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226 Cochituate Rd, Wayland
$3,950,000
5 Beds ⋅ 7 Baths ⋅ 73548853 MLS
Extraordinary Shingle Style estate set on one of Wayland’s most spectacular private settings. Positioned on a hill overlooking sweeping lawns, a winding drive leads to a circular motor court with generous parking. Blending classic style with relaxed comfort, a grand open-concept living space flows from a chef’s kitchen to a family room, “laptop lounge,” and billiard room with wet bar. Upstairs, the luxurious primary suite includes walk-in closets, fireplace, balcony, and gorgeous spa bath. A private one-bedroom guest apartment is located above the 3-car garage. The third floor offers space for recreation, media, or remote work. Additional highlights include a spacious home gym and a resort-style backyard with covered porch, expansive deck with outdoor kitchen and bar, fire pit, putting green, saltwater infinity-edge pool and spa, all surrounded by lush grounds and specimen plantings. This special retreat offers the benefit of top-rated schools and easy access to Boston.

226 Cochituate Rd, Wayland

Listing courtesy of Listing Agent: The Joni Shore Group from Listing Office: Douglas Elliman Real Estate.
17 Deer Run, Wayland
$3,600,000
4 Beds ⋅ 6 Baths ⋅ 73514730 MLS
PRIVATE. ARCHITECTURAL. UNEXPECTED. Privately set on 3.5 wooded acres high above the surrounding landscape, 17 Deer Run is a one-of-a-kind custom contemporary offering exceptional scale, privacy and year-round resort-style living in Wayland. Floor-to-ceiling glass fills three expansive levels with natural light while capturing dramatic sunset views from an elevation of approximately 420 feet. At the heart of the residence is an extraordinary 20' × 60' heated indoor saltwater pool, overlooked by a mezzanine and surrounded by spaces designed for entertaining, recreation and relaxation. The flexible 10,007-square-foot floor plan offers four bedrooms, multiple living and gathering spaces, exterior access from each level and two fireplaces. Custom built by its original owner and meticulously maintained by the same family of builders, the property has never before been publicly offered for sale. A rare opportunity to experience architecture, acreage and amenities unlike anything else in Wayland.

17 Deer Run, Wayland

Listing courtesy of Listing Agent: Carol Stewart from Listing Office: Carol Stewart.
188 Glezen Ln, Wayland
$3,495,000
5 Beds ⋅ 7 Baths ⋅ 73502785 MLS
Exceptional 5-bedroom estate with over 7500 sq ft of living space set on 3.3 bucolic acres abutting conservation land blending timeless design with modern luxury and is a masterclass in craftsmanship for today’s discerning buyer. Elegant living and dining rooms flow into a chef’s kitchen with custom cabinetry, top-tier appliances, stonework, and an oversized island, opening to a warm family room with fireplace. Sunlit interiors feature expansive windows framing serene natural views. A home office and mudroom with built ins add everyday convenience. Upstairs are four spacious bedrooms, and three full baths including a dream primary retreat with a 2024 renovated spa bath. The WOW walk-out lower level includes a home theater, gym, playroom, wine cellar and au pair/in-law suite. Enjoy an expansive patio and level backyard, perfect for entertaining and play. 3-car garage. Prime location on the Weston line, minutes to commuting routes, Wayland Town Center, and top schools. A rare gem!

188 Glezen Ln, Wayland

Listing courtesy of Listing Agent: Denise Mosher from Listing Office: Coldwell Banker Realty - Weston.
4 Ellen Mary Way, Wayland
$3,475,000
6 Beds ⋅ 9 Baths ⋅ 73584864 MLS
Sited on a private 1.74 acre lot with breathtaking views abutting conservation land, this exquisitely designed home is built with impeccable exterior & interior finishes with endless amenities. This captivating home has been meticulously cared for with many new enhancements, providing a luxury experience for all. Chef’s Dream Kitchen equipped with custom cabinetry, oversized island, 2 dishwashers, 2 wall ovens & multiple refrigerators. Dramatic dining and living complemented by tall ceilings, radiant heat and 5 fireplaces throughout. 6 oversized bedrooms, ( 5 bedroom septic) 6 full and 3 half baths include a gorgeous 1st floor master suite with his/her closet & private baths. The lower level of the home offers spectacular indoor/outdoor living including a bar, billiard room, wine cellar, custom cabana with built in smoker & grill, industrial sized heaters, full kitchen, 2 fire places complete with a gym and indoor exercise pool/spa. The ultimate home for entertaining & luxury living.

