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Windham County

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487 Vermont Route 100 Londonderry VT 05155

Londonderry, VT487 Vermont Route 100

Price$1,385,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5089929

  • Residential Single Family
  • Full Bath 1
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 4,153

Set on nine acres, this inviting three bedroom brick home offers a rare blend of comfort, space, and rural charm. The main level features a large primary bedroom, with a beautiful full bathroom and walk in closet. Each room on the main level you'll find bright and comfortable living spaces and a beautiful sunroom that overlooks the surrounding fields. Upstairs, two spacious bedrooms share a bathroom, providing an ideal layout for family or guests. The finished basement offers a family room and bar area, perfect for entertaining, relaxing or additional living space. The main property has an attached two car garage. The property includes a spacious barn with a full 1 bedroom apartment above- perfect for guests, extended family, or rental opportunity. With abundant storage throughout both the home and barn, this property is perfectly suited for those seeking peaceful country living with modern amenities and room to grow.

Listed by Jamie Wylie of Stratton Real Estate

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Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.48% last updated on 2026-06-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

156 West Lake Road Wilmington VT 05356

Wilmington, VT156 West Lake Road

Price$1,300,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5078282

  • Residential Single Family
  • Full Bath 2
  • Address 156 West Lake Road
  • Bedrooms 3
  • Bathroom 4

A rare opportunity to own a beautifully maintained, one-family-owned home on Lake Raponda. Lovingly cared for through the years. This special waterfront property offers the perfect blend of comfort, warmth, and classic Vermont charm. Spend your days boating, kayaking, swimming, or simply relaxing by the shore, and unwind in the quiet beauty that makes Lake Raponda so special. Step inside to an inviting open-concept kitchen, living, and dining area-ideal for gathering with family and friends. A cozy wood-burning fireplace creates the perfect ambiance on chilly evenings, while a wood stove adds both character and efficiency. Large windows invite in natural light and frame peaceful lake views. Step outside onto the spacious deck overlooking the water-an ideal spot for morning coffee, summer dinners, or simply relaxing while taking in the tranquil surroundings. Ideally located just minutes to the charming village of Wilmington for dining, shopping, and local events, and approximately 15 minutes to world-class skiing at Mount Snow. Outdoor enthusiasts will love the surrounding beautiful hiking trails, making this a true four-season retreat. Opportunities like this don't come along often - lakefront living in such a prime location is truly special.

Listed by Jillian Wimmelman of Deerfield Valley Real Estate

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Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.48% last updated on 2026-06-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

580 Cross Road Londonderry VT 05155

Londonderry, VT580 Cross Road

Price$1,300,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5090584

  • Residential Single Family
  • Full Bath 3
  • Address 580 Cross Road
  • Bedrooms 4
  • Bathroom 3

Thoughtfully designed with both craftsmanship & efficiency in mind, the home exceeds modern energy standard, achieving an impressive energy efficient rating. 3-bedroom, 2-bath barn-style residence with 1-bedroom guest house & sauna. The 5BR Wastewater permit allows for potential future expansion/addition. A Masterful fusion of heritage & refined elegance, situated on 5.4 pristine acres. Absorb the beauty of reclaimed exposed overhead beams, while expansive floor-to ceiling custom-crafted windows capture mountain vistas & bathe interiors in golden natural light. Large sliding doors open to the melody of a gentle brook & surrounding woods, creating a sense of calm. Step into an expansive open floor concept, with dramatic ceilings that amplify the home's sense of scale. The Shaker style inspired chef's kitchen is well equipped with new Unique brand appliances, salvaged soap stone sink, open cabinetry & a custom breakfast bar. The dining room is furnished with a refurbished-custom dining table, creating the feel of farm fine dining. The primary suite is a true sanctuary, featuring a spa-inspired ensuite bath with striking VT green slate walk-in shower, clawfoot bathtub, artisan sink, &curated furnishings that exude warmth & sophistication. Accompanied by a loft that serves as a bonus room or office, the 2nd level adds a spacious dimension to the home. Two additional bedrooms offer generous space for family or guests, with views of the surrounding woods & mountains. A luxurious bathroom features a vintage sink & a free-standing tub. The accessory dwelling is a tree house like structure, with 1 Bedroom, 1 bathroom, full kitchen, private hot tub & sauna. This space is ideal for guest to unwind & enjoy a spa-like experience. Every space is thoughtfully designed to offer a lifestyle where nature's beauty and exquisite-yet rustic craftsmanship meet. Owner is licensed realtor.

