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$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.
$3,950,000
4 Beds ⋅ 6 Baths ⋅ 73514730 MLS
PRIVATE. ARCHITECTURAL. UNEXPECTED. Privately set on 4.9 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.
$2,195,000
6 Beds ⋅ 6 Baths ⋅ 73510940 MLS
Set on 3.5 picturesque acres, this exceptional 5,800+ sq. ft. estate offers a rare opportunity for multigenerational living. The flexible floor plan includes 6 bedrooms, 5.5 baths, 2 kitchens, 2 laundry areas, and a legally permitted accessory dwelling unit with private entrance. A thoughtfully designed ~2,000 sq. ft. single-level addition is ideal for aging parents, extended family, caregivers, or guests. Established gardens, fruit and berry plantings, open lawn areas, a 2.5-car attached garage, and 3-car detached garage complete this unique offering. An additional 2,800+ sq. ft. of unfinished lower-level space offers exceptional potential for a home theater, gym, recreation area, workshop, or future expansion. Available for the first time in over 50 years, this rare legacy property blends historic character, privacy, and exceptional versatility.

55 Glezen Ln, Wayland

Listing courtesy of Listing Agent: Peace Nguyen from Listing Office: Engel & Volkers Wellesley.
$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.

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