South Londonderry, VT Homes

/34
$359,000 Under Contract
- 2 Beds
- 2 Baths
- 1,296 Sq Ft
6217 Vt Route 30, Jamaica, VT 05343

Perched on a hill above the village of Jamaica, this inviting Cape-style home offers privacy and stunning surroundings just minutes from Stratton Mountain. Sitting on 1.5 acres, the property provides a peaceful retreat with easy access to Winhall, Stratton, and endless outdoor activities. A babbling stream flows nearby, adding to the tranquil setting as you relax on the spacious

Trent Stephens

Wohler Realty Group

(802) 424-9864

6217 Vt Route 30, Jamaica, VT 05343
/48
$7,000 per month
- 5 Beds
- 3.5 Baths
- 3,858 Sq Ft
- House for Rent
20 Jamie Ln, Winhall, VT 05340

Escape to the tranquility of Vermont with this stunning long-term rental at "Valley View." Nestled in a desirable neighborhood of Winhall, this spacious contemporary home offers unparalleled panoramic views of the surrounding mountains. Imagine waking up to the beauty of the Green Mountains every day in this expansive retreat!This meticulously maintained 5-bedroom, 3.5 bathroom home boasts a

David Powers 42 North LP

20 Jamie Ln, Winhall, VT 05340
/25
$499,000 Sold May 02, 2025
- 1,096 Sq Ft
- $455/SF
- 2 Days On Market
- 2 Beds
- 2 Baths
- Built 1983
16 Ober Tal Dr Unit E35, Stratton, VT 05360

This top-floor, 2-bedroom, 2-bath condo in the sought-after E section of Ober Tal offers the ultimate in mountain access. Located just steps from the lifts, it's a true ski-in/ski-out property, and in the warmer months, enjoy hiking and mountain biking directly from your door. Whether you're hitting the slopes, exploring the trails, or biking the mountain, this condo offers the perfect location

Carrie Mathews Winhall Real Estate

16 Ober Tal Dr Unit E35, Stratton, VT 05360

/20
Est $743,041 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,036 Sq Ft
78 Middle Ridge Rd Unit 102, Stratton, VT 05155

78 Middle Ridge Rd Unit 102, Stratton, VT 05155

/15
$850,000
- Land
- 52 Acres
- $16,368 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 unique,

Thom Milke Fountains Land Inc.

0 W Hill Rd, Jamaica, VT 05343
/46
$5,000 per month
- 3 Beds
- 3.5 Baths
- 2,300 Sq Ft
- House for Rent
15 Nearing Rd, Winhall, VT 05340

Imagine waking up to inspiring vistas every day in this remarkable 3 bedroom, 3.5 bath saltbox home. Perched to capture stunning panoramic views of Stratton Mountain's trails, this classic contemporary ski home offers a truly special living experience. The property is settled upon a 1.63-acre knoll and abuts the Winhall Forest, offering peace and privacy.Embrace sustainable living with a large,

David Powers 42 North LP

15 Nearing Rd, Winhall, VT 05340
/35
$227,000 Sold May 02, 2025
- 2,072 Sq Ft
- $110/SF
- 146 Days On Market
- 3 Beds
- 2 Baths
- Built 1830
347 Main St, South Londonderry, VT 05155

Nestled in a peaceful location just 10 minutes from Bromley, Stratton, and Magic Mountains, this 3-bedroom, 2-bathroom home offers the perfect mix of comfort, charm, and functionality. With stunning views in every direction, it’s an ideal spot for both relaxation and entertaining. The spacious living room, featuring a beautiful fireplace, serves as the heart of the home. Large windows frame

Bob Maisey Berkshire Hathaway HomeServices Stratton Home

347 Main St, South Londonderry, VT 05155

/30
Not Listed For Sale
- 5 Beds
- 4 Baths
- 2,088 Sq Ft
30 Styles Branch Rd Unit 309, Stratton, VT 05360

30 Styles Branch Rd Unit 309, Stratton, VT 05360

/11
$665,000
- Land
- 69 Acres
- $9,653 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 solid

Thom Milke Fountains Land Inc.

