5339 Overbrook Dr, Milton, FL 32570
Property image
Property image
OFF MARKET

$197,600

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,051 sqft

5339 Overbrook Dr, Milton, FL 32570

Est. Refi. Payment $1,325/mo*
Refinance Your Home
Currently Off Market - Sold Feb 21, 2020 for $124,000

Home Value

Trulia Estimate
$198K
Since last month
Decreased$2K (-1%)
Since last year
Increased$5K (+2.5%)
Since last sale
Increased$72K (+58.1%)
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 +32% in the last 10 years
MonthEstimated value
2026
September 2026$196K
August 2026$197K
July 2026$198K
June 2026$201K
May 2026$200K
April 2026$198K
March 2026$198K
February 2026$191K
January 2026$185K
2025
2024
2023
2022
2021

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
5334 Overbrook Dr, Milton, FL
0.03
Single-Family Home
$215,000
03/06/26
3
2
1,274
5327 Overbrook Dr, Milton, FL
0.03
Single-Family Home
$210,000
05/18/26
3
2
1,086
5365 Overbrook Dr, Milton, FL
0.04
Single-Family Home
$179,000
12/10/25
3
2
1,240
5398 Ticonderoga St, Milton, FL
0.28
Single-Family Home
$150,000
01/23/26
3
2
1,118
5326 Ticonderoga St, Milton, FL
0.27
Single-Family Home
$150,000
04/14/26
3
2
1,638
5419 Westwood Dr, Milton, FL
0.27
Single-Family Home
$100,000
12/08/25
3
2
1,582
6509 Lakeshore Dr, Milton, FL
0.31
Single-Family Home
$185,000
12/30/25
3
2
1,500
6328 Shady Ln, Milton, FL
0.23
Single-Family Home
$64,050
09/17/25
3
2
1,748
6552 College Dr, Milton, FL
0.60
Single-Family Home
$125,000
03/10/26
3
1.5
1,125
6503 College Dr, Milton, FL
0.49
Single-Family Home
$205,000
02/13/26
3
2
1,215

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
5335 Overbrook Dr, Milton, FL 32570
0.01
$221,200
3
2
1,274
Off Market
5334 Overbrook Dr, Milton, FL 32570
0.03
$215,000
3
2
1,274
Recently Sold
5327 Overbrook Dr, Milton, FL 32570
0.03
$210,000
3
2
1,086
Recently Sold
5365 Overbrook Dr, Milton, FL 32570
0.04
$179,000
3
2
1,240
Recently Sold
5355 Saratoga Ave, Milton, FL 32570
0.07
$240,000
3
2
1,248
For Sale
5310 Overbrook Dr, Milton, FL 32570
0.08
$228,000
3
2
1,197
Off Market
5301 Overbrook Dr, Milton, FL 32570
0.09
$226,800
3
2
1,200
Off Market
6376 Sunnyside Dr, Milton, FL 32570
0.09
$227,100
3
2
1,248
Off Market
5393 Overbrook Dr, Milton, FL 32570
0.11
-
-
-
-
Off Market
5289 Overbrook Dr, Milton, FL 32570
0.11
$212,700
3
2
1,100
Off Market
6365 Park Ave, Milton, FL 32570
0.12
$184,500
3
2
1,240
Off Market
6352 Sunnyside Dr, Milton, FL 32570
0.12
$225,900
3
2
1,392
Off Market

Local Information

  • Map ViewExplore the area around 5339 Overbrook Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1999
1,051 sqft
$188/sqft

About this House

Well maintained 3 Bedroom/2 Bath home for sale in the heart of Milton. This home features a split floor plan, freshly painted walls, new carpet in all bedrooms, wood laminate flooring in the living room, tiled wet areas, a single car garage and much more. The kitchen features oak cabinets, dishwasher, oven, refrigerator a built in microwave. The master suite features a walk in closet, and a garden tub. Both the HVAC unit and water were replaced in 2018. The manicured yard boast a sprinkler system, open patio in the back, storage shed, and is lined with well established crepe myrtles. This home is located on a corner lot and is just minutes from NAS Whiting Field, Schools, Shopping, Restaurants and Historic Downtown Milton. This one will not last long, call to set up your showing today!
5339 Overbrook Dr, Milton, FL 32570 is a 3 bedroom, 2 bathroom, 1,051 sqft single-family home built in 1999. It last sold for $124,000 on Feb 21, 2020. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $197,600, with a rent estimate of $1,579/month.

