Rutland Homes with Colonial Style

Welcome to Rutland, Massachusetts—a charming town nestled in the heart of Worcester County, where the beauty of New England meets a close-knit community vibe. Known for its picturesque landscapes and rich history, Rutland offers residents a tranquil lifestyle while being just a stone's throw away from the bustling cities of Worcester and Boston. With its rolling hills, serene lakes, and expansive parks, Rutland is perfect for outdoor enthusiasts and families alike.

One of the standout features of Rutland is its stunning collection of Colonial-style homes. These properties are not just houses; they are a piece of history, reflecting the architectural elegance of the 18th and 19th centuries. Characterized by their symmetrical facades, grand entrances, and intricate woodwork, Colonial homes in Rutland exude charm and sophistication. Imagine walking through spacious living areas adorned with classic fireplaces, enjoying the warmth of a home that has stood the test of time.

Living in a Colonial-style home in Rutland means embracing a lifestyle of comfort and tradition. Many of these homes come with expansive yards, perfect for gardening, family gatherings, or simply enjoying the serene surroundings. The community spirit is palpable, with local events and friendly neighbors making Rutland feel like home.

Whether you’re a first-time buyer or looking to settle down in a peaceful environment, Rutland's Colonial homes offer a unique blend of history, style, and community. Discover the charm of Rutland and make it your home today!

Newest Rutland Homes with Colonial Style

$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.

$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..

$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.

$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.

$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

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

$1,185,000

3 Beds ⋅ 3 Baths ⋅ 73546321 MLS

Some homes are simply lived in. This one is experienced. Hidden beyond a winding, tree-lined drive, this extraordinary 20-acre estate borders more than 50 acres of protected conservation land with direct access to the Massachusetts Rail Trail, offering a setting that feels worlds away, yet remains convenient. Reimagined through an investment exceeding $1 million, every space has been thoughtfully curated with timeless architecture, designer finishes, white oak flooring, professional landscaping, a dramatic two-sided fireplace, and a chef’s kitchen featuring Viking and Thermador appliances. Outside, a private resort unfolds with a saltwater pool, cascading rock waterfall, brand-new hot tub, outdoor kitchen, fireplace, and breathtaking landscape lighting that transforms the property after sunset. Homes offering this level of privacy, luxury, and lifestyle rarely become available—and photos simply cannot capture the experience. Additional premium features available.

350 Main Street, Rutland

Listing courtesy of Listing Agent: Kaitlyn Flynn from Listing Office: The Neighborhood Realty Group.

$665,000

3 Beds ⋅ 3 Baths ⋅ 73543945 MLS

Welcome to 2 Madisyn Avenue in Rutland! This lovely 3-bedroom, 2.5-bath young Colonial is situated on a beautiful, level 1.5-acre lot in one of Rutland's most desirable neighborhoods. The home features a dramatic vaulted great room with a fireplace, creating a warm and inviting gathering space. The open-concept kitchen offers granite countertops, a center island, and sliding glass doors leading to the deck, perfect for entertaining or enjoying the beautifully maintained serene backyard. The main level also includes a formal dining room, a versatile den, convenient first-floor laundry, and a 1/2 bath. Upstairs, the spacious primary suite features a vaulted ceiling, walk-in closet, and private full bath. The two additional bedrooms and another full bath provide plenty of room for family or guests. With its thoughtful layout, large irrigated private yard, 2-car garage and oversized driveway, and sought-after location, this home offers the perfect combination of comfort and functionality

2 Madisyn Ave, Rutland

Listing courtesy of Listing Agent: Steve Sterczala from Listing Office: The O'Rourke Group Real Estate Professionals.

$689,900

4 Beds ⋅ 3 Baths ⋅ 73539074 MLS

Custom built Colonial home with open floor plan on 2+ acre lot is now available for new owners. The cobblestone walkway welcomes you to the farmers porch and into your new home where you will find the spacious front to back living room with hardwood floors open to kitchen with maple cabinetry, granite counters and tile flooring. Nice size dining room perfect for holiday gatherings. Second floor has 4 generous size bedroom including the primary suite with massive closet and private bath . All bathrooms have tile flooring and granite counters. Lower level is fully finished with 3 additional rooms making this home over 3000 sq ft. Outside bonuses include an above ground pool, storage shed , English gardens and natural ledge backdrop. You don't want to miss this one !

248 Pleasantdale Road, Rutland

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

$519,900

3 Beds ⋅ 2 Baths ⋅ 73528910 MLS

Set on a beautifully wooded lot, 57 Sassawanna Rd in Rutland is an inviting 3-bedroom, 1.5-bath Saltbox Colonial that offers both privacy and charm. The first floor features an updated kitchen with stainless steel appliances, ample cabinetry, and stunning exposed wood beams that add character to the space. A cozy living area with a wood-burning stove set on a classic brick hearth flows seamlessly into the dining room with wainscoting. This level also includes a spacious bedroom and an updated full bath. Upstairs, you’ll find two large, equally sized bedrooms, a comfortable family room, and a convenient half bath. Just off the kitchen, a spacious composite deck provides the perfect setting for outdoor dining, gatherings, or relaxing while overlooking the peaceful backyard. A one-car garage offers parking and additional storage, while the expansive yard and natural surroundings complete the setting. This home blends comfort, functionality, and a serene Rutland location.

57 Sassawanna Rd, Rutland

Listing courtesy of Listing Agent: Michael Giovangelo from Listing Office: Better Living Real Estate, LLC.

$739,900

4 Beds ⋅ 4 Baths ⋅ 73527706 MLS

In the process of being built.New Construction Spacious Colonial 9 Rooms, 4 bedroom, 3.5 baths. 2 car garage with farmers porch on 1.4-acre lot that backs up to wooded privacy. This new home comes with recessed lighting, vaulted ceiling in the master bedroom, boast triple pane windows, beautiful white painted maple Shaker style cabinets and vanities with white quartz counter tops, stained hardwood flooring and tile bathroom floors throughout, including finished attic bedroom 18x16 and 6x7 1/2 bath and new stackable washer and dryer. Now buyers have a unique opportunity to modify finishes according to their desires such as adding wainscoting trim and crown molding to rooms or stairwells. Occupancy scheduled for Nov. 2026.

41 Irish Lane, Rutland

Listing courtesy of Listing Agent: Michael Buzzotta from Listing Office: Premier Homes Real Estate.

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