South Londonderry, VT Homes for Sale

/35
$359,000
- 3 Beds
- 2 Baths
- 1,120 Sq Ft
33 Aspen Ln, Bondville, VT 05340

Minutes from Stratton Mountain, this cozy chalet offers the perfect mountain escape with timeless character and room to make it your own. Featuring a classic chalet style floor to ceiling stone fireplace and wood interior, this home exudes vintage alpine charm. There are three bedrooms, two baths and an open concept living space, providing plenty of room for gatherings or weekend getaways.

Alison Cummings

Cummings & Co

(802) 424-9210

33 Aspen Ln, Bondville, VT 05340
/41
$8,950,000
- 6 Beds
- 10 Baths
- 13,393 Sq Ft
370 Fischer Ln, Jamaica, VT 05343

Accessible, but miles from the everyday. Camp Endo’s mountain kingdom is minutes from Stratton Mtn. with a 21st century take on a mountain timberframe home, and 417+/- acres threaded with trails and ridgelines. Ski your own glades and rip the eight miles of custom-designed mountain biking terrain, or just pause to enjoy the vast views. The house reimagines a rustic lodge with classic wood, bark

Dia Jenks LandVest, Inc/Woodstock

370 Fischer Ln, Jamaica, VT 05343
/15
$775,000
- Land
- 52 Acres
- $14,924 per Acre
0 W Hill Rd, Jamaica, VT 05343

The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 5 is 51.93 acres and is located at the top of the subdivision. This parcel is very

Thom Milke Fountains Land Inc.

0 W Hill Rd, Jamaica, VT 05343
/11
$595,000
- Land
- 69 Acres
- $8,637 per Acre
0 W Hill Rd, Jamaica, VT 05343

The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 4 is 68.89 acres and is the largest of the five parcels for sale. This lot has a

Thom Milke Fountains Land Inc.

0 W Hill Rd, Jamaica, VT 05343
/8
$320,000
- Land
- 35 Acres
- $9,267 per Acre
0 W Hill Rd, Jamaica, VT 05343

The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 3 is 34.53 acres, and is mostly forested near the access road. A driveway would need

Thom Milke Fountains Land Inc.

0 W Hill Rd, Jamaica, VT 05343
/7
$235,000
- Land
- 15 Acres
- $15,390 per Acre
0 W Hill Rd, Jamaica, VT 05343

The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 2 is 15.27 acres and is the first parcel found on the left side of the newly built 20 foot

Thom Milke Fountains Land Inc.

0 W Hill Rd, Jamaica, VT 05343
/43
$920,000
- 5 Beds
- 4 Baths
- 2,238 Sq Ft
8 E Birch Rd Unit 103, Stratton, VT 05360

Rare 5BR/4BA Stratton Townhome | Ski-Back Access | Designer Furnished | Spacious, fully renovated 5-bedroom, 4-bath townhome at Stratton with ski-back access. Professionally designed and furnished by ACK Design, this move-in-ready home blends mountain charm with modern finishes. The main level features hardwood floors, a stunning floor-to-ceiling stone fireplace, and a granite kitchen

Cheyanne Pugliese

8 E Birch Rd Unit 103, Stratton, VT 05360
/37
$999,000
- 4 Beds
- 3.5 Baths
- 2,280 Sq Ft
17 Roundtree Rd, Winhall, VT 05340

Contemporary ski chalet on shuttle route located on a short cul-de-sac in the coveted North Brookwood neighborhood, a stone's throw from the Stratton base lodge. This 4 bedroom, 3 1⁄2 bath home boasts an open plan, walls of windows, and floor-to-ceiling stone fireplace in the Great Room. The pass-through kitchen was fully renovated in 2021 in addition to many other upgrades. Test your skills at

Sarah Nichols Winhall Real Estate

17 Roundtree Rd, Winhall, VT 05340
/59
$1,000,000
- 3 Beds
- 2 Baths
- 2,700 Sq Ft
580 Cross Rd, South Londonderry, VT 05155

