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926 Old Turnpike Road, Oakham
$975,000
73484213 MLS
This amazing Commercial compound consists of 3 buildings on 7 acres of land. The 2368SF Cape style home offers 3 bedrooms, 2 full baths, a heated breezeway into a sun room overlooking the beautifully landscaped yard with private 24x42 updated in ground pool. The partially finished basement has updated heating and an office. The property also has a heated 2 car garage. The 1638 SF Commercial office building offers 2 floors of rent-able space and has a kitchenette and a half bath on each floor with expansion possibilities. The 3rd building is a 1440 SF single family home set up. The home features 4 rooms, 2 bedrooms and 1 bath in an open floor plan with expansion possibilities. Property has been well maintained, one family ownership. Perfect "Country" 3 family!

926 Old Turnpike Road, Oakham
926 Old Turnpike Road, Oakham
$975,000
5 Beds ⋅ 6 Baths ⋅ 73484212 MLS
This amazing compound consists of 3 buildings on 7 acres of land. The 2368SF Cape style home offers 3 bedrooms, 2 full baths, a heated breezeway into a sun room overlooking the beautifully landscaped yard with private 24x42 updated in ground pool. The partially finished basement has updated heating and an office. The property also has a heated 2 car garage. The 1638 SF Commercial office building offers 2 floors of rent-able space and has a kitchenette and a half bath on each floor with expansion possibilities. The 3rd building is a 1440 SF single family home set up. The home features 4 rooms, 2 bedrooms and 1 bath in an open floor plan with expansion possibilities. Property has been well maintained, one family ownership. Perfect "Country" 3 family!

926 Old Turnpike Road, Oakham
775 East Hill Road, Oakham
$760,000
4 Beds ⋅ 3 Baths ⋅ 73529539 MLS
Escape the hustle and bustle and discover your own private 14-acre retreat. Whether casting a line, enjoying a boat ride, or simply taking in the peaceful surroundings, this property offers relaxation and recreation right at home. A soaring vaulted entry welcomes you inside. The updated kitchen features quartz countertops, SS appliances, teak hardwood fls, and opens to a porcelain-tiled patio perfect for entertaining. The inviting great room features a stunning floor-to-ceiling stone fireplace, while the dining room offers plenty of space for gatherings. The primary suite includes a full bath, walk-in closet, double closets, and adjoining laundry area. Upstairs are 3 additional bedrooms, loft-style bonus area, and full bath. Walk-out basement w/workshop and supplemental coal furnace. Metal roof approx. 8 yrs. House resided approx. 5 yrs ago.

775 East Hill Road, Oakham
1380 North Brookfield Rd, Oakham
$740,000
4 Beds ⋅ 3 Baths ⋅ 73468639 MLS
Incredible opportunity to live on your own Christmas Tree Farm in Central Mass! Custom built, one owner home offering a HUGE first floor layout allowing for spacious single level living w/2 room primary suite w/deck access via sliders, including a full bath w/walk in shower. Gleaming hardwood floors throughout your living room & dining area w/sliders to your 2 level back deck, cabinet packed eat-in kitchen w/granite counters, center island w/pull outs, plus breakfast bar seating for 4+. Another bedroom, 2nd full bath, laundry room and garage access (3 bay doors) finish off the main level. Upstairs you'll find full bath #3, bedrooms 3 & 4, plus a MASSIVE walk in attic w/loads of potential to finish and add more living space. The full WO basement (unfinished) also offers unlimited potential to finish - future workshop/media room/office/exercise space? Wood stove, 2 oil tanks, private water & septic - all this on just over 5 acres - just 3 minutes to Dean Lake & Pine Acres Campground!

1380 North Brookfield Rd, Oakham
300 Stone Rd, Oakham
$700,000
4 Beds ⋅ 2 Baths ⋅ 73506126 MLS
Highest and Best offers due Wednesday, May 13th at 5pm. Step back in time with this historic home dating back to the 1700s/1800s. Set on two combined lots totaling over 51 acres, the property offers a mix of open, cleared land and wooded areas, all with sweeping views and exceptional privacy. The home features 4 bedrooms and 2 full baths—one on each level—while preserving its timeless charm with period details throughout. A warm, inviting country kitchen serves as the heart of the home, complemented by a welcoming dining room perfect for gatherings and a spacious living room complete with a wet bar for entertaining. The majority of the land is cleared and thoughtfully divided into rolling pastures, currently home to Romney sheep. With its scenic landscape, breathtaking views, and serene seclusion, this is a rare opportunity to own a truly special piece of history in a peaceful, pastoral setting. Come see for yourself and set up a tour today!

