Rutland Real Estate

Welcome to Rutland, Massachusetts – a hidden gem nestled in the picturesque Worcester County! Known for its charming small-town vibe and stunning natural landscapes, Rutland offers a unique blend of rural tranquility and modern convenience, making it an ideal place to call home.

With its rich history dating back to the early 18th century, Rutland boasts a quaint New England charm that captivates residents and visitors alike. The town is surrounded by lush forests, serene lakes, and rolling hills, providing ample opportunities for outdoor enthusiasts. Whether you enjoy hiking, fishing, or simply taking in the breathtaking views, Rutland’s natural beauty is sure to inspire.

Rutland is not just about its scenic landscapes; it also has a vibrant community spirit. The town hosts various local events throughout the year, from farmers' markets to seasonal festivals, fostering a strong sense of camaraderie among residents. Families will appreciate the excellent school system, which prioritizes education and community involvement.

Conveniently located just a short drive from Worcester, Rutland offers easy access to urban amenities while maintaining its peaceful, rural atmosphere. With a variety of local shops, restaurants, and recreational facilities, you’ll find everything you need close to home.

If you’re looking for a place that combines the best of both worlds – a serene lifestyle with the convenience of nearby city living – Rutland, MA, is the perfect destination. Come explore the charm and warmth of this delightful town, and discover why so many have chosen to make Rutland their home!

Newest Listings in Rutland

$385,000

3 Beds ⋅ 2 Baths ⋅ 73568333 MLS

Discover the charm of 8 Beechwood Dr in Rutland, MA. Built in 1972, this inviting 1,312+-square-foot home is located in a well established neighborhood and located close to all that Rutland has to offer. The open-plan kitchen features matching black appliances and a center island, perfect for additional counter space or casual dining. The living room is warm and welcoming w/ a large bay window for natural light and a cozy brick-accented fireplace for the cooler weather ahead. Three comfortable bedrooms include closets and hardwood flooring, while the home’s 1.5 bathrooms offer spacious, functional layouts. The BONUS room off the kitchen features a cathedral ceiling, skylights, a slider to the back deck and a lovely view of the back yard. Customize the partially finished lower level to fit your needs! Convenient one car garage for the upcoming winter months. Excellent location to area amenities, inviting spaces throughout and a fantastic value! This is one to call home!

8 Beechwood Dr, Rutland

Listing courtesy of Listing Agent: Katherine Larose from Listing Office: Keller Williams Pinnacle Central.

$210,000

2 Beds ⋅ 1 Baths ⋅ 73566836 MLS ⋅ ['Countryside Estates'] BLDG.

Enjoy the ease of ground floor living in this beautifully updated 2-bedroom 1 bathroom condo located in the highly desirable town of Rutland. This inviting unit offers central air conditioning for year-round comfort, a functional and flowing layout, and low-maintenance living at its finest. With new stainless steel kitchen appliances and atiled bathroom with glass shower doors, this unit is well appointed with modern features. The bright living spaces provide a welcoming atmosphere. Custom closets add to convenient storage. Nestled in a peaceful Countryside Estates community, you’ll appreciate the charm and small-town feel of Rutland while remaining close to local shops, restaurants, parks, and major commuter routes. This condo is an excellent choice!

176 Maple Ave Unit 1-26, Rutland

Listing courtesy of Listing Agent: Team Molet from Listing Office: Keller Williams Realty North Central.

$215,000

2 Beds ⋅ 1 Baths ⋅ 73566746 MLS ⋅ ['Countryside Estates'] BLDG.

Welcome to one of the largest floor plans in this well-maintained complex, a spacious 999 square foot, two-bedroom, one-bath condo in the front building with easy access and a great location. This unit has been thoughtfully refreshed and is truly move-in ready, featuring new carpet throughout, fresh paint, and abundant natural light that gives every room a bright, welcoming feel. The kitchen has been updated with beautiful new plank flooring, creating a bright and welcoming space to cook and gather. The bathroom has also been refreshed with new flooring and vanity giving it that same clean, fresh feeling throughout. The primary bedroom offers a large walk-in closet, giving you the storage space that's often hard to find in a condo this size. Comfort and convenience are built in, with central air, a Wi-Fi thermostat, and Wi-Fi carbon and smoke detectors for smart, connected living. Step out onto your private balcony to take in a beautiful view, a perfect spot for morning coffee or unwinding at the end of the day. In building Wi-Fi Laundry. Secured building adds an extra layer of ease and peace of mind. The complex itself offers great amenities, including a playground and tennis court, with an in-ground pool currently being refreshed and expected to be up and running for the 2027 season. Rutland sits in the geographic center of Massachusetts and offers a wonderful mix of small-town charm and outdoor recreation, with easy access to Rutland State Park and Whitehall Pond for hiking, swimming, and picnicking, plus nearby Wachusett Mountain for skiing and scenic views. History and culture lovers will appreciate the proximity to Old Sturbridge Village, one of the country's largest living history museums, and convenient access to Worcester offers shopping, dining, and commuting options close by. Don't miss your chance to own one of the largest and most updated units in this sought-after complex.

