237 James Dr, Winter Garden, FL 34787
OFF MARKET

$392,200

Trulia Estimate
  • 3 Beds
  • 1 Bath
  • 1,254 sqft

237 James Dr, Winter Garden, FL 34787

Est. Refi. Payment $2,798/mo*
Refinance Your Home
Currently Off Market - Sold Nov 2, 2012 for $118,000

Home Value

Trulia Estimate
$392K
Since last month
Decreased$4K (-1.1%)
Since last year
Decreased$8K (-1.9%)
Since last sale
Increased$275K (+232.6%)
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 +138% in the last 10 years
MonthEstimated value
2026
August 2026$393K
August 2026$392K
July 2026$397K
June 2026$392K
May 2026$393K
April 2026$395K
March 2026$392K
February 2026$389K
January 2026$382K
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
236 DONALD DRIVE, Winter Garden, FL
0.16
Single-Family Home
$450,000
06/29/26
2
1
1,080
275 VIRGINIA DRIVE, Winter Garden, FL
0.08
Single-Family Home
$465,000
12/02/25
4
2.5
2,004
236 E NEWELL STREET, Winter Garden, FL
0.11
Single-Family Home
$543,000
03/10/26
2
2
1,659
119 Charlotte St, Winter Garden, FL
0.61
Single-Family Home
$112,000
06/29/26
2
1
816
308 Florida Avenue, Winter Garden, FL
0.55
Single-Family Home
$315,000
02/20/26
3
2
1,050
423 N MAIN STREET, Winter Garden, FL
0.31
Single-Family Home
$655,000
09/26/25
3
2
1,668
341 E LAFAYETTE STREET, Winter Garden, FL
0.77
Single-Family Home
$162,500
07/31/26
2
1
1,106
338 Pennsylvania Ave, Winter Garden, FL
0.64
Single-Family Home
$295,000
06/05/26
4
2
1,343
237 N CENTRAL AVENUE, Winter Garden, FL
0.47
Single-Family Home
$495,000
09/24/25
3
2
1,650
422 CHARLOTTE STREET, Winter Garden, FL
0.73
Single-Family Home
$290,000
04/23/26
3
1
858

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
213 JAMES DRIVE, Winter Garden, FL 34787
0.03
$500,500
3
2
1,500
Off Market
207 JAMES DRIVE, Winter Garden, FL 34787
0.04
$667,700
4
2
1,991
Off Market
133 AGNES STREET, Winter Garden, FL 34787
0.07
$372,400
2
1
1,287
Off Market
200 E NEWELL STREET, Winter Garden, FL 34787
0.09
$450,500
3
2
1,811
Off Market
121 AGNES STREET, Winter Garden, FL 34787
0.08
$1,617,900
4
3.5
2,766
Off Market
236 E NEWELL STREET, Winter Garden, FL 34787
0.11
$543,000
2
2
1,659
Recently Sold
275 VIRGINIA DRIVE, Winter Garden, FL 34787
0.08
$465,000
4
2.5
2,004
Recently Sold
241 N DILLARD STREET, Winter Garden, FL 34787
0.07
$1,499,999
4
3
3,507
For Sale
290 GARY DRIVE, Winter Garden, FL 34787
0.11
$503,900
3
2
1,758
Off Market
234 N DILLARD STREET, Winter Garden, FL 34787
0.10
$1,014,400
4
3
2,184
Off Market
236 DONALD DRIVE, Winter Garden, FL 34787
0.16
$450,000
2
1
1,080
Recently Sold
282 E NEWELL STREET LOT 57, Winter Garden, FL 34787
0.17
$345,000
-
-
-
Recently Sold

Local Information

  • Map ViewExplore the area around 237 James Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1956
Living Area
1,254 sqft
Price/Sqft
$313
Parking
Garage

About this House

Hurry! This Three Bedroom, One Bath Home won't last very long.Surrounded by Huge Oak Trees and Spanish Moss,will remind you of Florida of a By Gone Era, just blocks away from Historic Winter Garden, The West Orange Trail, Public boat dock, and Community Swimming Pool and Park. Location, Location, Location.Hardwood Floors through out,this 1254 heated sq. foot home with one car garage,bonus area covered Lanai, deck and work shed with mature trees and landscaping on this .2381 acre {75' x 138'} with gated back yard. Granite counter tops in kitchen with all appliances including Washer / Dryer in Utility Room. Minutes from CR 50, 408,429 and the Florida Turnpike, The Fowler's Grove Mall and shops and restaurants. New incentive "Up to 3.5% closing cost assistance and up to $500 home warranty credit may be available on this property for buyers! Ask the agent. Eligibility restrictions apply.". Don't miss this affordable opportunity! Selling As-Is with right to inspect. If exact square footage/measurements or HOA data are a concern, home should be independently measured or verified. Purchase this property for as little as 3 percent down! This property is approved for HomePath Mortgage and HomePath Renovation Mortgage Financing. Visit the HomePath website for more information. Brokered And Advertised By: EVISTA RESOURCES Listing Agent: FRANCIS TIFFANY
237 James Dr, Winter Garden, FL 34787 is a 3 bedroom, 1 bathroom, 1,254 sqft single-family home built in 1956. It last sold for $118,000 on Nov 2, 2012. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $392,200, with a rent estimate of $2,412/month.