Home Details for 5339 Overbrook Dr

Interior Features

Heating & Cooling
Heating: Forced Air, ElectricAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Carpet, Linoleum Vinyl
Interior Details
Types of Rooms: Walk In Closet, Dining RoomCeiling Fan
Appliances & Utilities
DishwasherMicrowaveRefrigerator

Exterior Features

Exterior Home Features
Roof: Shake ShingleExterior: VinylFoundation Type: MasonryPatioPorch
Parking & Garage
Parking Space: 1

Property Information

Year Built
Year Built: 1999
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 7100 sqft

Price and Tax history

DateEventPrice
Feb 21, 2020
Source: PAR #565888
Sold
$124,000
Nov 18, 2003
Source: N/A
Sold
$81,300

Market trends in Milton

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$297K
$13.08KMoM
Sale-to-List Price
99.1%
0.2%MoM
Price per sq ft
$175
$1MoM
Available listings
335
17MoM

Around this home

What Locals Say about Milton

At least 264 Trulia users voted on each feature.

  • 91 % Say parking is easy

  • 91 % Say car is needed

  • 85 % Say yards are well-kept

  • 80 % Say it's dog friendly

  • 77 % Say there's holiday spirit

  • 71 % Say it's quiet

  • 65 % Say kids play outside

  • 61 % Say people would walk alone at night

  • 55 % Say neighbors are friendly

  • 49 % Say they plan to stay for at least 5 years

  • 47 % Say there's wildlife

  • 33 % Say streets are well-lit

  • 25 % Say it's walkable to grocery stores

  • 24 % Say there are sidewalks

  • 23 % Say there are community events

  • 16 % Say it's walkable to restaurants

Sourced by Trulia users. Learn more about our methodology.
  • J4vjdh42yc
    "Clean river to hike and let your pup swim in. Nice hiking places. Quiet side roads. Large lots. Good veterinary services. Plentiful pet supply outlets. Large dog park. "
    0
    Flag
  • Pammybarry
    "I would love to see a dog park or walking trail. Sidewalks would have been nice. Speed bump on some of the most traveled roads ."
    0
    Flag
  • Dalena Simmons
    "Trick or treat the streets We have all kinds of things to do near by. I live more in the country part of Milton fl."
    0
    Flag
  • Boyd L.
    "Dog owners are very responsible and take care of their dogs. It’s Very pet friendly neighborhood. There are dog parks in the neighborhood. Restaurants are dog friendly too. "
    1
    Flag
  • Stevenrasberryte
    "Great area! Very homey, perfect for families! Very military friendly! Close to beautiful beaches!!!!"
    4
    Flag
  • Carrie H.
    "Our HOA is community-oriented. It hosts community beautification days, Christmas parties, and fall festivities. "
    0
    Flag
  • Caitfranko
    "It’s safe. We have yard sales frequently. Neighbors are friendly. Kid/family friendly. "
    0
    Flag
  • Rachelnicole123
    "There’s many families in this area. It has great schools, multiple grocery stores, plenty fast food, & an Pensacola Beach is less than an hour away!! "
    0
    Flag
  • Ladwanya H.
    "There could be more for the kids to do around town, but there’s lots of parks,beaches and places to eat ."
    0
    Flag
  • Chctc0122
    "Nice people and a nice community. We have great local businesses here with unique finds. I was raised here and moved away for 15 years. Realized I miss the small town feel and the folks here."
    0
    Flag
  • Shillabrand
    "Dogs aren't roaming the neighborhood. There is a leash law. The yards are an acre each and there is plenty of room for dogs to play. Great neighborhood to walk your dogs."
    0
    Flag
  • Thedraiss5
    "Bands on the Blackwater and something down town almost every weekend................................................................. "
    0
    Flag
  • Pamela S.
    "Very few sidewalks in East Milton though there is a lot of greenspace and a cobblestone trail...biking and boating/ fishing is easy here "
    0
    Flag
  • Elaine B.
    "It's a quite neighborhood. Close to stores, Schools and Restaurants. Close to the Dr. office and the Hospital is not a mile away. "
    0
    Flag
  • Pamela S.
    "my neighborhood has great access to a major highway which is well-constructed and mail well-maintained also very well patrolled by state troopers. road ranger availability is good if you should have a problem. the only negative is that if there is a wreck time to clear the road seems extended and traffic backs up for miles and miles since exits are so far apart. "
    0
    Flag
  • Pamela S.
    "I've rented in this neighborhood long enough to know that I want to live here it feels very safe down home country charm close to the interstate with plenty of shopping nearby "
    0
    Flag
  • Zach M.
