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$1,899,900
4 Beds ⋅ 5 Baths ⋅ 73575459 MLS
Exceptional custom-built home offering sophisticated design, soaring ceilings, walls of glass, and a seamless connection to the beach-entry gunite pool surrounded by your beautiful backyard oasis. The updated modern kitchen features Taj Mahal quartz, marble backsplash, refinished oak flooring, and fresh interior paint. The gas cooktop, pot filler, double ovens and warming drawer are a cook’s delight. The main level offers four flexible bedroom options, including a spacious primary suite with fireplace, built-ins, and walk-in dressing room. A private second-floor guest suite adds versatility. The finished walkout lower level has a universal design accessible by stairs, elevator and sloped walkway from the front of the home. Offering excellent ADU potential with an accessible bath and roll-in shower. Attached garage with step-free entry. Enjoy Southborough’s highly regarded schools and convenient MBTA access.

6 Watkins Ln, Southborough

Listing courtesy of Listing Agent: Jennifer Green Thompson from Listing Office: RE/MAX Signature Properties.
$6,250,000
5 Beds ⋅ 9 Baths ⋅ 73575382 MLS
Once in a lifetime opportunity to own an irreplaceable almost 10 acre estate*One of the area's most desired streets is home for this completely bespoke manor*Meander down the long, sense of arrival driveway past your own spring fed small pond and charming barn setting the stage for understated elegance*Enter the slightly elevated parking court surrounded by granite walls with complete paver entry (partially heated for winter weather) and be impacted by this refined home of exceptional quality built by noted local builder*While being welcoming and inviting, this home is ultra-luxe in every conceivable way without being ostentatious*Impeccable grounds include acres of lush, groomed grass, a tree lined groomed allee creates a visual promenade for the rear of the property and is tastefully and subtly illuminated with abundant landscape lighting*Sumptuous pool area with covered outdoor entertainment pavilion, dressing room, bathroom, outdoor shower and patios with stone walls and metal balusters is set off to the side enjoying privacy and great afternoon sun*This home enjoys remarkable and substantial infrastructure for years of enjoyment*Refined styling is paramount for timeless enjoyment of this unique home*Custom crafted front double doors and custom crafted mahogany garage doors are complemented by subtle sand-colored cut granite and wood shingles all capped by the new wood roof*Multiple rooflines, many bay windows, covered porch and screened porch make this home an architectural masterpiece*1st level enjoys a front-to-back limestone Foyer bisecting the home and creating a sense of flow*Formal rooms are complemented by more casual spaces to provide a feeling of warmth*1st floor enjoys 2 Family Room areas, formal rooms for entertaining, heart-of-the-home Kitchen, substantial mudroom and stunning vaulted, fireplace screened porch*Follow the incredible sweeping staircase to the upper story with the west side for fireplaced Primary suite with two generous, custom WI closets plus a cedar closet, private balcony and truly sumptuous bath*there is also a guest bedroom & bath on this side*The east side of the house is home for two additional bedroom suites, giant well-outfitted study with built-in desk units, large laundry, craft room and wonderful "in-law" or long-term guest suite*Finished walkout lower level has exercise room, spa-bath, large multi-use space and movie theatre*4 car garage*Lit sport court for basketball or pickle ball*Every imaginable upgrade*

31 Sears Rd, Southborough

Listing courtesy of Listing Agent: Andrew Abu from Listing Office: Andrew J. Abu Inc., REALTORS®.
$1,099,900
3 Beds ⋅ 4 Baths ⋅ 73568578 MLS
Welcome to Wedgewood Estates, a highly sought-after Southborough community offering top-rated schools, exceptional commuter access, and a wonderful neighborhood setting. This meticulously maintained and thoughtfully updated home reflects the pride of ownership rarely found in today’s market. The inviting open floor plan features gracious front-to-back living and dining spaces, a private study, and an exceptional kitchen with custom cabinetry, quartz countertops, stainless-steel appliances, and an oversized island that flows seamlessly into the cathedral family room. Upstairs, hardwood floors enhance the spacious primary suite, complete with an expansive walk-in closet, beautifully updated bath, and convenient second-floor laundry. Generously sized additional bedrooms share a tastefully updated bath. The finished lower level provides two flexible spaces currently used as a family room and gym, along with a full bath—ideal for guests, recreation, or a home office. Outside, your private backyard oasis awaits with an in-ground pool and low-maintenance deck, creating the perfect setting for summer entertaining and relaxation. Just steps from highly rated Mary Finn Elementary School, with miles of paved sidewalks and easy access to the MBTA train. Come take a tour and Make Yourself at Home!

