808 CRESTWOOD Drive, Saint Augustine, FL 32086
Property image
Property image
SOLD
DEC 1, 2025

$370,300

Trulia Estimate
  • 2 Beds
  • 2 Baths
  • 1,912 sqft

808 CRESTWOOD Drive, Saint Augustine, FL 32086

Est. Refi. Payment $2,448/mo*
Refinance Your Home
Currently Off Market - Sold Dec 1, 2025 for $365,500 (4% below list price)

Home Value

Trulia Estimate
$370K
Since last month
Increased$700 (+0.2%)
Since last year
Increased$4K (+1.1%)
Since last sale
Increased$6K (+1.6%)
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 +64% in the last 10 years
MonthEstimated value
2026
September 2026$371K
August 2026$371K
July 2026$368K
June 2026$367K
May 2026$368K
April 2026$364K
March 2026$360K
February 2026$362K
January 2026$364K
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
756 Crestwood Dr, Saint Augustine, FL
0.13
Single-Family Home
$339,900
08/11/26
2
2
1,592
708 CRESTWOOD DRIVE, Saint Augustine, FL
0.23
Single-Family Home
$345,000
09/03/26
2
2
1,791
1053 RIDGEWOOD Lane, Saint Augustine, FL
0.24
Single-Family Home
$342,900
04/10/26
2
2
1,620
617 Knollwood Ln, Saint Augustine, FL
0.08
Single-Family Home
$415,000
05/18/26
3
2
1,933
573 Boxwood Pl, Saint Augustine, FL
0.28
Single-Family Home
$365,000
04/09/26
2
2
1,780
737 Crestwood Dr, Saint Augustine, FL
0.16
Single-Family Home
$365,000
02/09/26
3
2
1,912
512 Boxwood Pl, Saint Augustine, FL
0.16
Single-Family Home
$345,000
10/10/25
2
2
1,613
984 Ridgewood Ln, Saint Augustine, FL
0.27
Single-Family Home
$360,000
01/28/26
3
2
1,888
972 Ridgewood Ln, Saint Augustine, FL
0.24
Single-Family Home
$385,000
07/17/26
3
2
1,636

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
817 Crestwood Dr, Saint Augustine, FL 32086
0.03
$372,400
2
2
1,931
Off Market
629 KNOLLWOOD Lane, Saint Augustine, FL 32086
0.06
$399,000
3
2
1,772
For Sale
621 Knollwood Ln, Saint Augustine, FL 32086
0.07
$388,600
3
2
1,656
Off Market
617 Knollwood Ln, Saint Augustine, FL 32086
0.08
$415,000
3
2
1,933
Recently Sold
921 Ridgewood Ln, Saint Augustine, FL 32086
0.11
$347,900
2
2
1,613
Off Market
925 Ridgewood Ln, Saint Augustine, FL 32086
0.12
$368,800
2
2
1,636
Off Market
844 Crestwood Dr, Saint Augustine, FL 32086
0.09
$377,300
2
2
1,912
Off Market
849 Crestwood Dr, Saint Augustine, FL 32086
0.10
$399,900
3
2
1,699
For Sale
757 Crestwood Dr, Saint Augustine, FL 32086
0.13
$416,800
2
2
1,912
Off Market
756 Crestwood Dr, Saint Augustine, FL 32086
0.13
$339,900
2
2
1,592
Recently Sold
752 Crestwood Dr, Saint Augustine, FL 32086
0.13
$361,800
3
2
1,620
Off Market

Local Information

  • Map ViewExplore the area around 808 CRESTWOOD Drive.
  • Schools1 Preschool School1 Elementary School2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2004
1,912 sqft
$191/sqft
2 Car Garage
HOA $205/mo

