Windsor County VT Homes under $300,000

/30
$229,000
- 3 Beds
- 2 Baths
- 1,792 Sq Ft
95 Union St, Springfield, VT 05156

Large home on generously sized lot with lots of room to romp this 3BR/2BA home has lots of space indoors and out. Roomy and sun filled kitchen flows right into the dining room. Living room is cozy with the pellet stove glowing. Good sized mud room could be used as a small office or reading room or a place to do homework. 1st floor full bath and laundry for your convenience. 2nd floor has a

Julie Buffum

Buffum Realty

(802) 644-3166

95 Union St, Springfield, VT 05156
/14
$230,000
- Land
- 6 Acres
- $36,918 per Acre
1090 New Boston Rd, Norwich, VT 05055

Build your dream home on the hill of this sunny 6.23 acre parcel in Norwich. A building site has been cleared for the highest point of the property with a view. An engineer has completed a wetlands study and an application is ready to be submitted for approvals. There is a camp on the property in need of a septic, should you keep it. Just minutes from Dartmouth College and the Upper Valley.

Melissa Robinson

Coldwell Banker LIFESTYLES - Hanover

(802) 808-6490

1090 New Boston Rd, Norwich, VT 05055
/45
$275,000
- 2 Beds
- 1 Bath
- 972 Sq Ft
10 Clark St, North Springfield, VT 05150

Delightful light filled ranch home with a touch of whimsy and country mixed to make this home a happy spot to be. Walk into the large finished and heated breezeway, a great place to sit a spell or use as a mud room. Access to the breezeway from front, back and the garage to make this a very convenient and usable space. This home features a large kitchen with room for a table, stainless steel

Julie Buffum

Buffum Realty

(802) 520-2725

10 Clark St, North Springfield, VT 05150
/15
$237,000
- Land
- 221 Acres
- $1,072 per Acre
0 New Boston Rd, Thetford, VT 05074

IntroductionThe ownership is selling their property in two separate parcels, divided by the town line. The +/-60 acre Strafford parcel is well suited to future home development with paved town road frontage and roadside electric service. The +/-220 acre Thetford parcel is well suited to a camp or seasonal off-grid home development with beautiful local views.Both parcels have

John Latham Fountains Land

0 New Boston Rd, Thetford, VT 05074
/39
$275,000
- 3 Beds
- 2 Baths
- 1,785 Sq Ft
36 Graham St, Bethel, VT 05032

Tucked away on a quiet street just off Route 107, this 3-bedroom, 2-bath home offers a great mix of privacy, practicality, and convenience in the heart of Bethel. Inside, you'll find a functional layout with a spacious laundry room, a recently installed dishwasher, and a pellet stove that efficiently heats the entire home, with oil radiator heat as a backup option. The detached two-car garage

Jacob Barnes EXP Realty

36 Graham St, Bethel, VT 05032
/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
/24
$289,000
- 3 Beds
- 2 Baths
- 1,890 Sq Ft
89 Lyon Rd, South Royalton, VT 05068

A perfect ‘SoRo’ location, minutes from the charm of South Royalton Village and privacy off a dead -end road, make this country property a must see. The 2000+/- sqft of living space includes a large kitchen/family room, functional mudroom, office/study, large bedrooms, and two storage sheds on property. In warmer months, the large front deck provides additional living and entertaining space.

