Rutland Real Estate

Welcome to Rutland, Massachusetts—a charming town nestled in the heart of Worcester County. Known for its picturesque landscapes and a strong sense of community, Rutland offers a perfect blend of rural charm and modern amenities. With its rich history dating back to the 18th century, this quaint town is a hidden gem that attracts residents and visitors alike.

Rutland is surrounded by stunning natural beauty, with sprawling woodlands, serene lakes, and picturesque hiking trails. Outdoor enthusiasts will find plenty to enjoy, whether it's a peaceful day of fishing at the scenic Rutland State Park or an invigorating hike through the lush trails of the nearby Wachusett Mountain. The town's commitment to preserving its natural resources ensures that residents can enjoy these outdoor activities year-round.

The community spirit in Rutland is palpable, with various local events and gatherings that bring neighbors together. From farmers' markets to seasonal festivals, there’s always something happening that fosters a sense of belonging. Families will appreciate the highly-rated schools and safe neighborhoods, making Rutland an ideal place to raise children.

Conveniently located just a short drive from Worcester, Rutland offers easy access to urban amenities while maintaining its tranquil, small-town atmosphere. With a variety of local shops, restaurants, and recreational facilities, residents can enjoy the best of both worlds.

Whether you're looking to settle down in a peaceful community or seeking a weekend retreat, Rutland, MA, is a place where you can truly feel at home. Come discover the charm and warmth of this delightful town!

Newest Listings in Rutland

$465,000

3 Beds ⋅ 2 Baths ⋅ 73576178 MLS

Welcome to 336 Pommogussett Road in Rutland, a charming Cape set back from the road on 1.64 acres, offering privacy, space, and some fantastic recent upgrades! This 3-bedroom, 2-full-bath home features a beautifully renovated kitchen with a center island, granite countertops, upgraded cabinetry, and stainless steel appliances. The open-concept front-to-back living and dining area provides plenty of space for everyday living and entertaining.Enjoy the convenience of a first-floor bedroom and full bath, while the second floor offers two additional bedrooms and another full bath. The unfinished basement provides great potential for future expansion, storage, a home gym, or additional living space.Major improvements make this home even more attractive, including a BRAND-NEW ROOF, BRAND-NEW SEPTIC SYSTEM, and a new mini-duct heating and cooling system, giving the next owner added comfort and peace of mind.Outside, you’ll find a nicely landscaped yard with a flat backyard, plenty of off-street parking, and room to enjoy the outdoors. Conveniently located near the center of Rutland, major routes, hiking trails, fishing, and local ponds.Move-in ready with the big-ticket improvements already completed—come see everything this Rutland home has to offer!

336 Pommogussett Rd, Rutland

$749,990

3 Beds ⋅ 2 Baths ⋅ 73575778 MLS

This brand new, beautifully designed ranch offers the ease of single-level living with thoughtful finishes throughout. The open floor plan seamlessly connects the kitchen, dining room, and living room — ideal for everyday living and entertaining. The kitchen shines with quartz counters, a large center island, stainless steel appliances, and sleek finishes. Unwind on the covered front porch or relax in the open living room where sunsets pour through the windows.All three bedrooms offer comfort and ample space, including a standout primary suite with a custom-built walk-in closet and en suite bath featuring a tiled shower. The unfinished, walk-out basement offers potential to add additional living space and the oversized two car garage adds valuable storage space.A large composite deck overlooks the flat, tree-lined backyard- providing endless possibilities. The best part though is the location! Set on a picturesque country road lined with stone walls and surrounded by trees- it is the epitome of a private, relaxing setting.

262 Glenwood Rd, Rutland

$375,000

3 Beds ⋅ 3 Baths ⋅ 73573692 MLS ⋅ ['Central Tree Place'] BLDG.

** Open House Saturday Sept 12, 11:00 am - Noon ** Some homes you just browse, this is the one you'll want to buy. The pride of ownership in this one owner duplex-style townhouse shows in all the little things, like hardwood floors that still catch the light in the living room, and oak kitchen cabinets that have never had anything but pride behind them. The kitchen opens into a dining area and out through sliding doors to a private deck, fenced and shaded, where a few tomato plants are still coming in along the rail. Upstairs, the primary bedroom has its own full bath and a quiet corner for a desk or a vanity; two more bedrooms share a second full bath, each with room enough for a real life being lived in them – not just a bed shoved in a box. In the lower level are the one-car garage and a finishable space round out the practical side (storage, workout space, home office - whatever you need it to be.) The condo fee is low enough that it won't change your math. "Great location" are words thrown around in real estate descriptions, yet it's true here: You're in the Wachusett Regional School District, only 5 mins from the town pool or the Rail Trail, under 10 mins to the beach at Long Pond and under 20 mins to hike or ski at Mt Wachusett. Catch the lights right, and you can be on I-190 in under 15 mins.