0 W Hill Rd, Jamaica, VT 05343
/19
$3,000 per month
- 3 Beds
- 3 Baths
- 1,900 Sq Ft
- Condo for Rent
47 Crown Point Dr Unit B-13, Stratton, VT 05155

Need a place to get away this Summer or Fall? Look no further. This well-equipped condo has three bedrooms and three full baths. The main living area is the much-desired open concept style which is wonderful for entertaining. There is a second living room on the lower level which is fantastic for company. This condo has several mini splits which will conquer those humid nights that we get

Peggy O'neill Cummings & Co

47 Crown Point Dr Unit B-13, Stratton, VT 05155
/53
$825,000 Sold Apr 29, 2025
- Land
- 36 Acres
- $23,109 per Acre
- 102 Days On Market
324 Pikes Falls Rd, South Londonderry, VT 05155

Extraordinary Stratton Mountain Acreage Opportunity:Discover a rare gem in Stratton Mountain, a 35.7-acre parcel offering breathtaking, commanding views of the resort. Just 5 minutes away from the the Main Base Lodge and less to Sun Bowl. This exceptional property features two building sites, each supported by wastewater systems for a 6-bedroom and a 4-bedroom home.The established driveway leads

Britt Wohler Wohler Realty Group

324 Pikes Falls Rd, South Londonderry, VT 05155

/31
Not Listed For Sale
- 5 Beds
- 2 Baths
- 1,888 Sq Ft
12 Stratton Rd W Unit 12, Winhall, VT 05340

12 Stratton Rd W Unit 12, Winhall, VT 05340

/8
$355,000
- Land
- 35 Acres
- $10,281 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 to be

Thom Milke Fountains Land Inc.

0 W Hill Rd, Jamaica, VT 05343
/18
$3,000 per month
- 4 Beds
- 3 Baths
- 2,202 Sq Ft
- House for Rent
484 Deerwood Hill, Londonderry, VT 05155

Spacious contemporary vacation home in a private setting on nearly 4 acres, with updated kitchen and baths, sunroom and deck with hot tub. Available monthly May 1- Nov 1, 2025. Utilities included, high speed internet. Experience a true Southern Vermont retreat this summer at Deerwood Hill, the perfect location for relaxing and exploring the Stratton area in the warmer months.

Beth Vickers Vermont Real Estate Company

484 Deerwood Hill, Londonderry, VT 05155
/31
$710,000 Sold Apr 28, 2025
- 2,470 Sq Ft
- $287/SF
- 45 Days On Market
- 3 Beds
- 3 Baths
- Built 1995
50 Hilltop Rd, Winhall, VT 05340

Nestled on Hilltop Road in Intervale is this stylish retreat that begs to host your friends and family, with a renovated kitchen that invites chefs and dining counter guests. The new, oversized deck is perfect for spring, summer and fall foliage entertaining. Sunlight fills the living/dining area, and hardwood floors abound on the 1st and 2nd floors of this 3-story home. The bottom floor includes

Jamie Luke TPW Real Estate

50 Hilltop Rd, Winhall, VT 05340

/19
Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,130 Sq Ft
43 High Point Dr Unit D23, Stratton, VT 05360

43 High Point Dr Unit D23, Stratton, VT 05360

/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
/33
$45,000 per month
- 4 Beds
- 2.5 Baths
- 2,600 Sq Ft
- House for Rent
14 Burnt Hill Rd, Winhall, VT 05340

This modern Strattonwald gem is the ultimate plug-and-play Vermont ski house with location, style, convenience and a snow globe lifestyle to remember. Three living spaces -- one on each floor -- allow for plenty of overflow in the morning and apres-ski, with two fireplaces ready for friends, family, and mugs of cocoa. Four bedrooms plus sleep loft with its own hang-out space lend space for the

