Southborough Homes for Sale

Welcome to Southborough, Massachusetts – a hidden gem nestled in Worcester County, where small-town charm meets modern convenience. This picturesque community is known for its serene landscapes, top-rated schools, and a rich history that dates back to the 18th century. With its lush greenery, well-maintained parks, and a friendly atmosphere, Southborough offers a perfect backdrop for families, professionals, and retirees alike.

The town is conveniently located just 30 miles west of Boston, providing easy access to the vibrant city while allowing residents to enjoy the tranquility of suburban life. Southborough boasts a variety of recreational activities, including hiking trails, sports fields, and community events that foster a strong sense of belonging among its residents. The historic downtown area features charming local shops and eateries, making it a delightful place to explore.

If you're considering making Southborough your home, you're in luck! The real estate market here offers an enticing selection of homes for sale, ranging from cozy single-family residences to sprawling estates. Each property reflects the town's unique character, with many featuring beautiful architectural details, spacious yards, and modern amenities. Whether you're looking for a starter home or a luxurious retreat, Southborough has something to suit every lifestyle and budget.

With its excellent schools, vibrant community spirit, and beautiful surroundings, Southborough is more than just a place to live – it's a place to thrive. Explore the homes for sale today and discover the perfect property to call your own in this enchanting town!

Newest Southborough Homes for Sale

$665,000

3 Beds ⋅ 2 Baths ⋅ 73594316 MLS

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 being installed fall of 2026. Updated in 2021, the enclosed second-floor porch offers flexible bonus space for a home office, hobbies, or relaxation.Recent improvements include a new roof in 2019, siding 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

$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

$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

$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

$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

$675,000

3 Beds ⋅ 2 Baths ⋅ 73587404 MLS

Charming 1850 Greek Revival offering the perfect blend of historic character and thoughtful updates! Beautiful quarter-sawn oak floors and hardwood flooring add warmth and character throughout the home. The gorgeous renovated cathedral-ceiling kitchen features quartz countertops, abundant cabinetry, stainless steel appliances, plenty of space for gathering and entertaining. The gracious dining room features built-in cabinetry and a cozy pellet stove, while the front living room offers French doors and wonderful natural light. A convenient first-floor bedroom and full bath provide added flexibility. Upstairs, you’ll find two additional bedrooms and a second full bath. Recent improvements include a new roof (2021), replacement windows (2017), concrete basement floor (2017), and Riello oil burner and water heater (2014). Outside, a large deck with a Sunset Pergola overlooks the spacious yard—perfect for entertaining, gardening, and outdoor enjoyment. A large fenced garden area was added in 2021. The property also features a carriage house with attached garage, offering exceptional storage, workshop, or office possibilities, all surrounded by woodlands and streams. Located in the Historic District with easy access to the Mass Pike, Routes 495, 9 and 85, and within walking distance to the T station. A truly special property combining timeless New England charm, modern updates, and a beautiful setting!

151 Southville Rd, Southborough

$1,017,888

4 Beds ⋅ 4 Baths ⋅ 73587314 MLS

Certified Turnkey. Pre-inspected, repaired and thoughtfully updated, this 4-bedroom, 3.5-bath Southborough Colonial offers 3,700+ sq. ft. of living space plus 432± sq. ft. of finished flex space above the detached 2-car garage. Major improvements include a new driveway (10/2026), new 4-bedroom septic (9/2026), roof (5/2026), central air (2024) and 42 Harvey windows (2016). The renovated kitchen with gas cooking flows into a dramatic two-story barn-board family room with exposed beams, gas fireplace and access to the composite deck. Formal living and dining rooms, two staircases and a bath on every level add flexibility to the floor plan. Upstairs, the primary suite includes a walk-in closet and private bath, with three additional bedrooms and a full hall bath. The finished walk-out lower level expands the living space with a game/billiard area, wet bar, full bath and direct outdoor access—ideal for entertaining, guests or extended living. Outside, enjoy a 16' x 32' saltwater pool with new liner (6/2026), composite deck with full awning (2026) and a landscaped .88-acre lot abutting conservation land, the Sudbury Reservoir and nearby trails. The detached 2-car garage offers finished heated rooms above—ideal for a home office, studio, gym or creative space. Three garage bays in total provide additional parking and storage. A home designed for everyday living, entertaining and escaping without leaving home, yet convenient to the MBTA commuter rail, Route 9, I-90 and I-495. This house comes with a REDUCED RATE as low as 6.5% (APR 7.004%) as of 10/09/2026 through List & Lock™(depending on the offer price) This is a seller paid rate-buydown that reduces the buyer’s interest rate and monthly payment. Terms apply, see disclosures for more information.

