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Wallingford, VT Real Estate

Reflective ponds, perfectly rounded hills, long rural roads stretched through miles of green countryside and historic New England farms make up the quaint spectacle of Wallingford, VT. Our Wallingford real estate listings offer something for everyone. Large estates with expansive mountain views are often available, as are equally stunning Wallingford farmhouses converted to contemporary dream homes. Wallingford also offers prime land for building your own rural escape. In Wallingford, you'll enjoy access to Okemo Mountain, Killington and Interstates 89 and 91. 

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3654 West Hill Road Wallingford VT 05773

Wallingford, VT3654 West Hill Road

Price$2,750,000

Est. Mortgage: $/month

MLS Number 5015941

  • Residential Single Family
  • Full Bath 2
  • Address 3654 West Hill Road
  • Construction Existing
  • Bedrooms 3

Three Willows Farm is a classic Vermont farmstead on 103 acres in an area known for its historic properties, stone walls and open meadows on a dead-end gravel road. There are breathtaking, westward-facing views of a large pond and the Green Mountains, including Killington, Pico, and White Rocks. The circa 1850s Cape underwent a major renovation, artfully blurring the lines between traditional and contemporary with hand-hewn beams, wide pine floors, a stone fireplaces, and a gourmet kitchen. A newer wing was added, with a first-floor primary suite with its own stone fireplace. The screened-in porch extends the main living area, offering views of the extensive perennial gardens, and stunning sunsets in the evening. The guesthouse is a converted sugarhouse, which was moved to the property from a dairy farm. Dan Pratt of Robert Carlos Williams Associates was the architect for this delightful one-bedroom accommodation. A brook runs alongside that feeds into a small pond in front of the sugarhouse and a larger swimming pond below the house. The larger pond is stocked with trout yearly by the Rotary Club, which hosts an annual local youth fishing derby each summer. The barn has been transformed into a one-bay garage and workshop with a heated entertainment space above. There are approximately 20 acres of meadow, and the rest of the woodlands - including a sugarbush - are threaded with trails. Apple trees are located near the house. 13 minutes from dining; 45-50 from big mtn skiing.

Listed by T Story Jenks and Dia Jenks of LandVest,Inc/Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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2210 Sugar Hill Road Wallingford VT 05742

Wallingford, VT2210 Sugar Hill Road

Price$2,600,000

Est. Mortgage: $/month

MLS Number 5020176

  • Residential Single Family
  • Full Bath 2
  • Address 2210 Sugar Hill Road
  • Construction Existing
  • Bedrooms 4

Exceptional 6,000-sq ft timber frame sited on 27 secluded acres. This meticulously maintained, 5-star plus energy-rated home offers pretty mountain views from nearly every room. The 2-story great room features a soaring stone fireplace and floor-to-ceiling windows. Kitchen boasts a double oven, induction cooktop, granite center island, and rich cherry cabinetry. Dining room includes a built-in buffet with a wine fridge, while large sliders open to an inviting sunroom leading out to deck and fenced yard.The private primary suite includes a luxurious bathroom, generous walk-in closet, deck access, and mountain views. Upstairs, find 2 additional bedroom-also with views, a full bathroom, den and open loft. Practical mudroom w/ built-ins and laundry, and a stairway leading to an 800-square-foot bonus space above the garage, complete with a newly added bathroom. The expansive walkout comprises a wet bar, family room with a wood stove, a fourth bedroom, a climate-controlled wine room, and a home gym. Additional features include a 3-car garage with a dog shower and detached 2-car garage with second-story storage. Outside, gather around the patio's fire pit or relax by the 20x40 heated saltwater pool and adjacent pool house, equipped with a beverage kitchen and half bath. Enjoy peace of mind with state-of-the-art systems, including a backup generator, whole house ERV, humidifier, A/C, fiber and advanced security. Just 12 miles from Okemo and close to Rutland for shopping and services

Listed by Debra Staniscia of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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310 Hateful Hill Wallingford VT 05773

