16396 Grey Pine Dr, Winter Garden, FL 34787
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OFF MARKET

16396 Grey Pine Dr
Winter Garden, FL 34787

  • 5 Beds
  • 3 Baths
  • 2,231 sqft

$606,100

Trulia Estimate
as of Aug 23, 2026

$606,100

Trulia Estimate
as of Aug 23, 2026
  • 5 Beds
  • 3 Baths
  • 2,231 sqft

Home Highlights

Property Type
Single-Family Home
Living Area
2,231 sqft
Price/Sqft
$272
Parking
Attached Garage

Local Information

  • Map ViewExplore the area around 16396 Grey Pine Dr.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare professional maintenance. Your estimated total monthly payment is $3267.90, which includes base rent and required services. Base rent varies based on selected lease term. Apply for select homes by 7/25 to get your first month of base rent free. *For a detailed price breakdown, please refer to each listing.

This home is part of Silverleaf Oaks, a thoughtfully planned community. Learn More about what Silverleaf Oaks has to offer.

Silverleaf Oaks features newly built 3 to 5-bedroom, 2.5 to 3-bathroom homes with three thoughtfully designed floor plans. Located just outside Orlando, this community blends modern living with unmatched convenience. Each home offers Smart Home technology, granite countertops and 2-car garages, combining style and functionality. Residents enjoy easy access to nearby retailers, scenic trails and public lagoons in Winter Garden. Silverleaf Oaks offers the perfect balance of comfort, location and value.

At Invitation Homes, we offer pet-friendly, yard-having homes for lease with Smart Home technology in awesome neighborhoods across the country. Live in a great house without the headache and long-term commitment of owning. Discover your dream home with Invitation Homes.

Our Lease Easy bundle which includes Smart Home, Air Filter Delivery, and Utilities Management is a key part of your worry-free leasing lifestyle. These services are required by your lease at an additional monthly cost. Monthly fees for pets and pools may also apply.

Home Features and Amenities: Air Conditioning, Garage, Granite Countertops, Long Lease Terms, New Construction, Pet Friendly, Smart Home, W/D Hookups, and professionally managed by Invitation Homes.

 Invitation Homes is an equal housing lessor under the FHA. Applicable local, state and federal laws may apply. Additional terms and conditions apply. This listing is not an offer to rent. You must submit additional information including an application to rent and an application fee. All leasing information is believed to be accurate, but changes may have occurred since photographs were taken and square footage is estimated. See InvitationHomes website for more information.

Beware of scams: Employees of Invitation Homes will never ask you for your username and password. Invitation Homes does not advertise on Craigslist, Social Serve, etc. We own our homes; there are no private owners. All funds to lease with Invitation Homes are paid directly through our website, never through wire transfer or payment app like Zelle, Pay Pal, or Cash App.

For more info, please submit an inquiry for this home. Applications are subject to our qualification requirements. Additional terms and conditions apply. CONSENT TO CALLS & TEXT MESSAGING: By entering your contact information, you expressly consent to receive emails, calls, and text messages from Invitation Homes including by autodialer, prerecorded or artificial voice and including marketing communications. Msg & Data rates may apply. You also agree to our Terms of Use and our Privacy Policy.
16396 Grey Pine Dr, Winter Garden, FL 34787 is a 5 bedroom, 3 bathroom, 2,231 sqft single-family home. More recently, it was listed as a rental in May 2025 with an asking price of $3,310 per month. That rental listing was removed on June 28, 2025. It is currently off market. The Trulia Estimate is $606,100, with a rent estimate of $3,831/month.
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Property Website

Home Details for 16396 Grey Pine Dr

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: Contact For DetailsAvailable: now

Exterior Features

Parking & Garage
Parking: Attached, On Site

Comparable Sales for 16396 Grey Pine Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
6475 BREEZE FILLED LANE, Winter Garden, FL
0.12
Single-Family Home
$578,000
08/14/26
5
3
2,231 sqft
17054 HAGGERTY HOLLOW DRIVE, Winter Garden, FL
0.23
Single-Family Home
$671,324
07/09/26
4
2.5
2,235 sqft
17055 HAGGERTY HOLLOW DRIVE, Winter Garden, FL
0.23
Single-Family Home
$550,683
06/24/26
4
3
2,102 sqft
16347 BRIGHT LEAF RD, Winter Garden, FL
0.28
Single-Family Home
$816,250
12/22/25
5
3
2,922 sqft
17066 HAGGERTY HOLLOW DRIVE, Winter Garden, FL
0.26
Single-Family Home
$769,378
07/29/26
4
3
3,038 sqft
6102 WHISPERING GLEN, Winter Garden, FL
0.32
Single-Family Home
$540,000
07/09/26
4
2.5
1,913 sqft
17037 HAGGERTY HOLLOW DRIVE, Winter Garden, FL
0.24
Single-Family Home
$584,611
07/30/26
4
3.5
2,520 sqft
5138 CITRUS LEAF BOULEVARD, Winter Garden, FL
0.36
Single-Family Home
$745,000
06/30/26
4
3
2,468 sqft
17061 HAGGERTY HOLLOW DRIVE, Winter Garden, FL
0.26
Single-Family Home
$625,882
07/09/26
4
3.5
2,515 sqft
16520 SILVER BROOK WAY, Winter Garden, FL
0.38
Single-Family Home
$545,000
10/20/25
4
2.5
2,114 sqft

Nearby homes

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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
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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 ."
    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
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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
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  • 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 "
    0
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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
    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
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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"
    0
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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
    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
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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
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  • 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
Jun 28, 2025
Source: Zillow Rentals
ListingRemoved
$3,170
Jun 25, 2025
Source: Zillow Rentals
PriceChange
$3,170
Price decreased by 4%
May 7, 2025
Source: Zillow Rentals
Listed For Rent
$3,310

Frequently asked questions about 16396 Grey Pine Dr

  • What is 16396 Grey Pine Dr estimated to be worth?
    Trulia's estimated value for 16396 Grey Pine Dr in Winter Garden, FL is $606,100.
  • 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.
  • What do residents say about Winter Garden?
    Residents describe Winter Garden, FL as dog-friendly, pedestrian-friendly, and easy to park in. See recently sold homes in Winter Garden, FL.
  • Does 16396 Grey Pine Dr have parking?
    Yes, 16396 Grey Pine Dr in Winter Garden, FL has on-site parking.

Homes for rent near 16396 Grey Pine Dr

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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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