10

Wellesley Hills Homes for Sale

Section Image
  • 14 Bird Hill Ave, Wellesley Hills, MA 02481
    14 Bird Hill Ave, Wellesley Hills, MA 02481
    14 Bird Hill Ave, Wellesley Hills, MA 02481
    /37

    $3,895,000

    • 5 Beds
    • 5.5 Baths
    • 5,833 Sq Ft

    14 Bird Hill Ave, Wellesley Hills, MA 02481

    One of 3 exceptional new construction homes by one of Wellesley’s premier builders -Copper Leaf Development. Sited on an ended way in Wellesley Farms, this 5800 square foot 5 bedroom 5/1 bath home has been thoughtfully designed with rich finishes, superb building materials, 9’ ceilings on the first and second floors and a floor plan which works for everyday life and formal entertaining. Grand

    Donahue Maley & Burns Team Compass

    14 Bird Hill Ave, Wellesley Hills, MA 02481
  • 12 Bird Hill Ave, Wellesley, MA 02481
    12 Bird Hill Ave, Wellesley, MA 02481
    12 Bird Hill Ave, Wellesley, MA 02481
    /37

    $3,895,000 Open Sun 12PM - 1:30PM

    • 5 Beds
    • 5.5 Baths
    • 5,833 Sq Ft

    12 Bird Hill Ave, Wellesley, MA 02481

    One of 3 exceptional new construction homes by one of Wellesley’s premier builders -Copper Leaf Development. Sited on an ended way in Wellesley Farms, this 5800 square foot 5 bedroom 5/1 bath home has been thoughtfully designed with rich finishes, superb building materials, 9’ ceilings on the first and second floors and a floor plan which works for everyday life and formal entertaining. Grand

    Donahue Maley & Burns Team Compass

    12 Bird Hill Ave, Wellesley, MA 02481
  • 20 Oakland St, Wellesley, MA 02481
    20 Oakland St, Wellesley, MA 02481
    20 Oakland St, Wellesley, MA 02481
    /40

    $3,690,000

    • 6 Beds
    • 7.5 Baths
    • 6,499 Sq Ft

    20 Oakland St, Wellesley, MA 02481

    **ENTRANCE @ 367 WORCESTER STREET** This stunning 6,500 sq ft colonial blends timeless design & modern luxury. Set back from Worcester Street, the home features a dramatic 2-story foyer, white oak floors, soaring ceilings & sunlit open living/dining spaces. Chef’s kitchen w/ Thermador appliances, quartz counters, waterfall island & stylish pendant lighting. Two rear decks connected by a stone

    Michael Tinsley Longwood Residential, LLC

    20 Oakland St, Wellesley, MA 02481
  • 22 Priscilla Cir, Wellesley Hills, MA 02481
    22 Priscilla Cir, Wellesley Hills, MA 02481
    22 Priscilla Cir, Wellesley Hills, MA 02481
    /38

    $3,695,000 Open Sun 12PM - 1:30PM

    • 6 Beds
    • 5.5 Baths
    • 5,900 Sq Ft

    22 Priscilla Cir, Wellesley Hills, MA 02481

    Amazing opportunity in Wellesley with this brand new construction by a highly esteemed local builder. Featuring an exquisite design and high-end finishes, this home offers a flexible floor plan to accommodate diverse lifestyle needs. Highlights include an optional first-floor bedroom. 6 Beds, 6 baths, high end finishes, wide plank wood floors, gorgeous millwork and 9 foot ceilings on all three

    Donahue Maley & Burns Team Compass

    22 Priscilla Cir, Wellesley Hills, MA 02481
  • 365 Worcester St, Wellesley, MA 02481
    365 Worcester St, Wellesley, MA 02481
    365 Worcester St, Wellesley, MA 02481
    /26

    $3,590,000

    • 6 Beds
    • 7 Baths
    • 7,000 Sq Ft

    365 Worcester St, Wellesley, MA 02481

    New Construction 2025! This classic brick-front New England colonial offers the ultimate luxury for all lifestyles. Perched between Washington Street and Worcester Street, this south-facing home is centrally located with access to all Wellesley offers with great commuter access. Dramatic grand entrance with a stunning staircase, huge windows, and an inviting foyer. Seven en-suite bedrooms over

