4339 Crosswinds Dr, Milton, FL 32583
OFF MARKET

$279,400

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 2,202 sqft (on 0.26 acres)

4339 Crosswinds Dr, Milton, FL 32583

Est. Refi. Payment $1,785/mo*
Refinance Your Home
Currently Off Market - Sold Mar 15, 2018 for $57,300

Home Value

Trulia Estimate
$279K
Since last month
Decreased$700 (-0.2%)
Since last year
Increased$2K (+0.8%)
Since last sale
Increased$222K (+388.1%)
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 +84% in the last 10 years
MonthEstimated value
2026
August 2026$280K
August 2026$279K
July 2026$280K
June 2026$280K
May 2026$283K
April 2026$280K
March 2026$281K
February 2026$276K
January 2026$265K
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
4331 Crosswinds Dr, Milton, FL
0.03
Single-Family Home
$285,000
04/28/26
3
2
1,515
5953 Fairlands Rd, Milton, FL
0.17
Single-Family Home
$215,000
06/09/26
3
2
1,358
4263 Crosswinds Dr, Milton, FL
0.24
Single-Family Home
$310,000
10/21/25
4
3
2,636
5662 Pin Oak Ave, Milton, FL
0.60
Single-Family Home
$272,000
10/02/25
4
2
1,950
5663 Sweet Birch Ln, Milton, FL
0.59
Single-Family Home
$267,000
04/09/26
4
2
2,557
4411 Oak Ln, Milton, FL
0.55
Single-Family Home
$255,000
07/13/26
3
2
1,315
4490 Oak Ln, Milton, FL
0.52
Single-Family Home
$229,400
07/13/26
3
2
1,178
4482 Oak Ln, Milton, FL
0.53
Single-Family Home
$230,000
05/26/26
3
2
1,178
5714 Pine Dr, Milton, FL
0.55
Single-Family Home
$234,900
11/21/25
3
2
1,263
5614 Rosebay St, Milton, FL
0.69
Single-Family Home
$289,000
02/03/26
3
2
1,902

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
4331 Crosswinds Dr, Milton, FL 32583
0.03
$285,000
3
2
1,515
Recently Sold
5889 Fairlands Rd, Milton, FL 32583
0.08
$256,200
3
2
1,473
Off Market
4315 Crosswinds Dr, Milton, FL 32583
0.10
$274,800
3
2
1,714
Off Market
5873 Fairlands Rd, Milton, FL 32583
0.11
$296,500
3
2
1,475
For Sale
4314 Crosswinds Dr, Milton, FL 32583
0.12
$256,500
3
2
1,533
Off Market
5829 Fairlands Rd, Milton, FL 32571
0.13
$257,700
3
2
1,473
Off Market
4213 Breezeway Cir, Milton, FL 32583
0.14
$276,500
3
2
1,535
Off Market
5861 Fairlands Rd, Milton, FL 32583
0.13
$259,600
3
2
1,318
Off Market
5853 Fairlands Rd, Milton, FL 32583
0.15
$308,400
4
2
1,736
Off Market
5849 Fairlands Rd, Milton, FL 32583
0.15
$274,900
3
2
1,475
For Sale
4280 Crosswinds Dr, Milton, FL 32583
0.16
$266,500
3
2
1,511
Off Market
5949 Fairlands Rd, Milton, FL 32583
0.16
$280,000
3
2
1,553
Off Market

Local Information

  • Map ViewExplore the area around 4339 Crosswinds Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2002
0.26 acre lot
2,202 sqft
$127/sqft
Garage

About this House

Call this well-maintained one owner home your own. Conveniently located in Crosswinds in the Avalon area; here you are close to everything-Milton, Pace, Pensacola, Gulf Breeze, and I-10. This home boasts three generously sized Bedrooms, plus and Office/Dining room, and converted Game Room. On the walk up to this tastefully designed home you will notice the inviting front porch, the front door comes equipped with a glass storm door, and upon entry you will see the architectural columns and beams that make this home stunning to the eyes. The extra large Kitchen and Dining area blend into the Great Room, separated by columns and give that desired "open" feel. Kitchen has lots of countertops and pickled cabinets, island with breakfast bar, lighted corner pantry, smooth top stove and under-mount microwave. A skylight bathes the kitchen and dining areas in natural sunlight, and give the area an uplifting feeling. The Master Bedroom is large with room for a sitting area, and Master Bath has two large his and hers walk in closets, double vanity and garden tub/shower combo. Two additional Bedrooms are generously sized, and split floor plan separates these from the Master suite. Game Room is converted space and its uses are endless; it is included in the square footage, well insulated and heated and cooled. Storage is not an issue with additional shelving in all closets, linen closet and coat closet. All this located in the back of this quiet neighborhood near the end of the street for safety. Back yard includes a metal storage building and privacy fence. Come and see this well equipped home for yourself, call today for your private tour.<br/><br/>Brokered And Advertised By: GRAND REALTY, INC.<br/>Listing Agent: NANCY BROWN
4339 Crosswinds Dr, Milton, FL 32583 is a 3 bedroom, 2 bathroom, 2,202 sqft single-family home built in 2002. It last sold for $57,300 on Mar 15, 2018. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $279,400, with a rent estimate of $2,054/month.

Home Details for 4339 Crosswinds Dr

Interior Features

Interior Details
Basement
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: Slab
Parking & Garage
GarageParking: Garage

Property Information

Year Built
Year Built: 2002Year Updated: 2002
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
Mar 15, 2018
Source: N/A
Sold
$57,300
Jul 29, 2010
Source: N/A
Sold
$129,000
Jun 7, 2010
Source: Agent Provided
PriceChange
$124,900
Price decreased by 4%
Jun 4, 2010
Source: Agent Provided
PriceChange
$129,900
Price decreased by 2%
May 23, 2010
Source: Agent Provided
PriceChange
$132,900
Price decreased by 2%

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
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  • 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
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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
    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
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  • 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
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  • 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
    Flag
  • 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
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  • 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
    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 4339 Crosswinds Dr

  • What is 4339 Crosswinds Dr estimated to be worth?
    Trulia's estimated value for 4339 Crosswinds Dr in Milton, FL is $279,400.
  • What is the price history for 4339 Crosswinds Dr?
    4339 Crosswinds Dr in Milton, FL last sold for $57,300 in March 2018.
  • 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 4339 Crosswinds Dr have air conditioning?
    Yes, 4339 Crosswinds Dr in Milton, FL has air conditioning.
  • How big is the lot at 4339 Crosswinds Dr?
    The lot at 4339 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 4339 Crosswinds Dr

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