Windsor County VT Homes under $300,000

/28
$259,000
- 2 Beds
- 1 Bath
- 834 Sq Ft
3810 North Rd, Bethel, VT 05032

Country Charmer on North Road | Royalton, VTSimple living at its finest! This easy-to-maintain home is nestled on the Royalton-Barnard town line and offers a peaceful setting with views of Cleveland Brook flowing gently along the back of the property.Step inside through a heated entry/mudroom, and you’re welcomed into a spacious open concept living area with cathedral ceilings, an abundance of

Eric Kenyon Rural Vermont Real Estate

3810 North Rd, Bethel, VT 05032
/38
$259,000
- 3 Beds
- 1 Bath
- 1,679 Sq Ft
707 Skitchewaug Trail, Springfield, VT 05156

Vermont charm meets modern convenience in this beautifully updated 3-bedroom, 1-bath home on 2.9 private acres in Springfield. From the brand new septic system to fresh interior and exterior paint, this property has been thoughtfully improved throughout. Enjoy single-level living with a spacious primary bedroom, full bathroom, and laundry on the main floor. The cozy living room features a warm

Nick Sicard EXP Realty

707 Skitchewaug Trail, Springfield, VT 05156
/14
$250,000
- 2 Beds
- 1 Bath
- 1,488 Sq Ft
1360 Vermont 106, Weathersfield, VT 05151

2-bedroom home set on 2.7 peaceful acres in scenic Weathersfield, VT. This property offers a cozy layout with a small, functional kitchen, Step outside to enjoy a large backyard—perfect for gardening, entertaining, or just relaxing. The detached 2-car garage provides additional storage or workshop potential, though it could use a little TLC. Conveniently located with easy access to Route 106 and

Henry Vashaw Twin State Realty LLC

1360 Vermont 106, Weathersfield, VT 05151
/23
$255,000
- 4 Beds
- 1 Bath
- 1,008 Sq Ft
59 Weston Heights, Windsor, VT 05089

Great Location! Well-Maintained! 4BR's Cape Full Basement with work bench, Many recent updates in the last three years, Rear deck, Garden area and Private backyard.

Don Chabot Town and Country Realty

59 Weston Heights, Windsor, VT 05089
/18
$264,900
- 5 Beds
- 1 Bath
- 1,603 Sq Ft
274 Mill Rd, White River Junction, VT 05001

Nice 5 bedroom Colonial on almost 2.5 acres of privacy. Nice open floor plan with a beautiful kitchen packed with cabinets. Large bedrooms. Great location and priced to sell.

Thomas Cafarella Cameron Real Estate Group

274 Mill Rd, White River Junction, VT 05001
/34
$250,000
- 3 Beds
- 2 Baths
- 2,121 Sq Ft
222 River St, Bethel, VT 05032

Nestled on over an acre of serene countryside, this 3-bedroom, 2-bathroom home offers endless potential for those seeking a peaceful retreat with room to make it their own. Enjoy the beauty of nature with direct river frontage, perfect for fishing, kayaking, or simply relaxing to the soothing sounds of the water. The home features a spacious layout with abundant natural light, offering a cozy

Flex Realty Group Flex Realty

222 River St, Bethel, VT 05032
/27
$200,000
- 1 Bed
- 1 Bath
- 616 Sq Ft
501 Gates Rd, Chester, VT 05143

If you're looking for a smaller footprint, or tiny home living, this is a great option! One bedroom, one bath mobile home in an absolutely gorgeous setting! Sitting on it's own 2+ acres, you'll a large yard with a firepit to enjoy the summer evenings while you gaze out over stone walls to a beautiful view. This property is quiet and peaceful, but not far from several ski areas and state parks

Rebecca Seymour Brattleboro Area Realty

501 Gates Rd, Chester, VT 05143
/26
$289,000
- 2 Beds
- 1.5 Baths
- 1,048 Sq Ft
292 Woodhaven Dr Unit 9M, White River Junction, VT 05001

Turn-key renovated and well-maintained condo with many updates. Private, country setting located in highly sought-after Woodhaven Manor Condominiums. Just a short drive to Dartmouth college (2.5 miles), DHMC, and shopping in the Upper Valley. These units are mainly owner-occupied and pet friendly. This unit has been freshly painted throughout, with new carpet and vinyl flooring, laundry area plus

