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$939,000
4 Beds ⋅ 2 Baths ⋅ 73575603 MLS
Four bedroom Colonial tucked away on a cul-de-sac in one of Wayland’s most desirable neighborhoods. This home features an exceptional floor plan with a seamless flow connecting the kitchen, dining area, and a living room centered by a fireplace—perfect for everyday living and entertaining. The main level provides ultimate flexibility with an extra bonus room ideal for a home office or mudroom, a newly renovated half bath, and direct access to the attached 2-car garage. Upstairs find four bedrooms and a beautifully updated full bathroom. Full basement with exterior access. Beautiful private backyard. Enjoy an unbeatable location close to Happy Hollow School and Wayland High School, local tennis/basketball courts, the community pool, and major commuter routes.

39 Rolling Lane, Wayland

Listing courtesy of Listing Agent: Nikki Milott McCay from Listing Office: Gibson Sotheby's International Realty.
$860,000
2 Beds ⋅ 2 Baths ⋅ 73575023 MLS
OPEN HOUSES Sat (9/12) 12-2pm Sun(9/13)2-4pm.Tucked away in Wayland’s peaceful Dudley pond neighborhood, this charming single-family ranch perfectly blends cozy charm w/ exceptional modern updates.Offering 2 bedrooms, 2 full bathrooms & 1,540 square feet of inviting living space, this property is ideal as a year-round sanctuary, an "active lifestyle" downsizing option w/possible expansion on its 9,583 sq ft lot.Inside, the home radiates warmth & comfort, featuring beautiful wood accents, a fireplaced living room, & a bright layout designed to maximize natural light. The newly carpeted, versatile lower level provides additional living space w/ an easy walk-out access to the driveway with two dedicated storage rooms. Outside, your private backyard oasis awaits—complete w/ two sheds, a basketball patio & an expansive finished deck offering peaceful & great views of the water.Live the ultimate MetroWest lifestyle with direct access to Dudley Pond for year-round recreation, including swimming, kayaking, fishing, and skating. You are just moments from the nearby Lake Cochituate, local conservation land, and scenic hiking trails. This property is a hidden retreat & a commuter’s dream with effortless access to the Mass Pike (I-90), Route 9 & Route 20. Enjoy the absolute best of both worlds w/ premier shopping, dining & Wayland's top-rated public school system all just minutes from your front door!

5 Mansion Rd, Wayland

Listing courtesy of Listing Agent: Nancy Antonio from Listing Office: Keller Williams Boston MetroWest.
$1,195,000
5 Beds ⋅ 2 Baths ⋅ 73573385 MLS
SHOWINGS START AT THE OPEN HOUSE SUNDAY SEPTEMBER 13, 12:30 TO 1:45 PM * Fantastic Wayland Two-Family | Lead Compliance Certificate in Hand Exceptional opportunity in a prime Wayland location! This well-maintained two-family offers flexibility for investors, owner-occupants, or multigenerational living—just steps to top-rated schools, shops, and restaurants.* Unit 1 features a bright, open floor plan with two bedrooms plus a den, offering flexible living space. Enjoy a private, sun-filled setting with an additional finished lower-level room ideal for a home office, gym, or media space. Laundry is located in the basement. * Unit 2 is renovated and spread across two levels with three to four bedrooms. Highlights include a new kitchen with updated cabinets and appliances, modern bath, engineered hardwood floors, and fresh paint throughout. Ample closets and natural light complete the space. Oversized .55 acre fenced yard, ample off-street parking, and shared laundry. Convenient to Routes 27, 9, Mass Pike, and Cochituate State Park.

8 Damon, Wayland

Listing courtesy of Listing Agent: John McHugh Real Estate Group from Listing Office: Coldwell Banker Realty - Wellesley.
$800,000
1 Beds ⋅ 2 Baths ⋅ 73555734 MLS ⋅ ['The Hills At Mainstone'] BLDG.
Welcome to The Hills at Mainstone! This beautiful, sun-filled townhouse offers a perfect, flexible layout. The first level features an open floor plan with a renovated kitchen, a fireplace living room, a full bath, and a separate room—perfect as a home office, den, or convenient first-floor bedroom—with views of a private courtyard. The dining room with soaring cathedral ceilings opens directly to a deck overlooking a conservation area. Upstairs, the private second-level primary en-suite comes complete with a walk-in closet, laundry, and an updated spa-like bath. The finished lower level offers bonus space—perfect as a second home office, family room, gym, or storage. Two-car garage. This beautifully maintained complex offers resort-style amenities including professional landscaping, a clubhouse, a swimming pool, and pickleball/tennis courts. Enjoy nearby walking trails and easy access to major highways and shopping.

93 Hillside Drive Unit 93, Wayland

Listing courtesy of Listing Agent: Nikki Milott McCay from Listing Office: Gibson Sotheby's International Realty.
$734,000
2 Beds ⋅ 2 Baths ⋅ 73555539 MLS
Impeccably maintained Colonial tucked at the end of a no-outlet road, offering privacy while convenient to shopping and major routes. A covered front porch welcomes you into a bright, open floor plan centered around a wood-burning fireplace. The updated kitchen features cherry cabinetry, stainless appliances, granite countertops and an oversized butcher-block island. Step outside to a professionally designed pea-stone patio overlooking a lush, fenced yard with vegetable gardens and fire pit—perfect for outdoor entertaining. Upstairs are two generously sized bedrooms with soaring ceilings, skylights and ample closet space, including a walk-in in the primary. An updated full bath plus flexible study/nursery/WFH space complete the second floor. Minutes to Mansion Beach and Wayland Town Beach, this inviting home combines charm, privacy and convenience.

