Seller's Agent in 2025
Jennifer Fish
Gibson Sotheby's International Realty
(617) 291-8001
1 in this area
2 Total Sales
21 Cushing Rd Wellesley Hills, MA 02481
Cliff Estates Neighborhood
5
Beds
6
Baths
4,558
Sq Ft
0.35
Acres
Highlights
- Media Room
- Open Floorplan
- Colonial Architecture
- Ernest F. Upham Elementary School Rated A+
- Custom Closet System
- Landscaped Professionally
About This Home
As of May 2025Discover luxury and sophistication in this renovated/expanded 5-bedroom, 6-bathroom Cliff Estates masterpiece. Set on a manicured lot, this home offers 4 levels of meticulously designed living space. The grand foyer leads to elegant living and dining areas with custom millwork, rich hardwood floors, and oversized windows. The chef’s kitchen boasts an oversized island, top-tier appliances, wet bar, and cozy fireplace, flowing into a spacious family room beaming with natural sun lighting and a statement fireplace. First-floor office, well-appointed mudroom, and 3-car heated garage add convenience. The luxurious primary suite features a spa-like bath, walk-in closets, and fireplace. Three additional bedrooms and charming window-seat nook complete the second floor. The third level offers a private suite, while the finished lower level includes a media room, playroom, and storage. Close proximity to train, restaurants, and shops. Seller welcomes offers with requests for buyer concessions.
Last Agent to Sell the Property
Gibson Sotheby's International Realty Listed on: 03/17/2025
Home Details
Home Type
- Single Family
Est. Annual Taxes
- $31,220
Year Built
- Built in 1909 | Remodeled
Lot Details
- 0.35 Acre Lot
- Stone Wall
- Landscaped Professionally
- Level Lot
- Sprinkler System
- Property is zoned SR20
Parking
- 3 Car Attached Garage
- Tuck Under Parking
- Parking Storage or Cabinetry
- Heated Garage
- Garage Door Opener
- Driveway
- Open Parking
- Off-Street Parking
Home Design
- Colonial Architecture
- Stone Foundation
- Frame Construction
- Shingle Roof
- Concrete Perimeter Foundation
- Stone
Interior Spaces
- Open Floorplan
- Wet Bar
- Crown Molding
- Tray Ceiling
- Ceiling Fan
- Recessed Lighting
- Decorative Lighting
- Light Fixtures
- Picture Window
- French Doors
- Mud Room
- Family Room with Fireplace
- 3 Fireplaces
- Dining Area
- Media Room
- Home Office
- Play Room
- Home Security System
Kitchen
- Oven
- Stove
- Range
- Microwave
- Freezer
- Second Dishwasher
- Stainless Steel Appliances
- Kitchen Island
- Solid Surface Countertops
- Disposal
Flooring
- Wood
- Ceramic Tile
Bedrooms and Bathrooms
- 5 Bedrooms
- Fireplace in Primary Bedroom
- Primary bedroom located on second floor
- Custom Closet System
- Linen Closet
- Walk-In Closet
- Pedestal Sink
- Dual Vanity Sinks in Primary Bathroom
- Separate Shower
- Linen Closet In Bathroom
Laundry
- Laundry on upper level
- Dryer
- Washer
- Sink Near Laundry
Finished Basement
- Walk-Out Basement
- Basement Fills Entire Space Under The House
- Interior Basement Entry
- Garage Access
Eco-Friendly Details
- Energy-Efficient Thermostat
Outdoor Features
- Deck
- Rain Gutters
Location
- Property is near public transit
- Property is near schools
Schools
- Wps Elementary School
- WMS Middle School
- WHS High School
Utilities
- Central Heating and Cooling System
- 6 Heating Zones
- Heating System Uses Natural Gas
Listing and Financial Details
- Assessor Parcel Number 259772
Community Details
Overview
- No Home Owners Association
- Cliff Estates Subdivision
- Near Conservation Area
Amenities
- Shops
Recreation
- Tennis Courts
- Jogging Path
Ownership History
Date
Name
Owned For
Owner Type
Purchase Details
Listed on
Mar 17, 2025
Closed on
Apr 28, 2025
Sold by
21 Cushing Rt and Lane
Bought by
Gorham Alexander and Gorham Courtnay B
Seller's Agent
Jennifer Fish
Gibson Sotheby's International Realty
Buyer's Agent
The Collective
Compass
List Price
$3,790,000
Sold Price
$3,700,000
Premium/Discount to List
-$90,000
-2.37%
Views
17
Current Estimated Value
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Estimated Appreciation
$13,500
Avg. Annual Appreciation
0.66%
Purchase Details
Listed on
Nov 3, 2022
Closed on
Feb 23, 2023
Sold by
21 Cushing Road Llc
Bought by
21 Cushing Rt and Lane
Seller's Agent
Melissa Dailey
Coldwell Banker Realty - Wellesley
Buyer's Agent
The Lara & Chelsea Collaborative
Coldwell Banker Realty - Wellesley
List Price
$3,395,000
Sold Price
$3,325,000
Premium/Discount to List
-$70,000
-2.06%
Views
76
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Avg. Annual Appreciation
