Ashland Homes with Colonial Style

Welcome to Ashland, a delightful city nestled in the heart of southern Oregon, renowned for its vibrant arts scene, stunning landscapes, and rich cultural heritage. With its charming downtown filled with boutique shops, gourmet restaurants, and the famous Oregon Shakespeare Festival, Ashland offers a unique blend of small-town charm and urban sophistication. The city's picturesque parks and proximity to the majestic Cascade Mountains make it an outdoor lover's paradise, perfect for hiking, skiing, and exploring the breathtaking natural beauty that surrounds it.

In this enchanting city, you’ll find a variety of architectural styles, but one that stands out is the timeless Colonial style. Homes with Colonial architecture in Ashland exude elegance and grace, characterized by their symmetrical facades, classic columns, and inviting front porches. These homes often feature spacious interiors with high ceilings, hardwood floors, and intricate moldings, creating a warm and welcoming atmosphere.

Living in a Colonial-style home in Ashland means embracing a lifestyle steeped in history while enjoying modern amenities. Whether you're hosting a gathering in your expansive living room or sipping coffee on your charming porch, these homes provide the perfect backdrop for cherished memories. The community’s commitment to preserving its historical charm ensures that these beautiful residences are not just houses but cherished homes that contribute to the unique character of Ashland.

Discover the allure of Ashland and the elegance of Colonial-style homes, where every corner tells a story, and every street invites you to explore and enjoy the rich tapestry of life in this beautiful city.

Newest Ashland Homes with Colonial Style

$2,149,000

6 Beds ⋅ 5 Baths ⋅ 73564757 MLS

Quietly tucked away at the cul-de-sac’s end, this grand Ashland residence delivers over 5,300 square feet of architectural grandeur and elevated living. Completely remodeled with bespoke updates throughout. The entrance commands attention with its dramatic quartz staircase framed by glass railings, high ceilings, and tailored interior millwork. Sun-soaked open interiors seamlessly flow into a state-of-the-art kitchen and open living areas. This beautiful and elevated luxurious home offers multi-level grand living with six bedrooms, four-and-a-half pristine baths with an adaptable lower level guest suite suited for relatives, guests or dedicated staff. A lavish primary suite boasts spa-grade quartz finishes, heated porcelain floors, custom stone, a soaking tub, and dual vanities. Below, find a fully finished entertainers dream space with Bose surround system inside and dozens of speakers outside on the pool deck. The amazing walkout lower level is warmed by radiant-heated porcelain tile where your private resort unfolds with an in-ground pool, serene Koi pond and a custom mini-golf course for high end entertainment in complete seclusion- the ultimate blend of sophistication, comfort, and lifestyle. Ashland luxury living at it finest. Schedule your private tour of this rare and luxurious Ashland residence before it's gone.

24 Old Connecticut Path, Ashland

$979,900

5 Beds ⋅ 4 Baths ⋅ 73563321 MLS

This inviting 5-bedroom, 3.5-bath colonial home is set on a generous, 3/4 lot, near the top of the hill. The sun-filled main level features a bright family room centered around a cozy wood-burning fireplace. The formal dining room flows into the kitchen with slider to a large deck, perfect for outdoor dining, entertaining, or relaxing. The main suite features 2 closets, ceiling fan, & a full bath. The 3 other bedrooms on this level are generous in size, and provide w/w carpeting. The lower level offers valuable additional living space with a kitchenette, bedroom, full bath, living area, and an office, ideal for in-law, au-pair, or over night guests ! The lower level has direct access to the rear yard. Heating system only 2yo. There is a large driveway leading to the 2 car attached garage. Underground utilities on the street. Walk to Mill Pond Park ! Thoughtfully designed for comfortable everyday living and effortless entertaining. New High Efficient Gas Heating System installed 12/24. Includes Security System w/ 2 cameras and Water Purification system under the Kitchen sink. .Close to Rt. 9, Mass. Pike, 495 etc.