300 Stone Rd, Oakham
70 Skyline Dr, Oakham
$645,000
3 Beds ⋅ 3 Baths ⋅ 73509436 MLS
Welcome to this beautifully maintained 2,300 square-foot Colonial, built in 2003 and nestled on nearly 4 private acres in the highly desirable Longview Estates in Oakham. This inviting home features a classic farmer’s porch, perfect for relaxing and enjoying the peaceful surroundings. Inside, you’ll find a spacious layout highlighted by a large family room ideal for gatherings and everyday living. The home offers generous natural light, comfortable living spaces, and thoughtful design throughout. Step outside to your own private retreat, complete with a deck overlooking the backyard and an above-ground pool—perfect for summer entertaining or quiet evenings at home. The expansive lot provides both privacy and room to enjoy the outdoors. Additional features include a two-car garage and a prime location within a sought-after neighborhood known for its scenic beauty and tranquility. This is a rare opportunity to enjoy space, comfort, and community all in one exceptional property.

70 Skyline Dr, Oakham
157 Robinson Rd, Oakham
$640,000
3 Beds ⋅ 3 Baths ⋅ 73519458 MLS
Your own waterfront retreat! 19.5 acres of tranquility on Brooks Pond, complete with your very own Island! Perfectly set overlooking the pond with a large deck and lower level screened porch. Bright and Sunny! The main level includes an open concept living room with woodstove, dining room and kitchen with breakfast Nook, 1st floor bedroom! Upstairs you will find the primary suite with dressing area, large closets, and ensuite full bath. Relax in the calm of your own library overlooking the main floor, 3rd bedroom and additional full bath. Oversized windows throughout! Lower level family room and plenty of storage! ADU potential in the separate building steps from the main home or a Fantastic home office! This is a must see!

157 Robinson Rd, Oakham
283 Adams Road, Oakham
$595,000
4 Beds ⋅ 3 Baths ⋅ 73552430 MLS
Beautifully Renovated Colonial on 8.35 Acres! Enjoy the best of country living in this 4-bedroom, 2½-bath Colonial featuring modern updates and timeless charm. Set on 8.35 private acres, this home offers expansive outdoor space with nearby hiking and biking trails and golfing just minutes away. The remodeled farmer’s porch welcomes you home, while the large covered porch off the kitchen is perfect for entertaining or relaxing in the shade. Inside, you’ll find bright, open living areas all recently updated, and thoughtful finishes throughout. A rare opportunity to own a move-in-ready home surrounded by nature and tranquility in desirable Oakham, MA!

283 Adams Road, Oakham
275 Crawford Rd, Oakham
$585,000
2 Beds ⋅ 2 Baths ⋅ 73488578 MLS
This newly constructed 2022 home combines modern, energy-efficient living with privacy and peaceful surroundings, offering a comfortable and versatile layout for any lifestyle. The country kitchen features stainless steel appliances, while custom molding and attention to detail throughout showcase quality and style. Enjoy a 2-car garage, a farm-style porch and a deck overlooking the backyard—perfect for entertaining or relaxing. The lower level is rough-plumbed for a third bathroom and offers flexible space for additional living or recreational use. With a 4-bedroom septic system, there’s room for future expansion if needed. Fully equipped, move-in ready and thoughtfully designed, this home combines style, function and privacy—offering endless possibilities for peaceful living and enjoyment.

275 Crawford Rd, Oakham
1109 New Braintree Rd, Oakham
$575,000
4 Beds ⋅ 3 Baths ⋅ 73450621 MLS
BEST AND FINAL OFFERS DUE 11/17 AT 5:00 PM NO ESCALATION CLAUSES. Beautiful 4-bedroom, 2.5-bath Colonial offers comfort, charm, and thoughtful updates throughout. The updated eat-in kitchen features granite countertops, stainless steel appliances, and wood (SYP) floors that flow into a formal dining room and spacious living area—perfect for entertaining. The first floor also includes a convenient half bath and laundry room. Relax on the inviting 4-season porch or step out to the brick patio overlooking a peaceful, private yard. Upstairs, the primary en suite offers a walk-in closet and renovated bath. Three additional bedrooms and a full bath complete the second floor. The attached 2 car garage provides ample loft storage for convenience. Includes an Econoburn wood burning boiler that is integrated into the hot water system to help with heating bills! Brand new septic tank and D-Box (2025). Main roof 2013; porch/garage roof 2025.