5.02%
Purchase Details
Listed on
Feb 28, 2022
Closed on
Apr 19, 2022
Sold by
Simko Gregory and Simko Tracy
Bought by
21 Cushing Road Llc
Seller's Agent
Benoit | Robinso Orourke
Gibson Sotheby's International Realty
Buyer's Agent
Benoit | Robinso Orourke
Gibson Sotheby's International Realty
List Price
$2,750,000
Sold Price
$3,175,000
Premium/Discount to List
$425,000
15.45%
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Avg. Annual Appreciation
5.51%
Original Mortgage
$2,222,500
Interest Rate
2.6%
Mortgage Type
Purchase Money Mortgage
Purchase Details
Closed on
Mar 18, 2011
Sold by
Kilgore Robert D and Kilgore Melissa P
Bought by
Simko Gregory S and Simko Tracy L
Purchase Details
Closed on
Aug 5, 2009
Sold by
Crowley Gregory G and Crowley Mary S
Bought by
Kilgore Robert D and Kilgore Melissa P
Purchase Details
Closed on
May 2, 1991
Sold by
Wooden Douglas L and Wooden Mariette M
Bought by
Crowley Gregory G
Create a Home Valuation Report for This Property
The Home Valuation Report is an in-depth analysis detailing your home's value as well as a comparison with similar homes in the area
Home Values in the Area
Average Home Value in this Area
Purchase History
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Quit Claim Deed | $3,700,000 | None Available | |
| Quit Claim Deed | $3,700,000 | None Available | |
| Quit Claim Deed | $3,325,000 | None Available | |
| Quit Claim Deed | $3,325,000 | None Available | |
| Quit Claim Deed | $3,175,000 | None Available | |
| Quit Claim Deed | $3,175,000 | None Available | |
| Deed | $1,175,000 | -- | |
| Deed | $1,175,000 | -- | |
| Deed | $1,175,000 | -- | |
| Deed | $1,100,000 | -- | |
| Deed | $1,100,000 | -- | |
| Deed | $1,100,000 | -- | |
| Deed | $375,000 | -- | |
| Deed | $375,000 | -- |
Source: Public Records
Mortgage History
| Date | Status | Loan Amount | Loan Type |
|---|---|---|---|
| Previous Owner | $2,222,500 | Purchase Money Mortgage | |
| Previous Owner | $100,000 | No Value Available | |
| Previous Owner | $50,000 | No Value Available |
Source: Public Records
Property History
| Date | Event | Price | List to Sale | Price per Sq Ft | Prior Sale |
|---|---|---|---|---|---|
| 05/01/2025 05/01/25 | Sold | $3,700,000 | -2.4% | $812 / Sq Ft | |
| 03/30/2025 03/30/25 | Pending | -- | -- | -- | |
| 03/17/2025 03/17/25 | For Sale | $3,790,000 | +14.0% | $832 / Sq Ft | |
| 02/27/2023 02/27/23 | Sold | $3,325,000 | -2.1% | $729 / Sq Ft | View Prior Sale |
| 01/19/2023 01/19/23 | Pending | -- | -- | -- | |
| 01/06/2023 01/06/23 | For Sale | $3,395,000 | +2.1% | $745 / Sq Ft | |
| 12/15/2022 12/15/22 | Off Market | $3,325,000 | -- | -- | |
| 11/03/2022 11/03/22 | For Sale | $3,395,000 | +6.9% | $745 / Sq Ft | |
| 04/19/2022 04/19/22 | Sold | $3,175,000 | +15.5% | $697 / Sq Ft | View Prior Sale |
| 03/03/2022 03/03/22 | Pending | -- | -- | -- | |
| 02/28/2022 02/28/22 | For Sale | $2,750,000 | -- | $603 / Sq Ft |
Source: MLS Property Information Network (MLS PIN)
Tax History Compared to Growth
Tax History
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $31,220 | $3,037,000 | $1,036,000 | $2,001,000 |
| 2024 | $30,335 | $2,914,000 | $987,000 | $1,927,000 |
| 2023 | $31,064 | $2,713,000 | $874,000 | $1,839,000 |
| 2022 | $18,279 | $1,565,000 | $783,000 | $782,000 |
| 2021 | $18,013 | $1,533,000 | $751,000 | $782,000 |
| 2020 | $17,721 | $1,533,000 | $751,000 | $782,000 |
| 2019 | $17,505 | $1,513,000 | $751,000 | $762,000 |
| 2018 | $19,072 | $1,596,000 | $859,000 | $737,000 |
| 2017 | $18,569 | $1,575,000 | $859,000 | $716,000 |
| 2016 | $18,171 | $1,536,000 | $844,000 | $692,000 |
| 2015 | $17,779 | $1,538,000 | $844,000 | $694,000 |
Source: Public Records
Agents Affiliated with this Home
-
Jennifer Fish
-
The Collective
T
Buyer's Agent in 2025
The Collective
Compass
(617) 807-0853
1 in this area
142 Total Sales
-
Melissa Dailey
Seller's Agent in 2023
Melissa Dailey
Coldwell Banker Realty - Wellesley
(781) 237-9090
35 in this area
342 Total Sales
-
K
Seller Co-Listing Agent in 2023
Kathryn Alphas Richlen
Coldwell Banker Realty - Weston
-
The Lara & Chelsea Collaborative
Buyer's Agent in 2023
The Lara & Chelsea Collaborative
Coldwell Banker Realty - Wellesley
(617) 686-4110
8 in this area
165 Total Sales
-
B
Seller's Agent in 2022
Benoit | Robinso Orourke
Gibson Sotheby's International Realty
Map
Source: MLS Property Information Network (MLS PIN)
MLS Number: 73346403
APN: WELL-000084-000011
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