Windsor, VT Homes

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  /29

  Est $562,636 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,675 Sq Ft

  237 Divoll Pasture Rd, Springfield, VT 05156

  237 Divoll Pasture Rd, Springfield, VT 05156
• 

  

  

  /31

  $379,900

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

  34 Fox Chair Terrace, Springfield, VT 05156

  Welcome to 34 Fox Chair Terrace, a peaceful, private three-bedroom, two-bath home set on a full acre just minutes from downtown Springfield and charming Chester, Vermont. Tucked away in a quiet rural setting, this spacious property offers the best of both worlds: privacy and nature, with easy access to shopping, schools, the local hospital, and other area amenities.Step inside to find a

  Patrick Kelley Four Seasons Sotheby's Int'l Realty

  34 Fox Chair Terrace, Springfield, VT 05156
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  /2

  $195,000 Sold Jul 10, 2025

  • 1,663 Sq Ft
  • $117/SF
  • 213 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1933

  271 Cragiue Hill Rd, Springfield, VT 05156

  Welcome to this charming 2-bedroom, 2-bathroom Cape-style home, offering a perfect blend of comfort and functionality. As you enter, you’ll be greeted by a warm, inviting living area with a pellet stove that leads to the kitchen, ideal for preparing family meals and entertaining guests. The main level features a full bathroom, while the second level boasts the two official bedrooms and the

  Thaddeus Abare Barrett and Valley Associates Inc.

  271 Cragiue Hill Rd, Springfield, VT 05156
• 

  

  

  /28

  Est $501,533 Not Listed For Sale

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

  1376 Skyline Dr, Springfield, VT 05156

  1376 Skyline Dr, Springfield, VT 05156
• 

  

  

  /49

  $450,000

  • 4 Beds
  • 2 Baths
  • 2,040 Sq Ft

  281 Evergreen Terrace, Springfield, VT 05156

  This delightful home is sure to please. Set in a lovely wooded cul-de-sac, surround yourself with lovely, terraced landscaping, stone walls and a peaceful wooded setting to while away the hours. This beautiful well cared home features many delightful settings. The living room features a cathedral ceiling and stone fireplace, with a wood stove insert, along with many windows to bring in the

  Carol Cole BHG Masiello Brattleboro

  281 Evergreen Terrace, Springfield, VT 05156
• 

  /2

  $172,000 Sold Jul 08, 2025

  • 1,300 Sq Ft
  • $132/SF
  • 125 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1900

  416 Giddings St, Springfield, VT 05150

  This home exudes the ultimate Bohemian charm—the New England version of Venice—overlooking the tranquil, babbling Great Brook. The beautifully landscaped yard bursts with vibrant perennial flowers, while the fenced-in space, complete with a firepit and a scenic water-view deck, offers endless spots to relax and unwind. Inside, the thoughtfully designed circular layout is bathed in natural light,

  Chelsea Richardson Barrett and Valley Associates Inc.

  416 Giddings St, Springfield, VT 05150
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  /18

  Est $333,740 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  1098 Roberts Rd, Springfield, VT 05156

  1098 Roberts Rd, Springfield, VT 05156
• 

  

  /34

  $375,000

  • 4 Beds
  • 2 Baths
  • 1,300 Sq Ft

  12 Meadow Dr, Springfield, VT 05156

  This delightful ranch home located in a desirable cul-de-sac neighborhood, is where you can enjoy a nice evening walk and chat with the neighbors. Enter from the front porch to the bright living room with a lovely fireplace and hardwood floors, to enjoy a fire on those cool evenings. The nice sized kitchen adjoins the lovely dining room which features easy access to the large screened-in porch,

  Carol Cole BHG Masiello Brattleboro

  12 Meadow Dr, Springfield, VT 05156
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  /28

  $197,700 Sold Jul 07, 2025

  • 640 Sq Ft
  • $309/SF
  • 47 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1941

  93 Litchfield St, Springfield, VT 05156

  Charming and thoughtfully updated, this 2-bedroom, 1-bath bungalow is nestled in a prime location on Litchfield Street. With woods across the road and a spacious back deck overlooking the 5-Mile Stream, this home offers both some privacy and convenience - just minutes from town and a short walk to Elm Hill School. Extensively renovated in 2021 - 2022, the home features a new roof, cedar siding,

  Debra Staniscia Four Seasons Sotheby's Int'l Realty

  93 Litchfield St, Springfield, VT 05156
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  /34

  Est $178,270 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,358 Sq Ft

  364 South St, Springfield, VT 05156

  364 South St, Springfield, VT 05156
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  /42

  $424,900

  • 3 Beds
  • 2 Baths
  • 2,776 Sq Ft

  64 Summer Hill St, Springfield, VT 05156

  Tucked in one of Springfield’s most sought-after neighborhoods, 64 Summer Hill St offers the perfect blend of comfort, charm, and convenience. This beautifully maintained 3-bedroom, 2-bath home nestled in one of Springfield’s most desirable neighborhoods. Located on a peaceful .28acre lot in the Cherry Hill district, this inviting property offers the perfect balance of comfort and convenience.

