26 Skyline Dr
Wellesley, MA 02482
- 4 Beds
- 4 Baths
- 2,905 sqft (on 0.81 acres)
4 Beds
4 Baths
2,905 sqft
(on 0.81 acres)
Local Information
-- mins to
Description
Set on nearly an acre of tranquil grounds sits this enchanting home surrounded by exquisite landscaping. Meticulously maintained, this special offering has many functional sparkling living spaces to work and play. The open floor plan from the kitchen to the sun filled and fireplaced living room is perfect for relaxing and entertaining. From there it flows into the dining room with large, crown molding and 9 pane windows. A screened in porch with new flooring, screens and glass, for reading, dining or enjoying cocktails next to the outdoor fireplace while overlooking the second private patio. Each bedroom is spacious including an inviting master suite with an enormous spa tub, and skylight. Huge walk in Master Closet with window. The lower level makes for a perfect playroom, home gym or au pair suite, with full bath and wet bar. NEW ROOF and two car garage complete this package! Close to town walking trails and near Wellesley center. This lovely property is on an wooded ended way!
26 Skyline Dr, Wellesley, MA 02482 is a 4 bedroom, 4 bathroom, 2,905 sqft single-family home built in 1955. It last sold for $1,390,000 on Sep 18, 2020. More recently, it was listed as a rental in March 2014 with an asking price of $5,500 per month. That rental listing was removed on April 14, 2014. It is currently off market. The Trulia Estimate is $2,669,100, with a rent estimate of $7,694/month.
Home Highlights
Parking
Garage
Outdoor
Patio
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago
Home Details for 26 Skyline Dr
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Heating & Cooling Heating: Baseboard, Radiant, GasHeating Fuel: Baseboard |
Levels, Entrance, & Accessibility Stories: 2Floors: Tile, Carpet, Hardwood |
Interior Details Number of Rooms: 8Types of Rooms: Dining Room, Family Room, Master BathWet Bar |
Appliances & Utilities DishwasherDisposalDryerMicrowaveRefrigeratorWasher |
Fireplace & Spa Fireplace |
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Exterior Home Features Roof: AsphaltExterior: WoodPatio |
Parking & Garage GarageParking Spaces: 4Parking: Garage Attached |
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Year Built Year Built: 1955Year Updated: 2021 |
Property Type / Style Property Type: Single Family HomeArchitecture: split level |
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Units in Building: 1 |
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Lot Area: 0.81 acres |
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Fitness & Sports Tennis Court |
Price History for 26 Skyline Dr
| Date | Price | Event | Source |
|---|---|---|---|
| 09/18/2020 | $1,390,000 | Sold | N/A |
| 08/06/2020 | $1,395,000 | PriceChange | Agent Provided |
| 07/10/2020 | $1,449,000 | PriceChange | Agent Provided |
| 06/27/2020 | $1,535,000 | Listed For Sale | Agent Provided |
| 01/30/2017 | $1,300,000 | Sold | N/A |
| 04/14/2014 | $5,500 | ListingRemoved | Agent Provided |
| 03/19/2014 | $5,500 | Listed For Rent | Agent Provided |
| 07/14/2008 | $875,000 | Sold | N/A |
| 05/28/1993 | $380,000 | Sold | N/A |
Market trends in Wellesley
Last updated May 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
111
3MoM
Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $19,141 |
| Assessment | $1,862,000 |
Home facts updated by county records
Comparable Sales for 26 Skyline Dr
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.07 | Single-Family Home | $2,400,000 | 01/30/26 | 4 | 4 | 4,304 | |
0.33 | Single-Family Home | $1,850,000 | 04/09/26 | 4 | 2.5 | 3,016 | |
0.14 | Single-Family Home | $2,400,000 | 08/29/25 | 4 | 4.5 | 6,373 | |
0.40 | Single-Family Home | $2,625,000 | 04/30/26 | 4 | 3.5 | 3,433 | |
0.55 | Single-Family Home | $3,305,000 | 06/26/26 | 4 | 3.5 | 3,738 | |
0.36 | Single-Family Home | $2,210,000 | 07/17/25 | 4 | 2.5 | 3,511 | |
0.57 | Single-Family Home | $2,225,000 | 06/12/26 | 5 | 3.5 | 2,590 | |
0.57 | Single-Family Home | $2,405,000 | 11/03/25 | 4 | 2.5 | 3,144 | |
0.51 | Single-Family Home | $2,040,000 | 06/02/26 | 5 | 3 | 2,465 | |
0.60 | Single-Family Home | $1,580,000 | 05/08/26 | 4 | 4 | 2,375 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.Assigned Schools
These are the assigned schools for 26 Skyline Dr.
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.
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