Tucked away in a tranquil setting, this newly constructed 3-bedroom, 2-bath barn-style residence is a masterful fusion of heritage & refined elegance, situated on 5.4 pristine acres. Absorb the beauty of reclaimed exposed overhead beams, while expansive floor-to ceiling custom-crafted windows capture mountain vistas & bathe interiors in golden natural light. Large sliding doors open to the melody

Loana Sargent Wohler Realty Group

580 Cross Rd, South Londonderry, VT 05155
/33
$995,000
- 3 Beds
- 2 Baths
- 1,620 Sq Ft
19 Village Lodge Rd Unit 407, Stratton, VT 05155

Rare opportunity to own in the heart of the Stratton Mountain Village! Come home to the Landmark community. Located attached to the iconic "Clocktower" at Stratton, Vermont. This homes boasts three spacious bedrooms and two full bathrooms with amazing mountain views and southern exposure. Enjoy the cozy gas burning fireplace after a hard day skiing or riding. Landmark provides ski lockers, an

Timothy Mich Doddridge Stratton Real Estate

19 Village Lodge Rd Unit 407, Stratton, VT 05155
/38
$1,499,999
- 3 Beds
- 3.5 Baths
- 3,300 Sq Ft
111 Hughes Ln, Jamaica, VT 05343

Fully renovated in 2022, 450 ft of lake front footage on picturesque Cole Pond. Nestled on nearly 2 acres in Jamaica, VT, this stunning singlefamily home at 111 Hughes Lane was built in 1989 and offers a peaceful retreat for its next owners. With 3 bedrooms, 3 bathrooms, and 1 half bathroom, and 4 built-in adult size bunks for comfortable sleeping of 10, Air-conditioned master bedroom and

Derek Greene Derek Greene

111 Hughes Ln, Jamaica, VT 05343
/37
$2,400,000
- 5 Beds
- 4.5 Baths
- 3,252 Sq Ft
115 Benson Fuller Dr, Jamaica, VT 05343

Perched on 3.5 private acres with commanding views from Stratton’s iconic slopes to Bromley’s trails, this architecturally striking residence blends the serenity of the mountains with sophisticated modern design. A dramatic central staircase anchors the home, leading to a sleek custom kitchen and a vaulted great room where walls of glass frame panoramic vistas. A floor-to-ceiling stone fireplace

Carrie Mathews Winhall Real Estate

115 Benson Fuller Dr, Jamaica, VT 05343
/60
$1,825,000
- 3 Beds
- 4 Baths
- 2,872 Sq Ft
36 Beaver St, Bondville, VT 05340

Your Ultimate Vermont Mountain Retreat Awaits! Just 4 miles from Stratton & minutes to Bromley, this inviting log home is the perfect year-round escape—crafted for adventure, relaxation, and making lasting memories in every season. Whether you’re hitting the slopes in winter, hiking through summer trails, or soaking in the stunning fall foliage, this property delivers! Plus, it's only a 10-minute

MaryKate Grey Stratton Real Estate

36 Beaver St, Bondville, VT 05340
/16
$635,000
- 2 Beds
- 2 Baths
- 916 Sq Ft
761 Stratton Mountain Access Rd Unit 240, Stratton, VT 05360

Beautifully renovated two bedroom two bathroom condominium in the ever popular Long Trail House community at Stratton Mountain Resort. Recently updates include new flooring throughout, paint, granite counter tops in kitchen and bathrooms, stainless steel appliances, window treatments, furniture and decor. Not many details have been left out. This particular floorplan boasts a large primary

Timothy Mich Doddridge Stratton Real Estate

761 Stratton Mountain Access Rd Unit 240, Stratton, VT 05360
/50
$1,050,000
- 5 Beds
- 5.5 Baths
- 4,729 Sq Ft
83 Benson Fuller Dr, Bondville, VT 05340

