Sturbridge, MA Homes

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  /37

  $595,000

  Sold Dec 12, 2025

  10 Orchard Rd, Sturbridge, MA 01566

  • 4 Beds
  • 3.5 Baths
  • 2,388 Sq Ft
  • Built 1988

  Last Sold Summary

  • $249/SF
  • 5 Days On Market

  Current Estimated Value $598,376

  Last Listing Agent Lexi O'Brien RE/MAX Prof Associates

  10 Orchard Rd, Sturbridge, MA 01566
• 

  

  

  /18

  Not Listed For Sale

  45 Park Ave, Sturbridge, MA 01566

  • 2 Beds
  • 1.5 Baths
  • 924 Sq Ft
  • Built 1984

  45 Park Ave, Sturbridge, MA 01566

  Last Sold Summary

  • 27 Days On Market

  Last Listing Agent Kris Lippi Get Listed Realty, LLC
• 

  

  

  /37

  $490,000

  $10K PRICE DROP

  • 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

  

  Carrie Abysalh

  RE/MAX Prof Associates

  6 Belanger Ave, Sturbridge, MA 01566
• 

  

  

  /42

  $565,000

  Sold Jun 26, 2026

  51 Clark Rd, Fiskdale, MA 01518

  • 3 Beds
  • 2.5 Baths
  • 2,698 Sq Ft
  • Built 1994

  Last Sold Summary

  • 7% Above List Price
  • $209/SF
  • 8 Days On Market

  Current Estimated Value $532,216

  Last Listing Agent Lisa Matondi-Merow RE/MAX Prof Associates

  51 Clark Rd, Fiskdale, MA 01518
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  /39

  Not Listed For Sale

  223 Park Cir, Sturbridge, MA 01566

  • 2 Beds
  • 1.5 Baths
  • 980 Sq Ft
  • Built 1987

  223 Park Cir, Sturbridge, MA 01566

  Last Sold Summary

  • 20 Days On Market

  Last Listing Agent Moira McGrath Keller Williams Pinnacle Central
• 

  

  /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

  

  Laurie Casey

  Leading Edge Real Estate

  12 Carey Rd, Sturbridge, MA 01566
• 

  

  /41

  $525,000

  Sold Sep 30, 2025

  64 Stallion Hill Rd, Fiskdale, MA 01518

  • 3 Beds
  • 2 Baths
  • 1,646 Sq Ft
  • Built 1969

  Last Sold Summary

  • 5% Above List Price
  • $319/SF
  • 5 Days On Market

  Current Estimated Value $524,578

  Last Listing Agent Stephanie Lachapelle Compass

  64 Stallion Hill Rd, Fiskdale, MA 01518
• 

  

  /3

  Est $165,224

  Not Listed For Sale

  59 Streeter Rd, Sturbridge, MA 01518

  59 Streeter Rd, Sturbridge, MA 01518

  Last Sold Summary

  • 66 Days On Market

  Last Listing Agent Jean Sullivan Sullivan & Company Real Estate, Inc.
• 

  

  /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

  

  Justin Stelmok

  J.W. Management & Sales, Inc.

  21 Pinrock Dr, Sturbridge, MA 01566
• 

  

  /42

  $540,000

  Sold Sep 12, 2025

  157 Podunk Rd, Sturbridge, MA 01566

  • 4 Beds
  • 2.5 Baths
  • 2,230 Sq Ft
  • Built 1984

  Last Sold Summary

  • 8% Below List Price
  • $242/SF
  • 20 Days On Market

  Current Estimated Value $574,323

  Last Listing Agent Carrie Abysalh RE/MAX Prof Associates

  157 Podunk Rd, Sturbridge, MA 01566
• 

  

  /39

  Est $673,865

  Not Listed For Sale

  25 Woodside Cir, Sturbridge, MA 01566

  • 3 Beds
  • 2.5 Baths
  • 2,896 Sq Ft
  • Built 1991

  25 Woodside Cir, Sturbridge, MA 01566

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Sue Gordon Castinetti Realty Group
• 

  

  /42

  $619,900

  • 3 Beds
  • 2.5 Baths
  • 2,413 Sq Ft

  55 S Shore Dr, Sturbridge, MA 01566

  Your own private oasis in beautiful Sturbridge with deeded water access to South Pond! Set on 1.44 professionally landscaped acres, this inviting Colonial offers privacy, style & an incredible indoor/outdoor lifestyle. The backyard is a true retreat with an in-ground pool, hot tub, gorgeous patio, back deck & an amazing pool shed with its own bar and living room, perfect for entertaining! Inside,

