Seller's Agent in 2025
Gayle Winters
Compass
(617) 699-0310
3 in this area
198 Total Sales
Welcome to 185 Oakley Rd, a stunning oversized two-family home brimming with character and investment potential. Perfectly positioned on a coveted corner lot in Payson Park across from the middle school, this expansive property seamlessly blends timeless charm with modern convenience. Inside, both units boast soaring ceilings, French doors, elegant moldings, and abundant natural light that fills the bright, sun-drenched rooms. Unit 1 features 3 bedrooms, 1 bath, and an updated kitchen, while Unit 2 spans two levels with 4 bedrooms, 1.5 baths, and breathtaking Boston views from the third floor. Both units offer expansive living and dining areas, a sunroom perfect for a home office, and beautiful hardwood floors throughout. Recent upgrades include brand-new water heaters for both units, a new boiler, fresh paint, and refinished floors in Unit 2. A two-car attached garage plus two driveway spaces provide ample parking. With 15 spacious rooms and flexible living spaces, this home is ideal.
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Deed | $1,452,500 | -- | |
| Deed | $1,452,500 | -- | |
| Quit Claim Deed | -- | None Available | |
| Quit Claim Deed | -- | None Available | |
| Quit Claim Deed | -- | None Available | |
| Quit Claim Deed | -- | None Available | |
| Quit Claim Deed | -- | None Available | |
| Quit Claim Deed | -- | None Available | |
| Quit Claim Deed | -- | None Available | |
| Quit Claim Deed | -- | None Available |
| Date | Status | Loan Amount | Loan Type |
|---|---|---|---|
| Open | $1,016,750 | Purchase Money Mortgage | |
| Closed | $1,016,750 | New Conventional |
| Date | Event | Price | List to Sale | Price per Sq Ft |
|---|---|---|---|---|
| 08/01/2025 08/01/25 | Sold | $1,452,500 | -3.1% | $371 / Sq Ft |
| 06/11/2025 06/11/25 | Pending | -- | -- | -- |
| 06/04/2025 06/04/25 | For Sale | $1,499,000 | -- | $383 / Sq Ft |
| 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 | $17,153 | $1,506,000 | $714,000 | $792,000 |
| 2024 | $15,132 | $1,433,000 | $801,000 | $632,000 |
| 2023 | $14,320 | $1,274,000 | $755,000 | $519,000 |
| 2022 | $14,113 | $1,236,000 | $729,000 | $507,000 |
| 2021 | $14,113 | $1,223,000 | $722,000 | $501,000 |
| 2020 | $13,739 | $1,249,000 | $745,000 | $504,000 |
| 2019 | $12,720 | $1,090,000 | $623,000 | $467,000 |
| 2018 | $12,502 | $1,029,000 | $567,000 | $462,000 |
| 2017 | $12,398 | $977,000 | $520,000 | $457,000 |
| 2016 | $12,233 | $974,000 | $520,000 | $454,000 |
| 2015 | $10,926 | $847,000 | $405,000 | $442,000 |
Seller's Agent in 2025
Gayle Winters
Compass
(617) 699-0310
3 in this area
198 Total Sales
D
Seller Co-Listing Agent in 2025
Dana Dunne
Compass
1 in this area
11 Total Sales
Source: MLS Property Information Network (MLS PIN)
MLS Number: 73385779
APN: BELM-000007-000038