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Homes for Sale in 01566

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  • /32

    $184,999

    $5K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,124 Sq Ft

    147 Pine Ave, Sturbridge, MA 01566

    Enjoy comfortable, low-maintenance living in this beautifully updated home located in a desirable 55+ community. Move-in ready, this spacious home features cathedral ceilings, a large eat-in kitchen with abundant cabinet and counter space, new appliances, and tasteful finishes throughout. The bright four-season sunroom provides additional living space perfect for relaxing or entertaining. Two

    Agent Photo

    Monique Frigon

    RE/MAX Generations

    147 Pine Ave, Sturbridge, MA 01566
  • /27

    $145,000

    $5K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 980 Sq Ft

    1 First St, Sturbridge, MA 01566

    Welcome to Sturbridge Retirement Cooperative 55+ community. This 2 bedroom 1 bath home built in 1980 is ready for its new owner. Spacious 3 season enclosed porch, oversized living area with vaulted ceiling and wood burning fireplace. Newer windows throughout , mini splits for air conditioning. Open floor plan, kitchen with center island. Easy 1 level living centrally located only minutes to area

    Agent Photo

    Lisa Caron

    Lisa Caron Real Estate LLC

    1 First St, Sturbridge, MA 01566
  • /17

    $359,900

    Open Sun 12PM - 3PM
    • 2 Beds
    • 2 Baths
    • 960 Sq Ft

    6 Pinrock Dr, Sturbridge, MA 01566

    QUICK CLOSE – LAST MOVE-IN READY HOME AVAILABLE FOR SPRING! Now is your chance to get into Blueberry Hill Estates without the wait. This thoughtfully designed home is perfect for downsizing buyers looking for low-maintenance living without sacrificing quality or comfort. Inside, you’ll find high-end finishes including stainless steel appliances, a farmhouse kitchen sink, full tile backsplash,

    Agent Photo

    Justin Stelmok

    J.W. Management & Sales, Inc.

    6 Pinrock Dr, Sturbridge, MA 01566
  • /28

    $150,000

    $10K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 980 Sq Ft

    131 Pine Ave, Sturbridge, MA 01566

    Welcome to Sturbridge Retirement Cooperative 55+ community. This 2 bedroom 1 bath home built in 1985 is ready for its new owner. Brand new propane furnace. Central Air, storage shed. Open floor plan, bright and sunny kitchen. Easy 1 level living centrally located only minutes to area markets, restaurants, shops and easy access to I-90, 84, 20. Monthly HOA includes water, sewer, trash, recycling,

    Agent Photo

    Lisa Caron

    Lisa Caron Real Estate LLC

    131 Pine Ave, Sturbridge, MA 01566
  • /16

    $399,900

    $5K PRICE INCREASE
    • 2 Beds
    • 2 Baths
    • 1,493 Sq Ft

    19 Pinrock Dr, Sturbridge, MA 01566

    ***PHASE 2 NOW OPEN FOR 2026*** Located just off of Fiske Hill, surrounded by conservation land, these homes feature one floor living with 2 bedrooms, 2 baths, & a den. Standard features include a stainless steel farmhouse kitchen sink, stainless steel appliances, tray ceiling & entertainment center in the living room (per plan), a 10’x12’ brushed concrete patio, central A/C, covered front porch

    Agent Photo

    Justin Stelmok

    J.W. Management & Sales, Inc.

    19 Pinrock Dr, Sturbridge, MA 01566
  • /19

    $456,900

    Open Sun 12PM - 3PM $62K PRICE INCREASE
    • 2 Beds
    • 2 Baths
    • 1,493 Sq Ft

    24 Pinrock Dr, Sturbridge, MA 01566

    NEW CONSTRUCTION | SUMMER 2026 MOVE-IN. Brand new Evoke model is here! Be moved in by end of the summer. Our most popular floorplan, this thoughtfully designed home features an open-concept layout, bright living space, and a modern kitchen with stainless steel appliances, farmhouse sink, and full tile backsplash. Central A/C, energy-efficient construction, and quality finishes throughout. Private

    Agent Photo

    Justin Stelmok

    J.W. Management & Sales, Inc.

