4239 Crosswinds Dr, Milton, FL 32583
OFF MARKET

$301,600

Trulia Estimate
  • 4 Beds
  • 2 Baths
  • 2,085 sqft (on 0.26 acres)

4239 Crosswinds Dr, Milton, FL 32583

Est. Refi. Payment $1,933/mo*
Refinance Your Home
Currently Off Market - Sold Aug 20, 2010 for $143,800

Home Value

Trulia Estimate
$302K
Since last month
Increased$500 (+0.2%)
Since last year
Increased$2K (+0.8%)
Since last sale
Increased$158K (+109.6%)
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 +85% in the last 10 years
MonthEstimated value
2026
August 2026$301K
August 2026$301K
July 2026$301K
June 2026$303K
May 2026$305K
April 2026$304K
March 2026$304K
February 2026$299K
January 2026$290K
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
4263 Crosswinds Dr, Milton, FL
0.09
Single-Family Home
$310,000
10/21/25
4
3
2,636
5662 Pin Oak Ave, Milton, FL
0.36
Single-Family Home
$272,000
10/02/25
4
2
1,950
4331 Crosswinds Dr, Milton, FL
0.24
Single-Family Home
$285,000
04/28/26
3
2
1,515
5663 Sweet Birch Ln, Milton, FL
0.38
Single-Family Home
$267,000
04/09/26
4
2
2,557
5644 Sweet Birch Ln, Milton, FL
0.42
Single-Family Home
$390,000
08/05/26
4
2
2,317
4490 Oak Ln, Milton, FL
0.27
Single-Family Home
$229,400
07/13/26
3
2
1,178
4411 Oak Ln, Milton, FL
0.33
Single-Family Home
$255,000
07/13/26
3
2
1,315
5650 Sweet Birch Ln, Milton, FL
0.40
Single-Family Home
$365,000
09/10/25
4
2
2,291
4482 Oak Ln, Milton, FL
0.29
Single-Family Home
$230,000
05/26/26
3
2
1,178
5953 Fairlands Rd, Milton, FL
0.41
Single-Family Home
$215,000
06/09/26
3
2
1,358

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
4235 Crosswinds Dr, Milton, FL 32583
0.02
$295,800
4
2
1,749
Off Market
4263 Crosswinds Dr, Milton, FL 32583
0.09
$316,900
4
3
2,636
Off Market
5818 Quietwood Dr, Milton, FL 32583
0.06
$311,200
3
2
1,552
Off Market
5730 Ridge Ave, Milton, FL 32583
0.16
$230,600
3
2
1,120
Off Market
5725 Ridge Ave, Milton, FL 32583
0.17
$234,900
6
2
1,144
Off Market
4280 Crosswinds Dr, Milton, FL 32583
0.14
$266,500
3
2
1,511
Off Market
4213 Breezeway Cir, Milton, FL 32583
0.13
$276,500
3
2
1,535
Off Market
5717 Meadow Rd, Milton, FL 32583
0.23
$87,900
2
2
959
Off Market
5705 Ridge Ave, Milton, FL 32583
0.23
$227,200
3
2
1,304
Off Market
5711 Meadow Rd, Milton, FL 32583
0.25
-
-
-
-
Off Market
4314 Crosswinds Dr, Milton, FL 32583
0.19
$256,500
3
2
1,533
Off Market
Oak Ln, Milton, FL 32570
0.25
-
-
-
-
Off Market

Local Information

  • Map ViewExplore the area around 4239 Crosswinds Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2001
0.26 acre lot
2,085 sqft
$145/sqft
Garage

About this House

NOT A SHORT SALE OR FORECLOSURE...Renovations are in process! Don't wait..you may still have time to choose your colors. Nice floor plan with 4 bedrooms, great room with vaulted ceiling and French doors to backyard, and a formal dining room. The kitchen is being completely gutted to include new cabinets in a coffee/cinnamon color, new granite-look countertops, new stainless appliances and tile floor. Carpet will be replaced in all living/bedroom areas. New tile floors in the bathrooms. The entire home will have fresh paint. And of course any additional repairs/cosmetics will be addressed. Still time to get this one under contract before the homebuyer tax credit expires! There is not a home on the market with this much square footage and like new condition and 2 car garage! Call today for a tour.
4239 Crosswinds Dr, Milton, FL 32583 is a 4 bedroom, 2 bathroom, 2,085 sqft single-family home built in 2001. It last sold for $143,800 on Aug 20, 2010. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $301,600, with a rent estimate of $2,096/month.

Home Details for 4239 Crosswinds Dr

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1Floors: Carpet, Linoleum Vinyl

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Other, BrickFoundation Type: SlabPatio
Parking & Garage
GarageParking: Garage

Property Information

Year Built
Year Built: 2001Year Updated: 2001
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 0.26 acres

Price and Tax history

DateEventPrice
Jan 24, 2011
Source: Agent Provided
ListingRemoved
$145,000
Aug 20, 2010
Source: N/A
Sold
$143,800
Aug 6, 2010
Source: Agent Provided
Listed For Sale
$145,000
Jun 28, 2010
Source: Agent Provided
ListingRemoved
$145,000
Apr 24, 2010
Source: Agent Provided
Listed For Sale
$145,000

Market trends in Milton

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$282K
$9.17KMoM
Sale-to-List Price
98.9%
0.1%MoM
Price per sq ft
$175
$3MoM
Available listings
352
10MoM

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 4239 Crosswinds Dr

  • What is 4239 Crosswinds Dr estimated to be worth?
    Trulia's estimated value for 4239 Crosswinds Dr in Milton, FL is $301,600.
  • What is the price history for 4239 Crosswinds Dr?
    4239 Crosswinds Dr in Milton, FL last sold for $143,800 in August 2010.
  • 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 $282K. That is up $9.17K from the prior month.
  • Does 4239 Crosswinds Dr have air conditioning?
    Yes, 4239 Crosswinds Dr in Milton, FL has air conditioning.
  • How big is the lot at 4239 Crosswinds Dr?
    The lot at 4239 Crosswinds Dr in Milton, FL is about 0.26 acres (11,250 sq ft).

Explore by feature - Pet Friendly

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Off Market Homes Near 4239 Crosswinds Dr

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