillsides-this home offers a beautiful country setting less than a mile to village shopping, schools, dining and recreation. Updated with modern finishes to enhance accessibility and one level living-while maintaining the warm, country charm. First floor

    Tambrey Vutech KW Vermont Woodstock

    3961 Hartland Hill Rd, Woodstock, VT 05091
  • /33

    $3,945,000

    • 5 Beds
    • 5.5 Baths
    • 8,122 Sq Ft

    5685 Vermont 12, Barnard, VT 05031

    If you’ve been looking for the iconic Vermont home, rarely does an opportunity like this present itself. Welcome to HIGHLAND GLEN, an idyllic Vermont home situated on 12 picturesque acres in the quaint town of Barnard, VT. Upon arrival at Highland Glen, you'll immediately sense the special charm of this property, from the red barn to the mature apple orchard and sugar maples - your eyes will be

    John Snyder Snyder Donegan Real Estate Group

    5685 Vermont 12, Barnard, VT 05031
  • /55

    $915,000

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

    509 Church Hill Rd, Wood Stock, VT 05091

    Enjoy in-town ease of living combined with Vermont country charm. This well maintained , efficient home provides first floor living with an additional lower floor ensuite bedroom /sitting area with direct access to lovely grounds and gardens.The light filled home is in excellent condition and is surrounded by fabulous perennial gardens, mature maple trees, raspberry and blueberry bushes ,

    Carol Wood Williamson Group Sothebys Intl. Realty

    509 Church Hill Rd, Wood Stock, VT 05091
  • /37

    $419,000

    • 3 Beds
    • 2 Baths
    • 1,288 Sq Ft

    31 Lakota Rd, Barnard, VT 05031

    Once home to the renowned New England ski trail designer and craftsman, Robert L. Pearsons, this fully renovated 3 bedroom, 2 bathroom gem is located midway between the villages of Woodstock and Barnard with less than a 10 minute drive to each. The home is situated on 2 level acres of land with the Gulf stream (aka Lakota Brook) running along the edge, providing a magical spot for cooling off in

    Zoe Hathorn Washburn Snyder Donegan Real Estate Group

    31 Lakota Rd, Barnard, VT 05031
  • /35

    $495,000

    • 4 Beds
    • 3 Baths
    • 2,470 Sq Ft

    3364 W Woodstock Rd, Woodstock, VT 05091

    Welcome to this lovingly updated antique Cape, set on two open, level acres across from the sparkling Ottauquechee River. Just five minutes from Woodstock Village and perfectly positioned on the west side for quick trips to Killington and Pico, this home makes the ideal Vermont getaway. Inside, you’ll find four comfortable bedrooms and a warm, inviting layout designed for making memories. Gather

    Keri Cole Williamson Group Sothebys Intl. Realty

    3364 W Woodstock Rd, Woodstock, VT 05091
  • /9

    $275,000

    • Land
    • 0.43 Acre
    • $639,535 per Acre

    1054 W Woodstock Rd, Woodstock, VT 05091

    Ideally located parcel across West Woodstock Road from the Woodstock Farmers Market and 500 yards from the entry to Woodstock Union Middle & High School. Public water and sewer available with access off Prosper Road near the junction of US Road Route 4/West Woodstock Road. Building plans available. Multi-unit housing development potential in zero vacancy environment.

    Laird Bradley Williamson Group Sothebys Intl. Realty

    1054 W Woodstock Rd, Woodstock, VT 05091
  • /40

    $725,000

    • 4 Beds
    • 3 Baths
    • 3,584 Sq Ft

    3914 South Rd, Woodstock, VT 05091

    This South Woodstock contemporary residence was designed by the original architect-owner to showcase Vermont’s changing seasons and capture views of the Kedron Brook as it wanders through the property past small meadows tucked in along the banks. The home can be accessed privately at grade level through the heated garage and mudroom, while guests enter via a covered entry to the upper level. The

    Laird Bradley Williamson Group Sothebys Intl. Realty

    3914 South Rd, Woodstock, VT 05091
  • /18

    $275,000

    • 2 Beds
    • 1 Bath
    • 720 Sq Ft

    3186 South Rd, Woodstock, VT 05091

    Great location minutes from Woodstock Village, South Woodstock, and Green Mountain Horse Association. Kidder Brook runs along the North property boundary, and a sunny lawn area has multiple small gardens. The home is a well-cared for 1973 mobile home on a concrete slab, and there is a two-car detached garage which can be used for vehicles or a shop space. This approximately 1.95 acre lot has

