31

Homes for Sale near Ashland High School

Section Image Section Image
  • /33

    $425,000

    • 2 Beds
    • 2 Baths
    • 962 Sq Ft

    94 Pleasant St Unit 96, Ashland, MA 01721

    Looking for an affordable way to make it home in popular Ashland? This 2 bedroom, 2 full bath half-duplex may be your answer! You'll find stylish tile and hardwoods throughout, and the extensive renovations throughout will make the upkeep of your new home practically effortless! Whip up dinner in your eat-in kitchen, or grab takeout from one of the several nearby restaurants and enjoy it in

    Agent Photo

    Robert Smith

    Mathieu Newton Sotheby's International Realty

    (508) 219-7041

    94 Pleasant St Unit 96, Ashland, MA 01721
  • /41

    $839,900

    • 3 Beds
    • 2.5 Baths
    • 1,884 Sq Ft

    17 Stagecoach Dr, Ashland, MA 01721

    Well maintained single family raised ranch with newly refinished gleaming hardwood floors, cathedral ceilings, living room with a brick fireplace, eat in kitchen with granite countertops and stainless steel appliances, dining room with a slider to the private back deck with steps down to a patio and backyard. Hallway leads to main full bath, main bedroom with a full bath and two more bedrooms!

    Scott Hughes New Dover Associates, Inc.

    17 Stagecoach Dr, Ashland, MA 01721
  • /32

    $539,900

    • 2 Beds
    • 2.5 Baths
    • 1,967 Sq Ft

    102 Captain Eames Cir, Ashland, MA 01721

    Located in the desirable Starlight Village, this 2-bedroom tri-level townhouse awaits you. The 1st-floor features an open concept floorplan including a cozy living room with fireplace, a 1/2 bathroom, dining area and a kitchen complete with peninsula and direct access to the deck. The 2nd-floor features 2 spacious bedrooms, each with vaulted ceilings and its own ensuite bath, including a

    Benjamin Hause Keller Williams Realty North Central

    102 Captain Eames Cir, Ashland, MA 01721
  • /41

    $939,900

    • 4 Beds
    • 2.5 Baths
    • 2,888 Sq Ft

    6 New Castle Rd, Ashland, MA 01721

    This well maintained home is located in an awesome neighborhood with gorgeous landscaping close to everything including, shopping, restaurants, commuter train, state park, highway access, and schools! You're going to LOVE the layout of the main level! Huge eat-in kitchen with center island, hardwood floors, stainless steel appliances opens wide to a grand size family room with gas fireplace,

    Craig Morrison Realty Executives Boston West

    6 New Castle Rd, Ashland, MA 01721
  • /37

    $759,000

    • 2 Beds
    • 2.5 Baths
    • 2,307 Sq Ft

    20 Braeburn Ln, Ashland, MA 01721

    Single stand-alone 2300+sf in Ashlands premier active adult community abutting walking trails to Hopkinton state park. This home features so much on one floor plus additional space on the 2nd for guests. Step on FRONT PORCH and enter the spacious entry. On left is a large light-filled den/office/sitting room and to your right a large dining room open to the kitchen. The beautiful wood cabinetry

    Judi Teller Realty Executives Boston West

    20 Braeburn Ln, Ashland, MA 01721
  • /37

    $799,900 Open Sat 12PM - 2PM

    • 4 Beds
    • 2.5 Baths
    • 2,389 Sq Ft

    8 Raymond Way, Ashland, MA 01721

    Discover elegance and comfort at 8 Raymond Way, Ashland, MA — a beautifully maintained 4-bedroom, 3-bathroom home that blends style, space, and functionality in one of Ashland’s most coveted neighborhoods. With light-filled, inviting living areas, an open layout ideal for entertaining, and quality finishes throughout, this property offers both immediate move-in appeal and long-term value. The

    John Grande Media Realty Group Inc.