  Michelle Terry Team eXp Realty LLC

  55 S Shore Dr, Sturbridge, MA 01566
• 

  

  /40

  $600,000

  Sold Oct 16, 2025

  18 South Rd, Sturbridge, MA 01566

  • 3 Beds
  • 2.5 Baths
  • 2,404 Sq Ft
  • Built 2003

  Last Sold Summary

  • 15% Above List Price
  • $250/SF
  • 2 Days On Market

  Current Estimated Value $603,939

  Last Listing Agent Zoe Theocles Landmark, REALTORS®

  18 South Rd, Sturbridge, MA 01566
• 

  

  /39

  Est $667,385

  Not Listed For Sale

  5 Woodside Cir, Sturbridge, MA 01566

  • 4 Beds
  • 2.5 Baths
  • 2,816 Sq Ft
  • Built 1986

  5 Woodside Cir, Sturbridge, MA 01566

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Stephanie Lachapelle Compass
• 

  

  /42

  $589,900

  Pending

  • 3 Beds
  • 2.5 Baths
  • 2,205 Sq Ft

  32 Mcgregory Rd, Sturbridge, MA 01566

  Welcome to 32 McGregory Road, ideally situated in one of Sturbridge’s popular established neighborhoods! This spacious 3-bedroom, 2.5-bath Colonial offers over 2,200 sq. ft. of living space and a wonderful blend of character, comfort, and functionality. The inviting family room features a beamed cathedral ceiling, hardwood floors, built-ins, a large bay window, and access to the deck overlooking

  Michelle Terry Team eXp Realty LLC

  32 Mcgregory Rd, Sturbridge, MA 01566
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  /36

  $767,000

  Sold Oct 29, 2025

  20 Audubon Way, Sturbridge, MA 01566

  • 4 Beds
  • 2.5 Baths
  • 2,664 Sq Ft
  • Built 2004

  Last Sold Summary

  • $288/SF
  • 6 Days On Market

  Current Estimated Value $779,576

  Last Listing Agent Stephanie Lachapelle Compass

  20 Audubon Way, Sturbridge, MA 01566
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  /38

  Est $671,992

  Not Listed For Sale

  28 Woodlawn Dr, Sturbridge, MA 01566

  • 4 Beds
  • 3 Baths
  • 2,812 Sq Ft
  • Built 1985

  28 Woodlawn Dr, Sturbridge, MA 01566

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Stephanie Lachapelle Compass
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  /37

  $479,900

  Pending

  • 3 Beds
  • 2 Baths
  • 2,209 Sq Ft

  27 Hillside Dr, Sturbridge, MA 01566

  Pool Opening Soon! Welcome home to this spacious 3 BR 2 BA Home located in the desirable Hillside Drive Neighborhood! Situated on a quiet cul-de-sac street, this home offers a convenient location for commuters while being just minutes to shopping, dining and everyday amenities. The main living level features all hardwood flooring and an inviting open-concept layout, including the FPLD Living Rm,

  Lorraine Herbert RE/MAX Prof Associates

  27 Hillside Dr, Sturbridge, MA 01566
• 

  

  /16

  $490,000

  Sold Aug 11, 2026

  135 Walker Pond Rd, Sturbridge, MA 01566

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft
  • Built 1968

  Last Sold Summary

  • 2% Below List Price
  • $272/SF
  • 44 Days On Market

  Current Estimated Value $494,406

  Last Listing Agent Derek Greene The Greene Realty Group

  135 Walker Pond Rd, Sturbridge, MA 01566
• 

  

  /40

  Est $693,203

  Not Listed For Sale

  18 Willard Rd, Sturbridge, MA 01566

  • 8 Beds
  • 5.5 Baths
  • 5,732 Sq Ft
  • Built 1965

  18 Willard Rd, Sturbridge, MA 01566

  Last Sold Summary

  • 12 Days On Market

  Last Listing Agent David White OwnerEntry.com
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  /34

  $595,000

  $54K PRICE DROP Pending

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

  6 Newton Place, Sturbridge, MA 01566

  *Kick-out Clause in place - seller still marketing property & accepting offers. 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 5½ bathrooms. The private 1.14-acre lot is a backyard retreat featuring an in-ground pool, greenhouse,

  Julie Horrigan RE/MAX Prof Associates

  6 Newton Place, Sturbridge, MA 01566
• 

  

  /19

  $172,500

  Sold Dec 01, 2025

  606 Skyline Dr Unit 606, Sturbridge, MA 01566

  • 2 Beds
  • 2 Baths
  • 1,000 Sq Ft
  • Built 2012

  Last Sold Summary

  • 14% Below List Price
  • $172/SF
  • 32 Days On Market

  Last Listing Agent Carly Cowher Sullivan & Company Real Estate, Inc.