    24 Pinrock Dr, Sturbridge, MA 01566
  • /37

    $500,000

    • 3 Beds
    • 2 Baths
    • 1,568 Sq Ft

    6 Belanger Ave, Sturbridge, MA 01566

    Located on a private dead end road, this charming 3-4 bedroom, 2 bath, updated Colonial farmhouse has so much to offer! Set on 8 plus wooded acres, this home is a nature lovers sanctuary with hiking, hunting, camping, and more all outside your door. Lovely eat-in country kitchen w/peninsula, granite counters & stainless appliances, Open concept living/dining room. First floor laundry area. The

    Agent Photo

    Carrie Abysalh

    RE/MAX Prof Associates

    6 Belanger Ave, Sturbridge, MA 01566
  • /15

    $245,000

    • Land
    • 1.15 Acres
    • $213,043 per Acre

    12 Carey Rd, Sturbridge, MA 01566

    Rare opportunity to build your dream home just steps from Leadmine Pond in a beautiful Sturbridge setting. This 1.15-acre residential lot is located directly across the street from Leadmine Pond, known for its clear water and recreational appeal, and offering convenient access for kayaking, canoeing, boating, hiking trails, and largemouth bass fishing. Surrounded by wooded landscape and nearby

    Agent Photo

    Laurie Casey

    Leading Edge Real Estate

    12 Carey Rd, Sturbridge, MA 01566
  • /19

    $456,900

    • 2 Beds
    • 2 Baths
    • 1,493 Sq Ft

    21 Pinrock Dr, Sturbridge, MA 01566

    NEW CONSTRUCTION | FALL 2026 MOVE-IN. Brand new Evoke model coming to Blueberry Hill Estates! Scheduled for July delivery with fall move-in. Our most popular floorplan, this thoughtfully designed home features an open-concept layout, bright living space, and a modern kitchen with stainless steel appliances, farmhouse sink, and full tile backsplash. Central A/C, energy-efficient construction, and

    Agent Photo

    Justin Stelmok

    J.W. Management & Sales, Inc.

    21 Pinrock Dr, Sturbridge, MA 01566
  • /18

    $265,000

    • 3 Beds
    • 1 Bath
    • 1,069 Sq Ft

    71 Shepard Rd, Sturbridge, MA 01566

    Welcome Flippers & Investors. This is your next project! There is money to be made. This split is located on a nice setting and needs to be emptied and renovated. It has been winterized to prevent damage. See attached septic info from the Board of Health. Seller is looking for a quick closing. Cash sales or hard money only. Please read disclosures.

    Agent Photo

    Maria Hopkins

    Maria Gruber Hopkins Associates

    71 Shepard Rd, Sturbridge, MA 01566
  • /34

    $649,000

    • 6 Beds
    • 5.5 Baths
    • 3,506 Sq Ft

    6 Newton Place, Sturbridge, MA 01566

    Multigenerational living or large home office opportunity! Nestled on a quiet cul-de-sac in Sturbridge's sought-after Fiske Hill neighborhood, this spacious Cape offers exceptional flexibility with 6 bedrooms and 51⁄2 bathrooms. The private 1.14-acre lot is a backyard retreat featuring an in-ground pool, greenhouse, garden area, and a large sun porch that opens directly to the pool. The versatile

    Julie Horrigan RE/MAX Prof Associates

    6 Newton Place, Sturbridge, MA 01566
  • /21

    $199,900

    • 2 Beds
    • 2 Baths
    • 1,056 Sq Ft

    117 Vista Ln, Sturbridge, MA 01566

    Enjoy peaceful living in this well-maintained home, ideally situated on a quiet dead-end street private, wooded, corner lot. This open-concept lay-out home features a beautiful kitchen flowing seamlessly into dining room & living, areas creating the perfect space for everyday living & entertaining! Large primary bedroom includes a walk-in closet & private full bathroom. A generously sized second