4 Ellen Mary Way, Wayland

Listing courtesy of Listing Agent: Kara Apostolica from Listing Office: Gibson Sotheby's International Realty.
116 Lincoln Rd, Wayland
$2,450,000
4 Beds ⋅ 4 Baths ⋅ 73590956 MLS
Exceptional custom-built luxury new construction! Set on a private one-acre lot in one of Wayland’s most prestigious neighborhoods and is conveniently located near top-rated schools, conservation trails, shopping, dining, and major commuting routes. Offering over 5,670 sq ft of designer living space, this home showcases stunning architecture and premium finishes throughout. Wide-plank oak hardwood flooring, elegant custom millwork, soaring ceilings, and designer lighting make an amazing first impression. The stunning gourmet chef’s kitchen steals the show and features a full Thermador appliance package, custom cabinetry, quartz countertops, an oversized waterfall island, as well as a spacious walk-in pantry. The spectacular vaulted family room is highlighted by a dramatic floor-to-ceiling stone fireplace and walls of oversized windows overlooking the private backyard.The luxurious primary suite offers a spa-inspired bath with a modern freestanding soaking tub, oversized walk-in shower, double vanity, and an impressive custom walk-in dressing room with center island. The oversized three-car garage features beautiful epoxy flooring and leads to an amazing mudroom with custom built-ins. Additional highlights include the dedicated home office, a huge finished lower level, large covered front porch, Hardie plank siding, energy-efficient systems, a brand-new septic system, and professionally landscaped grounds with amazing privacy. This exceptional luxury home offers the perfect balance of luxury, privacy, and convenience.

116 Lincoln Rd, Wayland

Listing courtesy of Listing Agent: Rose Hall from Listing Office: Blue Ocean Realty, LLC.
55 Glezen Ln, Wayland
$2,195,000
6 Beds ⋅ 6 Baths ⋅ 73510940 MLS
Offered for the first time in more than 50 years, 55 Glezen Lane is the kind of property that can become part of a family’s story for generations. Set on 3.5 picturesque acres, this distinctive Wayland home offers something increasingly rare: the space and flexibility to bring the people you love closer while still giving everyone a place of their own. Spanning more than 5,800 square feet, the residence features 6 bedrooms, 5.5 baths, 2 kitchens, and 2 laundry areas. A thoughtfully designed, approximately 2,000-square-foot single-level addition with a legally permitted accessory dwelling unit and private entrance creates an exceptional setting for aging parents, extended family, caregivers, or guests, allowing for both connection and independence under one roof. Outside, established gardens, fruit and berry plantings, and sweeping lawns invite a slower rhythm of life: gathering around the table, tending the garden, playing on the lawn, or simply enjoying the privacy and beauty of the surrounding land. A 2.5-car attached garage and separate 3-car detached garage offer remarkable flexibility for vehicles, hobbies, collections, or workshop space, while an additional 2,800+ square feet of unfinished lower-level space provides exciting possibilities for recreation, fitness, a home theater, workshop, or future expansion. Rich with history, surrounded by nature, and designed to evolve with the people who call it home, 55 Glezen Lane offers more than space. It offers the opportunity to create a home where generations can gather, live, and make memories together for years to come.

