4,216

Middleton, MA Homes

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  • /34

    $1,898,000

    • 4 Beds
    • 3.5 Baths
    • 5,263 Sq Ft

    15 Couture Way, Middleton, MA 01949

    Welcome to 15 Couture Way - This exceptional residence offers the perfect blend of luxury, space, and comfort in one of Middleton's most sought-after new communities. Set on nearly an acre of beautifully maintained land, this 4-bedroom, 3.5-bath home spans over 5,200 square feet of living space and features a 3-car garage, an open-concept floor plan, and premium finishes throughout. Built just 2

    Daniel Resop William Raveis R.E. & Home Services

    15 Couture Way, Middleton, MA 01949
  • /42

    $1,525,000 Sold Jul 31, 2025

    • 3,992 Sq Ft
    • $382/SF
    • 7 Days On Market
    • 4 Beds
    • 4 Baths
    • Built 1993

    5 Cabral Dr, Middleton, MA 01949

    Arrive at 5 Cabral Drive and you'll be instantly charmed by this 4000 sq. ft Colonial home with meticulous landscaping and private grounds.This exquisite home boasts pride of ownership, showcasing numerous upgrades and custom built-ins. The sun-filled 1st floor features a great room with a built-in entertainment center,custom bar, 50+ bottle,wine fridge, gas fireplace, coffered ceiling with

    Cammy Bille J. Barrett & Company

    5 Cabral Dr, Middleton, MA 01949
    • /41

      Est $1,447,262 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 4,438 Sq Ft

      17 Sgt Roode Ln, Middleton, MA 01949

      17 Sgt Roode Ln, Middleton, MA 01949
  • /37

    $724,000

    • 3 Beds
    • 2 Baths
    • 1,881 Sq Ft

    77 Essex St, Middleton, MA 01949

    Motivated Sellers! All reasonable offers considered! 77 Essex Street rests idyllically on a generous and serene lot and has been lovingly maintained by the same family for over 50 years. This home features three bedrooms, two bathrooms, beautiful hardwood floors, and a spacious and private yard well-suited for outdoor enjoyment. The family room, featuring a cozy fireplace, elegant hardwood floors

    Chris Richardson The Richardson Group, LLC

    77 Essex St, Middleton, MA 01949
  • /36

    $441,000 Sold Jul 31, 2025

    • 1,209 Sq Ft
    • $365/SF
    • 42 Days On Market
    • 1 Bed
    • 1.5 Baths
    • Built 1975

    40 Village Rd Unit 807, Middleton, MA 01949

    Ferncroft Tower presents this beautiful upper-level one bedroom, 1.5 bath, 1209 s.f. condo. Enjoy magnificent sunsets from NEW walls of windows/sliders which open to your 25 ft. private balcony overlooking Ferncroft CC golf course, pool and mountains beyond. The fully applianced eat-in kitchen boasts granite counters, tile floor, cabinets galore, two pantries and includes newer washer/dryer. The

    Ann McGuiggin Country Crossroads Realty Associates LLC

    40 Village Rd Unit 807, Middleton, MA 01949
    • /42

      Est $1,375,568 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 3,053 Sq Ft

      3 James Ave, Middleton, MA 01949

      3 James Ave, Middleton, MA 01949
  • /35

    $300,000

    • Land
    • 6.67 Acres
    • $44,978 per Acre

    196-200 B1 N Main St, Middleton, MA 01949

    Raw Land in a Lovely setting. Approved Building Plans on File with Town for a Duplex. Set back from street with views of Emerson Brook Reservoir and Harold Parker. Convenient to shopping and major Routes. Lot B1 - 6,67 Acres also available adjacent lots. Abutting lot with house available at $600,000 additional.

