Doug McNeilly
Coldwell Banker Realty

Wayland Neighborhoods

Wayland is less driven by large developments than some other suburban towns.  While some neighborhoods were developed in certain decades there are many sections of Wayland that have no label.  More often, sections of former Farm Land was sold off and developed creating new streets.  Many neighborhoods abut conservation land with walking / hiking trails.  Overall, styles and price points vary, but often coexist comfortably next to each other. 


Charena Farms
Named after the farm at the time the neighborhood was developed.  Just north of the High School.  Enclosed neighborhood that borders the Sudbury River includes Clarence Road, Cameron Road, and Kelsey Road.  Mainly Colonials and Multi-Level homes with some Ranches and Contemporaries.  Prices range from $500s up to $800s.

Claypit or Claypit Hill
Claypit Hill is often considered the premier Wayland neighborhood.  The lots are general larger and houses are set back on tree-lined roads.  Claypit Hill is located north of Route 20 and south of Glezen and Moore Roads.  Many of the homes are larger in scale.  The homes near Moore Road and Orchard Lane are typically more modest.  You often hear the term “Swiedler” which references a builder of 400+ homes in Wayland and Weston in the 1950s and 1960s.  These were larger scale Capes and Colonials for the time and are sought after today.  The Wayland Swim and Tennis Club is located here.  The modest homes are in the $600s to $800s.  Most larger homes are $1.25M plus.  Expansive homes top $2M+.

Cochituate Village
The area dates back to 1720s.  The name came about after Long Pond was renamed Lake Chocituate in 1848.  It is the area between Commonwealth Avenue (Route 30) and East Plain / West Plain Street along Main Street (Route 27) and the side street off of Main Street.  It is home to several businesses and restaurants and the Town Ball Field.  The size and style of the homes is mixed with a few larger homes that were residences of the factory managers at the turn of the 1900 century.  Prices vary considerably.

Covered Bridge
Newer development of 14 high-end Colonials off of Rice Road built in 2014.  True to its name, there is a Covered Bridge to cross to access the neighborhood.  It is a "cluster" or "open space" development, where house lots are smaller and positioned in a way to maximize open space and preserve nature and wildlife habitat.  There have been no resales to date.  Original sale prices were between $1.3M and $2.2M

Daymon Farms
Located on the south side of Wayland.  This 1950s neighborhood of approximately 125+ homes is mainly a mixture of ranch, multi-level, and colonial style homes.  Named after the Damon Family (with no “y”) that owned several farms in the area during Colonial times.  Many homes have been updated and expanded over the years.  There are two entrances to the neighborhood that provide a closed off feeling – neighbors walk the streets and children ride bikes.  On the south side the neighborhood is bordered by the Mass Pike.  Sales prices in 2019 ranged from the $400s for smaller ranches needing updates to over $1M for an expanded updated colonial. 

Dudley Pond
Dudley Pond is a well-known Wayland treasure.  Being over 10 acres, it is considered a “great pond.”  From 1847 to about 1900 it was a standby water source for Boston.  Initially most of the homes were Summer cottages.  Over time, homes have been renovated or razed and rebuilt. The area is bound by Main Street (Route 27), West Plain Street, Old Connecticut Path (Route 126) and the Hultman Aqueduct (a popular walking trail).  The Dudley Chateau a speakeasy during Probation is a great for a Burger and to catch the game.  Home prices range from $200s (small one bedroom cottages off water) to over $1M for larger waterfront homes.

Greenways (The Homes at Traditions)
This is a cluster development abutting the Greenways Conservation Land.  Lots are smaller than normal and the homes are close together, but that is by design and the benefits of having abutting conservation land.  Neighborhood feel.  Great access to walking and hiking.  The development was built in 2000.  The homes are colonial with 4 Bedrooms and 2.5+ Baths.  Most are 3,000 to 4,500 SQFT.  There have not been many resales but prices would be in the $900K to $1.1M range.

Happy Hollow
Reportedly named for the abundance of Taverns in the area in the 1700s.  The curves in Rice Spring Lane were to preserve tress important to the owner that sold the land to the initial Developer.  The homes – Capes, Ranches, and Colonials – were mostly built in the 1950s and 1960s and lots were sold off and built mainly one by one.  Many homes have been expanded.  It is a popular neighborhood since it is in walking distance of all three schools – Elementary, Middle, and High School.  Sales in 2019, ranged from the $600s to just over $1M.  I call Happy Hollow home!