55 Glezen Ln, Wayland

Listing courtesy of Listing Agent: Peace Nguyen from Listing Office: Engel & Volkers Wellesley.
30 Snake Brook, Wayland
$1,675,000
4 Beds ⋅ 3 Baths ⋅ 73559541 MLS
Move right into this fully redesigned and rebuilt home in Wayland’s coveted Daymon Farms, the kind of neighborhood you dream of, with a welcoming community and true cul-de-sac setting. Completely renovated with updated systems, roofing, and siding, and so much more! This residence offers the feel of new construction with timeless design and exceptional craftsmanship. Shops, restaurants, and all Wayland schools are within walking distance, while easy highway access adds everyday convenience. Inside, designer lighting, custom millwork, and premium finishes complement a sun-filled, open floor plan connecting the kitchen, dining, and living spaces. Sophisticated yet inviting, the home is equally suited to quiet evenings and lively gatherings. Beautiful landscaping and an expansive backyard provide space to relax, entertain, and play, while the existing in-ground pool offers the opportunity to create your own private outdoor retreat.

30 Snake Brook, Wayland

Listing courtesy of Listing Agent: Gina Anderson from Listing Office: MGS Group Real Estate LTD - Wellesley.
3 Emmeline Path, Wayland
$1,650,000
3 Beds ⋅ 3 Baths ⋅ 73594553 MLS
A rare opportunity to enjoy the comfort of newly constructed, single-family living with the ease of condominium ownership. Set in one of Wayland’s most desirable North Side neighborhoods, this exceptional home blends modern design, refined finishes, and thoughtful details. The open-concept floor plan features a chef’s kitchen with stainless steel appliances, gas cooking, abundant cabinetry and counter space, and an oversized island overlooking the expansive family room and formal dining room. The first-floor primary suite offers a walk-in closet and luxurious bath, creating a private and convenient retreat. Upstairs, two generously sized bedrooms, a full bath, and a versatile loft provide flexible living space. The finished lower level is ideal for a playroom, game room, home theater, and/or gym. Outdoor amenities include a welcoming front porch, rear patio, spacious, level yard, and mature landscaping. An attached two-car garage with EV charging capability adds convenience, while direct backyard access to the Rail Trail offers an exceptional connection to nature. Ideally located near top-ranked Wayland schools, shopping, dining, and commuter routes to Boston, this home offers the perfect balance of modern comfort, natural beauty, and low-maintenance living.

3 Emmeline Path, Wayland

Listing courtesy of Listing Agent: Denise Mosher from Listing Office: Coldwell Banker Realty - Weston.
3 Emmeline Path Unit 3, Wayland
$1,650,000
3 Beds ⋅ 3 Baths ⋅ 73594495 MLS
A rare opportunity to enjoy the comfort of newly constructed, single-family living with the ease of condominium ownership. Set in one of Wayland’s most desirable North Side neighborhoods, this exceptional home blends modern design, refined finishes, and thoughtful details. The open-concept floor plan features a chef’s kitchen with stainless steel appliances, gas cooking, abundant cabinetry and counter space, and an oversized island overlooking the expansive family room and formal dining room. The first-floor primary suite offers a walk-in closet and luxurious bath, creating a private and convenient retreat. Upstairs, two generously sized bedrooms, a full bath, and a versatile loft provide flexible living space. The finished lower level is ideal for a playroom, game room, home theater, and/or gym. Outdoor amenities include a welcoming front porch, rear patio, spacious, level yard, and mature landscaping. An attached two-car garage with EV charging capability adds convenience, while direct backyard access to the Rail Trail offers an exceptional connection to nature. Ideally located near top-ranked Wayland schools, shopping, dining, and commuter routes to Boston, this home offers the perfect balance of modern comfort, natural beauty, and low-maintenance living.

