Rutland Homes for Sale

Welcome to Rutland, Massachusetts, a charming town nestled in the heart of Worcester County. Known for its picturesque landscapes and friendly community, Rutland offers a perfect blend of rural charm and suburban convenience. With its rich history, serene parks, and vibrant local culture, this hidden gem is an ideal place to call home.

One of the standout features of Rutland is its commitment to preserving natural beauty. The town is surrounded by lush forests and scenic trails, making it a haven for outdoor enthusiasts. Whether you enjoy hiking, biking, or simply taking leisurely strolls, the breathtaking scenery will leave you enchanted.

Rutland is also home to a tight-knit community that takes pride in its local events and gatherings. From seasonal festivals to farmers' markets, there’s always something happening that brings residents together. Families will appreciate the town’s excellent school system, which is dedicated to fostering a supportive learning environment for children of all ages.

For those considering a move, Rutland offers a diverse range of homes for sale that cater to various tastes and budgets. From charming single-family homes with spacious yards to modern townhouses, there’s a perfect fit for everyone. The real estate market here is thriving, providing ample opportunities for first-time buyers and seasoned investors alike.

Discover the magic of Rutland, where community spirit meets tranquil living. Explore the homes for sale today and find your dream residence in this delightful town!

Newest Rutland Homes for Sale

$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

Listing courtesy of Listing Agent: Melissa Clark from Listing Office: Coldwell Banker Realty - Worcester.

$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

Listing courtesy of Listing Agent: James Kalogeropoulos from Listing Office: RE/MAX Partners.

$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.

$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.

$689,900

3 Beds ⋅ 3 Baths ⋅ 73556183 MLS

Comfort meets style at 95 Prescott Street, the one you’ve been waiting for. This impressive 2017 Colonial delivers 3 bedrooms, 2.5 baths, and 2,248 square feet of thoughtfully upgraded living space on a private 2.02-acre lot in the sought-after Wachusett Regional School District. From the moment you arrive, the curb appeal stops you in your tracks—beautiful landscaping, a striking stone walkway, and a classic Colonial façade that sits proudly among the trees. Step inside and feel the difference. Soaring vaulted ceilings, a massive family room anchored by a cozy fireplace—the perfect spot for movie nights, holidays, or just unwinding after a long day. The light-drenched sunroom is pure relaxation. Beautiful hardwood floors run throughout the main living areas, adding warmth and elegance. The chef’s kitchen is a true showstopper. Stainless steel appliances, stone countertops, a deep farmer’s sink, gas range with powerful vent hood, double wall oven, under-counter microwave, and a special-order counter-depth refrigerator with see-through door create a space that is as functional as it is stunning. The open layout connects effortlessly to a dedicated dining room, making entertaining easy and elegant. The primary suite offers a peaceful retreat complete with a large walk-in closet. First-floor laundry and a versatile office/bonus room add everyday convenience that modern families love. Central air keeps the entire home comfortable year-round. Head downstairs and discover even more potential. The partially finished basement delivers tons of bonus space with polished concrete floors—ideal for a home gym, playroom, media area, or future expansion. Outside this property continues to shine. Enjoy the composite deck, covered patio complete with outdoor bar and seating, and a private backyard that feels like your own retreat. Professional landscaping, mature plantings, and a storage shed complete the package. Whether you’re hosting summer gatherings or simply enjoying a quiet morning coffee, the outdoor living spaces deliver. Located in the sought after, growing town of Rutland with easy access to parks, trails, ponds, outdoor recreation areas and the Wachusett School District, this home offers the perfect balance of privacy, space, and convenience. Upgraded. Private. Thoughtfully designed. Unforgettable. 95 Prescott Street isn’t just a house—it’s the lifestyle you’ve been looking for. Don’t miss it! Open House Sunday, August 2nd, 1-3!

95 Prescott St, Rutland

Listing courtesy of Listing Agent: Jesse Gadarowski from Listing Office: Prospective Realty INC.

$649,900

3 Beds ⋅ 3 Baths ⋅ 73555134 MLS

One owner custom designed cape style home offering front to back family room with palladium window, cathedral ceilings, hdwd floors and French doors , open to dine in kitchen with breakfast bar, granite counters, and informal dining area. Formal DR continues with hardwood floors plus formal living room or den with wood Fireplace offering warmth and comfort . Open foyer takes you to the 2nd floor where you will find 3 bedrooms all with hardwood floors & guest bath . Primary suite has bay style window, spacious closet and large oversized private bath. Lower level has 2 finished rooms not inc in GLA perfect for a playroom or office area. Complete with 2 car garage , new deck and walk way all on 1.5 acre lot.

249 Pleasantdale Road, Rutland

Listing courtesy of Listing Agent: Tracey Fiorelli from Listing Office: Janice Mitchell R.E., Inc.

$1,985,000

4 Beds ⋅ 4 Baths ⋅ 73552343 MLS

Experience true waterfront living on Demond Pond with 300+ feet of full-recreation frontage and ultimate privacy abutting conservation land. This 4,000 sq ft, three-level home features a spectacular Sun Room wrapped in windows, offering panoramic pond views and stunning sunsets year-round. The first floor includes 9' ceilings with hardwood floors, a Dining and Living Room, and an applianced Kitchen. The Family Room adds a gas fireplace and French doors framing more waterfront scenery. The Main En Suite offers a private balcony, jetted tub, sunset vistas, and walk-in closet, complemented by 3.5 baths and four spacious bedrooms. Outdoor living shines with a dock, gazebo, firepit area, and five garages. Solar panels and a whole-house Generac provide convenience and peace of mind. A rare waterfront retreat combining recreation, comfort, and exceptional privacy almost never comes to market - your Demond Pond retreat in waiting ~ Welcome Home!

14 Demond Pond Row, Rutland

Listing courtesy of Listing Agent: Christy E. Gibbs from Listing Office: Gibbs Realty Inc..

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