26 Wildwood Dr, Southborough

Listing courtesy of Listing Agent: Jennifer Green Thompson from Listing Office: RE/MAX Signature Properties.
$1,199,000
3 Beds ⋅ 4 Baths ⋅ 73568545 MLS
***PRICE ADJUSTMENT***.Don't miss this stunner on scenic & historic Sears Rd! This immaculate spacious home with 2-story foyer, banquet sized DR & 1st floor office.Chef’s kiss dream kitchen featuring Thermador & Bosch appliances incl a warming oven surrounded with windows overlooking private wooded rear yard.Cathedral FR with wood burning fireplace & gallery to 2nd floor opens to one of two decks cleverly sited to enjoy all that nature has to offer as well as gorgeous free form inground pool. 2nd floor features incl spacious primary suite with newer bath ensuite. Two additional bedrooms & full bath complete second floor. Mostly finished walk out basement is ideal for multi-generational living/au pair, etc. Currently used as a bedroom with full bath, slider to rear yard provides wonderful natural light & spacious sitting area is ideal to unwind. Built in bar offers convenience. Additional unfinished space provides plenty of storage.Sears Rd at its finest!

71 Sears Rd, Southborough

Listing courtesy of Listing Agent: Caroline Hanlon from Listing Office: Fireside Real Estate.
$1,300,000
4 Beds ⋅ 4 Baths ⋅ 73553335 MLS
Welcome to 10 Burnett Rd Southborough where comfort and refined living await! The formal living room & dining room lead to the stunning eat-in kitchen - it's a chef's dream to work in with granite countertops, double ovens and stainless appliances. The open floor plan here leads to the family room with vaulted ceilings, skylights & fireplace. The first-floor office with storage, built in bookshelves and French doors complete this floor. The 2nd floor has all 4 large bedrooms- the primary bedroom features a walk-in closet as well as an en-suite bathroom with a large, jetted tub, double vanity and skylights. Laundry is located just down the hall. The beautiful, finished walkout basement adds to your entertainment options and/or workout space or game room- with a refrigerator, sink and microwave and a full bathroom and a sliding door out to the yard. Beyond the interiors of this home, the deck off the kitchen and family room extend to the fabulous outdoor living space with a wonderful heated inground pool, and a covered area of the deck and a pool house for storage. See list of updates and inclusions! So convenient to shopping and major routes.

10 Burnett Road, Southborough

Listing courtesy of Listing Agent: Lydia Rajunas from Listing Office: REMAX Executive Realty.
$975,000
4 Beds ⋅ 3 Baths ⋅ 73552290 MLS
Exceptional 3,000± sq. ft. Farmhouse Colonial with an inviting farmer’s porch, gracefully sited on a sun-filled 1-acre lot surrounded by spectacular perennial gardens. This beautiful 4-bedroom, 2.5-bath home offers a stunning family room w/custom built-ins & fireplace, Entertain in your open kitchen w/ Ctr island, butcher block counters & hardwood floors! Plus a dedicated first-floor office or gym! The cathedral primary suite offers a dressing room & luxurious en suite with soaking tub & separate shower. Enjoy a spacious deck overlooking your private backyard retreat with an inground pool, custom fencing, irrigation, & lush landscaping. New roof (2017), new pool liner (2021), Anderson windows, W/D/Ref incl, new septic distribution box (2026), central air, 2-zone heat, & an expansive lower level ready for future expansion. Minutes to major routes, commuter rail, shopping, dining, & Southborough’s award-winning schools. The perfect home for entertaining family and friends, indoors & out!

