New Listing! Wolfeboro NH Home for sale $1,650,000 $438 per sq.ft.

$1,650,000 $438 per sq.ft. Wolfeboro NH Home »

6 Beds | 4 Baths |   Total Sq. Ft. 3766  |  Acres: 3.22
Listed on Wednesday Apr 15, 2026
Description: Grand 1840 Historic Colonial, known as "Wellsweep" in days gone by. Beautifully appointed with all contemporary conveniences yet preserved antique charm. Step inside to enjoy vintage luxury, warmth, and elegance. Private 3.2-acre setting abutting the Kingswood Golf Course. The inground pool with large pergola and private back yard porch and patio superbly complements the inviting indoor amenities. A large stately wrap-around porch is waiting for your iced tea and lemonade, so relaxing, just as the one and only Grace Kelly enjoyed right on that very porch, with a view toward the lake, hills and gorgeous sunsets! Even though situated on South Main Street, the experience once you have arrived is very private and secluded. Many substantial upgrades are listed in the Disclosure attachment, including a new 6-bedroom septic system, roof, central air, appliances, etc. totaling over $200,000. Beautiful hardwood floors throughout the first floor, formal front staircase and back servant staircase to the second floor speaks of the elegant past. Primary bedroom and ensuite with double vanity on the second floor in the rear of the house affords peace and quiet also. Detached, oversized garage with heated workshop. Beautifully maintained grounds with stately, mature trees. Minutes to private town, resident only beaches on Lake Winnipesaukee, marinas, fine dining, skiing, and all that Wolfeboro and the Lakes Region has to offer. OPEN HOUSE Saturday 10AM - 2PM See Listing Details & 60 images. Includes a Virtual Tour

$1,689,000 $404 per sq.ft. Village of North Wolfeboro in Town of Wolfeboro NH Home »

Waterfront on Lake Winnipesaukee
4 Beds | 4 Baths |   Total Sq. Ft. 4181  |  Acres: 4.8
Listed on Thursday Mar 26, 2026
Description: Fully refurbished throughout! Wolfeboro country estate prioritizing privacy and luxury with surrounding mountain views and an in-ground pool with cabana. This stunning home is set atop a quiet knoll surrounded by classic New England stone walls and 4.8 acres. The residence itself presents a thoughtful layout with four bedrooms, including the unique flexibility to choose a primary suite on either the first or second floors with updated master baths. The heart of the home is a brand-new, custom light-cherry kitchen, redesigned with quartz countertops, abundant custom cabinetry, and a spacious pantry. Upstairs, a dedicated entertainment level awaits with a full wet bar, separate media room, and game room. Three fireplaces--two propane and one wood-burning--provide warmth and ambiance, while multiple balconies and patios invite you to soak in the ever-changing scenery. Beyond the walls, your private oasis unfolds. The centerpiece is a heated Gunite pool and spa, reconditioned in 2025, accompanied by a convenient pool house with an outdoor shower. Practical luxury is ensured with a heated garage featuring new epoxy flooring, a whole-house generator, and comprehensive air conditioning, preparing you for year-round comfort. Every detail has been carefully considered, creating not just a home, but a peaceful escape from the ordinary. See Listing Details & 59 images. Includes a Virtual Tour

$1,800,000 $317 per sq.ft. Wolfeboro NH Home »