Gerry Stark RE/MAX Upper Valley

292 Woodhaven Dr Unit 9M, White River Junction, VT 05001
/28
$240,000
- 3 Beds
- 1 Bath
- 1,654 Sq Ft
2125 U S 5, Windsor, VT 05089

With fabulous curb appeal and a welcoming covered porch, this turn-key circa 1940 New England home beautifully blends timeless design with modern comfort. The open-concept kitchen and dining area flow seamlessly into spacious living areas, creating a warm and inviting atmosphere. Elegant features such as French doors, a fireplace with a classic brick hearth, and bay windows add character and

Katie Ladue Gilbert KW Vermont Woodstock

2125 U S 5, Windsor, VT 05089
/26
$249,000
- 2 Beds
- 1 Bath
- 1,192 Sq Ft
1568 S Hill Rd, Ludlow, VT 05149

Cozy home on 2.3+/- acres. Great location out in the country on South Hill. Stone wall and lovely meadow visible from the living room picture window. Open floor plan, wide board wood floors. Just 10 minutes to Okemo Mountain Resort. Water intrusion in basement caused settling and damage. Bring your contractor and see what might be possible!

Alexandra Eatmon Kelley Real Estate, Inc.

1568 S Hill Rd, Ludlow, VT 05149
/18
$229,000
- 2 Beds
- 2 Baths
- 1,665 Sq Ft
3 Fitch Ct, Windsor, VT 05089

Ready for the next generation is this lovingly cared for New Englander.Nestled on a quiet side street in the heart of Windsor, VT, this classic 2-bedroom, 2-bath home offers both character and warmth. The inviting front porch welcomes you into a sunlit living space featuring hardwood floors, original woodwork, and large windows that let in plenty of natural light.The spacious

Katie Ladue Gilbert KW Vermont Woodstock

3 Fitch Ct, Windsor, VT 05089
/37
$249,900
- 3 Beds
- 2 Baths
- 1,479 Sq Ft
182 Upper Round Top Rd Unit E, Plymouth, VT 05056

Sweet mountain 3 bedroom plus loft and 2 full bathrooms furnished and equipped townhouse vacation retreat with beautiful views located minutes to Killington or Okemo Mountain Resort. Offering very close access direct from the townhouse to VAST snowmobiling trails/hiking/mountain biking trails. There are superb lakes right down the road to kayak, swim and fish. The floor plan is open concept ideal

Will Spanos KW Vermont-Killington

182 Upper Round Top Rd Unit E, Plymouth, VT 05056
/15
$280,000
- Land
- 9 Acres
- $32,825 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
- 2 Beds
- 1 Bath
- 856 Sq Ft
982 Vermont 14, Royalton, VT 05068

Welcome to this cozy and well-maintained home, perfectly situated close to local shops and restaurants for ultimate convenience. Step inside to a convenient mudroom area, with plenty of space to take off those muddy boots. The home opens into a nicely sized living room and kitchen with an island that offers additional prep and seating space. Two bedrooms down the hall share a full bathroom and

Shenia Covey Lyford Coldwell Banker LIFESTYLES - Hanover

982 Vermont 14, Royalton, VT 05068
/22
$299,000
- 2 Beds
- 1.5 Baths
- 1,048 Sq Ft
226 Woodhaven Dr Unit 8J, White River Junction, VT 05001

This beautifully maintained 2-bedroom condo in the desirable Woodhaven community offers convenient and low-maintenance living. Just a short drive from Dartmouth College and downtown Hanover, this location is ideal for commuters, students, or anyone looking to enjoy the Upper Valley lifestyle.Step inside to find updated stainless steel appliances, clean and renovated bathrooms, and

Holly Hall Hall Collins Real Estate Group

226 Woodhaven Dr Unit 8J, White River Junction, VT 05001
/21
$249,000
- 3 Beds
- 2 Baths
- 1,248 Sq Ft
42 Melody Ln, Springfield, VT 05156

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 thoughtfully remodeled, one-level layout featuring three bedrooms and two baths. The open-concept kitchen and living room create an

Linda Benoit Highland Realty

42 Melody Ln, Springfield, VT 05156
/15
$255,000
- 2 Beds
- 1.5 Baths
- 1,043 Sq Ft
253 Old Quechee Rd Unit 4E, Hartford, VT 05001

