104 Johnny Cake Hill Lane Readsboro VT 05350

Readsboro, VT104 Johnny Cake Hill Lane

Price$409,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5088576

Residential Single Family
Full Bath 2
Bedrooms 3
Bathroom 3
Square Feet 1,696

If you've been dreaming of peaceful country living with stunning views, this one-of-a-kind home on approximately 21 private acres in the hills of Southern Vermont is calling your name. Greet each morning with an awe-inspiring easterly panorama that, on clear days, stretches all the way to Mount Monadnock. This serene retreat offers the best of nature - birdsong in the morning, occasional wildlife sightings, and total tranquility. It's a true country oasis, built with love and vision by the current owner using timber milled from the very land it sits on. The hand-hewn beams give the home a warm, rustic character, seamlessly paired with modern conveniences for comfort and efficiency. Inside, the home features three bedrooms - two conveniently located on the main floor - and three bathrooms. The spacious living room invites relaxation with its charming soapstone wood stove, while the open dining area boasts panoramic views that will never grow old. The recently completed kitchen features quartz countertops and modern appliances. The home is well-equipped for sustainable living, with a Tesla battery backup system, energy-efficient mini-splits for heating and cooling, a new propane furnace, and a 2022 state-of-the-art septic system. Step outside to the expansive deck, where you can sip your morning coffee or unwind at sunset, soaking in the beauty and peacefulness of your surroundings. This property offers everything to embrace the best of country living. This home is on a quiet class 4 road. The town does not plow in the winter; therefore the owner would need to have it plowed themselves.

Listed by Monica Sumner of BHG Masiello Brattleboro

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.

Bennington, VT23 Pageant Street

Price$399,900The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5088223

Residential Single Family
Full Bath 1
Address 23 Pageant Street
Bedrooms 4
Bathroom 2

This c. 1936 4BR/2BA home has been beautifully updated to blend timeless architectural character with modern comfort and convenience. Meticulously maintained throughout, it features gleaming hardwood floors, vintage details and thoughtful updates designed for today's lifestyle. The stunning granite kitchen offers rich cherry cabinetry and stainless steel appliances, all new in 2024, creating a warm and functional space for cooking and gathering. The expansive primary suite is a true retreat, complete with an oversized walk-in shower, double vanity with granite countertop, and abundant space to unwind. Three additional guest bedrooms and a full guest bath provide flexibility for family, guests, or home office needs. The finished attic is perfect for a playroom or creative space and the home offers abundant storage throughout. Step outside to enjoy the brand-new expansive deck overlooking the yard, along with a shed and additional outbuilding for hobbies, gardening, or extra storage. Located in the Clarks Woods neighborhood, this charming home is convenient to the country club, hospital, and other local amenities while offering the comfort of a lovely residential setting. 0.33 acre.

Listed by Vicki Wilson of Maple Leaf Real Estate

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.

100 McCarthy Acres Road Shaftsbury VT 05257

Shaftsbury, VT100 McCarthy Acres Road

Price$399,000The price has recently decreased

Est. Mortgage: $/month

Pending

MLS Number 5053470

Residential Single Family
Full Bath 3
Village North Bennington
Bedrooms 5
Bathroom 3

Nearly Lakefront Living in the Heart of North Bennington! Come for the space-stay for the location! This spacious home offers over 2,500 sq. ft. of living space, including 5 bedrooms, 3 full bathrooms, a large home office in the finished basement, and a versatile 250 sq. ft. bonus room attached to one of the upstairs bedrooms. The original garage has been thoughtfully transformed into a 600 sq. ft. primary suite, featuring energy-efficient mini-split heating and cooling, with a large main bedroom and an adjoining space ideal for a walk-in closet or private retreat. A new steel two-car garage was added, ensuring your vehicles stay protected year-round. The property's outdoor space is just as impressive-with beautifully maintained perennial gardens (featuring lilacs, peonies, lilies, and phlox), fruit trees (peach and plum), and graceful white birches. A small backyard storage shed with electricity adds extra convenience. Located just steps from picturesque Lake Paran and nestled in the charming Village of North Bennington, this home offers the perfect balance of peaceful village life and easy access to nearby commercial areas. Plus, inclusion in the North Bennington Graded School District allows PreK-6th grade students to attend an approved independent or private school tuition-free. Don't miss the opportunity to enjoy this rare combination of space, location, and community!

Listed by Nicholas Charest of Maple Leaf Real Estate

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

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Price	Down Payment	Interest Rate	Years
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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.

