Southborough Homes for Sale

Welcome to Southborough, Massachusetts—a hidden gem nestled in the heart of Worcester County. This charming town seamlessly blends rich history with modern conveniences, making it an ideal place to call home. With its picturesque landscapes, vibrant community spirit, and top-rated schools, Southborough offers a serene suburban lifestyle that appeals to families, professionals, and retirees alike.

Founded in 1727, Southborough is steeped in history, boasting beautifully preserved colonial architecture and a quaint town center that invites leisurely strolls. Nature enthusiasts will appreciate the expansive trails and parks, including the stunning Sudbury Reservoir and the lush conservation areas that provide endless opportunities for hiking, biking, and outdoor recreation.

As you explore the real estate market in Southborough, you’ll discover a diverse selection of homes for sale. From charming single-family residences to spacious modern builds, there’s something to suit every taste and budget. Many properties offer generous yards, ideal for family gatherings or peaceful evenings under the stars. The town’s commitment to maintaining a friendly, tight-knit community atmosphere is evident in its local events and gatherings, fostering connections among neighbors.

Southborough's prime location also offers easy access to major highways and nearby commuter rail stations, making it a convenient choice for those who work in Boston or Worcester. With its delightful blend of tranquility, community, and accessibility, Southborough is not just a place to live—it's a place to thrive. Discover your dream home in this enchanting town today!

Newest Southborough Homes for Sale

$2,599,000

4 Beds ⋅ 7 Baths ⋅ 73601171 MLS

Tucked away on picturesque Sears Road, one of Southborough's most coveted addresses, this extraordinary custom-built home offers a rare blend of timeless elegance, exceptional craftsmanship & private natural beauty*Set atop a private parcel overlooking lower Sears Rd, the home makes a striking first impression as you pass through its stately stone pillars & arrive at the welcoming portico*Beyond the double-door entry, a magnificent two-story Foyer sets the tone, showcasing a curved wrought iron staircase, antique marble flooring, exquisite millwork, and raised-panel wainscoting*Designed for both grand entertaining & comfortable living, the home features an exceptional floor plan filled with natural light, with soaring 10-foot ceilings throughout much of the main level, and 9-foot ceilings on most of the second floor & lower level*The heart of the home is a beautifully appointed Chef's Kitchen with an oversized island & abundant custom cabinetry, premium appliances, & WI pantry*Gathering spaces flow effortlessly, including a vaulted Family Room anchored by a dramatic floor-to-ceiling stacked stone fireplace & expansive patio doors that open to an oversized IPE deck, screened porch, and exterior fireplace that overlook the beautifully landscaped private courtyard*The Dining Room offers built-in cabinetry, and impressive butler’s pantry & direct access to a south-facing covered veranda while a gracious Living Room provides the perfect setting for quiet conversation or a library*A cherry-paneled Office with custom built-ins creates an inspiring workspace*A first-floor Guest Suite with private entrance and bath offers ideal accommodations for visitors, in-law, or multigenerational living*Upstairs the luxurious Primary Suite serves as a peaceful retreat featuring sun-filled eastern exposures, a spa-like Master Bath & a custom WI closet*Each additional Bedroom enjoys its own Private Bath & distinctive architectural character *A spectacular 2-level Great Room with cherry floors, wet bar, billiards, and a Juliet balcony with valley views offers endless possibilities for recreation & entertaining*The walk-out lower level offers an Entertainment Kitchen, Media & Game spaces, full Bath, Wine Cellar, and access to the lower lawn*Adjacent to the property, enjoy a jog or casual walk on more than 20 acres of trails*This private sanctuary is designed for memorable gatherings, everyday comfort & a lifetime of enjoyment.

56 Sears Rd, Southborough

Listing courtesy of Listing Agent: Andrew Abu from Listing Office: Andrew J. Abu Inc., REALTORS®.

