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The average rent in Highlands, Winter Springs, as of July 2026, is up 23.44% compared to last month but down 1.57% year-over-year.
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5d+ ago
Verified
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
3d ago
Highlands condo for rent in Winter Springs
1 bed
1 bath
$1,350
Condo for rent
5d+ ago
Highlands house for rent in Winter Springs
47 Macgregor Rd, Winter Springs, FL 32708
In-unit laundry | Air conditioning | Garage parking
3 beds
2 baths
$2,500
House for rent
Available Jul 1
5d+ 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
4d ago
House for rent in Winter Springs
3 beds
2 baths
$1,900
House for rent
Available Jul 15
2d 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
$1,800
House for rent
Available Jun 20
Dishwasher
Outdoor Space
Swimming Pool
In-Unit Laundry
5d+ ago
North Orlando house for rent in Winter Springs
3 beds
2 baths
$2,395
$2,295
Price drop
House for rent
Available Jun 10
5d+ ago
Apartment for rent in Winter Springs
2 beds
2 baths
$1,395
Apartment for rent
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3d ago
1–3 beds
1–2 baths
$1,119–$1,900
Price drop
Apartment for rent
5d+ ago
Verified
409 S Hawthorn Cir, Winter Springs, FL 32708
Garage parking | Outdoor space
3 beds
2 baths
$2,045
House for rent
Available Jul 20
5d+ ago
House for rent in Winter Springs
2 beds
1.5 baths
$1,450
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
$1,495
Apartment 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
These rentals are 10%-30% cheaper than the local average price for similar rentals.
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
$2,255
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
5d+ 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
1450 Sunshadow Dr, Casselberry, FL 32707
In-unit laundry | Swimming pool | Fitness center
1–2 beds
1–2 baths
$1,299–$1,693
Price drop
Apartment for rent
5d+ ago
House for rent in Longwood
3 beds
2 baths
$2,295
House for rent
3d ago
Townhouse for rent in Longwood
4 beds
3.5 baths
$2,995
House for rent
1d ago
Verified
3 beds
2 baths
$2,470
House for rent
Available Sep 21
5d+ ago
Verified
3 beds
2 baths
$3,630
$2,590
Price drop
House for rent
Available Jul 30
5d+ ago
Verified
3 beds
2.5 baths
$2,375
House for rent
Available Jun 25
5d+ ago
Verified
3 beds
2 baths
$2,440
House for rent
Available Aug 24
20h ago
Verified
4 beds
2 baths
$2,905
House for rent
Available Jul 17
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Based on Zumper's July 2026 data, one-bedroom apartments in Highlands, Winter Springs, FL average around $1,340/month, remaining relatively stable year over year.
Based on Zumper's July 2026 data, two-bedroom apartments in Highlands, Winter Springs, FL average approximately $1,610/month, down 3.8% year over year.
Based on Zumper's July 2026 data, three-bedroom apartments in Highlands, Winter Springs, FL average around $2,210/month, up 14.3% year over year.
Based on Zumper's July 2026 data, Highlands apartments in Winter Springs, FL average about $2,030/month across all property types, up 9.5% year over year. August sees the highest rents, running roughly 17% higher than April.
Based on our current listings, apartments in Highlands, Winter Springs, FL average around 1,340 sqft across all unit types, with three-bedrooms running larger at approximately 1,460 sqft.
Based on Zumper's current listings, three-bedroom apartments are the most common rental type in Highlands, Winter Springs, FL, with about 9 listings available monthly.
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.
Based on our current listings, one-bedroom apartments and studios have averaged about 0 listings per month in Highlands, Winter Springs, FL, while two-bedrooms see approximately 3 listings 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 | , , |
| 🧦In-unit laundry | |
| 🍽With dishwasher | |
| 🏠With photos |