21 Pine Plain Rd, Wellesley, MA 02481
Family Room with Built-in Bookshelves (Furniture, TV not included)
Bedroom (furniture not included)
OFF MARKET

21 Pine Plain Rd
Wellesley, MA 02481

  • 4 Beds
  • 2.5 Baths
  • 2,340 sqft

$1,770,800

Trulia Estimate
as of Aug 9, 2026
Est. Refi. Payment $10,646/mo*
Refinance Your Home

$1,770,800

Trulia Estimate
as of Aug 9, 2026
Est. Refi. Payment $10,646/mo*
Refinance Your Home
4 Beds
2.5 Baths
2,340 sqft

Local Information

  • Map ViewExplore the area around 21 Pine Plain Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Living Area
2,340 sqft
Price/Sqft
$757
Parking
Attached Garage

About this House

This classic New England colonial home, with 4 bedrooms and 2.5 baths, is perfect for a family. On a quiet dead-end street, it has a deep, fully-fenced yard, large family room, remodeled kitchen, and two-car heated, attached garage. Well-behaved pets are welcome. Pictures show furniture, but this house is for rent unfurnished.

Built in the 1930s then significantly expanded, this house has both historic charm and contemporary function. The rocking-chair front porch and hardwood floors throughout the house speak to its past, while the spacious rooms and open kitchen plan welcome modern casual entertaining.

The front of the house features a cozy fireplace living room, and the back has a large, light-filled family room with custom built-in bookshelves and cabinets. The kitchen/dining room (remodeled 2015) features a large granite center island with seating, huge double sink and updated appliances.
On the second floor there are three bedrooms and a full bath, plus a primary bedroom suite with spacious bedroom and attached bath -- newly updated in 2023. The primary bedroom is fitted with two walk-in closets.
Large hall closets downstairs and upstairs provide ample storage.

The fenced backyard is extra-deep and wooded, providing privacy and lots of room to play and relax.

The basement is unfinished and dry, with a workshop on one side and laundry and storage on the other. Washer and Dryer are included with the house.

Heat is natural gas, baseboard. Much of the house has air conditioning, but three rooms need window units (provided).

A short walk down a safe dead-end street brings you to highly-rated Bates Elementary School, town soccer and baseball fields, a town tennis court, and a 64-acre nature reservation with beautiful meadow walks, a creek, and forested hills.

Less than a mile away is "Fells Corner," with a small market, pharmacy, cafe, and library branch. The town of Wellesley is about 2 miles away, with shopping, dining, an excellent library, post office, train station, and a beautiful park surrounding town hall. Wellesley Middle School and Wellesley High School, both excellent schools, are about 2 miles away.

Wellesley College, Babson College, Olin College, and Regis College, Weston Town Center and Needham Town Center are within 4 miles. Downtown Boston and Logan Airport are about a 30-minute drive if traffic is light. The MBTA commuter line train to Fenway Park, Back Bay, and South Station (downtown/financial district) is a convenient 30-minute ride.

Pets allowed, Tenant pays for electricity, heat (natural gas), garbage collection, yard maintenance and snow removal.

Landlord pays for sewer / water. We can provide a town RDF sticker for free access to town dump.

Renters insurance required.

1 year lease with first and last month rent and security deposit required on lease signing.
21 Pine Plain Rd, Wellesley, MA 02481 is a 4 bedroom, 3 bathroom, 2,340 sqft single-family home. It last sold for $715,000 on Jun 28, 2006 (10,900% above the $6,500 asking price). More recently, it was listed as a rental in June 2024 with an asking price of $6,500 per month. That rental listing was removed on September 13, 2024. It is currently off market. The Trulia Estimate is $1,770,800, with a rent estimate of $6,590/month.

Home Details for 21 Pine Plain Rd

Interior Features

Heating & Cooling
Heating: BaseboardAir ConditioningCooling System: Wall Unit, Window UnitHeating Fuel: Baseboard
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Levels, Entrance, & Accessibility
Floors: Hardwood

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: 1 YearAvailable: now

Exterior Features

Parking & Garage
Parking: Attached Off Street, On Site

Price History for 21 Pine Plain Rd

DatePriceEventSource
09/13/2024$6,500ListingRemovedZillow Rentals
06/02/2024$6,500Listed For RentZillow Rentals
06/28/2006$715,000Sold
N/A

Market trends in Wellesley

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.99M
$300KMoM
Sale-to-List Price
100.1%
1.4%MoM
Price per sq ft
$649
$56MoM
Available listings
112
1MoM
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Property Tax and Assessment

Year2025
Tax$14,269
Assessment$1,388,000
Home facts updated by county records

Comparable Sales for 21 Pine Plain Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
30 Pine Plain Rd, Wellesley, MA
0.05
Single-Family Home
$1,450,000
06/15/26
3
2
2,149
56 Pine Plain Rd, Wellesley, MA
0.16
Single-Family Home
$1,530,000
10/30/25
4
3
2,265
365 Weston Rd, Wellesley, MA
0.25
Single-Family Home
$1,010,000
12/03/25
4
2
1,743
13 Cavanaugh Rd, Wellesley, MA
0.12
Single-Family Home
$2,250,000
12/02/25
4
2.5
2,965
428 Weston Rd, Wellesley, MA
0.13
Single-Family Home
$1,497,200
12/09/25
5
3.5
2,558
851 Worcester St, Wellesley, MA
0.44
Single-Family Home
$830,000
06/22/26
4
1.5
1,932
50 Parker Rd, Wellesley, MA
0.31
Single-Family Home
$1,600,000
11/14/25
4
2.5
2,147
6 Boulder Brook Rd, Wellesley, MA
0.15
Single-Family Home
$1,925,000
04/15/26
4
3.5
2,813
45 Shirley Rd, Wellesley, MA
0.37
Single-Family Home
$1,552,000
08/14/25
4
1.5
2,306
31 Martin Rd, Wellesley, MA
0.35
Single-Family Home
$1,740,000
04/17/26
4
2.5
2,214

Nearby homes

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Assigned Schools

These are the assigned schools for 21 Pine Plain Rd.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Wellesley

At least 124 Trulia users voted on each feature.

