Vintage homes for sale & real estate in 01566, MA

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NEW 18 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in 01566, MA:
Welcome to desirable Fiske Hill in Sturbridge! This inviting 3-bedroom, 1.5-bath home offers a wonderful combination of comfort, privacy, and commuter convenience. The fireplaced living room provides a warm gathering space, while hardwood flooring adds classic appeal in select rooms. Enjoy a nice front porch for relaxing, plus a side deck overlooking the beautiful and private yard. Outdoor highlights include an above-ground pool, garden area, and lovely front-yard apple and magnolia trees. With no visible neighbors on either side, the setting offers a rare sense of privacy and peaceful enjoyment. The home also features a kitchen with stainless-steel appliances and pantry, a convenient mudro

$385,000

3 beds1.5 baths1,404 sq ft

Garden area • Front porch • Side deck

18 Fiske Hill Rd, Sturbridge, MA 01566

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in 01566, MA:
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 the beautifully landscaped backyard. The kitchen offers granite countertops, high end appliances, abundant cabinetry, a center island, and pantry, while the formal dining room and front-to-back fireplaced living room provide plenty of space for entertaining. Upstairs, the generous primary suit

$589,900

3 beds2.5 baths2,205 sq ft

Granite countertops • Hardwood floors • Large bay window

32 Mcgregory Rd, Sturbridge, MA 01566

ABOUT THIS HOME
Vintage Home for sale in 01566, MA:
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 spacious bedrooms and a full bath. At that time, the roof and windows were also replaced, and the home has seen electrical updates as well, providing added value and peace of mind. The first floor features an area where the previous owners began preparing for future improvements by removing a wall

$425,000

3 beds2 baths1,150 sq ft

Electrical updates • Serene setting • 7,405 sq ft lot

12 Fairground Rd, Sturbridge, MA 01566

ABOUT THIS HOME
Vintage Home for sale in 01566, MA:
* * Seller asking for highest & best offers: 8/18/26 by 5pm please * * 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, garden area, and a large sun porch that opens directly to the pool. The versatile floor plan includes an in-law apartment, making it ideal for multiple generations, extended guest accommodations or a fantastic work from home option. The first floor boasts an eat-in kitchen, dining room, den, and

$595,000

6 beds5.5 baths3,506 sq ft

In-law apartment • In-ground pool • Garden area

6 Newton Pl, Sturbridge, MA 01566

ABOUT THIS HOME
Vintage Home for sale in 01566, MA:
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 gleaming hardwood floors, raised-panel detailing, crown molding, delightful built-ins, exposed beams, and two wood-burning fireplaces. The spacious layout features 3 generously sized bedrooms, a bright & sunny living room, cozy den, kitchen and full bath with both a tub and separate shower. Re

$449,000

3 beds1 bath2,091 sq ft

Exposed beams • Crown molding • Built-ins

212 Charlton Rd, Sturbridge, MA 01566

Property at 6 Belanger Ave, Sturbridge, MA 01566, 3 beds, 2 baths

$500,000

3 beds2 baths1,568 sq ft

6 Belanger Ave, Sturbridge, MA 01566

Property at 10 Maple, Sturbridge, MA 01566, 4 beds, 2.5 baths

$520,000

4 beds2.5 baths2,374 sq ft

10 Maple, Sturbridge, MA 01566

Property at 30 Whittemore Rd, Sturbridge, MA 01566, 2 beds, 2 baths

$850,000

2 beds2 baths1,030 sq ft

30 Whittemore Rd, Sturbridge, MA 01566

Property at 14 Maple St, Sturbridge, MA 01566, 6 beds, 4.5 baths

$729,000

6 beds4.5 baths4,579 sq ft

14 Maple St, Sturbridge, MA 01566

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OPEN SAT, 11:30AM TO 1PM

ABOUT THIS HOME
Vintage Home for sale in 01566, MA:
Welcome to this duplex, owner-occupied for approximately 40 years. The property offers a great opportunity for an owner-occupant or investor, with the first-floor unit to be delivered vacant and a long-term second-floor tenant of 9 years currently in place at will. The first floor features hardwood floors throughout, an updated pantry, and a tiled bathroom. The second floor has a new natural gas furnace. Additional highlights include off-street parking, natural gas utilities and a neighborhood setting conveniently located near a hospital and a conservation area complete with walking and biking trails.

