Hills

The Lifestyle

Highly established, luxury residential estate footprint synonymous with exceptional private living along the rolling western boundary corridors of the historic Winter Park core. The tract showcases a highly mature, hyper-dense tree canopy featuring ancient live oaks draped in Spanish moss, towering palms, and native foliage that frame expansive properties. Internal walkability is safe and highly private, restricted to winding, low-traffic estate lanes and corridors that experience virtually zero external cut-through transit. Local safety reputation is superb, maintained by an established, long-term homeowner dynamic and heavy personal spatial privacy parameters. Driving logistics are highly convenient, giving residents quick access to Orlando Avenue (US 17-92) and Interstate 4 for a streamlined commute into downtown Orlando or Rollins College. The community atmosphere is exceptionally quiet, refined, and prestigious, serving as an elite residential haven for affluent households seeking deep lot setbacks and natural serenity.

The Real Estate

Year Founded:

1974

Architectural Style:

  • Custom Ranch Masterpieces
  • Executive Contemporary
  • Mediterranean Estate
  • Traditional

Home Types:

  • Custom (Entirely custom-built residential enclave featuring individualized architecture on oversized tracts).

Average Lot Size:

0.38

Price Range Est.

Low

$595,000

High

$1,450,000

Community Amenities

  • Private park area
  • open green spaces
  • scenic neighborhood overlook zones
  • perimeter green space buffers

H.O.A. Fee Range:

$0/None

 Neighborhood :

Schools

Elementary 

Killarney Elementary

Middle

Glenridge Middle

High

Winter Park High

Private

The Geneva School

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Market Analysis

We can provide you with a complimentary comprehensive analysis of this community or a specific house. The CMA contains information like average sales price, price per sq ft, days on market, and list price versus final sales price. etc.

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Click on quadrant, price range or community to learn more and see which homes are for sale.

Elite

$1M+

Executive

$750k+

Professional

$500k+

Discovery

-$500k

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[Hills] Master: $0/None

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Please click link below to download my mobile MLS app:  If requested, here is the access  code : D274189C.

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