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$1,640,000
5 Beds ⋅ 6 Baths ⋅ 73393810 MLS
Coveted DOVER-SHERBORN schools, only 20+ mi west of Boston. Sunlight streams in windows to cathedral ceilings w/ 3 fireplaces, a grand 2 story foyer & curved stairway, DR, LR, FR, HOME OFFICE. Sweeping front lawn with pastoral views.

4 Green Ln., Sherborn

Listing courtesy of Listing Agent: Barbara Bowen from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.
$4,550
2 Beds ⋅ 3 Baths ⋅ 73551373 MLS
Luxury Townhome in Sherborn’s Top-Rated School District | Available September.Start the school year in one of Massachusetts’ most sought-after communities. Built in 2020, this beautifully maintained townhome offers over 2,500 square feet of thoughtfully designed living space, combining modern finishes, low-maintenance living, and exceptional access to the highly acclaimed Dover-Sherborn school system. The sun-filled open floor plan features spacious living and dining areas, a cozy gas fireplace, and a modern kitchen designed for both everyday living and entertaining. Upstairs are two generously sized bedrooms, two full bathrooms, and convenient second-floor laundry. The finished walkout lower level adds incredible flexibility, making it perfect as a home theater, family room, home office, fitness space, or guest area.

10 Southfield Ln Unit 10, Sherborn

Listing courtesy of Listing Agent: Darin Thompson from Listing Office: Stuart St James, Inc..
$1,450,000
5 Beds ⋅ 3 Baths ⋅ 73513140 MLS
Located on the east-side of Sherborn in the coveted FARM POND/ROCKY NARROWS NEIGHBORHOOD, this move-in-ready 5 BEDROOM colonial is a sanctuary for nature lovers, outdoor enthusiasts & those searching for a beautiful setting to call home. Extensively RENOVATED to offer a seamless open floor plan, the home features a designer kitchen w/high-end appliances, custom cabinetry & large center island.This sun-filled space flows into a stunning sunroom w/gas fireplace overlooking a gorgeous patio & lush gardens, family rm w/fireplace & built-in desk, spacious dining rm & front-to-back living rm w/fireplace. Upstairs, the primary suite serves as a private retreat w/dual walk-in closets & renovated bath, + 4 additional bedrooms, renovated family bath & laundry. Additional highlights include: mudrm, finished lower level w/full-sized windows, hardwood flrs, central AC, generator hook-up, newer windows… Perfectly located for relaxation & recreation right from your doorstep & it’s a commuter’s dream!

7 Goulding St. East, Sherborn

Listing courtesy of Listing Agent: Laura Mastrobuono from Listing Office: Compass.
$6,800
3 Beds ⋅ 4 Baths ⋅ 73555186 MLS
Beautiful contemporary rental available! Unique and immaculate contemporary style home with walls of glass overlooking the bucolic and private 3+ acre property. This 3 bedroom home has an open floor plan, bamboo floors, an abundance of natural daylight, fireplace, built-ins, high ceilings, a skylit stairway and metal roof. Gourmet kitchen w butler pantry, stainless appliances, gas cooking and island, open dining area and living room with a fireplace flanked by built-ins and a cathedral ceiling. First floor primary bedroom accompanied by 2 en suite second floor bedrooms. First floor home office, laundry and half bath. Storage galore in the basement with high ceilings. Oversized 1 car garage with storage area. Just move right in. Must see this great home! Sherborn has a very high rated school system and part of the Dover-Sherborn Middle and High School. Farm Pond and Sherborn Yacht Club close by and walking trails to explore.

