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The average rent in Highlands, Winter Springs, as of June 2026, is down 10.57% compared to last month but up 10.5% year-over-year.
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1h ago
Highlands house for rent in Winter Springs
475 Macgregor Rd #NA, Winter Springs, FL 32708
In-unit laundry | Air conditioning | Garage parking
3 beds
2 baths
$2,500
House for rent
Available Jul 1
4d ago
Highlands condo for rent in Winter Springs
80 Moree Loop #9, Winter Springs, FL 32708
In-unit laundry | Assigned parking | Swimming pool
3 beds
2 baths
$1,700
Condo for rent
5d+ ago
Highlands townhouse for rent in Winter Springs
3 beds
2.5 baths
$2,150
House for rent
5d+ ago
Highlands condo for rent in Winter Springs
2 beds
2 baths
$1,700
Condo for rent
5d+ ago
Verified
2 beds
2 baths
$1,775
House for rent
Available May 29
4d ago
House for rent in Winter Springs
1250 N Brassie Dr #NA, Winter Springs, FL 32708
In-unit laundry | Air conditioning | Assigned parking
2 beds
1 bath
$1,975
House for rent
Available Jun 20
Outdoor Space
Dishwasher
Garage Parking
Swimming Pool
5d+ ago
North Orlando house for rent in Winter Springs
3 beds
2 baths
$2,495
$2,395
Price drop
House for rent
Available Jun 10
20h ago
Apartment for rent in Winter Springs
2 beds
2 baths
$1,500
$1,395
Price drop
Apartment for rent
Be the first to hear about new listings matching your search.
2h ago
1–3 beds
1–2 baths
$1,214–$1,900
Price drop
Apartment for rent
1d ago
North Orlando house for rent in Winter Springs
3 beds
2 baths
$2,399
$2,299
Price drop
House for rent
Available Jun 5
5d+ ago
Townhouse for rent in Winter Springs
2 beds
1.5 baths
$1,495
House for rent
Available May 25
5d+ ago
House for rent in Winter Springs
2 beds
1.5 baths
$1,495
House for rent
5d+ ago
North Orlando townhouse for rent in Winter Springs
2 beds
2 baths
$1,515
House for rent
5d+ ago
North Orlando apartment for rent in Winter Springs
2 beds
1.5 baths
$1,515
Apartment for rent
These rentals are 10%-30% cheaper than the local average price for similar rentals.
5d+ ago
House for rent in Casselberry
3 beds
2.5 baths
$2,550
House for rent
5d+ ago
Townhouse for rent in Winter Springs
207 S Moss Rd, Winter Springs, FL 32708
In-unit laundry | Ceiling fan | Dishwasher
2 beds
1.5 baths
$1,495
House for rent
5d+ ago
North Orlando house for rent in Winter Springs
228 Bitterwood St, Winter Springs, FL 32708
Swimming pool | Storage | Outdoor space
3 beds
2 baths
$2,305
House for rent
5d+ ago
House for rent in Longwood
828 Shell Ln, Longwood, FL 32750
Swimming pool | Storage | Outdoor space
3 beds
2 baths
$2,270
House for rent
5d+ ago
House for rent in Casselberry
4 beds
3.5 baths
$2,725
House for rent
5d+ ago
North Orlando house for rent in Winter Springs
212 S Cortez Ave #NA, Winter Springs, FL 32708
In-unit laundry | Furnished | Air conditioning
4 beds
3 baths
$2,400
House for rent
Available Jun 15
3d ago
House for rent in Winter Springs
3 beds
2 baths
$2,149
House for rent
Available Jun 4
2d ago
North Orlando house for rent in Winter Springs
116 S Moss Rd, Winter Springs, FL 32708
Swimming pool
4 beds
2 baths
$2,590
House for rent
5d+ ago
North Orlando house for rent in Winter Springs
109 N Alderwood St, Winter Springs, FL 32708
Swimming pool | Storage | Outdoor space
3 beds
2 baths
$2,155
House for rent
3d ago
1450 Sunshadow Dr, Casselberry, FL 32707
In-unit laundry | Swimming pool | Fitness center
1–2 beds
1–2 baths
$1,199–$1,744
Apartment for rent
5d+ ago
Verified
3 beds
2 baths
$2,480
House for rent
Available Jun 5
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One-bedroom apartments in Highlands average around $1,400 per month in 2025. These units typically offer around 762 square feet of living space.
Two-bedroom apartments in Highlands rent for around $1,600 per month in 2025. These units average approximately 1,046 square feet of space.
Three-bedroom apartments in Highlands average around $2,100 per month in 2025. These larger units typically provide around 1,425 square feet of living space.
Highlands, a neighborhood in Winter Springs, averaged around $2,000 per month in 2025, with rent rising sharply from 2024. One-bedroom units provide the most affordable option at around $1,400 monthly, while three-bedroom apartments reach around $2,100.
In Highlands, apartments average around 1,304 square feet across all unit types. Unit sizes range from around 762 square feet for one-bedroom apartments to approximately 1,425 square feet for three-bedroom units.
Three-bedroom apartments are the most common rental type in Highlands, with about 9 listings available monthly. The neighborhood sees a total of approximately 13 rental listings per month across all bedroom types.
Highlands in Winter Springs is a neighborhood that perfectly complements an active social lifestyle. Our analysis of local data reveals that the area's population density, frequent transit options, well-maintained street infrastructure, high walk score, and emphasis on safety create an ideal environment for those who value community interaction and social connections. With these amenities, residents can easily get around, meet new people, and engage in local activities, making Highlands an excellent choice for those seeking a vibrant social life. If you're looking for a neighborhood that fosters connections and community, Highlands is definitely worth considering.
One-bedroom apartments have the fewest listings in Highlands, averaging about 1 per month. Two-bedroom units are also relatively limited, with approximately 3 listings available monthly.
Zumper’s proprietary rental data fuels our analysis. Rent and market trends, availability, neighborhood popularity, and lifestyle scores are all calculated using real-time and 2026 rental inventory and prices.
Our Lifestyle Categories ("great for eco-living," "great for social life," "great for pet owners," etc.) are determined by set criteria, against which we score each listing and its available features. At the neighborhood level, we calculate the listing count for each category to determine which lifestyles best fit each area.
Zumper, founded in 2012, is North America’s largest privately-owned rental platform, offering over 1 million listings across the U.S. and Canada. Stay informed on the latest trends and shifts in the rental market with our monthly National Rent Report, your go-to resource for key insights into the evolving rental landscape.
| 🔑Available apartment rentals | 25 |
|---|---|
| 💰Best rent deal | 1 Laurel Oaks Dr |
| ✨Popular amenities | , , |
| 🍽With dishwasher | |
| 🏠With photos |