Rentometer, Inc. | Data as of 10/22/2025
Winchester offers a vibrant rental market that blends historic charm with modern convenience, making it a sought‑after suburb for professionals, families, and students alike. Its walkable downtown, anchored by the classic Winchester Town Hall and a variety of boutique shops and cafés, provides a lively urban feel while still benefiting from easy access to Boston via the commuter rail. Green spaces such as the Middlesex Fells Reservation and the scenic South Common park add an outdoor dimension that appeals to active renters looking for trails, picnics, and community events.
Apartment options in Winchester cater to a range of lifestyles. Studio units typically rent in the $2300s, offering a cost‑effective entry point for singles or those seeking a low‑maintenance space. One‑bedroom apartments often fall within the $2600–$3000 range, providing comfortable living for couples or professionals. Larger families may gravitate toward two‑bedroom apartments, commonly found in the $3700s, while three‑bedroom units approach the $5600–$6000 bracket, delivering ample room for households seeking space and proximity to top‑rated schools.
For renters desiring a more expansive setting, the town’s historic homes present an attractive alternative. Four‑plus bedroom houses command rents in the $8000–$8800 range, reflecting the blend of premium space, architectural character, and the prestige of Winchester’s renowned residential neighborhoods. Whether drawn by the town’s cultural venues, acclaimed public schools, or its convenient commuter links, renters in Winchester enjoy a balanced mix of suburban tranquility and urban accessibility.
| Property Type | Bedrooms | Average | Median | Min - Max | 25th - 75th |
|---|---|---|---|---|---|
| Apartment | Studio | $2,349 | $2,132 | $1,700 - $3,435 | $1,895 - $3,435 |
| Apartment | 1 Bedroom | $2,624 | $2,907 | $1,025 - $4,029 | $1,789 - $3,339 |
| Apartment | 2 Bedroom | $3,710 | $3,742 | $880 - $5,739 | $3,200 - $4,503 |
| Apartment | 3 Bedroom | $5,982 | $5,609 | $4,660 - $8,870 | $5,029 - $6,585 |
| House | 4+ Bedroom | $8,825 | $7,500 | $4,950 - $15,000 | $7,000 - $11,000 |
In the current period, the average rent in Winchester was $2,350 for Studio, $2,625 for 1 Bedroom, $3,710 for 2 Bedroom, $5,651 for 3 Bedroom, and $9,500 for 4+ Bedroom.
Data provided by Rentometer, Inc.