32 Nason Hill Rd Unit 32, Sherborn

Listing courtesy of Listing Agent: Jane Wemyss from Listing Office: Compass.
$2,800,000
5 Beds ⋅ 6 Baths ⋅ 73504628 MLS
Spanning 25 acres, this extraordinary estate centers on a stocked, stream-fed private pond, winding trails, manicured grounds, and a beautifully renovated Georgian Colonial. Offering a unique lifestyle, enjoy fishing, boating, and year-round wildlife. Thoughtfully reimagined through extensive renovation inside and out, the residence blends timeless character with modern amenities, exceptional craftsmanship, energy efficiency, and smart technology. 4 levels showcase high ceilings, abundant natural light, and breathtaking pond views. Two-story foyer opens to elegant living and dining rooms, family room, chef’s kitchen, and expansive deck overlooking the pond, plus 1st-floor primary suite and richly paneled office. Upstairs are 4 corner bedrooms with walk-in closets and updated baths. Completely renovated walkout lower level with expansive mudroom offers spaces for recreation, gym, au pair, and full bath. An unmatched lifestyle with top-rated Sherborn schools and easy access to Boston!

75 Washington St, Sherborn

Listing courtesy of Listing Agent: Benna Lynch Rondini from Listing Office: Charlesgate Realty Group LLC.
$2,300,000
5 Beds ⋅ 5 Baths ⋅ 73492392 MLS
This extensively renovated home is a masterpiece of design and functionality, offering a stunning fusion of modern sophistication and elegance. Set well back from the road in an idyllic setting, it provides a sense of peace and privacy that's hard to find. At its heart is the light-filled gourmet kitchen, family room and breakfast nook/sunroom. Combined with five spacious bedrooms, four and a half baths, multiple family and office spaces, a theater, exercise area and more, this home is perfect for living, working, and unwinding. Discover seamless indoor-outdoor living, complete with multiple bluestone patios, stunning professional landscaping and lighting, and the spacious, level backyard. Sherborn, just 20 miles southwest of Boston, is a picturesque town with top-rated schools, Farm Pond, miles of trails, acres of conservation land and open spaces. Come see why Boston.com named Sherborn a top place to buy for 2026 and this exquisite home is at the heart of it all!

76 Hollis Street, Sherborn

Listing courtesy of Listing Agent: The Powissett Group from Listing Office: Compass.
$1,885,000
5 Beds ⋅ 5 Baths ⋅ 73523960 MLS
Presenting an award winning CONTEMPORARY MASTERPIECE: Sited on 5.5+ breathtaking acres at the end of a private winding drive, this 5 bedroom, 5400 sqft modern villa is a true collaboration of elite design & nature. Soaring ceilings, walls of windows & skylights create a sun-drenched sanctuary, highlighting meticulous craftsmanship w/cherry floors, mahogany stairs, & patinaed copper trim. Experience effortless ONE LEVEL LIVING w/ELEVATOR access to a stunning open-concept layout. The gourmet kitchen, fire-placed living room & magical sunroom flow seamlessly to a substantial deck & HEATED POOL/SPA, perfectly integrated into the serene landscape. With a superb primary suite, show stopping home office, game room & 4 garage bays, this home caters to both elegant entertaining & comfortable daily life. Enjoy Sherborn’s top-ranked schools, Farm Pond & vast trail networks ~18 miles from Boston. A one-of-a-kind sanctuary where sophisticated design meets rural tranquility-COME SEE!

44 Maple Street, Sherborn

Listing courtesy of Listing Agent: Laura Mastrobuono from Listing Office: Compass.
$1,649,000
3 Beds ⋅ 2 Baths ⋅ 73522431 MLS
Privately nestled along a scenic approach, this exceptional 8.06-acre country estate offers a rare blend of luxury living, timeless character & equestrian potential. Offered for the first time ever, the property features expansive open fields, including 5 acres of lush hay fields, ideal for horses, hobby farming, or refined country living. The beautifully renovated 3-bedroom, 2-bath home has been thoughtfully updated while maintaining its warmth & charm. Recent improvements include new windows, siding & new roofing on all 3 structures, along with extensive interior renovations, quartz countertops & modern upgrades throughout. A striking two-story timber frame barn serves as the centerpiece of the property, offering excellent potential for equestrian use, storage, workshops, or future customization. Surrounded by sweeping open acreage & peaceful natural beauty, this remarkable property offers privacy, functionality & elegance in an extraordinary setting.