Seth Barbiero EXP Realty

89 Lyon Rd, South Royalton, VT 05068
/29
$299,000
- 5 Beds
- 3.5 Baths
- 3,465 Sq Ft
600 N Windsor St, South Royalton, VT 05068

Just 3⁄4 of a mile from the heart of South Royalton and Vermont Law School, this versatile property offers tremendous rental potential with some TLC. With three separate units—each with its own private entrance—this is the perfect opportunity to renovate and generate strong rental income. The main unit in the house has 3 bedrooms and 1 1/2 baths. The second unit in the main house is a 1 bed 1

Franchesca Collins Hall Collins Real Estate Group

600 N Windsor St, South Royalton, VT 05068
/22
$275,000
- 2 Beds
- 2 Baths
- 790 Sq Ft
32 Pond St Unit 2, Ludlow, VT 05149

This is a versatile remodeled and completely move-in ready condo. This two bedroom, two bath condominium is within walking distance to Main Street. The condo has an interior privacy door that can close off a bedroom with private bath and a kitchenette allowing both sides to be used/rented separately as two -1 bedrooms condos spaces. There are two exterior ski lockers and two parking spaces. This

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

32 Pond St Unit 2, Ludlow, VT 05149
/60
$265,000
- 2 Beds
- 1 Bath
- 1,076 Sq Ft
643 Vermont 12, Hartland, VT 05048

** PRICE REDUCTION** Charming and affordable home on a level 1-acre lot with open yard lined with mature trees and a serene wooded backdrop. This expanded ranch offers 2 bedrooms and 1 full bath, with a practical layout including first-floor laundry and a spacious second-floor bedroom addition. Originally built in 1940 with an upstairs expansion in the 1980s, the home features a drilled well,

John Bassette Bassette Real Estate Group

643 Vermont 12, Hartland, VT 05048
/41
$259,000
- 2 Beds
- 1 Bath
- 880 Sq Ft
574 Willard Rd Unit 1A, Quechee, VT 05059

Beautifully reimagined Quechee Hollow end unit! The community pond is right outside of your front door. Meticulously transformed with new kitchen, bath, appliances, Anderson windows and exterior doors. This is a great price point for access to the Quechee Lakes Community and all of its amenities! Golf, tennis, pickleball, gym, indoor and outdoor pools, skiing, dining and access to Lake Pinneo are

Mark Roden KW Coastal and Lakes & Mountains Realty/Hanover

574 Willard Rd Unit 1A, Quechee, VT 05059
/8
$300,000
- Land
- 55 Acres
- $5,415 per Acre
452 Morse Rd, Bethel, VT 05032

Seldom does a parcel of this quality come onto the open market. Hay fields offering south facing views, 1/2 mile of gravel Town road frontage, and bounded by the Second Branch of the White River. About half of the land is open with the balance being mixed woodland. Truly a spectacular property located on the Bethel/Royalton Town line, convenient to I-89, exit 3.

Dean Goulet Dunrovin Real Estate

452 Morse Rd, Bethel, VT 05032
/29
$209,999
- 3 Beds
- 2 Baths
- 1,120 Sq Ft
9 Stryhas Trailer Ct, Ludlow, VT 05149

Charming and well-maintained 3-bedroom, 2-bathroom manufactured home in a peaceful 55+ community. This inviting home features an open concept layout, high ceilings, and is filled with natural light pouring in through multiple skylights, creating a bright and airy atmosphere. Step outside to a new deck with an awning—perfect for enjoying warm summer days.The fenced yard is great for pets

Gabrielle Turco Kelley Real Estate, Inc.

9 Stryhas Trailer Ct, Ludlow, VT 05149
/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
/28
$249,000
- 1 Bed
- 1 Bath
- 816 Sq Ft
42 Heritage Condo Way Unit 16, Woodstock, VT 05091

OPEN HOUSE SAT AUG 2 FROM 10 - 12 Located less than 2 miles from the Woodstock Village Green, this immaculately maintained and move-in-ready condo offers comfort and convenience in a peaceful setting. Just eight steps down from the front foyer, the unit opens into a thoughtfully designed space ideal for single-level living.Inside, you’ll find laminate flooring throughout and a cozy

Franchesca Collins Hall Collins Real Estate Group

42 Heritage Condo Way Unit 16, Woodstock, VT 05091
/40
$219,000
- 2 Beds
- 2 Baths
- 1,420 Sq Ft
396 S Main St, Bethel, VT 05032