3 Emmeline Path Unit 3, Wayland

Listing courtesy of Listing Agent: Denise Mosher from Listing Office: Coldwell Banker Realty - Weston.
186 Main St, Wayland
$1,475,000
8 Beds ⋅ 3 Baths ⋅ 73592757 MLS
Welcome to a fully gut-renovated multi-family gem in the heart of Wayland- This dramatically transformed two-family (8bd/3ba, 3,201 sq ft) retains its 19th-century charm while offering today’s modern comforts. Inside, discover sleek, contemporary finishes across both units, with open layouts, new kitchens featuring stainless appliances and designer cabinetry, spa-like bathrooms, updated electrical, plumbing, and ductless HVAC systems for year-round comfort. Ideal for owner-occupants or investors alike, this property boasts flexible unit configurations—first floor offering 3 beds with in-unit laundry and pantry access to a bright living area; second/third floor offers a spacious eat-in kitchen, separate living and dining areas, an office, plus 4/5 bedrooms and 2 full bathrooms. Set on an expansive 0.72-acre lot (30,000+sq ft), enjoy ample off-street parking for up to 8 vehicles, a shared deck, large yard. Unit 1 rented till 1/31/2026 for $3200

186 Main St, Wayland

Listing courtesy of Listing Agent: Jacob Rosenberg from Listing Office: Red Tree Real Estate.
202 Boston Post Rd, Wayland
$1,399,900
6 Beds ⋅ 4 Baths ⋅ 73565249 MLS
Set back from Boston Post Road, just steps from historic Wayland Center, this impressive Colonial has been completely and thoughtfully re-imagined. Rebuilt and renovated from top to bottom, the home boasts many high-tech, health/safety, and energy-efficiency features, including fully owned solar, Tesla charging port, wired surround sound, and reverse osmosis water treatment. Outside, the large, well-landscaped yard offers privacy and tranquility, while also directly abutting the Mass Central Rail Trail, connecting you to Cambridge and Boston, the north and south shores, and the Berkshires, by foot or bicycle. Dream of commuting to work on your bike? Here, you can! Inside, the feel and design of the floor plan is open and modern. The oversized kitchen with custom cabinetry, granite countertops, stainless appliances, and large island with seating opens perfectly to both the giant formal dining room and the large fireplaced living room. The family room leads directly to the well-equipped exercise room, which also has separate access from outside. A cozy office/bedroom and strategically located half bath complete the first floor loving spaces. Upstairs, five ample bedrooms and three full bathrooms include a grand vaulted-ceilinged primary with gorgeous en-suite full tiled bath and large walk-in closet. A separate laundry room is located off the main upstairs hall. Hardwood and tile floors throughout, central heat and A/C, new metal roof!...and so much more. The two car garage with attached carport for a third vehicle is part of a larger outbuilding that also includes a vast workshop area that could easily be converted in to an ADU. And, the heated driveway ensures minimal shoveling, snow blowing, or plowing! This nearly two-acre property also has the very real potential of being an equestrian property, with its large back yard and direct connection to the Mass Central Rail Trail! There's simply too much to list. No expense was spared in this masterful renovation, and it must be seen in person to be fully appreciated. Wayland is one of MetroWest's most desired towns. Boston and Worcester are both easily commutable...even by bicycle!

202 Boston Post Rd, Wayland

Listing courtesy of Listing Agent: Richard Wilcox from Listing Office: Distinctly New England.
201 Boston Post Rd, Wayland
$1,399,000
4 Beds ⋅ 4 Baths ⋅ 73585217 MLS
Young 2014-built Colonial offering 4,268 sq ft of finished living space, 4 bedrooms, and 3.5 baths on a level 0.69-acre lot. The bright, open main level features hardwood floors, a spacious family room with gas fireplace, formal living and dining rooms, and a white kitchen with granite countertops, stainless steel appliances, and direct access to the backyard. Upstairs, the primary suite offers two walk-in closets with custom built-ins and a private bath with whirlpool tub and tiled shower. A second bedroom features its own private bath and sitting area, while two additional bedrooms share a Jack-and-Jill bath. The finished lower level adds approximately 1,200 sq ft with a home office, media room, game room, and additional flexible space. Outside, enjoy a fenced, level backyard with patio and firepit. Additional features include second-floor laundry, central air, central vacuum, sprinkler system, tankless hot water, a 2-car attached garage, and fully owned Tesla solar panels.

