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

$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

$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

$255,000

2 Beds ⋅ 1 Baths ⋅ 73553859 MLS

Home being sold AS IS. Discover the charm of peaceful pond community living in this inviting water-view bungalow nestled in one of Rutland's most picturesque settings. Whether you're searching for a year-round home, weekend retreat, or investment opportunity, this 2-bedroom, 1-bath cottage offers incredible potential in a beautiful natural setting.Situated on a level, landscaped lot with mature plantings, established garden space, and plenty of room to relax or entertain, the property invites you to enjoy the outdoors in every season.Title V is done. A brand-new deck provides the perfect place to take in the water views, enjoy your morning coffee, or unwind after a long day. Gather around the fire pit on cool evenings or make use of the spacious yard for gardening and recreation.Inside, the spacious living room is centered around a cozy wood stove, creating a warm and welcoming atmosphere. A bright, flexible bonus room offers endless possibilities as a home office, guest room, hobby space, or potential third bedroom.Additional features include a covered carport, a multi-room shed with electricity ideal for a workshop or extra storage, and easy access to the community beach where you can enjoy swimming, fishing, kayaking, and other seasonal recreation.Conveniently located just minutes from Rutland Center and Holden, this home is surrounded by some of Central Massachusetts' best outdoor destinations, including state parks, hiking and biking trails, campgrounds, conservation areas, and local parks. You'll also appreciate the close proximity to area colleges and universities, with downtown Worcester and Worcester Regional Airport just 15 minutes away, offering the perfect balance of peaceful country living and everyday convenience.Bring your vision and make this charming water-view property your own!

7 Victoria Avenue, Rutland

$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

$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

$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

$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

$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

$674,900

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

$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

$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

$649,900

3 Beds ⋅ 3 Baths ⋅ 73546859 MLS

Beautiful cul de sac location is where your next home is located . This well cared for 3 bed room colonial style home featuring 24 x 24 family room with cathedral ceilings, hdwd floors added in 2025, wood burning fireplace with insert for your convenience ready to accommodate all your entertaining needs. Open to casual dining area in the maple kitchen with center island , granite counters and stainless steel appliances , formal dining room or den and separate office all with hardwood floors offering a versatile floor plan. Second floor has 3 generous size bedrooms all with hardwood flooring added in 2023 including the primary suite where you will find the private bath , and custom built floor to ceiling wardrobe . All bathrooms offer tile flooring and linen closets. Lower level has a finished room perfect for a game or play room. Outside space offers a level back yard with a fenced area, and oversized deck . Solar panels to be assumes with no monthly fees or PPA plus EV charger equipped in the 2 car garage .

9 Cameron Drive, Rutland

Start Your Search

IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but is not guaranteed. © 2026 State-Wide Multiple Listing Service. All rights reserved. Data Last Updated:

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.