Wallingford, VT310 Hateful Hill

Price$2,000,000

Est. Mortgage: $/month

MLS Number 5014275

  • Residential Single Family
  • Full Bath 3
  • Address 310 Hateful Hill
  • Construction Existing
  • Bedrooms 4

Don't let the road name fool you, there is nothing to hate about this Robert Carl Williams grand estate and farm with stables. Nestled on a hilltop in East Wallingford, you will find one of the finest properties in the area with a nicely appointed 4 bedroom 5 bath house boasting 5 fireplaces, a historic huge barn, a run-in horse shelter, a Morton barn/riding arena, and a 5 bay carriage house/garage all surrounded by 145 acres consisting of pastures, trails, woods, lawns, and a pond. The home is finished with granite countertops, marble baths, AGA range cooking stove, indoor lap pool, sauna, hardwood floors, a grand staircase, and almost 360-degree views of mountains and valleys. Enjoy those views from one of several decks, including one off the primary bedroom, or the outdoor fireplace patio, The circa 1840 3-story barn with a slate roof is a masterpiece of historic engineering. From the craftsmanship of the posts and beams to the many stables, animal pens, and Dutch doors, this has so much potential. The large Morton building with double sliding doors on both ends makes a great riding arena or massive storage for all the toys. Many old roads and paths are still present so you can explore the many acres. The exterior of the home was freshly painted including the decks. Okemo Resort is about 12 miles away and the city of Rutland is about 15 minutes away. This property will not disappoint. Visit the Okemo real estate community today. Taxes are based on current town assessments.

Listed by Kevin Barnes of William Raveis Vermont Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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333 Creek Road Wallingford VT 05773

Wallingford, VT333 Creek Road

Price$1,699,000

Est. Mortgage: $/month

MLS Number 5015255

  • Residential Single Family
  • Full Bath 2
  • Address 333 Creek Road
  • Construction Existing
  • Bedrooms 3

Discover the pinnacle of Vermont life in the Mountains of Wallingford with clear views of Killington, Pico and White Rocks. Just minutes from some of the worlds best outdoor recreational sites with approximately 130 acres of fields, mountains, trails and woodlands. The grand two-story entry, featuring a wooden staircase and natural light, sets the stage for cozy, luxurious life in the Green Mountains. The formal living room, with its stunning fireplace and windows exudes sophistication, while opening itself to the large chef's kitchen and landscaped backyard. The formal dining room, family room and at-home office help to complete the traditional layout of the first floor. Upstairs, the master suite is a cozy getaway with a sitting area, and expansive master bath and two walk-in closets. Two additional bedrooms, a bathroom and spacious landing ensure plenty of space for everyone. Additional features include a two-car garage, at-home theater and a walk-out lower ground floor that is prepped and ready for a wet bar, recreational and more living space.

Listed by Max Walker of Watson Realty & Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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580 Sugar Hill Road Wallingford VT 05773

Wallingford, VT580 Sugar Hill Road

Price$875,000

Est. Mortgage: $/month

MLS Number 4997027

  • Residential Single Family
  • Full Bath 1
  • Address 580 Sugar Hill Road
  • Construction Existing
  • Bedrooms 3

Welcome to your dream equestrian estate!! This beautiful property is located in the heart of the Green Mountains and borders the Green Mountain National Forest along with the Long Trail (Appalachian Trail) with a perpetual easement for use of up to 20 more acres! This cape style home offers a great country kitchen with an open concept into the living room, three nice size bedrooms and a charming sunroom in the back! There is a attached 2 car garage and a oversized one car detached garage/workshop, perfect for storing all the farm toys! The expansive horse barn includes the potential for 17 stalls, tack & wash rooms and a hay loft! With many paddocks and pastures, a picturesque pond with spectacular mountain views, this truly is a slice of heaven! The 60'x120' indoor arena will offer you endless hours of riding, no matter what the Vermont weather may be! The possibilities are endless for the equestrian at heart! Call today for a private tour of this unique property!

