Windsor County VT Homes for Sale with Acreage

• 

  

  

  /13

  $399,900

  • Land
  • 108 Acres
  • $3,703 per Acre

  1928 Vermont 131, Ascutney, VT 05030

  This 108 Acres +/- boasts one of the most beautiful and plentiful sugarbush in the state, that can easily accommodate over 4500 sugar taps. Matured stately maple timber with enough cord word available for a lifetime. Well maintained wood trails traverse the acreage. Several building sites with spectacular Mt. Ascutney views with clearing. This secluded hillside is just 5 minutes to Exit 8, 30

  Don Chabot Town and Country Realty

  1928 Vermont 131, Ascutney, VT 05030
• 

  

  

  /21

  $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
• 

  

  

  /9

  $300,000

  • Land
  • 9.8 Acres
  • $30,612 per Acre

  00 Stagecoach Rd, Norwich, VT 05055

  Discover peace and privacy on this 9-acre wooded lot situated near the end of a quiet private road. This natural haven offers excellent seclusion while remaining just 10 minutes from town amenities. With a mix of hardwood and softwood, the property features a significant stand of hemlock and oak —potentially providing enough timber to build your own custom timber-frame home right from the

  Linda White EXP Realty

  00 Stagecoach Rd, Norwich, VT 05055
• 

  

  

  /22

  $140,000

  • Land
  • 12.9 Acres
  • $10,853 per Acre

  0 Woods Rd W Unit 5081865, Ludlow, VT 05149

  Can't find the right house, nor the right location? This coveted Farm Ridge Lot could solve all your problems. This 12.9 acre lot has various terrain and private wooded views. This lot is on a quiet cul-de-sac named Woods Road West. You can decide how much land to clear - it's begging to have the land opened up to reveal the stunning views that neighboring houses enjoy. The lot was previously

  Joseph Karl William Raveis Real Estate Vermont Properties

  0 Woods Rd W Unit 5081865, Ludlow, VT 05149
• 

  

  

  /34

  $895,000

  • 5 Beds
  • 3.5 Baths
  • 3,631 Sq Ft

  193 Chester Arthur Rd, Hartford, VT 05001

  Perched on 2.7 private acres with a stunning westerly exposure, this exceptional contemporary Cape captures sweeping views of Vermont’s rolling hills, including the slopes of the Quechee Ski Hill. Framed by mature birch trees and towering pines, the setting is both peaceful and picturesque, offering spectacular sunsets and year-round beauty.Designed for comfort and gathering, the home

  Derek Cosentino Four Seasons Sotheby's Int'l Realty

  193 Chester Arthur Rd, Hartford, VT 05001
• 

  

  /19

  $345,000

  • Land
  • 6.48 Acres
  • $53,241 per Acre

  0 Oakridge Way, Woodstock, VT 05091

  Your dream home starts right here — with a blank canvas in one of Vermont's most coveted communities. This exceptional buildable lot on Oak Ridge Way presents a rare opportunity to design and construct your ideal residence on a quiet side road in Woodstock. Nestled within a highly sought-after neighborhood, surrounded by million dollar homes, this property offers the kind of setting that inspires

  Nancy Greenwood Watson Realty & Associates

  0 Oakridge Way, Woodstock, VT 05091
• 

  

  /14

  $1,560,000

  New Construction $65K PRICE INCREASE

  • 4 Beds
  • 4.5 Baths
  • 3,120 Sq Ft

  4070 Tichenor Rd, Hartford, VT 05059

  The Thistle at Mountain Stream — To be built by Mountain Stream at Quechee Lakes, the Thistle offers 3,120 square feet of contemporary living across two levels, paired with a single-bay tuck-under garage, separate heated storage with optional rec-room conversion, and a detached two-car garage. A long, low silhouette under a sweeping shed roof, vertical board-and-batten siding, and a dramatic

  Richard Higgerson Higgerson & Company

  4070 Tichenor Rd, Hartford, VT 05059
• 

  

  /14

  $239,000

  • Land
  • 10.1 Acres
  • $23,663 per Acre

  0 Christian St Unit 5084994, Hartford, VT 05001

  Beautiful, in town location. A very rare opportunity to own an in town Christian Street parcel of land. If you've been having a hard time finding the right home in this very tight housing market Or if you've been dreaming about new construction in the Hartford / Upper Valley area than look no further. This land parcel is conveniently located only minutes from Downtown White River Junction, VT. .

  Alex DeFelice The Clerkin Agency, P.C.

  0 Christian St Unit 5084994, Hartford, VT 05001
• 

  

  /56

  $1,395,000

  • 3 Beds
  • 2.5 Baths
  • 2,112 Sq Ft

  683 Reservoir Rd, White River Junction, VT 05001

  Welcome to Trail’s End - an oasis of peace and tranquility suffused with the restorative power of nature. Set amidst lush gardens and rolling lawns, this gorgeous timber frame house blends traditional looks with modern sensibilities and amenities, offering comfortable, light-filled, and highly functional spaces throughout. The beautifully appointed main floor primary bedroom features a spacious

  Zoe Hathorn Washburn Snyder Donegan Real Estate Group

  683 Reservoir Rd, White River Junction, VT 05001
• 

  

  /45

  $1,299,000

  $151K PRICE DROP

  • 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
• 

  

  /17

  $49,000

  • Land
  • 1.31 Acres
  • $37,405 per Acre

  1-61 Hawk Spur Rd, Plymouth, VT 05056

  Affordable lot in a convenient Plymouth Lakes Region location, close to all area amenities including skiing and golf at nearby Okemo and Killington Mountain Resorts. Enjoy all four seasons in the quiet community of Hawk West. On-site septic system and drilled well will be needed. Hawk Resort covenants are in place to protect your investment. Come build your Vermont dream home!

  Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

  1-61 Hawk Spur Rd, Plymouth, VT 05056
• 

  

  /58

  $749,000

  • 3 Beds
  • 3 Baths
  • 2,697 Sq Ft

  1641 W Hill Rd, Rochester, VT 05767

  Welcome to The Birches — a peaceful end-of-road retreat where serenity, privacy, and Vermont’s natural beauty come together. Surrounded by more than 7,000 acres of conserved national forest land, this exceptional property offers unmatched tranquility, abundant wildlife, and direct access to outdoor adventure in every season.Set in a quiet mountain setting, this thoughtfully designed

  Brandon Fowler RE/MAX North Professionals

  1641 W Hill Rd, Rochester, VT 05767
• 

  

  /32

  $2,300,000

  • 4 Beds
  • 4.5 Baths
  • 3,524 Sq Ft

  134 Chester Arthur Rd, Hartford, VT 05047

  A quality residence with 4.69 landscaped acres beautifully complimenting the estate! Entering into the grounds a graceful drive meanders through landscaped lawns to arrive at a stone patio and an appealing New England style residence. Conveniently, there is option to enter an attached garage with direct entrance to the residence. After crossing the stone patio, passing through the front door

  John Wetmore Wetmore Real Estate

  134 Chester Arthur Rd, Hartford, VT 05047
• 

  

  /12

  $120,000

  • Land
  • 3.24 Acres
  • $37,037 per Acre

  508 Mattson Rd, Chester, VT 05143

  This property offers so many possibilities! Nestled on a quiet dirt road in scenic Chester just 10 mile from Okemo, this 3.24-acre parcel offers the perfect blend of open space and wooded privacy. The front of the lot features a sunny, open field with a pole barn—ideal for storage, hobbies, or future expansion. As you move toward the back of the property, the land gently slopes up to a wooded

  Jessica Citera Cummings & Co

  508 Mattson Rd, Chester, VT 05143
• 

  

  /58

  $790,000

  $105K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 4,144 Sq Ft

  1607 Massey Rd, Springfield, VT 05156

  MOTIVATED SELLER!!! Nestled in the rolling countryside of Springfield, this 1810 Federal-style brick farmhouse stands proudly on 44 breathtaking acres—an offering rich in history, character, and Vermont lifestyle.Open fields stretch out from the home, ideal for gardens, small-scale farming, or simply soaking in the pastoral beauty. Wooded acreage invites exploration, wildlife watching, and

  Jessica Citera Cummings & Co

  1607 Massey Rd, Springfield, VT 05156
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  /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
• 

  

  /24

  $295,000

  • 4 Beds
  • 2 Baths
  • 1,992 Sq Ft

  37 Dee Haven, Sharon, VT 05065

  Looking to start your investment portfolio? This property is a great place to start. In a quiet Sharon cul-de-sac, this property has two 2-bedroom units, one on each floor. Newer roof, newer shared septic, poured concrete foundation. The lot includes 10.5 acres of land, majority of which abuts land owned by the Vermont Department of Fish & Wildlife, which connects to the White River.

