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16 Happy Hollow Road, Wayland
$995,000
4 Beds ⋅ 2 Baths ⋅ 73594514 MLS
Welcome home to this charming, meticulously maintained 4-bedroom, 2-bathroom classic Cape style house located in a highly desirable Wayland neighborhood. Set on a level lot with a private backyard and a large outdoor deck, this move-in ready home offers warmth, character, and thoughtful modern updates throughout.The main level features a spacious living room with a wood-burning fireplace and an updated eat-in kitchen overlooking the yard, alongside a large screened-in sunroom—ideal for everyday living and indoor-outdoor entertaining. The first-floor layout includes two bedrooms and one full bath, offering convenient main-level living.Upstairs, the second floor boasts two additional bedrooms, a versatile bonus room (perfect for a home office), and a second full bathroom.The finished basement lower level offers versatile bonus living space with fireplace, a dedicated laundry room, and direct access to the attached 2-car garage. Additional highlights include a new 2025 water heater and central air conditioning. Located within a 1/2 mile of top rated Wayland elementary, middle and high schools, near local shopping centers, and major commuting routes.

16 Happy Hollow Road, Wayland

Listing courtesy of Listing Agent: Nikki Milott McCay from Listing Office: Gibson Sotheby's International Realty.
38 Hawthorne Rd, Wayland
$935,000
4 Beds ⋅ 2 Baths ⋅ 73585965 MLS
SELLER CREDIT TOWARD A 1-0 BUYDOWN! Welcome to 38 Hawthorne Road. Exterior color in photo is virtual for marketing purposes only. This charming Garrison Colonial is nestled in the picturesque town of Wayland. A delightful four-bedroom, two-bath home offers the perfect blend of classic charm and modern convenience. Enjoy the comfort of central air, Gas radiant fireplace to keep you warm and toasty in the cool weather. The elegance of gleaming hardwood floors, and the fresh updates with new carpet on the second level and a fresh coat of paint throughout offer move-in ready features. Tucked away off the main roads and situated in a neighborhood setting, this home offers a great opportunity to be part of a desirable community. Conveniently located close to major routes like Route 9, Route 30, Mass Pike and right next to Dudley Pond. You’ll have easy access to a variety of shops, restaurants, and nearby Wayland Town Beach and Lake Cochituate. Plus, you’ll be part of a top-rated school system, making this home an ideal choice for families. Come and see 38 Hawthorne Road!

38 Hawthorne Rd, Wayland

Listing courtesy of Listing Agent: Diane Paolini from Listing Office: Coldwell Banker Realty - Sudbury.
89 Dudley Rd, Wayland
$1,235,000
4 Beds ⋅ 2 Baths ⋅ 73585071 MLS
Welcome to waterfront living on Dudley Pond, where every day feels like vacation. Set on a oversized lot, this is the kind of property that opens doors either way: move right into a spacious, already-established 4+ bedroom, 2-bath home, or use the rare 4-bedroom septic and large, usable yard to build the dream home you've been picturing. Whichever path you choose, the lifestyle is already waiting.Mornings start with coffee on the wraparound deck as mist lifts off the water. Afternoons are for casting a line from your private dock, launching paddle boards and kayaks, or relaxing on your own private beach area at the water's edge. Evenings bring glowing sunset views, and when the air turns crisp, the sauna overlooking the water becomes your own private spa. Keep an eye on the sky: bald eagles glide by right over your backyard.The magic lasts all year. Summer brings long days of swimming, fishing, and paddling. Fall paints the shoreline in brilliant color. Winter turns the view into a snow-dusted postcard best enjoyed from the warmth of the sauna, and spring brings the wildlife back right outside your door.Inside, generous living space offers room for guests, a home office, and weekend gatherings that spill out onto the deck. Outside, the oversized lot delivers a large, usable yard with space for gardens, lawn games, a fire pit, or the expansion or rebuild you've been dreaming of, all supported by that coveted 4-bedroom septic.Here, tranquility and convenience finally meet. Tucked away in one of Wayland's most sought-after communities, this home feels like a lakeside escape, yet it's just minutes to Route 30, Route 9, and the Mass Pike for an easy commute to Boston and beyond. Local favorites Dudley Chateau and the Villa are just around the corner for dinner out, along with nearby shopping and conservation trails.Live your best vacation life every day, with no packing, no traffic, and no check-out time. Close to the city but a world away, this is waterfront living at its finest. Move right in, renovate, or build new. Either way, your lakeside retreat awaits.