    8 Raymond Way, Ashland, MA 01721
  • /2

    $999,900

    • 5 Beds
    • 4.5 Baths
    • 3,614 Sq Ft

    101 Olive St, Ashland, MA 01721

    welcome to 101 Olive st in beautiful Ashland. With 3 combined lots totaling just over 14 acres this could be a great opportunity to develop or to own some privacy. There is a single family home on the property that has a full inlaw apartment or could be used as a 2 family property. All 3 properties sold together and as is. Each unit has its own laundry hook ups. Upstairs unit has 3 bedrooms, 2

    Ariana Faubert Noble Realty & Consulting, LLC

    101 Olive St, Ashland, MA 01721
  • /25

    $1,115,000

    • 5 Beds
    • 2.5 Baths
    • 3,220 Sq Ft

    28-30 Olive St, Ashland, MA 01721

    A truly rare find—two single-family homes on one oversized 18,750 SF lot, perfect for multi-generational living, an income-producing rental, or a savvy investment. The main home at 30 Olive St. offers 3 bedrooms, 1.5 baths, a two-car garage, semi-finished basement, and a recently renovated kitchen with granite counters and modern flooring. Step outside to your above-ground pool and brand-new

    Daniel Alper Boston Realty Advisors

    28-30 Olive St, Ashland, MA 01721
  • /26

    $899,000 Open Sat 2PM - 3:30PM

    • 3 Beds
    • 2.5 Baths
    • 2,354 Sq Ft

    20 Mulhall Dr, Ashland, MA 01721

    Tucked away at the end of a quiet cul-de-sac, this beautifully updated and energy-efficient home offers comfort, flexibility, and long-term savings—perfect for those seeking privacy and a peaceful lifestyle. Major 2018 upgrades include a new roof, HVAC, electrical, and hardwood floors. The finished lower level expands your living space with a spacious family room, guest bedroom, playroom, and

    Frederica Tassis Century 21 North East

    20 Mulhall Dr, Ashland, MA 01721
  • /38

    $469,000

    • 3 Beds
    • 2.5 Baths
    • 1,456 Sq Ft

    277 Meeting House Path, Ashland, MA 01721

    Seller to pay ALL 2026 special assessment! Impeccable and updated 2 bedroom condo with an extra room on main floor (den with closet). The tiled entryway leads into the impeccable hardwood floors in the living room, den, dining area and kitchen. The updated kitchen offers stainless steel appliances, granite countertops and white cabinetry w/ access to the exclusive use stone patio. The full bath

    The Premier Team Realty Executives Boston West

    277 Meeting House Path, Ashland, MA 01721
  • /32

    $495,000 Open Sat 12PM - 2PM

    • 2 Beds
    • 2.5 Baths
    • 1,785 Sq Ft

    23 Spyglass Hill Dr, Ashland, MA 01721

    OH - 10/11, 12-2pm - Welcome to Spyglass Hill - A wonderful community w/all your needs steps or moments away! Fantastic sun filled freshly painted townhouse offering spacious rooms throughout including a fireplaced living room, grand dining room perfect for entertaining large gatherings & a fully applianced eat-in-kitchen all of which have access to the private deck to extend your entertaining

    Anne Silverman LAER Realty Partners

    23 Spyglass Hill Dr, Ashland, MA 01721
  • /33

    $585,000 Open Sat 11AM - 1PM

    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft

    203 Pleasant St, Ashland, MA 01721

    Welcome to this delightful 3-bedroom, 1-bath single-family home nestled in a quiet, desirable neighborhood in Ashland. This lovingly maintained property offers comfort, flexibility, and room to grow perfect for first-time buyers, downsizers, or anyone looking to add their personal touch. Step inside to find a bright and inviting living space that flows seamlessly into the eat-in kitchen, ideal

    Scott Bascom eXp Realty

    203 Pleasant St, Ashland, MA 01721
  • /41

    $498,000 Open Sat 1PM - 3PM

    • 3 Beds
    • 2 Baths
    • 1,674 Sq Ft

    74 Meeting House Path, Ashland, MA 01721

    Move in Ready 3 Bed , 2 bath townhome in the Ledgemere Country Condominium of Ashland. Building within the community is at a nice locaation. Grand 2 story foyer and staircase leading to the second floor. Generous living space and ample kitchen cabinetry with eat in space. Open Layout. Sun drenched dining & Living space with a slider that leads to a private yard. First floor bed and full bathroom