73 Sudbury, Ashland

$1,295,000

4 Beds ⋅ 4 Baths ⋅ 73563084 MLS

Your private retreat awaits on Indian Brook Road. This custom-built 4 bed, 3.5 bath Colonial was designed for both everyday living and effortless entertaining, with an impressive array of amenities and resort-style outdoor space. At the heart of the home is the spacious family room, featuring a wood-burning fireplace, built-in shelving with a window seat and dramatic floor-to-ceiling windows that fill the space with natural light. The room flows seamlessly into the inviting eat-in kitchen with Thermador appliances and new LG refrigerator. The elegant dining room features a tray ceiling accented by sophisticated cove lighting, creating the perfect setting for gatherings and special occasions. The first floor offers exceptional flexibility; the private home office with a closet is located next to a full bath with a step-in shower. This versatile space could easily serve as a main level bedroom depending on your needs. Upstairs you will find the impressive primary suite, complete with a newly remodeled bathroom with soaking tub, two large walk-in closets and a spacious sitting area that provides a private sanctuary for quiet reflection with a beautiful view of the yard. Three generously sized guest bedrooms and a full guest bath round out the second floor. The finished basement provides even more living space and endless possibilities—perfect for a home gym, theater room, or playroom. Located on just under an acre of land, this home is set back from the road which allows for maximum privacy. The large composite back deck overlooks the serene in-ground saltwater pool. The dedicated pool house has a half bath, fridge, sink, outdoor shower and ample storage which makes summer entertaining exceptionally convenient. A private basketball sports court adds another dimension of recreation for family and guests. For nature lovers, the backyard offers something truly special: a trail that brings you to a wooden bridge over beautiful Indian Brook that allows you to hike directly to Hopkinton State Park. An attached two-car garage provides everyday convenience and additional storage.With generous living spaces, flexible accommodations, resort-style outdoor amenities, and direct access to nature, this property offers a rare opportunity to enjoy space, privacy, and comfort all in one exceptional home. A commuter's dream: located close to both the Southborough and Ashland MBTA stations. Easy access to Rt 9 and the Mass Pike.

49 Indian Brook Road, Ashland

$675,000

3 Beds ⋅ 3 Baths ⋅ 73557329 MLS

Discover this beautiful like-new Colonial in a prime walk to train location! This sun splashed home offers a flexible and inviting floor plan, featuring a spacious living room that opens seamlessly to the dining room, plus a bright sunroom ideal as a home office or cozy retreat. The beautifully updated kitchen showcases classic white cabinetry, stainless steel appliances, butcher block counters, and a convenient breakfast bar. A first floor half bath with laundry adds everyday ease. High ceilings, gleaming hardwood floors, and a mudroom entry with built in bench elevate the home’s charm and functionality. The private primary suite includes a new bath with double vanities and three closets, including a walk in. Nearly every major feature was updated in 2021—roof, windows, siding, floors, kitchen, and baths—offering peace of mind and modern comfort. Plus it even comes with a whole house generator! The gas heat, town water and sewer, and over 1,700 square feet of above grade living space make this home an exceptional value. Step outside to a covered deck overlooking a beautiful, private backyard framed by woods—your own serene oasis perfect for unwinding, entertaining, or enjoying nature. All of this in an unbeatable commuter location just steps from the Ashland MBTA station and close to downtown. Enjoy easy access to Routes 495, Mass Pike, and Route 9. Ashland offers highly regarded schools, fantastic restaurants and shops, and a spectacular state park filled with scenic trails and outdoor recreation. Come see!

329 Pleasant Street, Ashland

$424,000

3 Beds ⋅ 2 Baths ⋅ 5098601 MLS

Nestled on a private 1.5-acre lot, WITH DEEDED BEACH RIGHTS TO LITTLE SQUAM, this charming Colonial offers the perfect blend of comfort, updates, and outdoor living. Featuring 3 bedrooms and 1.5 baths, the home boasts an open-concept living and dining area that's ideal for everyday living and entertaining. Recent improvements include all-new flooring, beautiful butcher block countertops, and tastefully updated bathrooms, creating a fresh, move-in-ready feel. The partially finished lower level provides additional flexible living space, as does the hot tub room, while the mudroom and attached one-car garage add convenience for every season. Step outside to enjoy the farmer's porch, gather around the fire pit, or cultivate your favorite flowers and vegetables in the dedicated gardening space. As an added bonus, enjoy beach rights to beautiful Little Squam Lake either at your private beach area or as a resident you have access to the town beach, giving you easy access to swimming, kayaking, and lakeside relaxation. Conveniently located near shopping, skiing, hiking, boat marina's and all the attractions of New Hampshire's White Mountains, this home offers the perfect balance of privacy, recreation, and year-round enjoyment. DELAYED SHOWINGS UNTIL THE OPEN HOUSE on Saturday July 11th from 11:00-1:00.

35 Highwoods Trl, Ashland

$450,000

3 Beds ⋅ 2 Baths ⋅ 73531051 MLS

Attention all builders, contractors, investors: Rare opportunity to own ONE ACRE corner lot (44,829 sq ft) in Ashland. The existing home on lot is beyond repair. Seller had received permission for tear down however the New owner will need to re-apply with the Town of Ashland for tear down of the existing structure. Seller has spent a significant amount of time and money in clearing out the property. Home has the electricity still on but heat and running water are shut off. There is one town sewer connection available; buyer responsible for sewer hookup. Sold AS-IS, WHERE IS. Do not walk the lot without permission; use caution during showings. Property situated in an ideal location with short distance to Ashland Community Center, Ashland State Park, and MBTA Commuter Rail. Leverage this chance to bring your vision and building ideas as there are so many possibilities for this property!

9 Olive Street, Ashland

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