308 WINDING OAK Way, Saint Augustine, FL 32084
Property image
Property image
SOLD
DEC 10, 2025

308 WINDING OAK Way
Saint Augustine, FL 32084

  • 4 Beds
  • 2 Baths
  • 2,091 sqft (on 0.34 acres)

$370,000

Last Sold: Dec 10, 2025
8% below list $400K
$177/sqft
Est. Refi. Payment $2,358/mo*
Refinance Your Home

$370,000

Last Sold: Dec 10, 2025
8% below list $400K
$177/sqft
Est. Refi. Payment $2,358/mo*
Refinance Your Home
4 Beds
2 Baths
2,091 sqft
(on 0.34 acres)

Local Information

  • Map ViewExplore the area around 308 WINDING OAK Way.
  • Schools1 Preschool School1 Elementary School2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2008
Lot Size
0.34 acres
Living Area
2,091 sqft
Price/Sqft
$177/sqft
Parking
Garage
HOA
$92/Monthly

About this House

Price Reduction - Welcome home to 308 Winding Oak Way in St Augustine - One of the Largest lots in OLDE FLORIDA. - 4 bedroom 2 bath 3 car garage - Huge backyard - Schedule your shouwing today to view this beautiful home -
308 WINDING OAK Way, Saint Augustine, FL 32084 is a 4 bedroom, 2 bathroom, 2,091 sqft single-family home built in 2008. It last sold for $370,000 on Dec 10, 2025 (8% below the $400,000 asking price). It is currently off market. The Trulia Estimate is $372,700, with a rent estimate of $2,609/month.

Home Details for 308 WINDING OAK Way

Active Status

MLS Status: Closed

Interior Features

Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 2091 Square Feet
Appliances & Utilities
Utilities: Electricity Connected, Sewer Connected, Water ConnectedAppliances: Dishwasher, Dryer, Electric Oven, Electric Water Heater, Microwave, Refrigerator, WasherDishwasherDryerLaundry: In UnitMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Central,ElectricHas CoolingAir Conditioning: Central Air,ElectricHas HeatingHeating Fuel: Central
Windows, Doors, Floors & Walls
Flooring: Carpet, Tile
Levels, Entrance, & Accessibility
Stories: 1Levels: OneFloors: Carpet, Tile
View
No View
Security
Security: Smoke Detector(s)

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Rear Porch, ScreenedFencing: Back Yard, Wood
Parking & Garage
Number of Garage Spaces: 3Number of Covered Spaces: 3No CarportHas a GarageNo Attached GarageParking Spaces: 3Parking: Garage
Frontage
Road Surface Type: AsphaltNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Property Information

Year Built
Year Built: 2008
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Construction Materials: Composition Siding, Frame, StuccoNot a New ConstructionNot Attached Property
Property Information
Parcel Number: 0862220050

Price & Status

Price
List Price: $400,000Price Per Sqft: $177/sqft
Status Change & Dates
Off Market Date: Fri Oct 31 2025Possession Timing: Close Of Escrow

Location

Direction & Address
City: St. AugustineCommunity: Olde Florida

Building

Building Area
Building Area: 3187 Square Feet

Community

Not Senior Community

HOA

Has an HOAHOA Fee: $275/Quarterly

Lot Information

Lot Area: 0.34 acres

Offer

Listing Terms: Cash, Conventional, FHA, VA Loan

Miscellaneous

Mls Number: 2093796
Last check for updates: about 4 hours ago
Listed by JAMES H DIAMOND, (904) 463-8700
UNITED REAL ESTATE GALLERY, (904) 500-3948
Source: realMLS, MLS#2093796

Price History for 308 WINDING OAK Way

DatePriceEventSource
12/10/2025$370,000Sold
realMLS #2093796
10/16/2025$400,000PriceChange
realMLS #2093796
10/06/2025$430,000PriceChange
realMLS #2093796
10/01/2025$447,000PriceChange
realMLS #2093796
09/05/2025$460,000PriceChange
realMLS #2093796
08/13/2025$468,000PriceChange
realMLS #2093796
07/09/2025$472,500PriceChange
realMLS #2093796
06/19/2025$475,000Listed For SalerealMLS #2093796
08/25/2021$333,400Sold
N/A
01/22/2019$289,900Sold
N/A
01/04/2019$299,800PendingAgent Provided
10/05/2018$299,800Listed For SaleAgent Provided
10/16/2012$235,000Sold
N/A
06/06/2012$259,000Listed For SaleAgent Provided
06/04/2008$285,000Sold
N/A

Market trends in Saint Augustine

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$418K
$1.67KMoM
Sale-to-List Price
97.2%
0.1%MoM
Price per sq ft
$226
$2MoM
Available listings
1897
43MoM
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Property Tax and Assessment

Year2025
Tax$4,508
Assessment$347,424
Home facts updated by county records

Comparable Sales for 308 WINDING OAK Way

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
486 Hefferon Dr, Saint Augustine, FL
0.49
Single-Family Home
$401,000
03/20/26
4
2
2,050
266 Roaring Brook Dr, Saint Augustine, FL
0.30
Single-Family Home
$520,000
03/02/26
4
2
1,800
271 ROARING BROOK Drive, Saint Augustine, FL
0.31
Single-Family Home
$425,000
09/12/25
3
2
1,838
49 MISSION COVE Circle, Saint Augustine, FL
0.44
Single-Family Home
$362,000
05/29/26
4
2
2,126
1205 Wild Palm Ct, Saint Augustine, FL
0.64
Single-Family Home
$422,500
12/15/25
4
2
2,110
117 Mission Cove Cir, Saint Augustine, FL
0.40
Single-Family Home
$360,000
02/27/26
4
3
2,644
96 CYPRESS BLUFF Way, Saint Augustine, FL
0.35
Single-Family Home
$465,000
03/27/26
3
2
2,066
727 E Red House Branch Rd, Saint Augustine, FL
0.65
Single-Family Home
$444,000
09/12/25
4
2
2,006
367 MISSION TRACE Drive, Saint Augustine, FL
0.43
Single-Family Home
$540,000
06/10/26
3
2
1,906

Nearby homes

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Assigned Schools

These are the assigned schools for 308 WINDING OAK Way.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Saint Augustine

At least 669 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

  • 55 % 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
    "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
  • 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
  • Vicki.perry
    "Great for families. Palencia has an elementary school in the community. Lots of places to ride your bike and take walks too."
    4
    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

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Homes for sale near 308 WINDING OAK Way

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Off Market Homes Near 308 WINDING OAK Way

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IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed accurate by realMLS.