$1,990,000

4 Beds ⋅ 4 Baths ⋅ 73598580 MLS

What if weekends meant morning walks at nearby Hopkinton State Park, afternoons kayaking or fishing, and evenings by your own backyard fire pit? Tucked on a cul-de-sac in Southborough's Liberty Estates, this Colonial offers wooded privacy with easy access to Ashland commuter rail, the Mass Pike and Route 9. Inside, living and dining rooms lead to a fireplaced family room and kitchen with granite counters, a generous island and Sub-Zero, Bosch and Electrolux appliances. A first-floor office features custom built-ins. Upstairs, the primary suite offers two California walk-in closets, a cathedral ceiling and a bath with soaking tub and separate shower; a bonus room adds flexibility. The finished walk-out lower level includes a fireplace, kitchenette and full bath with steam shower. At home, enjoy a heated gunite pool with rock waterfall, spa, composite deck and fenced yard. A three-car garage and whole-house generator round out the house.

9 Wentworth Drive, Southborough

Listing courtesy of Listing Agent: Lilia R. Flores from Listing Office: Barrett Sotheby's International Realty.

$650,000

3 Beds ⋅ 2 Baths ⋅ 73594316 MLS

PRICE IMPROVEMENT! Set on 3.8 acres in Southborough, this historic home pairs timeless character with thoughtful updates. A previous owner expanded the original footprint, creating additional living space while preserving the home’s distinctive charm. Hardwood floors in the primary bedroom, living room, and dining room add warmth and character. The kitchen features appliances less than two years old, and the kitchen and laundry room windows were replaced in 2022. The upstairs bathroom was fully renovated in 2024. Brand New Septic System was installed on November 6, 2026. Updated in 2021, the enclosed second-floor porch offers flexible bonus space for a home office, hobbies, or relaxation. Other Recent improvements include a NEW Buderus Heating System, New Roof installed in 2019, Siding installed in 2020, and gutters installed approximately three to four years ago. With two off-street parking spaces and 3.8 acres to enjoy, this property offers a distinctive blend of historic appeal, updated amenities, and a spacious setting.

8 Pearl Street, Southborough

Listing courtesy of Listing Agent: Ashley Brunner from Listing Office: Walsh and Associates Real Estate.

$875,000

4 Beds ⋅ 3 Baths ⋅ 73591772 MLS

Introducing 18 Fairview Drive. This lovingly maintained home is filled with warmth and charm and is sited on a beautiful lot in a perfect location. Close to T station, major routes, walking distance to Finn School and fields! Surprisingly spacious with 4 bedrooms and 2.5 baths. Incredible curb appeal as you approach you will see the beautiful perennials and immediately feel at home! The first floor features an entertainers dream oversized kitchen with wine cabinets, island, hardwoods and eating area overlooking the gorgeous mature tree lined lot. The fireplaced family room is the perfect cozy spot for quiet nights or holiday celebrations. The formal living room could also serve as a home office. Upstairs the primary suite in its warm pallet features a large walk-in closet and private bath. The three additional bedrooms all with hardwoods are perfectly positioned with an additional updated full bath. The finished lower level adds comfortable space for hobbies, gym, or relaxing. Detached two car garage, workshop in basement... Wonderfully affordable lifetime home in popular neighborhood!

18 Fairview Drive, Southborough

Listing courtesy of Listing Agent: Kristine Wingate Shifrin from Listing Office: Andrew J. Abu Inc., REALTORS®.