  Devin Josler Black House Real Estate

  37 Dee Haven, Sharon, VT 05065
• 

  

  /60

  $1,395,000

  • 4 Beds
  • 3.5 Baths
  • 4,111 Sq Ft

  39 Wallis View Ln, Ludlow, VT 05149

  Set in the highly desirable South Hill Estates, this exceptional property pairs privacy with an unbeatable location just minutes from Okemo Mountain. Surrounded by nearly five acres, the home enjoys sweeping mountain views and a beautifully open landscape that invites year-round enjoyment. The yard is a true highlight—offering plenty of space to relax, entertain, and play. A picturesque pond

  Debra Staniscia Four Seasons Sotheby's Int'l Realty

  39 Wallis View Ln, Ludlow, VT 05149
• 

  

  /60

  $3,350,000

  • 5 Beds
  • 5 Baths
  • 3,212 Sq Ft

  166 Jewett Rd, Brownsville, VT 05037

  Stately hilltop home built by Silas Banister c.1800, recently undergone a complete restoration. Quality materials & craftsmanship throughout. It has gorgeous views of nearby Ascutney Mountain & long-range views of NH. The property consists of 98 acres made up of fields, hard & softwoods, trails, a large sugarbush (potential for a future boiling operation). Conserved by Upper Valley Land Trust,

  Dana Waters Dark Horse Realty

  166 Jewett Rd, Brownsville, VT 05037
• 

  

  /53

  $675,000

  • 3 Beds
  • 3 Baths
  • 2,916 Sq Ft

  133 Rousseau Rd, Royalton, VT 05068

  Extraordinary 9.93-acre property perched high above the charming village of Royalton, offering breathtaking panoramic views of central Vermont and beyond. On clear days, enjoy sweeping vistas stretching from Camel's Hump and Mount Mansfield to Mount Washington and New Hampshire's Presidential Range. Built in 2021, this thoughtfully designed home features an open-concept floor plan filled with

  Kyle Kershner Killington Pico Realty

  133 Rousseau Rd, Royalton, VT 05068
• 

  

  /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
• 

  

  /38

  $413,900

  $10K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,888 Sq Ft

  273 Route 5 N, Windsor, VT 05089

  Motivated seller! Price drop! A rare piece of Vermont history, thoughtfully preserved for modern living. Dating to 1790, this distinguished brick and frame Colonial stands as a testament to early New England craftsmanship — and it's ready for its next chapter. Meticulously maintained over the centuries and updated where it counts, this two-story home offers the warmth of wide-plank hardwood and

  Allison Griep BHHS Verani Upper Valley

  273 Route 5 N, Windsor, VT 05089
• 

  

  /56

  $3,650,000

  • 5 Beds
  • 4 Baths
  • 5,181 Sq Ft

  348 Turtle Hill Rd, Ludlow, VT 05149

  Set high with vistas of southern Vermont's valleys and mountains, "The Barn" is a remarkable custom timber frame retreat where exceptional craftsmanship meets breathtaking natural beauty. Completed in 2023 after two years of thoughtful design and construction, this residence was created to be a place of gathering, connection, and lasting memories for generations to come.Privately situated on

  Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

  348 Turtle Hill Rd, Ludlow, VT 05149
• 

  

  /4

  $1,300,000

  • 3 Beds
  • 2 Baths
  • 2,334 Sq Ft

  72 Wood Rd, Hartford, VT 05001

  US Route 4 in Vermont - the east/west corridor from I-89 and the Killington Ski Area. Highway frontage between Quechee and Woodstock, VT. Minutes from Dartmouth College in Hanover, NH; near the intersection of I-89 and 91 at the Connecticut River; also close to Northern New England’s major DH Medical complex and Cancer Center in Lebanon, NH, as well as the VA Hospital in White River Junction. 1.5

  Terry Boone Bassette Real Estate Group

  72 Wood Rd, Hartford, VT 05001
• 

  

  /3

  $199,000

  $21K PRICE DROP

  • Land
  • 50.45 Acres
  • $3,944 per Acre

  0 Missing Link Rd, Springfield, VT 05156

  Sitting high above Rte 5, this large parcel has a prime view out over the Connecticut River. There's a septic permit in place for a 5 bedroom home. You'll need to improve the old logging road to gain access to the top but once you do, there are 50 acres to explore. Enroll in the Use Value Program to reduce your taxes!

