Browse All Wayland MA Properties with Pool for Sale

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.

$1,149,000

3 Beds ⋅ 3 Baths ⋅ 73582737 MLS

Set on nearly an acre in prime location, North Wayland, 32 Moore Road offers a standout combination of flexible interior space and exceptional outdoor living. Conveniently located with easy access to Route 128/I-95, I-495, the Mass Pike, and Boston, the property offers a strong balance of suburban privacy and Greater Boston accessibility. The fully fenced backyard is the centerpiece, featuring a heated inground saltwater pool, gazebo, patio, functional greenhouse, Reeds Ferry shed, and spectacular established gardens with extensive hydrangea plantings. Inside, the 3-bedroom home offers approximately 1,913 square feet of living space with a bright, functional layout and multiple gathering areas. The updated kitchen features white cabinetry and stainless-steel appliances, generous quartz counter space, and an open connection to the dining area. A large living room with a wood-burning fireplace provides a comfortable main gathering space, while the light-filled sunroom with a Vermont Castings woodstove function as a secondary living area overlooking the backyard and pool. The main bedroom suite includes a private bath and dual closets, while an additional second-floor bath includes convenient laundry. The finished lower level adds flexible space for a home office, game room, media area, or additional entertainment space, along with a second fireplace and an additional laundry setup. A two-car garage with workshop space adds useful storage and functionality. With a heated pool, expansive gardens, greenhouse, multiple living areas, and adaptable lower-level space, 32 Moore Road offers a distinctive Wayland setting designed for both everyday living and entertaining.

32 Moore Road, Wayland

Listing courtesy of Listing Agent: Madison Nash from Listing Office: Signature Properties, Inc..

$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.

$3,950,000

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.

$1,950,000

4 Beds ⋅ 3 Baths ⋅ 73534765 MLS

A rare opportunity to own one of Wayland's most significant historic estates. The Warren Gould Roby House, circa 1880, is a distinguished Colonial Revival residence set on 4.5 extraordinary acres in the heart of town.Rich in architectural character and timeless elegance, this stately home has been thoughtfully preserved while offering the comfort and livability desired today. Grand rooms, soaring ceilings, and remarkable craftsmanship create a sense of scale and sophistication rarely found.Beyond the home, the property unfolds into a private oasis featuring expansive lawns, mature gardens, a swimming pool, and picturesque outdoor spaces designed for gathering and celebration. The impressive two-story barn offers endless possibilities—whether for entertaining, a collector's showcase, creative pursuits, or special events.More than a residence, it is a legacy property—a chance to become the next steward of a home that has shaped Wayland's landscape for generations.

11 Concord Road, Wayland

Listing courtesy of Listing Agent: Nikki Milott McCay from Listing Office: Gibson Sotheby's International Realty.

$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.

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Wayland Homes with Pool

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Browse All Wayland MA Properties with Pool for Sale

Wayland Homes with Pool

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