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View All Latest Woodstock 2500+ Sq. Ft. Properties for Sale
A chance awaits to acquire a brand-new, Vernacular Elevator Duplex Townhome with breathtaking views of Woodstock village rooftops and scenic Billings Museum Farm. This ra...
- 3 Beds
- 3 Baths
- 4986623 MLS
- CLOSED Status
EATON HOUSE- Steeped in history and ideally situated in Woodstock’s Historic District, the Eaton House is a handsome Greek Revival-inspired residence built in 1856. Set o...
- 5 Beds
- 3 Baths
- 5113873 MLS
- ACTIVE Status
Enjoy expansive views from every level of this beautifully updated, 3-bedroom, 3-full-bath Blake Hill condominium. As a highly desirable end unit, this property welcomes ...
- 3 Beds
- 3 Baths
- 5113057 MLS
- ACTIVE Status
2687 GARVIN HILL ROAD- Surrounded by the rolling hills and natural beauty of the Woodstock countryside, 2687 Garvin Hill Road offers a quintessential Vermont lifestyle on...
- 5 Beds
- 5 Baths
- 5112419 MLS
- ACTIVE Status
Located in the heart of the charming hamlet of South Woodstock, the iconic John Arnold Cottle House is widely considered one of Woodstock's finest early residences. Built...
- 5 Beds
- 4 Baths
- 5111700 MLS
- ACTIVE UNDER CONTRACT Status
SIGNIFICANT PRICE REDUCTION - SOUTH WOODSTOCK - HILLSIDE FARM estate presents an exceptional opportunity to embrace the quintessential Vermont country lifestyle on 10.1 p...
- 3 Beds
- 4 Baths
- 5111623 MLS
- ACTIVE Status
Privately set on 6.7 acres just three minutes from the Woodstock Village Green, this Greek Revival-inspired farmhouse offers views of Mount Tom and the Pomfret Hills. Bui...
- 4 Beds
- 5 Baths
- 5111035 MLS
- ACTIVE UNDER CONTRACT Status
Historic character, beautifully reimagined for modern Vermont living. Minutes from Woodstock Village, this extensively renovated four-bedroom home pairs the warmth and ...
- 4 Beds
- 3 Baths
- 5110412 MLS
- ACTIVE Status
Built in 1807 by Tille Parker, 26 The Green is one of Woodstock Village’s earliest and perhaps prettiest houses. The Federal style residence originally served as a tavern...
- 4 Beds
- 5 Baths
- 5107880 MLS
- PENDING Status
Lovely cottage nestled on the Ottauquechee River in the heart of historic Woodstock. Incredible river frontage with sprawling lawn for entertaining or just sitting enjoy...
- 4 Beds
- 3 Baths
- 5106838 MLS
- PENDING Status
Seller is Offering a $10,000 Credit at closing to buy down the interest rate or apply towards closing costs. Mountainside Road really leans into the Mountain get-away the...
- 5 Beds
- 4 Baths
- 5104119 MLS
- ACTIVE Status
This superbly cared-for cape-style home has been thoughtfully and comprehensively updated, with all bathrooms tastefully renovated with quality fixtures and finishes. The...
- 3 Beds
- 3 Baths
- 5103213 MLS
- CLOSED Status
"BLISS HOUSE" Privately nestled on a picturesque hillside just minutes from the Woodstock Village Green, this beautifully renovated residence offers exceptional privacy, ...
- 4 Beds
- 3 Baths
- 5102668 MLS
- ACTIVE UNDER CONTRACT Status
This wonderful Vermont Cape-style home is a peaceful hideaway with amazing views upriver towards Killington is within walking distance of Village shops, restaurants, and ...
- 4 Beds
- 3 Baths
- 5100512 MLS
- ACTIVE Status
Sorgenfrei, German for "carefree" captures the spirit of this remarkable 68 acre property in one of South Woodstock's most desirable locations: a place where life slows a...
- 3 Beds
- 4 Baths
- 5099532 MLS
- ACTIVE Status
Exceptional Views to Killington! Perched high on a private knoll and surrounded by open lush meadows and surrounded by antique stonewalls. This 5 bedroom, 4 bathroom ex...
