4307 Old Sycamore Loop, Winter Garden, FL 34787
Property image
Property image
OFF MARKET

$734,800

Trulia Estimate
as of Sep 12, 2026
  • 1 Bed
  • 1 Bath
  • 3,414 sqft

4307 Old Sycamore Loop, Winter Garden, FL 34787

Home Highlights

Single-Family Home
3,414 sqft
$215/sqft

Local Information

  • Map ViewExplore the area around 4307 Old Sycamore Loop.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

**Cozy In-Law Suite in Charming Winter Garden

Discover your peaceful retreat in Winter Garden, just 15 minutes from the excitement of Orlando's theme parks and shopping outlets! This welcoming suite features a private entrance and a comfortable en-suite bathroom, providing you with the privacy you desire.

Enjoy the convenience of being within walking distance to downtown's delightful restaurants, shops, and markets. Stay active with access to the community gym and refreshing pool.

Unwind in your inviting suite, complete with a plush bed, perfect for recharging after a day of exploring all that Orlando has to offer. Plus, for added convenience, take advantage of our laundry service for just $3.00 per pound wash and fold included!

Experience the magic of the theme parks while enjoying the cozy charm of this small-town getaway. Book your stay today for an unforgettable experience!

3months 6months 12months
4307 Old Sycamore Loop, Winter Garden, FL 34787 is a 1 bedroom, 1 bathroom, 3,414 sqft single-family home. It last sold for $591,000 on Aug 31, 2021 (65,567% above the $900 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $734,800, with a rent estimate of $1,474/month.

Home Details for 4307 Old Sycamore Loop

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: Central AirHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Floors: Carpet
Room & Shared Space
Room is furnishedHas private bath

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: 1 YearUtilities Share: included

Exterior Features

Pool
Pool
Parking & Garage
Parking: Off Street Parking, On Site

Building

Community rooms
Fitness Center

Comparable Sales for 4307 Old Sycamore Loop

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
4360 OLD SYCAMORE, Winter Garden, FL
0.06
Single-Family Home
$625,000
02/03/26
4
3
2,548 sqft
14419 MAGNOLIA RIDGE LOOP, Winter Garden, FL
0.07
Single-Family Home
$650,000
11/14/25
5
3
2,514 sqft
14580 CEDAR HILL DRIVE, Winter Garden, FL
0.18
Single-Family Home
$557,500
01/16/26
4
2
2,019 sqft
4076 GREEN ORCHARD AVENUE, Winter Garden, FL
0.16
Single-Family Home
$630,000
03/10/26
5
3
2,867 sqft
3242 IRISH PEACH DRIVE, Winter Garden, FL
0.27
Single-Family Home
$490,000
05/04/26
3
2
2,120 sqft
14430 ORCHARD HILLS BOULEVARD, Winter Garden, FL
0.27
Single-Family Home
$595,000
03/31/26
3
2.5
2,471 sqft
13958 MAGNOLIA RIDGE LOOP, Winter Garden, FL
0.32
Single-Family Home
$565,000
06/17/26
3
2
2,075 sqft
3167 WINESAP WAY, Winter Garden, FL
0.29
Single-Family Home
$550,000
06/05/26
4
2
2,115 sqft
3136 IRISH PEACH DRIVE, Winter Garden, FL
0.38
Single-Family Home
$585,000
03/04/26
3
2
2,136 sqft
14342 WHITE MOSS WAY, Winter Garden, FL
0.29
Single-Family Home
$540,000
12/02/25
3
2.5
2,368 sqft

Nearby homes

Get a sense of prices in the area by checking nearby homes.
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Rental Market Trends in Winter Garden

Last updated Sep 2026
Trulia Rent Estimate$1,474/mo
Average rent
$2.75K
Available listings
315
View rental market trends in Winter Garden, FL

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 "
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  • 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 ."
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  • 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
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  • 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
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  • 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
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  • 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 "
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  • 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
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  • 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! "
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  • 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"
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  • 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
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  • 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
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  • Jason M.
    "We see people walk their dogs all the time. The neighborhood has dog stations for easy to dispose of waste. "
    0
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  • 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
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  • 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"
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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
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  • 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
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  • Chuckfink
    "Farmers market every Saturday. Monthly events downtown, car shows, Christmas party, local community theater. Things to do almost every week."
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  • 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."
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  • 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
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  • 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
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LGBTQ Local Legal Protections

Price and Tax history

DateEventPrice
Aug 28, 2024
Source: Stellar MLS #O5960425
ListingRemoved
$585,000
Aug 31, 2021
Source: N/A
Sold
$591,000
Jul 28, 2021
Source: Stellar MLS #O5960425
Pending
$585,000
Jul 27, 2021
Source: RE/MAX International
ListingRemoved
Jul 22, 2021
Source: Stellar MLS #O5960425
Listed For Sale
$585,000

Frequently asked questions about 4307 Old Sycamore Loop

  • What is 4307 Old Sycamore Loop estimated to be worth?
    Trulia's estimated value for 4307 Old Sycamore Loop in Winter Garden, FL is $734,800.
  • What is the price history for 4307 Old Sycamore Loop?
    4307 Old Sycamore Loop in Winter Garden, FL last sold for $591,000 in August 2021.
  • 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 $585K. That is up $1.67K from the prior month.
  • Does 4307 Old Sycamore Loop have air conditioning?
    Yes, 4307 Old Sycamore Loop in Winter Garden, FL has air conditioning.
  • Does 4307 Old Sycamore Loop have a pool?
    Yes, 4307 Old Sycamore Loop in Winter Garden, FL has a pool.

Homes for rent near 4307 Old Sycamore Loop

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Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.
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