1109 New Braintree Rd, Oakham
356 Hunt Rd, Oakham
$575,000
5 Beds ⋅ 4 Baths ⋅ 73310802 MLS
Timeless charm meets modern luxury in this quintessential New England farmhouse set on a serene 3.27-acre lot with an attached 3-stall barn. This beautifully remodeled home features 5 spacious bedrooms, including a primary suite with its own private deck, en suite bath and walk-in closet. The main level offers a flowing floor plan anchored by a large living room, dining area with a cozy wood stove and 1.5 bathrooms. The stunning kitchen boasts stainless steel appliances, granite countertops, a walk-in pantry and sliders that open to an expansive back deck with views of the stunning landscape. The full in-law suite provides an opportunity for multi-generational living or rental income. 1st-floor bonus room connects directly to the attached barn making it the perfect space for an equestrian's tack room. The property also offers direct access to miles of scenic trails for horseback riding, hiking and ATVs. This is the perfect home for those looking for a true homestead!

356 Hunt Rd, Oakham
171 Farm Pond Rd, Oakham
$570,000
3 Beds ⋅ 3 Baths ⋅ 73541557 MLS
Designed w/entertaining in mind, this home offers an open-concept fl plan & private 3-acre setting. The 1st floor features a stunning 33-ft country kitchen w/ss appliances, quartz countertops, large walk-in pantry, & beautiful Brazilian cherry flooring. The kitchen flows seamlessly into the 26-ft front-to-back living/family rm, highlighted by a raised-hearth pellet stove, & formal dining rm adorned w/custom moldings. Sliding doors provide easy access to rear deck, perfect for indoor-outdoor gatherings. Upstairs, the generous primary suite includes a walk-in closet & en-suite bath w/soak tub & separate shower. 2 additional bedrooms, another full bath with laundry complete the level. The finished lower level offers additional heated living and entertainment space, while the heated two-car garage provides year-round comfort/convenience. For equestrian or hobby farmers, the property features a two-stall barn w/water and electric w/2 paddocks & ample room for horses, goats, cows or more

171 Farm Pond Rd, Oakham
109 Rutherford Rd, Oakham
$565,000
3 Beds ⋅ 3 Baths ⋅ 73569700 MLS
**OFFER DEADLINE: Friday 09/04/2026 at 6:00 PM**Some homes are about the house. This one is about the life that comes with it. Across 8.33 acres in Oakham, open fields are nestled among beautiful mixed deciduous woodland of maple, oak, birch and ash. Fenced green fields offer room for horseback riding, while paddocks and fenced areas give horses space to roam. The barn is ready for the rhythm of everyday horse life with three stalls, a hay loft, a convenient feed room, and workshop, complemented by a detached two-bay garage/outbuilding with sliding barn-style doors. Three pear trees and a greenhouse add to the homestead possibilities, while wooded acreage and a private pond tucked out back give you even more to explore. Three wood stoves and a newly installed medium-sized outdoor wood boiler offer the ability to heat the home and hot water using the plentiful hardwood on the property. At the center of it all, the three-bedroom Cape is full of country character with hardwood floors throughout, exposed brick, built-ins and a farmhouse-inspired kitchen. A covered porch and sprawling deck create plenty of space to slow down and take in the setting. Bordered on three sides by Massachusetts Wildlife Management Area, the property also offers direct trail access through a gate at the back corner. Whether your dream is horses at home, gardens growing, animals to care for, or simply more land and freedom, this is a place where that life can take shape!

