Rutland Real Estate

Welcome to Rutland, Massachusetts – a hidden gem nestled in the heart of Worcester County. With its picturesque landscapes, friendly community, and rich history, Rutland offers a unique blend of rural charm and modern convenience, making it an ideal place to call home.

As you explore Rutland, you'll be captivated by its scenic beauty, characterized by rolling hills, lush forests, and tranquil lakes. Outdoor enthusiasts will appreciate the abundance of recreational opportunities available, from hiking and biking in the nearby conservation areas to fishing and kayaking on the serene waters of Rutland State Park. The town’s commitment to preserving its natural surroundings ensures that residents can enjoy the great outdoors year-round.

Rutland boasts a strong sense of community, where neighbors become friends and local events bring everyone together. The town hosts various festivities throughout the year, including farmers' markets, seasonal fairs, and holiday celebrations, fostering a warm and welcoming atmosphere. Families will find excellent educational opportunities with top-rated schools that prioritize student success and community involvement.

Conveniently located just a short drive from Worcester, Rutland offers easy access to urban amenities while maintaining its tranquil, small-town feel. Enjoy shopping, dining, and cultural experiences in nearby cities, then retreat to the peaceful embrace of Rutland at the end of the day.

Whether you’re looking to buy your first home, relocate, or invest in a property, Rutland, MA, presents an inviting opportunity for all. Discover the charm of this vibrant community and make Rutland your next home sweet home!

Newest Listings in Rutland

$389,900

4 Beds ⋅ 2 Baths ⋅ 73557111 MLS

Well-maintained Cape in a neighborhood setting close to the town center! This versatile home offers a flexible floor plan with two bedrooms on each floor, providing options for multigenerational living, guests, or a home office. The first floor offers potential for an in-law suite by expanding the existing half bath, while the second floor includes space to add another bathroom. Enter through the spacious mudroom, which leads to a first-floor bedroom with an adjoining den or sitting room and a full bath. The eat-in kitchen opens to the heart of the home, while the formal dining room and comfortable living room provide plenty of space for everyday living and entertaining. The heated sunroom is sure to become your favorite room, featuring knotty pine walls, walls of windows, and access to the deck overlooking the backyard. A second first-floor bedroom and half bath complete the main level. Upstairs are two additional bedrooms plus a large storage area with the potential to be converted into a second full bath. Outside, enjoy the level, fenced backyard with two storage sheds, offering space for gardening, play, or pets. Recent updates include replacement windows, boiler (2013), and oil tank and hot water tank (2003) Open Houses: Saturday, August 1, 10:00 AM–12:00 PM, and Sunday, August 2, 1:00–3:00 PM.

2 Highland Park Rd., Rutland

Listing courtesy of Listing Agent: Laurie Kraemer from Listing Office: OPEN DOOR Real Estate.

$699,900

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.

$679,900

3 Beds ⋅ 3 Baths ⋅ 73554676 MLS

Welcome home to the lifestyle you've been dreaming of. A home where every detail invites you to slow down, gather often, and enjoy the beauty of every season. Set on 1.5 beautifully landscaped acres, this exceptional 3-bedroom, 3-bath home blends timeless charm with thoughtfully designed spaces for everyday living and effortless entertaining. The heart of the home is a chef-inspired eat-in kitchen featuring a one-of-a-kind island, an abundant workspace, and a seamless flow that leads you to the elegant French doors in your formal dining room, which is perfect for everything from weeknight dinners to holiday gatherings. A carpeted family room with a warm propane fireplace creates an inviting atmosphere you'll love coming home to that overlooks spectacular gardens. Designed with both comfort and convenience in mind, the first-floor laundry is thoughtfully tucked away behind closet doors, adding everyday practicality, while the expansive deck and classic farmer's porch invite you to enjoy the beauty of every season. Outside, stunning perennial gardens provide a colorful backdrop and a peaceful retreat, making the property feel like your own private oasis. This is the kind of home where morning coffee on the porch becomes a daily ritual, lazy Sunday afternoons are spent on your shaded patio relaxing in your hammock with a good book, summer evenings are spent entertaining under the stars and around the fire, and every room tells a story of warmth, quality, and care. A truly special property offering the perfect balance of indoor comfort and outdoor beauty, a place where every season is meant to be enjoyed, and every day feels a little more special.

52 Woodside Ave, Rutland

Listing courtesy of Listing Agent: Tracy LaRosa from Listing Office: Daisy Hill Real Estate and Rentals.

$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..

$624,900

3 Beds ⋅ 3 Baths ⋅ 73551644 MLS

New England Colonial charm meets timeless Pottery Barn style in this beautifully maintained, move-in ready home. Tucked away on a private cul-de-sac in the heart of Rutland, it’s just a short walk to the town center and steps from your own access to the Central Mass Rail Trail. The remodeled kitchen opens to a Trex deck overlooking a peaceful backyard with beautiful landscaping, a patio, a Reeds Ferry shed, and built-in storage below the deck. Inside, you’ll find spacious bedrooms, closet organizers throughout, two fireplaces, including one in the primary bedroom, and a large walk-in closet with a cozy reading or office nook. The finished walk-out Lower Level with a full bath offers guest or in-law potential. Efficient mini-split heating and cooling, new garage doors, and meticulous care throughout make this home truly turnkey ~ Welcome Home

13 Watson Lane, Rutland

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

$169,900

2 Beds ⋅ 1 Baths ⋅ 73550790 MLS

Enjoy the ease of first-floor living in this beautifully maintained 2-bedroom condo located in the highly desirable town of Rutland. This inviting unit offers central air conditioning for year-round comfort, a functional and spacious layout, and low-maintenance living at its finest. The bright living spaces provide a welcoming atmosphere, while the convenient first-floor location eliminates the need for stairs. Nestled in a peaceful community, you’ll appreciate the charm and small-town feel of Rutland while remaining close to local shops, restaurants, parks, and major commuter routes. Whether you’re a first-time buyer, downsizing, or seeking an investment opportunity, this condo is a fantastic place to call home. Schedule a showing today!