Manchester, VT446 Highland Avenue

Price$399,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5079187

Residential Single Family
Full Bath 1
Address 446 Highland Avenue
Bedrooms 3
Bathroom 1

Looking for a unique opportunity for equity growth? This is it! Location, location, location. Highly desirable Highland Avenue is one of those rare streets with character homes that is literally only a few walking blocks to town. If you are lucky enough to own this charming 3- bedroom home offering 1,663 sq ft of living space, you will enjoy easy access to the library, local shops, coffee spots, and restaurants right at your doorstep.This home already checks the important boxes; location, size, character, generous living space, and flexible layout. What it has room for is your personal customization and updating. And that is exactly why you should own it. Whether you are a first-time buyer, investor, or someone looking to create your dream home in a prime location, this property offers exceptional potential. Being offered at an entry level price for a high end market, room for growth is there. Here is the best part. When you need a break, you can relax in your charming garden complete with Koi Pond and let your cares drift away. Enjoy life at its best with Manchester schools, Burr and Burton Academy, a short drive to ski areas, summer hiking and more. Any one who understands Manchester will recognize the amazing opportunity waiting here. Don't miss the chance to bring your vision to life! Ask to see a copy of the pre-listing inspection report so you have a head start. Need more ideas? Check out the virtually staged photos to get you started.

Listed by Sunny Breen of Josiah Allen Real Estate, Inc.

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

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Price	Down Payment	Interest Rate	Years
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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.

Arlington, VT515 Buck Hill Road

Price$399,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5093425

Residential Single Family
Full Bath 1
Address 515 Buck Hill Road
Bedrooms 3
Bathroom 1

OPEN HOUSE SATURDAY 6/13 9am to 2pm. Completely renovated from top to bottom, this move-in-ready home perfectly blends modern updates with classic Vermont charm. 3 bedrooms and 1 bathroom with a layout that includes multiple practical options for adding a second bathroom. The layout also includes a unique, unfinished bonus area off the primary bedroom with its own private staircase to the backyard-a blank canvas ideal for an expanded suite, home office, or studio, and a back enclosed porch continues to present many options to suit your own living needs. Tucked away in a desirable neighborhood setting, the thoughtfully positioned lot offers a surprising level of peace and privacy. Nestled between the Green Mountains and the Taconic Range, Arlington is famed for its scenic beauty, historic covered bridges, and world-class recreation on the Batten Kill River, putting hiking, biking, and fly-fishing right at your doorstep. The location is hard to beat with the quick access to Historic Route 7A and Route 7 to get to several shire towns and ski resorts.

Listed by Lori Hurley of Four Corner Properties LLC

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

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Price	Down Payment	Interest Rate	Years
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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.

1260 Cider Mill Road Shaftsbury VT 05262

Shaftsbury, VT1260 Cider Mill Road

Price$397,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5084055

Residential Single Family
Full Bath 2
Address 1260 Cider Mill Road
Bedrooms 2
Bathroom 2

Tucked away on a peaceful country road in Shaftsbury, this 2-bedroom, 2-bath contemporary ranch offers the perfect balance of privacy and convenience-just 10 minutes to Bennington. Set on 1.5 acres, the home features easy one-level living with an open, light-filled layout. The heart of the home is the bright, sunny kitchen with ample workspace and modern finishes. The spacious primary suite includes a private ensuite bath and a generous walk-in closet, while a comfortable guest bedroom is paired with a full bath-ideal for visitors or flexible use. Enjoy indoor/outdoor living with a wrap-around deck that perfect for relaxing or entertaining. A versatile entry space, currently used as a mudroom, offers excellent potential to be converted into a charming 3-season porch. Additional highlights include a dedicated laundry room and an oversized detached two-car garage that is fully heated-ideal for year-round use, hobbies, or extra storage. Surrounded by a tranquil country setting with room to relax, garden, or unwind, this property offers the best of Vermont living while remaining close to dining, shopping, and amenities in nearby Bennington.

Listed by Vicki Wilson of Maple Leaf Real Estate

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

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Price	Down Payment	Interest Rate	Years
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Est. Mortgage: $/month

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

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231 Washington Avenue Bennington VT 05201

Bennington, VT231 Washington Avenue

Price$395,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5084174

Residential Single Family
Bedrooms 3
Bathroom 2
Square Feet 1,556
Acreage 0.20

Charming vintage 1920s Arts & Crafts-style cottage in a prime village location. This inviting home offers seven main rooms, including three bedrooms and two baths, blending timeless character with modern comfort. The updated kitchen features abundant storage and flows nicely into the living spaces, highlighted by beautiful wood floors and a cozy fireplace. Central air ensures year-round comfort. Enjoy outdoor living with a large, inviting front porch perfect for relaxing, as well as a private back deck ideal for entertaining or a quiet retreat. A two-car detached garage adds convenience and additional storage. Classic architectural details and thoughtful updates make this a truly special property in a highly desirable setting.

Listed by Kelley McCarthy of Mahar McCarthy Real Estate

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

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Price	Down Payment	Interest Rate	Years
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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.

317 Chester Knoll Drive Bennington VT 05201

Bennington, VT317 Chester Knoll Drive

Price$388,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5092590

Residential Single Family
Full Bath 2
Bedrooms 4
Bathroom 2
Square Feet 1,620

Brand New Construction in Bennington! Looking for the perfect blend of modern comfort, energy efficiency, and outdoor adventure? This stunning new construction home has it all! Featuring 4 spacious bedrooms, 2 full baths, and thoughtfully designed living spaces, this home was built with today's lifestyle in mind. Enjoy lower utility costs and year-round comfort thanks to its energy-efficient construction. Step outside onto the expansive back deck, the perfect place to host summer barbecues, sip your morning coffee, or unwind while taking in the peaceful surroundings. Love the outdoors? You'll appreciate the nearby walking trails that connect you to the beautiful grounds of the Bennington Museum and beyond. Plus, you're just minutes from the hospital, shopping, dining, and everything Bennington has to offer. ?? Brand New Construction ?? 4 Bedrooms | 2 Bathrooms ?? Energy Efficient Design ?? Huge Rear Deck ?? Walking Trails Nearby ?? Convenient Location Close to Shopping & Healthcare This is more than a house-it's a lifestyle. Agent is seller.

Listed by Lillian West of Maple Leaf Real Estate

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

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Price	Down Payment	Interest Rate	Years
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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.

Arlington, VT4991 VT Route 313

Price$375,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5076632

Residential Single Family
Full Bath 1
Address 4991 VT Route 313
Bedrooms 3
Bathroom 2

Nestled in the heart of Vermont's picturesque Battenkill Valley, this charming three-bedroom, two-bath Cape offers the perfect blend of natural beauty and timeless New England character. Framed by sweeping views of the Green Mountains and just a stone's throw from the renowned fly-fishing waters of the Battenkill River, this property is an idyllic retreat for outdoor enthusiasts and serenity-seekers alike. Inside, warm hardwood floors create an inviting atmosphere, while an expansive back deck provides the perfect space to relax, entertain, and take in the surrounding mountain views. A huge oversized two-car garage offers exceptional storage and convenience. Energy-efficient upgrades include a newer boiler, newer roof and solar panels, ensuring low-cost, sustainable living without compromising comfort. Adding to its unique appeal, the home is located near the historic studio of Norman Rockwell, enriching the setting with a touch of artistic heritage. With easy access to neighboring towns in both Vermont and New York, the location offers exceptional convenience for commuting, exploring, or simply enjoying all the region has to offer. A must-see property in a truly picturesque setting, this home captures the very essence of Vermont country living-charming, peaceful, and beautifully connected to nature. 20 minutes to Manchester and 30 minutes to the slopes. Don't miss this opportunity! Call today.

Listed by Margretta Fischer of Wohler Realty Group

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

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Price	Down Payment	Interest Rate	Years
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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.

Sandgate, VT3510 Rupert Road

Price$375,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5084027

Residential Single Family
Full Bath 1
Address 3510 Rupert Road
Bedrooms 2
Bathroom 1

Beautifully maintained and truly one-of-a-kind, this "Very Vermonty!" 2-bedroom residence offers the perfect blend of charm, comfort, and functionality. Set above a spacious garage, the home is in mint, immaculate condition and designed for easy living. Inside, you'll find a warm and inviting interior complemented by mini-split systems for efficient heating and cooling. Every detail reflects pride of ownership, making this a true turnkey opportunity. Ideal for outdoor enthusiasts, the oversized garage provides ample storage for all your toys-whether it's vehicles, equipment, or recreational gear. Step outside and take in the breathtaking setting, featuring outrageous mountain views, a peaceful waterfall, and a small pond that adds to the property's natural beauty and serenity. Whether you're looking for a getaway or a full-time residence, this unique offering delivers rustic elegance in a stunning location.

Listed by Faith Rhodes of Maple Leaf Real Estate

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

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