Mill Run Condo, a QLLA property, is conveniently located close to the Upper Valley, Ski Resorts, Woodstock, and Dartmouth College. This condo features an open floor plan on the main level with a tree house feel from the deck that has views of the Ottauquechee River in the winter and is in the tree canopy in spring, summer, and fall. The kitchen is open to the dining room, with a wood stove. The

Dail Frates Snyder Donegan Real Estate Group

253 Old Quechee Rd Unit 4E, Hartford, VT 05001
/26
$289,000
- 2 Beds
- 1.5 Baths
- 1,048 Sq Ft
292 Woodhaven Dr Unit 9M, White River Junction, VT 05001

Turn-key renovated and well-maintained condo with many updates. Private, country setting located in highly sought-after Woodhaven Manor Condominiums. Just a short drive to Dartmouth college (2.5 miles), DHMC, and shopping in the Upper Valley. These units are mainly owner-occupied and pet friendly. This unit has been freshly painted throughout, with new carpet and vinyl flooring, laundry area plus

Gerry Stark RE/MAX Upper Valley

292 Woodhaven Dr Unit 9M, White River Junction, VT 05001
/25
$209,900
- 3 Beds
- 2 Baths
- 1,876 Sq Ft
2350 Vt Route 10, Chester, VT 05143

Great Double Wide Mobile Home. The sale of this property being listed is contingent upon the proposed Seller (or "Owner") completing his/her/its purchase of this property. "Seller" currently has this property under contract for purchase.

Derek Greene Derek Greene

2350 Vt Route 10, Chester, VT 05143
/9
$275,000
- Land
- 0.43 Acre
- $639,535 per Acre
1054 W Woodstock Rd, Woodstock, VT 05091

Ideally located parcel across West Woodstock Road from the Woodstock Farmers Market and 500 yards from the entry to Woodstock Union Middle & High School. Public water and sewer available with access off Prosper Road near the junction of US Road Route 4/West Woodstock Road. Building plans available. Multi-unit housing development potential in zero vacancy environment.

Laird Bradley Williamson Group Sothebys Intl. Realty

1054 W Woodstock Rd, Woodstock, VT 05091
/9
$299,000
- Land
- 86 Acres
- $3,461 per Acre
00 Tarbell Hill Rd, Perkinsville, VT 05151

Discover an expansive 86.4± acre Vermont retreat perched on a scenic hillside in Weathersfield, offering breathtaking long-range views of Ascutney Mountain. A winding brook follows the road frontage, enhanced by seasonal streams that bring the landscape to life each spring. Historic trails, old stone walls, and remnants of former homesteads lend a unique charm rarely found elsewhere. The driveway

Randy Snelling KW Coastal and Lakes & Mountains Realty/Hanover

00 Tarbell Hill Rd, Perkinsville, VT 05151
/34
$299,500
- 2 Beds
- 2 Baths
- 1,373 Sq Ft
58 Valley View Rd Unit 1, Bridgewater Corners, VT 05035

Main floor two-bedroom, 2-bathroom condo with lovely mountain views. An open floor plan which outfits the living room, dining and kitchen with plenty of natural light. In addition is the primary ensuite, 3/4-bathroom, second bedroom and office/den. Common space includes a coin operated laundry facility, shared deck, gazebo, and a storage room, along with 2 parking spaces per unit. The property is

Terry Davis Williamson Group Sothebys Intl. Realty

58 Valley View Rd Unit 1, Bridgewater Corners, VT 05035
/10
$225,000
- Land
- 2.64 Acres
- $85,227 per Acre
00 Stagecoach Rd, Norwich, VT 05055

Building lot ready for construction. Vermont State Septic and Well permit on file. Septic design is a 4 bedroom gravity inground system. Power and EC Fiber on pole at land. Lot is gently slopping, lightly wooded and has good sunlight. Situated on private road with easy access to hiking, biking and recreation. Minutes to town, Dartmouth and the greater Upper Valley.

Linda White EXP Realty

00 Stagecoach Rd, Norwich, VT 05055
/11
$285,000
- 5 Beds
- 2.5 Baths
- 1,800 Sq Ft
23 Pleasant St, Springfield, VT 05156

Perfect for the investor! This three bedroom home has been totally and tastefully renovated into five private rental units. Easily able to convert to a single family or duplex. This house features aluminum siding, a brand new forced hot water heating system and new 200 AMP electrical panel. Nothing left to do but collect rent.