- 5 Beds
- 6 Baths
- 5098424 MLS
- ACTIVE Status
OPEN HOUSE - SUNDAY 10/11 - 10:00AM TO 12:00PM. Perched high above the valley on 5 private acres, 81 Meadow Lane offers one of the most spectacular panoramic mountain vie...
- 5 Beds
- 4 Baths
- 5097556 MLS
- ACTIVE Status
Gracious Single Family home and Investment Opportunity - This 3 bedroom, 2 bath brick colonial is approx. 2,300+/- sq/ft with beautiful old wood flooring, newer kitchen, ...
- 4 Beds
- 4 Baths
- 5096963 MLS
- ACTIVE Status
Centrally located on the southwest side of the historic Woodstock Village Green, this classic c1840 Greek Revival farmhouse is one of the town’s finest residences. Loving...
- 6 Beds
- 8 Baths
- 5096089 MLS
- PENDING Status
Nestled in amongst flowering lilacs, ancient apple trees, and terraced English perennial gardens, this lovingly restored classic antique stone cape has all the convenienc...
- 4 Beds
- 3 Baths
- 5095556 MLS
- CLOSED Status
Kedron Valley Farm c1850: A classic beauty, perched on a knoll overlooking the idyllic hills and lush meadows of the valley with approx 32 acres. This stunning extended...
- 8 Beds
- 8 Baths
- 5094600 MLS
- ACTIVE Status
This beautifully renovated, truly move-in-ready home has been thoughtfully updated throughout including a brand-new kitchen, refreshed flooring, modernized bathrooms, fre...
- 3 Beds
- 3 Baths
- 5094379 MLS
- ACTIVE Status
Believed to be the oldest home in town, this remarkable c.1790 property offers a rare opportunity to own a piece of local heritage. Located in the town of Woodstock, and ...
- 5 Beds
- 3 Baths
- 5093544 MLS
- CLOSED Status
CURTIS HOLLOW FARM, Exceptional estate on the western edge of Woodstock offering 105 diverse acres bordering Calvin Coolidge State Forest. The updated main house features...
- 5 Beds
- 4 Baths
- 5091062 MLS
- ACTIVE UNDER CONTRACT Status
Just 2 miles from Woodstock Village, this gracious brick Cape on 6 open acres offers the perfect blend of privacy, comfort, and classic Vermont charm. Thoughtfully expand...
- 5 Beds
- 4 Baths
- 5089552 MLS
- ACTIVE Status
Great investment opportunity in the beautiful White Mountains. This could be strictly rental property or it could be your 2 bedroom home with 2 apartments for rental inc...
- 5089528 MLS
- CLOSED Status
Framed by groves of mature birch trees, a winding drive descends into a private valley surrounded by pastures, apple orchards, a spring-fed pond, and sweeping mountain vi...
- 5 Beds
- 4 Baths
- 5089158 MLS
- PENDING Status
This lovely four-bedroom, 2.5-bath cape features a two-car attached garage and a separate 700+/- sq. ft. one-bedroom apartment. The property also includes a separate outb...
- 5 Beds
- 4 Baths
- 5088406 MLS
- CLOSED Status
See the property specific website with video, 3-D tour and more. Set against the timeless beauty of Woodstock’s rolling countryside, this exceptional estate offers a rare...
- 4 Beds
- 4 Baths
- 5087228 MLS
- ACTIVE Status
Newly constructed Modern Vermont Farmhouse residence on 14 acres with absolutely amazing river views, 13-foot ceilings, gourmet kitchen, oversized french doors and window...
- 2 Beds
- 3 Baths
- 5084536 MLS
- ACTIVE Status
Historic Woodstock, Vermont - Spacious Home on Nearly 3 Acres. Welcome to a rare opportunity in the heart of Woodstock, one of Vermont’s most picturesque and sought-after...
- 4 Beds
- 3 Baths
- 5077210 MLS
- CLOSED Status
Set on a sun-bathed hillside between Woodstock Village and the renowned slopes of Killington and Pico, this custom-built Colonial captures what buyers seek most in Vermon...