162 Main St, Southborough

Listing courtesy of Listing Agent: The Real Estate Ladies Team from Listing Office: REMAX Executive Realty.
$1,994,600
4 Beds ⋅ 5 Baths ⋅ 73547570 MLS
This custom contemporary estate has been fully renovated with over $500k of high end updates! Inside boasts over 7400sqft of living space with a secluded first floor primary suite including an office space, walk in closet and recently renovated full bath with endless storage. The designer chefs kitchen was thoughtfully put together with high end appliances, cabinetry and countertops. The upstairs features 3 additional oversized bedrooms with 2 full baths that just completed renovations. The basement shows as another open living space with huge windows, an exercise room, game area, office space and additional full kitchen with theater space. Your outdoor space is just as fabulous with views of the Sudbury River, an inground heated pool, hot tub with cabana and putting green. A completely renovated ADU building can be utilized for how you see fit. Whether you are a family looking for a quiet retreat or someone that does a lot of entertaining, this breathtaking property has it all.

6 Lynbrook Road, Southborough

Listing courtesy of Listing Agent: Jeffrey Incutto from Listing Office: BA Property & Lifestyle Advisors.
$1,795,000
4 Beds ⋅ 4 Baths ⋅ 73531936 MLS
Resort-style living on 1.03 landscaped acres in Watkins Glen. This 2001 Colonial offers 4 bedrooms, 4 full baths, a 3-car garage, and a heated in-ground pool. The chef’s kitchen opens to living space and a four-season sunroom with walls of windows and a gas fireplace. Formal dining has a coffered ceiling and custom hardwood inlay. A third-floor bonus room plus a walk-out lower level give you office, gym, media, or guest options. Outside: mature rose gardens, stone walls, and a fenced yard. Near commuter routes, Algonquin schools, and trails. Photo digitally enhanced to depict twilight.

2 Watkins Ln, Southborough

Listing courtesy of Listing Agent: Susan Gillis from Listing Office: William Raveis R.E. & Homes Services.
$875,000
4 Beds ⋅ 3 Baths ⋅ 73515804 MLS
Don't let the summer slip by without a visit to 122 Deerfoot Rd! Pool parties. Grilling on the patio. Kids swimming. Drinks on the deck. Quiet dead-end street. Welcome to 122 Deerfoot—a spacious Colonial tucked away on a quiet street in Southborough, where comfortable living and summer entertaining come together beautifully. With approximately 2,750 square feet, four bedrooms, three full baths, and a flexible first-floor bedroom, this home offers plenty of room to spread out. The inviting main level features hardwood floors throughout the living and dining rooms, a generous living room with a charming window seat and wood-burning fireplace, and an updated kitchen with granite countertops, breakfast area, recessed lighting, and direct access to the patio. The family room opens directly to the backyard, creating an easy flow for everyday living and entertaining. And then there's the backyard! Enjoy your own private summer retreat with an inground pool, spacious deck, patio, fenced yard, storage shed, and professional landscaping. Whether you're hosting friends, grilling dinner, or simply relaxing poolside, this outdoor space is designed for making the most of warm-weather days. A first-floor bedroom with custom built-ins and French doors offers excellent flexibility as a guest room, home office, or study. Upstairs, the spacious primary suite features a walk-in closet, private bath, hardwood flooring, and a private balcony overlooking the backyard. Two additional generously sized bedrooms, a dedicated office/craft space, and convenient second-floor laundry complete the upper level. Additional highlights include central vacuum, a full unfinished basement for storage or future possibilities, private water and sewer, a paved driveway with parking for six, and a 0.75-acre lot. Location adds even more appeal, with Finn School nearby and conservation land with walking trails at the end of the street, offering easy access to nature and outdoor recreation right from the neighborhood. Set on a quiet public road while still convenient to shopping, schools, golf, medical facilities, and major routes, this is a home with space, flexibility, and a backyard you'll look forward to enjoying all summer long.

122 Deerfoot Rd, Southborough

Listing courtesy of Listing Agent: Sue Gordon from Listing Office: Castinetti Realty Group.
$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.

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