177 Maple St, Sherborn

Listing courtesy of Listing Agent: Kerry Parker from Listing Office: Equine Homes Real Estate, LLC.
$5,995
4 Beds ⋅ 3 Baths ⋅ 73546246 MLS
Experience single-level living at its finest in this beautifully maintained 4 bedroom, 3 bath ranch set on a serene 3-acre lot in picturesque Sherborn known for top rated schools and convenience to Boston. This 3,713 sq ft home offers soaring ceilings, walls of windows, and peaceful views that seamlessly blend indoor comfort with natural beauty. Enjoy a renovated eat-in kitchen, updated baths, generous bedrooms, and refinished hardwood floors throughout. Improvements also include a 2024 new roof & 4- bedroom septic. Modern conveniences include gas cooking, central A/C, first-floor laundry/mudroom, and a spacious screened-in porch. The walk-out lower level features a fireplace and expansive finished and unfinished spaces, ideal for work, play, or storage. With open lawn, private woods, and exceptional privacy, this property offers a rare combination of style, function, and nature—perfect for a wide range of lifestyles. Available for short term rental thru 3/31/2027. CAN BE RENTED FURNISHED.

62 Mill St, Sherborn

Listing courtesy of Listing Agent: The Madden David Real Estate Group from Listing Office: Coldwell Banker Realty - Wellesley.
$1,600,000
4 Beds ⋅ 3 Baths ⋅ 73532530 MLS
Built in 2017, this beautifully maintained & further improved center-entrance Colonial offers the perfect blend of modern living & Sherborn's natural surroundings. Tucked away on 1.61 private acres, this 4-bedroom, 2.5-bath home features over 3,000 sq feet of living space, including a bright, open-concept kitchen with island, spacious family room, dedicated dining room, mudroom, and finished lower-level flex space. Upstairs, the expansive primary suite offers a peaceful retreat with a private bath and walk-in closet. Completing the 2nd floor are 3 addl bedrooms & a full bath providing ample space for family, guests, or home office needs. Enjoy outdoor living on the deck & patio overlooking a level backyard surrounded by mature trees. This home is conveniently located near conservation land, walking trails, parks, & tennis courts, w/ access to the top-rated Dover-Sherborn school district. A rare opportunity to own this young Colonial in one of MetroWest's most sought-after communities

70 S Main St, Sherborn

Listing courtesy of Listing Agent: Morgan Guthrie from Listing Office: Douglas Elliman Real Estate - Wellesley.
$2,237,640
5 Beds ⋅ 4 Baths ⋅ 73497289 MLS
HOUSE BEAUTIFUL: This stunning 5000 sqft contemporary farmhouse, CUSTOM BUILT in 2014, is idyllically sited on 2.5 picturesque Sherborn acres with a charming antique BARN & in-ground POOL & includes every amenity today’s Buyer is looking for! The open floor plan features high ceilings, hardwood floors & custom millwork across (3) finished levels. The heart of the home is a chef’s kitchen with Carrara marble island & custom cabinetry; the adjoining sun-drenched family room w/fireplace & sliders opening to a deck overlooking a flat, manicured backyard w/stone walls, private meadow & pool. Additional highlights include a private home office, spacious mudroom & primary suite w/dual walk-in closets & spa-worthy bath. With 3 additional bedrooms, one w/ensuite bath, 2nd floor laundry, a finished lower level & GAS cooking/heating, this home checks all the boxes! Ideally located on the east-side of town near schools, the commuter rail, hiking trails & town beach, don’t miss this SHERBORN GEM!

2 Snow Street, Sherborn

Listing courtesy of Listing Agent: Laura Mastrobuono from Listing Office: Compass.
$3,100,000
6 Beds ⋅ 7 Baths ⋅ 73480584 MLS
Set on 3.7 pristine acres abutting 600+ acres of conservation land and Little Farm Pond, this grand estate offers rare privacy and pedigree- first owned by former Boston Celtics head coach Rick Pitino. Soaring ceilings and twin staircases lead to five upstairs bedrooms. The primary suite stuns with a 400sq-ft marble spa bath featuring three sinks, makeup vanity, steam shower, and Jacuzzi tub. A walk-out lower level is built for guests and entertaining with an au pair suite with full bath, a second full bath, second office with custom desks, large sauna, steam room, fitness room, game and movie room, wet bar with refrigerator and dishwasher. Outside, the oasis includes an oversized pool with waterfall, a cabana with enclosed shower, granite counters, refrigerator, surround sound, and 80” TV. Design forward interior includes an open chef’s kitchen with all Wolf/Sub-Zero, sunroom, floor-to-ceiling fireplaces, expansive decks, built-ins, and recent updates for luxury living & entertaining.

