2099 Winterbourne Dr E #306, Orange Park, FL 32073
Property image
Property image
FOR RENT

$2,300/mo

  • 3 Beds
  • 2 Baths
  • 1,664 sqft

2099 Winterbourne Dr E #306, Orange Park, FL 32073

Cost and fees breakdown
Price may not include required fees and charges.

Home Highlights

Condo
Carport
No Pets
Dishwasher
Central & Central Air

Local Information

  • Map ViewExplore the area around 2099 Winterbourne Dr E #306.
  • Schools2 Preschool Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Wake up to the St. Johns River every morning from your own private balcony. This airy 3-bedroom, 2-bath waterfront condo sits within the gates of one of Orange Park's most storied addresses -- Club Continental, a landmark estate originally built in 1923 as the winter retreat of Caleb Johnson, heir to the Palmolive Soap Company. Today, this romantic and intimate enclave on the banks of the St. Johns River is a world unto itself -- and as a resident of River Oak, you have exclusive access to it. Inside, the unit has been thoughtfully maintained and freshly painted, with hardwood floors, an updated kitchen, and an open floor plan with built-ins and a fireplace that makes every evening feel like a retreat. The generous primary suite features a jetted tub and its own private entrance to the balcony -- where the river view is yours alone. What sets this property apart isn't just the unit -- it's the lifestyle. As a River Oak Condominium Association resident, you can enjoy access to Club Continental's resort-style amenities, including 3 pools and 7 tennis courts Winterbourne Patio home pool that have been lovingly preserved for over a century. The HOA has handled all the heavy lifting -- new roof, bulkhead repairs, exterior maintenance, and grounds upkeep -- so you can simply enjoy it. This is lock-and-leave waterfront living at its finest, in a setting you simply cannot replicate.

Details for 2099 Winterbourne Dr E #306

Interior Features

Heating & Cooling
Heating: CentralAir ConditioningHeating Fuel: Central
Appliances & Utilities
DishwasherRefrigerator

Days on Market

Days on Market: 20 days on Trulia

Property Information

Year Built
Year Built: 1986
Property Type / Style
Property Type: Condo

Rental Terms, Policies & Fees

Lease Term: Negotiable

Exterior Features

Parking & Garage
Parking: Carport, On Site

Agent Information

Listing Agent
MLS/Source ID: 2161534
Report this Listing

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Costs and Fees

Required monthly rent & fees
  • Base rent
    $2,300/mo
Required one-time fees
  • Security deposit
    Contact for details
  • Application fee
    Contact for details
  • Administrative fee
    Contact for details
Pricing is subject to change. All calculations are estimates and provided for informational purposes only. Actual amounts may include additional mandatory or optional fees. Please consult the community manager for a complete breakdown of all rental costs.
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Rental Market Trends in Orange Park

Last updated Sep 2026
Trulia Rent Estimate$2,104/mo
Average rent
$1.88K
$21MoM
Available listings
238
View rental market trends in Orange Park, FL

Around this home

View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Orange Park

At least 535 Trulia users voted on each feature.

