Vintage homes for sale & real estate in Wayland, MA

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OPEN SAT, 11AM TO 12:30PMFLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Wayland, MA:
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 comfortab

$1,225,000

3 beds3 baths2,585 sq ft

44 Pequot Rd, Wayland, MA 01778

Separate office • Walk-out lower level • Expansive backyard

OPEN TODAY, 3:30PM TO 5PM3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Wayland, MA:
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 c

$1,196,000

4 beds2 baths2,400 sq ft

89 Dudley Rd, Wayland, MA 01778

Private dock • Double lot • Waterfront living

OPEN SAT, 11AM TO 1PM

ABOUT THIS HOME
Vintage Home for sale in Wayland, MA:
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 w

$1,365,000

5 beds3 baths2,815 sq ft

26 Millbrook Rd, Wayland, MA 01778

Formal dining room • Grand foyer • Updated kitchen

ABOUT THIS HOME
Vintage Home for sale in Wayland, MA:
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. Co

$920,000

4 beds2 baths1,497 sq ft

38 Hawthorne Rd, Wayland, MA 01778

Fresh coat of paint • New carpet • Central air

ABOUT THIS HOME
Vintage Home for sale in Wayland, MA:
Welcome to this cozy single-family ranch in a peaceful Wayland neighborhood! This home offers 2 bedrooms, 1 full bathroom, hardwood flooring, and a bright, inviting interior. The kitchen features granite countertops and ample cabinet space. Enjoy the heated sunroom, perfect for relaxing or dining while overlooking the greenery, with direct access to the outdoor patio. Additional features include a full basement offering extra storage, a paved driveway, and a convenient location near local schools, major highways, and the Sudbury River. Located in the desirable Wayland community, this home offers an excellent opportunity for buyers looking for a comfortable home in a convenient suburban sett

