Wallingford Real Estate

Wallingford is a town in Rutland County, Vermont. The town contains the villages of East Wallingford and South Wallingford. Several outdoor activities are available in and around Wallingford. Places include the Green Mountain National Forest, which features scenic cliffs, trails and waterfall hikes, as well as, Litlle Rock Pond for swimming and camping. Wallingford is also conveniently located near Okemo Mountain Resort.

Discover current real estate for sale in Wallingford, Vermont. If you have any questions or if you'd like to see any of these properties in person, call 802-793-2002 or contact us online.

Create a free account to save your favorite Vermont real estate listings and get notified when similar properties become available.

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
  • County Rutland
  • Property Type Single Family
  • Bedrooms 4
  • Bathroom 6

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: 6.87% last updated on Feb 13, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

310 Hateful Hill Wallingford VT 05773

Wallingford, VT310 Hateful Hill

Price$2,000,000

Est. Mortgage: $/month

MLS Number 5014275

  • Residential Single Family
  • County Rutland
  • Property Type Single Family
  • Bedrooms 4
  • Bathroom 5

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: 6.87% last updated on Feb 13, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

333 Creek Road Wallingford VT 05773

Wallingford, VT333 Creek Road

Price$1,699,000

Est. Mortgage: $/month

MLS Number 5015255

  • Residential Single Family
  • County Rutland
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 4

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: 6.87% last updated on Feb 13, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

580 Sugar Hill Road Wallingford VT 05773

Wallingford, VT580 Sugar Hill Road

Price$875,000

Est. Mortgage: $/month

MLS Number 4997027

  • Residential Single Family
  • County Rutland
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 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: 6.87% last updated on Feb 13, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

370 Hillside Road Wallingford VT 05773

Wallingford, VT370 Hillside Road

Price$674,900

Est. Mortgage: $/month

Active With Contract

MLS Number 5020308

  • Residential Single Family
  • County Rutland
  • Property Type Single Family
  • Bedrooms 4
  • Bathroom 3

Meander up your own winding driveway to discover this stately, one-level executive home, nestled at the end of a quiet road on a secluded 8.9-acre oasis. Featuring a large private pond, a guest house, and timeless mid-century elegance, this 2800-square-foot home is a rare gem that seamlessly blends 1960s sophistication with modern comfort. Inside, bold architectural lines, expansive windows, and a tasteful mix of stone and wood bring character to every corner. The open layout flows effortlessly, creating both inviting and functional spaces. Cozy up by one of two wood-burning fireplaces, where natural materials provide warmth and ambiance, or enjoy the oversized sunken great room with vaulted ceilings and a dramatic floor-to-ceiling stone fireplace. A spacious kitchen invites family gatherings, while the formal dining room offers a space for special meals. Relax in the knotty pine-paneled den, or entertain in the attached screened porch, overlooking your serene landscape. The three family bedrooms each offer unique character and scenic views, while the primary suite, located in the east wing, provides a tranquil retreat. This property offers unparalleled privacy just minutes from the charming town of Wallingford, VT, and is ideally located near some of Vermont's most sought-after destinations. Enjoy a 25-minute drive to Manchester's upscale dining and shopping, or take a scenic ride to Woodstock's farmers market. Great skiing at Killington and Okemo Mountain too. LIVE VERMONT.

Listed by Freddie Ann Bohlig of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.87% last updated on Feb 13, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

25-85 Bear Mountain Road Wallingford VT 05742

MLS Number 5017988

  • Land
  • County Rutland
  • Square Feet 1,006,236
  • Acreage 23.1

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: 6.87% last updated on Feb 13, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

37 Cootey Lane Wallingford VT 05773

Wallingford, VT37 Cootey Lane

Price$450,000

Est. Mortgage: $/month

MLS Number 5023047

  • Residential Single Family
  • County Rutland
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 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: 6.87% last updated on Feb 13, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

1739 Vt Route 140 Wallingford VT 05773

Wallingford, VT1739 Vt Route 140

Price$439,000

Est. Mortgage: $/month

MLS Number 5010903

  • Residential Single Family
  • County Rutland
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 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: 6.87% last updated on Feb 13, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

123 Vermont Route 155 Wallingford VT 05742

MLS Number 5028871

  • Residential Single Family
  • County Rutland
  • Property Type Single Family
  • Bedrooms 5
  • Bathroom 2

Welcome to River View Cottage! Step into history with this beautifully preserved and thoughtfully updated multi-level home. Built in 1900 it offers both a rare blend of classic charm and modern comforts to include vinyl siding and all new insulated windows. Nestled in a picturesque small Village of East Wallingford, this riverfront home boasts direct river frontage, which provides stunning views and the soothing sounds of nature right from your doorstep. Inside, discover a warm and inviting layout featuring original woodwork, beautifully refinished wide-plank wood floors and modern updates for today's lifestyle. The multi-level design offers versatile living spaces, perfect for relaxing or entertaining, and has bedrooms on both the main floor and the second floor. Located just a short drive to Okemo Mountain Resort, this home is an ideal year-round getaway perfect for skiers, snowmobilers, outdoor enthusiasts or those seeking a serene escape with small-town charm. Whether you're looking for a primary residence, vacation retreat, or investment property, this riverfront gem is a rare find. So if you are looking for peaceful river views while sipping a cup coffee on the covered front porch or just unwind after a day on the slopes then this one is a must see. Welcome Home!

Listed by Joshua Lemieux of Remax Summit

$
$
%
$/month over payments
Federal 30-year interest rate: 6.87% last updated on Feb 13, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

331 Church Street Wallingford VT 05773

Wallingford, VT331 Church Street

Price$179,000

Est. Mortgage: $/month

MLS Number 5012240

  • Land
  • County Rutland
  • Square Feet 130,680
  • Acreage 3

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: 6.87% last updated on Feb 13, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

000 Roger Hill Road Wallingford VT 05742

MLS Number 5020506

  • Land
  • County Rutland
  • Square Feet 500,940
  • Acreage 11.5

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: 6.87% last updated on Feb 13, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

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 17, 2025 8:22 AM EST