137 Lake Street, Sherborn

Listing courtesy of Listing Agent: Elena Price from Listing Office: Coldwell Banker Realty - Westwood.
$1,570,000
4 Beds ⋅ 3 Baths ⋅ 73508240 MLS
Ideally located on quiet CUL-DE-SAC in sought after, walk-to town Sherborn neighborhood, this much admired MOVE-IN READY home has it all! Perfectly sited on almost 2 acres of flat, usable land w/the perfect balance of open lawn & wooded areas for play & privacy, this property boasts captivating curb appeal & does not disappoint inside or out! A beautiful & functional RENOVATION perfectly completed this home: walls came down, kitchen renovated, ceilings raised, field stone fireplace added & the ideal space for entertaining & everyday life was created. Other notable features include: chef’s kitchen w/GAS Viking range, hardwood floors throughout, central AC, newer septic system & Buderus boiler, dedicated home office, 3 fireplaces, 3-season screened porch w/cedar floors opens to large deck over-looking picture perfect backyard, nicely finished lower level, mudroom...the list goes on. Sherborn offers easy access to commuter rail, top-tier schools, bucolic Farm Pond & expansive trail system

3 Bridle Path, Sherborn

Listing courtesy of Listing Agent: Laura Mastrobuono from Listing Office: Compass.
$1,130,000
4 Beds ⋅ 3 Baths ⋅ 73528552 MLS
SINGLE LEVEL LIVING at it’s best: Completely updated, meticulously maintained & move-in ready 4 bedroom RANCH in coveted east-side of Sherborn neighborhood w/easy trail access to Farm Pond & located on CUL-DE-SAC for additional privacy! Set well off the road, this 1.3+ ac lot w/stonewalls & mature plantings offers the perfect combination of flat usable open lawn & wooded areas for privacy & play. The main level includes a huge eat-in kitchen w/fireplace & white custom cabinets, large living & dining rooms w/oversized windows & fireplace, screened-in porch, 3 bedrooms, 2 full baths & laundry. Walk-out lower level w/full sized windows includes 4th bedrm, bathrm, home office/rec rm & offers plenty of room for work, play, exercise, storage & systems; hardwood flrs, central A/C, 3 fireplaces, 2 car garage, newer septic…w/too many features to list, come see this great property that will appeal to a variety of lifestyles, close to Sherborn center, Dover Sherborn’s #1 schools & commuter rail!

26 Peckham Hill Road, Sherborn

Listing courtesy of Listing Agent: Laura Mastrobuono from Listing Office: Compass.
$1,750,000
6 Beds ⋅ 4 Baths ⋅ 73517075 MLS
Just 18 miles west of Boston in the idyllic town of Sherborn, Stonegate Farm offers a rare, meticulously maintained TWO-HOME COMPOUND—a beautifully restored antique & a thoughtfully designed newer residence—joined together yet providing fully distinct living spaces. Ideal for MULTI-GENERATIONAL LIVING or RENTAL INCOME, the property blends historic character w/modern comfort. The antique home features wide-plank floors, updated kitchen & baths, sunlit gathering rooms, 3 bedrooms + 3rd floor bonus room. The newer 2 bedroom home centers on a vaulted Great Room w/access to deck, porch & glorious gardens. Set on 3+ acres, the property includes perennial gardens, stone paths & outdoor areas that invite time spent outside. With (5) garage bays, updated systems, central AC, solar sys & newer 6-bed septic, Stonegate Farm offers privacy, flexibility & enduring care in a highly regarded community w/top schools, coveted open space for year round enjoyment & close proximity to the commuter rail.