    Penny Cote LAER Realty Partners

    117 Vista Ln, Sturbridge, MA 01566
  • /8

    $299,000

    $151K PRICE DROP
    • Land
    • 2.19 Acres
    • $136,530 per Acre

    368 Main St, Sturbridge, MA 01566

    Opportunity to own commercially zoned land in the heart of Sturbridge. This parcel offers excellent visibility and frontage along Main Street, located in a high-traffic area surrounded by local businesses, restaurants, and attractions.While the land is currently non-buildable, it presents potential for future investment, land banking, or alternative permitted uses depending on town approvals. Its

    The Elevate Group Properties Central Realty

    368 Main St, Sturbridge, MA 01566
  • /12

    $850,000

    • 2 Beds
    • 2 Baths
    • 1,030 Sq Ft

    30 Whittemore Rd, Sturbridge, MA 01566

    Location, Location, Location! Rare opportunity to own over 16 acres in one of Sturbridge's most desirable locations. Adjacent to the historic district and just minutes from Routes 84, 20, and the Mass Pike, this unique property offers an exceptional combination of privacy, convenience, and potential. The land features a beautiful mix of open fields and wooded acreage, complemented by historic

    Dawn Truax Red Door Realty

    30 Whittemore Rd, Sturbridge, MA 01566
  • /27

    $549,000

    Open Sun 11:30AM - 1PM
    • 4 Beds
    • 3 Baths
    • 2,347 Sq Ft

    51 Whittemore Rd, Sturbridge, MA 01566

    Welcome home to this beautiful 3-4 bedroom Cape nestled in the highly desirable Fiske Hill neighborhood. Offering just under 2,400 square feet of thoughtfully designed living space, this flexible floor plan features an oversized main-floor bedroom along with an additional first-floor room that can serve as a second bedroom or the perfect home office. Upstairs, you'll find two generously sized

    Lexi O'Brien RE/MAX Prof Associates

    51 Whittemore Rd, Sturbridge, MA 01566
  • /20

    $425,000

    Open Sun 11AM - 1PM
    • 3 Beds
    • 2 Baths
    • 1,150 Sq Ft

    12 Fairground Rd, Sturbridge, MA 01566

    Charming Cedar Pond Waterfront Bungalow!Welcome to this adorable 3-bedroom, 2-bath waterfront bungalow nestled along the shores of beautiful Cedar Pond in Sturbridge. Full of character and thoughtful updates, this inviting home offers the perfect blend of charm, potential, and a peaceful waterfront lifestyle.Approximately 10-15 years ago, a second-story addition transformed the home by adding two

    JS & The City Team Serhant

    12 Fairground Rd, Sturbridge, MA 01566
  • /41

    $1,100,000

    • 4 Beds
    • 2.5 Baths
    • 2,688 Sq Ft

    50 Hillside Dr, Sturbridge, MA 01566

    Behind a quiet cul-de-sac lies a custom-built retreat where luxury & nature exist in perfect balance! Built in 2025 & set on 26.8 private acres, this exceptional home blends refined craftsmanship w/ modern design. An open-concept layout features a chef's kitchen w/ custom cabinetry, quartzite countertops,14x6 island, walk-in pantry, & seamless flow into the living & dining area. The luxurious

    James Black Real Broker MA, LLC

    50 Hillside Dr, Sturbridge, MA 01566
  • /37

    $729,000

    $71K PRICE DROP
    • 6 Beds
    • 4.5 Baths
    • 4,579 Sq Ft

    14 Maple St, Sturbridge, MA 01566

    Welcome to 14 Maple Street where timeless New England charm meets refined luxury. Meticulously maintained, this exceptional residence showcases preserved French doors, rich original hardwood floors, elegant crown molding, and sun-drenched interiors throughout. The beautifully remodeled kitchen features quartz countertops, under-cabinet lighting, and distinctive cork flooring, blending warmth with

