Woodstock Homes under $500,000

Welcome to Woodstock, a vibrant city nestled in the heart of Ontario, Canada, where history meets modern living! Known for its rich heritage and stunning natural surroundings, Woodstock offers a unique blend of small-town charm and urban convenience. With its picturesque parks, bustling downtown, and a strong sense of community, it’s no wonder that families, professionals, and retirees alike are drawn to this delightful city.

Woodstock boasts a variety of amenities, including excellent schools, diverse dining options, and an array of recreational activities. You can explore the scenic trails of the nearby Thames River, enjoy local events at the Woodstock Art Gallery, or simply stroll through the historic streets lined with beautiful architecture. The city is also conveniently located just a short drive from larger urban centers like London and Kitchener, making it an ideal spot for commuters.

For those seeking affordable housing options, Woodstock is an excellent choice. The real estate market here offers a range of charming homes under $500,000, making it accessible for first-time buyers and families looking to settle down. From cozy bungalows to modern townhouses, there’s something to suit every taste and budget. Many of these properties come with spacious yards, perfect for enjoying the outdoors or entertaining friends and family.

In Woodstock, you’ll find not just a house, but a place to call home. Embrace the warmth of this community, and discover the perfect property that fits your lifestyle—all within a budget that works for you. Come and explore the opportunities that await you in beautiful Woodstock!

Newest Woodstock Homes under $500,000

$469,000

3 Beds ⋅ 3 Baths ⋅ 5112762 MLS

Coming Soon!!! Beautifully updated and maintained 3 bedroom 3 bath townhome with full finished basement in Alpine Village. Kitchen and bathrooms have all been renovated. New appliances, new flooring, and new windows too! This condo features an open style first level with kitchen, dining and living rooms and a 3/4 bath. There are two bedrooms on the second floor and and a full bath. The third bedroom is a bright sunny loft on the third level. Downstairs in the fully finished basement is a family room, including a wet bar, laundry, half bath, and a bonus room, great for sleep space, an office, play space, storage, or whatever you need! You can walk right outside from the basement to the back yard and trails. This is an ideal location, walking distance to downtown North Woodstock. Close to Loon and Cannon Mountains and all of the White Mountains area attractions. * All inquiries and requests for showings will be responded to after October 20, 2026.

12 Madison Dr Unit 83, Woodstock

$465,900

2 Beds ⋅ 2 Baths ⋅ 5112728 MLS

Where Mountain Living Meets Riverfront Charm! Welcome to your dream White Mountains retreat! This well maintained, completely renovated 2-bedroom, 2-bath condo sits in the most prime location within Deer Park with one of the best views of the Pemi River you could ask for. Step inside to discover an inviting open-concept layout where the kitchen, dining, and living areas flow seamlessly from room to room. Natural wood accents and a wood-burning fireplace create the quintessential New Hampshire ambiance you've been searching for. The master bedroom features a private en-suite bathroom, while a second bedroom and another full bath ensure comfort for the entire family or guests. Thoughtful updates including new kitchen cabinets, light fixtures, stainless appliances, updated baths w/granite featuring a custom walk-in tile shower in the master bath and Viessman heating system making this a true turnkey property. You’ll even marvel at the one of a kind river stone inlay in the kitchen breakfast bar illuminated with multi color Led lighting The Deer Park community is a four-season playground. The impressive clubhouse boasts an indoor pool, hot tub, cardio and weight rooms, racquetball & pickleball courts, and an inviting great room anchored by a double-sided stone fireplace. Summer days call you to the gorgeous 5-acre lake and sandy beach just steps from your door. Adventure seekers will love the proximity to Loon Mountain Resort, complete with seasonal shuttle service, along with easy access to Cannon Mountain, the scenic Kancamagus Highway, and the stunning Pemigewasset River. This is more than a home, it's a lifestyle waiting for you.

75 Riverfront Dr Unit 205, Woodstock

$359,900

4 Beds ⋅ 2 Baths ⋅ 5111583 MLS

Welcome to this beautifully maintained 4-bedroom, 2-bath home offering over 2,000 square feet of comfortable living space in a prime location. Ideally situated just minutes from Loon Mountain and walking distance to the Pemi River, this property offers the perfect combination of convenience, space, and outdoor enjoyment. Inside, you’ll find a bright, open-concept kitchen and dining area, along with two separate living room spaces providing plenty of room for entertaining, relaxing, or accommodating guests. The spacious primary suite features two generous walk-in closets, a jetted Jacuzzi tub, and a double vanity, creating a comfortable private retreat. Step outside to a large deck overlooking the nicely manicured backyard, where you’ll find an above-ground pool-perfect for summer gatherings. Picture warm afternoons by the pool, evening barbecues on the deck, and cool mountain nights spent relaxing with family and friends. Set on a slab, this double-wide offers generous living space and an exceptional location for year-round living, a vacation getaway, or investment potential. With easy access to the White Mountains, Loon Mountain, I-93, and downtown Lincoln/Woodstock, this property puts everything you need and love about the area close at hand.

