5585 Datil Pepper Rd, Saint Augustine, FL 32086
Property image
Property image
OFF MARKET

$521,500

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,683 sqft (on 0.69 acres)

5585 Datil Pepper Rd, Saint Augustine, FL 32086

Est. Refi. Payment $3,518/mo*
Refinance Your Home
Currently Off Market - Sold Sep 16, 2021 for $430,000

Home Value

Trulia Estimate
$522K
Since last month
Decreased$3K (-0.5%)
Since last year
Increased$30K (+6.1%)
Since last sale
Increased$91K (+21%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +125% in the last 10 years
MonthEstimated value
2026
September 2026$521K
August 2026$523K
July 2026$527K
June 2026$522K
May 2026$513K
April 2026$499K
March 2026$492K
February 2026$490K
January 2026$486K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
5730 Datil Pepper Rd, Saint Augustine, FL
0.18
Single-Family Home
$440,000
12/09/25
3
2
1,800
5540 DATIL PEPPER Road, Saint Augustine, FL
0.12
Single-Family Home
$515,000
06/12/26
3
2
1,536
5475 DATIL PEPPER Road, Saint Augustine, FL
0.18
Single-Family Home
$334,000
02/12/26
3
2
1,248
5296 Timucua Cir, Saint Augustine, FL
0.11
Single-Family Home
$395,000
09/18/26
4
2.5
2,142
261 Brantley Harbor Dr, Saint Augustine, FL
0.21
Single-Family Home
$439,900
10/03/25
3
2
1,908
5227 ELLEN Court, Saint Augustine, FL
0.44
Single-Family Home
$339,000
04/24/26
3
2
1,547
165 Summer Point Dr, Saint Augustine, FL
0.27
Single-Family Home
$359,000
12/31/25
4
2
1,734
394 CASSANDRA Lane, Saint Augustine, FL
0.68
Single-Family Home
$445,000
05/01/26
3
2
1,638
121 Morningview Pl, Saint Augustine, FL
0.69
Single-Family Home
$339,000
09/23/26
3
2
1,582
116 MORNINGVIEW Place, Saint Augustine, FL
0.74
Single-Family Home
$387,000
05/28/26
3
2
1,508

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
5296 Timucua Cir, Saint Augustine, FL 32086
0.11
$395,000
4
2.5
2,142
Recently Sold
5540 DATIL PEPPER Road, Saint Augustine, FL 32086
0.12
$515,000
3
2
1,536
Recently Sold
304 BRANTLEY HARBOR DRIVE, Saint Augustine, FL 32086
0.11
$366,600
3
2
1,564
Off Market
5675 Datil Pepper Rd, Saint Augustine, FL 32086
0.09
$481,200
3
2
1,698
Off Market
5610 Datil Pepper Rd, Saint Augustine, FL 32086
0.11
$145,000
-
-
-
Recently Sold
312 Brantley Harbor Dr, Saint Augustine, FL 32086
0.13
$369,000
3
2
2,252
For Sale
5475 DATIL PEPPER Road, Saint Augustine, FL 32086
0.18
$334,000
3
2
1,248
Recently Sold
272 SUNSHINE Drive, Saint Augustine, FL 32086
0.15
$311,500
3
2
1,216
Off Market
272 Brantley Harbor Dr, Saint Augustine, FL 32086
0.17
$398,100
3
2.5
2,465
Off Market
280 Sunshine Dr, Saint Augustine, FL 32086
0.17
$449,200
5
3
2,226
Off Market
5730 Datil Pepper Rd, Saint Augustine, FL 32086
0.18
$440,000
3
2
1,800
Recently Sold
5276 Timucua Cir, Saint Augustine, FL 32086
0.20
$388,600
3
2
1,680
Off Market

Local Information

  • Map ViewExplore the area around 5585 Datil Pepper Rd.
  • Schools1 Preschool School1 Elementary School2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1999
0.69 acre lot
1,683 sqft
$310/sqft
Garage

About this House

This one will have you at hello! Finally, a stunning, tastefully upgraded pool home that sits on .67 acres with everything from roof to floors BRAND NEW. Bring your boat or RV to this completely turn key property that has room for an in law suite or large work shop with lovely preserved woods behind the pool fence. Did I mention the master's stylish tea cup tub with remote control colored LED remote lighting to set the mood for the bathtub lovers? There is new separate shower and a walk in closet with new maple wood soft close drawers with mirror surface and pretty lighting feature. Feel yourself unwind in jacuzza spa or cool off in the sparkling figure 8shaped pool. Stay cool under the lanai as you put steaks on the BBQ or explore nature in the lovely wooded lot in your own back yard. Kitchen adorned with smooth white marble quartz counters with all new stainless GE appliances package with sleek glass cooktop stove and energy saving dish washer included. 2021-08-16
5585 Datil Pepper Rd, Saint Augustine, FL 32086 is a 3 bedroom, 2 bathroom, 1,683 sqft single-family home built in 1999. It last sold for $430,000 on Sep 16, 2021. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $521,500, with a rent estimate of $3,025/month.

Home Details for 5585 Datil Pepper Rd

Interior Features

Levels, Entrance, & Accessibility
Stories: 1Floors: Other, Hardwood
Heating & Cooling
Air ConditioningCooling System: Central
Fireplace & Spa
FireplaceHot Tub or Spa

Exterior Features

Exterior Home Features
Roof: CompositionExterior: StuccoFoundation Type: Concrete
Pool
Pool
Parking & Garage
GarageParking: Garage

Property Information

Year Built
Year Built: 1999Year Updated: 1999
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 0.69 acres

Price and Tax history

DateEventPrice
Sep 16, 2021
Source: N/A
Sold
$430,000
Aug 15, 2021
Source: Berkshire Hathaway HomeServices Florida Network Realty #215740
Pending
$395,000
Aug 15, 2021
Source: St Augustine St Johns County BOR #215740
Contingent
$395,000
Aug 10, 2021
Source: St Augustine St Johns County BOR #215740
Listed For Sale
$395,000
Jan 3, 2003
Source: N/A
Sold
$197,000

Market trends in Saint Augustine

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$429K
$2.5KMoM
Sale-to-List Price
97.4%
Price per sq ft
$228
$0MoM
Available listings
1730
61MoM

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
    Flag
  • 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
    Flag
  • Trulia User
    "Fish market, veggie stand and a historical park all in walking very short distance and no HOA, intercoastal is right here too"
    0
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 5585 Datil Pepper Rd

  • What is 5585 Datil Pepper Rd estimated to be worth?
    Trulia's estimated value for 5585 Datil Pepper Rd in Saint Augustine, FL is $521,500.
  • What is the price history for 5585 Datil Pepper Rd?
    5585 Datil Pepper Rd in Saint Augustine, FL last sold for $430,000 in September 2021.
  • 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 5585 Datil Pepper Rd have air conditioning?
    Yes, 5585 Datil Pepper Rd in Saint Augustine, FL has air conditioning.
  • Does 5585 Datil Pepper Rd have a pool?
    Yes, 5585 Datil Pepper Rd in Saint Augustine, FL has a pool.

Explore by feature - Pet Friendly

304 pet-friendly rentals in Saint Augustine, FL

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Explore by feature - Air Conditioning

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Explore by feature - Pool

321 rentals with a pool in Saint Augustine, FL

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497 rentals with a washer/dryer in Saint Augustine, FL

Explore by feature - Outdoor Space

92 rentals with an outdoor space in Saint Augustine, FL

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Off Market Homes Near 5585 Datil Pepper Rd

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