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Windham County

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65 Cedar Street Brattleboro VT 05301

Brattleboro, VT65 Cedar Street

Price$339,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5093467

  • Residential Single Family
  • Full Bath 2
  • Address 65 Cedar Street
  • Bedrooms 4
  • Bathroom 2

Step into a world of artistic whimsy and historic allure at 65 Cedar Street, a property overflowing with character, magic, and boundless potential. Nestled in an ideal location with an entrance to the beloved Retreat Trails, this unique home offers an enchanting escape from the everyday. Outside, the property is embraced by beautiful, mature gardens cultivated over time in a spirit of enchanting "benign neglect"-where nature and romance intertwine to create a storybook setting that will capture your heart from the moment you arrive. Inside, you will find a spacious layout featuring 4 bedrooms and 2 full baths spread across 2,250 square feet of versatile living space. The home has been thoroughly cleaned out and deep-cleaned, presenting a pristine, blank canvas with exceptional, rock-solid "bones" ready for its next chapter. Fine historic details anchor the home, from rich wood floors to timeless built-ins. At the heart of the home sits a magnificent centerpiece: a vintage Vermont Iron Stove Works stove, radiating authentic New England warmth and charm. The footprint continues to impress with a bright, beautiful sunroom perfect for morning coffee, a large attached 2-car garage providing excellent storage, and a expansive bonus space tucked away in the finished attic. This property is being offered in "as-is" condition and does not include appliances, making it the ultimate dream project for those looking to invest sweat equity into a truly remarkable historic home. Bring your vision to finish the cosmetic upgrades and unlock the true grandeur of this whimsical masterpiece. OPEN HOUSE SUNDAY, JUNE 14TH | 12:00 PM - 2:00 PM Come experience the magic and explore the incredible potential of this one-of-a-kind home in person!

Listed by Kate Barry of EXP Realty

{$office->Name}

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.

92 Wardon Road Putney VT 05346

Putney, VT92 Wardon Road

Price$335,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5087300

  • Residential Single Family
  • Full Bath 1
  • Address 92 Wardon Road
  • Bedrooms 4
  • Bathroom 2

Distinctive and thoughtfully designed, this four-bedroom home is set in desirable Putney just minutes to town. The open-concept living room, kitchen, and dining area create a bright, stylish gathering space that feels both modern and inviting. The 4 bedroom layout includes 1 1/2 baths and the 4th bedroom could be used for remote work, creative pursuits, or guest overflow. Large windows bring in natural light and highlight the home's unique character and comfortable flow. Situated on 10 acres, the property offers privacy and room to explore, garden, or simply enjoy the peaceful surroundings. A rare blend of distinctive design and country setting, this Putney property is just minutes from town amenities while feeling like a private retreat. OPEN HOUSE SATURDAY 5/9 11AM-1PM.

Listed by John Hatton and Claire Renaud of Berkley & Veller Greenwood Country

{$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.

6 Sycamore Street Brattleboro VT 05301

Brattleboro, VT6 Sycamore Street

Price$335,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5091728

  • Residential Single Family
  • Full Bath 1
  • Address 6 Sycamore Street
  • Bedrooms 4
  • Bathroom 1

Located in one of Brattleboro's desirable neighborhoods, this inviting 4-bedroom home offers a comfortable layout, great natural light, and convenient access to schools, parks, trails, shopping, and downtown amenities. The bright living room features a large bay window that fills the space with natural sunlight, while the kitchen offers ample cabinet space and overlooks the backyard. With two bedrooms and a full bathroom on the first floor, the layout offers flexibility for a variety of living needs. Outside, enjoy a spacious backyard with room to garden, gather, or simply relax. A warm and welcoming home ready for its next chapter. Open house Saturday, 5/30 from 1-3 and Sunday 5/31 from 11-1

Listed by Wendie Wright of Coldwell Banker LIFESTYLES - Hanover

{$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.