  • 88 % Say car is needed

  • 87 % Say it's dog friendly

  • 83 % Say parking is easy

  • 75 % Say there are sidewalks

  • 74 % Say there's holiday spirit

  • 73 % Say yards are well-kept

  • 72 % Say it's quiet

  • 70 % Say kids play outside

  • 60 % Say it's walkable to grocery stores

  • 59 % Say people would walk alone at night

  • 58 % Say streets are well-lit

  • 54 % Say it's walkable to restaurants

  • 52 % Say they plan to stay for at least 5 years

  • 48 % Say neighbors are friendly

  • 44 % Say there's wildlife

  • 23 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Judith De La Cruz
    "I like living here , very safe neighborhood and some place to visit . Very good schools and festivals "
    1
    Flag
  • Levuris.smith
    "So what you always do and you will be fine. The area is nice but there need more restaurants and places to eat around here."
    0
    Flag
  • Taylorburnham53
    "The neighborhood is suprisingly quiet and peaceful, not much going around/ haven’t had any issues feeling unsafe. I don’t let my daughter play in the front yard without me, but that’s more because of speeders in our residential neighborhood. That’s my only problem though "
    0
    Flag
  • Trulia User
    "Love the neighborhood great place to live and lots of community events going on around the area for the entire family. "
    0
    Flag
  • JESSICA SIRLES
    "I love this area and if possible I want to stay here. My kids have a lot of friends here and they love it too."
    0
    Flag
  • Victor Quick
    "I don’t hear gunshots and my area seems relatively safe. It is also very clean and garbage is picked up regularly. Neighbors are very attentive and watch out for each other . "
    1
    Flag
  • Judith De La Cruz
    "I’m very happy living here. Is very quiet neighborhood and the people are very friendly. I have a farm market very close to my house "
    0
    Flag
  • Adnel Rodriguez
    "Hard, the traffic on Blanding BLVD can be difficult at times. This happens especially in the morning hours and from 5 pm on until the late of night. "
    1
    Flag
  • Adnel Rodriguez
    "Independence Day, lots of festivals here in the area, and lots of friendly places near by. I love the fact that there are major stores where we can shop at. "
    2
    Flag
  • Adnel Rodriguez
    "Nothing really! It’s a great neighborhood to live in. It’s very peaceful and safe. There are lots of cats around. "
    1
    Flag
  • Trulia User
    "Busy in the morning going work and busy getting off work. Some homeless people walking around to….."
    3
    Flag
  • Trulia User
    "Easter egg hunt, pool parties, back to school out reach. Community events and other events like that. All family fun"
    1
    Flag
  • Trulia User
    "pet deposit too high, dog parks too small, too many busy roads for a safe or fulfilling dog walk. not like avondale"
    0
    Flag
  • Trulia User
    "I currently drive on the main road towards the base. I also work on the base as well. The area is also well lit as well."
    0
    Flag
  • Blancarj50
    "Christmas is very colorful and happy, the decorate everything very beautiful. The atmosphere is very calm and harmonious. You breathe a lot of peace."
    0
    Flag
  • Kryssynut00
    "Great place to live. Everyone is friendly. Everything you need is right around the area. Close to shopping, food, and other amenities. Feels like home."
    11
    Flag
  • Corgiotter1
    "Never let yr kids be alone in any neighborhood! OP is nice, full of trees, parks, green spaces, restaurants, fast food, slow food, etc. The St Johns River is nearby and very beautiful to walk along."
    1
    Flag
  • Joshua M. H.
    "This area is full of wonderful things to do with a very environmental touch, outgoing and friendly neighborhood. "
    0
    Flag
  • Kentkareng
    "Good place to stay and schooling shopping and enjoy sun set at park and water front feel saved to stay in orange park clay county Florida a lot fun "
    6
    Flag
  • Tatanisha G.
    "We have monthly neighbors meetings. The schools are great! My children can play with no interruptions "
    6
    Flag
  • Annritchey1
    "The area has great parks and amenities for families! Families can walk and bike through the neighborhood and feel safe! "
    1
    Flag
  • Quirm
    "We have culdesac movie nights and neighborhood summer parties. Great neighbors who care very much for one another. "
    0
    Flag
  • Royal Prince
    "Trafficky it’s a lot of people living in O.P., barely any entertaining locations here we need an amusement park..."
    5
    Flag
  • Ashley R.
    "Some people drive fast through the neighborhoods but most neighborhoods are a great place to live. There are schools close by most areas and parks all around. Town activities as well. "
    0
    Flag
  • Jake
    "Good place to live and the people are friendly. Just a nice community to live in and raise your children."
    0
    Flag
  • Brittaniwhitfield
    "Easy to hop on the highway from this area. Everything is close by. Restaurants, grocery stores and the mall is within walking distance."
    0
    Flag
  • Samantha S.
    "I've lived here all my life, the only reason we're moving is cause traffic is so bad. Everything is centralized and there's a great community atmosphere."
    0
    Flag
  • Jamieannbaccas
    "I drive everywhere I go. Unless you live in a populated are where there is a bunch of stores, you have to drive. "
    5
    Flag
  • Dewaldl77
    "It has the clay county schools but it’s still in the Argyle area that is Duval county in Jacksonville Florida."
    1
    Flag
  • Collette L.
    "Everyone knows everyone and pretty friendly. Very quiet area. A lot of children and good schools. Close to everything on Blanding Blvd. everything is conveniently located. A lot of churches that host events."
    5
    Flag
  • Curtisa18
    "no public transportation, but stores are close within walking distance. Easy access to daily needs. Everything is located around here. I love it here in Orange Park"
    4
    Flag
  • Natasha W.
    "We have a neighborhood watch program and website in our community that let’s us know about different events that are going on in our neighborhood."
    1
    Flag
  • Chelsea H.
    "I would like to see a local dog park. The nearest one is either in Middleburg or by NAS and I hate to drive that distance "
    0
    Flag
  • Mike M.
    "I do not know about the dog owners in the community. I am just visiting. There have been many cats seen around though."
    0
    Flag
  • Myyani L.
    "I like this neighborhood. I actually had a package delivered to my apartment and it got their the day before I moved in and a neighbor took it to the office so it wouldn’t be stolen. Very nice people and a lot of houses are being built, schools are very close, stores are clean and stocked. "
    0
    Flag
  • Lydia S.
    "I’ve lived in this are for 6 years, it’s quiet, safe and friendly. There’s tennis courts parks, shopping and a lot of restaurants close by "
    0
    Flag
  • Trulia User
    "I have lived here in this neighborhood for 30years. Most of my neighbors that were here when we moved here have moved away are have died. They are a few of us left."
    3
    Flag
  • Galatioto8
    "I live in a dog friendly neighborhood. Everyone in our neighborhood loves their pets and everyone is out walking them."
    0
    Flag
  • Chari
    "Dog friendly community. Very typical to see people walking their pets up and down the neighborhood throughout the day/night."
    0
    Flag
  • Galatioto8
    "The houses have large backyards so they have lots of room to run. You see neighbors walking their dogs all the time."
    0
    Flag

Local Legal Protections

LGBTQ • Source of Income

Price and Tax history

DateEventPrice
Aug 24, 2026
Source: realMLS #2161534
Listed For Rent
$2,300
Aug 7, 2026
Source: St Augustine St Johns County BOR #262026
Sold
$350,000
Jul 30, 2026
Source: eXp Realty #2141646
Contingent
$365,000
Jul 20, 2026
Source: realMLS #2141646
PriceChange
$365,000
Price decreased by 1%
Jul 9, 2026
Source: realMLS #2141646
PriceChange
$370,000
Price decreased by 1%

Frequently asked questions about 2099 Winterbourne Dr E #306

  • What is 2099 Winterbourne Dr E #306 estimated to be worth?
    Trulia's estimated value for 2099 Winterbourne Dr E #306 in Orange Park, FL is $350,000.
  • What is the price history for 2099 Winterbourne Dr E #306?
    2099 Winterbourne Dr E #306 in Orange Park, FL last sold for $350,000 in August 2026.
  • Is Orange Park a buyer's or seller's market?
    Orange Park is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Orange Park?
    The median sale price in Orange Park is $299K. That is up $4.7K from the prior month.
  • Does 2099 Winterbourne Dr E #306 have parking?
    Yes, 2099 Winterbourne Dr E #306 in Orange Park, FL has on-site parking.

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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
$82,800 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.

New Rentals Nearby

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2099 Winterbourne Dr E #306, Orange Park, FL is a 3 bedroom, 2 bathroom, 1,664 sqft condo built in 1986. 2099 Winterbourne Dr E #306 was listed for rent for $2,300/month on Aug 24, 2026.