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$3,799,000
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

$4,500,000
6 Beds 8 Baths 73481194 MLS
Welcome to 12 Wyndemere, a breathtaking English Country Manor set on 4.5 acres at the crown of Southborough’s most distinguished estate neighborhoods. Surrounded by 180 acres of conservation land, this 9300+ sq ft residence offers exceptional privacy and timeless presence. Grand formal rooms with handcrafted millwork blend seamlessly with inviting spaces designed for everyday living. Seven gas fireplaces add warmth and charm throughout making the home surprisingly cozy for its scale. The upper level features six bedrooms, including a spacious primary suite with dual baths and magnificent sunset views. The estate’s unparalleled grounds are a masterpiece of landscape design with multiple terraces, brick walkways lined by sculpted hedges, perennial blooms, a flourishing apple orchard with working cider press, a smokehouse, heated freeform swimming pool and a formal English garden for reflection. Only 1 mile to Fay & St. Marks schools and 25 miles to downtown Boston.

12 Wyndemere Drive, Southborough

$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

$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

$850,000
3 Beds 3 Baths 73446670 MLS
Mixed use property: A Single Family Home (2,200 sq. ft.) & Detached Commercial Building (an additional 1,361 sq. ft. built in 1980) on Boston Road, (Route 30) for a total sq.ft. of 3,583 sq. ft. Best of both worlds: Highly visible location for a small Business & large, serene backyard behind home, on 3/4 Acres. The Single Family Ranch Home was added onto & renovated. Some of the additions to the home include: new vinyl siding (2025), updated electric service (2025), Family Rm addition (1982), Screened Porch addition, 3 rooms & full Bath that can be separated w/side entrance. Many upgrades to the home including renovated Kitchen w/granite counters, cabinets & appliances. Living Room floors refinished, new hot water heater, shed. Separate Commercial Building was a printing business for many years "Quikprint" w/additional 1,361 sq.ft. Plenty of parking in spacious driveway. Don't miss this rare opportunity in Southborough- Great location & fantastic visibility for your Business/Office!

216 Boston Rd, Southborough

$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

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