Gale Alger Alger Real Estate Agency

23 Pleasant St, Springfield, VT 05156
/22
$249,900
- Land
- 12 Acres
- $21,178 per Acre
0 Wildlife Rd Unit 5025731, Hartford, VT 05001

Incredible year-round vast and long range mountain views on this open land perched at the top of a hill with the septic design and permit already in place. There is power on the poles that have already been brought up to the cleared house-site along the installed and established gravel driveway large enough for a firetruck to turn around. This has been professionally surveyed by Pathways

Franchesca Collins Hall Collins Real Estate Group

0 Wildlife Rd Unit 5025731, Hartford, VT 05001
/15
$269,000
- Land
- 10 Acres
- $27,393 per Acre
00 Chapel Hill Rd, Sharon, VT 05065

Fantastic land lot for the construction of your new home! This shovel-ready site in Sharon, VT is just over the Norwich town line in the Beaver Meadow neighborhood. No further tree clearing is needed. The hardpack driveway leads up to a beautiful and private setting where 200-amp electrical service from GMP has already been installed (underground), along with a 4-bedroom spec septic system and

Josh Hunt Snyder Donegan Real Estate Group

00 Chapel Hill Rd, Sharon, VT 05065
/14
$275,000
- Land
- 17 Acres
- $16,176 per Acre
1047 Rte 100, Weston, VT 05161

This 17+/- acre property is an exceptional land opportunity located just 2 miles outside the picturesque Village of Weston. A prime location for outdoor lovers, it offers easy access to some of Vermont’s top ski resorts, including Okemo, Stratton, Magic, and Bromley Mountain, ensuring year-round recreation from skiing and snowboarding to hiking and mountain biking. The Village of Weston is home

Cheyanne Pugliese Wohler Realty Group

1047 Rte 100, Weston, VT 05161
/27
$249,000
- 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

95 Union St, Springfield, VT 05156
/31
$249,000
- 3 Beds
- 2 Baths
- 1,800 Sq Ft
35 Family Cir, Hartland, VT 05001

An exciting opportunity to own a new 3-bedroom, 2-bath double-wide home in Hartland, VT Open Concept Living: Bright family area with built-in storage. Stylish Kitchen & Dining: Includes a large island and a walk-in corner pantry. Luxurious Primary Suite: Enjoy a walk-in shower, private commode, double sinks, and a massive walk-in closet. Additionally two more Bedrooms at the end of the hall,

Jenna Luce RE/MAX Upper Valley

35 Family Cir, Hartland, VT 05001
/22
$299,000
- Land
- 91 Acres
- $3,286 per Acre
000 Green Mountain Turnpike, Andover, VT 05143

91± Acres with Stunning Mountain Views in Chester, Vermont Discover a breathtaking 91± acre property just minutes from the charming village of Chester, Vermont. This expansive parcel features stunning alpine views of Fox Chair Mountain, over 3,000 feet of road frontage, and power and internet access along more than half the frontage. Located on the historic Green Mountain Turnpike, this property

Daire Gibney Barrett and Valley Associates Inc.

000 Green Mountain Turnpike, Andover, VT 05143
/14
$239,000
- Land
- 10 Acres
- $23,663 per Acre
0 Christian St Unit 5019436, Hartford, VT 05001

Beautiful, in town location. A very rare opportunity to own an in town Christian Street parcel of land. If you've been having a hard time finding the right home in this very tight housing market Or if you've been dreaming about new construction in the Hartford / Upper Valley area than look no further. This building lot is conveniently located only minutes from Downtown White River Junction. This

Alex DeFelice The Clerkin Agency, P.C.

