Windsor, VT Homes

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  /60

  $949,000

  • 6 Beds
  • 6 Baths
  • 5,497 Sq Ft

  31 Huntington Place Unit 1,2 & 3, Rochester, VT 05767

  Charming 1900s Village Building, Three Condo Units, One Incredible Opportunity!In the heart of Rochesters picturesque village, this beautifully restored early 1900s building is a rare investment opportunity, offered as a single property with three fully furnished condo units. Perfect for an owner-occupant, a multi-generational retreat, or a savvy investor, this historic gem blends classic

  Kate Cassidy Four Seasons Sotheby's Int'l Realty

  31 Huntington Place Unit 1,2 & 3, Rochester, VT 05767
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  /4

  $65,000 Sold Jul 29, 2025

  • Land
  • 22 Acres
  • $2,941 per Acre

  • 23 Days On Market

  403 Fiske Rd, Rochester, VT 05767

  This undeveloped land parcel offers house sites near the roadside, then the terrain drops off to the Howe Brook with much more land on the hillside to the south of the brook. Septic testing can take place prior to closing at buyers expense. There are old jeep trails to explore and not far from the recreational bike trails of Rochester Outdoor Collective. The lot is located on a town-maintained

  Patricia Harvey Xsell Realty LLC

  403 Fiske Rd, Rochester, VT 05767
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  /12

  Est $87,128 Not Listed For Sale

  2600 N Hollow Rd, Rochester, VT 05767

  2600 N Hollow Rd, Rochester, VT 05767
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  /60

  $1,275,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,315 Sq Ft

  1074 N Hollow Rd, Rochester, VT 05767

  Looking for complete privacy, spectacular long range views of the Green Mountains and a 3 BR/2 bath post and beam house with a pond, just three miles from the charming and vibrant village of Rochester? This could well be it! Sited on 233 ac. of forestland and a small field, including a named Vermont mountain (Mt. Cushman), extensive flower gardens, and 5 raised beds for vegetables. There is also

  Sarah Peluso IPJ Real Estate

  1074 N Hollow Rd, Rochester, VT 05767
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  /25

  $325,000 Sold Jul 11, 2025

  • 1,208 Sq Ft
  • $269/SF
  • 38 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1950

  3078 N Hollow Rd, Rochester, VT 05767

  Located in the sought after North Hollow section of Rochester is this 2 bdrm, 1 bath Ranch on 2 acres with attached garage and small outbuilding barn. Another larger barn/garage has the frame work erected with the rest of the materials on site for its next owner to complete. Charming country setting with great curb appeal including stone walls and set off the roadway surrounded by panoramic

  Patricia Harvey Xsell Realty LLC

  3078 N Hollow Rd, Rochester, VT 05767
• 

  

  /21

  Est $209,182 Not Listed For Sale

  • Studio
  • 1,500 Sq Ft

  230 S Main St, Rochester, VT 05767

  230 S Main St, Rochester, VT 05767
• 

  

  /54

  $949,000 Pending

  • 3 Beds
  • 3.5 Baths
  • 3,252 Sq Ft

  209 Saw Mill Hill, Rochester, VT 05767

  Sited on 25 acres with gorgeous mountain views, this renovated cape is here to complete your Vermont dream. Hike, ski or bike right out your back door- the mountain biking trials in Rochester are incredible! Owned solar panels are installed to help power the home. Walk in from the screened in porch, into a generous entryway with a large closet for coat and gear storage. A sitting area with pellet

  Sarah Peluso IPJ Real Estate

  209 Saw Mill Hill, Rochester, VT 05767
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  /21

  $95,000 Sold Jul 01, 2025

  • 528 Sq Ft
  • $180/SF
  • 31 Days On Market

  • 1 Bed
  • 0.5 Baths
  • Built 1976

  3306 Liberty Hill Rd, Rochester, VT 05767

  This adorable camp abutting the Green Mountain National Forest is the perfect weekend getaway for the outdoor enthusiast. You can enjoy snowmobiling, off-roading, snowshoeing, hunting, hiking and mountain biking right from your door. The list of upgrades and improvements is so extensive, you might forget you're still roughing it! There are new footings and support beams underneath, a standing

  Kyle Kershner Killington Pico Realty

  3306 Liberty Hill Rd, Rochester, VT 05767
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  /35

  Est $333,510 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,584 Sq Ft

  40 Cannon Dr, Rochester, VT 05767

  40 Cannon Dr, Rochester, VT 05767
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  /60

  $869,000

  • 4 Beds
  • 4.5 Baths
  • 4,088 Sq Ft

  1588 Austin Hill Rd, Rochester, VT 05767

  An iconic Robert Carl Williams design, completely reimagined by Robson Bilgen Architects in 1999, this one-of-a-kind masterpiece in Rochester’s Great Hawk community is a work of art inside and out. Perfectly sited on 2.7 acres of lush, landscaped grounds, it feels like a private sanctuary, with sweeping pagoda-inspired rooflines, recirculating ponds and waterfalls, dramatic stonework, and vibrant

  Kyle Kershner Killington Pico Realty

  1588 Austin Hill Rd, Rochester, VT 05767
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  /40

  $348,000 Sold Jun 18, 2025

  • 1,609 Sq Ft
  • $216/SF
  • 327 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1900

  64 and 96 State Garage Rd, Rochester, VT 05767

  Nestled along the tranquil White River in picturesque Rochester, Vermont, this unique property offers endless possibilities. The estate comprises two distinct lots: a sunny, level, 2-acre parcel featuring a charming 3-bedroom New England vernacular style home, and a vintage 3-bedroom mobile home with solid rental income, plus a separate 8.1-acre pasture, accessible via a deeded right of way,

  Kyle Kershner Killington Pico Realty

  64 and 96 State Garage Rd, Rochester, VT 05767
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  /11

  Est $345,521 Not Listed For Sale

  • 3 Beds

  1913 Maple Hill Rd, Rochester, VT 05767

  1913 Maple Hill Rd, Rochester, VT 05767
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  /60

  $569,000

  • 3 Beds
  • 2 Baths
  • 2,008 Sq Ft

  352 Edwins Pond Rd, Rochester, VT 05767

  Welcome to Tranquility in Vermont.This charming three-bedroom, two-bath home invites you to unwind and enjoy the peaceful beauty of Vermont living. With both a spacious great room and a cozy living room—each warmed by its own wood stove—you’ll always have the perfect place to relax.The home features wide plank wood floors throughout, a brand-new heating system with on-demand hot

  Katie McFadden RE/MAX North Professionals

  352 Edwins Pond Rd, Rochester, VT 05767
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  /14

  $349,000 Sold Jun 16, 2025

  • 1,440 Sq Ft
  • $242/SF
  • 6 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2002

  85 Edwins Pond Rd, Rochester, VT 05767

  A warm, welcoming and spacious home, with living space all on one level. An open concept kitchen, dining, and living room make this a great home for entertaining or relaxing. Sunlight spills in through large southern windows and a glass sliding door opens onto a large covered porch. The custom built pine kitchen will delight anyone who loves to cook. Ample storage in the large pantry cabinet with

  Jason Saphire www.HomeZu.com

  85 Edwins Pond Rd, Rochester, VT 05767
• 

  

  /25

  Est $541,736 Not Listed For Sale

  • 2 Beds
  • 3 Baths
  • 1,968 Sq Ft

  234 Osprey Run, Rochester, VT 05767

  234 Osprey Run, Rochester, VT 05767
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  /57

  $599,900

  • 3 Beds
  • 2.5 Baths
  • 1,835 Sq Ft

  2475 Little Hollow Rd, Rochester, VT 05767

  Quintessential VT Mountain Location with privacy & seclusion galore! Surrounded by thousands of acres of locally owned timberland, many abundant recreational opportunities to Mount Cushman and the magnificent Little Hollow recreational area. Absolutely Gorgeous 3 bedroom, 3 bath Modified Cape on 7.1 acres of open and wooded land, that is located at the very end of a Class 3 town maintained road,