8 Partridge Hill Rd, Southborough

$799,000

5 Beds ⋅ 4 Baths ⋅ 73584898 MLS

A rare opportunity to become the next steward of an exceptional home or investment property in one of Southborough's most convenient locations. Set on an oversized 1.4-acre lot along a quiet neighborhood street, this versatile 5 bedroom, 3.5-bath property (2,586 sq. ft. total) offers two attached living spaces — a 4-bedroom + office, 2.5-bath main residence (approx. 2,078 sq. ft.) and a 1-bedroom, 1-bath in-law suite/ADU (approx. 508 sq. ft.). The configuration is nicely suited for multi-generational living, an au pair suite, income property potential, or whatever flexible arrangement fits your plans. The main residence offers a traditional floor plan with an eat-in kitchen with stainless steel appliances, dedicated first floor laundry room/pantry, a large formal dining room, separate family and living rooms, a primary suite with attached ensuite bath, three additional generously sized bedrooms with hardwood floors sharing a full hall bath with double vanity, and a bonus room perfect as home office, gym, or flex space of your choosing. The in-law unit includes an eat-in kitchenette, living room, bedroom, and full bath with tub. Outside, a composite deck overlooks the in-ground pool (in good working order), and the expansive lot leaves plenty of room to garden, play, entertain, or simply spread out. With this much space, land, and flexibility in a convenient Southborough location, there is significant upside for the right buyer ready to bring their vision to life. Ideally located with proximity and access to top-ranked schools and easy access to the Commuter Rail, Rt. 9, 495, and the Mass Pike.

11 Summit Road, Southborough

$1,050,000

3 Beds ⋅ 3 Baths ⋅ 73584214 MLS

Picture perfect and impeccably maintained, this wonderful 3 bedroom with private office, 3 bath Gambrel Colonial offers the classic New England charm combined with all the modern updates. Situated on 1.1 acres of professionally landscaped grounds, this exceptional home is surrounded by flowering trees and shrubs, vegetable gardens and beautiful rock walls. The stunning 2022 primary suite addition features a vaulted ceiling, luxurious new bath with tile shower and fabulous walk-in closet with custom designed closet organizers. Recent updates also include a new full bath on the main level with oversized pedestal sink, heated towel rack and tile shower. Separate laundry area with cabinets above washer/dryer and closet with custom closet organizers was built in 2022. The chef's kitchen is designed for both everyday living and entertaining offering white wood cabinets with an abundance of drawers, quartz countertops, st/steel appliances, wine refrigerator and an oversized island with a double sink. Custom white cabinets flank the fireplace that was recently converted to a wood burning stove in the dining room. Perfect for those cold wintry nights! Breakfast bar with seating for four divides the family room and dining area. Breathtaking fenced back yard with newer composite deck and newly built shed overlooks the private grounds. Wide plank pine floors throughout the first floor and newly installed hardwood floors in 2 of the bedrooms and office, recessed lights, replacement windows, three new dormers installed in the bedrooms, new siding and exterior trim, roof replaced, completely new driveway, 5 Mitsubishi mini-splits, whole-house generator and the list goes on! Nothing to do but move in! This is a very special home!

64 Pine Hill Road, Southborough

$2,080,000

5 Beds ⋅ 4 Baths ⋅ 73584144 MLS

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

$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

$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

Start Your Search

IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but is not guaranteed. © 2026 State-Wide Multiple Listing Service. All rights reserved. Data Last Updated:

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

Southborough Homes for Sale

Newest Southborough Homes for Sale

How much is your home worth?

How much is your home worth?