$585,000

2 beds1 bath1,050 sq ft

26 Riverview Cir, Wayland, MA 01778

Heated sunroom • Paved driveway • Full basement

Property at 3 Tally Ho Ln, Wayland, MA 01778, 3 beds, 3 baths

$1,275,000

3 beds3 baths2,131 sq ft

3 Tally Ho Ln, Wayland, MA 01778

Property at 186 Main St, Wayland, MA 01778, 8 beds, 3 baths

$1,475,000

8 beds3 baths3,400 sq ft

186 Main St, Wayland, MA 01778

Property at 249 Main St, Wayland, MA 01778, 2 beds, 1 bath

$499,000

2 beds1 bath840 sq ft

249 Main St, Wayland, MA 01778

Property at 202 Boston Post Rd, Wayland, MA 01778, 6 beds, 3.5 baths

$1,399,900

6 beds3.5 baths3,672 sq ft

202 Boston Post Rd, Wayland, MA 01778

Property at 5 Mansion Rd, Wayland, MA 01778, 2 beds, 2 baths

$679,900

2 beds2 baths1,500 sq ft

5 Mansion Rd, Wayland, MA 01778

Property at 30 Snake Brk, Wayland, MA 01778, 4 beds, 2.5 baths

$1,675,000

4 beds2.5 baths2,656 sq ft

30 Snake Brk, Wayland, MA 01778

Property at 81 Riverview Cir, Wayland, MA 01778, 3 beds, 2 baths

$699,000

3 beds2 baths2,058 sq ft

81 Riverview Cir, Wayland, MA 01778

Property at 55 Glezen Ln, Wayland, MA 01778, 6 beds, 5.5 baths

$2,195,000

6 beds5.5 baths5,818 sq ft

55 Glezen Ln, Wayland, MA 01778

Property at 18 Lodge Rd, Wayland, MA 01778, 2 beds, 1.5 baths

$734,000

2 beds1.5 baths1,286 sq ft

18 Lodge Rd, Wayland, MA 01778

Property at 8 Damon, Wayland, MA 01778, 5 beds, 2 baths

$1,195,000

5 beds2 baths3,100 sq ft

8 Damon, Wayland, MA 01778

Property at 136 Commonwealth Rd, Wayland, MA 01778, 5 beds, 2 baths

$1,099,999

5 beds2 baths3,300 sq ft

136 Commonwealth Rd, Wayland, MA 01778

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OPEN SAT, 12PM TO 1PM

ABOUT THIS HOME
Vintage Home for sale in Wayland, MA:
Welcome to 16 Overbrook Terrace! Tucked away on a quiet street near the Natick/Wellesley line, this beautifully maintained single-family home offers an ideal blend of style, comfort, and convenience. Extensively renovated in 2017, the home features an inviting open floor plan with vaulted, beamed ceilings, a wood-burning fireplace, and a beautifully updated kitchen with granite countertops and stainless steel appliances. Two bedrooms, an updated full bath, and a versatile mudroom with laundry complete the main level. A separate office/bonus room provides flexible space for working from home. Improvements include updated electrical, plumbing, windows, heating and cooling systems, and a Navie

$710,000

2 beds1 bath1,371 sq ft

16 Overbrook Ter, Natick, MA 01760

Open floor plan • Updated full bath • Updated kitchen

ABOUT THIS HOME
Vintage Home for sale in Wayland, MA:
Bring your vision and build instant sweat equity in this bright, sun-splashed home with tremendous potential. Updated roof, top-of-the-line Buderus heating system, oil tank, windows, appliances, and carpeting, plus blown-in insulation. A new dishwasher and dryer add further value. Move in now and make it your own at your pace. Located in the sought-after Weathersfield neighborhood, where many homes have been renovated, expanded, or rebuilt, this solid home is fully functional, with all major systems operating properly. Perfect for young families seeking a superb community with excellent schools, or downsizers looking for comfortable one-floor living. It offers a spacious living room with la

$729,900

3 beds1 bath1,378 sq ft

6 Wentworth Rd, Natick, MA 01760

Formal dining room • Charming sun porch • Level backyard

VIDEO TOUR

ABOUT THIS HOME
Vintage Home for sale in Wayland, MA:
14 Stratford Rd in Natick, Massachusetts, presents an exceptional opportunity to acquire a well-maintained single-family residence. This 2,016-square-foot home is in great condition, offering an excellent location with proximity to Schools, shopping, dining and commuter options. Beyond the ample primary living areas, the property offers versatile utility through its basement, providing ample space for storage or future expansion. Outside, the residence is complemented by a private yard, offering a dedicated outdoor area for recreation and personal enjoyment set upon the 10,724-square-foot lot. The home encompasses four bedrooms and two full bathrooms, providing a balanced layout well-suite

$899,000

4 beds2 baths2,016 sq ft

14 Stratford Rd, Natick, MA 01760

Private yard • Well maintained • Excellent location

OPEN SAT, 11:30AM TO 1PM3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Wayland, MA:
Lovingly maintained, this adorable Cape-style home is filled with character, charm, and warmth. Tucked at the end of a peaceful cul-de-sac, the light-filled living room welcomes you with a cozy fireplace and beautifully refinished hardwood floors. The inviting eat-in kitchen flows effortlessly into the comfortable family room, creating a wonderful gathering space with easy access to the backyard. Two bedrooms with gleaming hardwood floors and a full bath complete the first floor. Upstairs, two additional bedrooms offer cozy retreats with brand-new carpeting and newly added electric baseboard heat. Freshly painted throughout, the home feels bright, fresh, and welcoming. Outside, the backyard

$659,900

4 beds1 bath1,300 sq ft

25 Orchard Rd, Natick, MA 01760

Cape-style home • Eat-in kitchen • Cozy fireplace

OPEN SUN, 11:30AM TO 12:30PM

ABOUT THIS HOME
Vintage Home for sale in Wayland, MA:
Privately set on 2.7 acre, this distinguished 16-room landmark residence embodies the timeless elegance and gracious scale of a classic New England estate, thoughtfully enhanced for modern living. A stately entry welcomes you to beautifully preserved architectural details, including dramatic ceilings and windows, exquisite millwork and hardwood floors throughout. Designed equally for grand entertaining and intimate gatherings, the formal living room is anchored by a handsome fireplace, while the richly appointed library, with its own fireplace and built-in bookcases, offers a warm and inviting retreat. A comfortable family room provides a relaxed setting for everyday living. At the heart of

