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

$619,900

3 Beds ⋅ 2 Baths ⋅ 73588375 MLS

Captivating from the first glance, this picturesque Ashland Gambrel offers the perfect blend of character, space and a prime location, keeping you right where you want to be! Walking distance to the Commuter Rail, local shops, The Corner Spot and the scenic trails and waterfall at Mill Pond Park and Riverwalk, this well-maintained home sits on a corner lot alongside a quiet side street with two cul-de-sacs. Inside, a spacious fireplaced living room with bay window flows into your flexible first-floor bedroom, currently used as a cozy den. An updated kitchen features gas cooking, granite countertops and an oversized island with direct access outside while a dining room and updated full bath finish out the first floor. Head upstairs to find two generously sized bedrooms, full bathroom and loft area, just waiting for you to grab a book and relax. Out back, a beautiful brand-new deck offers plenty of space for dining, lounging and entertaining, while overlooking a large, level yard with beautifully-maintained landscaping and mature trees. A newer roof, storage shed, full basement and new furnace and easy access to the Mass Pike, Rt. 9 and 495 add to the appeal. Full of character, comfort and flexibility, this special home offers the chance to enjoy the Ashland lifestyle--beloved for its schools, strong sense of community, parks and commuter convenience.

75 Myrtle Street, Ashland

$619,900

3 Beds ⋅ 2 Baths ⋅ 73588333 MLS

This 3BD, 2BA, 1,779 SF home in Ashland has just been updated and is ready for its new owners! The first floor features an open floor plan connecting the eat-in-kitchen (with new quartz countertop), living room and dining room. The full bathroom has a renovated tile bathtub with laundry. The 1st floor bedroom has newly added closet space. The 2nd floor features the primary bedroom with en suite bathroom that has an updated walk-in, tile shower. The additional bedroom on this floor also includes a new closet. Finally, the finished 3rd floor bonus space can be used as an office, play room or workout area. Outside there is a composite deck in back that was added in 2025. The driveway has 4 off-street parking spaces and a fixed basketball hoop. The yard also features a storage shed/workshop that includes interior lighting and power. This home is in a desirable location within walking distance of shops and restaurants on Rte 135 and easy access to other Ashland amenities. It is 1.2 miles to the MBTA commuter rail station on the Framingham/Worcester line, with easy access to Boston. It is only a half mile to downtown Ashland, 1.1 miles to Ashland State Park and 1.7 miles to Ashland Town Forest. Welcome to your new home!

10 Metropolitan Ave, Ashland

$1,180,000

4 Beds ⋅ 3 Baths ⋅ 73587194 MLS

Welcome to Ballard Hill Estates, where sophisticated living meets exceptional privacy and commuter convenience. Ideally situated on a quiet cul-de-sac in one of Ashland’s most sought-after neighborhoods, this beautifully appointed custom Colonial offers an inviting blend of timeless elegance, thoughtful updates, and versatile living spaces—just minutes from Route 90 and the commuter rail. From the dramatic two-story foyer, gleaming hardwood floors, generous proportions, and abundant natural light immediately set the tone. At the heart of the home, the stunning eat-in kitchen features custom white cabinetry, granite countertops, glass-front display cabinets, and high-end appliances, including a convenient beverage drawer. The kitchen flows seamlessly into the breathtaking family room, highlighted by soaring cathedral ceilings, a handsome traditional fireplace, and dramatic floor-to-ceiling windows that fill the space with natural light while framing peaceful views of the private backyard. The first floor is thoughtfully designed for both everyday living and entertaining, with an elegant formal dining room, spacious living room, and a private home office tucked behind a glass-paneled door. An updated half bath completes the main level. Upstairs, four generously sized bedrooms provide comfort and privacy. The luxurious primary suite features hardwood floors, an expansive walk-in closet, and a beautifully appointed bath with a large walk-in shower, jet tub alcove, custom his-and-her vanities, and private water closet. Three additional bedrooms, all with hardwood floors, offer generous closet space and flexibility for family, guests, or additional office space. The finished lower level adds another dimension of living space, ideal for a home theater, gym, playroom, recreation room, or gathering space. Outside, enjoy the serenity of the private backyard, bordered by wooded views and enhanced by a newer composite deck and patio with thoughtfully designed outdoor lighting. A large garden/storage shed provides additional functionality. An attached two-car garage with extra storage adds everyday convenience. Recent updates to the kitchen, baths, HVAC, lower level, deck, and patio complement the home’s meticulous maintenance and evident pride of ownership. A rare opportunity to enjoy refined living, exceptional versatility, privacy, and easy commuter access in one of Ashland’s most desirable settings.

19 Dearth Circle, Ashland

$1,350,000

4 Beds ⋅ 6 Baths ⋅ 73584996 MLS

This spacious new construction in Ashland features a modern, open layout with 4100 square feet of beautifully finished space; and a superior build quality with numerous luxury appointments, modern conveniences, and thoughtful details. Three of four bedrooms feature Walk In Closets and Private Baths. Fenced, nicely landscaped yard with custom stonework and a spacious rear deck. The convenient MetroWest location provides easy access to major routes and public transportation. Nearby local amenities include recreational opportunities as well as shopping and restaurants. This property has a great WalkScore® of 75.