  Paul H Rea Rural Vermont Real Estate

  2475 Little Hollow Rd, Rochester, VT 05767
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  /58

  $484,000 Sold Jun 03, 2025

  • 1,678 Sq Ft
  • $288/SF
  • 81 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1974

  1645 Austin Hill Rd Unit 55 and 57, Rochester, VT 05767

  This 4-bedroom, 2-bath home on a double lot in the desirable Great Hawk development has been thoughtfully updated over the years. Major improvements began in 2008 with a new porch, deck, standing seam roof, and enclosed breezeway. In 2009, new windows, insulation, and siding were installed. The home was further enhanced in 2018 with a beautifully remodeled kitchen featuring granite countertops

  Daniel Pol Killington Pico Realty

  1645 Austin Hill Rd Unit 55 and 57, Rochester, VT 05767
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  /27

  Est $344,192 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 772 Sq Ft

  119 Hillside Terrace, Rochester, VT 05767

  119 Hillside Terrace, Rochester, VT 05767
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  /31

  $481,500

  • 4 Beds
  • 3 Baths
  • 2,074 Sq Ft

  111 Forest Ln, Rochester, VT 05767

  Located in the sought after Great Hawk community of Rochester is this 4 bedroom, 3 bath home with updates that make maintaining this home easy on your checkbook. Solar array reduces power bill to minimum fee for 9 months out of the year. Heat pumps further reduce energy costs. This home could use some cosmetic updating as owner put home investment into the utility of the home, new roof and new

  Patricia Harvey Xsell Realty LLC

  111 Forest Ln, Rochester, VT 05767
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  /40

  $100,000 Sold Apr 17, 2025

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

  • 26 Days On Market

  1493 Brandon Mountain Rd, Rochester, VT 05767

  Elevated house site with gorgeous views across your lower meadow to the spectacular West Branch of the White River. Three acres to enjoy, nearly 300 feet of river frontage and a huge meadow that, while in the flood zone, is far below the house site. With some clearing the river view from the house will be even more amazing. House site already cleared, 3BR state septic permit in place, and this

  Clayton-Paul Cormier Jr Maple Sweet Real Estate

  1493 Brandon Mountain Rd, Rochester, VT 05767
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  /28

  Est $301,728 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,552 Sq Ft

  26 Brook St, Rochester, VT 05767

  26 Brook St, Rochester, VT 05767
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  /58

  $625,000 Pending

  • 4 Beds
  • 2 Baths
  • 2,490 Sq Ft

  216 Rocky Rd, Rochester, VT 05767

  High atop Jerusalem Hill, just south of the quintessential Vermont town of Rochester you will find a homestead that simply must be experienced in person - the photos will do no justice to the subject. The property is incredibly versatile, having multiple potential build sites, all with the ability to remain private from one another. There is a large, open meadow that the residence currently

  William Brokhof Vermont Backcountry Real Estate

  216 Rocky Rd, Rochester, VT 05767
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  /25

  $90,000 Sold Mar 28, 2025

  • Land
  • 34 Acres
  • $2,632 per Acre

  • 8 Days On Market

  4608 Vermont Route 100, Rochester, VT 05767

  Recreation is the name of the game with this property! Nestled in the scenic beauty of Rochester, this lot offers unparalleled access to hiking trails that have been enjoyed by neighbors over the years. While these trails may not be officially maintained, they lead to some of the most lovely views the area has to offer. Imagine meandering through lush VT and alongside the tranquil banks of the

  Jeremy Collins Ridgeline Real Estate

  4608 Vermont Route 100, Rochester, VT 05767
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  /30

  Est $342,201 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,900 Sq Ft

  34 Cannon Dr, Rochester, VT 05767

  34 Cannon Dr, Rochester, VT 05767
• 

  