    John Magazzu Charlesgate Realty Group LLC

    196-200 B1 N Main St, Middleton, MA 01949
  • /42

    $2,500,000 Sold Jul 29, 2025

    • 6,609 Sq Ft
    • $378/SF
    • 11 Days On Market
    • 4 Beds
    • 4 Baths
    • Built 2014

    5 Kassiotis Ln, Middleton, MA 01949

    Worthy of a magazine cover, this custom built Spanish Villa inspired home leaves nothing to be desired. From the Old World Aldor doors to the imported clay terracotta roof tiles to the old growth Hickory wood floors to the beams built with Douglas Fir timbers. The kitchen is a chef's dream with a grand island containing refrigerated drawers, Thermador appliances and imported Italian travertine

    Chris Richardson The Richardson Group, LLC

    5 Kassiotis Ln, Middleton, MA 01949
    • /36

      Est $1,227,698 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 3,615 Sq Ft

      6 Thornton Cir, Middleton, MA 01949

      6 Thornton Cir, Middleton, MA 01949
  • /42

    $650,000 Pending

    • 2 Beds
    • 3 Baths
    • 2,875 Sq Ft

    30 Maytum Way Unit 30, Middleton, MA 01949

    Offers due by Tuesday, 10/28 @12p. Your opportunity to own a townhome in the sought after Evergreen Estates. The tiled foyer leads to a versatile lower level with flex rooms, perfect for a home office, gym, playroom, or guest space. The main level boasts a lovely open floor plan with kitchen, dining & living area with fireplace, hardwood flooring & recessed lighting. The kitchen is an

    The Movement Group Compass

    30 Maytum Way Unit 30, Middleton, MA 01949
  • /39

    $756,650 Sold Jul 25, 2025

    • 2,633 Sq Ft
    • $287/SF
    • 7 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1985

    27 Fuller Pond Rd Unit 26, Middleton, MA 01949

    Desirable Fuller Pond Village, a Hidden Gem Just Off Rt. 114! This spacious end unit townhome features a bright, open-concept layout enhanced by oversized windows & skylights that flood the space with natural light. The eat-in kitchen offers ample cabinet & counter space. The adjacent living/dining area impress with soaring vaulted ceilings & French doors leading to a heated sunroom & private

    Lane Burnham Team LAER Realty Partners

    27 Fuller Pond Rd Unit 26, Middleton, MA 01949
    • /36

      Est $1,274,133 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,297 Sq Ft

      4 Thornton Cir, Middleton, MA 01949

      4 Thornton Cir, Middleton, MA 01949
  • /42

    $975,000 Pending

    • 3 Beds
    • 3.5 Baths
    • 2,473 Sq Ft

    8 Lebeau Dr, Middleton, MA 01949

    Welcome to Pond View Estates - An exceptional over 55+ Community. This Custom unit features 11 rms 3 bedrms, 3 1/2 baths, fantastic open floor plan boasting sunny livingrm w/gas fireplace, sitting area, cherrywood kitchen cabinets, center island, large palladium window over & access to deck, open to breakfast room w/peaceful views - perfect to enjoy your morning coffee, entertainment-size

    Wendy Carpenito Berkshire Hathaway HomeServices Commonwealth Real Estate

    8 Lebeau Dr, Middleton, MA 01949
  • /34

    $842,500 Sold Jul 23, 2025

    • 3,143 Sq Ft
    • $268/SF
    • 10 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 1792

    5 Elm St Unit 1, Middleton, MA 01949

    Renovated 3 bed, 3.5 bath condo with 2 car garage and private flat yard offering over 3000 of living area. Farm house style townhome with new windows, roof, updated heating and central air, updated kitchen and baths, hardwood and trex decking. First floor features living room, family room, eat in kitchen with soft close cabinets, quartz countertops, island and stainless steel appliances as well

    Brenna McNiff Coldwell Banker Realty - Beverly

    5 Elm St Unit 1, Middleton, MA 01949
    • /15

      Est $613,791 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,322 Sq Ft

      183 Boston St, Middleton, MA 01949

      183 Boston St, Middleton, MA 01949
  • /32

    $640,000 Pending

    • 2 Beds
    • 1 Bath
    • 1,120 Sq Ft

    123 Forest St, Middleton, MA 01949

    Rare opportunity to secure 1.5 acres of land in a prime Middleton location with limited conservation restrictions. This expansive, gently sloping lot abuts conservation land and protected land surrounding the Emerson Brook Reservoir, offering privacy and a unique natural setting. The existing two-bedroom, one-bath home is in good condition, with all systems in working order. The seller has