17 Central, Ashland

$849,900

4 Beds ⋅ 3 Baths ⋅ 73579367 MLS

NEWLY REDUCED PRICE! An exceptional opportunity to own a spacious custom-built builder’s home offering quality craftsmanship, impressive room sizes and incredible versatility in a fantastic commuter location. Designed for comfortable everyday living and entertaining, this home features soaring ceilings, oversized windows, custom wood flooring, central air and efficient gas heat. A welcoming farmer’s porch opens to a dramatic foyer and thoughtfully designed main level featuring a private study, formal dining room, spacious living room with fireplace and a striking wall of glass overlooking the backyard. At the heart of the home, the generous kitchen offers a large center island, abundant workspace and an open flow to the main living areas. The primary suite located on the main living level provides a private retreat with generous closet space and a spacious bath. Also on the main level is a separate laundry room with utility sink, half bath and an oversized two-car garage with high ceilings and a convenient second stairway with direct basement access—ideal for storage, hobbies, equipment or larger projects. Upstairs offers three additional bedrooms, a full guest bath and a large bonus room ready to become a home office, gym, playroom, media room or additional living space. Need even more room? The expansive lower-level features a workshop, exceptional storage space and tremendous potential for future finished living space. Outside, a large deck overlooks a private backyard bordered by woods, creating a peaceful setting for relaxing, entertaining and enjoying the outdoors. A storage shed adds additional convenience. Best of all, enjoy privacy without sacrificing accessibility. Major commuter routes are nearby and the commuter rail is approximately 0.5 miles away. With its appealing new price, substantial square footage, flexible floor plan and custom details throughout, this is an outstanding opportunity.

39 Cordaville Rd, Ashland

$729,900

3 Beds ⋅ 3 Baths ⋅ 73579124 MLS

Red Post Realty is excited to present 8 Rodman Road, a stunning 3-bedroom, 2.5-bath home in Ashland! Fully renovated throughout, this exceptional property blends classic character with modern luxury, thoughtful design, and quality craftsmanship. The beautifully appointed kitchen features custom cabinetry, quartz countertops, a peninsula, built-in microwave, and premium stainless-steel Bosch appliances. White oak flooring, modern lighting, and abundant natural light create warm and inviting living spaces throughout.The beautifully renovated bathrooms showcase quartz finishes and distinctive designer details. Extensive improvements include all-new plumbing, electrical, HVAC, insulation, roofing, siding, windows, doors, drainage and waterproofing, along with a new driveway. Additional energy-efficiency upgrades provide modern comfort and peace of mind.Outside, enjoy a welcoming farmer’s porch with composite decking, professionally landscaped grounds, and attractive stonework. Ideally located near major routes, the commuter rail, shopping, restaurants, and all that Ashland has to offer. This move-in-ready home delivers the quality and finish of a high-end new build while maintaining the charm and character of an established Old New England Home.

8 Rodman Rd, Ashland

$1,199,000

4 Beds ⋅ 4 Baths ⋅ 73578895 MLS

Located on a quiet Cul de Sac and very close the Framingham Country Club with access to all major roads and shopping centers,this lovely 4 Bedroom 3.5 Bath Colonial with a new fence enclosing the total backyard and a front entryway with high quality marble stairs and extra exterior lighting has numerous updates.Recent renovations have been done to the 2 upstairs baths,and new attic flooring and and additional insulation.High quality roofing done in 2024,newer central air system heat pump and boiler,whole house generator,and new laminate flooring in the basement.Exterior has been freshly painted in 2021.The home with an open floor plan also has marble /tile,hardwood flooring,and granite countertops.The very spacious family room has a fireplace, recessed lighting,cathedral ceilings,and an adjacent spacious deck,and the living room has french doors and crown molding.A first floor office and formal dining room with crown molding add to the amenities.There are lots of options with the finished basement for a great workout or children’s play area or even a bonus room.

18 Pilgrim Rd, Ashland

$599,900

2 Beds ⋅ 3 Baths ⋅ 73574030 MLS

Enjoy easy living in this gracious 2-bedroom, 2.5-bath home in an intimate 55+ community offering a peaceful rural setting with convenient access to highways, shopping, dining, and everyday conveniences. The bright, open-concept main floor is perfect for relaxing or entertaining. The upscale kitchen opens to a dining area and a separate living room with vaulted ceilings, creating a spacious layout filled with natural light. A formal dining room provides additional space for gatherings. The first-floor primary suite features dual sinks, a separate tub, walk-in shower, and walk-in closet with laundry. A half bath completes the main level. Upstairs offers a second bedroom and full bath, ideal for guests, hobbies, or office space. Enjoy outdoor relaxation in the yard plus low-maintenance living with HOA landscaping and snow removal. Open House visitors: Please park in clubhouse spaces only, not in driveway or street.

30 Shadow Creek Lane Unit 30, Ashland

$1,999,900

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

$599,000

3 Beds ⋅ 3 Baths ⋅ 73557329 MLS

Commuters Boston-Bound – check out this fantastic Colonial 500 steps from the MBTA Ashland stop. If sunny open spaces and thoughtful upgrades are important to you, come see the terrific opportunity in this completely remodeled home. You will love waking up to beautiful sunrises across the Sudbury River and enjoy total peace of mind with new insulated windows, full foam insulation, 1st-floor laundry, efficient HVAC, a valuable whole-house Generac generator, gas heat, a garage and town water/ sewer. The updated kitchen boasts plenty of white cabinetry, butcher block counters and a breakfast bar which seamlessly connects to spacious living and dining areas, perfect for easy living and gracious entertaining. Upstairs features 3 bedrooms and two updated full baths, both with double sinks! The large primary suite offers a multi-closeted layout, lots of light and is a special space to unwind and relax. Unbeatable location in sought after Ashland near downtown shops, dining, State Park trails, and all major commuter routes. Although located on a busy street, it has surprising privacy and a big backyard with a covered deck overlooking woods! Motivated seller has priced this home to move, so act fast!

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.

35 Highwoods Trl, Ashland

Start Your Search

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

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 .