756 Crestwood Dr, Saint Augustine, FL 32086
Property image
Property image
SOLD
AUG 11, 2026

$339,900

Trulia Estimate
  • 2 Beds
  • 2 Baths
  • 1,592 sqft

756 Crestwood Dr, Saint Augustine, FL 32086

Est. Refi. Payment $2,253/mo*
Refinance Your Home
Currently Off Market - Sold Aug 11, 2026 for $339,900 (3% above list price)

Home Value

Trulia Estimate
$340K
Since last month
$100 (0%)
Since last year
Decreased$15K (-4.3%)
Since last sale
$100 (0%)
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 +66% in the last 10 years
MonthEstimated value
2026
September 2026$340K
August 2026$340K
July 2026$328K
June 2026$351K
May 2026$350K
April 2026$352K
March 2026$352K
February 2026$354K
January 2026$352K
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
1053 RIDGEWOOD Lane, Saint Augustine, FL
0.11
Single-Family Home
$342,900
04/10/26
2
2
1,620
708 CRESTWOOD DRIVE, Saint Augustine, FL
0.15
Single-Family Home
$345,000
09/03/26
2
2
1,791
808 CRESTWOOD Drive, Saint Augustine, FL
0.13
Single-Family Home
$365,500
12/01/25
2
2
1,912
573 Boxwood Pl, Saint Augustine, FL
0.20
Single-Family Home
$365,000
04/09/26
2
2
1,780
972 Ridgewood Ln, Saint Augustine, FL
0.13
Single-Family Home
$385,000
07/17/26
3
2
1,636
512 Boxwood Pl, Saint Augustine, FL
0.15
Single-Family Home
$345,000
10/10/25
2
2
1,613
737 Crestwood Dr, Saint Augustine, FL
0.05
Single-Family Home
$365,000
02/09/26
3
2
1,912
211 Deltona Blvd, Saint Augustine, FL
0.15
Single-Family Home
$377,500
05/29/26
3
2
1,577

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
737 Crestwood Dr, Saint Augustine, FL 32086
0.05
$365,000
3
2
1,912
Recently Sold
752 Crestwood Dr, Saint Augustine, FL 32086
0.01
$361,800
3
2
1,620
Off Market
757 Crestwood Dr, Saint Augustine, FL 32086
0.03
$416,800
2
2
1,912
Off Market
1073 Ridgewood Ln, Saint Augustine, FL 32086
0.06
$390,600
3
2
1,711
Off Market
948 Ridgewood Ln, Saint Augustine, FL 32086
0.08
$357,400
2
2
1,791
Off Market
1053 RIDGEWOOD Lane, Saint Augustine, FL 32086
0.11
$342,900
2
2
1,620
Recently Sold
717 Crestwood Dr, Saint Augustine, FL 32086
0.11
$410,200
3
2
1,740
Off Market
165 TOLEDO Street, Saint Augustine, FL 32086
0.08
$304,900
2
2
1,128
For Sale
945 RIDGEWOOD Lane, Saint Augustine, FL 32086
0.11
$321,400
2
2
1,908
Off Market
972 Ridgewood Ln, Saint Augustine, FL 32086
0.13
$385,000
3
2
1,636
Recently Sold
925 Ridgewood Ln, Saint Augustine, FL 32086
0.10
$368,800
2
2
1,636
Off Market

Local Information

  • Map ViewExplore the area around 756 Crestwood Dr.
  • Schools1 Preschool School1 Elementary School2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2006
1,592 sqft
$214/sqft
2 Car Garage
HOA $205/mo

About this House

What's unique:Gated entranceScreened lanaiDedicated officeGranite countertopsBright open floor planCommunity pool
LOW-MAINTENANCE LIVING IN THE GATED SOUTHWOOD COMMUNITY! Enjoy the comfort of a concrete block home with the convenience of lawn maintenance included, giving you more time to enjoy everything St. Augustine has to offer. Whether you're looking for a full-time residence, a seasonal retreat, or an easy lock-and-leave home, this one checks all the boxes. Offering 2 bedrooms, 2 bathrooms, plus a dedicated office that could easily serve as a third bedroom, this home features a bright, open floor plan with soaring ceilings, skylights, and large tile flooring throughout the main living areas. The living room flows seamlessly into the kitchen and dining area, creating an inviting space for everyday living. The kitchen is well-appointed with granite countertops, a tile backsplash, cherry wood cabinetry, and a casual dining area. The spacious owner's suite offers sliding glass doors leading to the sunroom, a walk-in closet, and a private bath with a double-sink vanity and a large walk-in shower. Just off the living area, the screened lanai provides the perfect place to enjoy your morning coffee or unwind in the evening. Recent updates include a newer roof, newer water heater, and new carpet in both bedrooms. Southwood offers NO CDD fees, low HOA fees ($205 monthly), a gated entrance, full-service lawn care including irrigation, and an impressive amenity package featuring a community pool, pickleball and tennis courts, a covered pavilion, and shuffleboard. Located just minutes from the beaches, shopping, restaurants, parks, top-rated St. Johns County schools, and historic downtown St. Augustine, this home offers the ideal combination of comfort, convenience, and low-maintenance living.
756 Crestwood Dr, Saint Augustine, FL 32086 is a 2 bedroom, 2 bathroom, 1,592 sqft single-family home built in 2006. It last sold for $339,900 on Aug 11, 2026 (3% above the $329,900 asking price). More recently, it was listed as a rental in February 2020 with an asking price of $1,595 per month. That rental listing was removed on March 28, 2020. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $339,900, with a rent estimate of $2,039/month.
Last check for updates: about 2 hours ago
Listed by Kevin Howard, (904) 669-1918
Endless Summer Realty
Bought with: Robert Sherno, (904) 501-1989, Coastal Realty Sales Division LLC
Source: St Augustine St Johns County BOR, MLS#263259