    DalBon & Company Keller Williams Realty Evolution

    123 Forest St, Middleton, MA 01949
  • /40

    $910,000 Sold Jul 21, 2025

    • 2,122 Sq Ft
    • $429/SF
    • 21 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1930

    53 Lake St, Middleton, MA 01949

    Charming hip roof colonial on a picturesque street with beautiful lake views. Warm and inviting, the first floor features a fireplaced living room, dining room, sunroom and updated kitchen with a center island, stainless appliances and granite countertops plus a 1st floor laundry and mudroom and updated full bath with tiled shower. On the second floor you’ll find a large primary bedroom with

    Sheri Trocchi J. Barrett & Company

    53 Lake St, Middleton, MA 01949
    • /35

      Est $1,515,183 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 4,550 Sq Ft

      10 Pollock Dr, Middleton, MA 01949

      10 Pollock Dr, Middleton, MA 01949
  • /29

    $929,000 Pending

    • 2 Beds
    • 2.5 Baths
    • 2,650 Sq Ft

    11 Cranberry Ln, Middleton, MA 01949

    Welcome to North Meadow Village, a 55+ community offering luxurious first-floor living. Step into this beautifully maintained home with perfectly kept hardwood floors, wainscoting, and crown molding throughout, complemented by high ceilings and bright, airy rooms. The heart of the home is the spacious kitchen, ideal for entertaining, featuring light cabinetry, stunning granite countertops, and a

    Nikki Martin Compass

    11 Cranberry Ln, Middleton, MA 01949
  • /41

    $1,580,000 Sold Jul 18, 2025

    • 4,403 Sq Ft
    • $359/SF
    • 6 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1999

    6 Bishop Ln, Middleton, MA 01949

    Get ready for Summer fun! This estate lot setting at Eddington Place offers an in ground pool, plenty of grassed areas, an oversized deck and patio area! The floor plan and upgrades have been well thought out and offer living the way you want it. The first floor open flow offers nice family gathering and entertaining possibilities. The Kitchen and Family Room open to the outside deck and have

    Gretchen Papineau Coldwell Banker Realty - Andovers/Readings Regional

    6 Bishop Ln, Middleton, MA 01949
    • /42

      Est $772,732 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,300 Sq Ft

      14 King St, Middleton, MA 01949

      14 King St, Middleton, MA 01949
  • /34

    $999,900 Pending

    • 4 Beds
    • 2.5 Baths
    • 3,404 Sq Ft

    30 Donovans Way, Middleton, MA 01949

    30 Donovans Way, Middleton-Upton Hills Area! Welcome to this 4 bedroom, 2.5 bath home with over 3,400 sq. ft. in the desirable Upton Hills neighborhood. The 25'x16' eat in kitchen easily seating 14+ guest for large gatherings. Attached deck with pool overlooking one private acre make this home ideal for relaxation and entertaining. Enjoy a family room with fireplace and cathedral ceilings, plus

    Ron Supino Berkshire Hathaway HomeServices Commonwealth Real Estate

    30 Donovans Way, Middleton, MA 01949
  • /42

    $840,000 Sold Jul 17, 2025

    • 1,840 Sq Ft
    • $457/SF
    • 8 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1963

    12 Edgewood Rd, Middleton, MA 01949

    Welcome to 12 Edgewood Rd! Enjoy this perfectly sized modern home which blends all the benefits of new construction without the hefty price tag! Enter into the open living space with vaulted ceilings with open designer kitchen and dining area with slider to brand new composite deck. This floor is completed by a primary suite with designer bathroom and two closets as well as second bedroom and

    Kristin Weekley Leading Edge Real Estate

    12 Edgewood Rd, Middleton, MA 01949
    • /42

      Est $713,370 Not Listed For Sale

      • 4 Beds
      • 1 Bath
      • 1,451 Sq Ft

      14 Mount Vernon St, Middleton, MA 01949

      14 Mount Vernon St, Middleton, MA 01949
  • /39

    $849,000 Pending

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

    34 Kenney Rd, Middleton, MA 01949

    NEW PRICE ALERT! 34 Kenney Road, a charming 3-bedroom, 2-bath home that blends comfort and nature. The living room features vaulted ceilings and a fireplace, opening to an eat-in kitchen and dining area perfect for entertaining. Upstairs, a walkway connects three bedrooms overlooking the living room, enhancing the open feel. a cozy family room can be closed off as a guest suite with a full bath.