Listed by Loana Sargent and Trent Stephens of Wohler Realty Group

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Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.48% last updated on 2026-06-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

4427 West Hill Road South Jamaica VT 05343

Jamaica, VT4427 West Hill Road South

Price$1,295,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5090616

  • Residential Single Family
  • Full Bath 2
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 3,040

One-of-a-kind luxury lodge offering the comfort and amenities of a five-star retreat with the warmth and charm of a Vermont mountain home. The house provides all the space your friends and family could want-an expansive open layout perfect for gatherings, along with plenty of cozy, private spots for quiet moments. Enjoy movie nights in the 11-foot home theater, or relax in front of one of two fireplaces with your favorite beverage while watching the snow fall. The great room features a 90-inch TV, perfect for watching your favorite sporting event. Outdoors, you'll find a grill and seating area for dining under the stars beside a six-person hot tub and an eight-person sauna. After your meal, gather around the fire pit to roast marshmallows and take in the beauty of the surrounding forest. No expense was spared in creating this extraordinary Vermont home-thoughtfully designed for comfort, connection, and unforgettable memories.

Listed by Carrie Mathews of Winhall Real Estate

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Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.48% last updated on 2026-06-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

732 Under the Mountain Road Londonderry VT 05155

Londonderry, VT732 Under the Mountain Road

Price$1,250,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5043818

  • Residential Single Family
  • Full Bath 1
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 3,516

With 42+ stunning acres and unrivaled panoramic mountain (and sunset) views, this beautiful historic home seamlessly blends an extraordinary sense of history, grace, modern amenities, and will offer you the quintessential Vermont experience! Originally built in 1810 and artfully reimagined in 1987, the 5BR farmhouse features exposed beams, wide plank wood floors, and architectural character, and the thoughtful layout and updated living spaces enhance functional living, energy efficiency, and lots of natural light - perfect for larger gatherings or intimate enough for simply finding your own space to retreat in peace and enjoy the view. There is a large timber-frame barn outfitted for horses or livestock, complete with stalls, tack room, and workshop areas. Additional outbuildings provide space for hobbies, tools, and vehicles, and nearby is a charming but rustic cottage (bring your imagination). The land itself is both scenic and purposeful, enrolled in Vermont's Current Use program, which supports sustainable forestry and brings the benefit of reduced property taxes. The land is full of possibilities - wander through flower-filled meadows, harvest sweet treats from the blueberry patch, or explore the woods and create a network of bike/hike/ski trails. All this, just minutes from Londonderry and neighboring towns, a renowned farmers market, restaurants, and shops. Four major ski areas, including Stratton, Bromley, Magic, and Okemo, are within easy reach, as are Lowell Lake and a host of outdoor adventures. 732 Under the Mountain Road is more than a property - it's a lifestyle, a legacy, and a rare opportunity to own a piece of Vermont's most breathtaking landscape.

Listed by Claudia Harris of Mary Mitchell Miller Real Estate

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Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.48% last updated on 2026-06-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

390 Pleasant Valley Road Brattleboro VT 05301

Brattleboro, VT390 Pleasant Valley Road

Price$1,249,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5088064

  • Residential Single Family
  • Full Bath 2
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 4,491

Escape to this beautifully updated home set on 25.9 idyllic acres of forests, meadows and stone walls, while only minutes from amenities including the local creekside farmers market, treasured food co-op and Brattleboro's vibrant downtown. A gorgeous stone floor and blown glass windows in the entry vestibule set the tone as you are drawn to the stunning great room. The home tastefully captures the historic essence of Vermont with its chestnut beams, wide plank flooring and stylish yet unpretentious design. Interior features offer the perfect balance of grandeur and intimacy with oversized windows that bathe the rooms in natural light, 3 fireplaces and authentic lighting. The kitchen is a culinary haven with state-of-the-art appliances and stunning Brazilian countertops, providing ample workspace and an eat-in area. The first floor also offers a formal dining room, a guest/primary suite with a private entrance and laundry, an office, and it's completed by a sitting room where the current owners gather around the piano. Upstairs you'll find a generous primary suite, two bedrooms, and one with a connecting room, an ideal playroom or office. The walk-out basement is partially finished with a workout room, laundry room and abundant storage. The house includes high-speed fiber internet and a whole-house generator. The attached 2-car garage is heated and a second heated detached 2-car garage with a finished loft above is perfect for playing pool and foosball with family & friends. Relaxation comes easily by the inviting in-ground pool overlooking tranquil woodlands, the stone-terraced landscape and native wildlife. This special property is nestled in a friendly community on a country road, adjacent to 367 acres of protected land with trails perfect for hiking, biking and snowshoeing. Just 2 hrs to Boston, 3.5 hrs to NYC with direct Amtrak to NYC. Easy drive to ski mountains.

Listed by Kristen Ziter Taylor of Brattleboro Area Realty

{$office->Name}

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.48% last updated on 2026-06-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

350 Sunset Lake Road Newfane VT 05362

Newfane, VT350 Sunset Lake Road

Price$1,215,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5089719

  • Residential Single Family
  • Full Bath 3
  • Address 350 Sunset Lake Road
  • Bedrooms 4
  • Bathroom 3

Experience the timeless charm of Vermont living at this beautifully renovated farmhouse estate sitting on 92 acres in Newfane Vermont. Originally restored and thoughtfully updated, this exceptional antique farmhouse seamlessly blends historic character with modern comfort and convenience. Unlike many older homes, this property features expansive rooms, high ceilings, wood floors, abundant natural light, and generous storage. For ease of ownership there is an automatic propane generator and the septic was redesigned in 2022. In addition to all of this is a beautifully crafted timber frame barn that utilized reclaimed beams from the original structure on the property. Rich in authentic New England character, the home showcases exposed hand-hewn beams, a stunning chef's kitchen with custom cabinetry, a massive stone hearth with a traditional beehive oven, and a unique gardener's foyer complete with workspace and cast-iron wash sink. The spacious first-floor primary suite offers cathedral-beamed ceilings, a charming loft area, and a private retreat-like atmosphere. A sun-filled four-season sunroom overlooks the beautifully landscaped grounds and perennial gardens. Set on a large lot of private Vermont countryside, the property includes antique stone walls, approximately 5 acres of open meadowland, apple trees, maintained walking trails, and a large fenced garden area. Outdoor enthusiasts will appreciate the close proximity to Sunset Lake, located just a half mile away for kayaking, paddling, and peaceful recreation. Ideally located just minutes from downtown Brattleboro and only 1.5 miles from a paved road, this private country estate offers the perfect blend of seclusion, convenience, and the idyllic Vermont lifestyle. Whether you are seeking a homestead, equestrian property, country retreat, or full-time residence, this one-of-a-kind Vermont farmhouse is a rare opportunity to own a truly special piece of New England paradise.

Listed by Keith Nowak of Four Seasons Sotheby's Int'l Realty

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Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.48% last updated on 2026-06-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

8 Twin Rocks Road Dover VT 05356

Dover, VT8 Twin Rocks Road

Price$1,200,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5091891

  • Residential Single Family
  • Full Bath 2
  • Address 8 Twin Rocks Road
  • Bedrooms 5
  • Bathroom 5

Extraordinary VT Mountain Property w/ Stunning Barn Minutes to Mt Snow & convenient access to VT's renowned VAST snowmobile Trails System. Mountain Retreat w/amazing Income & Expansion Potential. Tucked away at end of a quiet country road in desirable West Dover, this remarkable 5-bdrm, 5-bath contemporary offers the perfect blend of privacy, recreation & opportunity. This property is ideally positioned for year-round enjoyment & investment potential. Built in 2000 & thoughtfully designed for the gathering of family & friends. The home features generous living spaces throughout. The inviting living room centers around a wood-burning fireplace, creating the perfect setting after a day on the slopes or trails. A spacious family and recreation room in the finished walk out basement offers additional entertaining space. On yet another level is a gathering place complete w/ a propane stove that provides warmth & ambiance during Vermont's winter months & here to be enjoyed. The flexible floor plan includes two main-level bedrooms & three baths, while the second floor offers three additional bedrooms & two baths, providing comfortable accommodations for large groups. With the addition of kitchens, this home could easily be configured into separate living spaces, creating outstanding rental or multi-generational living opportunities. Outside, the setting is equally impressive. Multiple outdoor sitting areas allow you to enjoy the peaceful surroundings, while the standing seam roof, classic clapboard siding, and quality construction reflect enduring Vermont craftsmanship. Adding to the property's uniqueness is the stunning barn perched on the hillside above the home. With outstanding character & views of the surrounding landscape, the barn presents exciting possibilities as a future luxury guest house, studio, workshop, event space, or recreational retreat. Perfect whether seeking a primary residence, four-season getaway, investment property, or a combination of all three.

Listed by Jennifer Baker of Connecticut River Valley Realty

{$office->Name}

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.48% last updated on 2026-06-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

82 North Brookwood Road Stratton VT 05155

Stratton, VT82 North Brookwood Road

Price$1,160,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5086826

  • Residential Single Family
  • Full Bath 4
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 3,664

Location , Location , Location! Situated on North Brookwood just below the covered brige you'll enjoy easy access to the Wanderer ski trail as well as the resort shuttle that picks you up at your driveway! This iconic resort property features a great room with custom wood barrel cathedral ceilings, a wall of glass, wood burning fireplace and wrap around deck. Designed for the mountain enthusiast, this propery has the features you look for in a Resort Residence, 5 bedrooms (which includes a spacious and private primary suite wing), 4 updated bathrooms, a spacious media room that opens to a patio with hot tub and fire pit. The galley kitchen opens to a dining room and all with ease to entertaining and apres ski. This location is prime for winter ski and snowboarding as well as an incredible mountain biking trail system during the summer and fall. Hike, bike, golf and enjoy incredible year round activities. Very few homes become available in the North Brookwood neighborhood. Don't miss an opportunity to create your own mountain lifestyle in this great resort location.

Listed by Kim Morgan-Wohler of Wohler Realty Group

{$office->Name}

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.48% last updated on 2026-06-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

2245 Burrington Hill Road Whitingham VT 05361

Whitingham, VT2245 Burrington Hill Road

Price$1,150,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5090460

  • Residential Single Family
  • Full Bath 1
  • Bedrooms 4
  • Bathroom 1
  • Square Feet 1,972

Lovely 1800s vintage dairy farm on 100+ acres in the heart of Whitingham Vermont, just a short driving to nearby country villages, lakes, skiing, and more. Conveniently just over the MA border sits this amazing property which has been in the same family for 2 generations. Nestled on the crest of rolling pasture, you are treated to long range three state mountain views including Mount Monadnock to the East. The property could easily accommodate a beautiful new build, or else could be rehabbed into a working dairy or gentleman's farm, with privacy and access rare to find. The main house presently features 4 bedrooms, 1 bath, a large kitchen and dining area, den, and walk in pantry. There is an attached two story barn for storage, which leads into the recently built oversized 3 car garage with 12 foot doors, ideal for equipment or classic car storage. From this you can go to the 38x144 large dairy barn with stalls, horse paddocks, and hayloft, or the tremendous oversized dairy barn with 90 stanchions between the two barns, and main room upstairs, which could be converted into amazing space for those with vision. These are the best maintained functioning farm barns I have seen in 20 years. Add to that a full equipment shed, dairy processing area, approx 40 acres of pasture and fields, sugar house, pond, a network of trails, 60 acres of mature woodlands, and an idyllic home site at the crest of the upper field, and you have everything you could possibly want in a true Vermont farm property, with enjoyment and expansion potential for years to come. Recent updates include a new roof on the house, generator, and a full clean out. Don't sleep on this one of a kind opportunity. Property is in Current Use.

Listed by Michael Purcell of Berkley & Veller Greenwood/Dover

{$office->Name}

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.48% last updated on 2026-06-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Copyright 2026 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. Data last updated June 9, 2026 10:40 AM EDT

 

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