201 Boston Post Rd, Wayland

Listing courtesy of Listing Agent: Ning Sun from Listing Office: United Real Estate, LLC.
26 Millbrook Rd, Wayland
$1,365,000
5 Beds ⋅ 3 Baths ⋅ 73588892 MLS
A rare opportunity to own one of Wayland's iconic Victorian homes—thoughtfully updated while preserving the elegance and craftsmanship of the original 1880 design. Period details, intricate woodwork, bullseye oak moldings, and beautiful hardwood floors are complemented by extensive recent improvements, including 20 new windows, a renovated kitchen with new cabinetry, flooring, and backsplash, updated flooring and ceiling fans in all five bedrooms, refreshed bathrooms with new vanities, a tankless water heater, and more. The welcoming floor plan offers a grand foyer, fireplaced parlor, formal dining room, private office, expansive family room, and a secluded third-floor primary suite with sitting room and bath. Set on a beautifully landscaped 37,000± sq. ft. lot tucked back from the road, this exceptional property offers privacy just moments from Wayland Center, top-rated schools, the library, and the Mass Central Rail Trail.

26 Millbrook Rd, Wayland

Listing courtesy of Listing Agent: Pamela Taylor from Listing Office: LAER Realty Partners.
175 Pelham Island Road, Wayland
$1,350,000
4 Beds ⋅ 4 Baths ⋅ 73549330 MLS
Nature lovers will love this private retreat abutting acres of conservation land. The expansive backyard offers beautiful views and direct access to nature, while the stunning 27' x 24' family room addition is designed to take full advantage of the peaceful setting. Enjoy nearby Heard Pond for kayaking or hiking. The main level also features a kitchen, dining room, and spacious family room overlooking the backyard. Upstairs, the primary suite addition offers a walk-in closet, two additional closets, and an ensuite bath with serene views, along with two additional bedrooms and an updated hall bath. A separate back staircase leads exclusively to a large 4th bedroom above the family room-also ideal for a private home office, guest suite, or studio. A 3-car garage opens to a large mudroom, laundry room and full bath. The lower level includes a playroom and unfinished bonus space. New 4-bedroom septic (2026), gas heat, roof (2020). Minutes to Route 20 for easy commuting and shopping.

175 Pelham Island Road, Wayland

Listing courtesy of Listing Agent: The Semple & Hettrich Team from Listing Office: Coldwell Banker Realty - Sudbury.
3 Tally Ho Ln, Wayland
$1,275,000
3 Beds ⋅ 3 Baths ⋅ 73577826 MLS
Exceptional opportunity for discerning buyers! Beautifully gut-renovated ranch-style home offering comfortable one-level living with thoughtfully finished additional space in a desirable Wayland neighborhood. Set on approximately 0.47 acres, this stunning home welcomes you with an open, inviting layout and an abundance of natural light. The spacious living room features a cozy fireplace and flows seamlessly into the dining area, creating the perfect setting for both everyday living and entertaining. The beautifully renovated kitchen is the heart of the home, thoughtfully designed with a perfect balance of style and functionality. A large skylight and generously sized windows fill the space with natural light, while abundant recessed lighting adds warmth and ambiance throughout. The kitchen opens directly to the large deck, making indoor-outdoor entertaining effortless. Three well-proportioned bedrooms offer generous closet space, including a comfortable primary suite with a beautifully appointed spa-like bathroom—a peaceful retreat at the end of the day. Two additional full bathrooms provide exceptional convenience for family and guests. The freshly finished, walk-out lower level significantly expands the home's versatility, offering flexible space for a home office, gym, recreation room, guest area, or playroom. With excellent natural light and direct outdoor access, this level can easily adapt to a variety of needs and lifestyles. Step outside to discover your own private backyard oasis. The spacious deck is ideal for summer dining, entertaining, or simply enjoying a quiet morning coffee, while the approximately 0.47-acre lot provides plenty of room to relax, play, and garden.Additional highlights include a one-car garage, multiple-zone central air and exceptional move-in-ready condition. Ideally located in the sought-after Cochituate area of Wayland, with convenient access to highly regarded schools, shopping, restaurants, conservation areas, commuter routes, and all that Wayland has to offer. Beautifully renovated, thoughtfully designed, and ready to enjoy—nothing to do but move in and make it your own!