Jamie Luke TPW Real Estate

14 Burnt Hill Rd, Winhall, VT 05340
/37
$454,000 Sold Apr 28, 2025
- 1,760 Sq Ft
- $258/SF
- 315 Days On Market
- 3 Beds
- 2 Baths
- Built 1987
400 Edie Ln, Jamaica, VT 05343

Welcome to Hot Toddy Hill. your perfect Vermont Getaway! Nestled minutes away from Stratton, this cozy contemporary home in the charming town of Jamaica, Vermont, is ideal for gatherings and retreats with friends. The living room boasts vaulted ceilings with wood slat detail, its ideal for relaxing in front of the wood-burning fireplace apres ski. The fully equipped eat-in kitchen boasts brand

Andie Fusco Four Seasons Sotheby's Int'l Realty

400 Edie Ln, Jamaica, VT 05343

/38
Est $738,763 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,081 Sq Ft
80 Pond View Rd, Winhall, VT 05340

80 Pond View Rd, Winhall, VT 05340

/60
$1,100,000
- 6 Beds
- 5 Baths
- 5,298 Sq Ft
50 Stratton View Rd, Winhall, VT 05340

Custom built six-bedroom home on 2 acres with spectacular views of Stratton Mountain. The kitchen has granite countertops and custom cabinets with the dining area nearby with plenty of space to accommodate a large gathering. The living area has a cathedral ceiling with large windows for an abundance of natural light and stunning year-round views of Stratton Mountain, with a lovely stone fireplace

Mike England Michael England Real Estate

50 Stratton View Rd, Winhall, VT 05340
/16
$30,000 per month
- 3 Beds
- 2 Baths
- 1,570 Sq Ft
- Condo for Rent
5 Byington Ln, Winhall, VT 05340

Get ahead of next ski season and book this impeccably renovated, well-priced rental townhome in Winhall Acres. A classic Austrian chalet, this skiers' home is structured for living and entertaining on the main floor, with downstairs sleeping and ski storage. The functional open kitchen/dining room is perfect for group pre-ski breakfasts and apres-ski fun, with a spacious great room for hanging

Jamie Luke TPW Real Estate

5 Byington Ln, Winhall, VT 05340
/44
$640,000 Sold Apr 25, 2025
- 3,988 Sq Ft
- $160/SF
- 52 Days On Market
- 7 Beds
- 4 Baths
- Built 1942
13 Winhall Station Rd, Londonderry, VT 05155

Solid six-bedroom home with detached one bedroom apartment being offered fully furnished on 3.4 acres of land! Surrounded by mature maples and beautiful local views of Stratton Mountain. This property sits on the corner of Winhall Station Road and Route 100 in Londonderry Vermont. Winhall Station Road will lead out a dead-end road to the Winhall Campground and the West River area with wonderful

Julie Lowe Lowe's Real Estate, LLC

13 Winhall Station Rd, Londonderry, VT 05155

/40
Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 1,215 Sq Ft
3 Red Hickory Unit 3, Winhall, VT 05340

3 Red Hickory Unit 3, Winhall, VT 05340

/12
$1,100,000
- 3 Beds
- 3 Baths
- 1,501 Sq Ft
759 Stratton Mountain Access Rd Unit 339, Stratton, VT 05340

Designed with the mountain enthusiast in mind, and located just a short walk from the Stratton Resort Village and ski slopes, this three bedroom three bath condominium offers quality and convenience. Private parking, pool, hot tub, sauna and shuttle to the slopes.

