299 Orient Dr, Saint Augustine, FL 32092
Property image
Property image
OFF MARKET

$309,100

Trulia Estimate
as of Sep 29, 2026
  • 3 Beds
  • 2 Baths
  • 1,288 sqft

299 Orient Dr, Saint Augustine, FL 32092

Home Highlights

Single-Family Home
1,288 sqft
$240/sqft

Local Information

  • Map ViewExplore the area around 299 Orient Dr.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Get rewarded for rental payments and more through FirstKey Homes Rewards - a rewarding and fun loyalty program. Get the home you want and the value you deserve with FirstKey Homes. Use our website to Apply Online, Schedule a Self-Tour, Review Resident Qualifications or Search More Homes; or contact our leasing department for help today. Pets are welcome. Apply soon, homes can go fast!

3 bedroom, 2 bathroom rental home in St Augustine, FL, may be just the home for you.

FirstKey Homes, LLC is an Equal Housing Lessor under the FHA. Applicable local, state and federal laws may apply. Lease terms and conditions apply. This is not an offer to rentyou must submit additional information for review and approval. Listed features may not be accurate; confirm details with a leasing representative.

Certain cities and municipalities including St. Louis and Chicago require a home inspection prior to a new resident taking possession of the home. If you are leasing a home in one of these areas, please note that your move-in date could be adjusted to accommodate inspection requirements. Please ask your leasing agent for more details.

BEWARE OF RENTAL SCAMS: FirstKey Homes exclusively manages our homes (no third-party management). We do not lease homes through Craigslist, SocialServe, LetGo, Facebook Marketplace or other classified advertising services.

All applications and lease signing can only be completed through FirstKeyHomes.com using the RentCafe portal. We will never ask for wire transfers, cash apps like Venmo, Zelle, CashApp PayPal, or any other transferring method to collect funds. See FirstKey Homes website for full details and conditions. Listing photos are provided to help you select a home; all photos shown are for representative and illustrative purposes only but may not be exact. Colors and photo size may vary based on different resolutions, hue, brightness, contrast, or other photo variations. Photos on websites may be modified, changed, or amended at any time. For new construction homes, actual homes may vary, photos may be of similar home/floorplan, home may be under construction and photos may not be of actual home, individual homes, amenities, features, and views may differ. If you have any concerns, please schedule a tour prior to applying or leasing the listed home. This property allows self guided viewing without an appointment. Contact for details.
299 Orient Dr, Saint Augustine, FL 32092 is a 3 bedroom, 2 bathroom, 1,288 sqft single-family home. It last sold for $380,000 on May 20, 2022 (19,538% above the $1,935 asking price). More recently, it was listed as a rental in May 2024 with an asking price of $2,500 per month. That rental listing was removed on August 14, 2024. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $309,100, with a rent estimate of $2,205/month.
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Home Details for 299 Orient Dr

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: Contact For Details

Comparable Sales for 299 Orient Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
177 ORIENT Drive, Saint Augustine, FL
0.13
Single-Family Home
$349,000
06/09/26
4
2
1,944 sqft
35 MONTSERRAT Drive, Saint Augustine, FL
0.61
Single-Family Home
$365,000
07/21/26
3
2
1,548 sqft
50 PINE FOREST Court, Augustine, FL
0.51
Single-Family Home
$502,000
11/07/25
3
2
2,289 sqft
50 Pine Forest Ct, Saint Augustine, FL
0.51
Single-Family Home
$502,000
11/07/25
3
2
2,602 sqft
250 KING GEORGE AVENUE, Saint Augustine, FL
0.62
Single-Family Home
$420,000
01/04/26
3
2
2,126 sqft
165 CROWN COLONY Road, Saint Augustine, FL
0.84
Single-Family Home
$360,000
03/31/26
3
2
1,716 sqft
300 Downs Corner Rd, Saint Augustine, FL
0.77
Single-Family Home
$423,000
03/12/26
3
2
2,208 sqft
155 MYRTLE OAK Court, Saint Augustine, FL
0.71
Single-Family Home
$420,000
04/23/26
4
2
2,103 sqft
270 KING GEORGE Avenue, Saint Augustine, FL
0.63
Single-Family Home
$385,000
11/20/25
4
3
2,027 sqft
22 MYRTLE OAK Court, Saint Augustine, FL
0.84
Single-Family Home
$425,000
07/20/26
3
2
2,082 sqft

Nearby homes

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Rental Market Trends in Saint Augustine

Last updated Sep 2026
Trulia Rent Estimate$2,205/mo
Average rent
$2.35K
$20MoM
Available listings
681
View rental market trends in Saint Augustine, FL

Around this home

What Locals Say about Saint Augustine

At least 670 Trulia users voted on each feature.

  • 91 % Say it's dog friendly

  • 90 % Say car is needed

  • 79 % Say there's holiday spirit

  • 79 % Say yards are well-kept

  • 74 % Say people would walk alone at night

  • 73 % Say it's quiet

  • 70 % Say parking is easy

  • 68 % Say kids play outside

  • 63 % Say there's wildlife

  • 63 % Say there are sidewalks

  • 60 % Say neighbors are friendly

  • 56 % Say they plan to stay for at least 5 years

  • 53 % Say streets are well-lit

  • 40 % Say there are community events

  • 35 % Say it's walkable to restaurants

  • 31 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "Great place to raise your family. The kids are kind and friendly and the schools are awesome! Plenty of community parks."
    0
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  • Trulia User
    "Great place to raise kids "
    0
    Flag
  • Trulia User
    "My neighborhood is attractive and peaceful. It’s green and full of unique houses and friendly people. The only problem is that the traffic is loud and too fast. "
    1
    Flag
  • Trulia User
    "There are nice decorations for each holiday. Other than that it’s just a friendly neighborhood and everyone is friendly and nice. "
    0
    Flag
  • Xavier.rivera11
    "Its very safe. I like it a lot. A lot of families and friendly people. I feel that the area is growing and still needs more activities in the amenity to have a better community "
    1
    Flag
  • Tiffany Villano
    "It’s a great community. Lots of kids and amenities Both close to Jacksonville downtown and Saint Augustine Lots of shopping food commercial lots of restaurants"
    0
    Flag
  • Ilester1862
    "I’ve lived in this neighborhood for over 5 years and love it. Neighbors are great and care for their homes. Very active community. Feel safe."
    1
    Flag
  • Tiffany Villano
    "Schools are decent. Lots to do every where even though people complain that there isnt. There’s more infrastructure to come in the next couple years. Overall quiet calm communities working families Love it here "
    0
    Flag
  • Gregory McCain
    "Lots of space for walking dogs in natural surroundings including small lakes and ponds. Almost everyone uses a leash when walking their dog."
    0
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  • Trulia User
    "Fish market, veggie stand and a historical park all in walking very short distance and no HOA, intercoastal is right here too"
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  • Connie Worley
    "It is quiet and off the main road. Neighbors are friendly and polite. There is a good mixture of families, middle aged and retirees. The neighborhood borders a state preserve, so no development will be allowed to the east. It’s only a ten minute drive to the beach."
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  • Evan Martinez
    "It is a kid friendly neighborhood, the can play unsupervised in culdasac and neighbors watch out for them "
    0
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  • Qgsdn2x7dk
    " Nice it’s really nice to live here and grow up here very kid friendly and great for walks I love it here"
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  • Lesley Plott
    "The neighborhood is car dependent but public transportation is easily accessible. The area is growing rapidly."
    0
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  • kathyafleming
    "From here it’s walkable to work eats and downtown. All the sites are within walking distance. It’s a great community for walking. There is a drawbridge off the island so traffic can back up but it clears fast. It’s a slower pace. "
    0
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  • 66alice69
    "Busy on week days commute times morning and But easy travel mid day and also weekends best on Sunday"
    0
    Flag
  • Syn2267
    "Having a Friendly dog and pick up after your dog. Master should be able to tame their dog. Not curbing your dog. "
    0
    Flag
  • Nichols
    "We have lived in our neighborhood for four years. Everything that we could want is only a 10 minute drive from us"
    0
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  • Randi Simmons
    "Trailmark is a family friendly Neighborhood and beautiful community. It is a gem of a place to live! "
    0
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  • stewart_mendenhall
    "We have many miles of walkways as well as a dog park. There are a lot of people that walk their dogs through our neighborhood and all seem very friendly for the most part. "
    0
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  • kathyafleming
    "St augustine is growing rapidly. Sometime you wait 15 or 20 minutes in traffic to get downtown. It’s friendly but be prepared to have ups and downs in traffic if you are carting children to snd from activities. "
    0
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  • Trulia User
    "Principals in downtown is shady af. Staff is smug. No counselors so be mindful of how the school handles students mental health."
    0
    Flag
  • kathyafleming
    "You can walk downtown or to restaurants and brewery’s on the boulevard. It’s got wide quiet residential streets and beautiful trees. People are friendly and everyone knows everyone else. There are amazing landmarks near by, a marina, the lighthouse and the Castillo. "
    0
    Flag
  • kathyafleming
    "Driving is easy but crowded during tourist season. Mornings are generally not bad at all. At 5 pm commute may be crowded x "
    0
    Flag
  • Elizabeth Skidmore
    "There aren’t any open areas to walk with your dog and the community areas do not have doggie bags or disposal areas. Also many of the neighbors post signs that are not dog friendly, even for something as harmless as walking on their grass "
    30
    Flag
  • Renee Hulse
    "Old town USA. You can fish, kayak, hike and swim. The amenities are wonderful and the neighbors are even better"
    6
    Flag
  • Sabena H.
    "No public transportation. Still a little remote, but is building quickly. Bartram Trail School district."
    2
    Flag
  • Adrianna H.
    "There is No dog park. Which would be nice. But plenty of walk ways and trails to walk. Most of the dogs are very friendly. "
    9
    Flag
  • Peter T.
    "Nice place to live many people very friendly it’s hot though bring sun screen and water but also bug spray because mosquitos are a plenty "
    4
    Flag
  • Adrianna H.
    "Every Friday is Food Truck Friday up at the amenity center. Also kids sporting events and certain holiday activities as well. "
    0
    Flag
  • Srrossi
    "Quiet. Plenty of Law Enforcement in the neighborhood. I trust my neighbors. I enjoy my 2 mile walk through our neighborhood."
    0
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  • Sarah K.
    "This town is growing as a dog friendly area. There is a lot of neighborhoods and local businesses that allow dogs. Most people are super excited to great your and your pup. "
    1
    Flag
  • Candice S.
    "Christmas stroll and lights display make this town special. Small town feel, fabulous food. History makes this place special."
    1
    Flag
  • Kristen K.
    "You need transportation for this community. There is no public transportation. You average about 30 minutes from most places ."
    0
    Flag
  • Richard D.
    "There are a lot of them in the neighborhood. Many people own dogs, but it is important to pick up after pets and not let them run wild."
    1
    Flag
  • Egbacro
    "Epic theatre is close by, and downtown is about a 10min drive. The beach is located in Anastasia Island which has a lot of activities. the Lighthouse is nearby, and Saint Augustine’s beach is through the 312 bridge. There is an Amphitheatre close by which has many local and international events. Loads of restaurants, wine tasting and bars, shops/boutiques, museums including the Fountain of youth ca be visited."
    1
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  • Tkendall344
    "Always an event. St Augustine people care regardless if they know you or not the community always come together during crisis or when someone need assistance. We are St. Augustine Strong"
    0
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  • Terri.degrande
    "No specific events. It’s just a nice, established, well-maintained neighborhood with a cheap home owners association that really is functional, and neighbors are friendly and range widely in age. There’s tons of sidewalks, parks, ponds, wildlife, and very easy access to all types of stores and restaurants. "
    1
    Flag
  • Melvinemccall
    "Neighbors watch out for each other and are always ready to help. Cookouts about twice a year in the neighborhood open to all "
    0
    Flag
  • Jacqueline
    "We do not have many events in our neighborhood we only have quarterly yard sales. The neighbors are friendly and the neighborhood is beautiful."
    0
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LGBTQ Local Legal Protections

Price and Tax history

DateEventPrice
Aug 14, 2024
Source: Zillow Rentals
ListingRemoved
$1,935
Aug 8, 2024
Source: Zillow Rentals
PriceChange
$2,050
Price decreased by 3%
Aug 1, 2024
Source: Zillow Rentals
PriceChange
$2,115
Price decreased by 5%
Jul 25, 2024
Source: Zillow Rentals
PriceChange
$2,225
Price decreased by 8%
Jul 19, 2024
Source: Zillow Rentals
PriceChange
$2,425
Price decreased by 3%

Frequently asked questions about 299 Orient Dr

  • What is 299 Orient Dr estimated to be worth?
    Trulia's estimated value for 299 Orient Dr in Saint Augustine, FL is $309,100.
  • What is the price history for 299 Orient Dr?
    299 Orient Dr in Saint Augustine, FL last sold for $380,000 in May 2022.
  • Is Saint Augustine a buyer's or seller's market?
    Saint Augustine is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Saint Augustine?
    The median sale price in Saint Augustine is $429K. That is down $2.5K from the prior month.

Homes for rent near 299 Orient 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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