Ashland Real Estate

Welcome to Ashland, a vibrant gem nestled in the heart of Southern Oregon! Known for its stunning landscapes and rich cultural heritage, this charming city is a haven for those seeking both adventure and tranquility. With a population of just over 20,000, Ashland combines the warmth of a close-knit community with the amenities of a bustling town.

One of Ashland's most notable features is its thriving arts scene, highlighted by the renowned Oregon Shakespeare Festival, which attracts theater enthusiasts from around the globe. The city is also home to numerous galleries, studios, and live music venues, making it a cultural hotspot. Stroll through its picturesque downtown, lined with boutique shops, cozy cafes, and farm-to-table restaurants that celebrate the region’s local bounty.

For nature lovers, Ashland is a paradise. Surrounded by the stunning Siskiyou Mountains and lush forests, residents and visitors can enjoy a plethora of outdoor activities, from hiking and biking to skiing in the winter months. Lithia Park, a sprawling green space in the center of town, offers serene walking trails, picnic areas, and beautiful duck ponds, perfect for a leisurely afternoon.

Education is a cornerstone of the community, with Southern Oregon University providing a vibrant campus atmosphere and contributing to the city’s youthful energy.

With its unique blend of culture, nature, and community spirit, Ashland is not just a place to live; it’s a place to thrive. Whether you're looking to settle down or invest in a vacation home, Ashland welcomes you with open arms and endless possibilities. Come explore the magic of Ashland—where every day feels like a new adventure!

Newest Listings in Ashland

$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

$619,900

2 Beds ⋅ 2 Baths ⋅ 73588187 MLS ⋅ ['Leah Estates'] BLDG.

A peaceful setting, generous living spaces and the ease of single-level living come together in this free-standing home within one of Ashland’s desirable 55+ communities. Welcome to Leah Estates! This detached home enjoys a special setting with Ashland State Park creating a wooded backdrop just beyond the deck. Inside, soaring ceilings, Palladian windows and hardwood flooring bring light and character to the open living spaces. The vaulted living room is anchored by a propane fireplace, while the adjoining dining area offers plenty of flexibility for everyday meals or entertaining. An expansive eat-in kitchen provides granite counters, abundant cabinetry & sunny dining area with access leading outside to the new deck. Both bedrooms and two full baths are conveniently located on the main level, including a spacious primary suite with a private bath and exceptional storage. Downstairs, the large unfinished basement opens the door to future possibilities...from billiards to ping-pong or finished living area for your guests you'll have space for it all without compromising on storage. Your two-car attached garage is an added enhancment to the ease of daily life. Leah Estates can be as social or as private as you choose, with a clubhouse and an active activities calendar offering plenty of vibrant opportunities to connect when the mood strikes. Just steps away, the Ashland Senior Center offers even more programs, activities and resources, while the commuter rail, state beach and everyday conveniences are all within easy reach. It’s a low-maintenance lifestyle with the space, setting and flexibility to make it entirely your own.

45 Haven Way Unit 24, 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

$365,000

3 Beds ⋅ 2 Baths ⋅ 5112884 MLS

Welcome to the Village at Riverbend, where comfortable condo living meets four-season recreation in the heart of Central New Hampshire. This 3-bedroom, 2-bath townhouse-style condo offers three levels of living space, providing plenty of room to spread out whether you're looking for a year-round home or a New Hampshire getaway. The main level offers comfortable living and dining space with access to a patio overlooking the peaceful wooded surroundings—an inviting spot for morning coffee, outdoor dining, or relaxing after a day of adventure. Upstairs, the spacious primary bedroom features its own private balcony facing the woods, where you can unwind and enjoy beautiful sunsets through the trees. Two additional bedrooms and the multi-level layout provide plenty of flexibility for family, guests, or a home office. Residents of Riverbend enjoy access to an outdoor pool and hot tub, tennis courts, walking trails, and the Pemigewasset River with a sandy beach area perfect for relaxing, kayaking, or spending a summer afternoon by the water. Conveniently located just minutes from downtown Plymouth and Plymouth State University, with easy access to I-93, Squam Lake, skiing, hiking, golf, snowmobiling, and all that the White Mountains and Lakes Region have to offer. With three bedrooms, two outdoor living spaces, and a peaceful wooded setting, this Riverbend townhouse offers a wonderful opportunity to enjoy the best of New Hampshire in every season.