    Cecelia Powers RE/MAX Generations

    14 Maple St, Sturbridge, MA 01566
  • /40

    $530,000

    $30K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,374 Sq Ft

    10 Maple St, Sturbridge, MA 01566

    Step into a rare piece of New England history at 10 Maple St in Sturbridge—a truly special former parsonage dating back to the 1800s. Rich with character and timeless charm, this historic property offers a unique opportunity to own a home with deep roots in the community while enjoying the warmth and comfort of private residential living. Having served exclusively as a private home since 1998,

    Joshua Patraw eXp Realty LLC

    10 Maple St, Sturbridge, MA 01566
  • /5

    $969,900

    New Construction
    • 4 Beds
    • 3 Baths
    • 3,540 Sq Ft

    558 Haynes St, Sturbridge, MA 01566

    Experience the perfect blend of style and functionality in this spacious contemporary Cape, ideal for those seeking single-level living with room to grow. The sunlit open kitchen features granite countertops, a 9’ center island, and breakfast bar, flowing into a Great Room with a cozy fireplace and an expansive dining area. The first-floor primary suite includes a luxurious en suite bath with

    David Stead RE/MAX Partners

    558 Haynes St, Sturbridge, MA 01566
  • /6

    $139,900

    • Land
    • 11.17 Acres
    • $12,525 per Acre

    29 Whittemore Rd, Sturbridge, MA 01566

    Large parcel is being offered for sale in the desirable town of Sturbridge. Located in the Fisk Hill area close to MA Pike, Interstate 84 and Route 20. Easy to commute. With 11.17 acres to build your dream Home and create your own private outside living. There is water and sewer on the street. Priced below accessed value. Bring an offer!

    Ingrid Karp Coldwell Banker Realty - Worcester

    29 Whittemore Rd, Sturbridge, MA 01566
  • /42

    $699,999

    $25K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 2,652 Sq Ft

    47 Old Village Rd, Sturbridge, MA 01566

    Sought after WALKER POND neighborhood w/ deeded beach rights! Great location with highway access to get to Boston, Providence or Hartford. This meticulous home has it all- a great neighborhood, unique flexible floor plan, 5 bedrooms, 3 baths & a fabulous deck for entertaining & watching the kids swim. Walk in to dining room which could be used as a sitting area. The living room has a vaulted

    Ann Marie Sorensen ERA Key Realty Services- Auburn

    47 Old Village Rd, Sturbridge, MA 01566
  • /36

    $27,900

    $4K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 532 Sq Ft

    19 Mashapaug Rd Unit C29, Sturbridge, MA 01566

    Motivated Seller! Willing to do private financing with down payment. NOTE: Can not live year round! May 1st- Nov1 Beautifully decorated inside and out, large deck for outside living. Sleeps 8. Full size tub with shower.Summer recreations include up at the lodge/store additional showers laundry free wifi so much more u need to come see for your self !Be a snowbird live here 6 months and somewhere

    Karynsue Marchione-Reilly Park Place Realty Enterprises

    19 Mashapaug Rd Unit C29, Sturbridge, MA 01566
  • /38

    $599,900

    Open Sat 12PM - 2PM
    • 3 Beds
    • 3.5 Baths
    • 3,006 Sq Ft

    120 Colonial Dr, Sturbridge, MA 01566

    Looking for something truly stunning? Located in the highly sought-after Sturbridge Hills community, this beautifully customized three-story End Unit Condo offers 3 Bedrooms and 31⁄2 Baths. The open-concept main level showcases gorgeous hardwood floors and a dramatic vaulted Living Room with a fireplace. Adjacent to the living area is the spacious Kitchen and Dining Area featuring upscale