  606 Skyline Dr Unit 606, Sturbridge, MA 01566
• 

  

  /34

  Est $617,785

  Not Listed For Sale

  34 Willard Rd, Sturbridge, MA 01566

  • 4 Beds
  • 2.5 Baths
  • 2,005 Sq Ft
  • Built 1986

  34 Willard Rd, Sturbridge, MA 01566

  Last Sold Summary

  • 11 Days On Market

  Last Listing Agent Brooke Coughlin Lamacchia Realty, Inc.
• 

  

  /42

  $700,000

  • 4 Beds
  • 3.5 Baths
  • 3,206 Sq Ft

  61 Breakneck Rd, Sturbridge, MA 01566

  Welcome home to this beautiful 3,200 sq. ft. Colonial set on over 4 acres, offering a rare combination of space, privacy, and character. Thoughtfully updated while retaining its classic charm, this exceptional property features updated kitchens and bathrooms, beautiful hardwood floors, custom built-ins, and inviting spaces designed for both everyday living and entertaining.The main home offers 3

  Neilsen Team - Livian The Neilsen Team

  61 Breakneck Rd, Sturbridge, MA 01566
• 

  

  /26

  $499,900

  Sold Jun 08, 2026

  224 Podunk Rd, Sturbridge, MA 01566

  • 3 Beds
  • 1.5 Baths
  • 2,132 Sq Ft
  • Built 1985

  Last Sold Summary

  • $234/SF
  • 142 Days On Market

  Current Estimated Value $501,507

  Last Listing Agent Tracey Fiorelli Janice Mitchell R.E., Inc

  224 Podunk Rd, Sturbridge, MA 01566
• 

  

  /42

  Est $619,774

  Not Listed For Sale

  98 Westwood Dr, Sturbridge, MA 01566

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft
  • Built 1965

  98 Westwood Dr, Sturbridge, MA 01566

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Paula Snow Media Realty Group Inc.
• 

  

  /42

  $435,000

  $60K PRICE DROP Pending

  • 4 Beds
  • 2 Baths
  • 2,512 Sq Ft

  11 Whittemore Rd, Sturbridge, MA 01566

  Motivated sellers, Maine bound — and $10K at closing, spend it how you wish. Some houses are built. This one was made—two centuries of seasons, life that keeps pumpkin pine floors gleaming and fanlight windows catching the light. Set in-town on 2.4 beautiful corner acres where stone walls trace the land, wooded privacy on one side, a barn and chicken coop beyond the garden—this large four-bedroom

  Pamrose Eden-Cox Coldwell Banker Community REALTORS®

  11 Whittemore Rd, Sturbridge, MA 01566
• 

  

  /28

  $224,298

  Sold Nov 14, 2025

  5 Fairview Park Rd Unit A10, Sturbridge, MA 01566

  • 2 Beds
  • 1 Bath
  • 800 Sq Ft
  • Built 1975

  Last Sold Summary

  • 2% Above List Price
  • $280/SF
  • 4 Days On Market

  Current Estimated Value $225,171

  Last Listing Agent Jennifer McKinstry Byrnes Real Estate Group LLC

  5 Fairview Park Rd Unit A10, Sturbridge, MA 01566
• 

  

  /41

  Est $341,617

  Not Listed For Sale

  92 Westwood Dr, Sturbridge, MA 01566

  • 2 Beds
  • 1 Bath
  • 640 Sq Ft
  • Built 1967

  92 Westwood Dr, Sturbridge, MA 01566

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Amy Gerrish RE/MAX Prof Associates
• 

  

  /21

  $179,900

  $20K PRICE DROP

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

  117 Vista Ln, Sturbridge, MA 01566

  PRICE REDUCED!!! Motivated sellers! DOUBLE WIDE! BRING your offers! This home is situated on a quiet dead-end street private, wooded, corner lot. This open-concept lay-out home features a beautiful kitchen packed with cabinets and pantry flowing seamlessly into the dining room & living areas, creating the perfect space for everyday living & entertaining! Large primary bedroom includes a walk-in

  Penny Cote LAER Realty Partners

  117 Vista Ln, Sturbridge, MA 01566
• 

  

  /40

  $487,500

  Sold Nov 21, 2025

  7 Orchard Rd, Sturbridge, MA 01566

  • 3 Beds
  • 2.5 Baths
  • 2,607 Sq Ft
  • Built 1984

  Last Sold Summary

  • 3% Above List Price
  • $187/SF
  • 4 Days On Market

  Current Estimated Value $545,141

  Last Listing Agent Noelle Merle Hometown National Realty Inc.

