Oakham Homes with Colonial Style

Welcome to Oakham, Massachusetts – a hidden gem nestled in the heart of Worcester County. This charming town is a picturesque blend of rural tranquility and vibrant community spirit, making it an ideal place for those seeking a serene lifestyle while remaining connected to the conveniences of modern living. Oakham is renowned for its stunning natural landscapes, including lush forests and serene lakes, offering endless opportunities for outdoor activities such as hiking, fishing, and horseback riding.

One of the most appealing features of Oakham is its rich architectural heritage, particularly the timeless Colonial-style homes that grace its streets. These homes, characterized by their symmetrical facades, gabled roofs, and classic brick exteriors, exude a sense of history and charm that captivates both residents and visitors alike. With spacious layouts and elegant details, Colonial homes in Oakham provide the perfect backdrop for family gatherings and cozy evenings by the fireplace.

Living in Oakham means enjoying a close-knit community that values tradition and neighborly connections. The town hosts various events throughout the year, fostering a sense of belonging and camaraderie among residents. Whether you’re exploring the local farmer's market or participating in seasonal festivals, there’s always something happening in this vibrant town.

If you’re looking for a place that combines the beauty of nature with the warmth of a welcoming community, Oakham is the perfect choice. Discover the charm of Colonial-style homes and experience the idyllic lifestyle that awaits you in this enchanting town. Come and make Oakham your home today!

Newest Oakham Homes with Colonial Style

$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.

$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.

$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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