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$479,900
3 Beds ⋅ 2 Baths ⋅ 73565251 MLS
Welcome to 587 Main St in Boylston! Set on almost 3 acres, this charming 3-bedroom, 1.5-bath Gambrel offers a wonderful combination of character, space and privacy. Step inside to a warm and inviting interior where wood flooring, natural woodwork and abundant natural light add to the home's classic appeal. The flexible first-floor layout provides plenty of room to spread out, with separate living, dining and family rooms that offer options for everyday living, entertaining or working from home.The spacious kitchen features a vaulted ceiling with skylights, abundant cabinetry, recessed lighting, wood flooring and a dining area. A wood/pellet stove adds warmth and character to the main living space, while large windows throughout the home bring in views of the surrounding greenery. The first floor also includes a full bath with double vanity, tub and shower. Upstairs you'll find three bedrooms with wood flooring and closets, along with a convenient half bath.Outside is where this property truly stands out. Nearly 3 acres offer a beautiful mix of open lawn and wooded surroundings, creating plenty of space to garden, entertain, enjoy outdoor activities or simply relax and appreciate the setting. A detached garage provides parking, storage and additional usable space, complemented by a separate storage shed. The property also offers generous off-street parking.Additional features include a tankless hot water system, insulated windows, generator connection and a partial basement with interior and exterior access. A brand-new septic system is being installed prior to closing, offering an important improvement for the next owner.Conveniently located on Route 70, less than a mile from Route 140, with access to nearby parks, walking and jogging trails, conservation areas and local amenities. If you've been looking for a home with character, flexible living space and acreage in Boylston, 587 Main St is ready to welcome its next owner.

587 Main St, Boylston

Listing courtesy of Listing Agent: Jennifer Roux from Listing Office: Castinetti Realty Group.
$365,000
2 Beds ⋅ 2 Baths ⋅ 73562401 MLS
Welcome to Timberbrook! Within this comfortable and quiet Condo there are two bedrooms with a bonus room for an office or extra space. Open concept living room and dining room. All Appliances to remain. Updates include upstairs vanity sink, toilet, new plumbing, New stove, dishwasher, sink, and floor. New furnace and hot water heater.(2024) Freshly painted throughout. Balcony off of primary bedroom. There is a dedicated garage space ensures secure parking and provides practical storage solutions for personal belongings. Sun streamed tranquil unit, set back from the road with no through traffic. Washer and dryer remain.

506 Edgebrook Dr Unit 506, Boylston

Listing courtesy of Listing Agent: Linette Chalifoux from Listing Office: Walsh and Associates Real Estate.
$1,895,000
3 Beds ⋅ 4 Baths ⋅ 73559080 MLS
Artistry & perfection describes this Italianate Executive Ranch offering a craftsman's dream. Complete custom build with upgrades & details throughout. Welcome to 317 Linden St Boylston offered on the market for the 1st time ever. Sitting distinguishly back from the road, atop a knoll giving a majestic appearance! Beginning from the exterior of brick & copper facia to the grandiose Piazza of white columns creating a refined and timeless entrance. Step into the marbled foyer of pillars, dental molding and extra wide arched doorways. To the left is a formal LR with custom mantled FP, raised panel that flows seamlessly into the formal dining room with a stunning chandelier, behind the glass atrium doors where extraordinary cuisine is served and memorable moments are cherished! Custom "Tuscan Feel" kitchen is every chefs dream. Offering custom cabinets/pullouts w/double slides, granite, tumbled marble backsplash, built in butcher block & sub-zero appliances. Relax & entertain in the wood cathedral ceiling game room w/a grand fieldstone fireplace & masculine "scribed" log mantle, a custom cabinet wet bar & lighted curio wine chiller cabinet. A separate family room with a wall of glass leading to the casual private patio. The Primary En-Suite has a built-in armoire, 2 walk-in closets w/a full bath that sooths the soul and relaxes the body in the soaking tub, hosting a vanity with double sink & walk in double head shower. Additional BR's offer space & large walk-in closets. The "2nd" floor BONUS can function as a guest, media or playroom! Gleaming hardwood/tile throughout. YOU'LL LOVE ENTERTAINING in your own "one if a kind" private oasis in the Roman Style pool house 45'x25' with stucco cathedral ceiling & walls, exposed beams, custom built wood doors, custom kitchen with concrete countertops, fence posts/flooring and a full bath/changing room. The pool house stamped concrete patio balcony overlooks the refreshing "Roman Style" "spa like" heated pool approximately 40'x20'. Central A/C, Buderous Heating system. Professional landscaping includes irrigation, brick patio and cobblestone walkway. Situated on 10.15 acres bordered by Wachusett Reservoir Conservation Area on 3 sides. New roof & new paved driveway. 42'x28' heated 3 car garage, 1 garage under & 1 det'd garage. A Commuters dream, close to Rt 117, 290,495, 140 & 12.