    "Trick or treating but overall the community is great can’t wait to see what the future has in store for us"
    0
    Flag
  • Tientien0026
    "Been here for two months; so far nothing seems alarming but wish it was a little more diverse in terms of people as well as food"
    0
    Flag
  • Angie P.
    "Milton is classic small town and a really nice place to live. I've been here my whole life and can't fathom leaving."
    0
    Flag
  • Katy F.
    "The schools are great, and the neighbors lookout for each other in Sundial Estates/Windsor Villas. The Bagdad post office is the friendliest, most helpful post office in the county. The are building a really nice park in phases at the Bagdad mill site (with separate boat and kayak launches, and a dock for fishing). Bagdad has the lowest taxes. "
    0
    Flag
  • Jennblane
    "There are no sidewalks around here- or even painted lanes. I miss biking and rollerblading. Definitely needs improvement."
    0
    Flag
  • Angie P.
    "We have a county Fair and tribal powwows, etc for family fun. Also, the City of Milton is only 3 minutes from my home and they have a lot of activities in the city, like gallery nights and Bands on Blackwater (the name of the local river)."
    0
    Flag
  • Bonnie L.
    "Not many inclusive events, most are religious based or geared towards those with certain lifestyles. Not very family friendly."
    0
    Flag
  • Zachary P.
    "lived here for 16 years and always thought it was a nice neighborhood. only complaint is the USPS is really crappy."
    0
    Flag
  • Ellemcalla
    "Yes I see people walking their dogs at all hours of the day. There are lots of dog owners in this neighborhood."
    0
    Flag
  • Trulia User
    "The dog owners in the neighborhood seem to be very considerate of their neighbors by keeping their animals under control and picking up after them."
    0
    Flag
  • Mike L.
    "I drive myself 6 miles to work and would likely not use public transportation if it became available."
    0
    Flag
  • Sere P. M. D.
    "Schools are excellent, very nice and quiet neighborhood, close to everything, highly recommended for all kind of families "
    0
    Flag
  • Panteratime
    "NAS Whiting Field Navy Base and the beautiful wilderness around. everyone has a dog it seems, so I love it around here."
    14
    Flag
  • Travis C
    "I work out of town so most of my commute consists of highway travel. Otherwise finding parking downtown is rarely an issue."
    0
    Flag
  • Trulia User
    "There's a lot of families in the area. People are friendly and the community is nice. We enjoy the events!"
    0
    Flag
  • Cynthia N. W.
    "Lots of military families with children in the neighborhood. And lots of dogs. It’s a good place for children. Must have a car to go anywhere or shop. "
    0
    Flag
  • Cynthia N. W.
    "Lots of school aged children & military families in my neighborhood. Very safe. Must drive everywhere. "
    0
    Flag
  • Candace P.
    "The school in the area are amazing. East Milton is very nice place to live. My neighborhood is very safe. "
    0
    Flag
  • Justine W.
    "I live in historic Downtown Milton and it’s a perfect little small town with everything in walking distance. Friendly community and loads of festivals, boardwalk with the Blackwater river, Imogene Theater with musicians, shows, comedians. Several popular restaurants, Blackwater Heritage Trail runs adjacent to my back yard and is about 9 miles long. Too many things to list. "
    3
    Flag
  • Heather d.
    "We just moved to town, but have met so many wonderful people. Looking forward to settling down in the community."
    4
    Flag
  • David H. G.
    "Love country living. Peaceful. Great schools. Very private"
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 5339 Overbrook Dr

  • What is 5339 Overbrook Dr estimated to be worth?
    Trulia's estimated value for 5339 Overbrook Dr in Milton, FL is $197,600.
  • What is the price history for 5339 Overbrook Dr?
    5339 Overbrook Dr in Milton, FL last sold for $124,000 in February 2020.
  • Is Milton a buyer's or seller's market?
    Milton is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Milton?
    The median sale price in Milton is $297K. That is up $13.08K from the prior month.
  • Does 5339 Overbrook Dr have air conditioning?
    Yes, 5339 Overbrook Dr in Milton, FL has air conditioning.
  • How big is the lot at 5339 Overbrook Dr?
    The lot at 5339 Overbrook Dr in Milton, FL is about 0.16 acres (7,100 sq ft).

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Off Market Homes Near 5339 Overbrook Dr

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