215 Washington Street, Sherborn

Listing courtesy of Listing Agent: Laura Mastrobuono from Listing Office: Compass.
$1,270,000
3 Beds ⋅ 3 Baths ⋅ 73520980 MLS
Striking magazine quality mid-century modern set on 4+ private, wooded acres with direct access to scenic hiking trails. Extensively renovated in 2018, this home blends clean architectural lines with warm, inviting interiors. Sun-filled open living and dining areas feature exposed beams, walls of glass, and seamless access to an expansive deck—perfect for indoor/outdoor living. Sleek, updated kitchen with large island, custom cabinetry, and high-end appliances. The spectacular primary suite offers walls of windows overlooking the forest, a walk-in closet with custom organizers, and a beautifully styled bathroom with soaking tub, walk-in shower, double vanity, and skylight. Spacious rooms, hardwood floors, and thoughtful updates throughout. Oversized two-car garage and generous driveway. Very close to the West Natick commuter train station. A rare offering combining style, privacy, and modern comfort.

59 Prospect St, Sherborn

Listing courtesy of Listing Agent: Bill Paulson from Listing Office: Keller Williams Realty.
$1,510,000
4 Beds ⋅ 4 Baths ⋅ 73519568 MLS
The Flagg House, one of Sherborn’s most architecturally and historically significant homes, is set on 2+ pastoral acres near the renovated public library, athletic fields, and town center. A stone driveway lined with graceful sugar maples leads to private Maple St. entrance. Property includes a 2-story garage with Rt. 16 access, gardening shed, and antique stone walls. Sunny vestibule opens to mudroom, laundry, and half bath. South-facing kitchen with “secret garden” patio features SS appliances incl Sub-Zero fridge, dbl wall ovens, trash compactor, and farmhouse sink. Four main-level rooms feature wood-burning fireplaces, 10’ ceilings, exposed beams, wide plank hardwoods, and abundant storage. A 9x32 sunporch offers a light-filled retreat. Main level also includes a full bath with clawfoot tub. Elegant foyer with beam bar front door leads to period staircase and 2nd level. Upstairs: 3 bright bedrooms, family bath, and ensuite primary w/dressing room, dbl closets, and renovated bath.

3 Maple St, Sherborn

Listing courtesy of Listing Agent: The Bauman Group from Listing Office: Gibson Sotheby's International Realty.
$935,000
2 Beds ⋅ 2 Baths ⋅ 73518338 MLS
This Deck House, tucked well off the street, seamlessly blends into its natural surroundings with high ceilings and expansive windows, inviting the outside in. It’s perfect for first-time buyers or anyone looking to downsize, a perfect condo alternative. With 2 bedrooms, 2 baths, and a 3-bedroom septic system in place, this home is ready for you to move right in, or bring your vision to life and expand it into your dream space or possibly add an ADU. Utilizing passive solar, this home is low maintenance and energy efficient. The 3 acres include lush greenery, beautifully placed perennial gardens, and 2 patios that are ideally situated for soaking up the beautiful surroundings. The two-car garage offers plenty of space. Whether it’s the serene setting, the gorgeous outdoor spaces, or peaceful living that you desire, 67 Woodland St is ready to welcome you home. Sherborn, with its top rated schools, Farm Pond, and extensive trail network, was named a top place to buy in 2026 by Boston.com

67 Woodland Street, Sherborn

Listing courtesy of Listing Agent: The Powissett Group from Listing Office: Compass.
$900,000
2 Beds ⋅ 3 Baths ⋅ 73523210 MLS ⋅ ['Abbey Road Condominiums'] BLDG.
LUXURY, MAINTENANCE-FREE LIVING IN THE HEART OF SHERBORN! Welcome to Abbey Road, a highly admired 55+ community composed of 18 high-quality, homes. This "like-new" unit masterfully pairs 1st-floor living with a sun-soaked, open-concept design. The showstopping white kitchen features stone counters, a buffet style counter and a dining area with true raised-panel wainscoting. It flows effortlessly into the dramatic, two-story family room, anchored by a gas fireplace and floor-to-ceiling picture windows. The 1st-floor main suite is a true retreat, boasting a luxurious bath with a walk-in tile shower, massive walk-in closet and direct access to a private patio. A versatile large loft leads to a second en-suite bedroom with its own private balcony. Enjoy a close-knit neighborhood vibe with access to a stunning, professionally landscaped common courtyard complete with walkways, a fire pit, and a grill area. Garage under plus off-street parking for guests. All this, plus close to town center!