Waterfront on Lake Winnipesaukee
4 Beds | 5 Baths |   Total Sq. Ft. 5672  |  Acres: 1.22
Listed on Friday Mar 27, 2026
Description: Discover an exceptional standard of living in this exquisitely constructed 2007 estate, combining fine craftsmanship and luxury with private Lake Winnipesaukee water access. Spanning two thoughtfully designed levels, this home greets you with gleaming cherry floors and an expansive open living room anchored by a gorgeous wood fireplace with custom built-ins, and a lovely appointed dining room offers intimate dinners and larger gatherings. Every detail has been curated for comfort and beauty, from thermopane windows with custom window treatments and ceiling fans, to central air conditioning and ambient lighting on dimmers and a whole house generator. Enjoy the chef's kitchen, featuring warm cherry cabinetry, a professional gas cooktop and double ovens, and a butcher block island. Retreat to the main-floor primary suite, or utilize the second primary suite upstairs for guests with additional bedrooms. Enjoy the finished lower level with more entertaining space and radiant heat, and additional rooms including an office and craft room. Outdoor living is unrivaled: relax on the tiled floor heated three-season porch with ceiling fans, the sprawling back deck, or follow the path to your deeded private beach shared by 9 properties on Lake Winnipesaukee. With access to a boat slip or mooring for a 22-foot boat, your lake life adventures begin right at your doorstep. Come view this beautiful Wolfeboro home and begin making your own lake memories today. See Listing Details & 58 images. Includes a Virtual Tour

New Listing! Wolfeboro NH Home for sale $1,995,000 $428 per sq.ft.

$1,995,000 $428 per sq.ft. Wolfeboro NH Home »

Waterfront on Lake Winnipesaukee
4 Beds | 5 Baths |   Total Sq. Ft. 4657  |  Acres: 3.62
Listed on Saturday Apr 11, 2026
Description: Enjoy four seasons of breathtaking, panoramic views of Lake Winnipesaukee and the Belknap Mountains from this beautiful, custom-built home on 3.62 acres about a mile north of downtown Wolfeboro "The Oldest Summer Resort in America" which offers wonderful shopping and excellent restaurants. Quality and attention to detail are obvious throughout this lovely home with hickory floors, crown molding, wainscoting, pocket doors, double sided fireplaces and an elevator to all three floors. A spacious kitchen with gorgeous views, a walk though pantry, a huge south facing deck, an impressive first floor Primary Suite, plenty of closets and large storage areas throughout make it easy living for a couple or family gatherings. See Listing Details & 36 images.

$2,200,000 $456 per sq.ft. Wolfeboro NH Home »

4 Beds | 5 Baths |   Total Sq. Ft. 4824  |  Acres: 1.07
Listed on Wednesday Mar 18, 2026
Description: Welcome to 28 Lady Slipper Lane, a stunning new construction home thoughtfully designed for comfort, style, and effortless first-floor living. Set in a peaceful setting just minutes to downtown Wolfeboro, this beautifully crafted property blends modern luxury with timeless design. Step inside to discover custom tile flooring and a breathtaking great room with soaring ceilings, a striking stone fireplace, and expansive windows that fill the home with natural light. The custom kitchen is built for gathering and entertaining, featuring luxury appliances, an oversized island, and exceptional craftsmanship throughout. The main-level primary suite offers a private retreat with radiant heated floors in the bath, creating a spa-like experience year-round. In total, the home offers four spacious bedrooms and 4.5 bathrooms, providing plenty of room for family and guests. Outdoor living is just as inviting with a wrap-around porch perfect for relaxing mornings or evening gatherings. The oversized garage provides ample space for vehicles, an EV charger built in, space for recreational equipment, and storage. The finished lower level expands the living space with a large family area, a massive custom bar ideal for entertaining, and a convenient ¾ bathroom, creating the perfect space for game nights, celebrations, or casual gatherings. With central air conditioning, forced hot air heat, and high-end finishes throughout, this exceptional home offers comfort, quality, and room to enjoy every season. See Listing Details & 40 images.

$2,995,000 $420 per sq.ft. Wolfeboro NH Home »