109 Rutherford Rd, Oakham
720 East Hill Road, Oakham
$545,000
3 Beds ⋅ 3 Baths ⋅ 73528210 MLS
Set back from the street on an expansive 3-acre lot, this private Oakham retreat is the one you’ve been searching for. Inside this beautifully designed 3-bedroom, 2.5-bathroom Colonial, a sun-drenched living room welcomes you with an abundance of natural light. The heart of the home is the spacious kitchen, complete with stainless steel appliances, a center island, and a casual dining area featuring slider access to a massive back deck. A formal dining room offers the perfect space for special gatherings, while a convenient half bath completes the main level. Upstairs, you will find three generous bedrooms, including a primary with a private en-suite bathroom and dual vanities, alongside a full hallway bath and an incredibly convenient second-floor laundry room. The backyard is a true outdoor oasis, where the oversized deck overlooks a massive yard that includes a fenced-in area - offering a peaceful countryside escape with all the space and privacy you've been dreaming of!

720 East Hill Road, Oakham
49 Bullard Rd, Oakham
$540,000
4 Beds ⋅ 3 Baths ⋅ 73510919 MLS
A rare opportunity to live in one of the oldest established neighborhoods in beautiful Oakham Massachusetts. A commuters dream being just outside of the craziness of the Worcester suburban market but only a 3 minute drive further down Rt 122 from Worcester and all the major highways. Well maintained and tastefully thought out Cape style home situated on over 3 acres of manicured lawn that were once home to annual garden parties.Home features an open concept kitchen, living and dining room with beautiful hardwood flooring and tile. Exterior access of kitchen to deck overlooking HUGE private back yard. First floor main bedroom with handicap accessible shower makes for easy one level living. First floor also features an additional bedroom / office with half bath and 1st floor laundry. Second floor features 2 large bedrooms and a full bathroom. Potential to finish walkout basement if you want the extra space! Home also features a 2 car garage along with additional outbuildings for storage!

49 Bullard Rd, Oakham
2266 Old Turnpike Rd, Oakham
$510,000
3 Beds ⋅ 3 Baths ⋅ 73507103 MLS
Discover the allure of 2266 Old Turnpike Rd, a captivating single-family residence built in 2002, offering 1724 square feet of thoughtfully designed living space in Oakham. This property presents an opportunity for a lifestyle marked by comfort and spacious surroundings. The three bedrooms provide comfortable and private retreats within the home. With two full bathrooms and one half bathroom, convenience and functionality are seamlessly integrated for daily living. The property includes a two-car garage, offering practical storage solutions and secure parking. Encompassing a generous lot size of 218,671 square feet, this residence provides ample outdoor space for a variety of pursuits and offers a sense of expansive privacy. To truly appreciate the potential of this Oakham property, we invite you to schedule a private viewing.

2266 Old Turnpike Rd, Oakham
116 Spencer Rd, Oakham
$470,000
3 Beds ⋅ 2 Baths ⋅ 73468274 MLS
MOTIVATED SELLERS! Enjoy country living while still having quick access to major routes! This property has so much to offer. There are 3 bedrooms & 2 full bathrooms on the main level as well as an additional bedroom/office space on the lower level with a 2nd living room & the space to add a kitchenette to create an in-law/teen suite. Multiple heating options include elec. baseboards, wood stove, & brand new pellet stove. The solar panels are owned & fully cover the electric bill every month--a HUGE bonus with the recent rate increases! Newer metal roof, newly paved driveway, new shed with heat & electric, large barn with a new metal roof & fenced lot, all set for animals if you are looking for a farm/horse property. Current owners have had horses, cows, goats, & alpacas. The fencing would be conducive to smaller animals as well and a driveway that wraps around the barn makes trailering simple! Enjoy the 3 1/2 private acres of land in such a convenient location with LOW property taxes!

116 Spencer Rd, Oakham
103 Barre Rd, Oakham
$434,900
4 Beds ⋅ 2 Baths ⋅ 73446460 MLS
Wonderful 6-room Cape-style home located in desirable Oakham. This home features an eat-in kitchen, a living room with a gas cast iron stove, four bedrooms, two full baths, a basement, and a two-car detached garage. Situated on 2.3 acres, the property offers ample space for a fire pit or garden and is framed by lovely trees. Recent updates include new plank vinyl flooring throughout the home, new stainless steel kitchen appliances, and a newly black-topped driveway. The property is just 30 minutes from Worcester, ready for immediate occupancy, and available for a quick close.