  • 92 % Say it's dog friendly

  • 87 % Say parking is easy

  • 85 % Say people would walk alone at night

  • 84 % Say yards are well-kept

  • 80 % Say car is needed

  • 79 % Say there are sidewalks

  • 76 % Say kids play outside

  • 75 % Say there's holiday spirit

  • 74 % Say streets are well-lit

  • 73 % Say there's wildlife

  • 72 % Say it's quiet

  • 70 % Say they plan to stay for at least 5 years

  • 67 % Say it's walkable to restaurants

  • 66 % Say neighbors are friendly

  • 65 % Say there are community events

  • 63 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Mike Holiday
    "Everyone walks their dogs and lets their dogs say hello, most often. People know each other. It’s a great community"
    0
    Flag
  • Emilyperrottet
    "Nothing. It’s a changing neighborhood with a mix of old and new homes. Most of the homes are old and run down. "
    0
    Flag
  • Emilyperrottet
    "I take the Commuter rail from Wellesley to the T subway. 1.5 hours to Cambridge from south station. "
    0
    Flag
  • Trulia User
    "Lots of trails and other dogs in the area, many pet stores in the area as well. Dogs are well behaved and friendly. "
    0
    Flag
  • Shirley L.
    "The walking paths and yearly town celebrations are wonderful! A great sense of community and great schools. "
    0
    Flag
  • Sdipietro369
    "I am a visitor to this area. The neighborhood seems very nice with Babson College right around the corner. Shops within a close distance. "
    3
    Flag
  • Katrina C.
    "You feel you're kids are safe here in town. Everyone is friendly and we're all neighbors. It's a lovely town with a community feeling. "
    2
    Flag
  • Jamie.solomon1
    "I lived in Weston for two years and it’s a delightful town, with gorgeous land and large houses. Usually at least an acre"
    1
    Flag
  • Cmt138
    "Great access to commuter rail from either Wellesley Square or Wellesley Hills. Easy 10-15 min walk. Better parking from Wellesley Square. Usually takes about 1/2 hour to Back Bay. Driving into Boston can take a little more time with traffic to cross town to Mass Pike."
    2
    Flag
  • Laura M.
    "There are lots of dogs in our neighborhood- people walk them all the time. Dogs are welcome at Morse’s pond in the off season. "
    1
    Flag
  • Bruce C.
    "Lots of other dog owners who walk their dogs all the time. Also plenty of space to run with dogs on a trail or away from streets. "
    1
    Flag
  • Keith S.
    "Lots of trails and public spaces. Nationally acclaimed colleges. Variety of great shops and restaurants."
    0
    Flag
  • Srodousakis
    "Wellesley is a beautiful but very privileged neighborhood. It is very safe and people are friendly. Schools are great! There is a cute downtown and generally it’s a great place to raise kids. "
    0
    Flag
  • Molly R.
    "i love my neighborhood. everyone is so kind and welcoming. we often times have little gatherings or block parties. everyone knows each other and we are a very close community. "
    0
    Flag
  • Victoria V.
    "That I live on route 16 and nobody lets me out of my driveway in the morning and I have to leave for work an hour early just because of that."
    0
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LGBTQ Local Legal Protections

Apartments for Rent

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Explore by feature - Pet Friendly

12 pet-friendly rentals in Wellesley, MA

Explore by feature - Garage

10 rentals with a garage in Wellesley, MA

Explore by feature - Air Conditioning

21 rentals with air conditioning in Wellesley, MA

Explore by feature - Washer/dryer

23 rentals with a washer/dryer in Wellesley, MA

Explore by feature - Outdoor Space

7 rentals with an outdoor space in Wellesley, MA

Homes for sale near 21 Pine Plain Rd

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Off Market Homes Near 21 Pine Plain Rd

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Frequently asked questions about 21 Pine Plain Rd

  • What is 21 Pine Plain Rd estimated to be worth?
    Trulia's estimated value for 21 Pine Plain Rd in Wellesley, MA is $1,770,800.
  • What is the price history for 21 Pine Plain Rd?
    21 Pine Plain Rd in Wellesley, MA last sold for $715,000 in June 2006.
  • Is Wellesley a buyer's or seller's market?
    Wellesley is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Wellesley?
    The median sale price in Wellesley is $1.99M. That is up $300K from the prior month.
  • Does 21 Pine Plain Rd have air conditioning?
    Yes, 21 Pine Plain Rd in Wellesley, MA has air conditioning.
  • Does 21 Pine Plain Rd have laundry facilities?
    Yes, 21 Pine Plain Rd in Wellesley, MA has in-unit laundry.