About this House

What's unique:Gated communityScreened lanaiSplit-bedroom layoutLarge foyerLots of storage spaceEat-in area
Tucked inside the gated community of Southwood, where amenities like a pool, tennis courts, and shuffleboard is just a short walk away, you'll find this beautifully designed 2-bedroom, 2-bath home with a bonus room and the largest floor plan in the neighborhood, boasting 1,912 SQFT. As you enter the home you're greeted by a large foyer, soaring 14-ft ceilings, eye-catching archways, and a spacious open layout. The large living room will accommodate all your oversized furniture and décor and features a double track12-ft sliding glass door that opens to the screened lanai, which is perfect for indoor and outdoor living. The spacious kitchen offers lots of storage space for all your cooking tools and additional appliances, an eat-in area, a nice size pantry closet, an 11-ft breakfast bar, and new dishwasher. The split-bedroom layout gives added privacy, and the oversized primary suite includes a tray ceiling, lots of natural light, a (10' x 5.10'') walk-in closet , a roomy on suite with dual vanities, separate shower, and a garden tub to relax and have some me time. If any of this sounds like something that interests you, make a call and schedule a showing. And for peace of mind, the roof is approx. 4-years-old and HVAC system is approx. 6-year-old.
808 CRESTWOOD Drive, Saint Augustine, FL 32086 is a 2 bedroom, 2 bathroom, 1,912 sqft single-family home built in 2004. It last sold for $365,500 on Dec 1, 2025 (4% below the $379,900 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $370,300, with a rent estimate of $2,263/month.
Last check for updates: about 11 hours ago
Listed by Todd Beals, (904) 588-2083
FLORIDA HOMES REALTY & MTG LLC, (904) 996-9115
Bought with: STEVEN WALT, (904) 823-3456, GREAT EXPECTATIONS REALTY, (904) 823-3456
Source: realMLS, MLS#2098603

Home Details for 808 CRESTWOOD Drive

Active Status

MLS Status: Closed

Interior Features

Interior Details
Number of Rooms: 6Types of Rooms: Master Bedroom, Bedroom 2, Bonus Room, Dining Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 2Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 1912 Square Feet
Appliances & Utilities
Utilities: Cable Connected, Electricity Connected, Sewer Connected, Water ConnectedAppliances: Dishwasher, Disposal, Electric Range, Ice Maker, Microwave, Refrigerator, Washer/Dryer StackedDishwasherDisposalLaundry: Electric Dryer HookupMicrowaveRefrigerator
Heating & Cooling
Heating: Central,ElectricHas CoolingAir Conditioning: Central Air,ElectricHas HeatingHeating Fuel: Central
Windows, Doors, Floors & Walls
Flooring: Carpet, Tile
Levels, Entrance, & Accessibility
Stories: 1Floors: Carpet, Tile
View
Has a ViewView: Trees/Woods
Security
Security: Smoke Detector(s)

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Rear Porch, ScreenedFencing: Other
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageParking Spaces: 2Parking: Attached,Garage,Garage Door Opener
Frontage
Road Surface Type: AsphaltNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Property Information

Year Built
Year Built: 2004
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Ranch
Building
Construction Materials: Block, StuccoNot a New ConstructionAttached To Another Structure
Property Information
Parcel Number: 1817520870

Price & Status

Price
List Price: $379,900Price Per Sqft: $191/sqft
Status Change & Dates
Off Market Date: Sat Oct 25 2025Possession Timing: Close Of Escrow

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: 2559 Square Feet

Community

Not Senior Community

HOA

HOA Fee Includes: Maintenance GroundsHOA Name: SouthwoodHas an HOAHOA Fee: $205/Monthly

Lot Information

Lot Area: 5227.2 sqft

Offer

Listing Terms: Cash, Conventional, FHA, VA Loan

Miscellaneous

Mls Number: 2098603

Additional Information

HOA Amenities: Pool,Gated,Security,Tennis Court(s)

Price and Tax history

DateEventPrice
Dec 1, 2025
Source: realMLS #2098603
Sold
$365,500
Oct 25, 2025
Source: realMLS #2098603
Pending
$379,900
Aug 7, 2025
Source: realMLS #2098603
PriceChange
$379,900
Price decreased by 3%
Jul 15, 2025
Source: realMLS #2098603
Listed For Sale
$389,900

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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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. Data is deemed reliable but is not guaranteed accurate by realMLS.

Frequently asked questions about 808 CRESTWOOD Drive

  • What is 808 CRESTWOOD Drive estimated to be worth?
    Trulia's estimated value for 808 CRESTWOOD Drive in Saint Augustine, FL is $370,300.
  • What is the price history for 808 CRESTWOOD Drive?
    808 CRESTWOOD Drive in Saint Augustine, FL last sold for $365,500 in December 2025.
  • 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 808 CRESTWOOD Drive have air conditioning?
    Yes, 808 CRESTWOOD Drive in Saint Augustine, FL has air conditioning.
  • Does 808 CRESTWOOD Drive have a pool?
    Yes, 808 CRESTWOOD Drive in Saint Augustine, FL has a pool.

Explore by feature - Pet Friendly

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