3 Tally Ho Ln, Wayland

Listing courtesy of Listing Agent: Anya Kogan from Listing Office: Luxury Realty Partners.
44 Pequot Rd, Wayland
$1,225,000
3 Beds ⋅ 3 Baths ⋅ 73588162 MLS
More space, flexibility, and possibility than meets the eye. Tucked into a wonderful Wayland neighborhood with sidewalks and an easy walk to the schools, 44 Pequot Road is the kind of home that may surprise you. Behind its understated exterior is a remarkably flexible three-bedroom, three-bath layout with room to gather, work, host, and grow. The main level feels bright and welcoming, with a fireplaced living room, dining room, and kitchen. A desirable southern rear exposure brings beautiful natural light throughout the day and creates a warm connection between the house and the backyard. With 2 bedrooms and 2 full baths on this level, the home also offers the possibility of comfortable single-level living. Downstairs, the walk-out lower level adds an entirely different dimension to the home. A spacious family room provides a relaxed place for movie nights, play, or everyday living, while a third bedroom, full bath, and separate office offer privacy and flexibility for guests, working from home, or multigenerational needs. And then there is the backyard. Expansive, sunny, and wonderfully private-feeling, it offers the kind of space that invites you outside. A beautiful brick patio surrounded by stone walls is ready for summer dinners, morning coffee, and evenings with friends, while the large lawn leaves plenty of room for play, gardening, or simply enjoying the outdoors. A shed provides extra storage, and the two-car garage has brand-new garage doors. The location makes everyday life especially easy. Walk to Wayland's schools, including nearby Happy Hollow Elementary, while enjoying a neighborhood with sidewalks and a quieter residential street. Bright, flexible, and much more spacious than its exterior suggests, 44 Pequot Road is a home that can adapt beautifully to different stages of life, with the space to enjoy today and the flexibility to serve you for years to come. Recent improvements include a newer roof (2022), hot water tank (2025), and front entry and garage doors (2026), offering added value and peace of mind.

44 Pequot Rd, Wayland

Listing courtesy of Listing Agent: Peace Nguyen from Listing Office: Engel & Volkers Wellesley.
89 Dudley Rd, Wayland
$1,196,000
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: .
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.
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.
9 Training Field Road, Wayland
$1,095,000
3 Beds ⋅ 3 Baths ⋅ 73593972 MLS
Beloved and meticulously maintained family home of nearly 70 years is awaiting its next chapter. Located in the desirable Claypit Hill neighborhood, the home has seen many thoughtful improvements and three additions over the years, including an oversized two-car garage. This turnkey home is ready to enjoy now, yet a few cosmetic updates and your personal design vision could make it a true showstopper. Holiday hosting is simplified by the massive kitchen, well-appointed with copious cabinets, counter space, two sinks, two ovens and a countertop gas range. Spread out in the family room, dining room, wet bar, and living room with wood-burning fireplace and triple box window providing an abundance of natural light. On the main level, the flexible layout offers a primary en-suite with double closets, soaking tub and direct yard access, plus a bonus office or 4th bedroom. Ascend to the second floor where you'll discover two more bedrooms with gorgeous fir hardwood floors, ample closets, and a spacious full bathroom with tiled shower and tub. Three basement areas provide tons of storage or the possibility for expansion. Outside, multiple composite decks & covered porches overlook the stunning 1/2-acre property enveloped in mature trees and perennial garden beds. Ultimate location provides proximity to the center of town, restaurants, groceries, shops, rail trail and public library.

9 Training Field Road, Wayland

Listing courtesy of Listing Agent: Christian Iantosca Team from Listing Office: Arborview Realty Inc..
104 Dahlia Drive Unit 104, Wayland
$1,050,000
2 Beds ⋅ 4 Baths ⋅ 73584084 MLS ⋅ ['The Meadows'] BLDG.
THE MEADOWS: THE Meadows is a lovely, high desirable condo community in convenient South Wayland. The Preston floor plan features a roomy kitchen, open living-dining room, primary bedroom ensuite, laundry room, and guest bath on the first floor. The spacious upper floor features a second bedroom, large bonus room with a walk in closet, charming loft space and full bath. Lower level is walkout and has numerous rooms that offer great flexibility. (office, game room, library) This unit is bright and sunny and offers an easy lifestyle in a well kept, lovely community.