Home Details for 756 Crestwood Dr

Interior Features

Interior Details
Number of Rooms: 7Types of Rooms: Master Bedroom, Bedroom 2, Master Bathroom, Dining Room, Kitchen, Living Room, Office
Beds & Baths
Number of Bedrooms: 2Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 1592 Square Feet
Appliances & Utilities
Appliances: Dishwasher, Disposal, Dryer, Microwave, Range, Refrigerator, WasherDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Central,ElectricHas CoolingAir Conditioning: Central Air,ElectricHas HeatingHeating Fuel: Central
Windows, Doors, Floors & Walls
Window: Window TreatmentsFlooring: Carpet, Tile
Levels, Entrance, & Accessibility
Stories: 1Levels: SplitEntry Location: Ground LevelFloors: Carpet, Tile

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Screened PorchFoundation: SlabNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageNo Open ParkingParking Spaces: 2Parking: 2 Car Garage,Attached,Garage Door Opener
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer

Property Information

Year Built
Year Built: 2006
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: Patio Home, Single Family HomeArchitecture: Patio Home,Single Family Home
Building
Construction Materials: Block, StuccoNot a New Construction
Property Information
Parcel Number: 1817520740

Price & Status

Price
List Price: $329,900Price Per Sqft: $214/sqft
Status Change & Dates
Off Market Date: Wed Aug 05 2026

Active Status

MLS Status: Closed

Media

Location

Direction & Address
City: St AugustineCommunity: Southwood
School Information
Elementary School: W. D. HartleyJr High / Middle School: Gamble RogersHigh School: Pedro Menendez

Building

Building Area
Building Area: 1592 Square Feet

Community

Community Features: Gated, Tennis Court(s), HOANot Senior Community

HOA

HOA Fee Includes: HOA(Community Maintained, Management)Has an HOAHOA Fee: $205/Monthly

Lot Information

Lot Area: 4791.6 sqft

Offer

Listing Terms: Cash, Conventional, FHA, VA Loan

Miscellaneous

Mls Number: 263259

Additional Information

GatedTennis Court(s)HOA

Price and Tax history

DateEventPrice
Aug 11, 2026
Source: St Augustine St Johns County BOR #263259
Sold
$339,900
Jul 20, 2026
Source: realMLS #2155273
Pending
$329,900
Jul 14, 2026
Source: St Augustine St Johns County BOR #263259
Listed For Sale
$329,900
Jan 27, 2022
Source: realMLS #1148289
Sold
$345,000
Jan 24, 2022
Source: realMLS #1148289
Pending
$339,900

Market trends in Saint Augustine

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$429K
$2.5KMoM
Sale-to-List Price
97.4%
Price per sq ft
$228
$0MoM
Available listings
1730
61MoM

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 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
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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

LGBTQ Local Legal Protections

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. Information is deemed reliable but not guaranteed. © 2026 St Augustine & St. Johns County Board of REALTORS®. All rights reserved.

Frequently asked questions about 756 Crestwood Dr

  • What is 756 Crestwood Dr estimated to be worth?
    Trulia's estimated value for 756 Crestwood Dr in Saint Augustine, FL is $339,900.
  • What is the price history for 756 Crestwood Dr?
    756 Crestwood Dr in Saint Augustine, FL last sold for $339,900 in August 2026.
  • 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 $429K. That is down $2.5K from the prior month.
  • Does 756 Crestwood Dr have air conditioning?
    Yes, 756 Crestwood Dr in Saint Augustine, FL has air conditioning.
  • Does 756 Crestwood Dr have laundry facilities?
    Yes, 756 Crestwood Dr in Saint Augustine, FL has in-unit laundry.

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