2 Days Ago
Location
369 Sterling Dr, Winter Haven, FL 33884, USA
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Amenities for 369 Sterling Dr
Apartment Amenities
| Ceiling Fan | Central Air |
| Electric Heating | Fireplace |
| Walk-in Closet |
Appliances
| Dishwasher | In-Unit Laundry |
Grounds
| Garage Parking | Outdoor Space |
| Swimming Pool |
Other
| Seven Rooms |
Units, floor plans, amenities, dimensions, details, availability, and prices may be approximate and subject to change. Please contact a community representative for more information.
Policies and fees
Applicants
Applicants
One-time.
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REQUIRED FEES
Security Deposit
One-time. Refundable.
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About 369 Sterling Dr
Property Status: Active Beautiful, fully remodeled home located in the desirable Berryhill community of SE Winter Haven. This spacious one-story home offers over 2,000 square feet of living space and features a brand new resurfaced private pool, brand new vinyl fenced backyard, and modern upgrades throughout. Large in-ground private pool (15x30), Oversized primary suite with walk-in closet, Split-bedroom floor plan, Fireplace in living area, Granite countertops in kitchen, Stainless steel appliances, Updated bathrooms with stone counters, Ceramic tile and laminate flooring, Florida room overlooking the pool, 2-car garage with epoxy flooring Located close to shopping, restaurants, medical facilities, schools, and just minutes from LEGOLAND Florida. Quiet, well-maintained neighborhood, only ONE block from elementary school This home is truly move-in ready and perfect for families, entertaining, or anyone looking for Florida living with a private pool. Office Phone: (877) 366-2213 Copyright © 2026 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
Property highlights
We compared every listing in the surrounding area to determine which amenities are most common. If a building lacks an amenity that most others in the area have, it is a con. If a building has an amenity most others in the area do not, it is a pro. Similarly, price, schools, and size are calculated relative to the size, price, and distance to schools of the other properties nearby.How 369 Sterling Dr compares to other nearby properties.
Positives
- Elementary school nearby
- There is an elementary school 0.1 mile away
- More space
- The 3-bedroom is 497 sqft larger than other listings nearby
- Fireplace
- Upgraded in-unit features
- Images Available
- There are at least 10 photos of this address
- Walk-in closet
- More closet space on average
Address details
| Zip code | 33884 |
|---|---|
| Type | House for rent |
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Rent trends in Winter Haven
3-bedroom apartments at 369 Sterling Dr cost about 10% more than the average rent price for 3-bedroom apartments in Winter Haven.
Median rents as of Feb 21 2026.
Winter Haven
| Month | Median Rent |
|---|---|
| March 2024 | $1,892 |
| April 2024 | $1,898 |
| May 2024 | $1,896 |
| June 2024 | $1,898 |
| July 2024 | $1,869 |
| August 2024 | $1,870 |
| September 2024 | $1,842 |
| October 2024 | $1,799 |
| November 2024 | $1,799 |
| December 2024 | $1,812 |
| January 2025 | $1,844 |
| February 2025 | $1,832 |
| March 2025 | $1,847 |
| April 2025 | $1,862 |
| May 2025 | $1,873 |
| June 2025 | $1,871 |
| July 2025 | $1,860 |
| August 2025 | $1,849 |
| September 2025 | $1,847 |
| October 2025 | $1,816 |
| November 2025 | $1,810 |
| December 2025 | $1,797 |
| January 2026 | $1,811 |
| February 2026 | $1,819 |
Affordability calculator
Can I afford to live at 369 Sterling Dr?
Bedrooms
3 bedroomsRent-to-income ratio
30%
Slide to adjust the percentage of your monthly income you are willing to spend on rent.
The general rule of thumb is to spend around 30% or less of your income on rent.
Recommended income
$80,000/yr
With your selected rent-to-income ratio, you'd ideally want to make $80,000 annually to afford this 3-bedrooms monthly rent price of $2,000.
For more information on rent affordability, visit our rent calculator.
Schools near 369 Sterling Dr
Garden Grove Elementary School
4599 cypress gardens rd
winter haven, FL, 33884
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
Gibbons Street Pk Center
1860 gibbons st e
bartow, FL, 33830
PKPublic
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Internet available near 369 Sterling Dr
Getting around Winter Haven near 369 Sterling 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.
Cycling
4/10
This is semi-bikeable, but you’ll need another way of getting around.
Transit
3/10
There are a few mass transit options within the area.
Points of interest for 369 Sterling Dr, Winter Haven
Groceries
2/10
At least one supermarket within a 30-minute walk
Shopping
3/10
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
5/10
At least one elementary school within a 20-minute walk
High schools
0/10
Closest high school further than a 30-minute walk
Nightlife
1/10
Few or no bars within walking distance
Explore the area around 369 Sterling Dr
La Suerte Oriental Market
3048 Cypress Gardens Rd
Natures Delight
3085 Cypress Gardens Rd
Publix
6031 Cypress Gardens Blvd
Walmart Supercenter
7450 Cypress Gardens Blvd
Frozen Food Express Industries Inc
27994 Hwy 27
Shoe Dreams Boutique
4842 Cypress Gardens Rd
Family Dollar
3082 Cypress Gardens Rd
Bealls Florida
5998 Cypress Gardens Blvd
Rainbow
6021 Cypress Gardens Blvd
Walmart Supercenter
7450 Cypress Gardens Blvd
Dunkin'
6354 Cypress Gardens Blvd
Star Coffee
7018 Summit Cir
Stone Cabin Winter Haven
7000 Cypress Gardens Blvd
Tropical Smoothie Cafe
5721 Cypress Gardens Blvd
Starbucks
5709 Cypress Gardens Blvd
Ovation Bistro & Bar
7130 Cypress Gardens Blvd
Little New Orleans Seafood and Oyster Bar
5654 Cypress Gardens Blvd
Sports Bar Somewhere
5688 Cypress Gardens Blvd
Grape Expectations
5535 Cypress Gardens Blvd
Paddywagon Irish Pub
5535 Cypress Gardens Blvd
Walmart Bakery
7450 Cypress Gardens Blvd
Walmart Bakery
355 Cypress Gardens Blvd
GNC
412 Citi CTR St
Fly Nutrition
200 E Central Ave
Sugar & Slice Bakery
222 W Central Ave
Jac 's Corner
3798 Cypress Gardens Rd
Harry's Old Place
3751 Cypress Gardens Rd
Abed Pizza LLC
3062 Cypress Gardens Rd
Little John's Diner
3080 Cypress Gardens Rd
M J's Pizza & Wings
3062 Cypress Gardens Rd
Cypr Grdns Rd & Lk Ned Village Cir
Legoland
Cypr Grdns Rd & Sterling Dr
Legoland
Cypr Grdns Rd & E Heron Pl Se
Legoland
Cypr Grdns Rd & E Heron Pl Se
Legoland
Cypr Grdns Rd Se & Cypr Pointe Blvd
Legoland
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