$3,495,000

6 beds6 baths6,485 sq ft

863 Boston Post Rd, Weston, MA 02493

Formal dining room • Butler's pantry • 2.7 acre

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Wayland, MA:
PRICE ADJUSTMENT - $ 644,000! Motivated Seller! NEW SEPTIC SYSTEM WITH AT LEAST 2-BEDROOM DESIGN CAPACITY TO BE INSTALLED AND FULLY APPROVED BY SELLER! Welcome to 38 Loker Street, ideally set in one of Natick's most convenient and sought-after neighborhoods. This charming 1925-built home offers 1,362 square feet of living space with 1 bedroom, a versatile loft, and 2 bathrooms, blending timeless character with thoughtful updates throughout. Original architectural details give the home warmth and personality, while more recent mechanicals — including 2 mini-splits and an updated hot water tank — offer everyday comfort and peace of mind. The loft adds flexible space, perfect for a

$644,000

1 bed2 baths1,362 sq ft

38 Loker St, Natick, MA 01760

Flexible space • Recent mechanicals • Easy access to shops

Property at 270 Concord Rd, Lincoln, MA 01773, 4 beds, 3 baths

$2,790,000

4 beds3 baths5,040 sq ft

270 Concord Rd, Lincoln, MA 01773

Property at 214 Boston Post Rd, Sudbury, MA 01776, 2 beds, 1 bath

$395,000

2 beds1 bath1,500 sq ft

214 Boston Post Rd, Sudbury, MA 01776

Property at 203 Bacon St, Natick, MA 01760, 4 beds, 1.5 baths

$1,029,000

4 beds1.5 baths1,872 sq ft

203 Bacon St, Natick, MA 01760

Property at 13 Milford Ave, Natick, MA 01760, 5 beds, 2 baths

$1,149,000

5 beds2 baths2,628 sq ft

13 Milford Ave, Natick, MA 01760

Property at 12 New Hampshire Ave, Natick, MA 01760, 4 beds, 1 bath

$650,000

4 beds1 bath1,340 sq ft

12 New Hampshire Ave, Natick, MA 01760

Property at 28 Bogle, Weston, MA 02493, 3 beds, 4.5 baths

$2,850,000

3 beds4.5 baths4,780 sq ft

28 Bogle, Weston, MA 02493

Property at 27 Randy Rd, Framingham, MA 01701, 4 beds, 2 baths

$749,000

4 beds2 baths2,168 sq ft

27 Randy Rd, Framingham, MA 01701

Property at 5 Pryor Rd, Natick, MA 01760, 3 beds, 2.5 baths

$1,119,000

3 beds2.5 baths2,389 sq ft

5 Pryor Rd, Natick, MA 01760

Property at 346 Old Connecticut Path, Framingham, MA 01701, 3 beds, 2 baths

$585,000

3 beds2 baths1,312 sq ft

346 Old Connecticut Path, Framingham, MA 01701

Property at 30R Morses Pond Rd, Wellesley, MA 02482, 3 beds, 2 baths

$1,300,000

3 beds2 baths1,640 sq ft

30R Morses Pond Rd, Wellesley, MA 02482

Property at 58 Upland Rd, Natick, MA 01760, 4 beds, 2.5 baths

$875,000

4 beds2.5 baths2,050 sq ft

58 Upland Rd, Natick, MA 01760

Property at 8-10 Concord Rd. & 356 Boston Post, Sudbury, MA 01776, 5 beds, 4 baths

$2,599,000

5 beds4 baths5,588 sq ft

8-10 Concord Rd. & 356 Boston Post, Sudbury, MA 01776

Vintage Homes for Sale in Wayland

There are currently 16 vintage homes for sale in Wayland at a median listing price of $1.1M. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Wayland stay on the market for 33 days and receive 1 offers. Popular neighborhoods include North Framingham, Wellesley Fells, Nobscot, Saxonville, and Musketamquid Village. This map is refreshed with the newest listings in Wayland every 15 minutes.

In the past month, 12 homes have been sold in Wayland. In addition to houses in Wayland, there was also 1 condo, 9 townhouses, and 2 multi-family units for sale in Wayland last month. Find your dream home in Wayland using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Wayland are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Wayland. Our Wayland real estate stats and trends will give you more information about home buying and selling trends in Wayland. If you're looking to sell your home in the Wayland area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Wayland with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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