The Highlands
An established, amenity-rich community with 50 years of character and strong family appeal.
Live the MaxLife.
$325K
Median Price
$150K – $520K
1,400
Homes
$33–$404
Monthly HOA
1974
Established
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Background
A brief history
The Highlands was established in 1974 as a master-planned residential community in western Winter Springs. Over the past 50 years, it has grown to encompass more than 1,400 residential units, making it one of the largest and most established neighborhoods in the area. The majority of homes were built between 1972 and 1985, creating a community with deep roots and a strong sense of neighborhood character. The community was designed with families in mind, incorporating extensive recreational amenities and a commitment to quality-of-life features that have attracted generations of homeowners.
The feel
What it's like to live here
The Highlands is defined by mature, tree-lined streets and a genuine sense of community. The neighborhood blends established single-family home charm with the convenience of condos and townhomes, making it accessible to a wide range of buyers. The presence of Highlands Elementary School, championship-caliber recreational facilities, and well-maintained common areas creates a family-oriented atmosphere without the premium pricing of newer developments. Residents appreciate the balance of affordability, amenities, and proximity to SR 434 and Highway 17.
The community's longevity has fostered strong homeowner engagement and an active HOA that maintains high standards for common areas, roads, and recreation facilities. Walking trails, parks with picnic areas, and the Junior Olympic swimming pool give the neighborhood a resort-like feel that appeals to both active families and retirees. The diversity of housing types—single-family homes, condos, and townhomes—means neighbors span different life stages and backgrounds, contributing to the neighborhood's welcoming character.
The details
What to expect
Architecture & Homes
The Highlands features primarily single-family homes built between 1972 and 1985, with many at 1,500–2,500 square feet. You'll also find well-maintained condos and townhomes at lower price points. Most homes are traditional Florida design—brick, stucco, or wood siding with mature landscaping. Many original owners have made upgrades over the years, and the neighborhood has good bones. Don't expect new construction, but expect solid, livable homes in a well-established setting.
Amenities & Lifestyle
The Highlands boasts a championship-quality community center and recreational complex. Highlights include a Junior Olympic-size swimming pool, tennis and pickleball courts, basketball and volleyball facilities, shuffleboard, covered pavilions with BBQ areas, playgrounds throughout the community, and nature walking and jogging trails. The HOA fee (typically $33–$404 for single-family homes) covers maintenance of all these facilities plus common area roads, trash, pest control, cable TV, internet, and property insurance. It's an all-inclusive value.
Schools
Highlands Elementary School (grades PK–5, 528 students) is the primary school and consistently outperforms Seminole County and Florida state averages in math and reading. The school offers a Gifted & Talented program and carries a B+ rating from Niche. It's located at 1600 Shepard Road, within easy distance of the community. The school's strength is a major draw for families considering The Highlands.
Location & Access
The Highlands is conveniently located off SR 434 east of Highway 17 in western Winter Springs, Seminole County. You're minutes from shopping, dining, and services along SR 434, yet the neighborhood feels tucked away and residential. The location offers good access to downtown Winter Springs, neighboring Oviedo and Longwood, and I-4 via Highway 17. For my clients, it's an ideal position—close enough to everything but far enough to feel like home.
Community
Amenities
- Junior Olympic-size swimming pool
- Tennis courts
- Pickleball courts
- Basketball court
- Volleyball court
- Shuffleboard
- Community center and clubhouse
- Nature walking and jogging trails
- Covered picnic pavilions with BBQ
- Playgrounds throughout community
- Well-maintained common area roads
- Professional landscaping and grounds maintenance
- Community park with seating areas
Know Before You Buy
HOA rules worth knowing
- Dues cover all amenity maintenance, roads, pool, trash, pest control, cable/internet, and property insurance
- Active homeowner association with strong community engagement
- Strict maintenance standards for common areas and exterior appearances
- Professional property management oversight
- Regular reserve fund contributions for long-term facility improvements
- Community rules designed to maintain property values and neighborhood character
Market Commentary
What the market is doing
The Highlands represents excellent value in the Winter Springs market. At a median price of $325,000 and price-per-square-foot averaging $170, you're getting into an established community with proven, long-term stability at a price point well below newer developments. The 48 homes that sold in the past 12 months averaged $285,874, showing consistent demand and healthy turnover. I see strong buyer interest here because families want the combination of good schools, solid amenities, transparent HOA fees, and affordability. The 50-year track record speaks for itself—this is a neighborhood that works.
Active MLS Inventory
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Homes available in The Highlands
5 homes currently listed in The Highlands.
$15,000 /mo
4653 Hadfield Dr
Sarasota, FL 34235
4 bd · 5 ba · 3,674 sqft
The Highlands
MLS ID #A4619916
Listing provided by Stellar MLS
$774,500
4305 Highland Oaks Cir
Sarasota, FL 34235
3 bd · 3 ba · 2,612 sqft
The Highlands
This property is under contract. Contact us for backup offer opportunities.
MLS ID #A4676006
Listing provided by Stellar MLS
$614,000
16603 Diplomat Dr
Spring Hill, FL 34610
5 bd · 3 ba · 2,966 sqft
The Highlands
This property is under contract. Contact us for backup offer opportunities.
MLS ID #W7879592
Listing provided by Stellar MLS
$489,900
17820 Monteverde Dr
Spring Hill, FL 34610
3 bd · 2 ba · 1,603 sqft
The Highlands
MLS ID #TB8513469
Listing provided by Stellar MLS
$500,000
16402 Fringe Tree Dr
Spring Hill, FL 34610
3 bd · 3 ba · 1,943 sqft
The Highlands
MLS ID #TB8482716
Listing provided by Stellar MLS
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Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Based on information submitted to the MLS GRID as of June 13, 2026. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA