Jackie O'Leary Real Estate Agent - FANNIE HILLMAN & ASSOCIATES

2051 Dyan Way, Maitland, FL For Sale $875,000 - co-listed by Jackie O'Leary — For Sale $875,000 • Co-Listing Agent

Jackie O'Leary listing agent for 4720 Gardenbrook Ln, Orlando, FL - sold for $310,000 — Sold $310,000

125 E Faith Terrace, Maitland, FL For Rent $2,200/month - listed by Jackie O'Leary — For Rent $2,200/month

Jackie O'Leary buyer's agent for 791 Windwillow Cir, Winter Springs, FL - sold for $605,000 — Sold $605,000

1351 Merrydale Way, Winter Park, FL For Rent $2,875/month - listed by Jackie O'Leary — For Rent $2,875/month

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	2
Total Value	$704,990
Average Sale Price	$352,495
Price Range	$310K - $395K

Seller Deals
Total Deals	5
Total Value	$1,681,990
Average Sale Price	$336,398
Price Range	$260K - $422K

Buyer Deals
Total Deals	1
Total Value	$605,000
Average Sale Price	$605,000

Seller Deals
Total Deals	10
Total Value	$5,039,490
Average Sale Price	$503,949
Price Range	$260K - $1.6M

Buyer Deals
Total Deals	5
Total Value	$3,939,900
Average Sale Price	$787,980
Price Range	$605K - $1.1M

5 Year View

Neighborhoods Jackie is Experienced In

Williamsburg

2 Sales
College Park

1 Sale
Audubon Park

1 Sale

Jackie's Active Listings

Co-Listing Agent

$875,000
- 5 Beds
- 4 Baths
- 3,136 Sq Ft
2051 Dyan Way

Maitland, FL
Located on quiet cul de sac, this one-story 5 bedroom/4 bath, 3,136 sq ft ranch-style home is a short walk to A-rated Dommerich Elementary and Maitland Middle schools. This home sits on .29 of an acre that backs up to the preserved conservation. Functional floor plan with separate formal living and dining rooms, perfect for entertaining. Eat-in kitchen opens to the cozy family room anchored by

Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

$2,200 per month
- 3 Beds
- 2 Baths
- 1,696 Sq Ft
125 E Faith Terrace

Maitland, FL
Spacious 3 bed, 2 bath home in Maitland! Super Clean & Ready to Go! Split Bedroom Plan, Open kitchen to family room, Laminate Floors throughout. Screen Porch and 2 Car Garage - Location is close to everything. Quiet dead-end street with no thru traffic. Lawncare included in rent. Call for your showing today.

Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

$2,875 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

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 $305K
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 $388K
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
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 $558K
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 $550K
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 $420K
Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

Other Experience

First Time Homebuyers, Investments, Luxury Homes, Property Management, Foreclosures

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