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

$625,400

Trulia Estimate
  • 4 Beds
  • 3 Baths
  • 2,787 sqft (on 0.60 acres)

261 Rolling Oaks Rd, Saint Augustine, FL 32086

Est. Refi. Payment $4,212/mo*
Refinance Your Home
Currently Off Market - Sold Mar 27, 2020 for $285,910

Home Value

Trulia Estimate
$625K
Since last month
Increased$7K (+1.1%)
Since last year
Increased$60K (+10.6%)
Since last sale
Increased$339K (+118.7%)
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 +71% in the last 10 years
MonthEstimated value
2026
October 2026$625K
September 2026$610K
August 2026$619K
July 2026$621K
June 2026$631K
May 2026$616K
April 2026$588K
March 2026$577K
February 2026$566K
January 2026$554K
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
231 CREEKSIDE Drive, Saint Augustine, FL
0.08
Single-Family Home
$715,000
05/06/26
4
3.5
3,038
151 Creekside Dr, Saint Augustine, FL
0.15
Single-Family Home
$850,000
06/10/26
3
3
2,880
3253 Turtle Creek Rd, Saint Augustine, FL
0.48
Single-Family Home
$535,000
07/28/26
4
3
2,402
3517 CAROLWOOD Lane, Saint Augustine, FL
0.47
Single-Family Home
$625,000
06/30/26
4
2
2,246
3740 BLUFF Lane, Augustine, FL
0.33
Single-Family Home
$475,000
04/22/26
4
2
1,619
3308 Millwood Way, Saint Augustine, FL
0.61
Single-Family Home
$625,000
02/02/26
4
3
2,507
3445 Kings Rd S, Saint Augustine, FL
0.39
Single-Family Home
$505,000
07/30/26
3
2
1,755
214 RAINTREE Trail, Saint Augustine, FL
0.63
Single-Family Home
$618,000
01/02/26
4
2.5
2,433
5046 Shore Dr, Saint Augustine, FL
0.54
Single-Family Home
$600,000
09/30/26
3
2.5
2,231
704 CHARMWOOD Drive, Saint Augustine, FL
0.53
Single-Family Home
$325,000
03/27/26
4
2
2,200

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 Rolling Oaks Rd, Saint Augustine, FL 32086
0.03
$562,200
3
2
2,394
Off Market
291 Rolling Oaks Rd, Saint Augustine, FL 32086
0.03
$482,400
3
2.5
2,047
Off Market
3779 Laura Ln, Saint Augustine, FL 32086
0.03
$465,500
3
2
2,119
Off Market
3776 Laura Ln, Saint Augustine, FL 32086
0.05
$922,800
5
4
3,982
Off Market
260 Rolling Oaks Rd, Saint Augustine, FL 32086
0.05
$417,100
3
2
1,797
Off Market
290 Rolling Oaks Rd, Saint Augustine, FL 32086
0.05
$516,500
3
2.5
2,772
Off Market
200 Creekside Dr, Saint Augustine, FL 32086
0.05
$561,200
Studio
-
3,267
Off Market
201 Rolling Oaks Rd, Saint Augustine, FL 32086
0.05
$602,900
3
2
2,074
Off Market
230 Rolling Oaks Rd, Saint Augustine, FL 32086
0.06
$509,700
4
2.5
2,000
Off Market
251 Creekside Dr, Saint Augustine, FL 32086
0.06
$508,900
3
3
2,399
Off Market
200 Rolling Oaks Rd, Saint Augustine, FL 32086
0.07
$497,500
3
2
2,431
Off Market
221 Creekside Dr, Saint Augustine, FL 32086
0.07
$507,900
3
2
2,300
Off Market
211 Creekside Dr, Saint Augustine, FL 32086
0.08
$402,600
3
2
1,894
Off Market
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
0.08
-
-
-
-
Off Market
241 Creekside Dr, Audubon Park, FL 32086
0.09
$751,700
3
3
3,206
Off Market
201 Creekside Dr, Saint Augustine, FL 32086
0.09
$498,400
3
2
2,117
Off Market
115 Allgood Cir, Saint Augustine, FL 32086
0.10
-
-
-
-
Off Market
120 Allgood Cir, Saint Augustine, FL 32086
0.10
-
-
-
-
Off Market
191 Creekside Dr, Saint Augustine, FL 32086
0.10
$657,300
4
3
3,069
Off Market

