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$3,379,000
5 Beds ⋅ 8 Baths ⋅ 73486050 MLS
A rare offering, 32 Sears Road stands among Southborough’s most treasured private estates. Your approach is a sweeping drive beneath centuries-old oak trees leading to a distinctive port-cochere & stately columned portico. This iconic Georgian Colonial presides over 7.4 magnificent acres adjacent to 25 acres of protected conservation land. The slate roof, balanced symmetry, and meticulously crafted millwork define nearly 8800 sq ft of curated living space. A grand two 2-story marble foyer opens to elegant formal rooms, while the chef’s kitchen leads to exceptional casual living spaces. An exquisite primary suite with limestone fireplace & new luxe bath offers views of the grounds that feature multiple terraces, a resort-like pool & spa, tennis court and brilliant sunsets. Enjoy a sauna after your workout in the upstairs gym or a visit to the wine cellar in the impressive lower-level recreation rooms. Located just 1 mile to Fay & St. Mark’s private schools and 25 miles to Boston.

32 Sears Road, Southborough

Listing courtesy of Listing Agent: Ginny Martins from Listing Office: Ginny Martins & Associates.
$4,500,000
6 Beds ⋅ 8 Baths ⋅ 73481194 MLS
Newly refreshed English Country Estate ready to be discovered! Recently enhanced with a sophisticated neutral palette, this extraordinary 9,300+ sq ft residence is privately sited on 4.5 magnificent acres at the crown of one of Southborough’s most distinguished estate neighborhoods. Surrounded by 180 acres of conservation land, the home offers exceptional privacy, architectural distinction and timeless craftsmanship. Grand formal rooms with exquisite millwork flow to inviting everyday living spaces, while seven gas fireplaces create unexpected warmth throughout. Six bedrooms include a luxurious primary suite with dual spa baths and magnificent sunset views. Resort-style grounds feature multiple terraces, a heated freeform pool, formal English gardens, sculpted hedges, perennial blooms and a flourishing apple orchard with working cider press. An irreplaceable private estate setting just one mile from Fay and St. Mark’s Schools and 25 miles from downtown Boston.

12 Wyndemere Drive, Southborough

Listing courtesy of Listing Agent: Ginny Martins from Listing Office: Ginny Martins & Associates.
$3,795,000
5 Beds ⋅ 6 Baths ⋅ 73470657 MLS
Perfectly sited on nearly 15 acres of gently rolling land, this 2015 contemporary masterpiece blends architectural elegance with natural serenity. Panoramic views in every direction invite a lifestyle of quiet reflection, gentleman farming, or equestrian pursuits, all in a remarkably private yet connected setting. Inside, soaring walls of glass flood the open-concept living, dining, and entertaining spaces with natural light. A state-of-the-art chef’s kitchen with premium appliances and sleek finishes opens to an open staircase leading to five spacious bedrooms including a tranquil primary retreat. Exceptional materials and craftsmanship deliver modern sophistication with timeless appeal. Effortless indoor-outdoor living includes a pool, fire pit, and sweeping grounds. A heated barn provides flexible space for car collections, a workshop or studio. Set in a welcoming neighborhood, minutes to commuting routes, this rare offering unites nature, community, solitude and style!

9A Ashley Road, Southborough

Listing courtesy of Listing Agent: The Ridick Revis Group from Listing Office: Compass.
$2,150,000
4 Beds ⋅ 5 Baths ⋅ 73469164 MLS
Welcome to this stunning four-bedroom single-family home, offering exceptional flexibility with primary suites on both the first and second floors. The thoughtfully designed open floor plan seamlessly connects the living spaces, ideal for everyday living and entertaining. Five well-appointed bathrooms, a spacious two-car garage, and a charming three-season porch enhance both comfort and functionality. Located within a well-managed condominium community due to a shared septic system, this home provides exclusive use of its own private exclusive yard area of over .39 acres. Enjoy maintained common areas, including a large maintained grass area for shared use and a private path that allows direct access to the Sudbury Reservoir trail. This rare opportunity offers the perfect balance of privacy, convenience, and low-maintenance living.

24 Meadow Lane, Southborough

Listing courtesy of Listing Agent: Samantha Poutre from Listing Office: Mathieu Newton Sotheby's International Realty.
$2,600,000
4 Beds ⋅ 5 Baths ⋅ 73466216 MLS
Put your mark on a dream home by Southborough’s premier builder. This new construction home combines a sleek, open-concept design with the exquisite craftsmanship expected at this level. A grand two-story foyer leads to a gourmet kitchen featuring custom inset cabinetry, Quartz countertops, and an oversized social island. The family room, anchored by a modern fireplace, creates a sophisticated yet warm gathering spot.The thoughtful first-floor layout includes both a private Study and a Home Office, each with an adjacent bath. Upstairs, the primary suite serves as a serene retreat with a boutique-style walk-in closet and spa bath. The unfinished basement offers soaring ceilings—ideal for a golf simulator or gym. Set on a rare, flat cul-de-sac lot, you’ll enjoy a private yard with easy access to the MBTA, Boston/Worcester routes, and Breakneck Hill trails. Experience Southborough’s top-rated schools and refined tranquility. Photos are of similar homes; early-stage buyers may customize.

10 Lorenzo Drive, Southborough

Listing courtesy of Listing Agent: Maria Romero Vagnini from Listing Office: Mathieu Newton Sotheby's International Realty.
$5,895,000
7 Beds ⋅ 9 Baths ⋅ 73384674 MLS
Tucked away on one of Southborough’s most coveted cul-de-sacs, 14 Lovers Lane is a breathtaking custom-built estate that redefines luxury living. Crafted with the highest standards and attention to detail, the home showcases timeless architectural design and exquisite millwork throughout. From the grand foyer with soaring ceilings to the richly appointed formal rooms, every space is thoughtfully curated to impress and inspire. The heart of the home is a spectacular chef’s kitchen with top-of-the-line appliances, custom cabinetry, and a sunlit breakfast nook overlooking the grounds. The adjoining family room—with its stone fireplace and coffered ceiling—invites connection and relaxation. Outside, the grounds offer a tranquil and elegant backdrop for everyday living, with a bluestone patio, outdoor kitchen, and covered veranda that seamlessly extend the living space into nature. Each detail is thoughtfully chosen to enhance comfort, functionality, and timeless design.

14 Lovers Lane, Southborough

Listing courtesy of Listing Agent: Gina Anderson from Listing Office: MGS Group Real Estate LTD.

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