3730 Route 100 Wardsboro VT 05355

Wardsboro, VT3730 Route 100

Price$330,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5038215

  • Residential Single Family
  • Full Bath 2
  • Address 3730 Route 100
  • Bedrooms 4
  • Bathroom 4

Property is being sold "as is where is" and does need some TLC. The house is set back off the road quite a bit for total privacy and there is a pond on the property. There is a one car garage, a full daylight basement, and a sun room. Sellers have given permission to encourage all offers. Property was originally listed for $450,000 but the sellers have reduced the price to $350,000. The tax map indicates that are 16.6 acres while the deed indicates that there are 15+/-.

Listed by Ginny Read of Read Realty LTD

{$office->Name}

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

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Do not fill in this field:

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.

1192 Chapel Hill Road Whitingham VT 05361

Whitingham, VT1192 Chapel Hill Road

Price$329,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5058111

  • Residential Single Family
  • Full Bath 2
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,840

Discover Vermont living at its finest in this architecturally unique round home, set on a 1-acre lot. Included in the sale is an additional 1-acre parcel directly across the street, offering potential for a garage, guest house, or Airbnb. Buyers should perform their own due diligence, as seller and broker make no representation on buildability. Step inside and walk into the welcoming lower level, where you'll find three restful bedrooms and a spacious bathroom featuring a jetted tub, tiled floors, and a glass-enclosed shower-perfect for unwinding after a day in the mountains. Head upstairs to the main level and enjoy the wide-open floor plan, where the kitchen, dining area, and living room flow together seamlessly. A cozy wood burning fireplace anchors the space, while a door opens to a sunny deck ideal for morning coffee, evening gatherings, or simply soaking in the peaceful surroundings. This turnkey home is fully furnished and ready for you to move right in. Whether you're here for adventure or relaxation, the location offers it all-ski or hike at Mount Snow or Berkshire East, explore the VAST snowmobile trails, golf at Haystack or Mount Snow, or take in the dining and cultural scene of the Berkshires, all just minutes away. Whether you're looking for a vacation retreat or a year-round sanctuary, this property delivers the quintessential Vermont four-season lifestyle. Don't miss this rare opportunity, schedule your private showing today!

Listed by Cliff Leinonen and Cindy Leinonen of Four Seasons Sotheby's Int'l Realty

{$office->Name}

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.

119 Forest Street Brattleboro VT 05301

Brattleboro, VT119 Forest Street

Price$329,000The price has recently decreased

Est. Mortgage: $/month

Pending

MLS Number 5083243

  • Residential Single Family
  • Full Bath 1
  • Address 119 Forest Street
  • Bedrooms 3
  • Bathroom 1

Great location in the heart of Brattleboro. This 3-bedroom, 1-bathroom Jewel of a home is as efficient as it is charming. Very well maintained, with gorgeous maple floors, built-ins, original natural woodwork, elegant marble countertops, and an open kitchen/dining/living space that shines with a southern exposure. Snug little wood stove adds to the uplifting spirit in this home. Large upstairs bedrooms and an impressive attic space with great potential for finishing. Enjoy your front covered porch and expansive back deck with pretty views of Mount Wantastiquet and organic vegetable beds the current owner has cultivated. There have been many fine updates, like a new 2025 oil tank, a new 2025 chimney liner, a woodstove, and more. This sweet home also has a detached garage and a walk-out basement with enclosed storage. If you are seeking a stylish in-town home, this may be it! Close proximity to downtown, to enjoy our vibrant art scene, year-round farmers market, eclectic restaurants, and our proud, strong, culturally diverse community. If you like to explore, you can catch the nearby retreat meadows entrance and hike away! Showings start Friday, April 17th by appointment.

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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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.

