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$1,995,000
5 Beds ⋅ 4 Baths ⋅ 73574192 MLS
Set on approximately 2.07 private acres across two adjoining parcels, 5 Wildwood Road offers exceptional space, timeless character, and a thoughtfully designed layout. The expansive interior features generously sized living and entertaining areas, spacious bedrooms, and a dedicated primary suite wing that provides a peaceful sense of privacy. Warm architectural details add charm throughout, while the home’s impressive proportions offer flexibility for everyday living, working, and hosting. Surrounded by mature landscaping in a coveted neighborhood setting, this distinctive property presents a wonderful opportunity to enjoy space, privacy, and enduring character in the heart of Wayland.

5 Wildwood Road, Wayland

Listing courtesy of Listing Agent: Gina Anderson from Listing Office: MGS Group Real Estate LTD - Wellesley.
$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.
$2,100,000
5 Beds ⋅ 6 Baths ⋅ 73562911 MLS
Custom-built in 1999, this distinctive Wayland estate showcases exceptional craftsmanship, thoughtful design, and timeless architectural character. Generously proportioned rooms, quality construction, and unique details reflect the home’s original grandeur. While certain systems and finishes will require attention and thoughtful updates, the property presents a rare opportunity to restore and personalize a truly special residence in a desirable neighborhood. Being sold as is.

21 Jeffrey Road, Wayland

Listing courtesy of Listing Agent: Gina Anderson from Listing Office: MGS Group Real Estate LTD - Wellesley.
$4,200,000
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 - Wellesley.
$2,095,000
5 Beds ⋅ 5 Baths ⋅ 73514482 MLS
This stunning brand-new custom home built by MORRELL CONSTRUCTION boasts 4,102 sq ft of meticulously designed living space. The open-concept layout seamlessly blends style & functionality, offering the ideal setting for both everyday living & effortless entertaining. High-end materials & expert craftsmanship are showcased throughout—from the spacious gourmet kitchen to the refined living & dining areas, every detail reflects comfort, elegance, & sophistication. The chef-inspired kitchen is a culinary dream, with high end appliances, cabinets, & countertops. Kitchen offers a Thermador appliance package, including an induction cooktop, stainless steel hood insert, microwave drawer, 36" refrigerator & dishwasher. An additional. 2,066 sq ft in the unfinished basement perfect for storage, a home gym, or future expansion.

125 West Plain Street, Wayland

Listing courtesy of Listing Agent: TEAM Metrowest from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.
$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.
$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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