Jackie O'Leary

Winter Park FL

FANNIE HILLMAN & ASSOCIATES

15 Closed Sales

$9M Total Value

$260K - $1.6M Price Range

$598.6K Average Price

Prior 5 years

About Jackie

407.718.0887 is my cell number

Home Types: House, Condo

Years of Experience: 21

Transaction History

1 Year
2 Year
5 Year

Seller Deals

Total Deals

Total Value

$2,229,490

Average Sale Price

$371,582

Price Range

$260K - $548K

Buyer Deals

Total Deals

Total Value

$605,000

Average Sale Price

$605,000

Seller Deals

Total Deals

Total Value

$5,039,490

Average Sale Price

$503,949

Price Range

$260K - $1.6M

Buyer Deals

Total Deals

Total Value

$3,939,900

Average Sale Price

$787,980

Price Range

$605K - $1.1M

5 Year View

Neighborhoods Jackie is Experienced In

Jackie's Active Listings

$3,150 per month
- 3 Beds
- 2.5 Baths
- 1,755 Sq Ft
1351 Merrydale Way

Winter Park, FL
Fantastic, Modern townhome WITH 3 beds & 2.5 baths. Hawk's Crest is a gated community in Winter Park. This home is has a very spacious open floor plan with a water view! The kitchen has granite countertops and is fully equipped with stainless steel Whirlpool appliances; oven, stove, microwave, refrigerator, dishwasher, and garbage disposal. The kitchen area also has a large pantry! This energy

Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

$1,975 per month
- 3 Beds
- 2 Baths
- 1,241 Sq Ft
932 Robinhood Ct

Maitland, FL
Great duplex in Maitland! Freshly painted, Newer stainless steel kitchen appliances. Tile throughout, screened in porch, on quiet cul-de-sac. Very near Shopping, Restaurants, SunRail boarding literally down the street. 3 Bedrooms, 2 Baths, 2 Car Garage. Lawncare included in rent. Sorry NO Pets.

Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

$3,475 per month
- 3 Beds
- 2 Baths
- 1,670 Sq Ft
1850 Whitehall Dr

Winter Park, FL
This is a wonderful pool home located in the sought after neighborhood of Kenilworth Shores in Winter Park. It features 3 bedrooms & 2 baths with an open floor plan. Family room/dining room combo, a wonderful Florida room overlooking the backyard & pool area. Enjoy the weekends lounging around the black bottom pool and the lush landscape surrounding the backyard. ALL UTILITIES included! The

Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

Recently Sold

$310,000 Sold Dec 4, 2025
- 2 Beds
- 2 Baths
- 1,070 Sq Ft
4720 Gardenbrook Ln

Orlando, FL
- $290/SF
- 18 Days On Market
- Current Est. Value $308K
Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

$394,990 Sold Nov 21, 2025
- 3 Beds
- 2 Baths
- 1,519 Sq Ft
5618 Arnold Zlotoff Dr

Orlando, FL
- 5% Below List
- $260/SF
- 83 Days On Market
- Current Est. Value $393K
Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

$260,000 Sold Jun 6, 2025
- 2 Beds
- 1 Bath
- 710 Sq Ft
151 N Orlando Ave

Unit 115

Winter Park, FL
- 9% Below List
- $366/SF
- 28 Days On Market
- Current Est. Value $289K
Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

$422,000 Sold Mar 31, 2025
- 3 Beds
- 1.5 Baths
- 1,436 Sq Ft
2000 N Westmoreland Dr

Orlando, FL
- 20% Below List
- $294/SF
- 103 Days On Market
Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

$547,500 Sold Apr 30, 2024
- 2 Beds
- 2 Baths
- 1,092 Sq Ft
112 Tangelo Ct

Maitland, FL
- 4% Below List
- $501/SF
- 10 Days On Market
- Current Est. Value $551K
Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

$525,000 Sold May 12, 2022
- 3 Beds
- 2.5 Baths
- 1,641 Sq Ft
1126 Washington Ave

Unit 9A

Winter Park, FL
- $320/SF
- 17 Days On Market
- Current Est. Value $521K
Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

$1,560,000 Sold Apr 14, 2022
- 3 Beds
- 3.5 Baths
- 3,112 Sq Ft
101 S New York Ave

Unit 312

Winter Park, FL
- 2% Below List
- $501/SF
- 42 Days On Market
- Current Est. Value $1M
Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

$380,000 Sold Mar 7, 2022
- 2 Beds
- 1 Bath
- 876 Sq Ft
1500 Bennett Rd

Orlando, FL
- $434/SF
- 9 Days On Market
- Current Est. Value $419K
Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

Other Experience

First Time Home Buyers, Foreclosures, Investments, Luxury Homes, Property Management

Agent License: Florida 3144118

Jackie O'Leary

(888) 861-5907

Homes for Sale by City

Jackie O'Leary

About Jackie

Transaction History

Seller Deals

Seller Deals

Buyer Deals

Seller Deals

Buyer Deals

Production Over Time

5 Year View

Neighborhoods Jackie is Experienced In

Jackie's Listings and Deals

Jackie's Active Listings

Recently Sold

Other Experience