2559 Gresham Dr, Orlando, FL 32807
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Property image
OFF MARKET

2559 Gresham Dr
Orlando, FL 32807

  • 4 Beds
  • 2 Baths
  • 1,575 sqft

$369,700

Trulia Estimate
as of Aug 12, 2026
Est. Refi. Payment $2,610/mo*
Refinance Your Home

$369,700

Trulia Estimate
as of Aug 12, 2026
Est. Refi. Payment $2,610/mo*
Refinance Your Home
4 Beds
2 Baths
1,575 sqft

Home Value

Trulia Estimate
$370K
Since last month
Increased$2K (+0.6%)
Since last year
Increased$9K (+2.4%)
Since last sale
Increased$179K (+94.1%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +110% in the last 10 years
MonthEstimated value
2026
August 2026$370K
July 2026$368K
June 2026$368K
May 2026$366K
April 2026$368K
March 2026$361K
February 2026$359K
January 2026$352K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
7468 Faculty Dr, Orlando, FL
0.12
Single-Family Home
$290,000
12/02/25
4
2
1,525
2839 ANTIOCH WAY, Orlando, FL
0.15
Single-Family Home
$360,000
07/17/26
3
2
1,459
2806 MOSS GROVE BOULEVARD, Orlando, FL
0.17
Single-Family Home
$372,000
07/30/26
3
2
1,272
2747 ROSE MOSS LANE, Orlando, FL
0.23
Single-Family Home
$379,000
10/30/25
3
2
1,486
2744 MIDDLE STREET, Orlando, FL
0.21
Single-Family Home
$375,000
04/30/26
3
2
1,379
2483 BECKY SUE DRIVE, Orlando, FL
0.32
Single-Family Home
$347,000
04/30/26
4
2
1,709
2831 ANTIOCH WAY, Orlando, FL
0.13
Single-Family Home
$421,500
06/26/26
3
2
1,678
7649 STRATFORD BOULEVARD, Orlando, FL
0.29
Single-Family Home
$289,900
03/23/26
3
2
1,375
2620 BLUEBONNET STREET, Orlando, FL
0.16
Single-Family Home
$390,000
01/02/26
3
2
1,848
2343 PEAR TREE COURT, Orlando, FL
0.27
Single-Family Home
$285,000
11/25/25
3
2
1,174

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
7438 WAYLAND BOULEVARD, Orlando, FL 32807
0.05
$414,600
3
2
1,680
Off Market
7427 FORDHAM COURT, Orlando, FL 32807
0.09
$400,000
4
2
1,695
For Sale
2806 MOSS GROVE BOULEVARD, Orlando, FL 32807
0.17
$372,000
3
2
1,272
Recently Sold
2733 MIDDLE STREET, Orlando, FL 32807
0.17
$395,000
3
2
1,204
For Sale
2831 ANTIOCH WAY, Orlando, FL 32807
0.13
$421,500
3
2
1,678
Recently Sold
3000 GEORGE MASON AVENUE #1, Winter Park, FL 32792
0.18
$89,100
2
2.5
1,108
Off Market
3002 GEORGE MASON AVENUE #3, Winter Park, FL 32792
0.18
$89,750
2
2.5
1,085
Recently Sold
2839 ANTIOCH WAY, Orlando, FL 32807
0.15
$360,000
3
2
1,459
Recently Sold
3015 AARON BURR AVENUE #7, Winter Park, FL 32792
0.19
$121,400
2
2
1,088
Off Market
7288 DANIEL WEBSTER DRIVE #5, Winter Park, FL 32792
0.20
$130,500
2
2.5
1,230
Off Market
3021 AARON BURR AVENUE #3, Winter Park, FL 32792
0.19
$140,000
2
2.5
1,090
For Sale
2744 MIDDLE STREET, Orlando, FL 32807
0.21
$375,000
3
2
1,379
Recently Sold

Local Information

  • Map ViewExplore the area around 2559 Gresham Dr.
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1972
Living Area
1,575 sqft
Price/Sqft
$235
Parking
Garage

About this House

NO HOA!!!!!!!!!!!!!!!!!!!Great Opportunity to own a beautiful 4 bedroom, 2 bathroom home in Winter Park most desirable High School District, This well maintain home offers a Split floor plan, carpet throughout the house, new architectural shingle roof in 2005, wetlands adjacent rear property and fire station on adjoining rear property, this home also offers a huge screened porch and a big fence back yard. Great location close to Full Sail University, Winter Park's Park Avenue, Rollins College, UCF, 408 expressway, I4, 417 and minutes away from downtown Orlando and Orlando international Airport.
2559 Gresham Dr, Orlando, FL 32807 is a 4 bedroom, 2 bathroom, 1,575 sqft single-family home built in 1972. It last sold for $190,575 on Jan 6, 2017. It is currently off market. The Trulia Estimate is $369,700, with a rent estimate of $2,531/month.

