4255 Crosswinds Dr, Milton, FL 32583
OFF MARKET

4255 Crosswinds Dr
Milton, FL 32583

  • 3 Beds
  • 2 Baths
  • 1,536 sqft (on 0.34 acres)

$250,700

Trulia Estimate
as of Jun 16, 2026
Est. Refi. Payment $1,579/mo*
Refinance Your Home

$250,700

Trulia Estimate
as of Jun 16, 2026
Est. Refi. Payment $1,579/mo*
Refinance Your Home
3 Beds
2 Baths
1,536 sqft
(on 0.34 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

null Brokered And Advertised By: WEEKS REALTY Listing Agent: LISA WEEKS
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
Patio
View
No Info
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 4255 Crosswinds Dr

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Laminate
Appliances & Utilities
DishwasherDryerMicrowaveWasher

Exterior Features

Exterior Home Features
Roof: Shake ShingleExterior: Vinyl, BrickFoundation Type: SlabPatio
Parking & Garage
GarageParking: Garage Attached

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: 0.34 acres

Price History for 4255 Crosswinds Dr

DatePriceEventSource
10/07/2022ListingRemovedPAR #616339
10/03/2022$268,000PriceChange
Navarre Area BOR #908800
09/21/2022$274,000Listed For SalePAR #616339
09/04/2020$165,000Sold
N/A
07/18/2013$1,200ListingRemovedAgent Provided
06/15/2013$1,200Listed For RentAgent Provided
07/24/2009$100,000Sold
N/A
05/01/2009$109,900PriceChange
Agent Provided
04/18/2009$0Listed For SaleAgent Provided
05/29/2001$87,900Sold
N/A

Market trends in Milton

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$262K
$6.48KMoM
Sale-to-List Price
99.4%
0.5%MoM
Price per sq ft
$166
$3MoM
Available listings
332
1MoM
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Property Tax and Assessment

Year2024
Tax$1,622
Assessment$177,889
Home facts updated by county records

Homeowner tools

Estimated monthly rent$1,816/mo
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Homes for rent near 4255 Crosswinds Dr

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Comparable Sales for 4255 Crosswinds Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
5737 Ridgefield Ct, Milton, FL
0.38
Single-Family Home
$178,000
10/29/25
3
2
1,538
4331 Crosswinds Dr, Milton, FL
0.25
Single-Family Home
$285,000
04/28/26
3
2
1,515
5730 Ridge Ave, Milton, FL
0.15
Single-Family Home
$225,000
08/21/25
3
2
1,120
5714 Pine Dr, Milton, FL
0.28
Single-Family Home
$234,900
11/21/25
3
2
1,263
4482 Oak Ln, Milton, FL
0.28
Single-Family Home
$230,000
05/26/26
3
2
1,178
5717 Loring Dr, Milton, FL
0.44
Single-Family Home
$285,000
04/07/26
3
2
1,622
5732 Charmonte Way, Milton, FL
0.51
Single-Family Home
$165,400
01/30/26
3
2
1,959
4417 Oak Ln, Milton, FL
0.29
Single-Family Home
$249,900
11/06/25
3
2
1,272
5953 Fairlands Rd, Milton, FL
0.43
Single-Family Home
$215,000
06/09/26
3
2
1,358
4263 Crosswinds Dr, Milton, FL
0.04
Single-Family Home
$310,000
10/21/25
4
3
2,636

Nearby homes

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Assigned Schools

These are the assigned schools for 4255 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
    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
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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
    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

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Homes for sale near 4255 Crosswinds Dr

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Off Market Homes Near 4255 Crosswinds Dr

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4255 Crosswinds Dr, Milton, FL 32583 is a 3 bedroom, 2 bathroom, 1,536 sqft single-family home built in 2001. This property is not currently available for sale. 4255 Crosswinds Dr was last sold on Sep 4, 2020 for $165,000. The current Trulia Estimate for 4255 Crosswinds Dr is $250,700.