Cliff Estates, Wellesley MA: A Complete Neighborhood Guide
Considering a move to Wellesley, Massachusetts? Explore Cliff Estates, one of the most prestigious and desirable neighborhoods in town. With luxury homes, top-rated schools, spacious lots, and a walkable lifestyle, this guide outlines everything you need to know about living in Cliff Estates.
Where is Cliff Estates?
Cliff Estates is located in the western part of Wellesley, near Wellesley Hills. Known for its winding roads, mature trees, and timeless architecture, the neighborhood offers a serene residential setting just minutes from downtown.
Real Estate in Cliff Estates: Lot Sizes and Home Styles
Cliff Estates is known for its large, private lots—typically ranging from half an acre to over one acre. The neighborhood features a mix of home styles, including:
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Classic New England Colonials
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Tudor Revivals
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Georgian estates
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Custom new construction homes
Homes generally range from 4,000 to over 7,000 square feet, with thoughtful landscaping and a high standard of design and finishes.
Home Values and Market Trends
As of 2025, home prices in Cliff Estates range from approximately $2.5 million to well over $5 million, with some properties exceeding $10 million. This neighborhood consistently ranks among the highest in Wellesley for average sale price due to its location, prestige, and strong resale value.
Why prices remain high:
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Proximity to schools and commuter routes
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Estate-quality properties and architecture
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Limited inventory of high-end homes
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Long-term community investment
Schools Serving Cliff Estates
Families are drawn to Cliff Estates for its access to the highly regarded Wellesley Public Schools. Local options include:
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Elementary School – this varies based on street; contact me to confirm which school you'll be in if you buy in the neighborhood
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Wellesley Middle School – offering advanced programs and extracurriculars
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Wellesley High School – consistently ranked among the top public high schools in Massachusetts
Commuting and Transportation
Cliff Estates provides a balance of privacy and convenience for commuters.
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Driving to Boston typically takes 30–45 minutes via Route 9 or the Mass Pike (I-90)
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The Wellesley Hills commuter rail station offers direct service to South Station
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Limited MBTA bus access is available nearby for additional public transportation options
This central location appeals to professionals who want suburban living without sacrificing access to the city.
Parks, Trails, and Recreation
The neighborhood is well connected to Wellesley’s recreational resources, making it easy to enjoy the outdoors:
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Boulder Brook Reservation – ideal for walking, running, or biking
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Wellesley Country Club – offers golf, tennis, swimming, and social programming
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Wellesley Recreation Center – features playing fields, classes, and youth sports programs
In addition, residents are close to nature trails, conservation land, and playgrounds throughout town.
Walkability and Lifestyle
Cliff Estates may be suburban in design, but its walkability is a key advantage. Many homes are within walking distance of:
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Downtown Wellesley shops and cafés
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Bates School and sports fields
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Wellesley Hills train station
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Boulder Brook reservation area; The Brook Path and Fuller Brook Park
This blend of residential privacy and community connection is one of the neighborhood’s greatest strengths.
Why Choose Cliff Estates?
Cliff Estates offers a unique combination of luxury living and small-town charm. It is ideal for buyers looking for:
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Spacious, high-end homes
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Excellent public schools
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A quiet, established neighborhood
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Access to Boston for work or entertainment
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A strong sense of community