- 4 Beds
- 3 Baths
- 5077012 MLS
- CLOSED Status
The Richmond House Unit B | Woodstock Village. An enduring Woodstock landmark, the iconic Richmond House (c.1826) is a proud brick Federal distinguished by its softly wea...
- 3 Beds
- 4 Baths
- 5076786 MLS
- ACTIVE Status
Charming property located just minutes from historic Woodstock Green. The main house first floor features 3 bedrooms/ 1bath with formal dining room, living room and kitc...
- 5 Beds
- 3 Baths
- 5074725 MLS
- CLOSED Status
Located in Woodstock, Vermont just one mile from the village green, the Alta House offers a rich quality of life filled with poolside sunsets, mountain vistas, proximity ...
- 3 Beds
- 5 Baths
- 5072035 MLS
- ACTIVE Status
Discover the charm of historic Woodstock in this beautifully maintained late-1800s residence, set on just over an acre of flat, open lawn and ideally located within walki...
- 4 Beds
- 4 Baths
- 5069833 MLS
- CLOSED Status
Beautifully sited just a short walk from Woodstock Village, this 2015 custom-built home blends modern comfort with timeless Vermont charm. Thoughtfully designed for every...
- 4 Beds
- 5 Baths
- 5069230 MLS
- CLOSED Status
This South Woodstock contemporary residence was designed by the original architect-owner to showcase Vermont’s changing seasons and capture views of the Kedron Brook as i...
- 4 Beds
- 3 Baths
- 5067285 MLS
- CLOSED Status
Gilbert’s Hill, the very best of Vermont living - Iconic, 112-acre estate with a storybook history as the first “modern” ski run in the US. Located two miles from the v...
- 6 Beds
- 5 Baths
- 5066205 MLS
- CLOSED Status
Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a...
- 3 Beds
- 4 Baths
- 5065230 MLS
- ACTIVE Status
Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a...
- 3 Beds
- 4 Baths
- 5065228 MLS
- ACTIVE Status
Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a...
- 3 Beds
- 4 Baths
- 5065227 MLS
- ACTIVE Status
Stunning contemporary extensively renovated and idyllically situated on a westerly facing hillside overlooking the village of Woodstock offers a coveted Woodstock locatio...
- 4 Beds
- 3 Baths
- 5064076 MLS
- CLOSED Status
Invite them all !! This 4 bedroom 4 bath condo spreads you out over 3 floors and offers Direct access and Views of the West Branch of the Pemigewasset River. The Associat...
- 4 Beds
- 4 Baths
- 4972721 MLS
- CLOSED Status
This historic home was built in 1904 by John Cotton Dana for his family around 1904. The Danas were a prominent family in Woodstock . The Dana House , home of the Woodst...
- 5 Beds
- 5 Baths
- 5002465 MLS
- CLOSED Status
Absolutely stunning, newly renovated residence, privately situated towards the end of a quiet town road in Woodstock, in an area of other substantial homes. Lovely mount...
- 4 Beds
- 5 Baths
- 5056790 MLS
- CLOSED Status
Open House Sunday, April 13, 12:00 to 2:00 - Tucked away in the serene forests of Woodstock, Vermont, this beautifully remodeled 11-room home offers 4 bedrooms, 4 bathroo...
- 4 Beds
- 4 Baths
- 5028430 MLS
- CLOSED Status
This lovingly maintained property with mountain views has been enjoyed by a single family since its construction in 1985. The open-concept layout is anchored by a stone R...
- 3 Beds
- 4 Baths
- 5022674 MLS
- CLOSED Status
Peaceful Gully Road Retreat. Just minutes from Woodstock Village. Set on 5.1 private acres along quiet and desirable Gully Road, this beautifully updated four-bedroom, tw...
- 4 Beds
- 3 Baths
- 5037463 MLS
- CLOSED Status
Located in the Heart of Woodstock Village- fantastic location at the foot of the Mtn Peg trail system with easy access to Vail field and all of towns amenities. This be...
- 4 Beds
- 4 Baths
- 5049138 MLS
- CLOSED Status
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, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated .
2500+ Sq. Ft. Woodstock Real Estate
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