317 Linden St, Boylston

Listing courtesy of Listing Agent: Donna Warfield from Listing Office: RE/MAX Vision.
$1,195,000
73550201 MLS
Some properties preserve history. Others offer possibilities. This extraordinary c.1700 Georgian Colonial offers both. Beautifully restored and privately set on approximately 7 acres of open pasture, mature woodland, and scenic countryside, this remarkable estate blends timeless character with exceptional versatility. The property includes a separate two-family residence, classic barns, and two surveyed and approved building lots, creating outstanding opportunities for agricultural enterprise, multigenerational living, rental income, and future potential. Whether envisioned as a treasured family estate, an agricultural venture, or a legacy investment, this is a rare opportunity to own one of Boylston's most distinctive properties, just minutes from Worcester, major commuter routes, shopping, and everyday conveniences. See property possibilities attachment.

183 Main St, Boylston

Listing courtesy of Listing Agent: Joe Teceno from Listing Office: Mathieu Newton Sotheby's International Realty.
$1,195,000
2 Beds ⋅ 2 Baths ⋅ 73550182 MLS
7 acres of open pasture, mature woodland, and scenic countryside, this property includes a 3334 sf SF home & a separate two-family residence, classic barns, and two surveyed and approved building lots, creating outstanding opportunities for agricultural enterprise, multigenerational living, rental income, and future potential. Whether envisioned as a treasured family estate, an agricultural venture, or a legacy investment, this is a rare opportunity to own one of Boylston's most unique properties, just minutes from Worcester, major commuter routes, shopping, and everyday conveniences. See property possibilities attachment.

183 Main St, Boylston

Listing courtesy of Listing Agent: Joe Teceno from Listing Office: Mathieu Newton Sotheby's International Realty.
$1,195,000
73550127 MLS
Zoned VB, Village Business. Approximately 7 acres of open pasture, mature woodland, and scenic countryside. The property includes a single family & a separate two-family residence, classic barns, and two surveyed and approved building lots, creating outstanding opportunities for agricultural enterprise, multigenerational living, rental income, and future potential. Whether envisioned as a treasured family estate, an agricultural venture, or a legacy investment, this is a rare opportunity to own one of Boylston's most distinctive properties, just minutes from Worcester, major commuter routes, shopping, and everyday conveniences. See property possibilities attachment.

183 Main St, Boylston

Listing courtesy of Listing Agent: Joe Teceno from Listing Office: Mathieu Newton Sotheby's International Realty.
$1,195,000
4 Beds ⋅ 2 Baths ⋅ 73544294 MLS
Some properties preserve history. Others offer possibilities. This extraordinary c.1700 Georgian Colonial offers both. Beautifully restored and privately set on approximately 7 acres of open pasture, mature woodland, and scenic countryside, this remarkable estate blends timeless character with exceptional versatility. The property includes a separate two-family residence, classic barns, and two surveyed and approved building lots, creating outstanding opportunities for agricultural enterprise, multigenerational living, rental income, and future potential. Whether envisioned as a treasured family estate, an agricultural venture, or a legacy investment, this is a rare opportunity to own one of Boylston's most distinctive properties, just minutes from Worcester, major commuter routes, shopping, and everyday conveniences. See property possibilities attachment.

