259 WINDSWEPT Way, Saint Augustine, FL 32092
Property image
Property image
FOR SALE
3D VIEW

259 WINDSWEPT Way
Saint Augustine, FL 32092

  • 3 Beds
  • 2.5 Baths
  • 2,293 sqft

$500,000

Original price: $515,000
Est. Mortgage $3,182/mo*
Get Pre-Qualified

$500,000

Original price: $515,000
Est. Mortgage $3,182/mo*
Get Pre-Qualified
3 Beds
2.5 Baths
2,293 sqft

Home Highlights

Parking
Garage
Outdoor
Porch
Climate Control
Heating & Cooling
HOA
$20/Monthly
Price/Sqft
$218
Listed
76 days ago

Local Information

  • Map ViewExplore the area around 259 WINDSWEPT Way.
-- mins to
Commute Destination

About this House

Major Price Improvement!

Preserve Views + Resort Style Amenities
Welcome to this beautifully maintained two-story home built in 2022 by David Weekley. Perfectly situated on a private preserve lot for added peace and natural views, but also a beautiful pond view out front. Offering 3 bedrooms plus an enclosed flex space, 2.5 bathrooms, and 2,293 square feet.

The open-concept main floor is ideal for both entertaining and daily living, featuring durable tile flooring and seamless flow between the living, dining, and kitchen areas.

The gourmet kitchen includes 42' cabinets, gas stove, quartz countertops and walk-in pantry. And tons of natural light pouring in from every side.

The versatile enclosed flex space provides the perfect option for a home office, playroom, or additional guest area.

Step outside to enjoy the extended screened-in lanai, where you can unwind while overlooking the tranquil preserve--no rear neighbors and plenty of privacy. Located in the highly sought-after Shearwater community, residents enjoy an unmatched lifestyle with resort-style amenities including a lagoon-style pool with a lazy river, multi-story water slide, state-of-the-art fitness lodge, tennis courts, kayak launch, and miles of scenic walking and biking trails. The community also features top-rated schools and a full calendar of events, creating a true neighborhood feel.

Conveniently located just a short drive to shopping, dining, and the historic charm of St. Augustine, as well as easy access to Jacksonville, this home offers the perfect blend of modern living and resort-style convenience.

Some photos have been virtually enhanced to illustrate home's potential, including cosmetic paint and fixtures. No structural features or room dimensions have been altered.

Home Details for 259 WINDSWEPT Way

Active Status

MLS Status: Active

Interior Features

Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 2293 Square Feet
Appliances & Utilities
Utilities: Electricity Connected, Natural Gas Connected, Water ConnectedAppliances: Dishwasher, Dryer, Gas Oven, Gas Range, Microwave, Refrigerator, WasherDishwasherDryerMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: CentralHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central
Fireplace & Spa
Spa: Community
Windows, Doors, Floors & Walls
Flooring: Carpet, Tile
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoFloors: Carpet, Tile
View
Has a ViewView: Trees/Woods
Security
Security: Smoke Detector(s)

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Covered, Front Porch, ScreenedOther Structures: Tennis Court(s)
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageNo Attached GarageParking Spaces: 2Parking: Garage
Frontage
Road Frontage: Private RoadRoad Surface Type: AsphaltNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Days on Market

Days on Market: 76

Property Information

Year Built
Year Built: 2022
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Craftsman
Building
Construction Materials: FrameNot a New ConstructionNot Attached Property
Property Information
Condition: Updated/RemodeledParcel Number: 0100160420

Price & Status

Price
List Price: $500,000Price Per Sqft: $218
Status Change & Dates
Possession Timing: Close Of Escrow

Location

Direction & Address
City: St. AugustineCommunity: Shearwater
School Information
Elementary School: Trout Creek AcademyJr High / Middle School: Trout Creek AcademyHigh School: Beachside

Agent Information

Listing Agent
Listing ID: 2147669

Community

Not Senior Community

HOA

Has an HOAHOA Fee: $236/Annually

Lot Information

Lot Area: 4791.6 sqft

Offer

Listing Terms: Cash, Conventional, FHA, VA Loan

Miscellaneous

Mls Number: 2147669

Additional Information

HOA Amenities: Pool,Barbecue,Children's Pool,Clubhouse,Dog Park,Fitness Center,Jogging Path,Maintenance Grounds,Management - Full Time,Park,Playground,Tennis Court(s)
Last check for updates: about 4 hours ago
Listing courtesy of JULIE KILKER, (405) 612-1435
HERRON REAL ESTATE LLC, (904) 729-4313
Source: realMLS, MLS#2147669
Also Listed on realMLS.