    Ron Supino Berkshire Hathaway HomeServices Commonwealth Real Estate

    34 Kenney Rd, Middleton, MA 01949
  • /29

    $1,355,000 Sold Jul 16, 2025

    • 3,102 Sq Ft
    • $437/SF
    • 6 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2009

    18 Pinedale Rd, Middleton, MA 01949

    18 Pinedale Road is a picture-perfect young Colonial on a quiet street surrounded by acres of pastureland. This move-in ready home offers 3 finished levels with a stunning vaulted-ceiling great room, & a beautifully renovated first-floor executive office. The inviting eat-in kitchen features an awesome pantry & opens to a huge dining room perfect for all your large gatherings. Upstairs there are

    Candice Hodgson Lyv Realty

    18 Pinedale Rd, Middleton, MA 01949
    • /41

      Est $938,240 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,784 Sq Ft

      10 Wennerberg Rd, Middleton, MA 01949

      10 Wennerberg Rd, Middleton, MA 01949
  • /24

    $849,995 Pending

    • 2 Beds
    • 2.5 Baths
    • 2,159 Sq Ft

    31 Peaslee Cir, Middleton, MA 01949

    Rarely available in Middleton’s premier 55+ community with a super low & hard to find condo fee of ONLY $399!!! This move in ready 2+ bedroom, 2.5-bath residence features spacious bedrooms, including a luxurious 1st-floor primary suite with a spa-inspired bath complete with Jacuzzi tub, walk in shower, & expansive walk-in closet. The open-concept kitchen & cathedral ceiling living room area flow

    Candice Hodgson Lyv Realty

    31 Peaslee Cir, Middleton, MA 01949
  • /38

    $750,000 Sold Jul 10, 2025

    • 1,960 Sq Ft
    • $383/SF
    • 6 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2004

    129 River St Unit A, Middleton, MA 01949

    Set back from the road for ultimate privacy, this beautifully renovated 3-bedroom, 2.5-bath condo offers three levels of thoughtfully designed living space. This home has been fully updated, blending timeless style with modern comfort. Step inside to find a flexible layout that caters to any lifestyle, whether you're working from home, hosting guests, or simply relaxing in your own peaceful

    Charles King Real Broker MA, LLC

    129 River St Unit A, Middleton, MA 01949
    • /40

      Est $649,746 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,019 Sq Ft

      37 King St, Middleton, MA 01949

      37 King St, Middleton, MA 01949
  • /29

    $829,900 Pending

    • 3 Beds
    • 2 Baths
    • 2,100 Sq Ft

    166 Forest St, Middleton, MA 01949

    GREAT HOUSE GREAT LOCATION!PERFECT HOUSE NOTHING TO DO JUST MOVE-IN!!! Welcome to this charming Gambrel colonial home offering 3-bed, 2-baths , Situated in a sought-after neighborhood, it combines suburban tranquility with easy access to local amenities. Large back yard, big driveway, and partially finished walk-out basement add to the property's appeal. nothing to do just move- in.. a lot of

    Armando Vranari ALB Realty

    166 Forest St, Middleton, MA 01949
  • /42

    $390,000 Sold Jun 26, 2025

    • 769 Sq Ft
    • $507/SF
    • 39 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 2003

    36 Village Rd Unit 108, Middleton, MA 01949

    BOM due to change in buyer's personal circumstances. Picture yourself all moved into this lovely meticulously maintained 1 bedroom 1st floor luxury condo with 9' Ceilings and Oversized Windows!!! Bright and spacious open floor plan w/elegant living & dining area. A fully applianced kitchen w/pantry & laundry in unit. Master Suite has a fabulous walk-in closet, attached to full bath with large