    Lorraine Herbert RE/MAX Prof Associates

    120 Colonial Dr, Sturbridge, MA 01566
  • /2

    $994,900

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 3,113 Sq Ft

    9 Haynes St, Sturbridge, MA 01566

    Stunning New Colonial in a Premier Neighborhood! This beautifully crafted home features a striking exterior with multiple rooflines and a welcoming 20' farmer’s porch. Inside, enjoy a dramatic open floor plan with a spacious great room, gas fireplace, and 4-panel slider to a large deck—perfect for entertaining. The gourmet kitchen boasts a 10' island, granite countertops, and custom cabinetry. A

    David Stead RE/MAX Partners

    9 Haynes St, Sturbridge, MA 01566
  • /21

    $449,000

    • 3 Beds
    • 1 Bath
    • 2,091 Sq Ft

    212 Charlton Rd, Sturbridge, MA 01566

    Bring your business home with this commercially zoned property. Enjoy the convenience of operating your business just steps from your living space - the perfect work-life balance! Commuters take notice! This impeccably maintained custom ranch offers an unbeatable Sturbridge location just seconds from the Mass Pike, I-84, Route 20, and nearby shopping. Quality craftsmanship shines throughout with

    Julie Horrigan RE/MAX Prof Associates

    212 Charlton Rd, Sturbridge, MA 01566
  • /34

    $364,900

    $20K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 1,283 Sq Ft

    25 Sturbridge Hills Rd Unit 25, Sturbridge, MA 01566

    Seller has moved out! 25 Sturbridge Hill Rd. Sturbridge, MA. This attractive move in ready 1283 sq ft condominium, built in 1993, is in great condition and offers an exceptional opportunity for comfortable living. This second-floor residence encompasses two bedrooms, with new carpeting, providing comfortable and private spaces,2nd floor washer and dryer. A full bathroom with walk in shower and a

    Dan Robertson Coldwell Banker Realty - Worcester

    25 Sturbridge Hills Rd Unit 25, Sturbridge, MA 01566
  • /3

    $119,900

    • Land
    • 1.83 Acres
    • $65,519 per Acre

    235 Main St, Sturbridge, MA 01566

    Nearly 2 acres on Main Street/Route 131 in Sturbridge, ready for you to develop and fulfill your dreams!

    Maryellen Brunelle Michael Toomey & Associates, Inc.

    235 Main St, Sturbridge, MA 01566
  • /13

    $138,000

    $12K PRICE DROP
    • Land
    • 2.07 Acres
    • $66,667 per Acre

    29, 31, 33 Ladd Rd, Sturbridge, MA 01566

    Two lots, lot A is 2 acres lot and is perc tested, lot 33 is 1 acre lot. sold together. Very secluded yet close to everything, beautiful Old Sturbridge Village, great restaurants, schools and highways minutes away. MassPike, 84, 20, 9, 49

    Andrzej Bzura Top Notch Realty

    29, 31, 33 Ladd Rd, Sturbridge, MA 01566
  • /39

    $469,900

    • 3 Beds
    • 2 Baths
    • 2,050 Sq Ft

    37 Breakneck Rd, Sturbridge, MA 01566

    Charming post and beam saltbox colonial situated on a private 4.2-acre lot with direct pond frontage. It features a wraparound upper deck and an additional lower deck overlooking Breakneck Pond, with freshly painted decking for outdoor enjoyment. New carpeting in all three bedrooms, an open concept living and dining area that spans the back of the house, complete with a centrally located brick