18 Lodge Road, Wayland

Listing courtesy of Listing Agent: Michael J. Ford from Listing Office: Coldwell Banker Realty - Framingham.
$674,999
3 Beds ⋅ 2 Baths ⋅ 73554382 MLS
***OPEN HOUSE Sunday 8/30 12:30-1:30pm!*** $50K PRICE DROP! Opportunity awaits in sought after Wayland, one of Greater Boston’s most desired and affluent suburban communities! Tucked away on a quiet side street, this 3 bedroom, 2 bath single family home offers 2,460 square feet of living space and incredible potential. Built in 1880, the home features generously sized rooms throughout and a flexible layout ready for renovation and restoration. In need of repairs and updates, this property is perfect for contractors, investors or buyers looking for a fixer-upper project. A rare opportunity to own a home in a highly coveted community at an attractive price point and build instant equity with the right improvements.

10 Willard St, Wayland

Listing courtesy of Listing Agent: Catherine Walsh from Listing Office: Coldwell Banker Realty - Easton.
$759,000
3 Beds ⋅ 2 Baths ⋅ 73553802 MLS
Rare Opportunity: Classic Wayland Home Bordering Great Meadows Wildlife Refuge! Nestled on a highly coveted lot backing directly into the protected acreage of the Great Meadows National Wildlife Refuge, this home offers the perfect blend of natural tranquility and suburban convenience. Spanning over 2,000 square feet, this 3-bed, 2-bath home features an expansive layout and pristine views of the Sudbury River basin. The vaulted master bedroom with hardwood floors looks right over the scenic Refuge. The house includes a bonus room (which can be used as a nursery or office), an office nook, as well as a screened 3-season porch that is ready to become a 4-season gem. From this premium location, enjoy top-tier Wayland Public Schools, easy access to commuter routes into Boston, and a peaceful street perfect for quiet evenings, contemplative walks, or fun family time. Secure your slice of Wayland retreat!

81 Riverview Cir, Wayland

Listing courtesy of Listing Agent: Darin Thompson from Listing Office: Stuart St James, Inc..
$829,900
3 Beds ⋅ 2 Baths ⋅ 73547813 MLS
Situated in one of Wayland's most picturesque settings, 10 Mayflower Path offers a rare opportunity to enjoy luxury and privacy just steps from Dudley Pond. New construction in 2014, this 3-bedroom, 2-bath bungalow showcases exceptional craftsmanship & design. The open-concept main level features a beautifully appointed kitchen with granite countertops, stainless steel appliances, ample cabinetry, and a cozy dining island. Gleaming hardwood floors with a custom border inlay flow seamlessly into the sun-filled living room. The first floor also offers a primary bedroom, modern full bath, and convenient laundry. Upstairs, you'll find two generously sized bedrooms and another modern full bath. Outside, enjoy a generous fenced backyard with a storage shed. Additional features include a french drain & being part of the community at Dudley Pond Association. Ideally located just moments from scenic walking trails, schools, and community amenities like the town pool & tennis/basketball courts!

10 Mayflower Path, Wayland

Listing courtesy of Listing Agent: Michael Giovangelo from Listing Office: Better Living Real Estate, LLC.
$925,000
4 Beds ⋅ 2 Baths ⋅ 73545636 MLS
Welcome to this classic four-bedroom Cape set directly across from protected conservation land, offering peaceful views and a rare sense of privacy. A welcoming front porch overlooks the natural landscape, creating the perfect spot to enjoy quiet mornings or unwind at the end of the day. Inside, the home features two full baths with two bedrooms on the first level and 2 on the second floor. Office space optional in one of the first floor bedrooms. Partially finished basement with carpet and heat. This home needs a little TLC and updating, but the bones are solid and the potential is tremendous. Hardwood on first floor and upper hallway and stairs. Newer electrical 200 amps. Newer roof, all new paint 2026, new carpet in family room and upstairs bedroom. Newer windows in most rooms and new sliders in family room. Ideal for buyers looking to customize a home in a premier location. The backyard extends to the stream, providing a serene natural backdrop. Located within the top-rated Wayland school system, this home offers an exceptional opportunity to invest in a sought-after community known for its education. Come create your dream home in one of Wayland's most desirable settings.

167 Glezen Ln, Wayland

Listing courtesy of Listing Agent: Diane Paolini from Listing Office: Coldwell Banker Realty - Sudbury.
$1,099,999
5 Beds ⋅ 2 Baths ⋅ 73456437 MLS
Presenting 136 Commonwealth Road, Wayland, Massachusetts — a rare opportunity to own a fully renovated multi-family residence in one of Wayland’s most desirable locations. This exceptional property combines timeless charm with modern updates, offering over 3,000 sq. ft. of living space on a generous ½-acre lot. The home features two spacious units, each thoughtfully designed with light-filled interiors and contemporary finishes. With two full bathrooms. The roof is less than 5 years old. Septic less than 3 years old. New Electric heat; 7 zones in each unit. New Electric Hot water. Kitchen, baths, appliances, floors all new this income-generating property is ideal for investors or owner-occupants seeking flexibility and value. Enjoy the convenience of a prime location just steps from Starbucks, Walgreens, grocery stores, banks, and restaurants, and minutes from Route 9, the Mass Pike, and the premier shopping and dining at Natick Collection.

136 Commonwealth Rd, Wayland

Listing courtesy of Listing Agent: John McHugh Real Estate Group from Listing Office: Coldwell Banker Realty - Wellesley.

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