Listed by Rhonda Nash of Welcome Home Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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25-85 Bear Mountain Road Wallingford VT 05742

MLS Number 5017988

  • Land
  • Acreage 23.1
  • Area VT-Rutland
  • Utilities None
  • PricePerSqFt 21038.96

Ready to enjoy seclusion? This property offers spectacular views from the the build site! The nearly 24 acre parcel offers privacy and convenience to the town of Wallingford for all of your essentials. Drive a bit further and you are in Rutland for shopping and other activities. Want to explore the local ski mountains? You are within 20-30 minutes of Okemo and within 45 minutes of Killington and Pico. This property has all infrastructure in place for your build. Recently the current home has burned down unfortunately and has been removed. This provides an easy start to your next build. Well, septic, electric and FIBER internet are all on site and ready! Bring your plans and start building and take advantage of the expansive views.

Listed by Flex Realty Group and Chris Williams of Flex Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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37 Cootey Lane Wallingford VT 05773

Wallingford, VT37 Cootey Lane

Price$450,000

Est. Mortgage: $/month

MLS Number 5023047

  • Residential Single Family
  • Full Bath 2
  • Address 37 Cootey Lane
  • Construction Existing
  • Bedrooms 3

Delightful well maintained home tucked away on 1.17+/- acre lot. 3 bedroom, 2.5 bath and a full basement. The fully applianced kitchen with a center island offers extra space for cooking, dining area with sliders leading out to the back yard makes it convenient for backyard bbq's. Off from the kitchen is the living room with built-ins enhanced by a propane fireplace. 9ft ceilings. A formal dining room borders the kitchen with a passthrough for food. Upstairs offers three bedrooms including a large primary bedroom and bath. Spacious backyard with an above ground swimming pool for summer fun and two sheds- one is a Garden Time Shed. Wired for a whole house generator and all exteriors are barried. Just minutes to Killington Ski area or Okemo Mountain for some of the best skiing in New England.

Listed by Nancy Greenwood of Watson Realty & Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1739 Vt Route 140 Wallingford VT 05773

Wallingford, VT1739 Vt Route 140

Price$445,000

Est. Mortgage: $/month

MLS Number 5010903

  • Residential Single Family
  • Full Bath 1
  • Address 1739 Vt Route 140
  • Construction Existing
  • Bedrooms 3

This MOVE-IN Ready 3 Bedroom, 3 Bathroom Cape nestled in the mountains just outside of Wallingford Village and within walking distance to White Rocks National Park and the Long Trail. 15 minutes to Jackson Gore! Mixed hardwood floors and natural light throughout the first floor. New Quartz countertops in the kitchen and charming light fixtures sets this cape apart! High Ceilings in the upstairs bedrooms make this home feel cozy and spacious at the same time. A fenced in yard sits just off of the 3 season porch. Enjoy morning coffee in the Ladybug Lounge with electricity overlooking the brook into the neighboring meadow. A spacious detached 2 car garage with storage overhead. Heat Pump, Pellet stove, generator ready. Make this Cape your new home or Vermont getaway. 15 minutes to Okemo!

Listed by Mark Noble of Welcome Home Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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331 Church Street Wallingford VT 05773

Wallingford, VT331 Church Street

Price$179,000

Est. Mortgage: $/month

MLS Number 5012240

  • Land
  • Address 331 Church Street
  • Acreage 3
  • Area VT-Rutland
  • Utilities None

Imagine your Vermont dream home perched perfectly atop the hill!! Enjoy the long range, western mountain views that offer a spectacular sunset any time of the year! This 3 acre property has tons of potential for your own secluded slice of heaven right here in the beautiful Green Mountains! Call today for a private tour and make those dreams come true!

Listed by Rhonda Nash of Welcome Home Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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000 Roger Hill Road Wallingford VT 05742

MLS Number 5020506

  • Land
  • Address 000 Roger Hill Road
  • Acreage 11.5
  • Area VT-Rutland
  • Utilities None

This slightly sloping 11.5+/- acreage lot is located in both Mount Holly and Wallingford Vermont at the end of a dirt road. Bring your plans and let your imagination run wild. Well-suited for a three-season camp.

Listed by Mendi Michael of Engel & Volkers Okemo

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Broker Reciprocity 

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. Data last updated February 7, 2025 4:11 PM EST