104 Dahlia Drive Unit 104, Wayland

Listing courtesy of Listing Agent: Leeann Yolin from Listing Office: Coldwell Banker Realty - Weston.
6 Aqueduct Rd, Wayland
$1,029,721
3 Beds ⋅ 3 Baths ⋅ 73593706 MLS
Welcome to 6 Aqueduct Rd, a beautifully updated 3-bedroom and den that can be used as extra bedroom, 2.5-bathroom split-level home nestled in one of Wayland's most inviting residential neighborhoods! Situated just minutes from major commuting routes and shopping, this unique property offers a rare blend of modern convenience and natural serenity, featuring a private backyard that directly abuts the scenic Hultman Aqueduct Trail.Step into the welcoming foyer and immediately notice the bright, inviting ambiance. The heart of the home is the newly renovated, stunning kitchen- thoughtfully designed with pristine stainless steel appliances, a built-in wall oven, a gas stove with a sleek range hood, a dishwasher, modern recessed lighting, and a spacious center island. This culinary space flows seamlessly into the dining room and a cozy family room anchored by a beautiful fireplace, providing the perfect layout for entertaining or everyday living.A standout feature of this property is the newly constructed addition, offering a versatile space that makes an ideal home gym, private office, or bonus room to suit your lifestyle. In the lower living area, natural light pours in through two sliding glass doors that open directly onto your peaceful backyard oasis.All three bedrooms are conveniently located on the top floor, and den that can be used as extra bedroom featuring durable and stylish vinyl flooring that beautifully complements the home's fresh, vibrant paint scheme. For your convenience, a walk-up attic provides abundant and easily accessible storage space.With its stunning recent upgrades, flexible living spaces, and unparalleled access to nature, this home is truly turn-key. Don't miss your chance to make this exceptional Wayland house your new home!

6 Aqueduct Rd, Wayland

Listing courtesy of Listing Agent: Albeiro Lopera from Listing Office: United Brokers.
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
$920,000
4 Beds ⋅ 2 Baths ⋅ 73585965 MLS
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.
26 Red Barn Rd, Wayland
$889,900
3 Beds ⋅ 3 Baths ⋅ 73592383 MLS
WHAT A GREAT OPPORTUNITY to bring this home back to life!!! Large bedrooms...open sunny living room-dining room with fireplace...basement appears to have had an operational daycare in the past...the back yard is large and has an in-ground pool for summer fun!OUR SELLER REQUIRES OFFERS TO BE SUBMITTED HERE: click or paste this link into your web browser: https://agent.res.net/Offers.aspx?-1805749

26 Red Barn Rd, Wayland

Listing courtesy of Listing Agent: Nilton Lisboa from Listing Office: Lisboa Realty.
7 Castle Gate Road, Wayland
$849,000
2 Beds ⋅ 3 Baths ⋅ 73590323 MLS
Built in 2005, this move-in ready home features three rooms on the second floor with newly refinished hardwood floors, including a primary bedroom, second bedroom, and a versatile third room ideal for a home office, nursery, or guest space. The spacious primary suite offers a cathedral ceiling, skylight, walk-in closet, and private bath. A second bedroom, flexible third room, and full hall bath provide the space and versatility today's buyers are looking for. The main level features newly refinished hardwood floors throughout and a welcoming open-concept layout designed for comfortable living and entertaining. The family room offers French doors leading to a deck and flows seamlessly into the dining area and kitchen. The kitchen is well-equipped with abundant cabinetry and a center island with seating, while a convenient first-floor powder room completes the level. Tucked away in a quiet neighborhood, residents enjoy access to Dudley Pond at the end of the street, perfect for kayaking, canoeing, fishing, and relaxing by the water. The expansive "field of dreams" backyard provides endless opportunities for entertaining, recreation, gardening, or play. Additional highlights include a two-car garage, efficient natural gas heat, and a fantastic location with easy access to Lake Cochituate, shopping, dining, and major commuting routes. A wonderful opportunity to enjoy flexible living space, modern amenities, and an exceptional outdoor setting. The home is served by and deeded for a two-bedroom septic system, although there are three rooms upstairs. Hot water tank 2026.