Home Details for 2559 Gresham Dr

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1Floors: Carpet, Linoleum Vinyl
Interior Details
Types of Rooms: Dining RoomCeiling Fan
Appliances & Utilities
Cable ReadyDishwasherDryerMicrowaveRefrigerator

Exterior Features

Exterior Home Features
Roof: CompositionDeckPatioPorch
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1972Year Updated: 1979
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 8607 sqft

Price and Tax history

DateEventPrice
Jan 6, 2017
Source: N/A
Sold
$190,575
Nov 17, 2016
Source: Agent Provided
Pending
$199,000
Nov 9, 2016
Source: Agent Provided
Listed For Sale
$199,000

Market trends in Orlando

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$381K
$9.25KMoM
Sale-to-List Price
98.0%
0.1%MoM
Price per sq ft
$232
$1MoM
Available listings
4195
15MoM
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Around this home

What Locals Say about Orlando

At least 8172 Trulia users voted on each feature.

  • 84 % Say it's dog friendly

  • 84 % Say there are sidewalks

  • 80 % Say car is needed

  • 72 % Say parking is easy

  • 69 % Say there's holiday spirit

  • 66 % Say streets are well-lit

  • 63 % Say yards are well-kept

  • 63 % Say kids play outside

  • 61 % Say it's quiet

  • 58 % Say it's walkable to grocery stores

  • 57 % Say people would walk alone at night

  • 53 % Say it's walkable to restaurants

  • 49 % Say they plan to stay for at least 5 years

  • 45 % Say neighbors are friendly

  • 43 % Say there's wildlife

  • 28 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Isa Tay
    "This is a very dog friendly neighborhood. "
    0
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  • Susan
    "Very dog-friendly"
    0
    Flag
  • Hector Rentas
    "Like every other commute in Orlando congested during school seasons and tolerable when not"
    0
    Flag
  • Cinthya Dantas-LeBlanc
    "The house is at kingswood manor. The neighborhood is very safe and quiet. There are lots of families, children playing around, people walking their dogs and exercising. They also have a nice park with a playground, swimming pool, tennis and basketball. "
    1
    Flag
  • Claritzamartinezc
    "Is a fair place to live, pretty well preserved for families. Near store and restaurants, shopping malls within 15 if major theme parks."
    0
    Flag
  • Nettiayant891
    "The neighborhood has its own parks, playgrounds for children basketball courts for young adults. Pools for kids,adults and toddlers. Tennis court,volleyball and track for walkers."
    0
    Flag
  • Maria Beaman
    "I drive everywhere because it doesn’t look like public transportation is available in the area. The neighborhood might have public transportation."
    0
    Flag
  • Jacklyn
    "The schools in the area have football games on Fridays. The elementary, middle and high school are in good proximity to each other, which makes it easier to get all the kids to school and practice. "
    0
    Flag
  • Cmwhiting1
    "I work remotely. When I did commute I worked downtown, but I also lived very close to downtown. And being an Orlando native, I took a lot of back roads. So I’ve fortunately never had a problem with commuting to work in Orlando. "
    0
    Flag
  • Bestmentor
    "If you live in the city, it’s more of a downtown field, but it is not really kid friendly until you get on the outskirts of the actual downtown area. But the surrounding areas around to the north and the east is the favorite areas of mine."
    0
    Flag
  • Luscious305
    "Dog owners walk there dogs but they do not clean up after them. People do own a lot of dogs around here"
    0
    Flag
  • Melibee22
    "Very human and pet family friendly!!! Great for kids and young families as well as retired! Pretty quiet! "
    0
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  • 4czmnzsw88
    "The community has movie nigths. Haloween is very interactive and friendly. I love this area. Near by supermarket, hospital, social events."
    0
    Flag
  • 4czmnzsw88
    "Halloween is nice here. The are outside movies at the community center. Community center has free teen program. "
    0
    Flag
  • Jsharon548
    "I’ve lived in this area for 5 years and the people in the neighborhood are very friendly and very helpful to one another I enjoy been in this neighborhood "
    0
    Flag
  • Charles Richard
    "Art Festivals are unique to this are and outdoor bistros and cafes. Sunrail train transportation is available and can transport you from one place to another easily."
    0
    Flag
  • Natividad Marinez
    "Mixed ethnicities equals great community love living here, family oriented, great schools, pet friendly"
    0
    Flag
  • Ayanac01
    "The Schools are pretty good. The shopping centers, restaurants are all good and really nice places in the area"