408 Old Guilford Road Brattleboro VT 05301

Brattleboro, VT408 Old Guilford Road

Price$329,000The price has recently decreased

Est. Mortgage: $/month

Pending

MLS Number 5086000

  • Residential Single Family
  • Full Bath 1
  • Bedrooms 3
  • Bathroom 1
  • Square Feet 1,480

This is the first time this home is being offered for sale. Owned and maintained by the same owner for the past 46 years! This home is hidden from the road. Enter via the Right of Way and the land opens up into a lovely private, garden filled yard. This property abuts the Fort Dummer State Park, so you've got miles of trails in your back yard! The ranch style living offers an open concept kitchen/dining/living area with 3 bedrooms and a full bath on one level. Downstairs there is an additional finished room and large concrete basement. A perimeter drain surrounds the house and the home comes with a generator. No drivebys because you cannot see the house from the road. There is highway white noise.

Listed by Victoria Woods of Brattleboro Area Realty

{$office->Name}

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

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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.

550 South Main Street Brattleboro VT 05301

Brattleboro, VT550 South Main Street

Price$329,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5086341

  • Residential Single Family
  • Full Bath 1
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,280

Lovely level lot, close to schools, hospital, shopping, State park and downtown. The best of everything, and BRAND NEW!!! Be the the envy of all your friends, with this wonderful, open concept, one level home. Primary bedroom on one end with an ensuite for privacy! New, shiny appliances, good sized island for cooking or hanging out and both a tub and a walk in shower. Special in so many ways, easy to show.

Listed by Christine Lewis of Brattleboro Area Realty

{$office->Name}

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

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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.

255 Guilford Street Brattleboro VT 05301

Brattleboro, VT255 Guilford Street

Price$329,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5088378

  • Residential Single Family
  • Full Bath 1
  • Address 255 Guilford Street
  • Bedrooms 3
  • Bathroom 2

Looking for your first home - or ready to downsize? THIS ONE IS FOR YOU! Ideally located just outside the bustle of town yet close to everyday conveniences, this efficient ranch with daylight basement comes with a fantastic 24' x 24' detached garage - perfect for hobbyists, collectors, or simply keeping vehicles protected. Set on a half acre and minutes from Memorial Park, shopping, schools, the hospital, and I 91, this property delivers tremendous value at a competitive price point. The main level features an expansive kitchen that opens to the dining/living room and flows onto a massive 36' x 11' deck - ideal for entertaining or relaxing outdoors. A primary bedroom with adjoining full-bath, and an additional bedroom or office complete the first floor. The lower level adds even more flexibility with a third bedroom or office with adjoining ¾-bath, a large family room, a mudroom entry, and a utility/laundry room. There's room to play, garden, and enjoy the outdoors, all while benefiting from an efficient footprint and an easy, open floor plan. With a great location, versatile layout, and standout garage, this home checks all the boxes. Don't let it get away. Showings begin 5/17/26

Listed by Dan Normandeau of Berkley & Veller Greenwood Country

{$office->Name}

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

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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.

16 Washington Street Brattleboro VT 05301

Brattleboro, VT16 Washington Street

Price$325,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5024828

  • Residential Single Family
  • Full Bath 3
  • Address 16 Washington Street
  • Bedrooms 5
  • Bathroom 3

Fabulous potential with this in-town home on a great neighborhood street just a few short minutes to downtown Brattleboro where you'll find shops, restaurants, galleries, and more! Close to the hospital, schools, and points north and south with easy access to Rt 91. This home retains much of the original woodwork with bulls eye trim for the doors, an elegant staircase with two stained glass windows, and glowing wood floors. First floor has a bedroom option and a full bathroom, there's a full bathroom on each floor! Plenty of room for everyone with three more bedrooms and a bathroom on the second floor. There is an additional room on the second floor with separate entrance that would make a great office, and the third floor offers an in-law potential with a one bedroom studio apartment. There are two furnaces and two oil tanks, one for the first floor, one for the second floor, and a propane wall unit for the third floor.

Listed by Rebecca Seymour of Brattleboro Area Realty

{$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 4:24 PM EDT

 

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