  7 Orchard Rd, Sturbridge, MA 01566
• 

  

  /23

  Est $438,067

  Not Listed For Sale

  114 Westwood Dr, Sturbridge, MA 01566

  • 2 Beds
  • 1 Bath
  • 790 Sq Ft
  • Built 1965

  114 Westwood Dr, Sturbridge, MA 01566

  Last Sold Summary

  • 115 Days On Market

  Last Listing Agent Lifeline Realty Team RE/MAX Prof Associates
• 

  

  /40

  $989,900

  Pending

  • 2 Beds
  • 2 Baths
  • 2,408 Sq Ft

  104 S Shore Dr, Sturbridge, MA 01566

  Private waterfront retreat nestled in a peaceful cove on Lake Quacumquasit (South Pond). This exceptional residence offers beautiful water views & refined, year-round living. A sun-filled 3-season room showcasing expansive windows capturing the natural surroundings, while the covered patio, outdoor shower, firepit, and private dock create the perfect lakeside setting. The open-concept kitchen

  Renee Prunier Lamacchia Realty, Inc.

  104 S Shore Dr, Sturbridge, MA 01566
• 

  

  /25

  $130,500

  Sold Mar 26, 2026

  43 Park Ave, Sturbridge, MA 01566

  • 2 Beds
  • 1.5 Baths
  • 1,124 Sq Ft
  • Built 1982

  Last Sold Summary

  • 10% Below List Price
  • $116/SF
  • 43 Days On Market

  Last Listing Agent James Black Real Broker MA, LLC

  43 Park Ave, Sturbridge, MA 01566
• 

  

  /42

  Est $836,826

  Not Listed For Sale

  112 Westwood Dr, Sturbridge, MA 01566

  • 3 Beds
  • 2.5 Baths
  • 2,244 Sq Ft
  • Built 1981

  112 Westwood Dr, Sturbridge, MA 01566

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Lifeline Realty Team RE/MAX Prof Associates
• 

  

  /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
• 

  

  /21

  $385,000

  Sold Feb 10, 2026

  200 Main St, Sturbridge, MA 01566

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft
  • Built 1965

  Last Sold Summary

  • 4% Below List Price
  • $267/SF
  • 81 Days On Market

  Current Estimated Value $390,451

  Last Listing Agent Lora Savage Century 21 XSELL REALTY

  200 Main St, Sturbridge, MA 01566
• 

  

  /39

  Est $636,006

  Not Listed For Sale

  5 Wells Park Rd, Sturbridge, MA 01566

  • 4 Beds
  • 2 Baths
  • 2,493 Sq Ft
  • Built 1993

  5 Wells Park Rd, Sturbridge, MA 01566

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Ann Marie Sorensen ERA Key Realty Services- Auburn
• 

  

  /37

  $499,000

  $28K PRICE DROP Pending

  • 5 Beds
  • 2 Baths
  • 3,269 Sq Ft

  16 Summit Ave, Fiskdale, MA 01518

  Don't miss this charming and spacious colonial home with the most idyllic outdoor space. This 5 bed 2 bath home boasts over 3,200 sq ft, plus a massive detached garage with heat and 2nd story. Enter to find an open concept kitchen and dining area with a wood stove and pantry. The dining room with beautiful wall trim details opens to the coffered ceiling family room with a fireplace and den. There

  Stephanie Lachapelle Compass

  16 Summit Ave, Fiskdale, MA 01518
• 

  

  /18

  $420,000

  Sold Aug 10, 2026

  76 Hall Rd, Sturbridge, MA 01566

  • 3 Beds
  • 1 Bath
  • 1,508 Sq Ft
  • Built 1965

  Last Sold Summary

  • 6% Below List Price
  • $279/SF
  • 61 Days On Market

  Current Estimated Value $426,349

  Last Listing Agent Elaine Phifer Olde Village Realty

  76 Hall Rd, Sturbridge, MA 01566

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