16 Central Tree Rd Unit 16, Rutland

$125,000

1 Baths ⋅ 73573070 MLS ⋅ ['Countryside Estates'] BLDG.

Affordable Studio Condo in the heart of Massachusetts. Bright, clean, & updated throughout. Stainless appliances in the seperate kitchen. Sliding glass doors look out to private back area of building. Great for anyone looking for affordable living, make a great rental unit for investors. Close to town center, Rutland activities and all the Wachusett region has to offer.

176 Maple Ave Unit 2-4, Rutland

$585,000

4 Beds ⋅ 3 Baths ⋅ 73570316 MLS

Showings begin immediately. Open House Sat 9/5 1-2:30 pm . There is something special about a home that feels like it was designed for the way you actually want to live! Custom built in 2013, this 4 bedroom 2.5 bath home offers an open, spacious feel as soon as you open the front door. You will love the ease of one level living, and plenty of room to gather, unwind and make it your own.The heart of the home is the enormous kitchen with massive center island for quick bites and gatherings. You will appreciate the custom cabinetry, soft close drawers, tiled floors and gorgeous granite countertops all creating a relaxing space made for everything from quiet morning coffee to holidays filled with family and friends. Hardwood floors flow throughout the main level, and the open design keeps everyone connected while still giving you room to spread out. Step through the kitchen sliders onto the huge deck and imagine summer dinners outside, peaceful mornings with coffee, or simply sitting back and enjoying the beautiful backyard view.With three bedrooms and two full baths on the main level, everyday living can happen comfortably on one floor .The oversized Main bedroom has its own private bath as well as walk in closet. And when you want more space, the bright walkout lower level delivers a large family room, extra bedroom , bath and lots of storage place with an abundance of light ! Outside is beautiful landscaping and a covered front porch to sip coffee or cocktails and soak in the view . This home truly has it all!

273 Maple Ave, Rutland

$399,900

4 Beds ⋅ 3 Baths ⋅ 73569616 MLS

Large 5 bedroom and 2.5 bath home looking for a new owner, Large open kitchen area. Spacious living room. Full sized bedrooms. Legal ADU unit with new kitchen. 4 season room. New roof. Great lot and location.

156 Main St, Rutland

$349,900

3 Beds ⋅ 1 Baths ⋅ 73568702 MLS

Charming, beautifully updated, and move-in ready, this is a home that feels easy to love from the moment you walk in. The bright, renovated kitchen is the heart of the home, featuring crisp white cabinetry, distinctive countertops, open shelving, and stainless steel appliances added in 2023. It flows naturally into the cozy living room, creating an inviting layout for both everyday living and entertaining. Two well-appointed bedrooms and a full bath complete the first floor, while new luxury vinyl plank flooring and fresh paint carry throughout the first and second levels. Upstairs, the flexible layout can be used as two separate rooms or one spacious retreat, offering options for bedrooms, a playroom, studio, or additional living space. The finished lower level provides even more usable space and is ready for cosmetic updates to make it your own. A 2025 smart washer and dryer and plenty of additional storage add everyday convenience. Outside, the desirable corner lot offers a private backyard with room to relax, entertain, and enjoy gardening in the large metal raised beds that will remain for the next owner. A detached one-car garage provides additional storage, along with plenty of off-street parking. With town water and sewer, a newer heating system, vinyl siding, and a 2021 roof, many of the big-ticket items are already in place. Conveniently located just minutes from downtown and major routes.

16 Highland Park Rd, Rutland

$749,900

3 Beds ⋅ 4 Baths ⋅ 73568589 MLS

Welcome to Brunelle East, where this beautifully updated and thoughtfully designed home delivers the space, comfort, and setting to truly enjoy everyday living! Situated on a generous .69-acre lot near Moulton Pond, this 3-bedroom home offers over 2,250 SF of above-grade living space with an additional finished lower level. The open-concept kitchen and dining area creates a natural heart of the home, ideal for everything from everyday meals to hosting family and friends. The remodeled kitchen is beautifully appointed with quartz countertops, a center island, stainless steel appliances, crown molding, and a pantry, with convenient access to the backyard and deck. Just a few steps above, the impressive 24' x 24' elevated living room creates a distinctive yet connected space, featuring a vaulted ceiling, fireplace, decorative moldings, recessed lighting, engineered hardwood flooring, and oversized windows that bring in an abundance of natural light. Outside, the fully fenced and professionally landscaped yard provides a wonderful setting for summer cookouts, gatherings, pets, gardening, or simply relaxing at the end of the day. Upstairs, the vaulted primary suite offers a walk-in closet and private full bath, while two additional bedrooms and a second full bath provide plenty of room to spread out. A dedicated first-floor office makes working from home easy, while the finished lower-level family room with half bath offers even more flexibility for movie nights, a game room, fitness area, or additional entertaining space. Complete with first-floor laundry, a 2-car attached garage, ample paved parking, central air and ductless mini-splits, public water and sewer, this is a home that feels as good to live in as it looks. Turn-key home ready to be enjoyed!

2 Horizon Road, Rutland

$385,000

3 Beds ⋅ 2 Baths ⋅ 73568333 MLS

*Offer Deadline: 8/31 @ 5pm* 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!

8 Beechwood Dr, Rutland

$199,000

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

$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

$444,900

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

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