Just minutes from downtown Bethel this home has everything you’re looking for! The sunny, gently sloping yard is ideal for gardening, or hosting gatherings.Inside, you'll find two bedrooms and two full bathrooms, a spacious living room, and a bright kitchen that opens to a large dining room with sliding doors leading to a private deck overlooking the backyard.Both bedrooms are

Lindsay Cimadon

396 S Main St, Bethel, VT 05032
/14
$249,000
- Land
- 6 Acres
- $38,308 per Acre
5518 Vt Route 12, Barnard, VT 05031

A pastoral parcel of land with the benefit a truly mesmerizing private pond! The location is great! Recreation on pristine Silver Lake and shopping in the beloved Barnard General Store are just a few minutes away from this peaceful Barnard Village acreage! One obvious building site would take advantage of views of the pond. Other possible sites certainly are presented within the extended open

John Wetmore Wetmore Real Estate

5518 Vt Route 12, Barnard, VT 05031
/60
$200,000
- Land
- 7 Acres
- $30,166 per Acre
00 Vermont 103, Andover, VT 05143

Tucked just off scenic Route 103 in charming Chester, this parcel offers a prime opportunity to create your own Vermont retreat. With aproposed well and septic design already in place, much of the groundwork has been done—now it's your turn to bring the vision to life. The lot offersample space for parking and potential for mountain or woodland views with some strategic tree clearing. Whether

Rachael Rogala Rachael Rogala Inc.

00 Vermont 103, Andover, VT 05143
/18
$239,500
- 1 Bed
- 1 Bath
- 856 Sq Ft
56 Heritage Condo Way Unit 9, Woodstock, VT 05091

Lots of upgrades to this quiet, two level condo, with lovely views off back baloney. Bonus- new mini split heat pump providing both air conditioning and heat. Kitchen has some upgraded as well with a new dishwasher. This open floor concept condo provides lots of natural sunlight. Cozy up in the living room/dining room and read a book during the winter months overlooking the spacious

Gretchjen Smith Williamson Group Sothebys Intl. Realty

56 Heritage Condo Way Unit 9, Woodstock, VT 05091
/33
$225,000
- 2 Beds
- 1 Bath
- 864 Sq Ft
2579 Vermont Route 100, Plymouth, VT 05056

Tucked among the trees in beautiful Plymouth, this rustic getaway offers a peaceful setting with easy access to outdoor recreation. This property offers unbeatable access to some of Vermont’s best recreation. Just a short drive to both Killington and Okemo for world-class skiing, and minutes from Echo Lake and Plymouth State Park, this is a four-season location ideal for outdoor lovers.The home

Frank Provance Diamond Realty

2579 Vermont Route 100, Plymouth, VT 05056
/34
$250,000
- 1 Bed
- 1 Bath
- 617 Sq Ft
413 Hidden Heights Rd, Chester, VT 05143

Until this last winter this was a really sweet 16 x 24 log cabin. Then it became fire damaged and now the owner would love to have someone bring it back to its former glory. Nice, private area on a town-maintained country road. All utilities are underground, including a 330-gallon propane tank, electric power from the street, and water from the 230' drilled well. The cabin has 1 bath, a

Glenn Olney Barrett and Valley Associates Inc.

413 Hidden Heights Rd, Chester, VT 05143
/60
$240,000
- 3 Beds
- 1 Bath
- 1,024 Sq Ft
442 Vermont 103, Chester, VT 05143

Adorable Village Home in the Heart of Chester, VermontThis charming 3-bedroom, 1-bath home is packed with personality and Vermont village charm! Set on a sunny quarter-acre lot, this sweet property features an oversized deck perfect for summer barbecues, a great yard for play or gardening, and a convenient attached garage.Inside, you’ll love the warm, inviting living space with

Rachael Rogala Rachael Rogala Inc.

442 Vermont 103, Chester, VT 05143
/34
$275,000
- 2 Beds
- 1.5 Baths
- 660 Sq Ft
104 Deer Run Rd Unit C13, Brownsville, VT 05037

Welcome to this nicely maintained 2-bedroom + loft condo offering direct access to the renowned Ascutney Trails—perfect for mountain biking, skiing, hiking, and trail running. Enjoy stunning mountain views from the spacious living room, which features two large sliding glass doors that flood the space with natural light. The open loft above the living area offers even more scenic vistas and

Daniel Preston KW Vermont Woodstock

104 Deer Run Rd Unit C13, Brownsville, VT 05037
/16
$250,000
- 5 Beds
- 2 Baths
- 1,728 Sq Ft
101 Mount Vernon St, Springfield, VT 05156

Built as a duplex, this and last owner have used it as a single family. Therefore there are no traditional figures for income and expenses. Easy to transform into the duplex for income by adding appliances to the upstairs apartment. This home has many upgrades including siding, windows, decks/railings/stairway (outside). Drive is paved and there looks to be room to replace the shed. Perfect

Christine Lewis Brattleboro Area Realty

101 Mount Vernon St, Springfield, VT 05156
/6
$225,000
- Land
- 4.30 Acres
- $52,326 per Acre
51 Loveland Rd, Norwich, VT 05055

Fantastic opportunity to build your dream home on this 4.3 -acre lot in Norwich, Vermont, complete with full architectural plans for the exact home the sellers were planning to build, as shown in the photos and renderings. The property has already undergone significant preparation, including completed building designs and preliminary plans for the water and septic system along with other

Spenser Molloy Nexthome Modern Realty

51 Loveland Rd, Norwich, VT 05055
/29
$299,000
- 3 Beds
- 2 Baths
- 1,232 Sq Ft
842 Main St, Proctorsville, VT 05153

Cared for by one owner for many years, this two-story home on .26 +/- acres was rebuilt in 1977 and would make a very cute ski house, vacation or full-time home. Enter through the enclosed breezeway which is a great space for entertaining or relaxing. The eat-in kitchen includes a breakfast/dining nook and excellent counter space. The living room is spacious and has plenty of natural light. A

Geralyn Donohue Engel & Völkers Okemo

842 Main St, Proctorsville, VT 05153
/36
$250,000
- 3 Beds
- 1.5 Baths
- 1,900 Sq Ft
31 Maple St, Windsor, VT 05089

Discover classic Vermont charm in this 3-bedroom, 1.5-bathroom home located on a quiet, tree-lined street just steps from downtown Windsor. This home is perfect for those who appreciate historic charm and are ready to make it their own. Inside, you’ll find a welcoming layout and abundant natural light. The first floor features a full bathroom, laundry, spacious living and dining areas, and an

Tara Reeves Vermont Real Estate Company

31 Maple St, Windsor, VT 05089
/28
$250,000
- 1 Bed
- 1 Bath
- 396 Sq Ft
80 Pleasant St, Ludlow, VT 05149

Ludlow Village Tiny House with private frontage on the Black River - an ideal home base for enjoying all that Vermont has to offer. Just a short walk to the village's restaurants and shops, and only minutes to skiing, golf, and year-round recreation. The backyard is tucked away from the road, offering a peaceful outdoor retreat with a storage shed and direct river access. Whether you're looking

Debra Staniscia Four Seasons Sotheby's Int'l Realty

80 Pleasant St, Ludlow, VT 05149
/35
$245,000
- 2 Beds
- 1 Bath
- 1,012 Sq Ft
145 Main St Unit 303, Ludlow, VT 05149

Beautiful condo in the heart of downtown Ludlow. Village vibes, unbeatable convenience—The Mill offers walk-to-everything access and a front-row seat to shopping, restaurants, golfing, with the Okemo shuttle just steps away. Perfect as a year-round home or your go-to landing pad after carving turns on the mountain. With exposed beams, original brickwork, and wide plank wood ceilings, this sweet

