Windsor, VT Homes in ZIP Code 05143

• 

  

  

  /43

  $400,000 Sold Apr 25, 2025

  • 1,800 Sq Ft
  • $222/SF
  • 106 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1984

  3057 Vermont 11, Chester, VT 05143

  Unique Chester property on 10.08+/- acres with home business potential! This 3 bedroom, 1.5 bath Contemporary has lovely grounds that feature a pond, landscaped rock gardens, a vegetable garden and ample open space for more gardening endeavors. The detached 3-bay garage offers multiple large spaces and oversized doors. Whether you are an artist, contractor, carpenter or mechanic, the high

  Geralyn Donohue Engel & Völkers Okemo

  3057 Vermont 11, Chester, VT 05143
• 

  

  

  /34

  Est $295,595 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,610 Sq Ft

  346 1st Ave, Chester, VT 05143

  346 1st Ave, Chester, VT 05143
• 

  

  

  /49

  $1,100,000

  • 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
• 

  

  /2

  $330,000 Sold Apr 22, 2025

  • 2,008 Sq Ft
  • $164/SF
  • 318 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1850

  117 S Main St, Chester, VT 05143

  Opportunity awaits! This three-unit property has been very well maintained with 2 of the units being recently renovated and refreshed ready to be rented. The outside has recently been painted aswell and is ready to be owner occupied or rented out. This investment features an in-town location within walking distance to shopping, restaurants and local conveniences. This property also includes

  Thaddeus Abare Barrett and Valley Associates Inc.

  117 S Main St, Chester, VT 05143
• 

  

  

  /28

  Est $253,457 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 943 Sq Ft

  386 1st Ave, Chester, VT 05143

  386 1st Ave, Chester, VT 05143
• 

  

  /13

  $165,000

  • Land
  • 1.20 Acres
  • $137,500 per Acre

  4769 Pikes Falls Rd, Jamaica, VT 05143

  A Rare Vermont Gem:This 1.2-acre parcel offers what few can—a front-row seat to one of Southern Vermont’s most breathtaking natural landscapes. Abutting the renowned Pikes Falls swimming hole and waterfall, this property is the equivalent of what would be Vermont’s oceanfront real estate.A wooded path leads directly from the land to the pristine falls, which are preserved by the

  Rachel Febbie EXP Realty

  4769 Pikes Falls Rd, Jamaica, VT 05143
• 

  

  /34

  $340,000 Sold Mar 27, 2025

  • 2,220 Sq Ft
  • $153/SF
  • 10 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1860

  489 Main St, Chester, VT 05143

  This beautifully renovated farmhouse offers a perfect mix of classic charm and modern updates, located just a short distance from the historic town green, shopping, and dining. The home features a spacious living room and cozy family room, providing plenty of space for both relaxation and entertainment. A dining area off the modern kitchen is perfect for family meals or hosting guests. The wood

  Gary Coger Four Seasons Sotheby's Int'l Realty

  489 Main St, Chester, VT 05143
• 

  

  /40

  Est $470,108 Not Listed For Sale

  • 6 Beds
  • 3 Baths
  • 3,892 Sq Ft

  595 Main St, Chester, VT 05143

  595 Main St, Chester, VT 05143
• 

  

  /23

  $80,000

  • Land
  • 3.99 Acres
  • $20,050 per Acre

  00 Simonsville Rd, Andover, VT 05143

  3.99 +/- acres in Andover close to year round recreation of surrounding towns. This lot was approved by Vt ww dept. in 2008 for a 4 bedroom home and has being updated with a new survey and a revised engineered plan with relocation of the proposed leach field is in process. Located along almost 1000' of the Williams River, after two major storm events, this lot has not lost much ground. A driveway

  Geralyn Donohue Engel & Völkers Okemo

  00 Simonsville Rd, Andover, VT 05143
• 

  

  /39

  $385,000 Sold Mar 20, 2025

  • 1,518 Sq Ft
  • $254/SF
  • 14 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1986

  2240 Baltimore Rd, Chester, VT 05143

  Charming Vermont Retreat Near Okemo MountainNestled in the serene hills of Baltimore, Vermont, this welcoming property offers a perfect blend of privacy and proximity to outdoor adventure. Just a short drive to Okemo Mountain, this home is a nature lover’s dream.This well-maintained home features a thoughtful layout with a bedroom on each level, including a walkout basement that could serve as a

  Morriah Adams BHG Masiello Brattleboro

  2240 Baltimore Rd, Chester, VT 05143
• 

  

  /24

  Est $567,630 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,622 Sq Ft

  548 Main St, Chester, VT 05143

  548 Main St, Chester, VT 05143
• 

  