Lake Cochituate
This is small neighborhood between Lake Cochituate and West Plain Street and is home to the Wayland Town Beach.  Development occurred mainly after Lake Cochituate (meaning head of running water) ceased being a water supply for Boston.  A few smaller cottages remain along the Lake, but most are larger homes now.  Homes away from the lake were mainly built in the 1950s and 1960s. Homes ranges in price from the $600s or over $1M for homes with lake frontage and docks.

Oak Hill
Enclosed neighborhood built in the late 1960s.  Mainly 4-bedroom Colonial, Split Level, and Raised Ranch style homes.  Since there is only one entrance to the neighborhood, there is little thru traffic.  Convenient south Wayland location near shopping, schools, and commuting routes.  Price are generally in the $600s (lower than typical for Wayland for the size) because of the proximity to Power Lines and the Wayland Rod & Gun Club.  Updated homes can go over $700k.

North Wayland
Often considered anything north of Route 20, here we are considering the area north of Claypit Hill as North Wayland.  The price and feel vary from street to street.  There are more modest homes along Gray Birch Lane and Red Barn Road ($500s to $600+).  Off of Oxbow Road:  York Road has younger colonials in the $1M+ range.  Williams Road has 1990s Colonials in the $1M+ range.  Grove Street is mainly 1960s and 1970s Colonials in the $800K+ range.  Hampshire Road is mixed with 1960s Colonials and Contemporaries $850K+ in value.  Campbell Road also has 1960s Colonials and Contemporaries $850K to $1M+ range.  Homes along Sherman’s Bridge Road vary in style – Capes, Colonials and Ranches are more modest in size and generally under $700K.  The homes along Lincoln Road vary in style but are similar in that they are mostly expansive on large private lots and are over $1M+.  As you can see….North Wayland prices and styles of homes are very diverse.

Rich Valley
Enclosed neighborhood off of Boston Post Road (Route 20).  Made up of Rich Valley Road, Hayward Road, Lundy Lane, Sylvan Way, and White Road.  Built mainly in the 1940s through 1960s the neighborhood contains mainly Ranch and Cape style homes with some Colonials.  Homes range in value from the $500s to near $1M for expanded, updated homes.

Riverview
Located off of Stonebridge Road, Riverview has an eclectic mix of housing.  It varies from cottage style homes – the neighborhood was originally comprised of Summer Cottages along the Sudbury River – to newer Colonial style homes.  The partial remains of Stone Bridge is in the neighborhood.  Price vary greatly from the $400s to over $800K.

Tower Hill
Not really a neighborhood although it is an area listed in the Multiple Listing Service (MLS).  It is located in the Claypit Hill and is actual an old Train Station (long gone) located on Plain Road at the Central Massachusetts Rail Trail.

Town Center
The area is along Boston Post Road (Route 20) and the around the intersections Cochituate Road / Old Sudbury Road (Route 27) and Concord Road (Route 126).  This area has many of Wayland Historic Homes – many dating back to the 1700s.  The Library, Town Buildings and the New Wayland Town Center with its two Condominium Complexes are in the Town Center area.  There are a few sides streets – Bow Road and Winthrop Road both which have older Historic homes.  Price vary based on size, condition, proximity to the road from $700s to $1.25M+

Wayland Hills
Located on the south side of Wayland near the Weston town line, Wayland Hills offers a great commuting location into Boston.   While the homes are mainly Capes, Raised Ranches, Split Levels, and Multi-Levels that were built as large format examples at the time they were constructed.  Many have been expanded and updated.  Price are generally $800K to $1.2M+

Weston Estates
Built as an upscale neighborhood in the 1970s it is accessed through Weston, but is in Wayland.  The neighborhood has large expansive lots with homes set back from the road.  Homes are generally 3,500+ SQFT and values are $1.5M+

Woodridge
Woodridge Road meanders through the neighborhood – and includes road off of Woodridge such as Country Corners and Barney Hill.  The neighborhood has numerous contemporary 1950s and 1960s homes as well as the standard assortment of Capes and Colonials.  Both Deer Run and High Rock offer great views from higher vantage points and also higher prices.  Prices in the neighborhood vary based on the street and size of the home from the $600s to well over $1M.