14 Abbey Road Unit 14, Sherborn

Listing courtesy of Listing Agent: Erika Steele from Listing Office: REMAX Executive Realty.
$1,325,500
4 Beds ⋅ 3 Baths ⋅ 73530633 MLS
Located in one of Sherborn's most desirable neighborhoods, 2 Russett Hill Road combines a classic, updated interior with an expansive lot. The home has been thoughtfully renovated, featuring a stunning kitchen with hidden pantry, modern bathrooms, built-ins, a flexible floor plan, dedicated private office, and finished lower level with versatile living space and abundant built-in storage. Tennis anyone? Exceptional outdoor living includes a screened porch, expansive deck, stone patio, and private tennis court, creating the perfect setting for entertaining, recreation, and relaxation. Sherborn, with its top rated schools, Farm Pond, and extensive trail network, was named a top place to buy in 2026 by Boston.com. Don't miss this wonderful opportunity to call Sherborn home!

2 Russett Hill Road, Sherborn

Listing courtesy of Listing Agent: The Powissett Group from Listing Office: Compass.
$1,005,000
3 Beds ⋅ 3 Baths ⋅ 73526227 MLS
Welcome to 86 N Main Street, a 19th Century Antique, with a complete 21st century renovation in 2009. Featuring 2+ acres of picturesque landscaping, an expanded Cape & a showstopper post & beam barn in charming Sherborn! Light-filled rooms, cherry hardwood floors throughout, 3 bedrooms, 2.5 baths & a spacious kitchen that opens seamlessly to multiple gathering areas make this home as livable as it is charming. Oversized windows create a warm and airy feel throughout. The separate multi-level barn offers soaring timber framing, incredible character & endless possibilities for workshop, studio, garage or hobby space. Generous lot offers privacy & room to roam while keeping you conveniently close to top-rated schools, conservation trails, local farms & Sherborn center, all while embracing the charm and appeal of small-town living. A rare opportunity to enjoy space, character & location all in one.

86 N Main Street, Sherborn

Listing courtesy of Listing Agent: Prudence B. Hay from Listing Office: Rutledge Properties.
$2,025,000
5 Beds ⋅ 6 Baths ⋅ 73497520 MLS
Set along one of Sherborn’s most desirable cul-de-sac neighborhoods, 3 Knollcrest Farm is a private estate offering an exceptional blend of elegance, comfort, and resort-style living. The residence has been completely refreshed with a fully repainted interior, creating a bright, cohesive, move-in-ready environment. Graciously scaled rooms, refined finishes, and timeless architectural details define the home’s sophisticated character. The grounds are equally impressive, designed for both relaxation and recreation. A stunning in-ground heated pool and spa are complemented by a beautifully appointed pool house, creating a true summer retreat. A dedicated pickleball court adds a modern lifestyle amenity, while a separate carriage house provides ideal accommodations for visitors, extended family, or private workspace. Surrounded by mature landscaping and offering remarkable privacy, this property delivers a rare opportunity to enjoy luxury living, top schools, and easy commuting routes.

3 Knollcrest Farm Ln, Sherborn

Listing courtesy of Listing Agent: The Berkowitz Team from Listing Office: Keller Williams Boston MetroWest.
$1,650,000
4 Beds ⋅ 3 Baths ⋅ 73484534 MLS
Located in sought-after Sherborn neighborhood, close to town & top-tier schools, this MOVE-IN READY, METICULOUSLY MAINTAINED home sited on 1 acre has it all: A beautiful & functional RENOVATION/ADDITION perfectly completed this home…walls came down, kitchen was renovated, mudroom, laundry & great room added & ALL boxes were checked! This home now offers what all Buyers want: an OPEN FLOOR PLAN, kitchen w/center island, custom cabinetry & high-end appliances, great room that opens to a well designed outdoor space, perfect for entertaining & everyday life; formal dining & living rm w/2nd fireplace & built-ins providing multi-functional spaces to suit a variety of life-styles; 4 generously-sized bedrms on 2nd fl, updated baths, plenty of storage, hardwood flrs thorough-out, radiant heat, central AC, private backyard, mature gardens, stonewalls, front porch, oversized attached garage w/unfinished walk-up 2nd lv presenting possible expansion opportunities, incredible finished LL...COME SEE!