  /26

  $225,000

  • 3 Beds
  • 1 Bath
  • 1,327 Sq Ft

  160 Depot St, Chester, VT 05143

  Don’t miss this incredible opportunity to own a lovingly maintained turn-key Victorian home nestled in the heart of charming Chester, Vermont. Whether you're seeking a warm and welcoming ski retreat or a comfortable year-round residence, this timeless property offers the perfect blend of historic character and modern convenience. Step inside and you are immediately welcomed by the large foyer,

  Joshua Lemieux Remax Summit

  160 Depot St, Chester, VT 05143
• 

  

  /10

  $150,000 Sold Mar 07, 2025

  • Land
  • 10 Acres
  • $14,735 per Acre

  • 468 Days On Market

  0 Spruce Dr Unit 4973323, Andover, VT 05143

  Nestled in the picturesque town of Andover, Vermont, this remarkable 10+ acre parcel of land offers an unparalleled opportunity to create your dream retreat amidst the tranquility of nature. Located on a quiet country road, this parcel is a blank canvas for your vision of a rustic escape. An easy commute to the towns of Chester, Ludlow, and Londonderry for shopping, restaurants, and exploring,

  Alan DeAngelo Element Real Estate

  0 Spruce Dr Unit 4973323, Andover, VT 05143
• 

  

  /40

  Est $1,253,821 Not Listed For Sale

  • 7 Beds
  • 6 Baths
  • 5,566 Sq Ft

  683 Church St, Chester, VT 05143

  683 Church St, Chester, VT 05143
• 

  

  /29

  $275,000

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft

  81 Trombley Rd, Andover, VT 05143

  This beautiful privately located 3 bedroom, 2 bathroom manufactured home is move in ready and just waiting for your finishing touches! It has a wonderful level yard with plenty of space for gardens, room to play, or put in a camp fire to sit around on a lovely Vermont evening. There is an additional gravel pad in place that you could put a tiny home as a rental opportunity or a guest house when

  Erin Kendall EXP Realty

  81 Trombley Rd, Andover, VT 05143
• 

  

  /30

  $210,000 Sold Feb 12, 2025

  • 1,332 Sq Ft
  • $158/SF
  • 26 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1950

  41 Miller Rd, Putney, VT 05346

  Unique Contemporary design seasonal cottage on 10.1 acres in a private serene location at the end of an old road. The central octagon portion of the building contains the spacious kitchen and a large open concept living/dining room with woodstove. This large south-facing room has a slider that opens into a small patio area overlooking the immense front lawn. To the east and west are 2 wings off

  Steve Schoppmeyer BHG Masiello Brattleboro

  41 Miller Rd, Putney, VT 05346
• 

  

  /40

  Est $683,388 Not Listed For Sale

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

  604 Church St, Chester, VT 05143

  604 Church St, Chester, VT 05143
• 

  

  /15

  $129,000

  • Land
  • 3.24 Acres
  • $39,815 per Acre

  Lot 3 Mattson Rd, Chester, VT 05143

  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 hillside that levels out

  Jessica Citera Cummings & Co

  Lot 3 Mattson Rd, Chester, VT 05143
• 

  

  /26

  $270,000 Sold Feb 05, 2025

  • 1,005 Sq Ft
  • $269/SF
  • 0 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1988

  203 Marcs Dr, Chester, VT 05143

  Escape to this charming log cabin, tucked away on a quiet dead-end road. With an attached two-car garage and a small horse barn, this property is perfect for those seeking a blend of rustic charm and practicality. Inside, you’ll find a thoughtfully designed two-bedroom, one-bathroom layout with an airy open floor plan. The kitchen and living room flow seamlessly together, centered around a wood

  Sarah Sheehan William Raveis Real Estate Vermont Properties

  203 Marcs Dr, Chester, VT 05143
• 

  

  /19

  Est $249,958 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,080 Sq Ft

  45 Dalrymple St, Chester, VT 05143

  45 Dalrymple St, Chester, VT 05143
• 

  

  /30

  $650,000

  • 3 Beds
  • 3 Baths
  • 4,324 Sq Ft

  3630 Vt Route 103 N, Chester, VT 05143

  Exceptional Investment Opportunity in Chester, VTDiscover this stunning, completely renovated property that beautifully combines modern amenities with unique character. Featuring two residential units. This home showcases high-quality upgrades throughout. Enjoy peace of mind with new electrical, plumbing, insulation, and energy-efficient windows. The kitchens and bathrooms have been

  Gary Coger Four Seasons Sotheby's Int'l Realty

  3630 Vt Route 103 N, Chester, VT 05143
• 

  