    Erika Welch Rettman Associates

    365 Worcester St, Wellesley, MA 02481
  • 1 Clock Tower Dr, Wellesley Hills, MA 02481
    1 Clock Tower Dr, Wellesley Hills, MA 02481
    1 Clock Tower Dr, Wellesley Hills, MA 02481
    /41

    $2,750,000

    • 5 Beds
    • 4.5 Baths
    • 5,261 Sq Ft

    1 Clock Tower Dr, Wellesley Hills, MA 02481

    Perched on a serene hilltop, this elegant colonial home boasts a stunning facade inspired by the Wellesley Clock Tower. Just minutes from the Issac Sprague Memorial Clock Tower and Elm Park, this sunlit residence features soaring ceilings and oversized windows that bathe the interiors in natural light. The gourmet kitchen, designed for the avid cook, opens to an exquisite breakfast nook with

    Dream Team Dreamega International Realty LLC

    1 Clock Tower Dr, Wellesley Hills, MA 02481
  • 6 Oakland Cir, Wellesley Hills, MA 02481
    6 Oakland Cir, Wellesley Hills, MA 02481
    6 Oakland Cir, Wellesley Hills, MA 02481
    /10

    $1,258,000 Open Sun 12PM - 2PM

    • 3 Beds
    • 2 Baths
    • 1,521 Sq Ft

    6 Oakland Cir, Wellesley Hills, MA 02481

    Welcome to this amazing single family situated on over 10,000 square foot flat landscaped lot. This charming property offers amenities and picturesque views, featuring an open concept design, the home boasts natural light and spacious living area. The kitchen featuring granite counters and stainless steel appliances. Tiled bathrooms. Fresh paint, refinished hardwood floors and new light

    Henry Lee Patriot International Realty

    6 Oakland Cir, Wellesley Hills, MA 02481
  • 6 Willow St, Wellesley, MA 02481
    6 Willow St, Wellesley, MA 02481
    6 Willow St, Wellesley, MA 02481
    /39

    $1,295,000

    • 4 Beds
    • 2.5 Baths
    • 2,165 Sq Ft

    6 Willow St, Wellesley, MA 02481

    A delightfully charming Cape style home with a versatile floor plan on a large, level yard filled with mature plantings for privacy. The first floor offers an open floor plan with great flow to two separate living areas, both with fireplaces, as well as a dining room and bedroom/office with hardwood flooring throughout. The updated kitchen boasts granite countertops, stainless appliances, an

    Frank Celeste Gibson Sotheby's International Realty

    6 Willow St, Wellesley, MA 02481
  • 7 Bemis Rd, Wellesley Hills, MA 02481
    7 Bemis Rd, Wellesley Hills, MA 02481
    7 Bemis Rd, Wellesley Hills, MA 02481
    /39

    $2,499,900 Open Sun 11AM - 12:30PM

    • 5 Beds
    • 5.5 Baths
    • 4,550 Sq Ft

    7 Bemis Rd, Wellesley Hills, MA 02481

    Built in 2018 and set on a sun-filled, level lot tucked quietly off the street, this contemporary home offers exceptional privacy with unbeatable convenience, just minutes to Wellesley Hills Station, cafes, Brook Path, and top schools. The thoughtfully designed open layout features a bright kitchen/family room with coffered ceilings, gas fireplace, and top-tier appliances. 5 bedrooms and 4.5

    Dream Team Dreamega International Realty LLC

    7 Bemis Rd, Wellesley Hills, MA 02481
  • 367 Worcester St, Wellesley Hills, MA 02481
    367 Worcester St, Wellesley Hills, MA 02481
    367 Worcester St, Wellesley Hills, MA 02481
    /31

    $1,699,000

    • 6 Beds
    • 4.5 Baths
    • 5,989 Sq Ft

    367 Worcester St, Wellesley Hills, MA 02481

    With frontage on Oakland Street, this majestic, historic beauty provides endless possibilities w/high ceilings, lovely details & natural light throughout. The 1st floor features a grand foyer, which flows into a fireplaced living room, elegant dining room & family room/library - ideal for family enjoyment & entertaining. A sweeping, covered porch, just off the living room, overlooks the expansive

