Ashland Homes for Sale

Welcome to Ashland, a picturesque gem nestled in the heart of Southern Oregon! Known for its vibrant arts scene, stunning natural beauty, and a strong sense of community, Ashland offers an idyllic lifestyle for those seeking a blend of culture and outdoor adventure. With the majestic Cascade Mountains as your backdrop and the serene waters of the Rogue River nearby, outdoor enthusiasts can enjoy hiking, biking, and rafting year-round.

Ashland is perhaps best known for the Oregon Shakespeare Festival, which attracts theater lovers from all over the world. This charming city is also home to delightful boutiques, gourmet restaurants, and local wineries, making it a haven for foodies and art aficionados alike. The friendly atmosphere and welcoming community make Ashland not just a place to live, but a place to thrive.

When it comes to homes for sale, Ashland boasts a diverse range of properties to suit every lifestyle and budget. From cozy bungalows adorned with character to modern family homes with spacious layouts, there’s something for everyone. Many properties feature stunning views of the surrounding mountains or are conveniently located near the vibrant downtown area, allowing residents to enjoy the best of both worlds.

Imagine waking up in a charming home, sipping your morning coffee while taking in the breathtaking landscape, or strolling through the lively streets filled with art and culture. Ashland is not just a destination; it’s a community where dreams can flourish. Explore our listings today and find your perfect home in this enchanting city!

Newest Ashland Homes for Sale

$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

$799,900

5 Beds ⋅ 3 Baths ⋅ 73585720 MLS

Though this is listed as a cape it is a unique layout with 5 levels the lowest being the basement. It has 4 bedrooms, aa bonus room, kitchen (with a parquet floor, wall oven, dishwasher, mico wave/vent hood and brand new unused gas range), dining room, Living room, garage and deck. This may seem confusing but is a must see. Located in a quiet neighborhood with a wooded lot and midway between downtown Ashland and the shopping on Route 126, Easy to show.

77 Warren Rd, Ashland

$449,900

4 Beds ⋅ 2 Baths ⋅ 5112277 MLS

Discover a truly unique New England property at the gateway to Squam Lake. This charming 3-bedroom home offers a warm, classic layout with a private office, spacious kitchen, and inviting living and dining spaces designed for comfortable living and easy entertaining. Adding exceptional versatility and income potential, the property includes a proven, five-star rental unit and a beautifully restored, fully insulated 1877 historic barn that has hosted more than 100 events. Perfect for gatherings, creative pursuits, a home-based business, or simply enjoying as an extraordinary bonus space, the barn offers possibilities rarely found in town. Set on half an acre, the property is within easy walking distance of local shops, restaurants, schools, parks, and community amenities, with quick access to I-93 and the Lakes Region and White Mountains. Whether you're seeking a primary residence with income potential, a multigenerational setup, or a distinctive live/work retreat, this special property offers character, flexibility, and endless possibilities in the heart of New Hampshire.

84 Main St, 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

$849,999

4 Beds ⋅ 3 Baths ⋅ 73583483 MLS

At 80 Winter St, Ashland, MA, an inviting single-family residence, constructed in 1979 and encompassing 1888 square feet of living space, stands ready for immediate occupancy. This property offers a unique blend of comfort and sophisticated living, set within an expansive 155,017 square foot lot, 3.56 acres. The kitchen is appointed with contemporary stainless-steel appliances, providing a functional and aesthetically pleasing environment for culinary endeavors. A well-appointed bathroom features a double vanity, enhancing daily routines with both convenience and style. The residence, a classic raised ranch, offers a seamless integration of indoor and outdoor living. A private yard provides a serene backdrop, complemented by an outdoor dining area and a patio, perfect for al fresco entertaining. The private pool offers an exclusive retreat for relaxation and recreation. This four-bedroom, three-full-bathroom residence, complete with a two-car garage and parking for 10, presents a compelling opportunity for discerning buyers seeking a distinguished lifestyle.

80 Winter St, Ashland

$599,000

3 Beds ⋅ 1 Baths ⋅ 73583169 MLS

Ideally located just south of Ashland Center and adjacent to Ashland State Park, this is a wonderful opportunity to enjoy all that this vibrant community has to offer—at a truly rare price point. Built in 1955, this charming Garrison Colonial features a fireplaced living room just off the entry, three bedrooms, and a spacious full bath. Just across the street, the Warren Center and Henry’s Place add another layer of convenience and recreation, with local residents able to take advantage of the Warren Center’s community club amenities, including pickleball, tennis, disc golf, trails, and select waterfront activities, while Henry’s Place offers a casual spot for coffee, lunch, dinner, or drinks. Ashland offers an appealing blend of small-town charm, outdoor recreation, and convenient MetroWest access, with parks, trails, local shops and restaurants, community events, and year-round recreational programs. The location also provides easy access to major routes and the MBTA Commuter Rail, making Boston and Worcester convenient destinations. Families are drawn to Ashland for its highly regarded public schools and strong sense of community.