7 Beds | 5 Baths |   Total Sq. Ft. 7138  |  Acres: 2.7
Listed on Friday Nov 7, 2025
Description: Built in 1895, this magnificent Victorian residence stands as one of Wolfeboro's finest off-lake estates--where historic craftsmanship meets contemporary luxury living. Set on 2.7 acres along the town's idyllic North Main Street, the home offers rare privacy within walking distance to the village and Lake Winnipesaukee. Inside, original woodwork, oversized windows and five fireplaces evoke a grander era, while thoughtful renovations introduce contemporary comfort. The designer kitchen features Miele, Bosch and Wolf appliances along with custom cabinetry and a butler's pantry with a copper sink. 7 bedrooms and 5 baths provide ample space for family and guests. Gathering rooms, a movie room and a workshop add versatility, while a ground-level studio opens to a 35×25 patio -- perfect for a painter, potter, or summer entertainer. The original 2,500 sq. ft. carriage house includes a four-car garage ideal for collectors. Outdoors, an 18×40 heated pool with swim jet and pergola anchors lush, landscaped grounds. With town approval, the property would also be suitable for a luxury inn, wedding venue or condominiums. Property is on public water and sewer. Meticulously maintained and lovingly restored, this home represents Wolfeboro's architectural heritage at its most graceful -- a timeless in-town estate that balances history, artistry, and modern ease. See Listing Details & 60 images. Includes a Virtual Tour

$389,000 $254 per sq.ft. Woodbury VT Home »


Price Change! Reduced by $10,000 down 3% on March 19th 2026
4 Beds | 2 Baths |   Total Sq. Ft. 1530  |  Acres: 11.74
Listed on Monday Jan 12, 2026
Description: Country contemporary home features 4 beds,1-1/2 baths. A main level bedroom,half bath and laundry area walks up to livingroom,dining area and kitchen. Three beds and full bath on second level. Attached one car garage. Attached shed for wood storage. The barn houses small animals, once home to goats and chickens. Located on surveyed 11.7 acres with a path into the woods for walks anytime of the year. Town maintained road drops onto paved Route 14 for an easy commute to the Hardwick,Stowe,and Morrisville areas as well as Montpelier and Barre hubs. All kinds of recreation abound in this location.The home been under good stewardship with added solar roof array,insulation upgrades and heat pump additions. See additional details and Seller improvements attached to listing for full disclosures. The home is ready for the next owner to take to the next level or just come enjoy the country life. See Listing Details & 48 images.

$395,000 $244 per sq.ft. Woodstock VT Home »


Price Change! Reduced by $44,000 down 11% on March 1st 2026
4 Beds | 2 Baths |   Total Sq. Ft. 1617  |  Acres: 0.65
Listed on Wednesday Oct 1, 2025
Description: Classic Vermont farmhouse just minutes from the heart of Woodstock. This charming 4 bedroom , 2 bath home offers the character of a traditional New England property with comfortable , move in ready living spaces. The home features a bright eat-in kitchen, spacious dining room, and a welcoming living room with a wood-burning fireplace--perfect for cozy Vermont evenings. Freshly painted interiors and updated flooring provide a clean , inviting feel while preserving the home's classic farmhouse charm. An attached barn/ garage offers excellent storage and flexible space for outdoor gear , a workshop, or hobby area--ideal for those who enjoy Vermont's year-round outdoor lifestyle. Located just a short drive to the Village Green in Woodstock, the property also provides convenient access to hiking, biking, and skiing at nearby Killington Resort. Whether you are seeking a full time residence or a Vermont getaway , this property offers an excellent opportunity to enjoy one of Vermont's most desirable areas at an attractive price point. Call today for a private viewing. See Listing Details & 47 images.

$599,900 $391 per sq.ft. Woodstock NH Home »


Price Change! Reduced by $20,000 down 3% on April 2nd 2026
4 Beds | 2 Baths |   Total Sq. Ft. 1536  |  Acres: 1.2
Listed on Thursday Jan 15, 2026
Description: Price Improvement to $599,900 -- Don't Miss This Opportunity in North Woodstock! Welcome to 69 Grandview -- a beautifully renovated mountain retreat set on 1.2 acres in one of North Woodstock's most desirable neighborhoods. With 4 bedrooms, 2 full baths, and over 1,500 square feet, this home offers the perfect balance of comfort, charm, and modern updates. Step inside to find a thoughtfully updated interior with upgraded plumbing, electrical, and finishes throughout -- giving you the feel of a newer home while maintaining its classic character. Natural light fills the living spaces, and the layout offers flexibility for full-time living, a vacation getaway, or a high-demand rental. Outside is where this property really shines. Take in peaceful mountain views from the expansive wrap-around deck -- partially covered so you can grill, relax, or entertain in any weather. The generous lot offers privacy, space to expand, and even potential for a garage or future additions. Located just a short drive to Loon and Cannon Mountain, and close to hiking, biking, and everything the White Mountains have to offer, this home puts four-season recreation right at your doorstep. The Grandview neighborhood also takes care of water, roads, and common areas--making ownership that much easier. Whether you're looking for a primary home, second home, or investment property, this is a smart move at a newly improved price. See Listing Details & 60 images.