Frank Provance Diamond Realty

145 Main St Unit 303, Ludlow, VT 05149
/19
$249,900
- 3 Beds
- 1 Bath
- 940 Sq Ft
86 Webster Rd, Hartland, VT 05048

Tucked away on a quiet, town-maintained road, this charming chalet offers the perfect blend of seclusion and convenience. Just 5 minutes from the quaint center of Hartland and only 20 minutes to the vibrant towns of Woodstock, Vermont and Lebanon, New Hampshire, you’ll enjoy the serenity of country living without sacrificing access to shops, dining, and cultural attractions.Inside, this

Jim Bialowski BHG Masiello Keene

86 Webster Rd, Hartland, VT 05048
/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
/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
/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
/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
/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
/25
$207,000
- 3 Beds
- 3 Baths
- 1,604 Sq Ft
295 Hotel Rd Unit 10/10A, Brownsville, VT 05037

This spacious walk-up condominium features 3 bedrooms and 3 full baths, with an inviting open-concept living and dining area anchored by a cozy fireplace. Step out onto your private deck overlooking the tubing hill and take in all the action just outside your door!This vibrant community offers an unbeatable lifestyle with access to approximately 1,300 acres of outdoor fun, including

Allison Griep KW Vermont Woodstock

295 Hotel Rd Unit 10/10A, Brownsville, VT 05037
/48
$215,000
- 3 Beds
- 3 Baths
- 1,600 Sq Ft
295 Hotel Rd Unit 17, Brownsville, VT 05037

OWN FOR LESS THAN YOU CAN RENT!! Spacious and bright end unit condo on Ascutney Mountain. Fireplaced living room, dining area with balcony, kitchen and even an entry enclave. 3 bedrooms with 3 full baths. 1 bed/bath on 1st floor. 2 bedrooms, 2 baths, multiple closets and a sitting area on the upper level. The advantage of the 3rd floor is that you get the loft area, cathedral ceilings and some

Crystal Moses Crystal Moses

295 Hotel Rd Unit 17, Brownsville, VT 05037
/34
$299,000
- 5 Beds
- 2 Baths
- 2,560 Sq Ft
630 Vermont 14, Bethel, VT 05032

630/642 on VT Route 14 in East Bethel Village are two homes on one deeded parcel consisting of 1.2 +/- acres. The main home is a large New Englander style house with 3 bedrooms and updated bathroom. Above, and with a separate entrance, you will find an apartment with 2 bedrooms and a full bath. The main home and the apartment have been rentals in the past and could be again with a little TLC.

Eric Kenyon Rural Vermont Real Estate

630 Vermont 14, Bethel, VT 05032
/32
$299,000
- 6 Beds
- 2 Baths
- 2,518 Sq Ft
761 Main St, Cavendish, VT 05153

Location, Location, Location...Large families and investors take note. This classic colonial located on the corner of Main Street and Twenty Mile Stream Road is ready for the next family to enjoy or use for rental income. This was the family's gathering house for 55 years, and now it could be yours. There are 6 bedrooms, a woodstove/fireplace, mudroom, 1 car garage/workshop, and bonus space on

Kevin Barnes William Raveis Real Estate Vermont Properties

761 Main St, Cavendish, VT 05153
/20
$250,000
- Land
- 28 Acres
- $8,772 per Acre
00 Chapel Hill Rd, Sharon, VT 05065

Located on a class IV road, right after the end of the publicly maintained section of Chapel Hill Road, this 28.5 acre parcel has potential for a camp, off-grid home, or as a recreational getaway. The Seller has roughed in a driveway to a level spot about 600 feet from the town maintained road. Build here or clear at the top of the land for incredible views of Mt. Ascutney, Killington, and

Tami Sullivan Snyder Donegan Real Estate Group

00 Chapel Hill Rd, Sharon, VT 05065

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Copyright 2025 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.