Local Information

  • Map ViewExplore the area around 261 Rolling Oaks Rd.
  • Schools1 Preschool School1 Elementary School2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1988
0.6 acre lot
2,787 sqft
$224/sqft
Garage

About this House

What's unique:Fully furnishedAutomatic doorsGas heatGround poolCircular drivewayEat in kitchen nook
Beautiful 4 bedroom 3 bath furnished home located in Osceola Point in St. Johns County. New Pergo floors in living room, dining room, upstairs and 3 bedrooms. Large family room with fireplace and french doors that lead out to the screened lanai with in ground pool. Kitchen with breakfast area has new stainless steel appliances, gas stove and solid surface counter tops. Sep dining room for entertaining. Master bedroom located downstairs with walk-in closet. Master bath has his/her vanities and walk in shower. Rent includes pool care and lawn care. Property is owner managed. Small dog ok with approval, no cats.
261 Rolling Oaks Rd, Saint Augustine, FL 32086 is a 4 bedroom, 3 bathroom, 2,787 sqft single-family home built in 1988. It last sold for $285,910 on Mar 27, 2020. More recently, it was listed as a rental in October 2023 with an asking price of $3,250 per month. That rental listing was removed on December 23, 2023. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $625,400, with a rent estimate of $3,185/month.

Home Details for 261 Rolling Oaks Rd

Interior Features

Heating & Cooling
Heating: Forced Air, ElectricAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1.5Floors: Tile, Hardwood
Interior Details
Additional StorageTypes of Rooms: Walk In Closet, Dining RoomStorage
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: CompositionExterior: Wood, BrickFoundation Type: ConcretePorch
Pool
Pool
Parking & Garage
GarageParking: None, Garage

Property Information

Year Built
Year Built: 1988Year Updated: 1988
Property Type / Style
Property Type: Single Family HomeArchitecture: Contemporary

Community

Units in Building: 1

Lot Information

Lot Area: 0.60 acres

Price and Tax history

DateEventPrice
Dec 23, 2023
Source: Zillow Rentals
ListingRemoved
Nov 24, 2023
Source: Zillow Rentals
PriceChange
$3,150
Price decreased by 3%
Oct 21, 2023
Source: Zillow Rentals
Listed For Rent
$3,250
Aug 6, 2020
Source: Agent Provided
ListingRemoved
$2,900
Jul 23, 2020
Source: Agent Provided
PriceChange
$2,900
Price decreased by 9%

Market trends in Saint Augustine

Last updated September 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$434K
$5KMoM
Sale-to-List Price
97.6%
0.1%MoM
Price per sq ft
$227
$1MoM
Available listings
1697
39MoM
Sourced by Trulia Market Trends

Around this home

What Locals Say about Saint Augustine

This October

Trick-or-Treat Score

Built from what locals say about this neighborhood.
  • 79% say there's holiday spirit
  • 63% say there are sidewalks
  • 60% say neighbors are friendly
Trulia Trick or TreatStart Ghost Hunt
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
    Flag
  • 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
    Flag
  • 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 261 Rolling Oaks Rd

  • What is 261 Rolling Oaks Rd estimated to be worth?
    Trulia's estimated value for 261 Rolling Oaks Rd in Saint Augustine, FL is $625,400.
  • What is the price history for 261 Rolling Oaks Rd?
    261 Rolling Oaks Rd in Saint Augustine, FL last sold for $285,910 in March 2020.
  • 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 $434K. That is up $5K from the prior month.
  • Does 261 Rolling Oaks Rd have air conditioning?
    Yes, 261 Rolling Oaks Rd in Saint Augustine, FL has air conditioning.
  • Does 261 Rolling Oaks Rd have a pool?
    Yes, 261 Rolling Oaks Rd in Saint Augustine, FL has a pool.

Explore by feature - Pet Friendly

311 pet-friendly rentals in Saint Augustine, FL

Explore by feature - Garage

269 rentals with a garage in Saint Augustine, FL

Explore by feature - Air Conditioning

425 rentals with air conditioning in Saint Augustine, FL

Explore by feature - Pool

232 homes with a pool in Saint Augustine, FL

Explore by feature - Washer/dryer

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

Explore by feature - Outdoor Space

107 rentals with an outdoor space in Saint Augustine, FL

Apartments for Rent

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Off Market Homes Near 261 Rolling Oaks Rd

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