183 Main St, Boylston

Listing courtesy of Listing Agent: Joe Teceno from Listing Office: Mathieu Newton Sotheby's International Realty.
$650,000
3 Beds ⋅ 3 Baths ⋅ 73543497 MLS
Split level home. Front windows replaced 1 year ago. Septic is 11 years old; roof is 15 years old. Back Yard fenced in w/ fenced in Garden. 16X36 inground pool w/ 4 year old Sand filter.

401 Cross St, Boylston

Listing courtesy of Listing Agent: Dave White from Listing Office: OwnerEntry.com.
$575,000
73537276 MLS
STUNNING VIEWS from this coveted lot atop Barnard Hill! Build your dream home at Barnard Hill Estates - a new construction development near the Boylston/Shrewsbury line! Experience luxury living in a charming New England neighborhood setting. Plenty of architectural detail and quality workmanship on our fine Craftsman style homes from which you can choose a style that best suits your needs or bring your own plans or builder. Customize any and all features to your specifications. Private, estate size lot in an idyllic natural setting. Conveniently located in the cozy town of Boylston with easy access to major highways (290, 495, and Mass Pike). Barnard Hill is THEE neighborhood to be in of newly constructed homes with an added bonus of hilltop views!

Lot 52A Barnard Hill Road, Boylston

Listing courtesy of Listing Agent: Collins Team from Listing Office: Collins & Demac Real Estate.
$2,590,000
4 Beds ⋅ 5 Baths ⋅ 73530426 MLS
Minutes from I-495 and I-290 — Boston within reach, Logan Airport within the hour — this award-winning Masiello-designed contemporary residence offers architectural privacy without sacrificing access. Privately positioned on 4.46 acres bordering a private golf course, it merges modern midcentury architecture with Asian-inspired interiors and landscapes by Zen Associates. Dramatic walls of glass, premium black aluminum-clad wood window and door systems, custom walnut millwork, and remarkable sightlines throughout. A waterfall-edge island kitchen with custom cabinetry and premium appliances connects seamlessly to the dining and living spaces. Four bedrooms, an elevator servicing all levels, whole-house shading, and exceptional indoor-outdoor flow. Expansive terraces, covered outdoor living, curated stonework, specimen landscaping, and direct golf course views create a private retreat that balances seclusion with connectivity.

5 Redwood Cir, Boylston

Listing courtesy of Listing Agent: Michael Carucci from Listing Office: Serhant.
$995,000
3 Beds ⋅ 3 Baths ⋅ 73524713 MLS
A rare and distinctive antique residence on 2+ private acres in one of Boylston’s most sought-after neighborhoods. Originally built in the 1700s and relocated in 1975, the home blends historic charm with thoughtful updates, including a Buderus heating system (2022), fully replaced septic (2019), and brand new circular driveway (2024). Features include hard-pine floors, latchkey doors, four interior brick fireplaces, and a kitchen with a Jøtul wood stove. The expanded first-floor layout offers multiple gathering & living spaces, including an all-glass heated sunroom, and excellent flow for entertaining. The second floor has a primary suite with a walk-in closet, full bath, and jacuzzi tub. There are also two additional large bedrooms, another full bathroom and a versatile sitting or second office area(bonus room). Outdoors, enjoy a new patio (2025), underground sprinklers, and beautifully maintained grounds. Private setting with underground utilities and convenient highway access.

