Oakham Homes for Sale

Welcome to Oakham, Massachusetts – a hidden gem nestled in the heart of Worcester County. Known for its picturesque landscapes and tight-knit community, Oakham offers a serene escape from the hustle and bustle of city life while still providing convenient access to urban amenities. With its rich history, charming rural atmosphere, and stunning natural beauty, Oakham is the perfect place to call home.

As you explore this delightful town, you’ll discover a range of outdoor activities, from hiking the scenic trails of the nearby Quabbin Reservoir to enjoying peaceful afternoons at local parks. Oakham is also home to a variety of local shops and eateries, where you can savor the flavors of the region and connect with friendly neighbors. The town’s commitment to preserving its natural beauty and fostering a sense of community makes it an ideal choice for families, retirees, and anyone seeking a tranquil lifestyle.

If you're in the market for a new home, Oakham has a diverse selection of properties for sale to suit your needs. From charming single-family homes with sprawling yards to modern residences that blend comfort and style, there’s something for everyone. The real estate market here is thriving, with opportunities for both first-time buyers and seasoned investors.

Embrace the Oakham lifestyle and find the perfect home that fits your vision. Whether you seek a peaceful retreat or a vibrant community, Oakham is ready to welcome you with open arms. Explore the homes for sale today and take the first step toward your new beginning in this enchanting town!

Newest Oakham Homes for Sale

$799,900

5 Beds ⋅ 4 Baths ⋅ 73568386 MLS

Welcome to Longview Estates! This beautifully built Colonial offers approx. 3,165 sq ft of living space with 5 bedrooms, 3.5 baths and a versatile in-law suite, all set on 5.4 private acres in Oakham. The main home features 3 bedrooms and 2.5 baths, hardwood flooring, a dining room with classic wainscoting, and an inviting kitchen with breakfast bar, dining nook, recessed lighting and charming window seat. Enjoy a private backyard, deck and 2-car garage. The spacious in-law offers 2 bedrooms, a full bath, hardwood flooring, cathedral ceilings, skylights, washer/dryer hookups and its own deck—ideal for extended family or multigenerational living. Quality 2x6 construction, irrigation system, generator-ready setup and a peaceful neighborhood setting complete this exceptional property. All appliances included.

107 Old School House Rd, Oakham

Listing courtesy of Listing Agent: Worcester County Homes Team from Listing Office: RE/MAX Vision.

$950,000

3 Beds ⋅ 3 Baths ⋅ 73565332 MLS

Tucked nearly 500 feet from the road on 6.83 gorgeous wooded acres, 730 Scott Road is the kind of property that feels like a getaway the moment you arrive. Custom built in 2003 with a high-end luxury cabin feel, this distinctive Cape offers over 3,200 sq. ft. of combined finished living space, exceptional versatility, and a private setting that is increasingly hard to find.The 2,421 sq. ft. main residence is spacious and inviting, with generous room sizes and thoughtful custom details throughout. The stunning living room is the heart of the home, where a wood stove creates a cozy focal point and oversized windows frame beautiful views of the expansive backyard and surrounding woods. The kitchen and dining spaces offer plenty of room to gather, while central air and radiant heat in the bathroom floors add everyday comfort.Outside, the setting truly shines. Surrounded by mature woods, the expansive backyard and patio provide plenty of room to entertain, unwind, garden, explore or simply enjoy the peace and privacy of your own acreage. An attached two-car garage adds convenience, while approximately 840 sq. ft. of additional finished space above offers incredible flexibility with a spacious living/flex area, full kitchen, bedroom, bonus area and full bath—ideal for guests, extended family, work-from-home needs or simply additional room to spread out. A huge unfinished basement offers even more potential. With acreage, privacy, incredible space and unmistakable character, 730 Scott Road is anything but ordinary - a private New England retreat designed for those looking for something truly special.

730 Scott Rd, Oakham

Listing courtesy of Listing Agent: Christy Querceto from Listing Office: The Q Group Realty, LLC.

$799,000

4 Beds ⋅ 3 Baths ⋅ 73563336 MLS

NEW CONSTRUCTION • MOVE-IN READY!Welcome home to this stunning open-concept Colonial, privately set back on a beautifully wooded lot. The exterior features composite front and rear porches, along with landscaping ready to bloom and welcome you home.Inside, you’ll find thoughtful finishes throughout, including ceramic tile, custom cabinetry with soft-close doors and drawers, granite countertops, and stainless-steel appliances. The spacious kitchen features a large pantry, making it a dream for both everyday living and entertaining.The expansive primary suite offers a walk-in closet and a luxurious tiled shower. Four additional second-floor bedrooms provide plenty of space for family and guests, while a first-floor office offers the flexibility needed for today’s lifestyle.Gather in the spacious great room, complete with vaulted ceilings and a fireplace—the perfect setting for relaxing or entertaining. Central air conditioning, efficient heating, and a two-car garage add comfort and convenience.With generous living space, privacy, beautiful wooded surroundings, and quality finishes throughout, this move-in-ready home is the perfect place to grow, gather, entertain, and enjoy for years to come!

260 Hunt, Oakham

Listing courtesy of Listing Agent: Eric Callahan from Listing Office: Prospective Realty INC.