    Beyond Boston Properties Group Compass

    367 Worcester St, Wellesley Hills, MA 02481
Massachusetts Norfolk County Wellesley Wellesley Hills

Real Estate & Homes for Sale in Wellesley Hills, Wellesley

Why Live in Wellesley Hills
Wellesley Hills is a neighborhood characterized by its early 20th-century architecture, featuring grand Colonial Revivals, Tudor Revivals, Cape Cods, and Garrison-style homes. Newer constructions are also present, often replacing older structures due to limited land availability. The area is known for its larger lot sizes, ranging from a quarter acre to 1 acre. Residents, including many finance, banking, and biotech executives, enjoy a community with abundant walking trails and parks such as Centennial Park and the 2.5-mile Fuller Brook Path. In winter, local hills and ponds become popular spots for ice skating and sledding. The Wellesley Country Club, with its 18-hole golf course, racquetball courts, and outdoor pool, serves as a key recreational and social hub. Commerce is centered along Washington Street, home to independent bakeries, restaurants, and shops, including the repurposed Wellesley Hills rail station now housing Caffè Nero. Whole Foods Marketplace and Linden Square offer additional retail options. Community events like Wellesley’s Wonderful Weekend and various block parties foster a strong sense of community. The neighborhood is well-connected, with the Wellesley Hill train station providing MBTA commuter rail access to Boston, and bus routes via the MetroWest Regional Transit Authority. Boston and Logan International Airport are less than 20 miles away. Students attend highly rated Wellesley Public Schools, including Joseph E. Fiske Elementary, Otho L. Schofield Elementary, Wellesley Middle School, and Wellesley High School. Local higher education institutions include Wellesley College, Babson College, and Mass Bay Community College.
Learn more about living in Wellesley Hills

Frequently Asked Questions

Is Wellesley Hills a good place to live?
Wellesley Hills is a good place to live. Wellesley Hills is considered very car-dependent and somewhat bikeable. It has a median age of 42. The average household income is $217,185 which is above the national average. College graduates make up 84.9% of residents. A majority of residents in Wellesley Hills are home owners, with 25.2% of residents renting and 74.8% of residents owning their home. A local real estate agent serving Wellesley Hills can help you decide if this neighborhood is the right one for you. Learn more on our Wellesley Hills neighborhood guide.
How much do you need to make to afford a house in Wellesley Hills?
The median home price in Wellesley Hills is $2,149,000. If you put a 20% down payment of $429,800 and had a 30-year fixed mortgage with an interest rate of 6.63%, your estimated principal and interest payment would be $11,010 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $472K a year to afford the median home price in Wellesley Hills. The average household income in Wellesley Hills is $217K.
What are the best public schools in Wellesley Hills?
The best public schools that serve Wellesley Hills are:
What are the best private schools in Wellesley Hills?
The best private schools that serve Wellesley Hills are:
  • Fessenden School has an A+ Niche grade, a student teacher ratio of 5:1 and an average review score of 4.8.
  • Wellan Montessori School has an A+ Niche grade, a student teacher ratio of 5:1 and an average review score of 4.7.
  • Dana Hall School has an A+ Niche grade, a student teacher ratio of 6:1 and an average review score of 4.3.
What are the most popular zip codes in Wellesley Hills, Wellesley, MA?
The most popular zip codes in Wellesley Hills, Wellesley, MA include 02481, 02494, 02468, 02462 and 02464.
What are the most popular neighborhoods near Wellesley Hills, Wellesley, MA?
The most popular neighborhoods near Wellesley Hills, Wellesley, MA are Waban, Wellesley Farms, Newton Lower Falls, Linden Square and Newton Upper Falls.
Are home prices dropping in Wellesley Hills?
Yes, home prices in Wellesley Hills are down 1% in the last 12 months.

Home Trends in Wellesley Hills, MA

On average, homes in Wellesley Hills, Wellesley sell after 19 days on the market compared to the national average of 52 days. The median sale price for homes in Wellesley Hills, Wellesley over the last 12 months is $2,058,000, up 5% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$2,058,000
Median Single Family Sale Price
$2,157,404
Median Townhouse Sale Price
$1,925,000
Average Price Per Sq Ft
$631
Number of Homes for Sale
10
Last 12 months Home Sales
43
Months of Supply
2.80
Median List Price
$2,149,000
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
5%
How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2025 CoStar Group