John Sikes Stratton Real Estate

759 Stratton Mountain Access Rd Unit 339, Stratton, VT 05340
/11
$13,000 per month
- 1 Bed
- 1 Bath
- 1,200 Sq Ft
- House for Rent
23 Old School Rd Unit the Barn, Londonderry, VT 05155

Adorable, Brand New/completely re done in 2023... new everything! Floors, ceilings, windows, furnishing, appliances, beds, TV's..paint. you name it-- NEW and perfect and gorgeously done. Tucked away in quaint idylic S. Londonderry Vt., with a stunning view overlooking picturesque West River... this is an IDEAL getaway from it all for the Summer '25. And the cherry on top.. EVERYTHING is included

Wilkie Bushby TPW Real Estate

23 Old School Rd Unit the Barn, Londonderry, VT 05155
/6
$122,500 Sold Apr 18, 2025
- Land
- 2.20 Acres
- $55,682 per Acre
- 53 Days On Market
10 Little Brook Rd, Winhall, VT 05340

Prime 2.2-acre building lot in the desirable Vermont Ventures community! Conveniently located less than 15 minutes from Stratton Resort and Bromley, just 20 minutes from Manchester. This property includes a wastewater permit for a 5-bedroom home, with power available at the road, Little Brook is a town-maintained road, there is a ROW for access to the lot. With some clearing, the property offers

Lauren Behm Berkshire Hathaway HomeServices Stratton Home

10 Little Brook Rd, Winhall, VT 05340

/31
Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,215 Sq Ft
6 Black Birch Rd, Winhall, VT 05340

6 Black Birch Rd, Winhall, VT 05340

/59
$1,200,000
- 3 Beds
- 3.5 Baths
- 4,054 Sq Ft
4 Garden Loop Rd, Winhall, VT 05340

Your Stratton Mountain retreat awaits! This beautiful turnkey mountain home just off the Stratton Mountain Road is the perfect location for family gatherings, ski trips, hiking and more. This three-bedroom, three-bath home on three levels includes a breathtaking great room with a stone fireplace and vaulted ceilings. Dining room and additional breakfast area next to the kitchen. A large open

Lucy Ferrada Heney Realtors - Element Real Estate (Montpelier)

4 Garden Loop Rd, Winhall, VT 05340
/29
$30,000 per month
- 3 Beds
- 3 Baths
- 1,650 Sq Ft
- Townhouse for Rent
90 Turkey Run Rd, Winhall, VT 05340

Intervale Rental. Available for the winter 25-26 winter season. Also available for summer or fall monthly rental. Entry mud room for boot storage. Main floor has wood burning fire place, and the deck off the living room is a overlooks the pond. Main floor has primary suite. Two bedrooms plus a sleeping loft on the upper floor. One bedroom has an en suite bathroom, and a hallway full bathroom

Christiane Carroccio TPW Real Estate

90 Turkey Run Rd, Winhall, VT 05340
/37
$615,000 Sold Apr 15, 2025
- 1,500 Sq Ft
- $410/SF
- 39 Days On Market
- 3 Beds
- 2 Baths
- Built 1982
29 Burnt Hill Rd, Winhall, VT 05340

Discover your dream chalet in the heart of Strattonwald—a stunningly renovated retreat designed for year-round mountain adventures and modern comfort! Beautifully renovated 3-bedroom, 2-bathroom home in Winhall offers the perfect blend of convenience and recreation. Just a quick drive to Stratton Mountain, this property provides easy access to winter slopes and summer fun. The community amenities

Andie Fusco Four Seasons Sotheby's Int'l Realty

29 Burnt Hill Rd, Winhall, VT 05340

/33
Est $546,189 Not Listed For Sale
- 2 Beds
- 1 Bath
- 1,344 Sq Ft
935 Old Manchester Rd, Peru, VT 05152

935 Old Manchester Rd, Peru, VT 05152

/52
$629,000
- 3 Beds
- 3 Baths
- 1,650 Sq Ft
11 Pond View Rd, Winhall, VT 05340

Spring skiing & boarding is upon us & you can still close on time to enjoy it! Intervale community has long been popular for affordability and value. This bright and sunny unit boasts an updated kitchen, primary suite on the main level with updated bath. Mini suite on upper level along with a third bedroom and shared bath with the loft area. Heating system replaced with an efficient Buderus

Terry Hill Berkshire Hathaway HomeServices Stratton Home

11 Pond View Rd, Winhall, VT 05340
/40
$850,000 Sold Apr 04, 2025
- 3,119 Sq Ft
- $273/SF
- 168 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1996
36 Road To Millbrook, Winhall, VT 05340

This impeccably maintained home sits on 5.28 acres of beautifully landscaped land adjacent to the National Forest. Featuring a spacious interior with a stone wood-burning fireplace and vaulted cathedral ceilings, this home is move-in ready. Recent upgrades include two newly renovated bathrooms. The first floor offers an open living layout, while the lower level boasts a cozy den/family room.