Home Details for 237 James Dr

Interior Features

Heating & Cooling
Heating: Forced AirCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1
Interior Details
Additional StorageStorageCeiling Fan

Exterior Features

Exterior Home Features
Roof: Shake Shingle
Parking & Garage
GarageParking: Garage

Property Information

Year Built
Year Built: 1956Year Updated: 1966
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 10454 sqft

Price and Tax history

DateEventPrice
Nov 2, 2012
Source: N/A
Sold
$118,000
Sep 15, 2012
Source: Agent Provided
PriceChange
$124,900
Price increased by 0%
Sep 11, 2012
Source: Agent Provided
Listed For Sale
$0
Jun 4, 2007
Source: N/A
Sold
$212,000
Mar 25, 1999
Source: N/A
Sold
$76,800

Market trends in Winter Garden

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$583K
$3.33KMoM
Sale-to-List Price
98.3%
0.2%MoM
Price per sq ft
$254
$3MoM
Available listings
760
4MoM

Around this home

What Locals Say about Winter Garden

At least 513 Trulia users voted on each feature.

  • 92 % Say it's dog friendly

  • 88 % Say there are sidewalks

  • 86 % Say car is needed

  • 83 % Say parking is easy

  • 81 % Say there's holiday spirit

  • 78 % Say kids play outside

  • 76 % Say it's quiet

  • 75 % Say streets are well-lit

  • 74 % Say people would walk alone at night

  • 72 % Say yards are well-kept

  • 61 % Say they plan to stay for at least 5 years

  • 54 % Say neighbors are friendly

  • 54 % Say there's wildlife

  • 50 % Say it's walkable to grocery stores

  • 46 % Say it's walkable to restaurants

  • 43 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • jhp331
    "A rated schools and lots to do for families "
    0
    Flag
  • Trulia User
    "Its great to live this area we have market and restauran near us . We can walk when we want in our neighboorhood. We have parks schools near us …"
    0
    Flag
  • Amanda
    "Great safe area for all ages and diversity. Good schools, lots of shopping, dining, nearby and more coming."
    0
    Flag
  • Ypgs9v7hpd
    "It is a nice area and the schools are nice. It is good area to raise children away from the tourists area and the city ."
    0
    Flag
  • Ypgs9v7hpd
    "The only thing that is unique about this neighborhood is the people that are friendly and the kids get along great. The only downside of living here in Wintergarden is it’s not enough places to go out to eat and it is not enough places for kids to hang out or teenagers to hang out and the closest place for teenagers to hang out is at the Wintergarden Grove area where you have to take off the exit 9, which I think that’s a bit too far for them to hang out when they can remain closer, it would be better if they had a place to hang out within the neighborhood. Also, Price is over here for a living is very high so if you’re not making a decent amount of money, it is expensive even the apartments that are surrounding it. It’s expensive.."
    0
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  • Emilye Chasen
    "Downtown events occur all the time. Christmas, Halloween, 4th of July etc. Santa comes down my street"
    1
    Flag
  • Ypgs9v7hpd
    "I’ve living here for the last 3 yrs. It’s nice area, people are nice. It’s nice area to raise your family there."
    0
    Flag
  • Heather Kotyk
    "I work near the airport and the commute using the turnpike and I4 is about 25-30 minutes. Traffic is usually manageable and continuously is moving "
    0
    Flag
  • Erin
    "There are many families in the neighborhood, a great playground and an A rated school nearby. There’s also a grocery store and pharmacy conveniently within a mile. "
    0
    Flag
  • Maria Rojas
    "Great place to have a family, lots of parks and activities for kids. Amazing schools and the community is very united. Most communities have hoa "
    0
    Flag
  • Rosa Aguilar
    "There’s lots of places, activities, parks, trails to take kids. There’s also lots of churches with daycare and city programs for children to take part in."
    0
    Flag
  • Andres.toro
    "Mostly all good schools. A lot of parks (and a few others upcoming) and services are increasing in availability. "
    0
    Flag
  • Logan Mahalek
    "The historic area of downtown winter garden boasts local shops and restaurants and also hosts a farmers market every weekend. There is also plenty of name brands within 15 minutes "
    0
    Flag
  • Cfbranf3rd
    "I’m don’t have a commute, as I’m retired. I’m in Cypress Reserve, and Avalon Road can be a nightmare at school drop off/pick up times."
    0
    Flag
  • Kelly
    "Beautiful, safe & friendly area. Winter Garden is a great place to raise a family! This is a very active area with tons of activities. Lots of wildlife & opportunities to get in touch with nature. Big, beautiful Florida birds and animals all around. Great restaurants too! "
    0
    Flag
  • Geisha
    "In Winter Garden for the area's of Horizon West, Hamlin, Summerlake, Waterleight, The Grove is amazing is like living in a perfect community bubble completely recomend"
    0
    Flag
  • Catherine Law
    "There is a private lake side park and a bbq area. Dogs poop trash and bags available. Dogs need to be on leash all the time. No many houses are fenced. "
