260 Rolling Oaks Rd, Saint Augustine, FL 32086
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Property image
OFF MARKET

260 Rolling Oaks Rd
Saint Augustine, FL 32086

  • 3 Beds
  • 2 Baths
  • 1,797 sqft (on 0.57 acres)

$420,000

Trulia Estimate
as of Aug 18, 2026
Est. Refi. Payment $2,664/mo*
Refinance Your Home

$420,000

Trulia Estimate
as of Aug 18, 2026
Est. Refi. Payment $2,664/mo*
Refinance Your Home
3 Beds
2 Baths
1,797 sqft
(on 0.57 acres)

Home Value

Trulia Estimate
$420K
Since last month
Increased$2K (+0.5%)
Since last year
Increased$21K (+5.3%)
Since last sale
Increased$118K (+38.6%)
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 +65% in the last 10 years
MonthEstimated value
2026
August 2026$423K
July 2026$421K
June 2026$426K
May 2026$418K
April 2026$411K
March 2026$401K
February 2026$400K
January 2026$395K
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
704 CHARMWOOD Drive, Saint Augustine, FL
0.53
Single-Family Home
$325,000
03/27/26
4
2
2,200
3663 2nd St, Saint Augustine, FL
0.29
Single-Family Home
$400,000
10/06/25
4
3
3,149
3740 BLUFF Lane, Augustine, FL
0.35
Single-Family Home
$475,000
04/22/26
4
2
1,619
3305 Turtle Creek Rd, Saint Augustine, FL
0.41
Single-Family Home
$360,000
10/14/25
3
2
1,539
3297 TURTLE CREEK Road, Saint Augustine, FL
0.37
Single-Family Home
$450,000
04/15/26
3
2
1,708
540 WILLOW WALK Place, Saint Augustine, FL
0.67
Single-Family Home
$420,000
12/22/25
3
2
1,872
112 Crooked Tree Trl, Saint Augustine, FL
0.73
Single-Family Home
$355,000
07/21/26
3
2
2,004
3508 Kings Rd S, Saint Augustine, FL
0.54
Single-Family Home
$550,000
07/15/26
3
2
2,319
521 Jeffrey Dr, Saint Augustine, FL
0.47
Single-Family Home
$385,500
04/24/26
3
2
1,620
231 CREEKSIDE Drive, Saint Augustine, FL
0.08
Single-Family Home
$715,000
05/06/26
4
3.5
3,038

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
231 CREEKSIDE Drive, Saint Augustine, FL 32086
0.08
$715,000
4
3.5
3,038
Recently Sold
166 CREEKSIDE Drive, Saint Augustine, FL 32086
0.13
-
-
-
-
Off Market
161 Creekside Dr, Saint Augustine, FL 32086
0.17
$641,400
3
2
1,923
Off Market
121 Creekside Dr, Saint Augustine, FL 32086
0.22
$1,032,700
4
2.5
3,648
Off Market
155 Supreme Ct, Saint Augustine, FL 32086
0.24
$400,200
3
2
1,560
Off Market
3299 CALLE CORTEZ, Saint Augustine, FL 32086
0.25
$309,500
3
2
1,092
Off Market
200 A Brainard St, Saint Augustine, FL 32086
0.28
$395,000
3
2
1,475
Off Market
3601 2nd St, Saint Augustine, FL 32086
0.29
$561,200
3
2
2,216
Off Market
3641 2nd St, Saint Augustine, FL 32086
0.29
$531,300
3
2
2,216
Off Market
200 A BRAINARD Drive, Saint Augustine, FL 32086
0.30
$389,200
3
2
1,475
Off Market
3530 CARMEL Road, Saint Augustine, FL 32086
0.31
$305,600
3
2.5
1,300
Off Market
3466 CARMEL Road, Saint Augustine, FL 32086
0.33
$379,100
4
2
1,690
Off Market

Local Information

  • Map ViewExplore the area around 260 Rolling Oaks Rd.
  • Schools1 Preschool School1 Elementary School2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1984
Lot Size
0.57 acres
Living Area
1,797 sqft
Price/Sqft
$234
Parking
Garage

About this House

Tucked away on a secluded cul-de-sac in Osceola Point, this three bedroom, two bath home is a blank canvas ready for your touch! An amazing half acre of property, with moss-draped trees and endless opportunity. Enjoy looking over your expansive back yard from the large screened patio or second floor balcony. No HOA means you have room for your toys and NO additional fees. Freshly painted inside and out, with new carpet and A/C. A short drive to the beach or historic downtown St. Augustine will make reality feel like a vacation!
260 Rolling Oaks Rd, Saint Augustine, FL 32086 is a 3 bedroom, 2 bathroom, 1,797 sqft single-family home built in 1984. It last sold for $305,000 on Mar 29, 2021. It is currently off market. The Trulia Estimate is $420,000, with a rent estimate of $2,428/month.

Home Details for 260 Rolling Oaks Rd

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Carpet
Interior Details
Types of Rooms: Dining Room
Appliances & Utilities
Cable ReadyDishwasherMicrowave
Fireplace & Spa
FireplaceHot Tub or Spa

Exterior Features

Exterior Home Features
Roof: CompositionDeckExterior: WoodFoundation Type: ConcretePatioPorch
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 1984Year Updated: 1989
Property Type / Style
Property Type: Single Family HomeArchitecture: Contemporary

Community

Units in Building: 1

Lot Information

Lot Area: 0.57 acres

Mobile R/V

RV Parking
Rv Parking

Price and Tax history

DateEventPrice
Mar 29, 2021
Source: N/A
Sold
$305,000
Mar 1, 2021
Source: realMLS #1090271
Pending
$299,900
Jan 29, 2021
Source: realMLS #1090271
Contingent
$299,900
Jan 29, 2021
Source: realMLS #1090271
PendingToActive
$299,900
Jan 16, 2021
Source: realMLS #1090271
Contingent
$299,900

Market trends in Saint Augustine

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$432K
$13.33KMoM
Sale-to-List Price
97.5%
0.3%MoM
Price per sq ft
$227
$1MoM
Available listings
1789
109MoM
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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 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"
    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
    Flag
  • 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
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  • 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
  • Xtxp5qb76x
    "No side walks to scoot around, not many activities organised by the county, libraries don’t offer as much for kids as other states. Even thought great place to raise a family "
    9
    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
    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

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Explore by feature - Pet Friendly

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Homes for sale near 260 Rolling Oaks Rd

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Off Market Homes Near 260 Rolling Oaks Rd

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Frequently asked questions about 260 Rolling Oaks Rd

  • What is 260 Rolling Oaks Rd estimated to be worth?
    Trulia's estimated value for 260 Rolling Oaks Rd in Saint Augustine, FL is $420,000.
  • What is the price history for 260 Rolling Oaks Rd?
    260 Rolling Oaks Rd in Saint Augustine, FL last sold for $305,000 in March 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 $432K. That is up $13.33K from the prior month.
  • Does 260 Rolling Oaks Rd have air conditioning?
    Yes, 260 Rolling Oaks Rd in Saint Augustine, FL has air conditioning.
  • How big is the lot at 260 Rolling Oaks Rd?
    The lot at 260 Rolling Oaks Rd in Saint Augustine, FL is about 0.57 acres (24,829 sq ft).