    0
    Flag
  • Seth Daniels
    "Lots of neighborhood streets to walk. Great dog park in Baldwin park. Many many dog owners. Some of them actually good dog owners. "
    0
    Flag
  • 6fdh87psq7
    "The country club host several events throughout the year. The local clubs have events as well. Dining is nice too"
    0
    Flag
  • Trulia User
    "There are really nice neighborhoods around this area. Some of the schools are nice. A lot of the shopping centers are well kept and maintained."
    0
    Flag
  • Nickwilson1997.nw
    "Collaboration between everyone and them cleaning up and getting along. There’s always activities to get involved"
    0
    Flag
  • Dmontgomery_4
    "Easy on and off to I4 and 408, 5 minutes to downtown, 3 parks with in walking distance close to everything"
    0
    Flag
  • Charlotte Monique Perry-hylick
    "Everyone knows each other and we make sure we stay together on what’s going on in the neighborhood ..we keep each other informed with all that’s happening "
    2
    Flag
  • Aj2636
    "I enjoy attending Orlando Magic Games at the Kia Center. Lake Eola serves as a gathering center for all age groups."
    0
    Flag
  • Charlotte Monique Perry-hylick
    "The neighbors are great and they make sure the neighborhood stays together and well maintained when it comes to everything "
    1
    Flag
  • Elsiealfonso
    "Many people walks their dogs, and there are devices with plastic bags to help people to dispose of their dogs poopoo."
    0
    Flag
  • Yigitorer
    "Good safe nice neighborhood no crime clean area highly recommended close to all major rods and shopping plaza and Waterford lakes "
    0
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  • Deyonca King
    "I love this community and the area is mostly working class people who want to enjoy their personal space and homes."
    0
    Flag
  • Trulia User
    "20-30 minutes to get anymore. Traffic worsening especially on Narcoossee. A lot of new development so exciting place to live. "
    0
    Flag
  • Milanee Soto
    "need to clean up after themselves area needs to stay clean and quiet. Owners will like the dog park in the communities easy access "
    0
    Flag
  • Matt B.
    "Been living in Meadow Woods for the last year, I can say that I feel very safe, everything is within driving distance, and very respectable. Friendly neighborhoods, friendly people, and access to stores. "
    3
    Flag
  • Milanee Soto
    "safety is a key factor in living in this area, many place to go to that is within walking distance.. could use more children parks near by"
    0
    Flag
  • Milanee Soto
    "beautiful and comfortable. Great community and easy access. outlets, malls, grocery shopping, hospitals and local police "
    0
    Flag
  • torry huneycutt
    "This place is pretty nice. Traffic gets bad during rush hours. There is a good bit of police activity here as well. "
    0
    Flag
  • K Brack
    "In my part of Orlando which is Sanford has a good school system. The area has plenty of malls and stores. There are trails to walk and bike all over. "
    0
    Flag
  • Lindsaysapienza1
    "I work from home so no commuting necessary. However, there is always traffic on the main road narcooseee when driving around town "
    0
    Flag
  • Mustangzilla
    "Some roads go from having a sidewalk to nothing completely and you are stuck walking in the street. "
    0
    Flag
  • Marcey Carter
    "My business and neighborhood it seems like the neighborhood is clean and neighbors are poorly friendly. Nothing crime going on in the area."
    1
    Flag
  • Maritza Martnez
    "I have lived in this area since 2020 and it is a safe area, it can get a bit loud, but it’s a safe area. I like that is central to everything even a hospital nearby. "
    0
    Flag

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Homes for sale near 2559 Gresham Dr

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Off Market Homes Near 2559 Gresham Dr

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Frequently asked questions about 2559 Gresham Dr

  • What is 2559 Gresham Dr estimated to be worth?
    Trulia's estimated value for 2559 Gresham Dr in Orlando, FL is $369,700.
  • What is the price history for 2559 Gresham Dr?
    2559 Gresham Dr in Orlando, FL last sold for $190,575 in January 2017.
  • Is Orlando a buyer's or seller's market?
    Orlando is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Orlando?
    The median sale price in Orlando is $381K. That is up $9.25K from the prior month.
  • Does 2559 Gresham Dr have air conditioning?
    Yes, 2559 Gresham Dr in Orlando, FL has air conditioning.
  • Does 2559 Gresham Dr have laundry facilities?
    Yes, 2559 Gresham Dr in Orlando, FL has laundry facilities.