$799,000

4 Beds ⋅ 3 Baths ⋅ 73591507 MLS

Welcome to this charming four-bedroom Colonial tucked away on a quiet cul-de-sac in desirable Southborough! Set on a beautiful, level ¾-acre lot, this home offers privacy, mature landscaping, and plenty of outdoor space to enjoy. The freshly painted exterior, completed in August, gives the home a classic, inviting look, while the brand-new composite deck completed in September provides the perfect low-maintenance space for relaxing or entertaining. Inside, the family room has a wood burning fireplace and a slider out to the deck and beautiful yard. The kitchen has ample cabinet space and an area for dining. Laundry is conveniently located on the first floor in the bathroom just off the kitchen, making everyday living easy and efficient. Above the garage is a large bonus room drenched with light from many windows and skylights to use as an extra family room or home office. With four bedrooms, one full bath, and two half baths, there is plenty of space for family and guests. The basement offers an abundance of storage space, including an impressive 8' x 11' fully lined cedar closet perfect for storing seasonal clothing, linens, and more. Roth oil tank is only 2 years old. The shed situated just off the driveway can house all of your tools and snowblower/riding lawn mower keeping your two-car garage less cluttered. Ideally located with easy access to major highways and the commuter rail, this home is also in close proximity to Southborough’s elementary schools. A wonderful combination of privacy, convenience, generous storage, this home is ready to welcome its next owner!

4 Garrison Ln, Southborough

Listing courtesy of Listing Agent: Karen Anglim from Listing Office: Andrew J. Abu Inc., REALTORS®.

$585,900

2 Beds ⋅ 1 Baths ⋅ 73589699 MLS

Minutes from Rt. 9, I-90, and Rt. 495, this charming 2-bedroom, 1-bath Colonial offers a rare blend of convenience, tranquility, and picturesque water views. Set on a peaceful lot overlooking a beautiful Sudbury reservoir, the property provides a serene backdrop that feels worlds away from the hustle of daily life while still offering exceptional commuter access. Inside, the home has been thoughtfully refreshed to create a warm and inviting atmosphere. The entire interior has been recently painted, giving each room a crisp, clean feel. Gleaming wood floors—professionally re-sanded and stained—flow throughout the home, adding character and timeless appeal. The formal dining room features classic built-in cabinetry, perfect for displaying glassware, serving pieces, or cherished décor. In the kitchen, granite countertops offer both durability and style, complemented by ample cabinet space and a layout ideal for everyday cooking or weekend entertaining. The living spaces are filled with natural light and offer comfortable areas for gathering, relaxing, or working from home. Upstairs, two well-proportioned bedrooms provide peaceful retreats with views of the surrounding landscape. Step outside and enjoy the true highlight of this property—its outdoor setting. The yard features fruit trees, mature shrubs, and natural plantings that enhance the sense of privacy and charm. A storage shed provides space for tools, gardening supplies, or seasonal items. The deck overlooking the water is the perfect place to start your morning with coffee, unwind at sunset, or host friends for weekend gatherings. Whether you enjoy birdwatching, quiet reflection, or simply taking in the scenery, the views here are exceptional. Additional features include a Passing Title V, Central AC throughout the home.

8 Winter St, Southborough

Listing courtesy of Listing Agent: Matthew Straight from Listing Office: Coldwell Banker Realty - Leominster.

$2,149,000

4 Beds ⋅ 7 Baths ⋅ 73588177 MLS

Located In Award winning Barn Hollow @ Schipper Farms By Nationally recognized BRENDON HOMES.The premier builder in the northeast. Sitting on a cul de sac with sweeping front lawn and fenced in backyard, abutting 68acres of conservation restricted land this home exemplifies elegance and desire .Pristine condition, diverse floor plan and amenities widely dispersed in the custom home with Custom 5,7,10 piece crown Molding, Exceptional Chefs Kitchen with marble counters, with Wolf and Subzero appliances, expansive center Island w/additional seating,The living room offers a grand ambiance with a distinguished fireplace, soaring high ceilings, expertly crafted built-in shelves, and decorative columns that enhance its architectural integrity. Beautiful Gleaming hardwood floors throughout this home, Sumptuous primary suite with spa like needs! Arched well appointed bedrooms with space and ample closets to accommodate all your Family needs! Arched center hall, 2 staircases, Repurposed Chefs kitchen and baths 2021 & Soaking tub, Walk out lower level offers you opportunity for Media Room,Gym,Au-pair or in- law suit .

4 Nipmuc Ln, Southborough

Listing courtesy of Listing Agent: Michael Durkin from Listing Office: LAER Realty Partners.