7 Castle Gate Road, Wayland

Listing courtesy of Listing Agent: The Semple & Hettrich Team from Listing Office: Coldwell Banker Realty - Sudbury.
37 Winter St, Wayland
$849,000
4 Beds ⋅ 3 Baths ⋅ 73585445 MLS
Nestled on a quiet street in the heart of Cochituate, this versatile 4-bedroom, 3-full-bath Cape offers an exceptional blend of comfort, character & flexible living space. The main level features a light-filled living room with a cozy fireplace & large picture window, a formal dining room, and an eat-in kitchen with stainless steel appliances & gas cooking. A first-floor bedroom and full bath offer added flexibility, while the laundry/mudroom provides direct access to the two-car garage and outdoor living areas. Upstairs are two generously sized bedrooms and an additional full bath. Adding even more flexibility is a separate in-law apartment complete with a bedroom, kitchenette, full bath & private slider opening to the backyard. Set on a peaceful, private lot, the expansive outdoor living area is a true highlight, featuring a large patio, covered entertaining space, koi pond, natural wood sauna and extensive vegetable & flower gardens. Recent updates include a 2019 furnace, 2019 Navien tankless water heater & 2021 roof. Ideally located near major commuter routes with easy access to shopping, dining, recreation & all that MetroWest has to offer.

37 Winter St, Wayland

Listing courtesy of Listing Agent: Maura Rodino from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.
86 Oxbow Rd, Wayland
$799,000
73581250 MLS
Rare opportunity to build in desirable Wayland near the Lincoln line. This 2.08± acre residential parcel offers approximately 210 feet of frontage and extensive engineering and site-planning work already completed. Plans contemplate a substantial single-family residence with on-site septic and municipal water. Perc testing and soil evaluations for proposed on-site sewage disposal were performed May 12, 2022. Engineering package includes certified plot plan, septic/site planning and comprehensive stormwater design. Convenient location with access to Wayland schools, major routes and surrounding conservation and recreational amenities. Buyer and buyer's agent to perform all due diligence regarding proposed plans, permitting and intended use.

86 Oxbow Rd, Wayland

Listing courtesy of Listing Agent: Richard Kim from Listing Office: Keller Williams Realty Boston Northwest.
91 Hillside Dr Unit 91, Wayland
$799,000
2 Beds ⋅ 3 Baths ⋅ 73563132 MLS ⋅ ['The Hills At Mainstone'] BLDG.
Experience the perfect balance of comfort, convenience, and community at The Hills at Mainstone. Set among meticulously landscaped grounds and bordered by conservation land, this highly sought-after Wayland neighborhood offers resort-style amenities, including a clubhouse, heated swimming pool, basketball, tennis and pickleball courts. Enjoy weekly social gatherings and monthly social events or simply relax and appreciate the ease of low-maintenance living. This "B" style unit offers a thoughtfully designed floor plan with sun-filled living spaces, a well appointed kitchen with stainless steel appliances and granite countertops, hardwood floors, a gas fireplace, and a private deck overlooking peaceful surroundings. Upstairs, two spacious en-suite bedrooms each offering walk-in closets, while the partially finished lower level provides flexible space for a home office, gym or media room. Professionally managed and pet-friendly, The Hills recently underwent extensive capital improvements, including new roofs, siding, windows, skylights, sliders, decks, fencing, and renovated clubhouse facilities. Don't miss this opportunity.

91 Hillside Dr Unit 91, Wayland

Listing courtesy of Listing Agent: The Shulkin Wilk Group from Listing Office: Compass.
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.

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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