$335,000

6 beds2 baths2,296 sq ft

Updated pantry • Tiled bathroom • Off-street parking

48 Litchfield Ave, Southbridge, MA 01550

ABOUT THIS HOME
Vintage Home for sale in 01566, MA:
Attention! If you’re looking for a four-bedroom home, your search may be over! This property could be exactly what you need. It is perfect for a large family and, with a little care and some improvements, it could become the ideal home for you and your family for years to come. The photos are original; some images were created or enhanced using artificial intelligence solely to illustrate the property’s potential. These images may not accurately represent the home’s current condition. The home is being sold strictly “AS IS. ” The Buyer will be responsible for assuming the existing solar panel lease/contract. Buyers and Buyer’s Agents are responsible for i

$340,000

4 beds2 baths1,098 sq ft

2,178 sq ft lot • 2 parking spots • Built 1885

3 Dean St, Southbridge, MA 01550

ABOUT THIS HOME
Vintage Home for sale in 01566, MA:
Turnkey 3-unit investment opportunity in Southbridge! This well-maintained multifamily offers a mix of unit sizes: a 2-bed/1-bath basement unit (current tenant, lease through 11/30/2026, $1,499/mo), a vacant 1-bed/1-bath unit ready for immediate occupancy or owner-use ($1,600/mo market rent), and a 2-bed/1-bath unit (current tenant, lease through 5/31/2027, $1,550/mo). Total gross rent potential of approximately $4,649/month. Low operating expenses with 2025 actuals including taxes ($2,915), R & M ($665), and utilities. Ideal for an investor seeking immediate cash flow with upside from the vacant unit. Don't miss this opportunity to add a solid asset to your portfolio! Buyer to do due d

$535,000

6 beds3 baths1,240 sq ft

6,303 sq ft lot • 3 parking spots • Built 1860

165 Pleasant St, Southbridge, MA 01604

ABOUT THIS HOME
Vintage Home for sale in 01566, MA:
Welcome to this beautiful, ready-to-move-in ranch offering the convenience of single-level living! This home features 2 bedrooms, 1 full bathroom, and a functional, inviting layout. The property offers several updated features, including the siding, roof, fuel tank, and kitchen cabinets, adding value and functionality to the home. Enjoy the convenience of an attached garage and ample off-street parking. Step outside to a spacious, level backyard—perfect for summer gatherings, entertaining, gardening, or simply relaxing outdoors. A great opportunity to enjoy easy one-level living with generous outdoor space and plenty of parking. Join us for the open house this Saturday August 15th fro

$332,900

2 beds1 bath952 sq ft

Attached garage • Level backyard • Single-level living

10 Union St, Southbridge, MA 01550

ABOUT THIS HOME
Vintage Home for sale in 01566, MA:
Create your next chapter in a home with enduring character. Home has a welcoming covered front porch. Perfect place to sit & relax. Walking in your front door you are greeted by a nice living room w/ fireplace, hardwood floors, with an adjacent room - great for working from home or a playroom! Older eat in kitchen with wood cabinets. Formal dining room off the kitchen is a great size for gatherings. Upstairs you have three well portioned bedrooms with great closet space. Hardwood floors under the rugs in the 2 guest rooms upstairs. Main bedroom has hardwood floors and its own private full bathroom. 2nd floor bathroom has a large bathtub. Replacement windows. Gas Heating system - 202

