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Updated 5+ Days Ago
Location
29 Winston Dr, Belleair, FL 33756, USA
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Policies and fees
Applicants
Applicants
One-time.
Contact Property
REQUIRED FEES
Security Deposit
One-time. Refundable.
Contact Property
Dog Policy
Not allowed
Cat Policy
Not allowed
No pets allowed.
About 29 Winston Dr
Belleair Waterfront 3 bedroom 2 bath home in absolutely vintage and pristine condition, located on Winston Drive. This home is a must see, new carpet, new furniture, beautiful water views, large heated pool with view of the wide open intra-coastal. This is a maintenance free home as the owner provides all lawn and ground care, pool and pest control. Move in Ready. This home is available for a minimum of 7 months and as long as 12 months. Room measurements are estimated and to be verified.
Address details
| Zip code | 33756 |
|---|---|
| Type | House for rent |
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Available rentals nearby
Mystic Bay Apartments
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$2,220–$4,642
Additional fees apply. The price shown reflects base rent. Based on information provided by the property, additional fees may apply, but no required monthly charges have been confirmed. See all fees for details.
Waterchase Apartments
Our team has verified this company401 Rosery Rd Ne
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$2,427–$4,650
Additional fees apply. The price shown reflects base rent. Based on information provided by the property, additional fees may apply, but no required monthly charges have been confirmed. See all fees for details.
10464 Hetrick Cir W
3 Beds
$3,490
Additional fees apply. The price shown reflects base rent. Based on information provided by the property, additional fees may apply, but no required monthly charges have been confirmed. See all fees for details.
Mystic Bay Apartments
Our team has verified this company600 Starkey Rd
3 Beds
$2,220–$4,642
Additional fees apply. The price shown reflects base rent. Based on information provided by the property, additional fees may apply, but no required monthly charges have been confirmed. See all fees for details.Waterchase Apartments
Our team has verified this company401 Rosery Rd Ne
3 Beds
$2,427–$4,650
Additional fees apply. The price shown reflects base rent. Based on information provided by the property, additional fees may apply, but no required monthly charges have been confirmed. See all fees for details.10464 Hetrick Cir W
3 Beds
$3,490
Additional fees apply. The price shown reflects base rent. Based on information provided by the property, additional fees may apply, but no required monthly charges have been confirmed. See all fees for details.Rent trends in Belleair
3-bedroom apartments at 29 Winston Dr cost about 12% less than the average rent price for 3-bedroom apartments in Belleair.
Median rents as of Oct 17 2026.
Belleair
| Month | Median Rent |
|---|---|
| November 2024 | $3,440 |
| April 2025 | $5,383 |
| May 2025 | $4,599 |
| June 2025 | $5,337 |
| July 2025 | $5,250 |
| August 2025 | $4,900 |
| September 2025 | $5,500 |
| October 2025 | $4,005 |
| November 2025 | $3,634 |
| December 2025 | $3,799 |
| January 2026 | $3,921 |
| February 2026 | $3,787 |
| March 2026 | $4,500 |
| August 2026 | $4,350 |
| September 2026 | $4,387 |
| October 2026 | $4,100 |
Rent history
The increase or decrease in monthly rent compared to the previous listing price.| 7 years ago | $3,600 |
Schools near 29 Winston Dr
Mildred Helms Elementary School
561 clearwater largo rd s
largo, FL, 33770
PK, K-5Public
B
Dropout Prevention School
301 4th st sw
largo, FL, 33770
PK, K-12Public
Pinellas Virtual Franchise
305 4th ave sw
largo, FL, 33770
K-12Public
A-
Largo High School
410 missouri ave n
largo, FL, 33770
PK, 9-12Public
A-
Calvin A. Hunsinger School
1863 n betty ln
clearwater, FL, 33755
K-12Public
Neighborhood
Getting around Belleair near 29 Winston Dr
Walking
4/10
Fewer daily needs are within walking distance (unless you’re up for a challenge).
Driving
8/10
This area is close to freeways and has adequate parking options.
Transit
1/10
FYI, there are little to no public transit options within walking distance.
Points of interest for 29 Winston Dr, Belleair
Groceries
5/10
The nearest general grocery store is within a 15-minute walk, and there are also a few specialist food stores nearby.
Shopping
4/10
Some fashion stores are within walking distance.
Cafes
4/10
The closest café is within a 15-minute walk, and there are a few other cafés within walking distance.
Restaurants
4/10
Some restaurants are within walking distance.
Parks
4/10
Few parks in the area.
Nightlife
1/10
No bars are within walking distance.
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