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$3,950,000
4 Beds ⋅ 6 Baths ⋅ 73514730 MLS
This outstanding contemporary home is set on 4.9 acres with breathtaking sunset views from 420' above sea-level. Living areas showcase floor to ceiling glass on three expansive levels. The floor plan flows seamlessly from the main living level to the lower level to the mezzanine above the 20' x 60' indoor heated salt water pool. Each level has access to the exterior grounds. Your own personal oasis year-round! First time on market since being custom built by original owner. Maintained by the same family of builders since constructed. Updates include Primary bedroom addition 2000; Foyer addition 2010; New Septic 2015; New flooring for foyer, office, living, dining, kitchen, main level hall, and pool-surround level 2026. A rare opportunity to own this well-cared-for true contemporary home!

17 Deer Run, Wayland

Listing courtesy of Listing Agent: Carol Stewart from Listing Office: Carol Stewart.
$2,145,000
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.
$2,295,000
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.
$1,649,000
2 Beds ⋅ 4 Baths ⋅ 73499807 MLS ⋅ ['River Trail'] BLDG.
Spectacular Custom Designed River Trail Townhouse. It's all in the details. Expansive 2 bedroom plus, 3.5 bath with the feel of a private home. You enter the sun-filled open concept level with a welcoming foyer, powder bath, designer layout chefs kitchen featuring custom cabinetry, additional bar area with wine refrigerator, Subzero refrigerator, upgraded appliances, large island leading to a casual dining/seating are with direct patio access. Your fireplaced Living Room and formal Dining Room complete this main level. Your second level boast a spacious open office/den/sitting area, laundry Room, large closet/storage space and full bath. The Primary suite features large walk in custom closet with dressing area, ensuite with custom oversized double shower and relaxing sleeping area. The second large bedroom is spacious with a double closet and extra storage. Lower level features full bath, family/exercise room and bedroom/office including large storage closets.

41 Lillian Way Unit 41, Wayland

Listing courtesy of Listing Agent: Cary Berger from Listing Office: Coldwell Banker Realty - Newton.
$1,194,000
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.
$635,000
73445245 MLS
Rare Dudley Pond opportunity — now confirmed buildable by the Wayland Building Commissioner. This approved .85-acre parcel offers unobstructed 360-degree water views, deeded direct water access, and private dock rights on a lot assembled from 12 original subdivision parcels. In January 2026, a formal written determination confirmed 108 Dudley Road is buildable for a single-family home without special permits or zoning relief under MGL Chapter 40A, Section 6. Perc test, septic design, topographical map, land survey, and subdivision approval are complete and on file—ready for your builder. An Accessory Dwelling Unit (ADU) may also be permitted, offering flexibility for guests, in-laws, or a caretaker. Includes a rare deeded right to build a waterfront storage structure near the dock—ideal for kayaks, canoes, paddle boards, and fishing gear. Opportunities like this on Dudley Pond are exceptionally rare.

108 Dudley Rd, Wayland

Listing courtesy of Listing Agent: Michael Gurtler from Listing Office: Pendleton Properties.

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