Just an 8-minute drive to Stratton, 83 Benson Fuller Drive sits atop the beautiful Forest Farms neighborhood, offering both serenity and convenience. This meticulously updated home is ready for you to move in and enjoy the best of Vermont living. Nestled on a quiet dirt road, it’s perfect for morning and evening strolls with the dog before or after a day on the slopes.Inside, this

Christiane Carroccio TPW Real Estate

83 Benson Fuller Dr, Bondville, VT 05340
/15
$485,000
- 2 Beds
- 2 Baths
- 1,353 Sq Ft
49 High Point Dr Unit A-14, Stratton, VT 05360

49 High Point Drive, Crown Point A14, Stratton, VTIncredible opportunity to make Stratton Mountain Resort a place to call home. Nestled in the Green Mountains of Vermont, Crown Point offers easy condominium living close to the Stratton Mountain Resort Village. Shuttle service to the base area for skiing and riding. An outdoor pool and BBQ area is inviting for summer use. This one-level 2

Andrew King Stratton Real Estate

49 High Point Dr Unit A-14, Stratton, VT 05360
/20
$495,000 Open Sun 11AM - 1PM
- 4 Beds
- 3 Baths
- 1,920 Sq Ft
374 Winhall Hollow Rd, Winhall, VT 05340

Tucked away on 9.5 private acres that border the scenic Gale Meadows Pond, this Vermont retreat offers the perfect mix of nature, comfort, and functionality. Whether you're seeking a year-round residence or a seasonal getaway, this property is move-in ready with thoughtful renovations and room to explore. Step inside to a warm and inviting atmosphere where you’ll find brand-new kitchen

Annette Gallo Real Broker LLC

374 Winhall Hollow Rd, Winhall, VT 05340
/27
$440,000
- 3 Beds
- 2 Baths
- 1,400 Sq Ft
6 Moose Maple Rd, Winhall, VT 05340

Located in the desirable Moose Maple section of Birch Hill, this well-maintained 3-bedroom, 2-bath Co-Op offers some of the best direct views of Stratton Mountain, along with the convenience of a community shuttle and close proximity to the newly rebuilt seasonal pool. Freshly painted and thoughtfully updated, the condo features flexible living spaces including a lower-level bedroom with a custom

Andy Reed Four Seasons Sotheby's Int'l Realty

6 Moose Maple Rd, Winhall, VT 05340
/6
$84,900
- Land
- 1.78 Acres
- $47,697 per Acre
0000 Wonder Ln, Jamaica, VT 05343

Prime 1.78-Acre Wooded Lot near Stratton Mountain Ski Resort and Golf Course---Nestled down a serene and private dirt road, this magnificent 1.78-acre wooded lot offers an unparalleled opportunity to build your dream home amidst Vermont's natural beauty. Located conveniently close to the renowned Stratton Mountain Ski Resort and Golf Course, this property promises year-round recreation and

Rachel Febbie EXP Realty

0000 Wonder Ln, Jamaica, VT 05343
/7
$74,900
- Land
- 2.06 Acres
- $36,359 per Acre
000 Wonder Ln, Jamaica, VT 05343

Prime 2.06-Acre Wooded Lot near Stratton Mountain Ski Resort and Golf Course---Nestled down a serene and private dirt road, this magnificent 2.08-acre wooded lot offers an unparalleled opportunity to build your dream home amidst Vermont's natural beauty. Located conveniently close to the renowned Stratton Mountain Ski Resort and Golf Course, this property promises year-round recreation and

Rachel Febbie EXP Realty

000 Wonder Ln, Jamaica, VT 05343
/60
$710,000
- 3 Beds
- 2.5 Baths
- 2,034 Sq Ft
3 Short Rd, Bondville, VT 05340

Reside in a renovated 1800s expanded cape in Vermont, complete with all the country amenities you desire! The presence of a barn with a workshop indicates that the home you are purchasing is well cared for. The eat-in kitchen boasts a soapstone sink, pine flooring, granite countertops, and custom cabinetry. The living room features a wood-burning fireplace, as does the dining room. An addition