$329,900

3 beds2 baths1,648 sq ft

Covered front porch • Formal dining room • Eat in kitchen

34 Woodland St, Southbridge, MA 01550

ABOUT THIS HOME
Vintage Home for sale in 01566, MA:
This 10-unit mixed use deal located right in downtown Southbridge includes four well-maintained adjacent buildings. It includes two (2) Commercial units, two (2) 3-Bedroom/1-Bathroom units, four (4) 2-Bedroom/1-Bathroom units, and two (2) Studio units with 11,714 square feet of gross living area in 19,307 square feet of gross area. All units are currently occupied. The Property is situated upon a 0.32-acre parcel and features ample off-street parking for residential tenants. The majority of tenants are TAW and below market offering immediate upside. Tenants are responsible for a mix of gas & electric powered heat and separately metered electricity. The Landlord is just responsible for

$1,100,000

16 beds8 baths11,714 sq ft

Off street parking • Strong access • 0.32 acre lot

48-62 Central St, Southbridge, MA 01550

Property at 16 Water St, Southbridge, MA 01550, 3 beds, 1.5 baths

$259,900

3 beds1.5 baths1,242 sq ft

16 Water St, Southbridge, MA 01550

Property at 48 Union St, Southbridge, MA 01550, 9 beds, 4 baths

$620,000

9 beds4 baths4,659 sq ft

48 Union St, Southbridge, MA 01550

Property at 266 Brookfield Rd, Charlton, MA 01507, 3 beds, 1 bath

$350,000

3 beds1 bath2,160 sq ft

266 Brookfield Rd, Charlton, MA 01507

Property at 26 Harding Ct, Southbridge, MA 01550, 6 beds, 3 baths

$425,000

6 beds3 baths2,283 sq ft

26 Harding Ct, Southbridge, MA 01550

Property at 90 Sayles St, Southbridge, MA 01550, 12 beds, 6 baths

$849,900

12 beds6 baths9,000 sq ft

90 Sayles St, Southbridge, MA 01550

Property at 172 Stone Rd, East Brookfield, MA 01515, 3 beds, 2 baths

$549,000

3 beds2 baths1,841 sq ft

172 Stone Rd, East Brookfield, MA 01515

Property at 37 Oakes Ave, Southbridge, MA 01550, 7 beds, 2 baths

$524,900

7 beds2 baths2,319 sq ft

37 Oakes Ave, Southbridge, MA 01550

Property at 125 Chapin St, Southbridge, MA 01550, 4 beds, 2 baths

$410,000

4 beds2 baths2,473 sq ft

125 Chapin St, Southbridge, MA 01550

Property at 82 Hartwell St, Southbridge, MA 01550, 3 beds, 1.5 baths

$424,900

3 beds1.5 baths1,884 sq ft

82 Hartwell St, Southbridge, MA 01550

Property at 17-19 Coolidge Ave, Southbridge, MA 01550, 6 beds, 2 baths

$429,900

6 beds2 baths2,576 sq ft

17-19 Coolidge Ave, Southbridge, MA 01550

Property at 4 Essex St, Holland, MA 01521, 2 beds, 1 bath

$250,000

2 beds1 bath1,428 sq ft

4 Essex St, Holland, MA 01521

Property at 183 West Sturbridge Rd, East Brookfield, MA 01515, 1 bed, 1 bath

$309,900

1 bed1 bath1,044 sq ft

183 West Sturbridge Rd, East Brookfield, MA 01515

Property at 33 Union St, Southbridge, MA 01550, 8 beds, 4 baths

$650,000

8 beds4 baths2,592 sq ft

33 Union St, Southbridge, MA 01550

Property at 59 Cross St, Southbridge, MA 01550, 10 beds, 4 baths

$680,000

10 beds4 baths3,504 sq ft

59 Cross St, Southbridge, MA 01550

Vintage Homes for Sale in 01566

There are currently 9 vintage homes for sale in 01566 at a median listing price of $535K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in 01566 stay on the market for 45 days. This map is refreshed with the newest listings in 01566 every 15 minutes.

In the past month, 14 homes have been sold in 01566. In addition to houses in 01566, there was also 1 condo, 4 townhouses, and 1 multi-family unit for sale in 01566 last month. Find your dream home in 01566 using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in 01566 are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in 01566. If you're looking to sell your home in the 01566 area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in 01566 with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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