452 Chestnut St, Ashland

$649,900

3 Beds ⋅ 2 Baths ⋅ 73582949 MLS

Fabulous opportunity in Ashland, MA! This home offers luxury finishes far beyond its price. Renovated gourmet kitchen features a chef’s dream: 48" Thermador dual-fuel range (gas cooktop/electric double ovens), paneled hood, quartz counters, and a massive 9ft+ island with seating & storage. Enjoy year-round comfort with updated HVAC (heating & cooling). The practical mudroom has built-ins and sliders leading to a private deck and an above-ground pool with solar cover and fenced backyard—perfect for entertaining! Main level boasts hardwood flooring in all three bedrooms, plus an upgraded full bathroom and stylish new interior doors. Lower level living shines with LVT flooring in the family room and office, a second full bath with shower, and a spacious tile laundry room. Lower level mini split and Navien Combi boiler installed 2023. The oversized garage provides significant storage and opportunity. Low maintenance and move-in ready! Excellent commuter location. Showings begin Thursday, Oct.1st.

29 Prospect St, Ashland

$539,000

1 Beds ⋅ 3 Baths ⋅ 73582759 MLS

Beautiful end unit lovingly maintained by the original owner. Large airy rooms with an open floor plan. The kitchen features warm wooden cabinety and a Corian counter top with a space for casual dining. The dining room is perfect for entertaining and is open to the large living room with its vaulted ceilings, two skylights, a lighted fan and a slider to the private side yard. The large bedroom has a great walk-in closet with access to the attic, three windows and wall to wall carpeting. The full bath has tile flooring, an oversized shower and a double vanity with a Corian top. On the second level there is a large loft and a full bath. It would be perfect as a family room, office or a guest area. All appliances are included in "as is" condation. Room sizes are approximate.

1 Haven Way Unit 1, Ashland

$899,000

4 Beds ⋅ 4 Baths ⋅ 73582464 MLS

Space to grow, room to entertain, and endless possibilities await at 31 Raymond Way! Set in a wonderful Ashland neighborhood, this solidly built, one-owner contemporary, owned by a builder, offers 4 bedrooms, 2 full and 2 half baths, a 2-car garage, and a gorgeous backyard with a large deck and inground pool. Step inside to freshly painted interiors filled with natural light, where high ceilings, abundant windows, and skylights create a bright and welcoming atmosphere. The family room connects to the living room, featuring a wood-burning fireplace and sliding doors to the deck overlooking the pool and backyard. Whether hosting summer gatherings or enjoying a quiet evening outdoors, this home offers an inviting setting inside and out. The spacious kitchen opens to the dining room, creating a comfortable flow for everyday living and entertaining. A half bath and interior access to the 2-car garage complete the first floor. Upstairs, the primary suite features a cathedral ceiling and private full bath. Three additional spacious bedrooms and another full bath provide plenty of room to spread out. The finished lower level adds flexible space for a recreation room, home office, or gym, along with laundry and a half bath with potential to expand to a full bath. With updating reflected in the price, this home presents a wonderful opportunity to bring your style and vision to a property with generous space, distinctive character, and solid construction. Enjoy the convenience of Ashland’s MetroWest location with access to commuter rail, Route 9, the Mass Pike, and I-495, plus shopping, dining, parks, and trails. A beautiful neighborhood, your own backyard retreat, and the opportunity to make it all your own—this is a home you can grow into and enjoy for years to come!

31 Raymond Way, Ashland

$575,000

3 Beds ⋅ 2 Baths ⋅ 73581623 MLS

Welcome to this charming Cape offering a flexible floor plan and inviting spaces throughout. The first floor features a bright kitchen that opens seamlessly to the formal dining room. An oversized family room provides plenty of space to gather, along with a dedicated area perfect for a home office. A full bath and spacious primary bedroom with en suite complete the main level. Upstairs, you will find two generously sized bedrooms. The lower level offers even more versatility with laundry, a flexible bonus space ideal for a home office, playroom, or gym, plus a large unfinished area offering endless possibilities for storage or future expansion. Outside, the fully fenced backyard features ample green space and a patio, ideal for outdoor dining, play, entertaining, and everyday enjoyment. A wonderful opportunity to enjoy comfortable, flexible living in Ashland!

112 Myrtle Street, Ashland

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