  /21

  $395,000

  • Land
  • 146 Acres
  • $2,711 per Acre

  1498 N Hollow Rd, Rochester, VT 05767

  145 acres of pristine Vermont wilderness, stewarded under a comprehensive forest management plan within the state’s Current Use Program—ensuring a healthy, sustainable forest, abundant wildlife habitat, and impressively low property taxes. Tucked away in the coveted North Hollow section of Rochester, this extraordinary parcel is threaded with miles of manicured walking trails that begin at a

  Kyle Kershner Killington Pico Realty

  1498 N Hollow Rd, Rochester, VT 05767
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  /39

  $365,000 Sold Mar 17, 2025

  • 1,460 Sq Ft
  • $250/SF
  • 7 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1990

  604 Mount View Loop, Rochester, VT 05767

  Step into your dream Vermont escape! This charming 3-bedroom, 2-bath Cape Cod home sits on a peaceful 2.24-acre lot and is the perfect blend of comfort and rural serenity. Built in 1990, this move-in ready property features a bright, updated kitchen with stainless steel appliances, a cozy living room with a wood stove, and modern flooring throughout. Enjoy mountain views, a private wooded

  Nick Sicard EXP Realty

  604 Mount View Loop, Rochester, VT 05767
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  /40

  Est $396,253 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,836 Sq Ft

  802 Oak Lodge Rd, Rochester, VT 05767

  802 Oak Lodge Rd, Rochester, VT 05767
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  /2

  $184,000

  • Land
  • 17 Acres
  • $10,824 per Acre

  tbd Quarry Hill Rd, Rochester, VT 05767

  North Hollow offers the beauty and country setting you expect from Vermont. This land parcel is subdivided off a homesite with an added parcel to complete the 17 acres. Situated off the roadside, you will enjoy privacy and mountain views. Perfect for a solar installation with southwest exposure. Better yet, this parcel is across the street from access to the ROC Mt bike trail system. Only 30

  Patricia Harvey Xsell Realty LLC

  tbd Quarry Hill Rd, Rochester, VT 05767
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  /12

  $96,000 Sold Jan 31, 2025

  • Land
  • 6 Acres
  • $16,552 per Acre

  • 158 Days On Market

  952 Bethel Mountain Rd Unit 1, Rochester, VT 05767

  Perched just above the quaint town of Rochester, VT are three glorious parcels waiting for you to build your dream home in complete seclusion. Mountain views as far as the eye can see. Power and fiber optic internet at the road. Well built road to the top of the parcel, designed to allow for three potential lots. Less than 3 hours from Boston, and just a few minutes to town for all the basic

  William Brokhof Vermont Backcountry Real Estate

  952 Bethel Mountain Rd Unit 1, Rochester, VT 05767
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  /36

  Est $414,518 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,333 Sq Ft

  571 Wing Farm Rd, Rochester, VT 05767

  571 Wing Farm Rd, Rochester, VT 05767
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  /42

  $359,000

  • 3 Beds
  • 1 Bath
  • 1,144 Sq Ft

  919 Vermont Route 100, Rochester, VT 05767

  Situated on a sun-drenched, level yard you will find this stunning ranch-style home, equipped with the latest amenities, including new electrical andheating systems, water heater, insulation, windows and doors, siding, interiorwalls, recessed lighting thoughout, hardwood floors, spacous kitchen, and abath featuring a granite vanity. A brand new wood stove offers an additional heating

  Christopher King King Real Estate

  919 Vermont Route 100, Rochester, VT 05767
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  /48

  $275,000 Sold Dec 30, 2024

  • 1,154 Sq Ft
  • $238/SF
  • 33 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1950

  78 S Hollow Ln, Rochester, VT 05767

  Look no further, you have found your little slice of heaven. This adorable cottage was built in the 1950s for a school teacher and has been lovingly cared for, renovated and upgraded over the years by the current owner. The barn, originally built in the 1700s, was moved from another location in Rochester and reassembled onsite. In addition there is a little "she shed" with a screened in porch and