  Jamie Watson BHG Masiello Keene

  64 Summer Hill St, Springfield, VT 05156
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  /21

  $235,000 Sold Jul 05, 2025

  • 1,248 Sq Ft
  • $188/SF
  • 14 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1986

  42 Melody Ln, Springfield, VT 05156

  ~Price adjustment~Sellers say it is time to move on to the next chapter. Don't miss out on this amazing opportunity!Welcome Home to Country Charm and Modern ComfortNestled on a picturesque 1.7-acre lot in the village of Weathersfield, this beautifully updated manufactured home offers the perfect blend of comfort, style, and outdoor living.Step inside to discover a

  Linda Benoit Highland Realty

  42 Melody Ln, Springfield, VT 05156
• 

  

  /17

  Est $252,961 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft

  5 Canary Ct, Springfield, VT 05156

  5 Canary Ct, Springfield, VT 05156
• 

  

  /40

  $335,000 Pending

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

  91 Fairground Rd, Springfield, VT 05156

  This well-maintained one-level-living home with gorgeous hardwood floors located in a family neighborhood is ready for new owners! It's clean, vacant, and turn-key. Situated on a large, open lot, you'll have plenty of space to enjoy the outdoors. A brand new septic system will be installed, to begin work mid July. The Seller recently finished off a portion of the lower level to offer more living

  Heather Gleim CENTURY 21 North East

  91 Fairground Rd, Springfield, VT 05156
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  /29

  $185,000 Sold Jun 25, 2025

  • 1,130 Sq Ft
  • $164/SF
  • 5 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1930

  120 South St, Springfield, VT 05156

  Nestled conveniently off Main Street in Springfield, Vermont, this charming 3-bedroom, 1-bathroom home offers effortless access to downtown's vibrant amenities, restaurants, and the local school district. Step inside to a welcoming entryway, perfect for storing outdoor gear, and discover a spacious kitchen boasting ample cabinet space and direct access to an unfinished basement with laundry. The

  Daniel Preston KW Vermont Woodstock

  120 South St, Springfield, VT 05156
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  /4

  Est $230,591 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 810 Sq Ft

  9 Canary Ct, Springfield, VT 05156

  9 Canary Ct, Springfield, VT 05156
• 

  

  /35

  $319,900 Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,144 Sq Ft

  103 French Meadow Rd, Springfield, VT 05156

  Off a peaceful road in the wonderful town of Springfield, VT sits a beautifully maintained 3-bedroom, 1.5-bath ranch nestled on a peaceful and private 2-acre lot. This easy-living home features freshly sanded hardwood floors throughout, offering a warm and timeless feel in every room. Enjoy the simplicity of single-level living with an efficient layout and low-maintenance design. The full

  Jamie Watson BHG Masiello Keene

  103 French Meadow Rd, Springfield, VT 05156
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  /38

  $400,000 Sold Jun 20, 2025

  • 2,856 Sq Ft
  • $140/SF
  • 64 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1982

  73 Walnut Hill Rd, Springfield, VT 05156

  Ready for you to simply unpack and enjoy, this meticulously maintained, single-owner home offers a lifestyle of comfort, convenience, and privacy. Designed for ease and practicality, the single-floor living layout provides seamless flow and accessibility. Whether you enjoy privacy or entertaining friends, the versatile space adapts effortlessly to your needs. On cooler evenings, cozy up to the

  Jill Lawrence The Real Estate Collaborative

  73 Walnut Hill Rd, Springfield, VT 05156
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  /35

  Est $301,990 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,655 Sq Ft

  350 South St, Springfield, VT 05156

  350 South St, Springfield, VT 05156
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  /45

  $350,000 Under Contract

  • 4 Beds
  • 2 Baths
  • 1,566 Sq Ft

  47 Dell Rd, Springfield, VT 05156

  Welcome to a home that truly has it all! Perfectly positioned on a cul-de-sac, this property is steps away from the trailhead of Hartness Park where you can enjoy 3 miles of trails in the 85 acre town forest. A seamless blend of privacy whilst still being in town - what more can you ask for? This beautifully maintained property offers the rare and coveted convenience of first-floor living—with