Mike England Michael England Real Estate

3 Short Rd, Bondville, VT 05340
/36
$720,000
- 4 Beds
- 4 Baths
- 2,389 Sq Ft
58 Todd Hill Rd, Bondville, VT 05340

Escape to your mountain retreat in this spacious 4 bedroom, 4 bath home tucked away in a serene wooden community just minutes away from Stratton Mountain Resort. Perfect for entertaining or relaxing, the home features two cozy wood burning fireplaces that brings warmth and charm throughout the season. Vaulted ceilings in the living room and dining room area provide lots of natural light. Step

Jamie Wylie Stratton Real Estate

58 Todd Hill Rd, Bondville, VT 05340
/39
$699,000
- 6 Beds
- 3 Baths
- 2,825 Sq Ft
95 Melendy Hill Rd, Londonderry, VT 05155

A fully reimagined 1900’s farmhouse located in the heart of South Londonderry. This six-bedroom, three-bath home has been meticulously remodeled to blend timeless character with contemporary style. Sunlight pours through all-new windows, illuminating generous living spaces. Every detail has been thoughtfully upgraded, from the new heating system, engineered and installed septic, well, and

Jessica Citera Cummings & Co

95 Melendy Hill Rd, Londonderry, VT 05155
/20
$590,000
- 2 Beds
- 2 Baths
- 920 Sq Ft
771 Stratton Mountain Access Rd Unit 361, Stratton, VT 05360

Experience the best of mountain living at Long Trail House. This light-filled 2-bedroom, 2-bath condo offers comfort, convenience, and an unbeatable location just steps from Stratton’s lifts, shops, and restaurants. The open-concept living area features a gas fireplace, perfect for cozy apres-ski gatherings, and a well-equipped kitchen with a breakfast bar for casual dining. This corner unit has

Christiane Carroccio TPW Real Estate

771 Stratton Mountain Access Rd Unit 361, Stratton, VT 05360
/43
$899,000
- 4 Beds
- 3 Baths
- 3,155 Sq Ft
460 Stratton Gate Rd, Jamaica, VT 05343

This exceptional property blends classic post-and-beam farmhouse design with modern craftsmanship. The stunning barn addition is an architectural masterpiece, admired from every angle and flooded with natural light through expansive windows that frame the serene surroundings. Soaring ceilings, rich hardwood floors, and custom finishes create an atmosphere of timeless elegance. An expansive loft

Helen Nault

460 Stratton Gate Rd, Jamaica, VT 05343
/34
$275,000
- 3 Beds
- 2 Baths
- 2,613 Sq Ft
533 Pratt Bridge Rd, Jamaica, VT 05343

Nestled in the peaceful and desirable Cole Pond neighborhood, while being merely minutes away from: Stratton Mountain Resort, renowned for its skiing and year-round recreational activities The picturesque landscapes of Southern Vermont – offering hiking, fishing, and various outdoor pursuits Seclusion and serenity on your own 1.6-acre sanctuary. This contemporary 3 bedroom with loft 2 bath,

Mike England Michael England Real Estate

533 Pratt Bridge Rd, Jamaica, VT 05343
/17
$399,000
- 1 Bed
- 1 Bath
- 820 Sq Ft
10 Ober Tal Dr Unit B12, Stratton, VT 05360

Own at Ober Tal and enjoy Slopeside Living in the heart of Stratton Mountain. Just steps from the Trails and Tamarack Chair Lift, getting on the slopes couldn’t be easier. This updated one-bedroom, one-bath home features an airy open living and dining area with a classic wood-burning fireplace as its centerpiece. A ground-level location offers the bonus of a private patio, while the generous

Helen Nault

10 Ober Tal Dr Unit B12, Stratton, VT 05360
/56
$3,750,000
- 7 Beds
- 7.5 Baths
- 6,900 Sq Ft
192 N Brookwood Rd, Stratton, VT 05360

Perched at the top of Stratton Mountain Resort's most desired destination, this exceptional 7 Bedroom/7.5 Bath retreat is a prime alpine experience. Near the Wanderer ski trail w/ breathtaking views stretching across the Green Mountains, every detail of this property has been designed to offer privacy-capturing the essence of four-season luxury.With a rare blend of refined elegance & natural

Kim Morgan-Wohler Wohler Realty Group

192 N Brookwood Rd, Stratton, VT 05360
/59
$1,300,000
- 4 Beds
- 2 Baths
- 1,900 Sq Ft
51 Village Square, Stratton, VT 05360

Experience this Extraordinary Location in the heart of the Stratton Resort Village from this RENOVATED and EXPANDED Village Square 4 bedroom unit where you can walk to everything and be on the lifts in just a few minutes. Nothing compares to trailside living in the VILLAGE where convenience abounds and you won't touch your car until it's time to hit the highway. Ski home for lunch and you'll have

Kim Morgan-Wohler Wohler Realty Group

51 Village Square, Stratton, VT 05360
/38
$789,000
- 4 Beds
- 4 Baths
- 2,997 Sq Ft
44 Hilltop Rd, Winhall, VT 05340

Four bedroom, four bathroom Intervale townhouse has all the space you need in a Stratton home. This is the largest Intervale floor plan, with a second living room and wet bar on the lower, walk out floor. The main floor has a mud room entry, living room with wood burning fireplace, and dining room open to kitchen. The primary suite is on the main floor, secondary suite is upstairs, and an

Christiane Carroccio TPW Real Estate

44 Hilltop Rd, Winhall, VT 05340
/44
$495,000
- 3 Beds
- 3 Baths
- 1,600 Sq Ft
486 Windy Rise Ln E, Londonderry, VT 05148

Contemporary Ski-Style Retreat in Southern Vermont – A Home for All Seasons!Escape to the mountains in this 3-bedroom, 3-bath home, nestled in the heart of Southern Vermont—just minutes from Stratton, Bromley, and Magic Mountain ski resorts.This home has rustic charm, features multiple living spaces and a bathroom on each floor. The relaxed dining/living space is open and inviting so

Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

486 Windy Rise Ln E, Londonderry, VT 05148
/26
$529,000
- 4 Beds
- 2.5 Baths
- 1,864 Sq Ft
1966 Thompsonburg Rd, South Londonderry, VT 05155

A quiet, private sanctuary in a prime location—just minutes from all three local ski areas, Lowell Lake, and the shopping and dining of Londonderry and Manchester. This 4-bedroom retreat is ready to be loved by a new family. Enjoy newly updated bathrooms, appliances, countertops, a new chimney liner, a wood-burning fireplace, and a wood stove insert that makes the family room especially cozy on

Wilkie Bushby TPW Real Estate

1966 Thompsonburg Rd, South Londonderry, VT 05155
/59
$2,800,000
- 3 Beds
- 3.5 Baths
- 3,938 Sq Ft
23 Valley View Rd, Winhall, VT 05340

Set at the end of a long, private driveway, this remarkable property unveils dramatic panoramic vistas that stretch nearly 40 miles. Offering a rare sense of seclusion & grandeur, the home is an ideal retreat where nature, privacy, and beauty converge.Designed w/a modern aesthetic,an expansive open-concept layout, the main floor features a stunning stone fireplace , enhanced by soaring ceilings

Kim Morgan-Wohler Wohler Realty Group

23 Valley View Rd, Winhall, VT 05340
/37
$730,000
- 5 Beds
- 3 Baths
- 2,635 Sq Ft
341 Under the Mountain Rd, Londonderry, VT 05148

Escape to this idyllic 1800s cape-style farmhouse nestled on a quiet dirt road in a peaceful country setting, just minutes from three popular ski areas. Set on 44 private acres with a scenic pond, this unique property offers the perfect blend of historic character and modern comfort, making it ideal for a family getaway, vacation rental, or year-round home. Inside, you'll find surprisingly