    Kiran Kumar Gundavarapu Key Prime Realty LLC

    74 Meeting House Path, Ashland, MA 01721
  • /35

    $589,900

    • 3 Beds
    • 1 Bath
    • 1,220 Sq Ft

    56 Woodland Rd, Ashland, MA 01721

    ONLY 1 Fabulous UPDATED CONTEMPORARY STYLE RANCH from $475-$700K!!..nearly 2/3 Acre level lot, &lovely ended side St. Enjoy Oak HardWd. Flrs, C/AC... Beautiful Stainless Appl. Country Kitchen w-Fountain Faucet, French Dr.Refrig., 5-Burner Induction Range, Dishw, WindowBenchSeat w-storage, Tiled backsplash & Flr. SPACIOIUS Gorgeous LIV.Rm. w/WoodStv.&Pretty Bay Window. SEMI-VLTD. FAM.Rm.w-3 Sides

    Joyce Torelli ERA Key Realty Services - Distinctive Group

    56 Woodland Rd, Ashland, MA 01721
  • /17

    $500,000

    • 3 Beds
    • 1.5 Baths
    • 2,260 Sq Ft

    9 Olive St, Ashland, MA 01721

    The Otis Cole House, one of the first Greek Revival homes in Ashland & former start to the Boston Marathon, is now for sale for the first time in decades. Sitting on 1.49 acres, this corner lot is located steps from the Ashland Community Center, Ashland State Park, & 2mi from Commuter Rail, is an excellent opportunity for a builder’s next project. The existing home, built in the 1850s, carries

    Justin Rollo Signal Real Estate

    9 Olive St, Ashland, MA 01721
  • /41

    $489,900

    • 3 Beds
    • 1 Bath
    • 1,410 Sq Ft

    181 E Union St, Ashland, MA 01721

    Nestled on a spacious lot in a desirable Ashland neighborhood, this 1940-built home offers a rare opportunity to create your dream space. While the property does need updates and repairs, it features strong bones, character-filled details, and several key improvements including an updated furnace, newer windows, and a professionally installed TripleSafe sump pump system with battery backup. The

    The Best Buy Team Media Realty Group Inc.

    181 E Union St, Ashland, MA 01721
  • /33

    $639,900 Open House 10/19

    • 2 Beds
    • 2.5 Baths
    • 2,000 Sq Ft

    379 Captain Eames Cir, Ashland, MA 01721

    Welcome to this meticulously maintained, and beautifully updated multi-level townhouse in Ashland's Village of a Thousand Pines. This home features two spacious bedrooms, each with its own ensuite bath, including a primary suite with vaulted ceilings, walk-in closet, and fireplace. The finished lower level offers a flexible family room and dining area, ideal for relaxing or entertaining. The

    Mykayla Best Lamacchia Realty, Inc.

    379 Captain Eames Cir, Ashland, MA 01721
  • /33

    $489,900

    • 3 Beds
    • 1 Bath
    • 1,376 Sq Ft

    13 Clark St, Ashland, MA 01721

    This property has SO MUCH potential but best of all is the amazing location! Walk to downtown and just minutes to the train station, shopping, restaurants, Ashland State Park, schools, and highway access. Situated in a nice neighborhood with an absolutely beautiful level yard, this home has charm AND character and plenty of room for seating on the front porch! Spacious living room with hardwood

    Craig Morrison Realty Executives Boston West

    13 Clark St, Ashland, MA 01721
  • /42

    $2,149,000 Open Sun 12PM - 1:30PM

    • 5 Beds
    • 4.5 Baths
    • 5,357 Sq Ft

    24 Old Connecticut Path, Ashland, MA 01721

    Introducing a rare masterpiece in Ashland, privately set at the end of a cul-de-sac. This contemporary residence blends soaring ceilings, sun-filled open spaces, and over 5,300 square feet of refined living with bespoke upgrades throughout. A dramatic quartz staircase with glass railing sets the tone for luxury design, complemented by custom architectural ceilings and tailored millwork. The home