  Taylor Medeiros-Batey KW Coastal and Lakes & Mountains Realty/Hanover

  47 Dell Rd, Springfield, VT 05156
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  /36

  $317,000 Sold Jun 18, 2025

  • 1,872 Sq Ft
  • $169/SF
  • 63 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1983

  137 Grover Rd, Springfield, VT 05156

  End of the road privacy, stunning long range views, 15 acres! The first level of this two-story colonial home features two bedrooms (one with an attached dressing area or office nook) and a 3/4 bathroom with a step-in shower. All utilities are also conveniently located on this level for easy access. Take the spiral staircase to the second floor, where the living space is designed to maximize your

  Rebecca Seymour Brattleboro Area Realty

  137 Grover Rd, Springfield, VT 05156
• 

  

  /33

  Est $233,409 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,810 Sq Ft

  342 South St, Springfield, VT 05156

  342 South St, Springfield, VT 05156
• 

  

  /25

  $195,000

  • 2 Beds
  • 1 Bath
  • 1,152 Sq Ft

  15 Randall St, Springfield, VT 05156

  Nestled near the end of a quiet dead-end road, this Cape-style home offers both tranquility and convenience. Featuring beautiful oak hardwood floors, this property is filled with character and potential. The spacious deck invites you to enjoy outdoor living, while the attached 2-car garage adds both practicality and ease. Inside, the main level boasts a formal dining room, a cozy living room, and

  Chelsea Richardson Barrett and Valley Associates Inc.

  15 Randall St, Springfield, VT 05156
• 

  

  /19

  $25,104 Sold Jun 13, 2025

  • 728 Sq Ft
  • $34/SF
  • 45 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 2024

  141 Ash Ln, Springfield, VT 05156

  Welcome to 41 Ash Lane, Springfield VT 05156, where modern comfort meets affordability in Windy Hill Acres Park! This brand-new 2017 Redman 1448 Northwoods model manufactured home offers 2 bedrooms, 1 bathroom, and 728 sq. ft. of thoughtfully designed living space.Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features

  Kate Barry EXP Realty

  141 Ash Ln, Springfield, VT 05156
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  /27

  Est $245,450 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,124 Sq Ft

  308 South St, Springfield, VT 05156

  308 South St, Springfield, VT 05156
• 

  

  /34

  $275,000

  • 4 Beds
  • 1.5 Baths
  • 1,616 Sq Ft

  10 Derby Ct, Springfield, VT 05156

  This bright and inviting Gambrel home sits on a corner lot and offers a lovely, fenced backyard, to grow your garden, or play toss with the kids. This home features a welcoming, large foyer, a generous living room and a formal dining room for those family dinners. The kitchen features an island to enjoy the morning coffee. With four bedrooms 1 full bathroom and one 1.4 baths, there is plenty of

  Carol Cole BHG Masiello Brattleboro

  10 Derby Ct, Springfield, VT 05156
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  /54

  $685,000 Sold Jun 10, 2025

  • 2,583 Sq Ft
  • $265/SF
  • 46 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2003

  730 Parker Hill Rd, Springfield, VT 05156

  Journey down one of Springfield's most scenic roads to discover this serene retreat, nestled among stately sugar maples and offering breathtaking 180-degree views. Completed in 2004, this meticulously maintained three-bedroom, two-bath reproduction farmhouse offers ~2,600 square feet of light-filled living space. The bright kitchen with a cozy sitting area flows into the beautiful formal dining

  Debra Staniscia Four Seasons Sotheby's Int'l Realty

  730 Parker Hill Rd, Springfield, VT 05156
• 

  

  /28

  Est $321,131 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,754 Sq Ft

  167 Stanley Rd, Springfield, VT 05156

  167 Stanley Rd, Springfield, VT 05156
• 

  

  /13

  $220,000

  • 5 Beds
  • 3 Baths
  • 2,655 Sq Ft

  30 Union St, Springfield, VT 05156

  Well maintained 3plex located in a desirable quaint residential Springfield neighborhood with a NOI of over $28,000 and listed at over a 12%+ cap rate. This property features a desirable mix of spacious 2x2br/1ba and 1x1br/1ba, and a 5 car driveway. This building has been recently renovated and updated, and is 100% occupied. Current gross income is north of $44,000A new owner can step

  Michael Gilman 3GEN Real Estate Inc

  30 Union St, Springfield, VT 05156
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  /2

  $271,000 Sold Jun 06, 2025

  • 3,198 Sq Ft
  • $85/SF
  • 55 Days On Market

  • Built 1886

  30 Pearl St, Springfield, VT 05156

  Prime Multi-Family Investment Opportunity in Springfield! With the recent annoucment of a $10mm develpment of the nearby hospial and mill builing complex you wont want to miss this exceptional income property near downtown Springfield, perfect for investors seeking both profitability and location this is up and coming Vermont Town. This three-unit building combines modern updates with

  Daire Gibney Barrett and Valley Associates Inc.