    Kenneth Olson eXp Realty LLC - Corporate Office

    37 Breakneck Rd, Sturbridge, MA 01566
  • /7

    $1,500,000

    $490K PRICE DROP
    • Land
    • 36 Acres
    • $41,667 per Acre

    1 Chase Rd, Sturbridge, MA 01566

    Chase Road was previously approved for a 71 unit Multiple Dwelling Project. 24 acres for the town house style homes and 12 acres of open space on a 450 foot cul-de-sac. On the corner of Hall Road and Chase Rd. is a 2.4 acre commercial lot. This property is ideally situated, 1/2 mile to the on ramp to I84 and I90 behind Wendie's on Rt. 20. Providing exceptional access to Route 49, Rt. 20, Rt. 148,

    David Ford RE/MAX Prof Associates

    1 Chase Rd, Sturbridge, MA 01566
  • /21

    $160,000

    • 2 Beds
    • 1 Bath
    • 1,150 Sq Ft

    224 Park Cir, Sturbridge, MA 01566

    Welcome to Sturbridge Retirement Cooperative 55+ community. This spacious handicapped accessible 2 bedroom 1 bath home built in 1986 and is ready for its new owners. There is a spacious three season porch for your enjoyment. Enjoy this open concept faulted ceiling living room and kitchen. Cabinet packed eat-in kitchen is great for cooking and eating in the same space. Seller is providing a $5K

    Keith Hollett Coldwell Banker Realty - Worcester

    224 Park Cir, Sturbridge, MA 01566
  • /38

    $549,900

    Open Sun 11:30AM - 1PM
    • 4 Beds
    • 2.5 Baths
    • 2,741 Sq Ft

    90 Sturbridge Hills Rd Unit 90, Sturbridge, MA 01566

    Discover an exceptional living experience at 90 Sturbridge Hills Rd U:90, Sturbridge, MA. This condominium offers three levels of living space. The kitchen is designed for both functionality and gathering, featuring a peninsula with dining area to accommodate food prep and hosting. Recently renovated including new butcher block and appliances including a double oven. The living room, with vaulted

    Robin Riel Keller Williams Pinnacle Central

    90 Sturbridge Hills Rd Unit 90, Sturbridge, MA 01566
  • /42

    $624,900

    $25K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,851 Sq Ft

    39 Hillside Dr, Sturbridge, MA 01566

    Nestled on 1.05 acres in a cul-de-sac neighborhood in Sturbridge, this beautifully maintained single-family home offers comfort, space, & thoughtful updates throughout! Step inside to a fireplaced living room that flows into a formal dining room & an expansive, sun-filled family room. An eat-in kitchen w/ granite countertops provides direct access to the deck, creating an easy indoor-outdoor

    James Black Real Broker MA, LLC

    39 Hillside Dr, Sturbridge, MA 01566
  • /37

    $899,900

    $60K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 2,140 Sq Ft

    26 Cedar Lake Dr, Sturbridge, MA 01566

    DIRECT WATERFRONT LIVING ON CEDAR POND! Welcome to 26 Cedar Lake Drive, a rare opportunity to own a fully remodeled lakefront retreat on one of Sturbridge's most desirable fully recreational lake. This home offers the ultimate waterfront lifestyle with direct access to Cedar Pond and a private boat slip tucked conveniently BENEATH THE HOUSE, a unique feature that makes an effortless launching of

    Richard Stockhaus Lakefront Living Realty, LLC

    26 Cedar Lake Dr, Sturbridge, MA 01566
  • /2

    $275,000

    • Land
    • 2.36 Acres
    • $116,525 per Acre

    Lot B-6 River Rd, Sturbridge, NY 00566

    LAND AND LOCATION ! You have found it here! A MAJOR CORNER SITE at RIVER ROAD and ROUTE 15 across from Exit 2 off I-84. This 2.36 acres has 670 ft total frontage with over 300 feet on River Road and is opposite the former Hebert Candies Store (now a Dog Care facility) at 1 River Road, The sandy gravel soils are wooded and the grade runs up gently from the road. The zoning is Special Use

    Gary Griffin Sholan Realty

    Lot B-6 River Rd, Sturbridge, NY 00566
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