$675,000 $212 per sq.ft. Woodstock VT Home »


Price Change! Reduced by $14,000 down 2% on March 26th 2026
4 Beds | 3 Baths |   Total Sq. Ft. 3190  |  Acres: 2.94
Listed on Friday Feb 20, 2026
Description: 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 villages. This expansive home offers generous living space with many rooms, providing flexibility for a large household, home offices, guest quarters, or the potential to create multiple apartments (buyer to verify local regulations).Inside, you'll find two charming fireplaces that add warmth and character, perfect for cozy Vermont evenings. The home's classic architecture blends timeless appeal with endless possibilities for customization. Set on over 2 acres, the property features a fenced yard ideal for pets, gardening, or outdoor entertaining. A one-car garage adds convenience, while the separate potting shed--complete with electricity and a heater--offers wonderful space for gardening enthusiasts, creative projects, or additional storage. Located just minutes from Woodstock Village, you'll enjoy easy access to boutique shopping, dining, and the renowned Woodstock Inn & Resort and its spa amenities. Vermont's natural beauty surrounds you--world-class skiing, hiking, biking, and year-round recreation make this an exceptional place to unwind, recharge, and truly enjoy life. A unique property with space, charm, and opportunity in historic Woodstock. See Listing Details & 45 images.

Under Contract Woodstock VT Home for sale $695,000 $194 per sq.ft.

$695,000 $194 per sq.ft. Woodstock VT Home »


Price Change! Reduced by $30,000 down 4% on March 2nd 2026
4 Beds | 3 Baths |   Total Sq. Ft. 3584  |  Acres: 5.1
Listed on Saturday Oct 25, 2025
Description: 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 it wanders through the property past small meadows tucked in along the banks. The home can be accessed privately at grade level through the heated garage and mudroom, while guests enter via a covered entry to the upper level. The lower walk-out level of the home has two bedrooms, a shared bath, laundry and workshop. The elevated second floor is dedicated to gathering spaces including a great room with cathedral ceilings, eat in kitchen and family room that opens out on to a broad deck with overlooking the brook as it flows to the nearby Woodstock golf course and Athletic Club. The spacious primary bedroom offers an ensuite bathroom and abundant closet space. The main floor guest bedroom with loft is served by an adjacent bathroom. The two-stall multi-purpose barn opens to a small pasture and a fence yard for pets. A home for all seasons and reasons. See Listing Details & 40 images.

Under Contract Woodstock VT Home for sale $725,000 $239 per sq.ft.

$725,000 $239 per sq.ft. Woodstock VT Home »

5 Beds | 3 Baths |   Total Sq. Ft. 3028  |  Acres: 1.18
Listed on Wednesday Jan 21, 2026
Description: 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 kitchen on first level anchored by an expansive deck for entertaining or enjoying the afternoon sun. Handsome hardwood floors throughout, stainless appliances in the kitchen accented with granite countertops. The lower level is walk out and includes a very large family room with a 3/4 bathroom and 4th bedroom. Bonus!- there is a wonderful apt located on the ground level for easy access. This apt features a one bedroom, 1bath with living room , dining and kitchen along with its own washer and dryer. It is completely independent from the main house except for water and sewer. Lower level is a 2 bay garage. This apt has been used for both long term and short term rentals with very good rental history. This property is in wonderful condition and close to all of towns amenities including restaurants, shopping, skiing, championship golf and fly fishing. The back of property is abutted by conservation land, located on a dead end road for lots of privacy. Come take a look! See Listing Details & 45 images.

Under Contract Woodstock VT Home for sale $825,000 $212 per sq.ft.

$825,000 $212 per sq.ft. Woodstock VT Home »

5 Beds | 5 Baths |   Total Sq. Ft. 3886  |  Acres: 2.36
Listed on Saturday Sep 6, 2025
Description: NEW PRICE! This lovely,expanded Cape sits just a half mile from Woodstock Village's East End.Surrounded by rolling green fields and wooded hillsides-this home offers a beautiful country setting less than a mile to village shopping, schools, dining and recreation. Updated with modern finishes to enhance accessibility and one level living-while maintaining the warm, country charm. First floor features a kitchen with granite countertops, island with seating & storage, double pantry and all new appliances; dining room with fireplace, an all season sun room w/gas fireplace and deck access, a wonderful new laundry room with half bath, lovely primary bedroom and bath with soaking tub, tiled zero step shower(roll-in), & double sinks, & living room w/fireplace. Lots of light and warm wood floors throughout. Two bedrooms with sitting areas and lots of storage and full bath upstairs. The connected 2 bedroom apartment lends flexibility-it can be used as additional living space, overflow for guests or for extra income as a rental. Full kitchen,first floor bedroom and bath,second floor bedroom & storage loft and one car garage with second driveway, private entrance, deck and laundry.The back of the property slopes down to a babbling brook and then up to meet direct trail access to Mount Peg.Expansive deck,generator,attached two car garage & partially finished walk out basement with tons of storage, a recreation room or office and powder room too. So many possibilities! Easy to show and move-in ready! See Listing Details & 60 images.

$985,000 $354 per sq.ft. Woodstock VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 2785  |  Acres: 5.01
Listed on Monday Jul 21, 2025
Description: This early Woodstock residence was built in 1792 by Joseph Wood on a parcel of land he purchased in 1786 from Ebenezer Kingsley, one of Woodstock early settlers. A classic New England Cape of the period with the notable features of a central chimney with multiple fireplaces and a second story overhang on the gables. The house retains a great deal of original features and fabric including wide board flooring, horizontal wainscotting, period doors and hardware and a keeping room fireplace. Massive exposed beams substantiate the date of construction. The four bedrooms and three baths include a first floor primary en suite bedroom. Spacious rooms with unusually high ceilings and multi pane windows create a comfortable living space. Beautifully sited and located on the exclusive Randall Road within a grove of ancient sugar maples. See Listing Details & 37 images.

Under Contract Woodstock VT Home for sale $1,195,000 $448 per sq.ft.

$1,195,000 $448 per sq.ft. Woodstock VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 2668  |  Acres: 8.32
Listed on Wednesday Feb 18, 2026
Description: 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 Vermont: privacy, craftsmanship, and striking mountain views that feel close enough to touch. Thoughtfully designed by the respected Vermont Vernacular Builders, the home reflects classic regional architecture with refined proportions, timeless materials, and an effortless sense of place. The interior is bright, welcoming, and designed for both everyday living and memorable gatherings. Wide board floors run throughout, while exposed beams lend texture and authenticity to the inviting den and spacious eat-in kitchen. A butler's pantry provides exceptional storage and service flow to the formal dining room, and multiple living spaces -- including a fireplaced living room with gas insert and a den warmed by a wood stove -- offer comfortable options for relaxing or entertaining in every season. Positioned on more than eight private acres, the setting feels peaceful and secluded, yet remains remarkably convenient: Woodstock's celebrated restaurants, boutiques, and cultural attractions are just minutes away, and premier skiing at Killington's Skyeship Base Lodge is under eight miles from your door. Outdoor living is equally compelling, with a large deck perfectly oriented toward the mountains, an in-ground pool for summer enjoyment, and an oversized garage/barn with storage above presenting exciting potential for a guest suite, studio, or party barn. A rare combination of location, quality, and lifestyle flexibility, this property is ideally suited as a full-time residence, seasonal retreat, or investment in Vermont living at its best. See Listing Details & 57 images.

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