176 Maple Ave Unit 7-1, Rutland

Listing courtesy of Listing Agent: Nicholas Solitro from Listing Office: Settlers Realty Group, LLC.

$549,900

4 Beds ⋅ 2 Baths ⋅ 73549923 MLS

Nestled on over 3 private, wooded acres, this classic Colonial with a distinctive gambrel roof offers privacy, charm and exceptional potential. Major improvements provide peace of mind, including a new septic system (2026), new furnace (2026), new oil tank (2026), new chimney liner and inspection (2026), along with a new water heater (2024). The home features 4 bedrooms, 1.5 bathrooms, hardwood flooring in many rooms, and a spacious setting surrounded by mature trees and natural beauty. This property offers the perfect balance of peaceful country living and everyday convenience. Whether you're looking to restore its classic character or create a fresh, updated interior, this is a rare opportunity to own a home with outstanding fundamentals in an exceptional setting. Enjoy nearby hiking trails, parks, and year round outdoor recreation minutes from your doorstep.

46 Prospect St, Rutland

Listing courtesy of Listing Agent: Patty Downing from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.

$419,900

3 Beds ⋅ 2 Baths ⋅ 73549647 MLS

Great Home at great price. Features updated kitchen with granite countertops, new split-duct central AC /Heating system, living room with hardwood floors and fireplace, three bedrooms (two on main floor, one on2nd level), two newly remodeled bathrooms, ready to finish basement with walk-out to patio, 14x19 threeseason porch off kitchen, updated 12x16 backyard deck overlooking private backyard. Workshop shed,fenced in garden. This property abuts over 9+ acres of conservation land ideal for walking trails. New Hotwater tank, new heating system and more.

132 Main St, Rutland

Listing courtesy of Listing Agent: Derek Greene from Listing Office: The Greene Realty Group.

$665,000

4 Beds ⋅ 3 Baths ⋅ 73547470 MLS

This beautiful 4-bedroom, 2 1/2 bath Colonial has so much to offer. The 2-story foyer opens to a Dining Rm on one side & a 14x22 ft Living Rm on the other, currently used as a home office. The spacious eat-in kitchen features professional DCS convection gas stove, gleaming granite counters & recent hardwood flooring. Generous storage including a custom walk-in pantry and oversized kitchen island. 1st flr laundry. Updated 1/2 bath w/ young hardwood flr. The 23x23 ft Great room is perfect for entertaining & features cathedral ceiling, palladium window & gas fireplace. Upstairs are 4 bedrooms . Primary bedroom w/ cathedral ceiling, hardwood, 2 custom closets & upgraded bath. Basement has been partially finished w/ a 16x25 ft bonus room. The tree lined backyard has hot tub, above-ground pool, composite deck. Relax on your Farmer's porch & enjoy the neighborhood views. Bonus: picturesque mountain views from 2nd flr! No showings until Open House Sunday 7/12 11-12:30

35 Brunelle Dr, Rutland

Listing courtesy of Listing Agent: Lisa Westerman from Listing Office: RE/MAX Prof Associates.

$399,900

2 Beds ⋅ 1 Baths ⋅ 73545029 MLS

Investor's Dream or the perfect opportunity to build instant equity! This livable home offers endless potential for buyers with vision looking to renovate while enjoying peaceful country living. Nestled on a spacious lot with backyard trails, this property is ideal for nature lovers while remaining just 10 minutes to Worcester, under 10 minutes to downtown Holden, major routes, state parks, and local colleges. A standout feature is the heated 30x40 barn with a steel roof, 10,000-lb car lift (installed in 2025), storage shelving, and pellet stove—perfect for mechanics, hobbyists, or a home workshop. The home also features a working pellet stove, generator, 3-bedroom septic system,Dehumidifier, air-conditioner ,and a large yard with potential for gardens or hobby farming (subject to local regulations). Seller is including a Cub Cadet riding mower, snowblower, and grill. Located in beautiful Rutland, this is a rare opportunity to create your dream property.

3 Barre Paxton Road, Rutland

Listing courtesy of Listing Agent: Cecelia Powers from Listing Office: RE/MAX Generations.

$669,000

3 Beds ⋅ 2 Baths ⋅ 73546908 MLS

Some homes offer more than a place to live—they offer a way of life. Nestled on 2.21 picturesque acres, this exceptional property blends country charm with modern comfort just minutes from the center of Rutland. Enjoy summer days by the in-ground pool, peaceful mornings surrounded by nature, and the timeless appeal of a classic barn ideal for horses, hobby farming, or extra storage. Inside, you'll find 3 bedrooms, 2 full baths, an updated kitchen, central heat and A/C, and a finished lower level offering flexible space for a family room, home office, gym, or guest area. Paid-off solar panels add exceptional value and energy savings. The expansive grounds provide room to relax, entertain, and embrace the lifestyle you've been dreaming of.

345 Pleasantdale Rd, Rutland

Listing courtesy of Listing Agent: Darcilane Oliveira from Listing Office: The Neighborhood Realty Group.

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