$2,080,000

5 Beds ⋅ 4 Baths ⋅ 73584144 MLS

**$40,000 Interest Rate Buydown Incentive!!!** The Seller is offering up to $40,000 credit to buyer for 2-1 interest rate buy down; inquire with listing agent for more details. Welcome home to this immaculate 2022-built estate in Southborough's coveted Chestnut Meadow neighborhood set along bucolic Chestnut Hill Road. This 4-5 bedroom, 4 full bath, 4,110 square-foot home delivers luxury finishes and quality craftsmanship throughout in a prime MetroWest location. A grand two-story foyer with custom millwork flows into the open-concept kitchen, dining, and family room areas. The kitchen impresses with premium modern cabinetry, Bosch induction cooktop (with propane gas line in place as well) and double ovens, 42" Sub-Zero built-in refrigerator, ducted vent hood, quartz countertop and backsplash, a waterfall-edge eat-in island, walk-in pantry, and a wine nook with wine fridge. The large dining area features built-in bench seating and upscale lighting, and flows seamlessly into the expansive family room anchored by a 60" Primo Heat-N-Glo propane gas fireplace bathed in natural light from windows on three walls. The first floor is rounded out by a versatile den (also ideal as a formal dining room), a private home office that doubles as a potential 5th bedroom, a full bath with shower, a walk-in coat/shoe closet, and a large mudroom. Upstairs, the sprawling primary suite features vaulted ceilings, an upgraded walk-in closet, and a spa-like bath with double vanity, oversized walk-in shower, soaking tub, and water closet. Three additional bedrooms — one with its own ensuite bath, and two sharing a large hall bath with double vanity — plus a spacious dedicated laundry room complete the upper level. The unfinished lower level offers great storage and future expansion potential. Outside, the flat fenced-in 1.29-acre lot offers ample space to host, play, and unwind, complemented by a partially covered composite deck for year-round enjoyment. Ideally located with close proximity to top-ranked private and public schools and easy access to Rt. 9, 495, Mass Pike, and the Commuter Rail. As an added bonus, the home can be sold fully or partially furnished for an additional cost. Don't miss your opportunity to call 12 Dairy Farm Lane home!

12 Dairy Farm Lane, Southborough

Listing courtesy of Listing Agent: Annie Pfaff from Listing Office: Gibson Sotheby's International Realty.

$1,185,000

4 Beds ⋅ 3 Baths ⋅ 73583751 MLS

Coveted Woodbury Estates colonial full of updates, including a stunning kitchen and family room renovation! The gorgeous kitchen is truly the heart of the home with an expanded island and top of the line appliances, including Sub Zero refrigerator, Wolf range with custom hood and a new Bosch dishwasher. The family room features cathedral ceilings and custom built ins that frame the fireplace and elevate the open concept entertaining space! Both the kitchen and family room have access out to the large deck and stunning new stone patio making the level backyard a wonderful gathering spot. The dining room is right off the kitchen and features beautiful wainscoting. The formal living room is adjoined by a private office space, both featuring new French doors and crown moldings offering privacy and elegance! The half bath and laundry room complete the first floor. Upstairs features a large primary suite with a walk-in closet and updated bath, with double vanity, a large spa tub and new tiled shower. Three additional generous bedrooms and another full bath with double vanity rounds out this level. Head to the lower level for recently renovated bonus space that makes a perfect playroom, movie room or home gym! Loads of recent updates including new siding in 2019, deck in 2020, stone patio, walls and fire pit 2023, front entry steps in 2025 to name a few. See complete list of updates attached! All this just a mile from the commuter rail, easy access to all major routes, shopping and tucked into one of the most desirable neighborhoods!

24 Darlene Dr, Southborough

Listing courtesy of Listing Agent: Alysha Glazier from Listing Office: Keller Williams Realty-Merrimack.