    0
    Flag
  • Vanessaasantini
    "Wonderful , Safe, beatiful, peaceful, very good, clean, good school, nice and bog city Close to supermarket, gas station "
    2
    Flag
  • Aj2636
    "Halloween costume parties for kids. Community Easter egg hunts. Santa Claus visits on a fire truck. Community watch parties for football games. A soccer field, tennis courts, pickleball courts and basketball courts that allow the neighborhood to enjoy each other’s company. During COVID, we had live music performances in the park."
    0
    Flag
  • Cara Conley
    "The area is established and offers. Great amenities within 15 minutes. Clean and safe and welcoming."
    1
    Flag
  • Isaac Peterson
    "Very friendly and helpful neighbors, and the schools are awesome. Very safe "
    2
    Flag
  • Aj2636
    "I’ve lived here for 11 years. It’s close to shopping. The neighborhood feels comfortable with homes far apart from each other. Nice lakes nearby that most neighborhoods have access to. Hospital close-by for emergencies."
    1
    Flag
  • Felton.amanda
    "I lived here for 10 years and just now moving this month. The neighborhood is safe not a lot of crime just a few thieves here and there that steal packages from ppls door steps occasionally."
    1
    Flag
  • Dismiki24
    "Lots of dogs in our neighborhood but many don’t pick up after their dogs. There is a dog park nearby "
    0
    Flag
  • Jason M.
    "We see people walk their dogs all the time. The neighborhood has dog stations for easy to dispose of waste. "
    0
    Flag
  • Megan E.
    "You will love it! Lots of dog owners and very kind. Lots of doggy poop bag stations as we all know! Great dog parks and trails to go on lovely long walks. "
    13
    Flag
  • Zimmiac
    "Everything is very nice ,and the persons are very nice ,very quite area and the schools are good also,parks and events as well very nice"
    0
    Flag
  • Lil D.
    "The people and shops are great. Love all the bike tails as well. Every Saturday they have the farmers market and quite enjoyable to go to and walk around. "
    0
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  • John D. H.
    "average, plenty of bus access, no major traffic issues. normal boring vanilla winter garden. lahdeedah"
    0
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  • Hollister M.
    "Lots of dogs. Most people are very polite about their dogs. People with cats do not keep them indoors and they roam the streets a lot. Most people pick up after their dogs and keep them on leashes."
    0
    Flag
  • Jim
    "It’s an amazing place to love. Doesn’t feel like living in Florida. I love living the country and still being close to Disney"
    6
    Flag
  • Cathy
    "Great it is safe and very homey the people are friendly and irs all clean. Very close to shopping places to eat and nice bars "
    5
    Flag
  • Jonathancrespo21
    "We have a neighborhood Facebook page open to everyone and we use this to communicate with each other regularly. We participate in food drives, raise money for special causes, and even sponsor dinners for our local police, firefighters, and nurses."
    0
    Flag
  • Chuckfink
    "Farmers market every Saturday. Monthly events downtown, car shows, Christmas party, local community theater. Things to do almost every week."
    0
    Flag
  • Valerie
    "Weekend Farmers Market. Beautiful downtown area. Older historic feeling. Very convenient with shops food and stores. Best city I've lived in since being here in Florida."
    0
    Flag
  • jay j
    "People love dogs. They are loving animals that make everyone happy when they see them. Most people now a days have dogs"
    0
    Flag
  • Nicola O.
    "Some neighbors don’t clean up after their pets or leave their pets on the balcony barking all night long, but there is a lot of open grass fields and dog stations all throughout. "
    0
    Flag
  • Candy H.
    "Winter Garden Farmer’s Market and shows going on at the Garden Theatre, along with more dog friendly mom and pop places."
    0
    Flag
  • Ryanm1995
    "They will love this neighborhood. Bright open space to walk around. We also have a lot of friendly dog in our neighborhood. "
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 237 James Dr

  • What is 237 James Dr estimated to be worth?
    Trulia's estimated value for 237 James Dr in Winter Garden, FL is $392,200.
  • What is the price history for 237 James Dr?
    237 James Dr in Winter Garden, FL last sold for $118,000 in November 2012.
  • Is Winter Garden a buyer's or seller's market?
    Winter Garden is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Winter Garden?
    The median sale price in Winter Garden is $583K. That is down $3.33K from the prior month.
  • Does 237 James Dr have air conditioning?
    Yes, 237 James Dr in Winter Garden, FL has air conditioning.
  • How big is the lot at 237 James Dr?
    The lot at 237 James Dr in Winter Garden, FL is about 0.24 acres (10,454 sq ft).

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Off Market Homes Near 237 James Dr

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