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

Price and Tax history

DateEventPrice
Aug 11, 2026
Source: Zillow Rentals
Listed For Rent
$3,000
Jul 2, 2026
Source: realMLS #2147669
PriceChange
$500,000
Price decreased by 3%
May 29, 2026
Source: realMLS #2147669
Listed For Sale
$515,000
Jul 18, 2022
Source: N/A
Sold
$534,800

Similar Homes You May Like

Skip to last item
Skip to first item

New Listings near 259 WINDSWEPT Way

Skip to last item
Skip to first item

Home Value

Trulia Estimate
$493K
Since last month
Decreased$14K (-2.8%)
Since last year
Decreased$38K (-7.1%)
Since last sale
Decreased$42K (-7.8%)
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 decreased by -8% in the last 10 years
MonthEstimated value
2026
August 2026$493K
July 2026$491K
June 2026$507K
May 2026$514K
April 2026$512K
March 2026$510K
February 2026$516K
January 2026$507K
2025
2024
2023

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
237 WINDSWEPT Way, Saint Augustine, FL
0.02
Single-Family Home
$420,000
02/13/26
3
2
1,790
149 WINDSWEPT Way, Saint Augustine, FL
0.12
Single-Family Home
$508,000
04/28/26
4
2.5
2,342
251 WINDSWEPT Way, Saint Augustine, FL
0.01
Single-Family Home
$340,000
04/17/26
3
2
1,790
163 WINDSWEPT Way, Saint Augustine, FL
0.10
Single-Family Home
$580,000
09/17/25
4
2.5
2,342
111 WINDSWEPT Way, Saint Augustine, FL
0.15
Single-Family Home
$455,000
02/20/26
4
2.5
2,319
383 WINDSWEPT Way, Saint Augustine, FL
0.12
Single-Family Home
$375,000
06/29/26
3
2
1,790
26 GILCHRIST Way, Saint Augustine, FL
0.15
Single-Family Home
$390,000
03/04/26
3
2
1,800
56 GILCHRIST Way, Saint Augustine, FL
0.16
Single-Family Home
$390,000
02/27/26
3
2
1,752
48 GILCHRIST Way, Augustine, FL
0.16
Single-Family Home
$392,000
09/15/25
3
2
1,675

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
267 WINDSWEPT Way, Saint Augustine, FL 32092
0.01
$554,700
4
2.5
2,340
Off Market
251 WINDSWEPT Way, Saint Augustine, FL 32092
0.01
$340,000
3
2
1,790
Recently Sold
40 SAMANTHA, Saint Augustine, FL 32092
0.06
$334,100
3
2.5
1,799
Off Market
237 WINDSWEPT Way, Saint Augustine, FL 32092
0.02
$420,000
3
2
1,790
Recently Sold
24 CRESCENDO Avenue, Saint Augustine, FL 32092
0.07
$507,200
4
3
2,326
Off Market
205 WINDSWEPT Way, Saint Augustine, FL 32092
0.05
$434,600
3
2
1,804
Off Market
186 LADSON Court, Saint Augustine, FL 32092
0.10
$439,000
3
2
1,808
Off Market
383 WINDSWEPT Way, Saint Augustine, FL 32092
0.12
$375,000
3
2
1,790
Recently Sold
21 YARDLEY Court, Augustine, FL 32092
0.11
$580,000
4
3
2,461
For Sale
175 WINDSWEPT Way, Saint Augustine, FL 32092
0.08
$456,900
3
2
1,942
Off Market
142 GOODHOPE Court, Saint Augustine, FL 32092
0.10
$500,000
4
3
2,183
Off Market

Around this home

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 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
    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
  • 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 259 WINDSWEPT Way

  • What is the estimated monthly payment for 259 WINDSWEPT Way?
    Based on a $500,000 list price with 20% down at today's rates, the estimated monthly payment for 259 WINDSWEPT Way in Saint Augustine, FL is approximately $3,217 (about $2,596 principal & interest, $546 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • How does the list price for 259 WINDSWEPT Way compare to homes in Saint Augustine?
    259 WINDSWEPT Way in Saint Augustine, FL is listed at $500,000, about 16% above the $432K median sale price in Saint Augustine.
  • What do residents say about Saint Augustine?
    Residents describe Saint Augustine, FL as dog-friendly, well-kept, and quiet. Most residents say you need a car. See homes for sale in Saint Augustine, FL.
  • What are the closest schools to 259 WINDSWEPT Way?
    The closest schools to 259 WINDSWEPT Way in Saint Augustine, FL are Beachside High School (Middle, rated 7/10), Trout Creek Academy (Elementary/Middle, rated 10/10).
  • Does 259 WINDSWEPT Way have air conditioning?
    Yes, 259 WINDSWEPT Way in Saint Augustine, FL has air conditioning.
  • Does 259 WINDSWEPT Way have a pool?
    Yes, 259 WINDSWEPT Way in Saint Augustine, FL has a pool.
JULIE KILKER, HERRON REAL ESTATE LLC, (904) 729-4313
Agent Phone: (405) 612-1435
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.
259 WINDSWEPT Way, Saint Augustine, FL 32092 is a 3 bedroom, 3 bathroom, 2,293 sqft single-family home built in 2022. This property is currently available for sale and was listed by realMLS on May 29, 2026. The MLS # for this home is MLS# 2147669.