  Victoria Woods Brattleboro Area Realty

  0 Missing Link Rd, Springfield, VT 05156
• 

  

  /36

  $399,000

  $80K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,094 Sq Ft

  75 Naulahka Ln, Hartford, VT 05059

  This Quechee retreat feels like a tree house. Combining three lots provides a level of privacy that is becoming increasingly rare in the Upper Valley, and the vertical layout makes excellent use of that wooded backdrop.By placing the Great Room behind two large picture windows, the design creates a seamless visual transition between the interior and the forest canopy.With a bedroom and full bath

  Linda Hicks Quechee Lakes Real Estate Center

  75 Naulahka Ln, Hartford, VT 05059
• 

  

  /5

  $850,000

  • Land
  • 1.47 Acres
  • $578,231 per Acre

  97 Valley View Rd, Woodstock, VT 05091

  The justifiably proud owner of this property points out these features: Potential "Barnominium." Conveniently located just 1/4 mile from Woodstock Village town line and just 40 minutes from Killington Ski area. Built for an auto collection. Full bathroom, blown in insulation in ceiling, foam spray insulation in walls (with bug mesh in walls.) 3/4" sheet rock! All electrical is done in 3/4'

  John Wetmore Wetmore Real Estate

  97 Valley View Rd, Woodstock, VT 05091
• 

  

  /22

  $1,490,950

  New Construction Open Fri 12PM - 4PM $421K PRICE INCREASE

  • 5 Beds
  • 3.5 Baths
  • 2,709 Sq Ft

  399 Bentley Rd, Hartford, VT 05059

  The Evergreen at Mountain Stream — Currently under construction at 399 Bentley Road, the Evergreen offers 2,709 square feet of contemporary living across two finished levels, paired with a detached two-car garage. A long, low silhouette under a standing-seam metal roof, composite board-and-batten siding, and oversized windows give the home a distinctly modern presence — clean architectural lines

  Richard Higgerson Higgerson & Company

  399 Bentley Rd, Hartford, VT 05059
• 

  

  /6

  $175,000

  • Land
  • 1.02 Acres
  • $171,569 per Acre

  Lot 51 Partridge Rd, Ludlow, VT 05149

  1.02+/- acres. Lot 51. Ready to build. Prestigious neighborhood, some lots with views of Okemo Slopes with clearing. Very convenient to the village and Okemo Mountain Resort. This property is owned by a Vermont licensed real estate agent.

  Boris Lavanovich Mary W. Davis Realtor & Assoc., Inc.

  Lot 51 Partridge Rd, Ludlow, VT 05149
• 

  /2

  $26,900

  $2K PRICE DROP

  • Land
  • 1.9 Acres
  • $14,158 per Acre

  223 Falcon Loop Rd E, Rochester, VT 05767

  Build your Vermont retreat on this 1.90-acre wooded lot in thedesirable Great Hawk community in Rochester. Surrounded by natural beauty, this property offers a peaceful setting with access to hiking, skiing, and year-round outdoor recreation, plus nearby attractions like the Green Mountain National Forest and scenic Route 100. Rochester is loved for its quiet charm, local farms, and

  Derek Greene Derek Greene

  223 Falcon Loop Rd E, Rochester, VT 05767
• 

  

  /26

  $299,900

  • 2 Beds
  • 1.5 Baths
  • 1,063 Sq Ft

  253 Old Quechee Rd Unit 6C, Hartford, VT 05001

  OPEN HOUSE SUNDAY JUNE 7 FROM 2-4 PM. When we say turn-key, it is TURN-KEY! Come hang your clothes in the walk-in closet and put your feet up to enjoy this fully furnished Mill Run II condo in the beautiful Quechee Lakes community. This low-maintenance condo has been exceptionally well renovated. Some of the upgrades include: upgraded kitchen with granite counters, stainless steel appliances,

  Franchesca Collins Hall Collins Real Estate Group

  253 Old Quechee Rd Unit 6C, Hartford, VT 05001
• 

  