Timothy Apps Four Seasons Sotheby's Int'l Realty

36 Road To Millbrook, Winhall, VT 05340

/35
Est $571,781 Not Listed For Sale
- 3 Beds
- 3 Baths
- 1,577 Sq Ft
10 Pond View Rd, Winhall, VT 05340

10 Pond View Rd, Winhall, VT 05340

/48
$2,780,000
- 5 Beds
- 7 Baths
- 7,625 Sq Ft
19 Old Town Rd, Bondville, VT 05340

Experience Vermont luxury at 19 Old Town Road, Winhall—a stunning 5-bedroom, 7-bathroom estate on 21.53 private acres. Built in 2000, this meticulously designed retreat offers unobstructed views of both Stratton Mountain and Magic Mountain.The spacious great room is the heart of the home, featuring soaring ceilings, a grand stone fireplace, and walls of windows that frame breathtaking

Christiane Carroccio TPW Real Estate

19 Old Town Rd, Bondville, VT 05340
/41
$2,100,000 Sold Apr 04, 2025
- 5,300 Sq Ft
- $396/SF
- 248 Days On Market
- 5 Beds
- 4.5 Baths
- Built 1974
20 W Ridge Rd, Stratton, VT 05360

OPEN HOUSE. Friday July 5th, 2-4pm. All Welcome.The exquisite craftsmanship of this stunning Austrian-style chalet evokes the lure of Stratton's early days. A location that was selected for incredible views, and close ski trail access. This true mountain haus has been thoughtfully updated to preserve its charm and authenticity. Imagine waking up to incredible mountain views every morning and

Christiane Carroccio TPW Real Estate

20 W Ridge Rd, Stratton, VT 05360

/31
Est $707,757 Not Listed For Sale
- 2 Beds
- 3 Baths
- 1,375 Sq Ft
78 Middle Ridge Rd Unit 106, Stratton, VT 05155

78 Middle Ridge Rd Unit 106, Stratton, VT 05155

/39
$2,999,000
- 6 Beds
- 6.5 Baths
- 6,650 Sq Ft
25 Mountain Haunts Rd, Winhall, VT 05340

Attend the PUBLIC OPEN HOUSE Monday February 17 from 10:00-2:00. Exceptional 40.8 acre newly expanded and renovated Stratton Mountain estate with unrivaled views of Stratton just minutes from the Base Lodge or Sun Bowl. This is your own personal winter playground where you can hit the slopes or snowmobile and hike on your own land with additional acreage available.This Grand Lodge NOW BOASTS 4

Kim Morgan-Wohler Wohler Realty Group

25 Mountain Haunts Rd, Winhall, VT 05340
/39
$1,250,000 Sold Apr 02, 2025
- 2,625 Sq Ft
- $476/SF
- 32 Days On Market
- 4 Beds
- 4 Baths
- Built 2003
6 Cranberry Ct, Stratton, VT 05360

Designed for mountain living, this expansive 4-bedroom, 4-bathroom townhome is the largest floor plan in Tree Top, offering unparalleledsquare footage and luxurious features. The property includes a total of 4 bedrooms, 3 are spacious primary suites with private baths, a cozy lower-level family room, and an open-concept great room adorned with a stone fireplace, soaring cathedral ceilings,

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

6 Cranberry Ct, Stratton, VT 05360

Showing Results 1 - 40, Page 1 of 18

Vermont South Londonderry

How to Buy a Home How to Finance a Home How to Sell a Home

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

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.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage