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View All Latest Woodstock 2000+ Sq. Ft. Properties for Sale
This wonderful Vermont Cape-style home has overlooked the Ottauquechee River and the former Woodstock woolen mill (now the 'new' mill and community pools and recreation c...
- 4 Beds
- 3 Baths
- 5100512 MLS
- ACTIVE Status
Sorgenfrei German for "carefree" captures the spirit of this remarkable property in one of South Woodstock's most desirable locations: a place where life slows and the be...
- 3 Beds
- 4 Baths
- 5099532 MLS
- ACTIVE Status
On a small hill, amongst trees and beautiful gardens, sits this beautifully maintained log cabin with sweeping views of the surrounding mountains and river valley. Just ...
- 3 Beds
- 3 Baths
- 5098474 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
Live Work Play, Retire and Play, or Just Play on the Weekends and Holidays! This wonderful 3 BR, 3 Bath Townhome/Condo has it all. Nestled in a small quiet wooded comm...
- 3 Beds
- 3 Baths
- 5098210 MLS
- ACTIVE Status
OPEN HOUSE - Sunday July 12th - 10:00am to 2:00pm. Perched high above the valley on 5 private acres, 81 Meadow Lane offers one of the most spectacular panoramic mountain ...
- 5 Beds
- 4 Baths
- 5097556 MLS
- ACTIVE Status
If you've been dreaming of the quintessential Vermont lifestyle, this exceptional property delivers the perfect blend of privacy, charm, and convenience. Nestled on over ...
- 3 Beds
- 3 Baths
- 5097258 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
- ACTIVE UNDER CONTRACT Status
Spacious, immaculate, and beautifully maintained Federal-style brick townhouse located in the prestigious village of Woodstock, often recognized as one of America’s most ...
- 3 Beds
- 3 Baths
- 5095918 MLS
- ACTIVE 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
- ACTIVE Status
A rare Woodstock Village opportunity! A Victorian style home located in Woodstock's much desired Maple Street neighborhood! Popular Vail Field recreation area is convenie...
- 5095205 MLS
- ACTIVE 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, f...
- 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
- ACTIVE Status
Charming New Englander with Income-Producing Apartment in a Prime Location Well-maintained 4-bedroom, 3-bathroom New Englander-style single-family home featuring an atta...
- 4 Beds
- 3 Baths
- 5093238 MLS
- ACTIVE UNDER CONTRACT 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 Status
Enjoy the ease of townhouse living in this beautiful fully furnished end unit filled with natural light throughout. The setting is surrounded by woodlands and lovely la...
- 2 Beds
- 3 Baths
- 5090924 MLS
- ACTIVE UNDER CONTRACT Status
Excellent opportunity for residential or office/commercial space with easy access and high visibility on Rt 4 coming into town, Currently configured as office space down...
- 3 Beds
- 2 Baths
- 5089949 MLS
- ACTIVE 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
- ACTIVE UNDER CONTRACT 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
- ACTIVE UNDER CONTRACT Status
A rare Woodstock Village opportunity! A Victorian style home located in Woodstock's much desired Maple Street neighborhood! Popular Vail Field recreation area is convenie...
- 4 Beds
- 2 Baths
- 5088170 MLS
- ACTIVE 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
You know that feeling when you walk through a door and you can already see future memories being made? That's what you feel as you turn every corner of this gem. This tho...
- 3 Beds
- 2 Baths
- 5080038 MLS
- CLOSED Status
Fully furnished condo nestled in a small quiet community just 5 minutes from "Historic Woodstock". Super location! This unit is in very good condition- first floor com...
- 2 Beds
- 3 Baths
- 5077683 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
- ACTIVE 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
Set along East Woodstock Road with sweeping views across the Woodstock Valley, this thoughtfully renovated farmhouse pairs timeless Vermont character with a refined moder...
- 4 Beds
- 3 Baths
- 5075123 MLS
- CLOSED 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
Welcome to 33 Mountain Avenue – a mid-century modern gem poised perfectly on the edge of Faulkner Park and at the foot of Mt. Tom and once part of the Marianne Faulkner E...
- 2 Beds
- 4 Baths
- 5067740 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
Star Hill Farm is completely private, hidden on a hillside with pastoral and mountain views in the heart of South Woodstock. From the valley floor to the top of Meetingho...
- 7 Beds
- 10 Baths
- 5066210 MLS
- ACTIVE 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
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
- 5065225 MLS
- ACTIVE Status
Step back in time with this classic 1901 Gambrel-style residence, brimming with character and ready for your renovations and personal touch. Featuring 4 bedrooms and 3 ba...
- 4 Beds
- 3 Baths
- 5065029 MLS
- CLOSED Status
Stunning Views overlooking beautiful pastoral meadows as you gaze to the Pomfret Hills. This handsome condo has been completely renovated with cathedral ceilings accente...
- 3 Beds
- 3 Baths
- 5064977 MLS
- CLOSED Status
When you imagine life in the White Mountains, this charming home at 10 Bell Street brings that vision to life. Tucked into a quiet neighborhood in Woodstock, this propert...
- 3 Beds
- 2 Baths
- 5064203 MLS
- CLOSED 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
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 .
2000+ Sq. Ft. Woodstock Real Estate
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