$5,000,000

5 Beds ⋅ 7 Baths ⋅ 73582552 MLS

What if your favorite destination was home? Set on one of Southborough’s most distinguished streets, 3 Wyndemere Drive is a residence designed for both extraordinary moments and beautifully lived everyday life - a place where timeless elegance, exceptional amenities and effortless comfort come together. From the moment you enter, soaring spaces, refined architectural details and an elegant flow create a sense of presence without sacrificing warmth. Expansive windows fill the interiors with natural light and capture views of the picturesque wildflower meadow and surrounding conservation land. At the heart of the home, beautifully appointed gathering spaces transition effortlessly from quiet mornings to intimate dinners and memorable evenings. The main-level primary suite is a world of its own - generously scaled, private and designed around the rituals of everyday luxury. A serene sitting room opens to a private balcony, while two exceptional walk-in closets create beautifully designed spaces for dressing, displaying and organizing a wardrobe with room to truly indulge. And then there’s downstairs, where an entirely different experience awaits. The expansive lower level is dedicated to entertaining, wellness and fun, with a sophisticated bar and oversized island, wine display, indoor grill, golf simulator and putting area, fitness space and impressive indoor jet pool. Perfect your swing, work out, gather for drinks or entertain late into the evening - all without ever making a reservation! Outside, approximately 4.6 acres of manicured grounds create a remarkable sense of privacy and a beautiful backdrop through the changing seasons. Generous living spaces, multiple levels of thoughtfully designed amenities and a three-car garage complete a residence created for life on a grand scale - yet with the warmth and versatility to feel equally at home during quiet everyday moments. Perfectly positioned in Southborough, the residence offers the rare combination of privacy and accessibility, with Fay and St. Mark’s schools nearby and Boston approximately 25 miles away - keeping exceptional education, culture and city access within easy reach. Elegant yet unexpected, sophisticated yet meant to be lived in, 3 Wyndemere Drive offers something increasingly rare: the freedom to entertain, play, recharge and enjoy life entirely on your own terms. This isn't simply a home to see. It's one to experience.

3 Wyndemere Dr, Southborough

Listing courtesy of Listing Agent: Edith Paley from Listing Office: William Raveis R.E. & Home Services.

$586,500

3 Beds ⋅ 2 Baths ⋅ 73582162 MLS

Move right into this beautifully updated 3 bedroom/1.5 bath home offering the perfect blend of comfort, style, and convenience. Enjoy stainless steel appliances, new solid-surface COUNTERTOPS, and a charming FIREPLACE that creates a warm and inviting living space. A new ROTH OIL TANK provides added efficiency and peace of mind, while a new MINI-SPLIT SYSTEM on the main level delivers supplemental heat in the winter and refreshing air conditioning in the summer. Need extra space? The bright SUNROOM is ideal for a home office, reading nook, or additional living area, while the FINISHED WALKOUT BASEMENT offers flexible space for a family room, guest suite, gym, workspace, and third bedroom with bath and NEW washer/dryer tower. Conveniently located just minutes from the COMMUTER RAIL, ROUTE 9, shopping, dining, and everyday amenities, this move-in-ready home offers easy commuting with the flexibility today's buyers are looking for. Don't miss this wonderful opportunity!

47 Southville Rd, Southborough

Listing courtesy of Listing Agent: Lisa Benway from Listing Office: eXp Realty LLC.

$725,000

3 Beds ⋅ 3 Baths ⋅ 73580361 MLS

Incredible one-level living with oh so many options - terrific flexible floorplan with impressive open flow making the home feel much larger than its actual size! Gorgeous kitchen with gleaming granite counters and large island and cherry cabinets Spacious room off the back of the house could be a large primary bedroom or another large gathering space for entertaining*Delightful and spacious screened porch is perfect for additional entertainment space and enjoys a view of the amazing rear yard allowing three season enjoyment! Freshly painted 4 room "in-law" set up with private entrance AND a detached approximately 1200 square foot building with heat could be used for so many possibilities - hobbies, future ADU, office space, storage, retreat or it could be converted back two-car garage with rooms behind it for a multitude of use!

216 Boston Rd, Southborough

Listing courtesy of Listing Agent: Kristine Wingate Shifrin from Listing Office: Andrew J. Abu Inc., REALTORS®.

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