9 Bay Path Dr, Boylston

Listing courtesy of Listing Agent: Jackie Cohen from Listing Office: Coldwell Banker Realty - Worcester.
$1,150,000
4 Beds ⋅ 3 Baths ⋅ 73517991 MLS
Welcome to Barnand Hill Estates-Custom home built in 2022 offering the perfect blend of luxury, modern design & energy-efficient construction. Privately situated on a scenic lot, this property showcases high-end finishes, thoughtful upgrades & sophisticated living spaces throughout.The stunning chef’s kitchen is the centerpiece of the home, featuring premium Fisher & Paykel appliances incl. a propane 6-burner rangetop, double wall ovens, microwave drawer & integrated 48” refrigerator/freezer. Quartz countertops extend throughout the kitchen, coffee bar & all bathrooms, complementing the home’s sleek & timeless aesthetic. Designed for both comfort & style, the home features all solid hardwood flooring & bathrooms are finished with elegant porcelain tile. Conveniently located near major commuter routes including I-290 & I-495, yet surrounded by the charm & tranquility of Boylston,this turnkey property offers modern luxury living in one of Central Massachusetts’ most desirable communities

1 Perry Road, Boylston

Listing courtesy of Listing Agent: Marina Kotlyar from Listing Office: RE/MAX Vision.
$1,698,900
4 Beds ⋅ 4 Baths ⋅ 73476118 MLS
Now selling the final phase at Barnard Hill Estates, with limited opportunities remaining in this established neighborhood. Set among natural surroundings yet conveniently located near major routes, shopping, dining, and local schools, this community offers an ideal balance of privacy and accessibility. Built by premier local custom builder Sander Properties, this new construction home offers 4BR and 3.5BA with a thoughtfully designed open-concept layout. The first floor features a private study, a spacious family room with fireplace, and a large kitchen with center island, quartz countertops, and Dacor appliances—seamlessly open to the living area for easy everyday living and entertaining. A mudroom off the garage adds convenience, while a deck off the family room extends the living space outdoors. An unfinished walk-out lower level provides excellent potential for future expansion and or can still be finished prior to closing. Schedule your preview today!

Lot 49 Barnard Hill Road, Boylston

Listing courtesy of Listing Agent: Janice Dumont from Listing Office: JD Advisors, Inc.
$1,675,000
4 Beds ⋅ 4 Baths ⋅ 73470812 MLS
STUNNING VIEWS from this coveted lot atop Barnard Hill! Dream home to-be-built awaits at Barnard Hill Estates - a new construction development near the Boylston/Shrewsbury line! Experience luxury living in a charming New England neighborhood setting. Plenty of architectural detail and quality workmanship on our fine Craftsman style homes from which you can choose a style that best suits your needs or bring your own plans. Featuring open floor plan, hardwood floors, granite counters, wainscoting, central air, 2x6 construction, and extremely energy efficient are just some of the upscale amenities and features of our 4 bedroom, 3 1/2 bath home. Customize any and all features to your specifications. Private, estate size lot in an idyllic natural setting. Conveniently located in the cozy town of Boylston with easy access to major highways (290, 495, and Mass Pike). Barnard Hill is THEE neighborhood to be in of newly constructed homes with an added bonus of spectacular views!

Lot 52 Barnard Hill Road, Boylston

Listing courtesy of Listing Agent: Collins Team from Listing Office: Collins & Demac Real Estate.
$750,000
3 Beds ⋅ 3 Baths ⋅ 73438238 MLS
NEW ConstructionNEW Duplex with 3 BedroomsMaster Bedroom on the 1st floorSpacious Open Floor PlanSpacious Yard.Quality and High Efficiancy.Photo and Video of Model.

291 Sewall St Unit 291, Boylston

Listing courtesy of Listing Agent: Barbara Venincasa from Listing Office: Casa Realty Service.
$735,000
3 Beds ⋅ 3 Baths ⋅ 73438228 MLS
NEW Construction. NEW Duplex with 3 BedroomsSpacious Floor Plan and Spacious Yard.High Efficiency and Quality MaterialsPhoto and Video of Model

289 Sewall St Unit 289, Boylston

Listing courtesy of Listing Agent: Barbara Venincasa from Listing Office: Casa Realty Service.

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