41 Ivy Lane, Sherborn

Listing courtesy of Listing Agent: Laura Mastrobuono from Listing Office: Compass.
$1,050,000
4 Beds ⋅ 3 Baths ⋅ 73510579 MLS
Nestled within the highly desirable Old Orchard/Page Farm neighborhood, this classic Colonial offers a compelling opportunity to invest in sought-after Sherborn. Privately set on four scenic acres and approached by a long driveway, the property combines timeless appeal, comfortable living spaces, and potential to personalize. With its generously scaled interiors, four bedrooms, two-and-a-half baths, an oversized mudroom, attached two-car garage, and a walk-out lower-level opening to the patio, the home's well-designed layout is both functional and inviting. Recent updates include exterior paint, appliances, recessed lighting, and a 2019 septic system - important investments already in place. This is a chance to enjoy the lifestyle and long-term rewards of living in an admired town known for its top-rated schools, natural beauty, and close-knit community. Convenient to the Bailey Trail system, residents-only Farm Pond, shopping, restaurants, commuter rail access to Boston.

18 Old Orchard Road, Sherborn

Listing courtesy of Listing Agent: Friedler / Marchant Living Group from Listing Office: Hammond Residential Real Estate.
$2,125,000
4 Beds ⋅ 4 Baths ⋅ 73484871 MLS
Full renovated home on a quiet country cut de sac in desirable Sherborn, set on 3 acres. This custom renovation is flooded with light and thoughtful details throughout. The two-story foyer with board-and-batten opens to a seamless first floor, featuring a formal living room with wood fireplace and a chef’s kitchen with Monogram appliances, double wall oven, and induction cooktop. The informal living area with cathedral ceiling overlooks a large deck and in-ground pool. First-floor home office/study adds flexibility to the open floor plan. On the second level, the primary suite offers a spa-like bath, soaking tub, custom tile shower, and large closet, alongside three bedrooms, full bath, and laundry. Walk-out lower level includes an impressive wet bar area, exercise area and game room! Every detail of this home blends modern luxury with timeless New England charm, offering an elegant, sun-filled retreat for entertaining, relaxing, and enjoying the serene privacy of Sherborn living.

54 Spywood Rd, Sherborn

Listing courtesy of Listing Agent: The Bohlin Group from Listing Office: Compass.
$8,000
3 Beds ⋅ 4 Baths ⋅ 73504893 MLS
Move right in and enjoy Farm Pond this summer! This young colonial has both classic charm & modern updates. The open concept floor plan includes a recently remodeled custom chef's kitchen with industrial size SubZero fridge/freezer, 6 burner wolf range and a huge island with 2nd fridge & 2nd full size sink. Family room opens to a breathtaking full glass sunroom complete with a projector for watching movies under the stars. Living,dining, convenient mudroom with "hidden" pantry, laundry and full bath complete the first floor. Second floor includes an impressive primary suite with wall of storage and updated bathroom. Additional 2 bedrooms, one being an ensuite, are generous in size and complete with custom closets, recessed lighting & hardwood floors. Large flex space over the garage includes plenty of storage. All set on beautiful manicured lawn with lovely maintained flower beds. This property,combined with Sherborn’s top-rated schools, Farm Pond & extensive trails,is not to be missed

93 Goulding St W, Sherborn

Listing courtesy of Listing Agent: Amy Caffrey from Listing Office: Compass.
$1,760,000
6 Beds ⋅ 7 Baths ⋅ 73499482 MLS
Welcome to Russet Hill Farm, a beautifully renovated antique estate where timeless character meets modern comfort. Centered around a paved courtyard and surrounded by classic outbuildings, the property offers a rare sense of privacy and charm.The main residence features four bedrooms and four-and-a-half baths. The first floor is comprised of the kitchen opening to the dining room, family room, and front-to-back living room. Flex space on both the second and third floor provide options for work, play or storage. Outdoors, enjoy a pool, fitness studio, and cabana. The centerpiece of the property is a striking pass-through barn, an architectural treasure that is as functional as it is impressive, offering multi-level space, underground parking for ten cars, and an attached seasonal living for guests or office. A legal, rentable guest house completes the setting, ideal for family, guests, or potential income. Sherborn has top ranked schools, Farm Pond and an extensive town trail system.

