Preston Square
Historic Savannah-inspired neighborhood with central plaza gathering space.
Live the MaxLife.
$1.1M
Median Price
$600K – $2.1M
143
Homes
$180–$350
Monthly HOA
2007
Established
Windermere Elementary or Sunset Park Elementary (zoning dependent)
School Zone
Background
A brief history
Preston Square was developed in 2007 as a mixed-use community combining 68 townhomes and 75 single-family detached homes on the west side of Winter Garden Vineland Road. The developer drew inspiration from historic Savannah, Georgia neighborhoods, placing the community green space and amenities at the heart of the development rather than at a distant clubhouse. This gave the community an unusual design element for Central Florida: many homes have rear-facing driveways and garages, allowing front porches and green space facing the central plaza. Build-out was completed by 2010. The community maintains an active HOA and attracts both first-time homebuyers and downsizers seeking walkable neighborhood living.
The feel
What it's like to live here
Preston Square's defining characteristic is its Savannah-inspired central plaza — an open green space surrounded by homes with front porches. Most residents park in rear driveways, which is unusual for Central Florida but creates an exceptionally walkable, porches-facing-neighbors environment. Townhomes range 1,079–2,158 square feet; single-family homes range 1,593–3,446 square feet. Lot sizes are modest (typically 0.25–0.45 acre), but the community amenity center with pool, basketball court, playground, and large open lawn makes up for smaller individual lots. Trees have matured significantly since 2007; the neighborhood now has visible canopy. It's the kind of place where residents actually know their neighbors — kids walk to the pool, families gather in the plaza on weekends.
The details
What to expect
Architecture & Lots
Mix of townhomes (1,079–2,158 sq ft) and single-family homes (1,593–3,446 sq ft). Modest lot sizes 0.25–0.45 acre compensated by central plaza. Most homes have rear driveway/garage and front-facing porches — unusual and effective for walkability. Traditional architecture with pitched roofs, front porches, and varied exterior materials.
Central Plaza & Walkability
The community's heart is an open plaza surrounded by homes with front porches. Central amenity building with pool, basketball court, children's playground, and large lawn gathering space. Residents genuinely walk to amenities and socialize in the plaza. Tree canopy has matured significantly; streets are shaded.
Amenities & Community Life
Central court area with large pool, basketball court, ample green space, children's playground, and community pavilion. The layout encourages walking — residents walk to pool, playground, and neighborhood cafes nearby. No golf course or high-end resort amenities, but strong neighborhood social life.
HOA Rules & Fees
Monthly HOA $180–$350 depending on home type and section. Architectural review required for exterior changes. Fencing restricted to preserve sightlines toward plaza. Parking standards enforced (front garages hidden in rear). Community pool maintenance and landscaping covered by HOA. Short-term rentals restricted; 30-day minimum lease.
Location & Access
Located on west side of Winter Garden Vineland Road, nearly opposite Windstone community. Eleven miles southwest of downtown Orlando, just north of Walt Disney World. Good access to Route 535 and nearby shopping. Quick drive to Windermere Prep and other schools.
Community
Amenities
- Central community plaza with open green space
- Community pool and splash area
- Basketball court
- Children's playground with age-separated equipment
- Community pavilion for gatherings
- Mature tree canopy throughout
- Walking-friendly streets and plaza
Know Before You Buy
HOA rules worth knowing
- Monthly HOA $180–$350 depending on home type
- Architectural review for exterior changes
- Fencing restricted to preserve plaza sightlines
- Rear driveway/garage design enforced (front porches required)
- Landscape maintenance standards
- Short-term rentals prohibited or restricted; 30-day minimum
- Community pool maintained by HOA
Education
School assignments
- Windermere Elementary or Sunset Park Elementary (zoning dependent)
- Bridgewater Middle or Gotha Middle (zoning dependent)
- Windermere High or Olympia High (zoning dependent)
- Windermere Prep (private, under 10 minutes)
School zone assignments change. Verify with Orange County Public Schools before purchase.
Market Commentary
What the market is doing
Townhomes trade in the $600K–$900K range depending on square footage and finish. Single-family homes trade $900K–$1.5M for original construction, with renovated or rebuilt homes pushing to $2M. Recent renovations have included kitchen updates, new HVAC systems, and master bath upgrades. Days-on-market average 25–40 days for homes priced to comps. The community appeals to young families priced out of neighborhoods like Keene's Pointe, retirees downsizing from larger estates, and empty-nesters valuing walkability over square footage.
Active MLS Inventory
Search homes in Preston Square
Live MLS search for Preston Square is coming online shortly.
In the meantime, get notified when a home in Preston Square hits the market — VIP list members see new Preston Square inventory 48 hours before it appears on Zillow.
Get Preston Square AlertsRecent Work
Recent sales in Windermere
Representative closings across Windermere. Our Preston Square off-market pipeline is larger than what's shown here.
No recent listings shown yet for Preston Square. Join the VIP list to see upcoming inventory first.
Also Worth Seeing
Related communities
Windermere
Lakes of Windermere
Master-planned family community with Victorian charm and lake-view living.
$850K – $2.9M · 606 homes
Explore Lakes of Windermere →
Windermere
Glenmuir
Family-friendly gated enclave with multiple ponds and resort-style amenities.
$750K – $2.8M · 230 homes
Explore Glenmuir →
Windermere
Waterstone
Tuscan and Mediterranean luxury with 24-hour security and Windermere Prep access.
$1.5M – $4.6M · 120 homes
Explore Waterstone →
Windermere
Cypress Woods
A Windermere gated community under mature cypress canopy off Chase Road.
$1M – $2.5M · 110 homes
Explore Cypress Woods →
Want Preston Square homes first?
Hand-picked Preston Square matches — 48 hours before MLS. Two to three per month.
Information on this page is compiled from public records, MLS data, community associations, and broker observation. Price ranges, HOA fees, school assignments, and community amenities change — verify all details with MaxLife Realty and the relevant community association before making a purchase decision. Ryan Solberg, Broker, License #BK3354351. MaxLife Realty, 321.373.3536.