$3,069,903Average Value$662Average Price per Sq Ft9Homes For Sale
Peaceful living in Greater Boston
Since 1976, Wellesley has been a Tree City committed to developing community forestry and recreational green spaces. Less than 20 miles outside of Boston and bordered by Route 9, Cliff Estates is a sylvan residential enclave framed by century-old oak, pine and maple trees. Impressive New England homes are surrounded by conservation lands, reservoirs and reputable higher education institutes such as Wellesley College and Babson College. The town also has an A-plus public school system, and shopping districts such as Linden Square and Central Street are several blocks away. “Cliff Estates was created by Albion Clapp,” says Prudence Hay, a local Realtor at Rutledge Properties. “It’s a very desirable part of town, and the homes are well laid out with 20,000 square foot lots.”
The wide streets of Cliff Estates are lined with beautiful Colonials.
Beautiful homes in Cliff Estates are a few short miles from the Boston metro area.
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A peaceful community with stately mansions
The wooded community features stately 20th-century Colonial Revivals, Garrison styles, Cape Cods and recently built contemporary homes with open floor plans. Single-family residences here typically start at $1 million and go up to $3 million. Many estate properties around 5,000 square feet can fall between $3 million and $6 million. Houses here also have spacious yards, and lot sizes are usually around half an acre, with ample room for picturesque, landscaped lawns and garden designs, backyard grills and outdoor pools. Slightly curved residential roads are connected by tree-lined sidewalks, and neighbors can be spotted taking evening walks with their pets. “Although the town maintains the historic character of the homes, it also maintains a nice feel and balance of old and new,” Hay says. “If someone wants to build a new home, people are not restricted as long as they adhere to the building codes.”
Beautiful new Contemporary homes are increasingly common in Cliff Estates.
Grand Colonial Revivals are common in Cliff Estates.
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An A-plus public schools system in Wellesley
The community is zoned for Wellesley Public Schools, which has an A-plus Niche grade and is rated the No. 2 best public school district in Norfolk County. Prospective primary schools include John D. Hardy Elementary School and Isaac Sprague Elementary School, which rate an A-plus and an A, respectively. Students may then go on to Wellesley Middle School and finish secondary education at Wellesley High School, both of which have A-plus scores. Wellesley High is considered a green school, featuring solar thermal cooling and geothermal heat pumps. Additionally, the high school partners with Mass Bay Community College and offers dual-enrollment classes, and students can also take courses at neighboring Wellesley College, a leading liberal arts institute that’s right in town. Babson College, a highly reputable business school, is 2 miles east.
Wellesley Sr High School receives an overall grade of A+ from Niche.
Wellesley Middle School serves students in grades 6-8 and receives an overall grade of A+.
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Social events at Wellesley Country Club
The town has over 26 miles of trails that connect its conservation and green spaces, making it easy for residents to walk and enjoy the outdoors. Popular spots around the neighborhood include Carisbrooke, Colburn Road and Boulder Brook Reservation and Peirce Hill Reservoir. People also walk to Morton Park to see ducks in the pond and have picnics on the expansive green lawn. Those who walk their dogs often head to Kelly Memorial Park. Rockridge Pond is the local fishing place, and people also skate here on the pond in winter. Less than 3 miles south, Wellesley Country Club features a championship private course, a pool, tennis and pickleball facilities and children's programs, serving as a significant social venue for residents of Wellesley.
Cliff Estates residents can enjoy a beautiful view from Boulder Brook Reservation.
Wellesley Country Club's golf course is easily accessible to Cliff Estates residents.
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Shopping and dining at Linden Square and Central Street
Across from Route 9, Linden Square is the town’s main shopping district, featuring Roche Bros, clothing stores, local businesses and restaurants such as The Cottage Wellesley, which serves casual American fare with fresh ingredients. Whole Foods Market is several blocks away, and The Local Kitchen & Drinks, a trendy New American restaurant, is farther north along Washington Street. Target is about 7 miles west in Framingham.
Cliff Estates residents enjoy shopping the lovely produce at Whole Foods Market.
Stop into The Local near Cliff Estates for a cold drink and a fine meal.
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Navigating into Boston
The town is accessible via Interstate 95, Massachusetts Route 9, the MetroWest Regional Transit Authority bus service and the MBTA commuter rail. Wellesley has three rail stations for the Framingham/Worcester Line, which runs from Boston to Framingham. The closest station to Cliff Estates is Wellesley Hills. Boston and Logan International Airport are both approximately 15 miles east, and Newton-Wellesley Hospital is less than 4 miles away. The community is car-dependent, and is bordered by Route 9 on the south side.
Town events in Wellesley
Wellesley has many community celebrations throughout the year, including a spring festival, the July Jubilation Sidewalk Sale & Festival at Wellesley Square, and a fall harvest festival sponsored by Temple Beth Elohim featuring an artisan market, live bluegrass music, a donut food truck and wood fire pizzas. In addition, the town also has an annual Festival of Trees ceremony in the winter holidays, and Wellesley’s Wonderful Weekend is known for its Veterans parade, fireworks and a town-wide picnic.
GreatSchools:
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Cliff Estates Demographics and Home Trends
On average, homes in Cliff Estates, Wellesley sell after 20 days on the market compared to the national average of 53 days. The median sale price for homes in Cliff Estates, Wellesley over the last 12 months is $2,517,500, down 8% from the median home sale price over the previous 12 months.
A rare blend of timeless elegance and modern luxury in prime Wellesley Hills. This sun-drenched estate on 1⁄2 acre offers soaring ceilings, a stunning open floor plan, and high-end finishes throughout. The gourmet kitchen, luxurious owner’s suite with private roof deck, and versatile lower level with gym and guest suite create the perfect balance of comfort and style. The beautifully landscaped
Catherine BassickDouglas Elliman Real Estate - Park Plaza
Fantastic New Construction, thoughtfully designed & beautifully appointed, this home offers modern luxury w/timeless elegance. A gracious, sun-filled two-story foyer opens to a formal living room w/fireplace & banquet-size dining room complete w/butler's pantry. The sleek chef's kitchen features high-end appliances, a quartz waterfall island, walk-in pantry, sunny breakfast nook, & stylish wet
Set on a tree-lined block in the coveted Cliff Estates enclave, this to-the-studs 2025 renovation and expansion of a classic New England Colonial is a singular achievement of brilliant design, timeless elegance, and refreshing livability. The expansive living spaces are distinguished by beautifully curated fixtures and finishes, from the fluted marble fireplace to bespoke lighting and hardware.
In a desirable Boston Metrowest neighborhood, walking distance to parks, restaurants and shopping, 5 minute walk to MBTA commuter rail into Boston. Abundant sunny and quiet shared spaces in a 4BR/2 BA home with patio and yard. Renting to visiting scholars, graduate students and professionals who seek a private, comfortable, conveniently located rental in Metrowest Boston, close to many amenities.
Located in Wellesley's prestigious Cliff Estates, this property offers timeless charm and spacious living in a well maintained Colonial home. With 5 bedrooms and 3.5 bathrooms, this classic residence features hardwood floors throughout, a sun-filled formal living room with fireplace, and a floorplan offering separate dining and family rooms ideal for both entertaining and everyday living. The
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