    Luciano Leone Team RE/MAX 360

    36 Village Rd Unit 108, Middleton, MA 01949
    • /36

      Est $618,727 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,209 Sq Ft

      63 Maple St, Middleton, MA 01949

      63 Maple St, Middleton, MA 01949
  • /39

    $989,000 Pending

    • 3 Beds
    • 2.5 Baths
    • 3,172 Sq Ft

    49 Maple St Unit B, Middleton, MA 01949

    **SUNDAY OH CANCELLED OFFER ACCEPTED***Two years young! This beautifully maintained home offers 4 levels of spacious living. The 1st floor features an open concept layout with a DR and LR accented by gleaming HW flooring. The stunning kitchen boasts quartz countertops, SS appliances, and oversized center island and ample cabinetry. A convenient 1/2 bath and mudroom complete the main level.

    Roberta Peach CDG Realty Group

    49 Maple St Unit B, Middleton, MA 01949
  • /40

    $2,000,000 Sold Jun 26, 2025

    • 5,230 Sq Ft
    • $382/SF
    • 14 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2004

    10 Sawyer Ln, Middleton, MA 01949

    Welcome to desirable Ryebrook Estates. This 12 room 4 bedroom 3.5 bath situated on 3.47 acres of land surrounded by conservation area creates your hidden oasis. The tranquil setting allows outdoor enthusiasts to enjoy the heated inground pool and outdoor kitchen with friends and family. The tree lined private driveway leads to the main house and custom 3 car garage / barn with an additional 789

    Mike Cotraro Buckley Realty Group, Inc.

    10 Sawyer Ln, Middleton, MA 01949
    • /33

      Est $907,777 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,497 Sq Ft

      69 Maple St, Middleton, MA 01949

      69 Maple St, Middleton, MA 01949
  • /42

    $1,295,000 Pending

    • 3 Beds
    • 3.5 Baths
    • 4,000 Sq Ft

    10 Callaway Dr Unit 10, Middleton, MA 01949

    Elegant End Unit in Village Estates awaits you. This beautifully designed end unit is perfect for entertaining, featuring an open-concept first floor with hardwood floors throughout. The kitchen boasts custom cabinets, granite countertops, stainless steel appliances, and an oversized island. The living room offers soaring ceilings, built-ins, and a fireplace, with French doors leading to a

    Sharon Seabury Twin Pinnacle Realty

    10 Callaway Dr Unit 10, Middleton, MA 01949
  • /27

    $1,040,000 Sold Jun 25, 2025

    • 3,551 Sq Ft
    • $293/SF
    • 16 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1995

    5 Campbell Rd, Middleton, MA 01949

    Welcome to 5 Campbell Rd—a beautifully maintained home on a quiet, tree-lined street in one of Middleton’s most desirable neighborhoods. This home features a bright, open layout with spacious rooms, hardwood floors, and abundant natural light. The functional kitchen offers ample storage and flows into a cozy dining area and large family room—perfect for entertaining. The first-floor primary

    Brian Reardon Five Mark Realty Group LLC

    5 Campbell Rd, Middleton, MA 01949
    • /41

      Est $667,335 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 2,116 Sq Ft

      77 Maple St Unit 3, Middleton, MA 01949

      77 Maple St Unit 3, Middleton, MA 01949
  • /42

    $1,475,000 Pending

    • 5 Beds
    • 5 Baths
    • 4,623 Sq Ft

    19 James Ave, Middleton, MA 01949

    OPEN 10/4&5 from1130-1 Amazing opportunity to own this legal 2 family home with 4,623 sf of living space situated on 2.51 acres in the highly desirable Fieldstone Place neighborhood. Perfect for extended families and guests to enjoy this one owner multigenerational home. This home blends the comfort and convenience of a single home with the bonus of extra income produced with the 2nd unit.There

    Mike Cotraro Buckley Realty Group, Inc.

    19 James Ave, Middleton, MA 01949

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