6 Vista Dr Unit 94, Ashland

$599,900

2 Beds ⋅ 3 Baths ⋅ 73585844 MLS ⋅ ['The Village Of Westerly'] BLDG.

IMMACULATE & MOVE-IN READY! Privacy abounds in this Meticulously Updated and Improved Townhouse at Algonquin Trail! This Highly Desirable Galleria Style Unit features a Sunlit 2 Story Foyer; Beautiful New Kitchen thoughtfully remodeled with Custom Crafted Cabinetry, Quartz Countertops, Stainless Appliances, Tiled Back Splash and access to Large Deck; Sun-filled Dining Room and Living Room with gas fireplace; Fabulous Primary Suite with Cathedral Ceilings, Walk-in Closet, Gas Fireplace and Full Bath with Double Vanity, Jacuzzi tub and Shower; Spacious 2nd Bedroom with Cathedral Ceilings and en-suite Full Bath. Other features include a Cozy Loft and a Finished Lower Level Exercise Room with slider to 2 Private Patios. Extended Driveway offers Ample Parking! Great commuter location to nearby T-Station, Shopping and Restaurants! Major System Updates, New Kitchen, 2 Patios, even a Generator...the list goes on and on! Seller is willing to include some select pieces of furniture; see list provided. QUICK CLOSING POSSIBLE! A Must See!

244 Algonquin Trail Unit D, 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

$79,999

5112187 MLS

Pemigewaset Water Front Lot. 0.07 Acres of Commercial Zoned lot, build whatever you want with approvals. High Visibility on Rt3.

0 Rt 3 & N. Ashland Road, Ashland

$399,900

2 Beds ⋅ 2 Baths ⋅ 73584497 MLS ⋅ ['Ledgemere County Condominiums'] BLDG.

Space, flexibility and a corner-unit setting give this Ashland townhouse plenty to offer, along with an opportunity to add your own finishing touches over time. Set within Ledgemere Condominiums, this two-level home offers two bedrooms, 1.5 baths and hardwood flooring throughout much of the main living space and both bedrooms. The remodeled kitchen features stone counters, stainless steel appliances, gas cooking, a breakfast bar and generous cabinetry, flowing into the dining and living areas. While some cosmetic updates would bring a fresh new look, the home offers a solid foundation, great space and the chance to make it your own. The finished basement room adds valuable bonus space for a family room, office, gym or game room, with direct garage access for added practicality especially for those chilly winters. A private wood deck, central air, in-unit laundry, under-unit garage and additional paved parking add to the appeal. Improvements include a new HVAC system in 2020, remodeled kitchen, newer windows and storm door, fire door in the garage and Q-system garage door opener. With shopping, parks, trails, commuter rail and major routes nearby, this is a great opportunity to bring your vision to a well-located Ashland townhouse.

203 Leland Farm Road Unit 203, Ashland

$669,000

2 Beds ⋅ 2 Baths ⋅ 73583960 MLS ⋅ ['Leah Estates'] BLDG.

Welcome home to effortless one-level living in one of Ashland’s most desirable 55+ locations. This pristine free-standing home offers 1690 SF and sits on a premium lot backing up to peaceful conservation land (Ashland State Park), offering the perfect blend of privacy and convenience. Located just minutes from the commuter rail, Reservoir Beach, and the community center, this turnkey property checks every single box.Step inside to a bright, airy floor plan highlighted by high ceilings, gorgeous palladian windows and beautiful hardwood floors. The heart of the home is an expansive 24x13 eat-in kitchen featuring durable Corian countertops, abundant cabinet space, updated appliances and a sunny breakfast room with sliders to the back deck. The kitchen flows seamlessly into the casually dramatic, vaulted living room centered around a sleek propane fireplace—ideal for relaxing or entertaining. The casual dining room inspires with its cathedral ceiling & openness. The thoughtful layout features two spacious first-floor bedrooms and two ceramic full bathrooms. The primary suite is designed for comfort with a spa-like bathroom offering a whirlpool tub & both bedrooms offer ceiling fans. Outside, the wonderful private deck abuts the forest, providing a serene backdrop for morning coffee or evening cookouts while watching birds and enjoying nature. Additional features include: A brand new heat pump (2026) for AC and heating down to a 25 degree outside temperature. Hot water heater (2022) Upgraded appliances. A two-car attached garage and low-maintenance vinyl siding with gutters! The spacious unfinished basement offers incredible potential for future expansion of a home gym, pool table room, workshop space or game room & it's sure to please. Neutral designer colors throughout. Terrific clubhouse too!

41 Haven Way Unit 41, Ashland

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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 .