811 Eastside Rd, Woodstock

$469,900

2 Beds ⋅ 2 Baths ⋅ 5110952 MLS

Have you ever wanted to listen to the river while sitting on your deck, if so then this garden style condo is perfect for you and your family! The entire unit is up to date including granite counter tops, updated kitchen cabinets, new bathroom vanities and all flooring throught the condo. You'll also enjoy the wood burning fireplace on those cold winter nights. When you own at Deer Park you'll have use of the nicest clubhouse in the Loon area. The club features an indoor pool, jacuzzi, weight room, cardio room, game room and a spring fed 5 acre pond with sandy beach for your summer enjoyment. During the winter months Deer Park offers shuttle bus to Loon and an outdoor skating rink. Come see this property for yourself. We know you'll be impressed.

29 Riverfront Dr Unit 256, Woodstock

15 Jack O Lantern Dr Unit Unit 34, Woodstock

$390,000

3 Beds ⋅ 2 Baths ⋅ 5110824 MLS

Welcome to Jack O’Lantern Resort! This well-maintained 3-bedroom, 2-bathroom condo offers a versatile layout with a spacious loft and lock-off suite, giving you plenty of options for family, guests, or rental use. The living room opens to a screened-in 3-season porch, creating a great spot to unwind and enjoy the peaceful surroundings. The condo has been exceptionally well cared for and is tucked into a quiet area of the resort while still being close to everything. If rental income is part of your plans, the property is ready to go and offers the potential to start generating income right away. Ask about the local rental management options and the popular Stay & Play packages offered in partnership with the Jack Golf Course. Owners enjoy access to a great selection of resort amenities, including an indoor heated pool, hot tub, outdoor pool, recreation room, basketball hoop, new playground, and tennis/pickleball courts. Outdoor enthusiasts will love the direct access to Corridor 11 for snowmobiling, with trailer storage available in the resort’s overflow lot. Located right next to the newly renovated Jack Golf Course, restaurant, and bar, this property is set up to be enjoyed in every season whether you're looking for a mountain getaway, a place to gather with family and friends, or a rental investment.

15 Jack O Lantern Dr Unit Unit 34, Woodstock

$379,900

3 Beds ⋅ 2 Baths ⋅ 5110667 MLS

This 3 bedroom, 2 bath townhouse in Alpine Village is perfectly located for all of your year-round adventures in the Loon area as well as being a quick minutes drive to Cannon Mountain and Franconia Notch. The restaurants and shops of downtown North Woodstock are just a short walk away. The first level of the house features an open concept living/dining room which has a newer propane fireplace to make those winter nights a little cozier. The kitchen looks out onto a private, grassy backyard which has ample space for a deck to be added. A 3/4 bath and laundry closet are also conveniently located on the main floor. There are three good-sized bedrooms and a full bathroom on the second level. After 2+ decades owned by the current family, this home is ready for the next winter to come make it their own and enjoy for years to come!

14 Adams Dr Unit #11, Woodstock

$449,000

3 Beds ⋅ 1 Baths ⋅ 5110580 MLS

This nicely updated ranch on a country acre is a rare opportunity to live in Woodstock without breaking the bank. Perfect for downsizing, one-level living, starting out, or even an easy-to-care for vacation home. There is plenty of storage for skis or other recreation equipment in the oversized two-plus car garage and two bay shed with a concrete floor. Sellers have spent 12 years gradually improving the property with new vertical wood siding, windows, doors, deck, stone steps, kitchen cabinets,appliances, wood flooring, interior doors and trim,radon mitigation system, a great mudroom entry and more. There are apple trees, a pear tree, gardens and a large fenced in area in back. Bourdon Maple Farm is just up the hill and the Ottauquechee River is across the road below the property. Recreation opportunities are abundant with mountain biking, hiking, skiing, racquet sports and swimming in town and beyond. Dining and Shops in Woodstock Village, Schools, Killington and Pico are all nearby. ArtisTree, Barnarts, Feast and Field and Pentangle Arts offer many opportunities for music, theater, movies, art classes and galleries all just minutes away. Everything that the the Upper Valley has to offer is less than an hour's drive away-including DHMC, Dartmouth College, shopping and dining galore. Don't miss this rare opportunity to own a home in a wonderful country setting convenient to everything at a reasonable price!

