Windsor, VT Homes

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  /60

  $1,500,000

  • 10 Beds
  • 12 Baths
  • 5,500 Sq Ft

  1589 Main St, Cavendish, VT 05142

  Glimmerstone Mansion—an extraordinary legacy estate where timeless elegance meets modern sophistication. Set on 2.4± beautifully landscaped acres, this iconic property—listed on the National Historic Register—has been meticulously restored, thoughtfully upgraded, and exquisitely furnished. At the heart of the estate is the grand 10-bedroom mansion, where nearly every bedroom and gathering space

  Kevin Barnes William Raveis Real Estate Vermont Properties

  1589 Main St, Cavendish, VT 05142
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  /23

  $210,000 Sold May 30, 2025

  • 1,352 Sq Ft
  • $155/SF
  • 44 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1938

  28 Bishops Loop, Windsor, VT 05089

  OFFER DEADLINE: MONDAY 4/21/25 6pmReady to start your real estate investment journey? This 3-bedroom home is the perfect opportunity for someone eager to build equity and willing to add their own personal touch. Upstairs, you’ll find three spacious bedrooms and a convenient half bath—ideal for families or future tenants.The eat-in kitchen is ready for your updates, offering a blank canvas to

  Katie Ladue Gilbert KW Vermont Woodstock

  28 Bishops Loop, Windsor, VT 05089
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  /26

  Est $184,611 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,452 Sq Ft

  1092 Weeden Hill Rd, Windsor, VT 05089

  1092 Weeden Hill Rd, Windsor, VT 05089
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  /41

  $465,000

  • 3 Beds
  • 2 Baths
  • 2,432 Sq Ft

  17 Bixby Rd, Ludlow, VT 05149

  This warm and welcoming home combines classic charm with practical comfort, offering cozy spaces that invite you to unwind and make yourself at home. There’s so much to love here—from the spacious layout and warm interior touches to thoughtful features like the heated driveway and sun-filled rooms.The sun-drenched kitchen features white cabinetry, stainless appliances, and a spacious breakfast

  Frank Provance Diamond Realty

  17 Bixby Rd, Ludlow, VT 05149
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  /50

  $486,000 Sold May 30, 2025

  • 2,772 Sq Ft
  • $175/SF
  • 44 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1972

  225 Brothers Rd, Hartland, VT 05048

  Tucked away on four acres, this inviting home offers the perfect blend of comfort, charm, and versatility. Step inside through a proper Vermont mudroom - complete with benches and storage to keep all your seasonal gear organized. From there, the spacious lower level welcomes you with a cozy family room, ideal for movie nights, game nights, or just relaxing with loved ones. A convenient 3/4 bath,

  Jaime Durell BHHS Verani Upper Valley

  225 Brothers Rd, Hartland, VT 05048
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  /29

  Est $266,101 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,142 Sq Ft

  74 Union St, Windsor, VT 05089

  74 Union St, Windsor, VT 05089
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  /12

  $249,000

  • 3 Beds
  • 1 Bath
  • 1,440 Sq Ft

  419 Coach Rd, Chester, VT 05143

  Price Reduction! Come see this private 2-acre lot, off a side street close to the picturesque Chester village. This well maintained 1968 mobile home has a bright open concept addition. Close to ski mountains and other snowmobile trails. Make this a Vermont getaway or a permanent home joining a wonderful community.

  Amy Carson Lowe's Real Estate, LLC

  419 Coach Rd, Chester, VT 05143
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  /28

  $445,000 Sold May 30, 2025

  • 2,000 Sq Ft
  • $222/SF
  • 6 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1980

  54 Gifford Rd, White River Junction, VT 05001

  Welcome to this well-maintained 3-bedroom, 2-bath split-entry ranch, perfectly set back from the road for added privacy and peaceful living. Located in the desirable town of Hartford, this home offers both convenience and comfort in a prime Upper Valley location.Enjoy the ease of walking to nearby schools, athletic fields, and the local hockey rink—perfect for active lifestyles and community

  Katie Ladue Gilbert KW Vermont Woodstock

  54 Gifford Rd, White River Junction, VT 05001
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  /40

  Est $247,735 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,728 Sq Ft

  2 Terrace St, Windsor, VT 05089

  2 Terrace St, Windsor, VT 05089
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  /58

  $995,000

  • 3 Beds
  • 3.5 Baths
  • 2,544 Sq Ft

  725 Flamstead Rd, Chester, VT 05143

  Immaculately maintained 2,700+ sq ft home offers privacy, peace, and mountain views—just 15 minutes to Okemo Mountain and 4 minutes to the village of Chester. Step inside to find an open, flowing layout with timeless and gorgeous Brazilian rosewood floors, a wood burning fireplace in the living room, and walls of windows that frame the landscape. The family chef will happily welcome opportunities

  Suzanne Garvey Mary W. Davis Realtor & Assoc., Inc.

  725 Flamstead Rd, Chester, VT 05143
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  /45

  $370,000 Sold May 30, 2025

  • 1,248 Sq Ft
  • $296/SF
  • 109 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2005

  4189 Stony Brook Rd, Stockbridge, VT 05772

  Private Vermont Retreat for Outdoor Enthusiasts! Escape to your own wonderful haven nestled against the Vermont Wildlife Management Area to ensure lasting privacy and unspoiled natural beauty. Step off your porch and onto a VAST network of snowmobiling, VASA for ATV’s, and mountain biking trails, offering year-round recreation right from your doorstep. Just a short walk to the A-T trails. Whether

  Will Spanos KW Vermont-Killington

  4189 Stony Brook Rd, Stockbridge, VT 05772
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  /40

  Est $372,449 Not Listed For Sale

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

  172 State St, Windsor, VT 05089

  172 State St, Windsor, VT 05089
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  /26

  $95,000

  • Land
  • 0.86 Acre
  • $110,465 per Acre

  00 Greeley Shunpike, Hartford, VT 05001

  Discover .86± acres of prime land on Greeley Shunpike Rd in beautiful Quechee, VT. This is the last lot on a private, gently sloping, shared drive - nestled within the prestigious Quechee Lakes Landowners Association (QLLA). Enjoy full membership in The Quechee Club, offering access to 6,000+ acres of manicured greenways, two championship golf courses (Lakeland and Highland), indoor & outdoor

  John Bassette Bassette Real Estate Group

  00 Greeley Shunpike, Hartford, VT 05001
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  /32

  $350,000 Sold May 30, 2025

  • 3,990 Sq Ft
  • $88/SF
  • 232 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 1900

  30 Union St, Windsor, VT 05089

  Step into timeless elegance with this grand Victorian home, beautifully situated on a charming in-town lot. This stately residence showcases stunning hardwood floors throughout, preserving its classic heritage while offering modern comforts. The spacious first-floor bedroom features an en suite bath, providing both luxury and convenience. A cozy fireplace adds warmth and character to the main

  Katie Ladue Gilbert KW Vermont Woodstock

  30 Union St, Windsor, VT 05089
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  /18

  Est $212,343 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,514 Sq Ft

  159 State St, Windsor, VT 05089

  159 State St, Windsor, VT 05089
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  /49

  $1,175,000

  • 4 Beds
  • 4 Baths
  • 3,920 Sq Ft

  1847 Trebo Rd, Chester, VT 05143

  With only 50 stone homes in all of Vermont, this one stands out as possibly the most beautiful; uniquely situated on 20 acres of gorgeous greenlawn, fields, forest, rolling hills, extensive stone walls. A mere 2 miles to Chester. Since 2020 the house has been transformed & restored w/improvements such as interior & exterior paint, new windows & French Doors, stone steps & walkways, 50 panel

  Gary Coger Four Seasons Sotheby's Int'l Realty

  1847 Trebo Rd, Chester, VT 05143
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  /28

  $1,390,000 Sold May 30, 2025

  • 4,000 Sq Ft
  • $348/SF
  • 245 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2012

  504 Chapel Hill Rd, Norwich, VT 05055

  StoneRidge: A custom designed energy efficient house built in 2012. Sited on a ridge (1400’ elevation) surrounded by (23) forested acres accessed by a 1⁄4 mile driveway off a well- maintained town road. The design offers a flexible floor plan with three separate private residences. The main floor boasts single-level living, including an ensuite bedroom with a 3⁄4 bath, half bath off the hall,

  David White OwnerEntry.com

  504 Chapel Hill Rd, Norwich, VT 05055
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  /25

  Est $233,742 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,600 Sq Ft

  153 State St, Windsor, VT 05089

  153 State St, Windsor, VT 05089
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  /52

  $235,000

  • 3 Beds
  • 1 Bath
  • 1,152 Sq Ft

  34 Dewey St, Springfield, VT 05156

  Wow! What a sweet well cared for home, loaded with charm. The original owner lived here from when it was built in 1940 until 2005, when it was purchased by the current owner. This property is so cute and cozy, and you will be amazed by the many features such as wainscoting, antique type ceilings, all-natural unpainted woodwork, rolling island in the kitchen, the original kitchen sink, hardwood

  Glenn Olney Barrett and Valley Associates Inc.

  34 Dewey St, Springfield, VT 05156
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  /50

  $950,000 Sold May 30, 2025

  • 3,175 Sq Ft
  • $299/SF
  • 263 Days On Market

  • 5 Beds
  • 2.5 Baths
  • Built 1907

  218 Gunderson Rd, Chester, VT 05143

  This quintessential 4 bedroom (with a septic permit for up to 5 bedrooms)/2.5 bathroom farmhouse, fully renovated and absolutely gorgeous, is perched on a grassy knoll overlooking 32 acres of rolling meadow, hardwood forest and private pond. The modern touches that are essential for today's style of living pair perfectly with the warmth and charm of an old farmhouse. The house was renovated in

  Joseph Karl William Raveis Real Estate Vermont Properties

  218 Gunderson Rd, Chester, VT 05143
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  /32

  Est $329,714 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 2,273 Sq Ft

  18 Pine St, Windsor, VT 05089

  18 Pine St, Windsor, VT 05089
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  /40

  $1,499,000

  • 4 Beds
  • 3.5 Baths
  • 2,184 Sq Ft

  51 Alpine Way Unit A4, Ludlow, VT 05149

  Your Perfect Mountain Getaway: Ski-In/Ski-Out End-Unit Townhouse!Imagine stepping right onto the slopes from this exceptional 4-bedroom, 3.5-bath townhouse-style condominium. As an end unit, you'll appreciate the added privacy, especially in the en-suite primary suite with no neighbors above. The main floor is designed for easy living with a practical mudroom entry, a convenient half bath,

  Michael Normyle Mary W. Davis Realtor & Assoc., Inc.

  51 Alpine Way Unit A4, Ludlow, VT 05149
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  /26

  $311,688 Sold May 30, 2025

  • 2,702 Sq Ft
  • $115/SF
  • 387 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1850

  3590 Vt 103, Chester, VT 05143

  Fully furnished! Thoughtfully upgraded home on .89 acres located in the beautiful area of Gassetts in Chester, Vermont. Easy access to I-91, 10 minutes to Okemo, 20 minutes to Magic Mountain, 30 minutes to Bromley, 40 minutes to Killington and under an hour drive to Stratton ski resort. This three bedroom, two bathroom home has an open concept. Two bedrooms on the second floor and one bedroom

  Jessica Samples BHG Masiello Keene

  3590 Vt 103, Chester, VT 05143
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  /13

  Est $184,871 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 1,800 Sq Ft

  14 Mccarty Ave, Windsor, VT 05089

  14 Mccarty Ave, Windsor, VT 05089
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  /22

  $350,000

  • 2 Beds
  • 1.5 Baths
  • 1,356 Sq Ft

  355 Lyman Batcheller Rd Unit B, Hartford, VT 05001

  Welcome to easy living in the heart of Quechee Lakes! This 2-bedroom condo in the desirable Salt Box association offers effortless entry and a comfortable, open floor plan perfect for relaxing or entertaining. The updated kitchen features modern finishes and opens seamlessly to the dining and living areas, where a cozy wood-burning fireplace creates a warm and inviting atmosphere. Step outside to

  Kasia Butterfield Coldwell Banker LIFESTYLES - Quechee

  355 Lyman Batcheller Rd Unit B, Hartford, VT 05001
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  /13

  $542,000 Sold May 30, 2025

  • 1,369 Sq Ft
  • $396/SF
  • 462 Days On Market

  • 2 Beds
  • 3 Baths
  • Built 2008

  193 Jackson Gore Unit 744/746, Ludlow, VT 05149

  Bixby House 744/746 Whole Ownership. This luxury two-bedroom, valley side home features fully-equipped kitchen with stainless steel appliances, tiled back splash, farm sink and granite counters. The cozy living room includes a dining area and gas fireplace. The tiled foyer entry provides storage for outdoor gear. Primary bedroom has a king bed and a spacious master bath with his and her sinks.

  Laurene Skinner Mary W. Davis Realtor & Assoc., Inc.

  193 Jackson Gore Unit 744/746, Ludlow, VT 05149
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  /39

  Est $365,386 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,156 Sq Ft

  1670 Marton Rd, Windsor, VT 05089

  1670 Marton Rd, Windsor, VT 05089
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  /38

  $750,000

  • 3 Beds
  • 2 Baths
  • 2,568 Sq Ft

  75 Lyon Rd, South Royalton, VT 05068

  Return to yesteryear in this Late 1700s Colonial on 35 acres+-. Attention hobby farmers with goats, sheep, etc. This mini- farm features a modern milking parlor with equipment. this classic home has five fireplaces, spacious rooms, two full baths, and numerous improvements, making this a traditional treasure in Royalton, Vt. A 24 x 24 garage/workshop/ storage, and modern wood boiler are only

  Dean Goulet Dunrovin Real Estate

  75 Lyon Rd, South Royalton, VT 05068
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  /20

  $361,000 Sold May 29, 2025

  • 1,104 Sq Ft
  • $327/SF
  • 4 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1963

  113 Beech St, White River Junction, VT 05001

  This conveniently located 2 bedroom home is packed with charm and convenience. The main floor has a beautiful fireplaced living/dining room, sunny kitchen with lots of pantry space and a solarium window, and two generously sized bedrooms. The first floor tiled bathroom has a jetted walk-in tub and laundry hookups. The semi-finished basement has a second bathroom with shower, family room,

  Jolin Salazar Kish KCC Properties Realty, Inc.

  113 Beech St, White River Junction, VT 05001
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  /4

  Est $185,162 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,024 Sq Ft

  17 Maple St, Windsor, VT 05089

  17 Maple St, Windsor, VT 05089
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  /19

  $229,000

  • Land
  • 68 Acres
  • $3,343 per Acre

  0 Spencer Hollow Rd Unit 5048342, Springfield, VT 05156

  Behold this rare opportunity to own 68 acres of pristine Vermont land located on a quiet, town-maintained dirt road in the peaceful hills of Springfield. This expansive parcel is a dream for outdoor enthusiasts—offering direct access to nature with miles of established trails, a diverse and healthy forest, and abundant wildlife.Bordering the beloved Muckross State Park—over 200 acres of

  Daire Gibney Barrett and Valley Associates Inc.

  0 Spencer Hollow Rd Unit 5048342, Springfield, VT 05156
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  /2

  $201,000 Sold May 29, 2025

  • 1,048 Sq Ft
  • $192/SF
  • 5 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1915

  16 Mary St, Springfield, VT 05156

  Convenient, Comfortable, and Move-In Ready! This affordable gem offers the perfect blend of privacy and accessibility—just minutes from stores, schools, and I-91, yet peacefully located on a quiet dead-end street. The main floor features an open-concept layout combining the kitchen, living, and dining areas, along with a convenient half bath. The kitchen includes a recently added pantry,

  Chelsea Richardson Barrett and Valley Associates Inc.

