259 Windswept Way, Saint Augustine, FL 32092
Property image
Property image
FOR RENT
3D VIEW
PET FRIENDLY

$2,950/mo

  • 3 Beds
  • 2.5 Baths
  • 2,293 sqft

259 Windswept Way, Saint Augustine, FL 32092

Cost and fees breakdown
Price may not include required fees and charges.

Home Highlights

Single-Family Home
Garage
Dogs & Cats Allowed
Dishwasher
Washer, Dryer
$2,950 deposit
Central Air

Local Information

  • Map ViewExplore the area around 259 Windswept Way.
  • Schools1 Elementary School2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

What's unique:Large islandEnclosed flex spaceQuartz countertopsGas rangeExtended screened-in lanaiOpen-concept floor plan
**AVAILABLE NOW**

** ON ALL APPROVED APPLICATIONS - WAIVED APPLICATION FEE AND LEASE ADMIN FEE**

Beautiful 3-bedroom, 2.5-bathroom home for rent in the highly desirable Shearwater community! Offering nearly 2,300 square feet of living space, this spacious two-story home features an open-concept floor plan with tile flooring throughout the main living areas. The gourmet kitchen boasts quartz countertops, 42-inch cabinetry, stainless steel appliances, a gas range, large island, and walk-in pantry. The kitchen opens seamlessly to the dining and living areas with tons of natural light. An enclosed flex space provides the perfect home office, playroom, or additional living area.

Upstairs you'll find the spacious primary suite along with two additional bedrooms. Enjoy the extended screened-in lanai overlooking a peaceful preserve with no rear neighbors! The home also includes a 2-car garage and washer and dryer. Shearwater offers incredible resort-style amenities including community pools, clubhouse, fitness center, playground, dog park, jogging paths, tennis courts, and more!

Pets are welcomed upon approval and with a pet fee.
Tenant handles lawn maintenance.

For a link to a walk-thru tour, please click below.

No co-signors or guarantors permitted.
We have a Strict NO Smoking or Vaping are permitted in or on the property.

Nest Finders will not lease sight unseen. Applicants must view property in person in order to lease it.

Screening includes a credit/criminal background check, income verification of 3x the monthly rent, and rental history verification.

Residents are enrolled in a required Resident Benefits Package ($42/month), including tenant liability insurance and resident services, billed in addition to rent.

This home participates in a required Group Rate Internet program providing 1 gig-speed internet at a discounted bulk rate of $65/month, billed separately from rent.

TENANT CHARGES:

- Application Fee = $80 per adult
- Lease Initiation Admin Fee = $150.00 after approval and upon signing
- Resident Benefits Package (RBP) = $42.00 per month (not optional)
- Security Deposit = 1-2 x the monthly Rent depending on property requirement and application score (fully refundable)
- Pet fees as listed (if applicable)
- 13 month lease term

PETS (if accepted on a property):

- $300-$500 Pet Fee per pet and additional pet rent per pet $30-$75/mo based on Pet screenings - Paw score.
- No resident or residents at any one premises shall at any one time own, harbor, or license more than TWO total animals in any combination
- Up to TWO PETS Maximum on approved properties
- The pet application fee is $20 for the first pet, $15 for each additional pet

TO APPLY:

- $80.00 per adult non refundable Application Fee PER adult to be paid at the time of application.
- Please Review application criteria and Deposit Info before applying
- All applicants must complete the pet screening whether or not you have a pet.- We process all applications, and the first application that completes all the paperwork requirements and criteria will be processed first.

Are you an Owner looking for a property management company?
Nest Finders Property Management
9889 Gate Pkwy N, #402
Jacksonville, FL 32246

AMENITIES:
* Shearwater Amenities

By submitting your information on this page you consent to being contacted by the Property Manager and RentEngine via SMS, phone, or email.
Contact this Building
(904) 560-6268

Details for 259 Windswept Way

Days on Market

Days on Market: 25 days on Trulia

Property Information

Year Built
Year Built: 2022
Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: 1 YearCats, small dogs allowedDeposit: $2,950

Interior Features

Appliances & Utilities
DishwasherDryerRefrigeratorWasher
Heating & Cooling
Air Conditioning
Levels, Entrance, & Accessibility
Floors: Tile

Exterior Features

Parking & Garage
GarageParking: Garage

Media

Lot Information

Lot Area: 4791.6 sqft

Policies and fees

Pet policy

Dogs
Allowed
  • Size allowed
    Small
  • Restrictions: None
Cats
Allowed
  • Size allowed
    n/a
  • Restrictions: None
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Rental Market Trends in Saint Augustine

Last updated Oct 2026
Trulia Rent Estimate$2,952/mo
Average rent
$2.4K
$50MoM
Available listings
653
View rental market trends in Saint Augustine, FL

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 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
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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
    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

Local Legal Protections

LGBTQ • Source of Income

Price and Tax history

DateEventPrice
Sep 8, 2026
Source: realMLS #2147669
ListingRemoved
$500,000
Aug 25, 2026
Source: Zillow Rentals
PriceChange
$2,950
Price decreased by 2%
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
Nest Finders Property Management
Phone Number: 904-560-6268

Frequently asked questions about 259 Windswept Way

  • What income do you need to rent 259 Windswept Way?
    Most landlords look for monthly gross income of about 3× rent, or roughly $105K per year to rent 259 Windswept Way in Saint Augustine, FL at $2,950/mo.
  • What is the pet policy at 259 Windswept Way?
    259 Windswept Way in Saint Augustine, FL allows cats and small dogs.
  • How does the rent for 259 Windswept Way compare to similar 3-bedroom houses in Saint Augustine?
    259 Windswept Way in Saint Augustine, FL rents about 20% above the area average for 3-bedroom houses in Saint Augustine ($2,450/mo).
  • 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 laundry facilities?
    Yes, 259 Windswept Way in Saint Augustine, FL has in-unit laundry.
  • How big is the lot at 259 Windswept Way?
    The lot at 259 Windswept Way in Saint Augustine, FL is about 0.11 acres (4,792 sq ft).

Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
$106,200 PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.

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259 Windswept Way, Saint Augustine, FL is a 3 bedroom, 3 bathroom, 2,293 sqft single-family home built in 2022. 259 Windswept Way was listed for rent for $2,950/month on Aug 11, 2026. This property is pet friendly.