    Jeff Groper Coldwell Banker Realty - Newton

    24 Old Connecticut Path, Ashland, MA 01721
  • /36

    $474,900

    • 3 Beds
    • 2.5 Baths
    • 1,616 Sq Ft

    63 Trailside Way Unit 63, Ashland, MA 01721

    Experience the perfect blend of serenity and convenience in this beautifully updated 3-bedroom, 2.5-bath townhome. Nestled in a quiet, peaceful setting, yet just a short walk to shopping, dining, and entertainment, this home truly offers the best of both worlds. Upon entering, you'll be greeted by a stunning vaulted ceiling. The kitchen with granite and stainless steel appliances is open to the

    Lori Penney ERA Key Realty Services

    63 Trailside Way Unit 63, Ashland, MA 01721
  • /40

    $699,900

    • 2 Beds
    • 2.5 Baths
    • 2,196 Sq Ft

    343 Captain Eames Cir Unit 38-C, Ashland, MA 01721

    EXCEPTIONAL opportunity to own at sought-after Village of a Thousand Pines! Introducing 343 Captain Eames Circle* Fully updated and loaded FOUR story townhouse with hardwoods, fresh paint, modern open floor plan, two car garage, central air, gas fireplace, two primary suites with private baths, finished lower level walk-out. New PRIVATE stone patio and deck for outdoor enjoyment and unwinding.

    Kristine Wingate Shifrin Andrew J. Abu Inc., REALTORS®

    343 Captain Eames Cir Unit 38-C, Ashland, MA 01721
  • /33

    $499,999 Open Sun 11AM - 12PM

    • 2 Beds
    • 1.5 Baths
    • 1,492 Sq Ft

    126 Mountain Gate Rd Unit 126, Ashland, MA 01721

    Seller will pay first six months of condo fees at closing. Welcome home to this beautifully updated condo, perfectly blending comfort and style! The open-concept kitchen and dining area showcase brand-new white shaker cabinets, stainless steel appliances, and recessed lighting. A sliding door off the dining space leads to a large front deck, ideal for morning coffee or evening relaxation. The

    Jared Rowland Lamacchia Realty, Inc.

    126 Mountain Gate Rd Unit 126, Ashland, MA 01721
  • /18

    $569,000 Open Sat 11:30AM - 12:30PM

    • 2 Beds
    • 2.5 Baths
    • 1,616 Sq Ft

    76 Algonquin Trail, Ashland, MA 01721

    Step into this beautifully maintained and sun-filled 2-bedroom, 2.5-bathroom condo, where space, warmth, and convenience come together in one exceptional home. The highlight of the living area is the generous family room, featuring gleaming hardwood floors, a gas fireplace, and huge windows that flood the space with natural light. Flowing seamlessly into the dining area and oak kitchen, complete

    Prudence Hay Rutledge Properties

    76 Algonquin Trail, Ashland, MA 01721
  • /42

    $669,000

    • 3 Beds
    • 2 Baths
    • 2,191 Sq Ft

    17 Sewell St, Ashland, MA 01721

    Move right into The Good Life with this easy to maintain home! Built in 2005, this open-concept contemporary offers 2,191 sqft of living space, including lower level bonus room perfect for home office/gym. A right-sized yard & driveway means less time working--more time relaxing! Enjoy the convenience of living just off Rte 126 alongside the serenity of being tucked away on a freshly paved

    The Icon Group Keller Williams Pinnacle MetroWest

    17 Sewell St, Ashland, MA 01721
  • /29

    $549,900 Open Sun 12:30PM - 2PM

    • 2 Beds
    • 2.5 Baths
    • 1,967 Sq Ft

    262 Captain Eames Cir, Ashland, MA 01721

    Discover the charm of this stunning tri-level townhouse in Ashland, MA! This home features two spacious bedrooms, each with its own ensuite bath, including a primary suite featuring a walk-in closet for added luxury. The finished lower level offers a cozy family room, perfect for relaxation or entertaining. Enjoy the convenience of a two-car garage and the beauty of two expansive decks, perfect

