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Updated 5+ Days Ago
Location
280 Santa Rosa Dr, Winter Haven, FL 33884, USA|Overlook Estates
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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.
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About 280 Santa Rosa Dr
Beautiful Pool home in the Overlook Estates area of Polk County. This is a gated SE community featuring 4 bedrooms, 2 baths, or 3 bedrooms, 2 baths with office. This is a pool home with approximately 2,251 sq ft living, open floor plan with divided bedrooms, living room plus gathering room with fireplace, inside utility room, large bedrooms throughout, tons of storage everywhere and outside fun with pool and entertaining area. Dogs and Cats on a case-by-case basis. If approved by owner, must have pet liability insurance. Washer and Dryer hookups Lessee(s) must provide proof of liability insurance for $100,000 before occupancy. Real Property Management South Orlando can provide the required coverage for an additional charge of $12.00 per month, or you can purchase coverage from your preferred provider. To see all of our available properties, check our primary site at www rpmsouthorlando com Application Fee = $75 per adult Security Deposit = $2599.00 Lease Admin Fee (CERTIFIED FUNDS ONLY) = $125.00 First Month's Rent (CERTIFIED FUNDS ONLY) = $2599 Pet Fee ( Non-Refundable ) = $300 Pet Deposit $300 **The following breeds or mixes will not be accepted under any circumstances, DOBERMANS, PIT BULLS, CHOWS, ROTWEILLERS, and GERMAN SHEPPARD. All owners must complete a PetScreening as part of the application process. Pet application is $20 per pet Pet fee of $300 per pet Pet Deposit $300 Monthly pet rent of $30 per pet INFORMATION IS DEEMED RELIABLE, BUT IS NOT GUARANTEED, AND SUBJECT TO CHANGE WITHOUT NOTICE. (John L. Wilkerson, Florida Real Estate Broker) Contact: 727-420-9334 Property Manager - Ruperi Shah Real Property Management South Orlando and Lakeside YouTube Video URL --
Address details
| Neighborhood | Overlook Estates |
|---|---|
| Zip code | 33884 |
| Type | House for rent |
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4-bedroom apartments at 280 Santa Rosa Dr cost about 21% more than the average rent price for 4-bedroom apartments in Cypress Gardens.
Median rents as of Oct 3 2026.
Cypress Gardens
| Month | Median Rent |
|---|---|
| July 2025 | $2,600 |
| August 2025 | $2,251 |
| September 2025 | $2,226 |
| October 2025 | $2,141 |
| February 2026 | $2,299 |
| March 2026 | $2,299 |
| May 2026 | $2,190 |
| June 2026 | $2,190 |
| September 2026 | $2,408 |
| October 2026 | $2,148 |
Rent history
The increase or decrease in monthly rent compared to the previous listing price.| 2 years ago | $2,599 |
Schools near 280 Santa Rosa Dr
Elbert Elementary School
205 15th st ne
winter haven, FL, 33881
PK, K-5Public
C
Winter Haven Head Start
135 ave y ne
winter haven, FL, 33881
PKPublic
Ridge Technical Academy
7700 state rd 544
winter haven, FL, 33881
PK, 6-12Public
Karen M. Siegel Academy
935 evenhouse rd
lake alfred, FL, 33850
PK, K-12Public
Davenport A.
8 w palmetto st
davenport, FL, 33837
PK, K-5Public
C-
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Internet available near 280 Santa Rosa Dr
Neighborhood
Overlook Estates | Cypress Gardens, FL
Getting around Winter Haven near 280 Santa Rosa Dr
Walking
3/10
Fewer daily needs are within walking distance (unless you’re up for a challenge).
Driving
8/10
Commuting is easy with multiple accessible routes and plenty of parking.
Points of interest for 280 Santa Rosa Dr, Winter Haven
Groceries
2/10
No grocery stores within walking distance
Shopping
4/10
Some shops within walking distance
Cafes
2/10
Few or no cafés within walking distance
Restaurants
4/10
Some restaurants within walking distance
Primary schools
0/10
No elementary schools within a 30-minute walk
High schools
0/10
No high schools within a 30-minute walk
Nightlife
2/10
Few or no bars within walking distance
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