102 Washington St, Sherborn

Listing courtesy of Listing Agent: The Powissett Group from Listing Office: Compass.
$1,400,000
4 Beds ⋅ 3 Baths ⋅ 73487728 MLS
Located on 2 picturesque acres in premier, centrally located Sherborn neighborhood, this FULLY RENOVATED, METICULOUSLY MAINTAINED 4-bedroom colonial is MOVE-IN READY! The bright, open floor plan features a custom, eat-in kitchen w/walk-in pantry, opening to a family room w/gas fireplace & charming screened porch. Enjoy seamless indoor-outdoor living on the patio overlooking a private backyard w/direct trail access. Other highlights include: front to back living room w/wood burning fireplace, separate DR or home office, renovated baths, 4 generous sized bedrms, finished lower level adding addt’l living area w/ample storage, hardwood floors throughout, 2nd floor laundry, NATURAL GAS heat, central A/C, newer windows & brand new septic system! Experience the best of Sherborn offering top-tier schools, town beach, renowned trail system & easy access to commuter rail & Mass Pike & come fall in love with this perfectly sized, renovated home in coveted location, COME SEE... OH 3/29, 1:00-3:00!

84 Old Orchard Rd., Sherborn

Listing courtesy of Listing Agent: Laura Mastrobuono from Listing Office: Compass.
$1,500,000
5 Beds ⋅ 5 Baths ⋅ 73484509 MLS
ATTENTION BUYERS: this one-of-a-kind contemporary on 2 magical acres offers a completely renovated interior w/high-end finishes, 5 bedrooms & 5700 sqft for < $1.4M! Located in favorite Sherborn neighborhood but set well off the road, this home is a NATURE LOVER'S DREAM: w/soaring ceilings & walls of windows & sliders, offering stunning views of mature gardens & trees, bringing the outside in! The light filled open concept main level w/great room, kitchen, dining rm & large sunrm w/indoor grill is ideal for entertaining & everyday life; 2nd level includes 4 bedrms w/3 full baths; the lower, walk-out level includes add'l 5th bedrm, cozy den, rec room, mudrm, bathrm, laundry & garage. A bonus 4th floor loft provides an ideal home office. Located on quiet cul-de-sac just ~20 miles west of Boston in an idyllic town known for offering exceptional public schools, extensive trail system & easy access to commuter rail, COME SEE all this property has to offer!

15 Wildwood Drive, Sherborn

Listing courtesy of Listing Agent: Laura Mastrobuono from Listing Office: Compass.
$1,160,000
4 Beds ⋅ 4 Baths ⋅ 73482387 MLS
Don't miss this opportunity to own a private 5-acre retreat in a desirable Sherborn neighborhood with access to over 19 acres of surrounding conservation land and trails, including a scenic 1.6-mile loop. 59 Spywood Road is a 4-bedroom, 3.5-bathroom Colonial home offering a warm and inviting atmosphere with thoughtful interior updates throughout. Comfort meets versatility with generously sized bedrooms, welcoming living areas, a dedicated home office, and full laundry room. The updated kitchen with white cabinetry and tile, granite and butcher block countertops, and luxury vinyl plank flooring opens to a large deck overlooking peaceful natural surroundings, ideal for gathering and outdoor entertainment. Tasteful improvements complement the home's timeless character, while the expansive unfinished basement offers exceptional potential. Privacy, natural beauty, and recent updates come together in this special Sherborn offering!

59 Spywood Road, Sherborn

Listing courtesy of Listing Agent: Danielle Marino from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.

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