    William McMahon McMahon Natoli Realty

    262 Captain Eames Cir, Ashland, MA 01721
  • /5

    $1,599,000

    • 4 Beds
    • 4.5 Baths
    • 3,800 Sq Ft

    9 Adams Rd, Ashland, MA 01721

    Stunning new construction (photos for illustrative purposes only) offering exceptional style and functionality. The open-concept layout showcases a chef’s kitchen with high-end appliances, center island, and premium finishes. A mudroom with built-in bench adds everyday convenience. Soaring ceilings and abundant natural light enhance the spacious feel. The main level includes a luxurious primary

    Christine Norcross William Raveis R.E. & Home Services

    9 Adams Rd, Ashland, MA 01721
  • /19

    $482,000

    • 2 Beds
    • 2 Baths
    • 1,224 Sq Ft

    306 Trailside Way, Ashland, MA 01721

    Welcome to this beautifully maintained 2-bedroom, 2-bath condo located in desirable Spyglass Hill. This inviting home offers a range of recent upgrades, including newer carpet, water heater, washer and dryer, refrigerator, updated kitchen countertops, and refreshed bathroom fixtures, providing a move-in ready opportunity for its next owner. The condo includes two garage spaces in a convenient

    Boaz McMahon Blue Fin Realty

    306 Trailside Way, Ashland, MA 01721
  • /41

    $1,749,900 Open Sun 2PM - 3:30PM

    • 4 Beds
    • 4.5 Baths
    • 3,900 Sq Ft

    22 Irene Cir, Ashland, MA 01721

    HIGHLY DESIRABLE BRANDEIS UNIVERSITY LOCALE NEAR WESTON LINE! SPECTACULAR HIGH-END new construction home featuring a beautiful modern kitchen w/oversized island and hidden pantry, sunfilled living room w/fireplace, formal dining for entertaining, bright primary bedroom w/stunning full bath and walk-in-closet, fully finished lower level family room, office and separate full bath, ready to finish

    Dave DiGregorio Jr. Coldwell Banker Realty - Waltham

    22 Irene Cir, Ashland, MA 01721
  • /38

    $649,900

    • 2 Beds
    • 2.5 Baths
    • 2,098 Sq Ft

    43 Haven Way, Ashland, MA 01721

    Single-Family 55+ condo FRESHLY PAINTED TOP TO BOTTOM overlooking the woodlands/trails of Ashland State Park and next to the Ashland Senior Center! This spacious home boasts so much living space on just one floor, with additional space on the second floor. A comfortable first-floor den off the main entry has a vaulted ceiling and lovely arched window. Gleaming hardwood floors and a wood-burning

    Judi Teller Realty Executives Boston West

    43 Haven Way, Ashland, MA 01721
  • /35

    $1,074,900 Open Sat 11:30AM - 1PM

    • 4 Beds
    • 3.5 Baths
    • 3,849 Sq Ft

    15 Pennock Rd, Ashland, MA 01721

    Northeast-facing, 4 bed, 3.5 bath colonial with pool in sought-after Apple Ridge Estates. Grand two-story foyer w REFINISHED HARDWOODS welcoming you into a bright & versatile home. Home office w NEW carpet. Elegant dining room featuring French doors & hardwood floors. Sun-drenched eat-in kitchen w white cabinetry & NEW quartz counters, hardware & fixtures, GAS CONN. for cooking, breakfast bar, &

    Kim Foemmel Foemmel Fine Homes

    15 Pennock Rd, Ashland, MA 01721
  • /5

    $1,450,000

    • 4 Beds
    • 3.5 Baths
    • 2,900 Sq Ft

    1 Adams Rd, Ashland, MA 01721

    New Construction to be built. (Photos are illustrative to be built) This luxurious free-standing home offers the rare opportunity to select your own finishes. Meadows Edge at Whitney Farm is a distinctive community comprising both free-standing and attached luxury homes, nestled on 30 acres of serene conservation and meadow lands. Each meticulously crafted home boasts open floor plans, hardwood

    Christine Norcross William Raveis R.E. & Home Services

    1 Adams Rd, Ashland, MA 01721
How to Buy a Home How to Finance a Home How to Sell a Home