  William Brokhof Vermont Backcountry Real Estate

  78 S Hollow Ln, Rochester, VT 05767
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  /40

  Est $719,013 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 3,844 Sq Ft

  385 Access Rd, Rochester, VT 05767

  385 Access Rd, Rochester, VT 05767
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  /7

  $15,000

  • Land
  • 1.10 Acres
  • $13,636 per Acre

  868 Maple Hill, Rochester, VT 05767

  Welcome to Great Hawk Owner's Association! This is a 1.1 acre parcel ready for you to build an amazing vacation home or a full time residence. There are plenty of activities to keep you busy once you move in; whether you like to mountain bike on all of the local trails, enjoy a short drive to ski at Killington or Sugarbush, or recreate close to home on the Association's hiking and snowshoeing

  Michael Brancoforte KW Vermont-Stowe

  868 Maple Hill, Rochester, VT 05767
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  /33

  $460,000 Sold Dec 18, 2024

  • 1,038 Sq Ft
  • $443/SF
  • 49 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1974

  89 Falcon Loop E, Rochester, VT 05767

  Welcome to your dream home in the desirable Great Hawk Community! This stunning two-story property offers spacious and comfortable living with new windows and sliders that fill the home with natural light. The ground floor features an open-concept kitchen and living area with a cozy wood-stove insert, perfect for relaxing evenings. This level also includes a bedroom and a full bathroom. Enjoy the

  Elevations Team Real Broker LLC

  89 Falcon Loop E, Rochester, VT 05767
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  /40

  Est $895,918 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,158 Sq Ft

  51 Great Pond Rd, Rochester, VT 05767

  51 Great Pond Rd, Rochester, VT 05767
• 

  

  /44

  $368,000

  • 3 Beds
  • 2 Baths
  • 2,224 Sq Ft

  165 N Main St, Rochester, VT 05767

  NEW PRICE! Experience the "Feng Shui" of the Pineapple Outpost in beautiful Rochester, a charming and vibrant town. This captivating early Post and Beam home presents an exquisite blend of historic charm and modern conveniences. Inside, discover wide pine floors, exposed beams, and a cozy fireplace in the main-level primary bedroom, each element showcasing the home’s rustic elegance. With two

  Gail Engel & Völkers Okemo

  165 N Main St, Rochester, VT 05767
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  /26

  $26,500 Sold Dec 10, 2024

  • Land
  • 1.60 Acres
  • $16,562 per Acre

  • 241 Days On Market

  14 Osprey Run, Rochester, VT 05767

  Gently sloping wooded building lot with potential long range views in the desirable Great Hawk community of Rochester, VT. With a sunny, southwest exposure, this is the perfect place to build the mountain home of your dreams. The property is conveniently located less than 3 miles from the quaint village of Rochester, and close to several world class ski resorts, as well as the Velomont Trail for

  Kyle Kershner Killington Pico Realty

  14 Osprey Run, Rochester, VT 05767
• 

  

  /18

  Est $281,048 Not Listed For Sale

  • 6 Beds
  • 3 Baths
  • 2,512 Sq Ft

  19 Austin Hill Rd, Rochester, VT 05767

  19 Austin Hill Rd, Rochester, VT 05767
• 

  

  /59

  $410,000

  • 2 Beds
  • 2 Baths
  • 2,400 Sq Ft

  54 Twitchell Settlement, Rochester, VT 05767

  "Nestled on over three private acres, this Vermont retreat exudes rustic charm and modern comfort. The soaring cathedral ceilings and floor-to-ceiling arched windows in the great room flood the space with natural light, creating a warm and inviting atmosphere. The open-concept layout seamlessly connects the kitchen, dining, and living areas, ideal for gatherings or quiet moments by the pellet

  Nick Sicard EXP Realty

  54 Twitchell Settlement, Rochester, VT 05767

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