  30 Pearl St, Springfield, VT 05156
• 

  

  /16

  Est $194,218 Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 1,878 Sq Ft

  151 South St, Springfield, VT 05156

  151 South St, Springfield, VT 05156
• 

  

  /48

  $200,000

  • 3 Beds
  • 1 Bath
  • 1,556 Sq Ft

  234 Harvard St, Springfield, VT 05156

  Discover timeless charm & everyday comfort in the heart of Springfield with this inviting home, where classic character meets modern ease. From the whimsical stucco exterior and detached two-car garage (currently set up as a workshop) to the one-of-a-kind walrus-shaped mailbox - this home is full of personality. Step inside to discover hardwood floors, natural light, & flexible layout that suits

  Isabella Luhrs BHG Masiello Keene

  234 Harvard St, Springfield, VT 05156
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  /30

  $462,750 Sold Jun 05, 2025

  • 1,388 Sq Ft
  • $333/SF
  • 54 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1968

  150 Barlow Rd, Springfield, VT 05156

  Imagine coming home to this meticulously maintained one owner home located in the heart of rural Springfield, Vermont farm country. The home is situated on a mostly open, manicured 4-acre parcel with a half-acre pond where you will frequently find waterfowl swimming. Outstanding mountain views in the distance can be enjoyed from inside or from the deck overlooking the yard and pond. Hardwood

  Julie Buffum Buffum Realty

  150 Barlow Rd, Springfield, VT 05156
• 

  

  /11

  Est $184,459 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  200 Commonwealth Ave, Springfield, VT 05156

  200 Commonwealth Ave, Springfield, VT 05156
• 

  

  /8

  $169,000

  • 4 Beds
  • 1 Bath
  • 1,746 Sq Ft

  7 Berry Rd, Springfield, VT 05150

  Spacious Home in a Peaceful Setting – Finish to Your TasteTucked away in a quiet location, this large home offers a great opportunity for someone ready to roll up their sleeves and complete the work that’s already well underway. Many major updates have been started, and plenty of supplies are already on site and included with the sale—saving you time and money.What’s

  Linda Benoit Highland Realty

  7 Berry Rd, Springfield, VT 05150
• 

  

  /25

  $195,000 Sold Jun 05, 2025

  • 1,284 Sq Ft
  • $152/SF
  • 61 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1940

  52 Litchfield St, Springfield, VT 05156

  Situated on a quiet street in a family neighborhood, this sweet home has lots to offer! There are three bedrooms and one bath, with one of the bedrooms located on the first floor. Many improvements including new replacement windows, a new water heater in 2021, a new oil tank in 2020, and a new roof in 2016. In the winter you'll appreciate storing your car in the garage, and in the warmer months

  Heather Gleim CENTURY 21 North East

  52 Litchfield St, Springfield, VT 05156
• 

  

  /27

  Est $259,077 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,680 Sq Ft

  129 Commonwealth Ave, Springfield, VT 05156

  129 Commonwealth Ave, Springfield, VT 05156
• 

  

  /52

  $599,900

  • 4 Beds
  • 3.5 Baths
  • 2,068 Sq Ft

  266 Barlow Rd, Springfield, VT 05156

  This beautiful property has so much to offer! This extremely well maintained home is both private and serene, tucked away on top of the world. Outside the home features, a large back deck, standing seam roof, expansive space for gardens and the privacy of 33.19+/- acres. Going inside the home features full picture windows allowing plenty of natural light, two Gas fireplaces perfect for

  Thaddeus Abare Barrett and Valley Associates Inc.

  266 Barlow Rd, Springfield, VT 05156
• 

  

  /13

  $80,000 Sold Jun 05, 2025

  • 556 Sq Ft
  • $144/SF
  • 166 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1940

  64 County Rd, North Springfield, VT 05150

  BACK ON THE MARKET AT NO FAULT OF THE PROPERTY. Older cottage in need of a total re-hab is waiting for you. Would make a great vacation home or seasonal home or a cute little home for one or two people. Standing seam roof, built on an accessible crawl space. There is an old barn on the property for storage as well. This home will NOT qualify for financing, so we are looking for a cash buyer

  Julie Buffum Buffum Realty

  64 County Rd, North Springfield, VT 05150
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  /40

  Est $208,362 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,233 Sq Ft

  70 Olive St, Springfield, VT 05156

  70 Olive St, Springfield, VT 05156

Showing Results 41 - 80, Page 2 of 18