Andy Reed Four Seasons Sotheby's Int'l Realty

341 Under the Mountain Rd, Londonderry, VT 05148
/44
$729,000
- 4 Beds
- 2 Baths
- 2,040 Sq Ft
86 Benson Fuller Dr, Bondville, VT 05340

OPEN HOUSE Saturday August 30 11-1. Great opportunity! Your Ultimate Getaway Escape to this idyllic Vermont retreat, where convenience meets relaxation. This spacious home offers everything you need for a fun-filled and carefree lifestyle, from outdoor entertaining to cozy indoor spaces.Step out onto the large deck and unwind by the gas fire pit table, or enjoy watching the friendly mini-golf

Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

86 Benson Fuller Dr, Bondville, VT 05340
/28
$1,700,000
- 4 Beds
- 3.5 Baths
- 2,363 Sq Ft
43 Middle Ridge Rd Unit 415, Winhall, VT 05155

Perfect for the large family! Four bedrooms, Three and a Half Baths, plus a Loft! In highly desirable Rising Bear Lodge, Top Floor, Corner location! Easy walking distance to the Slopes, (Shuttle also available), the Commons' Skating Pond, and the Village Shops and Restaurants. Other amenities include a year round heated Pool, outdoor hot tubs, and a cedar sauna---all comfortably accessible by the

Edwin Kevil Stratton Real Estate

43 Middle Ridge Rd Unit 415, Winhall, VT 05155
/55
$2,225,000
- 4 Beds
- 4.5 Baths
- 5,000 Sq Ft
16 Hunter Ridge Rd, Bondville, VT 05340

Custom built Wadsworth Design Build timber-frame mountain retreat blends luxury, craftsmanship, and convenience just minutes from Stratton Mountain Resort. Set on 2.66 acres and spanning 5,000± square feet, this 4-bedroom, 5-bath home includes two additional sleeping space ideal for hosting friends and family. A grand entry framed by oversized Douglas fir posts welcomes you into a lodge style

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

16 Hunter Ridge Rd, Bondville, VT 05340
/35
$799,000
- 3 Beds
- 2.5 Baths
- 2,230 Sq Ft
5 Linscott Rd Unit 56, Jamaica, VT 05343

This irresistible renovated Forest Farms contemporary with 3 bedrooms and 2 and a half baths has an inviting ambiance as well as appealing floor plan flow. Past the foyer with half bath is the open living concept with white oak hardwood floors. The glow and warmth of the raised hearth stone fireplace in the living area is shared from windowed dining area to bright kitchen with all new appliances,

Diana Stugger Four Seasons Sotheby's Int'l Realty

5 Linscott Rd Unit 56, Jamaica, VT 05343
/36
$1,790,000
- 4 Beds
- 3 Baths
- 2,545 Sq Ft
1949 South Rd, Peru, VT 05152

Nestled in a serene and picturesque setting, Berry Hill Farm offers a rare opportunity to own an exceptional Vermont estate blending charm, versatility, and natural beauty. Spanning 15.52 acres across two separately deeded lots, the property combines inspired design with modern comfort. At its heart is a beautifully crafted contemporary home featuring three spacious bedrooms, sunlit living

Kim Morgan-Wohler Wohler Realty Group

1949 South Rd, Peru, VT 05152
/41
$574,000
- 3 Beds
- 3 Baths
- 2,704 Sq Ft
4138 W Hill Rd S, Jamaica, VT 05343

This three-bedroom, three-bath custom-built log home is situated on 2.37 acres in a tranquil mountain setting just minutes from skiing. Built with double tongue-and-groove log construction, the cozy home provides the warm wood interior one would expect. The open-concept main level focuses on the fieldstone hearth, wood stove, and beautiful oak floors. A covered porch in the front of the home

Patricia Fitzpatrick Skihome Realty

4138 W Hill Rd S, Jamaica, VT 05343

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Vermont Windham County South Londonderry

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The most popular zip codes in South Londonderry, VT include 05155, 05340, 05341, 05343 and 05148.

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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.