89 Dudley Rd, Wayland

Listing courtesy of Listing Agent: Victoria Anfuso from Listing Office: .
186 Main St Unit 2, Wayland
$5,400
5 Beds ⋅ 2 Baths ⋅ 73583285 MLS
Fully Gut renovated 5 bedroom in prime wayland location! Wonderful, two level unit with abundance of natural light! This light and bright unit offers 9 rooms with over 2000 sq.feet of living space and plenty of storage. The first level offers a huge eat-in kitchen with newer appliances including gas stove for cooking and large walk-in pantry, two large bedrooms, a nice size living room, a huge bathroom with brand new stackable laundry and an office space. The second level offers 3 bedrooms (electric baseboard heat) for in-home gym/studio/game room etc. & two large storage closets. The unit will be freshly painted and renovated for the next tenant! An amazing value for Wayland. Huge lot 3/4 Acre.

186 Main St Unit 2, Wayland

Listing courtesy of Listing Agent: Jacob Rosenberg from Listing Office: Red Tree Real Estate.
5 Mansion Rd, Wayland
$679,900
2 Beds ⋅ 2 Baths ⋅ 73575023 MLS
Enjoy Lake living in this Dudley Pond neighborhood! Close to Mansion beach, this two bedroom ranch blends cozy warmth w/nice updates, flexible layout, 2 full bathrooms & a 9,583 sq. ft. lot. Features include warm wood accents, a cozy fireplaced living room, 2 good sized bedrooms & a newly carpeted walk-out lower level which may serve as the 2nd bedroom, family room or hybrid office space - complete w/closets, a large storage room & economical utility bills! Step outside to your private outdoor retreat w/ an expansive finished deck w/ beautiful water views, a basketball patio, and two handy storage sheds. Enjoy public access to swimming, kayaking, winter skating on Dudley Pond & Wayland's favorite hang-out at Dudley Chateau across the pond! Minutes from Lake Cochituate, major commuter routes (Mass Pike, Rt 9, Rt 20) & premier MetroWest shopping. Enjoy both the recreation/outdoors and Metrowest urban living with Wayland's top-rated public school system! Be in your new home for the holidays! Lower monthly payments from day one - Seller is offering a temporary mortgage rate buy down TBD!

5 Mansion Rd, Wayland

Listing courtesy of Listing Agent: Nancy Antonio from Listing Office: Keller Williams Boston MetroWest.
8 Damon, Wayland
$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.
18 Lodge Road, Wayland
$734,000
2 Beds ⋅ 2 Baths ⋅ 73555539 MLS
An exceptional opportunity to own a beautifully maintained single-family home in Wayland! Tucked at the end of a quiet no-outlet road, this charming Colonial offers the privacy, outdoor space and freedom of homeownership in a manageable, move-in-ready package. A welcoming covered front porch opens to a bright, inviting floor plan centered around a wood-burning fireplace. The updated kitchen features cherry cabinetry, stainless appliances, granite countertops and an oversized butcher-block island perfect for gathering and entertaining. Upstairs, two spacious bedrooms feature soaring ceilings, skylights and generous closet space, including a walk-in closet in the primary, while a flexible bonus room is ideal for a home office, nursery or creative space. Outside, enjoy your own private retreat with a professionally designed pea-stone patio, lush fenced yard, vegetable gardens and fire pit—perfect for summer evenings and weekend entertaining. Minutes to Mansion Beach and Wayland Town Beach, this special home offers a rare opportunity to enjoy the space, privacy and lifestyle of single-family living in Wayland.

18 Lodge Road, Wayland

Listing courtesy of Listing Agent: Michael J. Ford from Listing Office: Coldwell Banker Realty - Framingham.
10 Willard St, Wayland
$674,999
3 Beds ⋅ 2 Baths ⋅ 73554382 MLS
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.
81 Riverview Cir, Wayland
$699,000
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..
167 Glezen Ln, Wayland
$898,000
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.
136 Commonwealth Rd, Wayland
$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.

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.

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