  /13

  $50,000

  • Land
  • 1.5 Acres
  • $33,333 per Acre

  2-63 Goshawk Dr, Plymouth, VT 05056

  Affordable opportunity to build your dream home in a quiet neighborhood located between Okemo and Killington Mountain Resorts, with nearby access to Echo Lake, Hawk Resort hiking trails, and Plymouth State Park. With utilities close by and the ability to connect to the community wastewater system, this lot is ready for your new Vermont home. Community covenants and design standards help protect

  Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

  2-63 Goshawk Dr, Plymouth, VT 05056
• 

  

  /14

  $239,000

  • 9 Beds
  • 2 Baths
  • 11,500 Sq Ft

  199 Summer St, Springfield, VT 05156

  A unique opportunity to acquire the former East School property at 199 Summer Street in Springfield, Vermont. Set on approximately 2.5 acres, the property includes a roughly 11,500 sq. ft. former school building with road access, municipal water and sewer, and Medium Density Residential zoning. Listed at $239,000, this property offers significant potential for multifamily housing, residential

  David White OwnerEntry.com

  199 Summer St, Springfield, VT 05156
• 

  

  /48

  $6,750,000

  New Construction $500K PRICE DROP

  • 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 63 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
• 

  /2

  $450,000

  • Land
  • 119 Acres
  • $3,782 per Acre

  00 Bradley Hill Rd Unit 121, Norwich, VT 05055

  Unusually large parcel of land in Norwich. 119 +/- ac with over 2500' of road frontage on delightful Bradley Hill Road. Close to town yet calm and quiet. The land abuts conservation land and the "Bradley Hill Loop" - a maintained trail. Not yet in Current Use though the forestry plan is ready to be implemented. A great opportunity to build in the Dresden School District.

  Jane Darrach Martha E. Diebold/Hanover

  00 Bradley Hill Rd Unit 121, Norwich, VT 05055
• 

  

  /37

  $865,000

  $320K PRICE DROP

  • 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
• 

  

  /60

  $1,350,000

  Open Fri 1PM - 3PM Coming Soon

  • 4 Beds
  • 3 Baths
  • 2,311 Sq Ft

  323 Turnpike Rd, Norwich, VT 05055

  Where to begin, this property has so many special facets: Antique Cape that has been sensitively updated consistent with the style of the house; a guest house (Cape) built in 2004; an amazing renovated barn ready to host gatherings of all sorts and plenty of storage under the main level;stonewalls, stone patio, raised stone patio, fenced garden space, large openlawn area at the back of

  Berna Rexford Four Seasons Sotheby's Int'l Realty

  323 Turnpike Rd, Norwich, VT 05055
• 

  

  /38

  $375,000

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

  847 Simonsville Rd, Andover, VT 05143

  Looking to find your own peaceful piece of the Vermont countryside? Look no further than this move in ready homestead on 51.2 rolling acres with twopaddocks already fenced and ready waiting for your animals. Also complete with two spacious sheds for animals or storage, and a chicken coop ready to house them. Established asparagus patch, garden plot,blueberry bushes, apple trees, and even

  Erin Kendall EXP Realty

  847 Simonsville Rd, Andover, VT 05143
• 

  

  /49

  $549,000

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

  1572 Skyline Dr, Springfield, VT 05156

  Nestled on 11.9 private acres, in the prestigious Skyline Drive area, this custom-built, one-owner home offers the perfect blend of tranquility, space, and opportunity. Ideally located just three miles from Crown Point Country Club and six miles from access to I89, this Southern VT retreat is also conveniently situated near some of the region's most sought-after recreational destinations,

  Kate Jarvis Williamson Group Sothebys Intl. Realty

  1572 Skyline Dr, Springfield, VT 05156
• 

  

  /53

  $525,000

  • 4 Beds
  • 2 Baths
  • 2,232 Sq Ft

  133 Baltimore Rd, North Springfield, VT 05150

  A true farm ready for its next chapter! These grounds have been lovingly tilled, gardened, sown, and harvested; the soil meticulously fed, and the pastures grazed by generations of animals. Hundreds of pounds of produce have been grown in and out of the greenhouse high tunnel. A massive, fixed-rack solar array covers the primary costs of electricity and feeds back into the grid. What is most

  Franchesca Collins Hall Collins Real Estate Group

  133 Baltimore Rd, North Springfield, VT 05150

Showing Results 241 - 280, Page 7 of 8