176 Maple Ave Unit 1-36, Rutland

Listing courtesy of Listing Agent: Therrien Realty Team from Listing Office: The Neighborhood Realty Group.

$649,000

4 Beds ⋅ 3 Baths ⋅ 73566539 MLS

Your Search Ends Here! Pride of ownership shines throughout this meticulously maintained home, lovingly cared for by its original owners for over four decades. Set on a quiet street just outside the center of town, this private oasis offers over 1.5 acres of beautifully manicured grounds, including a garden that produces some of the best fruits and vegetables in town. Inside, you’ll find an expansive, open-concept layout featuring a beautifully renovated kitchen and generous living spaces designed for everyday living and entertaining. With 4 bedrooms and 2.5 bathrooms, including bedrooms and bathrooms on both levels, this home offers exceptional flexibility for families of all sizes, multi-generational living, and guests. The property is truly move-in ready, featuring replacement windows and doors, vinyl siding, and owned solar panels for added efficiency. Outside, the professionally landscaped grounds provide plenty of space to relax, entertain, garden, and enjoy your own private sanctuary.Whether you’re an entertainer, gardener, looking for multi-generational space, or simply seeking a meticulously maintained home with room to grow, this one checks all the boxes. Don’t miss this rare opportunity—schedule your private showing today!

10 Bethany Dr, Rutland

Listing courtesy of Listing Agent: Evan Foley from Listing Office: REMAX Executive Realty.

$459,900

3 Beds ⋅ 2 Baths ⋅ 73563783 MLS

Presenting this single-family residence, constructed in 1987, encompassing 1190 square feet of refined living space at 4 Sycamore Dr, Rutland, MA. This property, set upon a generous 17,424 square foot lot, offers a compelling opportunity for discerning buyers seeking a blend of comfort and functional design within a desirable setting. The residence features three thoughtfully proportioned bedrooms, providing versatile accommodations for various lifestyle needs. Complementing these are two full bathrooms, meticulously designed to offer convenience and privacy. Discover the exceptional potential within this Rutland, MA property; an immediate inquiry is encouraged to explore this unique offering.

4 Sycamore Dr, Rutland

Listing courtesy of Listing Agent: Jeffrey Brooks from Listing Office: Coldwell Banker Realty - Worcester.

$274,900

2 Beds ⋅ 1 Baths ⋅ 73564310 MLS

Wow - why rent when you can own - this completely renovated home is ready to move into! Enjoy the charm of lakeside living in this inviting 2-bedroom home, perfectly suited for year-round enjoyment or a relaxing getaway. The open-concept kitchen and family room create a bright and welcoming space for gathering with family and friends, while the deck provides the perfect spot for morning coffee, outdoor dining, or simply taking in the peaceful surroundings. Just a short walk away, you’ll find access to a private beach on the lake, offering swimming, boating, and fishing opportunities. Updates include new kitchen, full bath, flooring, hot water tank,interior and exterior paint. In addition the furnace is only 5 yrs old with a newer oil tank and new cap on chimney. This home has a full basement which is rare in this community with traditional forced air heat. A wonderful opportunity to enjoy the beauty of lake living with recreation right at your doorstep! Welcome Home!

2 Kosta Ave., Rutland

Listing courtesy of Listing Agent: Jeffrey Gibbs from Listing Office: Gibbs Realty Inc..

$749,000

4 Beds ⋅ 3 Baths ⋅ 73562107 MLS

PRIVACY! Come home to your own woods and enjoy the stars, & peaceful beauty this 5.7 ACRE PROPERTY provides | OPEN HOUSE 8/30, NOON TO 2:00 | A 1999 CONTEMPORARY CAPE nestled in the back of the property with a beautifully landscaped front yard including terraced lawns, fruit trees and spectacular old stone patio surrounding a firepit. Deck and covered front porch look out on all. OPEN CONCEPT 1st FLR! Kitchen, Dining and cathedral ceiling, large picture window Living Rm all open to one another. 1st FLR PRIMARY BR, with huge walk-in closet and bath. Half bath for guests. Balcony, 3 Bdrm's and a bath on 2nd floor. One of upstairs bedrooms is very large. Unfinished basement has garage door & can be converted to an under home single garage. New kitchen appliances 2021, new carpets 2022, freshly painted inside & out, above ground pool, AWESOME KITCHEN MAKE OVER w/ NEW ISLAND, fenced side yard. Convenient location right off 62. Comet Pond boat ramp 1 mile away. Great school system, Right to Farm Com, Mt Wachusett 18 min away, all add up to THE PERFECT HOME if you love privacy and the outdoors!