    Andrew Hubbell Vermont Real Estate Company

    3186 South Rd, Woodstock, VT 05091
  • /11

    $190,000

    • 2 Beds
    • 1.5 Baths
    • 1,200 Sq Ft

    111 Safford Commons Way, Woodstock, VT 05091

    These 1200 sq. ft., 2-bedroom, 1.5-bathroom condos are being sold for less than half of their fair market value! Available for immediate move-in, each condo has an open-concept kitchen, dining room, and living room, which are on the airy and light-filled second floor. There is a small deck off the living room. The two cozy bedrooms are on the first floor. Electricity bills will be offset by solar

    Jane Darrach Martha E. Diebold/Hanover

    111 Safford Commons Way, Woodstock, VT 05091
  • /42

    $425,000

    • 2 Beds
    • 2 Baths
    • 1,440 Sq Ft

    1079 Fletcher Hill Rd, Woodstock, VT 05071

    This charming 2-bedroom ranch house offers a nice layout for main floor living. Features include a sunroom entrance, two bedrooms, a full bath, laundry room, and a main living/dining area with a kitchen, all within a rural setting with ample natural light, local views, and a deck. Recent updates include a primary bedroom ensuite featuring a custom walk-in shower and double sinks, new flooring, a

    Terry Davis Williamson Group Sothebys Intl. Realty

    1079 Fletcher Hill Rd, Woodstock, VT 05071
  • /42

    $3,500,000

    • 6 Beds
    • 8 Baths
    • 5,142 Sq Ft

    18 The Green, Woodstock, VT 05091

    Conveniently located on the southwest side of the picturesque Woodstock Village Green, this classic c1840 Greek Revival farmhouse is one of the town’s finest residences. Lovingly stewarded and thoughtfully restored to the highest standard preserving the historic integrity and honoring the period detail, all while achieving the perfect unification of sophistication, functionality, modern comfort

    Danny Kogut Williamson Group Sothebys Intl. Realty

    18 The Green, Woodstock, VT 05091
  • /7

    $54,900

    • Land
    • 29 Acres
    • $1,893 per Acre

    0 Rt 7 (Db 94 Dp 399), Royalton, KY 41464

    These 29 acres, per PVA map, are located in southern Magoffin County in Royalton, Kentucky, with the acreage running along both sides of RT 7. The property is located in the Salt Lick area outside Royalton and includes property on both sides of Salt Lick Road as well. The property is undeveloped but electric and public water are available. For those with visions of homesteading, the Licking River

    Doug Wireman First Choice Realty & Assoc.

    0 Rt 7 (Db 94 Dp 399), Royalton, KY 41464
  • /60

    $950,000

    • 3 Beds
    • 3 Baths
    • 2,794 Sq Ft

    34 Midsomer Meadows Ln, Woodstock, VT 05091

    Welcome to Starry Hill, a fully furnished and somewhat recent Airbnb rental. Handcrafted, solid-timber Colonial privately nestled on 18.9 tranquil acres just 5 miles North of Woodstock, built over 4 years by a family of loggers and master craftsmen. This exceptional home features Eastern white pine walls, hemlock structural beams, and pine ceilings/flooring sourced from the property. Warm,

    John Bassette Bassette Real Estate Group

    34 Midsomer Meadows Ln, Woodstock, VT 05091
  • /40

    $665,000

    • 3 Beds
    • 3 Baths
    • 2,659 Sq Ft

    2504 Vermont 12, Barnard, VT 05031

    Inspired by the organic architecture of Frank Lloyd Wright, this contemporary gem sits on 14.2 surveyed wooded acres. It feels private yet is less than 10 minutes to Woodstock. The interior has a warm, open floor plan rich with wood character and natural light. Recent upgrades include renovated bathrooms, highlighted by a newly added third bath as an ensuite from the primary bedroom featuring a

    Holly Hall Hall Collins Real Estate Group

    2504 Vermont 12, Barnard, VT 05031
  • /26

    $3,300,000

    • 3 Beds
    • 4.5 Baths
    • 3,682 Sq Ft

    249 Sawyer Rd, Woodstock, VT 05091

    Located in Woodstock, Vermont just one mile from the village green, the Alta House offers a rich quality of life filled with poolside sunsets, mountain vistas, proximity to town, and access to endless outdoor recreation opportunities. Enjoy the convenience of living close to the shops, cafes, and restaurants of Woodstock, while being tucked away in your own world above. The 3-bedroom primary

    Andrew Bustin LandVest, Inc/Woodstock

    249 Sawyer Rd, Woodstock, VT 05091
  • /7

    $325,000

    • Land
    • 8 Acres
    • $40,625 per Acre

    1 Carlton Hill Rd, Woodstock, VT 05091

    Sweet Spot - 8 acre building lot located within minutes of the Woodstock Village Green! Driveway is in place and a lovely building site has been cleared and power is at site. Wonderful opportunity to build your Vermont getaway or primary residence. Enjoy access to four season recreation, Marsh-Billings-Rockefeller National Park, theatre, arts, dining, shopping and a short commute to all

    Mary Mayhew Snyder Donegan Real Estate Group

    1 Carlton Hill Rd, Woodstock, VT 05091
  • /14

    $845,000

    • 2 Beds
    • 1 Bath
    • 600 Sq Ft

    234 Randall Rd, Wood Stock, VT 05091

    Randall Road Farm represents a rare opportunity to purchase a multigenerational family farmstead in an exceptionally desirable location. Long recognized as a well established farm raising Charolais beef cattle, poultry and hay. The owner has been the farmer/steward of many of the areas farms in the Woodstock and South Woodstock. The property has a single family dwelling, shop building with farm

    Wade Treadway Wade I Treadway Real Estate

    234 Randall Rd, Wood Stock, VT 05091
  • /48

    $6,750,000 New Construction

    • 4 Beds
    • 4.5 Baths
    • 5,087 Sq Ft

    412 Skyland Ln, Woodstock, VT 05091

    Once the site of an 1850s homestead and now reimagined for 21st-century living, Skyland Farm is a private retreat on 65 acres. Mineral springs, glass architecture, and extraordinary views define this rare legacy property, just minutes from the village of Woodstock and with direct access to the trails of Mount Peg. Found at the end of a quiet lane, sweeping vistas of the Green Mountains and

    Story Jenks LandVest, Inc/Woodstock

    412 Skyland Ln, Woodstock, VT 05091
  • /37

    $985,000

    • 4 Beds
    • 3 Baths
    • 2,785 Sq Ft

    1782 Randall Rd, Woodstock, VT 05091

    This early Woodstock residence was built in 1792 by Joseph Wood on a parcel of land he purchased in 1786 from Ebenezer Kingsley, one of Woodstock early settlers. A classic New England Cape of the period with the notable features of a central chimney with multiple fireplaces and a second story overhang on the gables. The house retains a great deal of original features and fabric including wide

    Wade Treadway Wade I Treadway Real Estate

    1782 Randall Rd, Woodstock, VT 05091
  • /52

    $439,000

    • 4 Beds
    • 2 Baths
    • 1,617 Sq Ft

    5798 W Woodstock Rd, Woodstock, VT 05091

    Charming 4 bedroom farmhouse with attached barn/garage with lots of overhead storage is located across the road from the scenic Ottauquechee River. Minutes from Woodstock Village Green with all of its amenities and a short distance from Killington with its world renown Ski Resort. Year round activities abound ! The house has a sunny eat in kitchen, spacious dining room and a living room complete

    Carol Wood Williamson Group Sothebys Intl. Realty

    5798 W Woodstock Rd, Woodstock, VT 05091
  • /60

    $799,000

    • 7 Beds
    • 7 Baths
    • 4,581 Sq Ft

    7137 US Route 4, Bridgewater, VT 05034

    Welcome to the historic Bridgewater Inn — a rare, turn-key Vermont property perfectly positioned between Woodstock Village, Killington Resort, and Okemo Mountain. This unique offering features a spacious 3-bedroom, 3-bath main home along with four fully equipped guest suites, creating exceptional flexibility for full-time living, multi-generational use, or continued short-term rental success. The

    Benjamin Cote EXP Realty

    7137 US Route 4, Bridgewater, VT 05034

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