23 Biscuit Hollow Rd, Woodstock

$250,000

3 Beds ⋅ 1 Baths ⋅ 5110107 MLS

Nestled in the highly desirable Woodstock area, this property offers the perfect canvas for your vision. Featuring an older mobile home and a spacious barn, the possibilities are there for those looking to create a country retreat, hobby farm, workshop space, or future building site. The barn provides valuable storage or recreational use, while the existing mobile home offers a starting point for renovation, replacement, or temporary occupancy as you plan your next steps. Enjoy convenient access to Woodstock’s historic village, local shops, restaurants, outdoor recreation, and year-round attractions. Whether you're seeking a weekend getaway, an investment opportunity, or the foundation for your dream Vermont homestead, this property offers a rare chance to own a piece of the Upper Valley lifestyle. Bring your ideas and imagination. With its desirable location, existing infrastructure, and room to grow, this Woodstock property is ready for its next chapter.

5556 W Woodstock Rd, Woodstock

$220,000

1 Beds ⋅ 1 Baths ⋅ 5110020 MLS

Nicely updated and move-in ready, this 1-bedroom, 1-bath condo at the Alpine Lodge puts you right in the heart of North Woodstock. The second-floor location offers a comfortable open-concept living and dining area, an updated kitchen, spacious bedroom, full bath, and private front deck with beautiful mountain views. Location is hard to beat! The Pemi River is directly across the street for fishing, swimming, and summer fun, while hiking trails and outdoor adventures are just minutes away. Downtown North Woodstock is an easy two-minute walk, with local restaurants, breweries, shops, and more right at your fingertips. Loon Mountain is about 10 minutes away, Cannon Mountain 20 minutes, and Waterville Valley approximately 30 minutes. Fully furnished and ready to enjoy, this is an ideal White Mountains getaway or year-round home. Just bring your suitcase and settle into North Country living!

193 Main St Unit Unit 213, Woodstock

$400,000

2 Beds ⋅ 3 Baths ⋅ 5104834 MLS

Welcome to your new home or home away from home located in beautiful Woodstock NH. This unique townhome offers a versatile floor plan that is warm and inviting. Cozy up by the fireplace on those cold blister days or read a book in your bright sun room that has two levels of enjoyment. Need an extra space for guest? Utilize the loft for additional sleeping space, privacy, or quiet time. This home has 2 bedrooms and an office that could be used as an additional sleeping space, office, den, or bonus space. The primary bedroom has its own on suite bathroom and two large closets for storage. It opens up to the bright sunrooms lower level making this primary suite the perfect sanctuary. Every inch of this homes space has been utilized for efficiency and functionality. Take advantage of the community amenities that include inground pool, basketball court, and tennis court. This home unlike many townhomes also has a dry functional basement that can be accessed from the interior and exterior. The current owners are using for a workout area. To top it all of this unit comes with a 2 car garage. Home is listed $15,000 below appraised value. Get instant equity! The back deck is brand new. It has been replaced by the HOA since the photos have been taken.

7 Sundance Rd Unit 4, Woodstock

$195,000

2 Beds ⋅ 2 Baths ⋅ 5104613 MLS

property being sold by trustee, seller has no knowledge of age, or systems within the home. There is no Zoning in the town Woodstock. This property will need work to make it livable.

88 Lost River Rd, Woodstock

$450,000

3 Beds ⋅ 2 Baths ⋅ 5102664 MLS

Enjoy peace, privacy, and endless possibilities on 2 quiet acres, just 3 miles from downtown Woodstock! This adorable ranch-style double-wide offers a bright, open-concept kitchen, dining, and living area perfect for entertaining or relaxing by the wood-burning fireplace. Vaulted ceilings and abundant natural light enhance the spacious feel. The impressive kitchen features solid hickory cabinetry, stainless steel appliances, a tile backsplash, pot filler, apron-front sink, oversized island with extensive storage, and a charming window seat with additional storage. The primary suite includes a spacious bathroom with double sinks, a stand-up shower, soaking tub, and direct access from both the bedroom and bathroom to a large walk-in closet. The property’s standout feature is the nearly new, never-used, three-story barn measuring approximately 40' x 28'. With 14-foot ceilings and 13-foot entry doors, it is ideal for RV storage, classic cars, animals, a workshop, or other recreational uses. Above the barn is an additional 20' x 40' open space, accessed by interior stairs, offering approximately 800 square feet of storage or potential finished space. The barn may also offer future residential conversion possibilities, subject to all required permits and approvals. Additional features include a 30-amp electrical hookup in the driveway for an RV or hot tub, a lovely brook that feeds a private pond, and a peaceful mountain setting. Perfect for year-round living, a second-home getaway, or a potential Airbnb opportunity!

68 Russell Farm Rd, Woodstock

Start Your Search

board logo 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 .