  /53

  $499,000 Sold Feb 03, 2025

  • 2,650 Sq Ft
  • $188/SF
  • 229 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1820

  566 Simonsville Rd, Chester, VT 05143

  The historic Jaquith House is located in the Andover settlement of Simonsville on Rte 11. This historical brick federal 3 bedroom, 2.5 bath home on 6.85 +/- acres has potential for either a vacation home with guest house, year round residence or investment property. The two story double-walled brick home has original features such as eyebrow windows and 3 chimneys and has been thoughtfully

  Geralyn Donohue Engel & Völkers Okemo

  566 Simonsville Rd, Chester, VT 05143
• 

  

  /39

  Est $374,834 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,990 Sq Ft

  401 North St, Chester, VT 05143

  401 North St, Chester, VT 05143
• 

  

  /29

  $399,000

  • 4 Beds
  • 3.5 Baths
  • 2,710 Sq Ft

  491 Farrar Rd, Chester, VT 05143

  Tucked away on a quiet dirt road, this spacious sunny south-facing home offers a peaceful retreat with sweeping views of the surrounding countryside. Step onto the expansive front deck and take in the stunning long-range scenery, including a picturesque pond just beyond the property—yours to enjoy without the upkeep.Inside, the home is open and inviting, with plenty of room to relax or

  Daire Gibney Barrett and Valley Associates Inc.

  491 Farrar Rd, Chester, VT 05143
• 

  

  /5

  $22,000 Sold Jan 31, 2025

  • Land
  • 3.28 Acres
  • $6,707 per Acre

  • 211 Days On Market

  0 Remington Rd Unit 9 4997325, Chester, VT 05143

  REUCDUED OVER $10,000.00, PRICED TO SELL! Lot #9 is one of the larger lots in the lower subdivision. It includes a pond that is maintained by the association with a fire hydrant to reduce insurance costs. Roughed in driveway and cleared building site make this a breeze to start construction. The lot is terraced with a nice buffer of trees for privacy. Come take a look today! PLEASE NOTE THERE

  Frank Provance Diamond Realty

  0 Remington Rd Unit 9 4997325, Chester, VT 05143
• 

  

  /28

  Est $413,274 Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 2,152 Sq Ft

  250 North St, Chester, VT 05143

  250 North St, Chester, VT 05143
• 

  

  /11

  $119,000

  • Land
  • 16 Acres
  • $7,589 per Acre

  00 E Hill Rd, Andover, VT 05143

  Rooted in along scenic East Hill Road in the bucolic town of Andover, this 16-acre parcel offers a rare opportunity to create your own private haven in one of Southern Vermont’s most peaceful and charming settings. Just minutes from Ludlow and the slopes of Okemo Mountain, this location strikes the perfect balance between quiet countryside and convenient access to skiing, shopping, dining, and

  Daire Gibney Barrett and Valley Associates Inc.

  00 E Hill Rd, Andover, VT 05143
• 

  

  /6

  $23,000 Sold Jan 31, 2025

  • Land
  • 1.64 Acres
  • $14,024 per Acre

  • 215 Days On Market

  0 Remington Rd Unit 8 4996410, Chester, VT 05143

  REUCDUED $10,000.00 PRICED TO SELL! Just a mile to the quintessential downtown of Chester is this beautiful lot in the Remington subdivision. This 1.64 acre lot has exceptional views! The terraced lot is ideal for a walk out lower level to a what could be a flat lush lawn with fire pit, swing set, horseshoe pits or all of the above! This is a great value with a million dollar view! Under

  Frank Provance Diamond Realty

  0 Remington Rd Unit 8 4996410, Chester, VT 05143
• 

  

  /39

  Est $371,430 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 2,090 Sq Ft

  312 North St, Chester, VT 05143

  312 North St, Chester, VT 05143
• 

  

  /5

  $80,000

  • Land
  • 4.30 Acres
  • $18,605 per Acre

  00 N Hill Rd, Andover, VT 05143

  The first step in building your Vermont Dream home is finding the perfect piece of land. Look no further! Situated on quiet country road of North Hill this parcel offers great building site, quiet location, easy access to skiing at Vail/Okemo resort (only minutes away), VAST access, close to Weston village with the Vermont Country Store and the Weston Playhouse. Soil tests were conducted years

  Lisa Kelley Cummings & Co

  00 N Hill Rd, Andover, VT 05143
• 

  

  /5

  $20,000 Sold Jan 30, 2025

  • Land
  • 1.34 Acres
  • $14,925 per Acre

  • 207 Days On Market

  0 Remington Rd Unit 6 4996522, Chester, VT 05143

  REUCDUED ALMOST $10,000.00, PRICED TO SELL! This affordable lot has under ground power and a permitted inground septic design. Ready for you and your home plans. Just minutes to the Chester Green and an array of outdoor activities to include world class skiing at several different ski areas. PLEASE NOTE THERE IS A MINIMUM OF 1,800 Sq Ft Of Finished Living Space.

  Frank Provance Diamond Realty

  0 Remington Rd Unit 6 4996522, Chester, VT 05143
• 

  

  /37

  Est $679,415 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,325 Sq Ft

  332 Marcs Dr, Chester, VT 05143

  332 Marcs Dr, Chester, VT 05143
• 

  

  /34

  $355,000

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

  847 Simonsville Rd, Andover, VT 05143

  Come find your own peaceful piece of the Vermont countryside in the beautiful town of Andover. Look no further than this move in ready homestead on 51.2 rolling acres with two large paddocks fenced and ready waiting for your animals, complete with two spacious sheds, and a chicken coop ready to house them. Established asparagus patch, blueberry bushes, apple trees, and even your own cranberry bog

  Erin Kendall EXP Realty

  847 Simonsville Rd, Andover, VT 05143
• 

  

  /60

  $975,000 Sold Jan 24, 2025

  • 3,704 Sq Ft
  • $263/SF
  • 8 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2004

  1062 Andover Ridge Rd, Andover, VT 05143

  Welcome to 1062 Andover Ridge where you can buy a million-dollar view and get a gorgeous log home to go with it. The views are breathtaking and can be enjoyed from almost every room as well as the deck from either in or out of the 6-person hot tub. The recently renovated exterior and kitchen make this a perfect Vermont dream home. High-end stainless appliances, soapstone kitchen island, massive

  Kevin Barnes William Raveis Real Estate Vermont Properties

  1062 Andover Ridge Rd, Andover, VT 05143
• 

  

  /40

  Est $597,625 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,564 Sq Ft

  498 Marcs Dr, Chester, VT 05143

  498 Marcs Dr, Chester, VT 05143
• 

  

  /14

  $259,000

  • Land
  • 9 Acres
  • $30,363 per Acre

  224 Arrau Rd, Andover, VT 05143

  If you're searching for a slice of paradise, look no further than this Hidden Gem. Nestled in the heart of Vermont’s picturesque Green Mountains, this Andover lot offers everything you’ve been dreaming of. With the perfect blend of privacy and convenience, you’ll find peace and quiet paired with a short drive from the charming towns of Ludlow, Weston, Chester, and Londonderry. Spanning 8.53

  Thaddeus Abare Barrett and Valley Associates Inc.

  224 Arrau Rd, Andover, VT 05143
• 

  

  /33

  $210,000 Sold Jan 21, 2025

  • 2,736 Sq Ft
  • $77/SF
  • 47 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2022

  110 Shady Grove Ln, Chester, VT 05143

  Located on private road on Shady Grove Lane, this newly constructed 2.5 story 2 bedroom, 2 bath home on 5.12 +/- acres has been framed. The first floor layout includes a large kitchen/living area with a bedroom and full bath. The second floor includes a full bath with large bedroom. This beautiful home includes a walkout basement. All building materials on site are included with the sale. This

  Rob Weltz Barrett & Valley Assoc. Inc

  110 Shady Grove Ln, Chester, VT 05143
• 

  

  /10

  Est $353,044 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,214 Sq Ft

  784 Vt Route 103 N, Chester, VT 05143

  784 Vt Route 103 N, Chester, VT 05143
• 

  

  /23

  $69,000

  • Land
  • 2.86 Acres
  • $24,126 per Acre

  58 Remington Rd, Chester, VT 05143

  Building lot with driveway and culverts in place, lot has preliminary site work complete including level grass land area, electrical transformer and 100 amp electrical power plus VTel fiber internet on lot for your new Vermont home. Home must be a minimun of 1,800 square feet of finished living space. Wastewater design and permits in place. A 16' x 25' garage/shed on lot for storage while

  John Napier TPW Real Estate

  58 Remington Rd, Chester, VT 05143
• 

  

  /6

  $60,000 Sold Jan 21, 2025

  • Land
  • 14 Acres
  • $4,383 per Acre

  • 98 Days On Market

  0 Whitmore Brook Rd, Chester, VT 05143

  This four lot subdivision is a builders dream. The abutting house took two of the lots for a buffer. Two remaining subdivided lots come complete with state permits for waste water and septic designs. Come take a look and bring your plans. These lots average less than $35k per lot.

  Frank Provance Diamond Realty

  0 Whitmore Brook Rd, Chester, VT 05143

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