$426,900

2 Beds ⋅ 1 Baths ⋅ 73554943 MLS

OPEN House 8/6 4:30-6:30pm Looking for a home with loads of character, natural warmth and history? Welcome to the Sanford-Crawford Carriage House a home that blends historical charms of yesteryear with contemporary comforts including custom woodwork & built-ins, beamed ceilings, wood floors, 1st floor laundry, spacious dining room off the fully-applianced country kitchen, generator connection and recessed family room that was a tailor shop in it's former use. Second level offers spacious primary bedroom with custom closet, secondary bedroom and an office/den/playroom with custom built-ins, and pull-down attic storage access completes the upper level. Step outside the front door onto the welcoming porch to relax, or outside the back door to enjoy your large private yard with deck, fenced garden area, carport, storage sheds. Recent updates include furnace, mini-splits, water treatment, well pump and more. Just a short walk to Town Center amenities...Library, Meeting House, Church, Playground and Summer Music on the Common! Explore the possibilities of quintessential New England country living in the beautiful town of Oakham, conveniently located only 20 minutes from Worcester.

33 Coldbrook Road, Oakham

Listing courtesy of Listing Agent: Irene Caruso from Listing Office: Michael Toomey & Associates, Inc..

$649,900

3 Beds ⋅ 3 Baths ⋅ 73542587 MLS

Set on a private 3-acre lot in desirable Oakham, this beautifully maintained 3-bedroom, 3-bath home combines spacious living with modern efficiency and peaceful country surroundings. The heart of the home is an inviting open-concept layout where the kitchen, dining area, and living spaces flow seamlessly together, creating the perfect setting for entertaining and everyday living. A stunning family room features soaring cathedral ceilings, oversized arched windows that flood the space with natural light, and a cozy gas fireplace, making it a true centerpiece of the home. This home also offers significant recent upgrades, including a new Generac whole-house generator for peace of mind, new Mass Save attic insulation for improved energy efficiency, and a high-efficiency heating system. The partially finished basement offers valuable additional living space and provides direct access to the attached two-car garage, making it ideal for a recreation room, home office, gym, or playroom.

499 Ware Corner Rd, Oakham

Listing courtesy of Listing Agent: Nicole Wickes from Listing Office: Northbound Realty Co.

$880,000

3 Beds ⋅ 2 Baths ⋅ 73531264 MLS

PRICE REDUCED !!! Enjoy country living at it's BEST !! Own a great estate with acres of privacy on both sides of the road. house is restored to perfection with modern touches. Property has open fields and wooded areas. 3 bedrooms , 2 baths. there is a private office over the garage for a great place to work at home. 2 car garage. Across the street is a work shop. Enjoy the 24x24 detached building in back yard. This would make a nice get away in your back yard. Loads of potential for crafts. Take a look at the many different things this property has to offer. Some furnishing can stay.

622 Spencer Rd., Oakham

Listing courtesy of Listing Agent: James Lovett from Listing Office: Century 21 North East.

$784,500

4 Beds ⋅ 3 Baths ⋅ 73529539 MLS

SAVE UP TO $689/MONTH YOUR FIRST YEAR! Seller offering a mortgage rate buydown of 1.5% the first year and 0.5% the second year! 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

Listing courtesy of Listing Agent: Trudy Risedorf from Listing Office: Lamacchia Realty, Inc..

$1,100,000

3 Beds ⋅ 4 Baths ⋅ 73517489 MLS

Situated on 10+ acres and overlooking the golf course, this sprawling young contemporary ranch was custom built for refined comfort throughout its 4000sf. The heart of the home is the expansive custom kitchen...perfect for family gatherings & entertaining w/counterspace & cabinetry galore,double sinks,double ovens, propane cooktop, wet bar & flowing seamlessly to the dining, sitting & living rooms w/hardwoods, custom built-ins, propane fireplace,retractable tv. The primary bedroom retreat w/double walk-in closets, spa-like bath w/walk-in tile shower, soaking tub, double vanity, radiant heat & laundry room. Two additional sizable bedroom en-suites for family or guests. The recently completed lower level includes a family/game room, exercise room and office...leaving plenty of space for workshop & storage. Enjoy the outdoor spaces that are as inviting as the indoor...the front porch w/spectacular sunrises and the back porch by the wood burning fireplace w/stunning sunsets over sweeping golf course fairway views.

1776 Old Turnpike Road, Oakham

Listing courtesy of Listing Agent: Irene Caruso from Listing Office: Michael Toomey & Associates, Inc..

$600,000

3 Beds ⋅ 3 Baths ⋅ 73489954 MLS

Seller says sell!! Big Price Drop on this five year young beauty that has everything you've been looking for in a new home coupled with the privacy of a rural setting. Featuring a modern floorplan, amazing kitchen, 2nd floor laundry, spacious bedrooms and loads of sunlight. There is nothing to do but move in and start living. Set way off the street with a new fully fenced in yard, new driveway and classic country front porch, this fantastic property exudes comfort and peace. Only 30 scenic minutes from Worchester, this beauty is the escape you've been looking for. Come see for yourself. You won't be disappointed.

1310 N Brookfield Rd, Oakham

Listing courtesy of Listing Agent: Bryan Kaye from Listing Office: BKaye Realty.

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