Woods Jessamine

The Lifestyle

Highly established, luxury lakeside lifestyle nestled within the prestigious city limits of Winter Park. The neighborhood boasts a hyper-dense, historic tree canopy with century-old live oaks draped in Spanish moss and towering cypress trees framing pristine residential lanes along Lake Jessamine. Internal walkability is exceptional, showcasing wide, brick-paved neighborhood paths and secure sidewalks that flow directly to private boat launches and shared lakefront common spaces. Local safety reputation is peerless, maintaining an ultra-quiet, secure, and low-traffic environment that appeals heavily to affluent professionals and generational Winter Park families. Driving logistics are optimized, providing immediate access to Fairbanks Avenue and Interstate 4, allowing for an effortless 10-to-15-minute commute to downtown Orlando or the Park Avenue shopping district. The community footprint exudes a historic, highly refined domestic elegance driven by deep estate lot setbacks, immense pride of ownership, and strict municipal preservation standards.

The Real Estate

Year Founded:

1965

Architectural Style:

  • Classic Floridian
  • Custom Colonial
  • French Provincial
  • Traditional

Home Types:

  • Custom (Exclusively custom-built architectural masterpieces and luxury historical updates on estate-sized parcels).

Average Lot Size:

0.42

Price Range Est.

Low

$750,000

High

$3,450,000

Community Amenities

  • Private lake access
  • community boat ramp
  • fishing pier
  • park pavilion
  • scenic oak hammocks

H.O.A. Fee Range:

$0/None

 Neighborhood :

Schools

Elementary 

Killarney Elementary

Middle

Glenridge Middle

High

Winter Park High

Private

The Parke House Academy

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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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[Woods Jessamine] 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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