Oakham Real Estate

Welcome to Oakham, Massachusetts—a hidden gem nestled in the heart of Worcester County. This picturesque town, known for its serene landscapes and tight-knit community, offers a delightful blend of rural charm and modern conveniences. With its rich history dating back to the 18th century, Oakham is a place where the past meets the present, making it a perfect spot for families, retirees, and anyone seeking a peaceful retreat.

Oakham is characterized by its stunning natural beauty, featuring rolling hills, lush forests, and tranquil lakes. Outdoor enthusiasts will revel in the abundant recreational opportunities available, from hiking and biking along scenic trails to fishing and kayaking in the nearby waters. The town is also home to several parks and conservation areas, providing ample space for picnics, leisurely walks, and family gatherings.

Despite its small-town feel, Oakham boasts a vibrant community spirit, with a variety of local events and festivals throughout the year. Residents enjoy a strong sense of camaraderie, making it easy to forge friendships and connections. The town’s excellent school system and commitment to community engagement make it an ideal place to raise children.

Conveniently located just a short drive from Worcester and other major cities in Massachusetts, Oakham offers easy access to urban amenities while maintaining its tranquil atmosphere. Whether you’re exploring the local shops, savoring delicious cuisine at nearby eateries, or simply enjoying the stunning views, Oakham is a place where memories are made and cherished. Come discover the charm of Oakham—your new home awaits!

Newest Listings in Oakham

$426,900

2 Beds ⋅ 1 Baths ⋅ 73554943 MLS

Warm and Welcoming! This 1526sf Colonial home blends historical charm with contemporary comforts including custom woodwork & built-ins, beamed ceilings, recessed family room w/cathedral ceiling & electric fireplace, 1st floor laundry, spacious dining room off the fully-applianced country kitchen and generator connection. Second level with two bedrooms and office space with built-in private retreats. Step outside the front door onto the welcoming porch to relax, or outside the back door to enjoy your large private yard with deck, enclosed garden area, carport, storage sheds. Recent updates include furnace, mini-splits, water treatment, well pump and more. Explore the possibilities of quintessential New England living in the beautiful town of Oakham!

33 Coldbrook Road, Oakham

$599,900

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

$869,900

3 Beds ⋅ 2 Baths ⋅ 73549605 MLS

Escape to ultimate privacy in Oakham! Set on 9.7 acres & surrounded by protected state forest, this home is offering exceptional seclusion & a rare natural setting. This 3-bedroom, 1.5-bath property features hardwood flooring, partial carpet flooring, vinyl flooring, & ceramic tiling. Recent updates include a brand new septic system, wooden shingles replaced, new vinyl & carpet flooring, & a remodeled first-floor half bath. Opportunities can include the 9.7 acres of expansive wooded land behind which offers potential for subdivided lots or other future development. Located on a private road away from major traffic, the property offers abundant wildlife & forest views that resembles northern New England. Despite its secluded setting, it remains within a short radius to a golf club like Kettle Brook, Worcester Regional Airport, and the city of Worcester. Perfect balance of accessibility and privacy, this home is ideal for those seeking both rural living and proximity to city amenities.

16 Flint Rd, Oakham

$399,900

3 Beds ⋅ 2 Baths ⋅ 73542913 MLS

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 property presents a wonderful opportunity to add your personal touches in a place you can really call home!

357 Barre Rd, Oakham

$654,000

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

$995,000

3 Beds ⋅ 2 Baths ⋅ 73531264 MLS

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

$789,700

4 Beds ⋅ 3 Baths ⋅ 73529539 MLS

Escape the hustle and bustle and discover the privacy of your own 14-acre retreat. Whether you're casting a line, enjoying a boat ride, or taking in the peaceful surroundings, you'll love the relaxation and recreation this property offers. Blending character and functionality throughout, a soaring vaulted entry welcomes you inside, while the updated kitchen features quartz countertops, SS appliances, beautiful 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 and creates a comfortable living space. The dining room is perfect for large family gatherings. The primary suite offers a private retreat w/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 installed about 8 yrs ago. House resided about 5 yrs ago.

775 East Hill Road, Oakham

$675,000

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

$1,100,000

3 Beds ⋅ 4 Baths ⋅ 73517489 MLS

Situated on 10+ acres, 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 & family 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 bonus/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 the sweeping fairway views.

1776 Old Turnpike Road, Oakham

$829,000

4 Beds ⋅ 3 Baths ⋅ 73516592 MLS

!! NEW CONSTRUCTION !! open concept Colonial, Under construction now. Home includes extensive hardwoods, composite front porch, central AC and heating, ceramic tiles, custom cabinetry with "soft close" cabinets, granite and stainless steel kitchen that will delight any home gourmet, large master bedroom suite with walk in closet. Still time to make some choices.

260-A Hunt, Oakham

$620,000

3 Beds ⋅ 3 Baths ⋅ 73489954 MLS

This five year young beauty is 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

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