0 Christian St Unit 5019436, Hartford, VT 05001
/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

1090 New Boston Rd, Norwich, VT 05055
/31
$300,000
- 2 Beds
- 1.5 Baths
- 1,070 Sq Ft
27 Lawrence Hill Rd Unit 5, Weston, VT 05161

Tuttle Barn Unit 5 enjoys one of Weston's best views overlooking the West River waterfalls and historic Mill with lovely meadows and mountains beyond! The handsome c. 1907 barn was converted to condos in 1983 and, with just five units “the barn” offers the best of in-town living with a small footprint and low-to-no maintenance demands. This charming unit offers two bedrooms (plus a loft) and

Claudia Harris Mary Mitchell Miller Real Estate

27 Lawrence Hill Rd Unit 5, Weston, VT 05161
/31
$300,000
- 2 Beds
- 1.5 Baths
- 1,070 Sq Ft
27 Lawrence Hill Rd Unit 5, Weston, VT 05161

Tuttle Barn Unit 5 enjoys one of Weston's best views overlooking the West River waterfalls and historic Mill with lovely meadows and mountains beyond! The handsome c. 1907 barn was converted to condos in 1983 and, with just five units “the barn” offers the best of in-town living with a small footprint and low-to-no maintenance demands. This charming unit offers two bedrooms (plus a loft) and

Claudia Harris Mary Mitchell Miller Real Estate

27 Lawrence Hill Rd Unit 5, Weston, VT 05161
/19
$200,000
- 3 Beds
- 2 Baths
- 1,234 Sq Ft
8 Pine Brook Ln Unit D1, North Springfield, VT 05150

Welcome to your new home, in a comfortable 3 bedroom, 2 bathroom unit in a welcoming and beautifully landscaped condominium community! Located in the highly sought-after Pine Brook condominium complex, this large end-unit offers the rare advantage of a first floor primary bedroom. On the main floor, you'll find a spacious living room, the primary bedroom with air conditioning and a full adjoining

Chelsea Richardson Barrett and Valley Associates Inc.

8 Pine Brook Ln Unit D1, North Springfield, VT 05150
/33
$295,000
- Land
- 1.03 Acres
- $286,408 per Acre
0 Gill Terrace Unit 5014671, Ludlow, VT 05149

Ludlow Village lot with just over an acre and a 2 story carriage house. Imagine the possibilities with the classic lines of the vintage carriage house that has 3 sets of swinging bay doors and an entry door as well. There are stairs to the second level that has 2 sets of dormered windows and tons of storage space. The large village lot provides many options for building locations so you can take

Kevin Barnes William Raveis Real Estate Vermont Properties

0 Gill Terrace Unit 5014671, Ludlow, VT 05149
/25
$229,000
- 3 Beds
- 3 Baths
- 2,084 Sq Ft
162 Park St, Springfield, VT 05156

This main unit of this c. 1880 house has been used as an office for years, with two residential rental units. Recently, the office area has been leased as a 2-bedroom apartment, but a new owner could use that and the upstairs unit as their residence and keep the small 1-bedroom unit in the back for some income to help with your mortgage or taxes. Located on a level lot, very convenient to the

Glenn Olney Barrett and Valley Associates Inc.

162 Park St, Springfield, VT 05156
/7
$229,000
- Studio
- 2,084 Sq Ft
162 Park St, Springfield, VT 05156

3 unit building with a large 3 bay barn/garage. Nice level corner lot near the Springfield hospital and elementary school. Close to the shopping center.

Glenn Olney Barrett and Valley Associates Inc.

162 Park St, Springfield, VT 05156
/21
$230,000
- Land
- 14 Acres
- $16,476 per Acre
0 Valley View Dr Unit 5009431, Andover, VT 05143

This piece of land offers a unique combination of privacy and expansive long-range views at an elevation of 2000+ feet, making it an ideal location for your dream home in Southern Vermont. Nestled within a serene community of fine homes, this lot is one of the few remaining opportunities to build in this desirable area. The land has a waste water permit and comes with a community leach field

Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

0 Valley View Dr Unit 5009431, Andover, VT 05143
/10
$289,900
- Land
- 34 Acres
- $8,654 per Acre
00 Vermont Route 100, Weston, VT 05161

Weston Opportunity Bordering Okemo State Forest - 33.5 Acres of Vermont is waiting for your cabin...or perhaps you have a tiny house design in mind or more? The current owners are willing to share their vision for this beautiful lot and are offering it for sale. They have begun research with an engineer. This parcel has over 2,000 feet of stream frontage on a branch of the West River. The

Tyleen Murray Kelley Real Estate, Inc.

00 Vermont Route 100, Weston, VT 05161

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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.