115 River Rd, Rutland

Listing courtesy of Listing Agent: Janet Schoeny from Listing Office: RE/MAX Vision.

$550,000

3 Beds ⋅ 3 Baths ⋅ 73558481 MLS

Contemporary style meets peaceful country living on just over five private acres in Rutland. Designed for both everyday comfort and entertaining, the open-concept layout features a dramatic living room with vaulted ceilings, bamboo flooring, built-in shelving, and a stunning floor-to-ceiling stone fireplace with a propane insert. The living area flows seamlessly into the dining room and spacious kitchen, where a large center island, abundant cabinetry and countertop space, breakfast bar, and sliders to the private back deck create the perfect gathering space. Three to four generously sized bedrooms are complemented by a finished lower level with a large bonus room, additional flexible living space, and ample storage. Outside, enjoy a level garden area for flowers or vegetables, a new storage shed, an Amish-built chicken coop with an enclosed run for 4–8 hens, an attached garage, and plenty of off-street parking. With two-zone heat and central air, plus easy access to the Midstate Trail just minutes away, this property offers the ideal blend of comfort, privacy, and outdoor living.

251 Pleasantdale Road, Rutland

Listing courtesy of Listing Agent: Elisha Lynch from Listing Office: Lamacchia Realty, Inc..

$625,000

3 Beds ⋅ 4 Baths ⋅ 73557968 MLS

Price Improved! Set in a popular Rutland neighborhood with sidewalk-lined streets and tucked-away cul-de-sacs, this distinctive dormered Cape offers an appealing blend of space, comfort, and flexibility. Built for the builder's own family member and carefully maintained over the years, this home features 3 bedrooms, including primary with en suite; 3.5 baths; main-level laundry, and a spacious kitchen with quartz countertops, stainless appliances, a built-in wine cooler, and a dining area with sliders overlooking a wooded backdrop. Formal living and dining rooms provide plenty of space for entertaining, while the family room serves as a natural gathering place with its brick fireplace. Crown moldings, decorative trim, and vaulted ceilings add character throughout. Outside, an expansive two-tier composite deck overlooks the private backyard and offers plenty of room for grilling, gathering with friends, hosting summer cookouts, or unwinding at the end of the day. The finished walkout lower level adds exceptional flexibility with its own kitchen, ¾ bath, and separate entrance, making it ideal for extended family, guests, a home office, hobby space, or changing household needs. With attractive curb appeal, a highly functional floor plan, and convenient access in and out of town, this home delivers the space, flexibility, and location to accommodate a wide range of needs, both now and in the years ahead.

17 Sycamore Drive, Rutland

Listing courtesy of Listing Agent: Lisa Hugo from Listing Office: Coldwell Banker Realty - Worcester.

$489,000

2 Beds ⋅ 2 Baths ⋅ 73557945 MLS ⋅ ['Harmony Place'] BLDG.

Under construction home in Harmony Place - Rutland's Newest 55+ Community. This beautiful, well-built attached home offers 1,447 sq ft of single-level living area, a primary bedroom with en-suite bathroom, a 2nd bedroom, a guest bath and a laundry room/pocket office or pantry. Enjoy natural light from a large picture window in the dining area and a back deck with wooded views. The interior is a blank slate for you to make your own! Choose your flooring, cabinet colors, countertops, and design your custom shower. Enjoy maintenance-free living in this new 55+ community. Amenities are on the way, including a clubhouse with an exercise room, a nature trail with fitness stations, pickelball, dog parks and a community garden.

21 Fidelity Drive Unit 73, Rutland

Listing courtesy of Listing Agent: Karin Anderson from Listing Office: Harbor Classic Realty.

$489,000

2 Beds ⋅ 2 Baths ⋅ 73557946 MLS ⋅ ['Harmony Place'] BLDG.

23 Fidelity Drive Unit 74, Rutland

Listing courtesy of Listing Agent: Karin Anderson from Listing Office: Harbor Classic Realty.

$498,000

2 Beds ⋅ 2 Baths ⋅ 73557939 MLS ⋅ ['Harmony Place'] BLDG.

Under construction home in Harmony Place - Rutland's Newest 55+ Community. This beautiful, well-built attached home offers 1,582 sq ft of single-level living area, a primary bedroom with en-suite bathroom, a 2nd bedroom, a guest bath and a versatile flex room perfect for an office, den or hobby room. Enjoy natural light from a large picture window in the dining area and a back deck with wooded views. The interior is a blank slate for you to make your own! Choose your flooring, cabinet colors, countertops, and design your custom shower. Enjoy maintenance-free living in this new 55+ community. Amenities are on the way, including a clubhouse with an exercise room, a nature trail with fitness stations, pickelball, dog parks and a community garden.

19 Fidelity Drive Unit 72, Rutland

Listing courtesy of Listing Agent: Karin Anderson from Listing Office: Harbor Classic Realty.

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