103 Barre Rd, Oakham
49 Oak Lane, Oakham
$400,000
2 Beds ⋅ 2 Baths ⋅ 73439536 MLS
Waterfront Retreat on Dean Pond - Southern Exposure– 130 feet of PRIVATE water frontage, just 15 miles from Worcester! This home offers the perfect year-round escape for boating, kayaking, and fishing enthusiasts. With Title 5 in hand, the property is ready for immediate enjoyment. The open floor plan features Kitchen with Dining Area and spacious Living Room with stunning Water Views. Hardwood floors and an original stone fireplace with pellet stove add charm and warmth. The first floor includes a bedroom with pine finishes, a full bath with laundry, and walk-in storage. Upstairs, the private main suite boasts a cathedral ceiling, 3-season sitting room with more Water Views, a jet tub bath, and a walk-in closet. Additional perks include a 2-bay carport and a screened porch for outdoor relaxation. Start planning your waterfront adventures today—this home offers the perfect blend of comfort and nature. Welcome home!

49 Oak Lane, Oakham
357 Barre Rd, Oakham
$370,000
3 Beds ⋅ 2 Baths ⋅ 73542913 MLS
Motivated seller - MAKE AN OFFER! Charming Colonial set on a private, wooded lot offering a peaceful country setting. This 3-bedroom home features a welcoming farmer’s porch and a warm, functional interior. The kitchen offers ample cabinetry and a convenient breakfast bar, opening nicely to the dining area. A slider leads to a bright three season sunroom and a generous back deck. A living room, a bedroom and full bath complete the first floor. Upstairs, you’ll find comfortable bedrooms, another full bath. and a loft with a skylight that brings in natural light. The lower level features a family room with built-ins creating a cozy gathering space. Outside, enjoy the expansive backyard with mature trees, garden areas, and a classic barn-style shed with electricity for added storage or hobbies. The large detached 2-car garage offers excellent workspace and flexibility. This house is livable but requires TLC. This property presents a wonderful opportunity to add your personal touches in a place you can really call home!

357 Barre Rd, Oakham
21 Spencer Rd, Oakham
$339,000
3 Beds ⋅ 2 Baths ⋅ 73433422 MLS
opportunity in Oakham! This 3BR, 1.5BA home sits on a spacious lot in a quiet residential setting and features an oversized 3-car garage with finished space above. Property is being sold as-is, where-is, with no repairs or warranties from the seller. Buyer is responsible for the smoke certificate, Title V inspection, and any/all due diligence. Home requires updates and repairs but offers excellent potential for the right buyer or investor. Don’t miss the chance to bring this property back to life! Marketing Restrictions: Only Owner Occupants & Non-Profits may submit offers during the first 30 days. Investor offers may be submitted, but will not be reviewed until after the 30-day restriction period.

21 Spencer Rd, Oakham
67 Skyline Dr, Oakham
$150,000
4 Beds ⋅ 4 Baths ⋅ 73500355 MLS
Cash buyers only as this house had a major fire and the damage is extensive. Being sold as is. Seller has never lived in the home and has no other knowledge of condition, etc. . It was bought for a family member. Structure is not safe to enter so please do not enter....Beautiful neighborhood in Longview Estates....area of higher priced homes and the lot is level with over 3 acres. Quick access to major routes & parks. Private sewer and water.

67 Skyline Dr, Oakham
Lot 0 North Brookfield Rd, Oakham
$125,000
73468179 MLS
Beautiful 5.5+ acre lot in the lovely town of Oakham. Just over the New Braintree line with easy access to major routes and plenty of peace and quiet. This lot has great space for your dream home plus an ADU unit if that's what your looking for. . Seller will perc with an accepted offer.

Lot 0 North Brookfield Rd, Oakham
Crawford Rd, Oakham
$80,000
73557278 MLS
A 1-acre lot on a Country Oakham Road less that a 1 mile from the Rutland town line, approved 3-bedroom septic plan in hand, only needs a well to apply for a building permit. This a grandfathered lot 1 acre ready to go. Wooded gentle sloped lot. Call for details

Crawford Rd, Oakham
Bullard Rd, Oakham
$70,000
73462211 MLS
Gorgeous lot in an established neighborhood ready for your creative building ideas. Land has perc test in hand along with site plan and building plans. Back 1/3 has wetlands. Driveway already carved in to a cleared area.

Bullard Rd, Oakham

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