5565 Datil Pepper Rd, Saint Augustine, FL 32086
Property image
Property image
OFF MARKET

$367,900

Trulia Estimate
as of Sep 28, 2026
  • 3 Beds
  • 2 Baths
  • 1,789 sqft

5565 Datil Pepper Rd, Saint Augustine, FL 32086

Home Highlights

Single-Family Home
1,789 sqft
$206/sqft
Attached Garage

Local Information

  • Map ViewExplore the area around 5565 Datil Pepper Rd.
  • Schools1 Preschool School1 Elementary School2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

What's unique:Corner houseWasher dryer hook-upsNew vinyl flooringPrivate yard
Nice quiet block, corner house located in St.Augustine, 2 car garage & off road parking , private yard
New vinyl flooring throughout.
Washer dryer hook-ups
20mins to downtown St.Augustine close to shopping

Non-smokers preferred
Must pass background and credit check , credit score of 650 or higher no evictions .
Maximum of 2 pets, no sub-leasing, must maintain lawn and garden
Does not include utilities, non refundable pet fee if $200. Total to move in w/o pet $4200 or $4400 with pets. this not all inclusive as other rules apply.
5565 Datil Pepper Rd, Saint Augustine, FL 32086 is a 3 bedroom, 2 bathroom, 1,789 sqft single-family home. It last sold for $189,000 on Feb 7, 2005 (8,900% above the $2,100 asking price). More recently, it was listed as a rental in February 2025 with an asking price of $2,100 per month. That rental listing was removed on March 8, 2025. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $367,900, with a rent estimate of $2,339/month.

Home Details for 5565 Datil Pepper Rd

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: Central AirHeating Fuel: Forced Air
Appliances & Utilities
DishwasherMicrowaveRefrigerator

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: 1 YearAvailable: now

Exterior Features

Parking & Garage
Parking: Attached Off Street, On Site

Comparable Sales for 5565 Datil Pepper Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
5540 DATIL PEPPER Road, Saint Augustine, FL
0.08
Single-Family Home
$515,000
06/12/26
3
2
1,536 sqft
5475 DATIL PEPPER Road, Saint Augustine, FL
0.14
Single-Family Home
$334,000
02/12/26
3
2
1,248 sqft
5730 Datil Pepper Rd, Saint Augustine, FL
0.21
Single-Family Home
$440,000
12/09/25
3
2
1,800 sqft
261 Brantley Harbor Dr, Saint Augustine, FL
0.20
Single-Family Home
$439,900
10/03/25
3
2
1,908 sqft
165 Summer Point Dr, Saint Augustine, FL
0.28
Single-Family Home
$359,000
12/31/25
4
2
1,734 sqft
5296 Timucua Cir, Saint Augustine, FL
0.09
Single-Family Home
$395,000
09/18/26
4
2.5
2,142 sqft
5263 ELLEN Court, Saint Augustine, FL
0.26
Single-Family Home
$390,000
05/29/26
4
2
1,890 sqft
5775 Datil Pepper Rd, Saint Augustine, FL
0.27
Single-Family Home
$440,000
05/14/26
3
2
2,450 sqft
5227 ELLEN Court, Saint Augustine, FL
0.41
Single-Family Home
$339,000
04/24/26
3
2
1,547 sqft
124 Santorini Ct, Saint Augustine, FL
0.48
Single-Family Home
$310,000
05/15/26
3
2
1,422 sqft

Nearby homes

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Rental Market Trends in Saint Augustine

Last updated Sep 2026
Trulia Rent Estimate$2,339/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."
    0
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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
    Flag
  • Qgsdn2x7dk
    " Nice it’s really nice to live here and grow up here very kid friendly and great for walks I love it here"
    0
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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
    Flag
  • 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
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  • 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
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  • 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
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  • 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
Mar 8, 2025
Source: Zillow Rentals
ListingRemoved
$2,100
Feb 26, 2025
Source: Zillow Rentals
Listed For Rent
$2,100
Feb 7, 2005
Source: N/A
Sold
$189,000
May 16, 2003
Source: N/A
Sold
$142,000
May 10, 2001
Source: N/A
Sold
$130,000

Frequently asked questions about 5565 Datil Pepper Rd

  • What is 5565 Datil Pepper Rd estimated to be worth?
    Trulia's estimated value for 5565 Datil Pepper Rd in Saint Augustine, FL is $367,900.
  • What is the price history for 5565 Datil Pepper Rd?
    5565 Datil Pepper Rd in Saint Augustine, FL last sold for $189,000 in February 2005.
  • 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.
  • Does 5565 Datil Pepper Rd have air conditioning?
    Yes, 5565 Datil Pepper Rd in Saint Augustine, FL has air conditioning.
  • Does 5565 Datil Pepper Rd have parking?
    Yes, 5565 Datil Pepper Rd in Saint Augustine, FL has on-site parking.

Homes for rent near 5565 Datil Pepper Rd

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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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