  16 Mary St, Springfield, VT 05156
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  /23

  Est $175,792 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 2,009 Sq Ft

  149 Main St, Windsor, VT 05089

  149 Main St, Windsor, VT 05089
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  /47

  $549,000

  • 4 Beds
  • 2 Baths
  • 2,300 Sq Ft

  127 Pleasant St, Cavendish, VT 05142

  This lovingly restored Arts and Crafts style home is located just 10 minutes from Okemo Mountain. Built in 1928, this home sits on a peaceful, elevated street in Cavendish, just steps from the town’s sledding hill. Owned by the same family for 20 years, the memories made here are priceless. The children learned to ski at Okemo and with everyone grown, the family is ready to pass along this

  Tyleen Murray Kelley Real Estate, Inc.

  127 Pleasant St, Cavendish, VT 05142
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  /60

  $3,400,000 Sold May 29, 2025

  • 6,184 Sq Ft
  • $550/SF
  • 237 Days On Market

  • 5 Beds
  • 6.5 Baths
  • Built 2004

  4 Morning Star, Ludlow, VT 05149

  Accepting Back Up Offers. One of the most coveted homes on Okemo is ready for its new owner. Welcome to a spectacular, Montana lodge-style retreat nestled in a prime slopeside location on Okemo Mountain, adjacent to Solitude Village Day Lodge. This breathtaking ski-in/ski-out home sits at the top of Daybreak Trail, offering unrivaled mountain views in every direction. Crafted from Montana lodge

  Joseph Karl William Raveis Real Estate Vermont Properties

  4 Morning Star, Ludlow, VT 05149
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  /40

  Est $482,814 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,024 Sq Ft

  29 Main St, Windsor, VT 05089

  29 Main St, Windsor, VT 05089
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  /45

  $489,900

  • 4 Beds
  • 3 Baths
  • 2,289 Sq Ft

  114 Monument Hill Rd, Springfield, VT 05156

  HUGE PRICE REDUCTION! OWNER HAS MOVED SO THE PROPERTY MUST BE SOLD. POSSIBLE OWNER FINANCING!! This Hilltop Homestead/Mini farm boasts 5 acres of mostly open land and a sprawling 4,000 plus sq. ft. ranch style home with a full finished walkout basement with attached 2 car garage and numerous barns and outbuildings. Easy access to Springfield or Chester and I-91. The home features a huge primary

  Chris Long BHG Masiello Brattleboro

  114 Monument Hill Rd, Springfield, VT 05156
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  /22

  $165,000 Sold May 28, 2025

  • Land
  • 50 Acres
  • $3,300 per Acre

  • 0 Days On Market

  674 Vermont 12, Hartland, VT 05048

  50 wooded Acres available for your dreams to materialize. Lovely and substantial rolling brook with an internal trail system. Majority of property would be accessible by a new bridge which would need to be built. Extensive road frontage and good parking. Great deer hunting grounds and big timber with old growth forest. Older structures are not salvageable and would need to be removed. Excellent

  John Bassette Bassette Real Estate Group

  674 Vermont 12, Hartland, VT 05048
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  /36

  Est $838,607 Not Listed For Sale

  • 9 Beds
  • 8.5 Baths
  • 6,232 Sq Ft

  26 Main St, Windsor, VT 05089

  26 Main St, Windsor, VT 05089
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  /38

  $109,900

  • 2 Beds
  • 3 Baths
  • 1,367 Sq Ft

  505/507 Qtr I Adams House, Ludlow, VT 05149

  Adams House Unit 505/507 QII: Quarter ownership. This 2 Bedroom, 3 Bathroom lock-out style unit that sleeps 8 in Adams House is in an excellent location. When you park in the heated North garage, you find yourself only steps away from the unit which is located on the first floor. A very short walk down the hall and you pass the owners locker location. Walk into the living room and you'll be

  Matthew Bellantoni Mary W. Davis Realtor & Assoc., Inc.

  505/507 Qtr I Adams House, Ludlow, VT 05149

Showing Results 641 - 680, Page 17 of 18