4259 Crosswinds Dr, Milton, FL 32583
OFF MARKET

4259 Crosswinds Dr
Milton, FL 32583

  • 4 Beds
  • 3 Baths
  • 3,020 sqft (on 0.25 acres)

$333,800

Trulia Estimate
as of Aug 1, 2026
Est. Refi. Payment $2,142/mo*
Refinance Your Home

$333,800

Trulia Estimate
as of Aug 1, 2026
Est. Refi. Payment $2,142/mo*
Refinance Your Home
4 Beds
3 Baths
3,020 sqft
(on 0.25 acres)

Local Information

  • Map ViewExplore the area around 4259 Crosswinds Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2001
Lot Size
0.25 acres
Living Area
3,020 sqft
Price/Sqft
$111
Parking
Garage

About this House

Unbelievable price! $50.48/SF for this large 4 bedroom, 3 full bath home, conveniently located close to shopping, hospital, and schools. Whiting Field is about 10 miles away. Easy access to I-10 and Pensacola or Crestview. Open kitchen and family room area plus formal living room and dining. Large master bedroom with big walk-in closet. Special features including architectural columns, vaulted ceilings in the living room, open kitchen design, garden tub with glass block, and covered patio. Ceramic Tile and wood laminate floors throughout. Jack and Jill bath serves two bedrooms, third bath for guests and 4th bedroom. Check out this exceptional property at a ridiculous price! Comparable sold properties have an average $/sf cost of $69 in the same subdivision. Thinking of investment property? Previous rental rate was $1100/month. If you have someone manage the property at 10%/month,taxes and insurance paid, rate of return will be in the neighborhood of 8-9%! Compare that to your IRA! This is the best value in the neighborhood!
4259 Crosswinds Dr, Milton, FL 32583 is a 4 bedroom, 3 bathroom, 3,020 sqft single-family home built in 2001. It last sold for $125,000 on Apr 15, 2011. It is currently off market. The Trulia Estimate is $333,800, with a rent estimate of $2,533/month.

Home Details for 4259 Crosswinds Dr

Interior Features

Heating & Cooling
Heating: Forced Air, Heat Pump, ElectricAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Hardwood
Interior Details
AtticNumber of Rooms: 15Types of Rooms: Walk In Closet, Dining Room, Family Room, Laundry Room, Master Bath, Office, Pantry, Recreation Room, Sun RoomCeiling Fan
Appliances & Utilities
Cable ReadyDishwasherDryerRefrigeratorWasher
Fireplace & Spa
Fireplace
Windows, Doors, Floors & Walls
Double Paned Windows

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Other, BrickFoundation Type: SlabLawn
Parking & Garage
GarageParking Spaces: 4Parking: Garage Attached, Off Street

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: 10890 sqft

Price History for 4259 Crosswinds Dr

DatePriceEventSource
04/15/2011$125,000Sold
N/A
02/16/2011$129,900PriceChange
Agent Provided
01/23/2011$139,900PriceChange
Agent Provided
12/16/2010$144,900PriceChange
Agent Provided
10/29/2010$149,900PriceChange
Agent Provided
06/27/2010$159,900PriceChange
Agent Provided
05/01/2010$169,900PriceChange
Agent Provided
01/23/2010$177,000Listed For SaleAgent Provided
02/07/2009$1,100ListingRemovedAgent Provided
01/23/2009$1,100PriceChange
Agent Provided
12/22/2008$1,250Listed For SaleAgent Provided
04/18/2005$197,000Sold
N/A
07/19/2001$130,900Sold
N/A

Market trends in Milton

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$273K
$10.92KMoM
Sale-to-List Price
99.1%
0.2%MoM
Price per sq ft
$172
$6MoM
Available listings
342
10MoM
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Property Tax and Assessment

Year2024
Tax$579
Assessment$254,467
Home facts updated by county records

Comparable Sales for 4259 Crosswinds Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
4263 Crosswinds Dr, Milton, FL
0.02
Single-Family Home
$310,000
10/21/25
4
3
2,636
5663 Sweet Birch Ln, Milton, FL
0.44
Single-Family Home
$267,000
04/09/26
4
2
2,557
5662 Pin Oak Ave, Milton, FL
0.40
Single-Family Home
$272,000
10/02/25
4
2
1,950
4331 Crosswinds Dr, Milton, FL
0.23
Single-Family Home
$285,000
04/28/26
3
2
1,515
5730 Ridge Ave, Milton, FL
0.17
Single-Family Home
$225,000
08/21/25
3
2
1,120
4411 Oak Ln, Milton, FL
0.30
Single-Family Home
$255,000
07/13/26
3
2
1,315
5650 Sweet Birch Ln, Milton, FL
0.45
Single-Family Home
$365,000
09/10/25
4
2
2,291
4490 Oak Ln, Milton, FL
0.29
Single-Family Home
$229,400
07/13/26
3
2
1,178
5714 Pine Dr, Milton, FL
0.30
Single-Family Home
$234,900
11/21/25
3
2
1,263
4482 Oak Ln, Milton, FL
0.30
Single-Family Home
$230,000
05/26/26
3
2
1,178

Nearby homes

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Assigned Schools

These are the assigned schools for 4259 Crosswinds Dr.
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 Milton

At least 263 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

  • 22 % 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
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  • 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
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  • 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
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  • 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
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  • Thedraiss5
    "Bands on the Blackwater and something down town almost every weekend................................................................. "
    0
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • Jennblane
    "There are no sidewalks around here- or even painted lanes. I miss biking and rollerblading. Definitely needs improvement."
    0
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  • 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
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  • Ellemcalla
    "Yes I see people walking their dogs at all hours of the day. There are lots of dog owners in this neighborhood."
    0
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  • 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
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  • Mike L.
    "I drive myself 6 miles to work and would likely not use public transportation if it became available."
    0
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  • Sere P. M. D.
    "Schools are excellent, very nice and quiet neighborhood, close to everything, highly recommended for all kind of families "
    0
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  • 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
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  • Cynthia N. W.
    "Lots of school aged children & military families in my neighborhood. Very safe. Must drive everywhere. "
    0
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  • Candace P.
    "The school in the area are amazing. East Milton is very nice place to live. My neighborhood is very safe. "
    0
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  • 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
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Homes for sale near 4259 Crosswinds Dr

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Off Market Homes Near 4259 Crosswinds Dr

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