5599 Windham Rd, Milton, FL 32570
Property image
Property image
OFF MARKET

$251,800

Trulia Estimate
as of Oct 14, 2026
  • 3 Beds
  • 2 Baths
  • 1,368 sqft

5599 Windham Rd, Milton, FL 32570

Home Highlights

Single-Family Home
1,368 sqft
$184/sqft
Attached Garage

Local Information

  • Map ViewExplore the area around 5599 Windham Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

What's unique:Wood fireplaceLarge bedroomsTwo car garageHeat pump
Available Now
3 bedroom, 2 bathroom home in Milton, Florida. This 1,368 sqft single-family home built in 1999 sits on 1 acre and features large bedrooms, heat pump, wood fireplace, and a two car garage. Conveniently located close to Hwy 90/I-10. Additional fees may apply.
5599 Windham Rd, Milton, FL 32570 is a 3 bedroom, 2 bathroom, 1,368 sqft single-family home. It last sold for $140,000 on Dec 29, 2004 (8,385% above the $1,650 asking price). More recently, it was listed as a rental in March 2025 with an asking price of $2,100 per month. That rental listing was removed on March 10, 2025. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $251,800, with a rent estimate of $1,760/month.

Home Details for 5599 Windham Rd

Interior Features

Heating & Cooling
Heating: Heat PumpAir ConditioningCooling System: Central AirHeating Fuel: Heat Pump
Appliances & Utilities
DishwasherDryerRefrigeratorWasher

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: 1 Year

Exterior Features

Parking & Garage
Parking: Attached Off Street, On Site

Comparable Sales for 5599 Windham Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
5609 Columbia Ave, Milton, FL
0.10
Single-Family Home
$100,500
05/08/26
3
2
1,258 sqft
5389 Camille Gardens Cir, Milton, FL
0.07
Single-Family Home
$235,000
08/19/26
4
2
1,528 sqft
5437 Camille Gardens Cir, Milton, FL
0.25
Single-Family Home
$230,000
10/27/25
3
2
1,324 sqft
5429 Camille Gardens Cir, Milton, FL
0.22
Single-Family Home
$235,000
09/14/26
3
2
1,050 sqft
5761 Redoak Ln, Milton, FL
0.42
Single-Family Home
$126,500
05/11/26
3
2
1,344 sqft
5453 Camille Gardens Cir, Milton, FL
0.24
Single-Family Home
$235,000
05/11/26
4
1.5
1,410 sqft
5402 Douglas St, Milton, FL
0.41
Single-Family Home
$194,000
03/10/26
3
1.5
1,193 sqft
5457 Windham Rd, Milton, FL
0.34
Single-Family Home
$280,000
12/23/25
3
2
1,409 sqft
5435 Lucy Ln, Milton, FL
0.21
Single-Family Home
$299,000
11/06/25
3
2
2,061 sqft
5203 Tupelo Ln, Milton, FL
0.36
Single-Family Home
$138,100
11/21/25
3
2.5
1,788 sqft

Nearby homes

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Around this home

What Locals Say about Milton

This October

Trick-or-Treat Score

Built from what locals say about this neighborhood.
  • 77% say there's holiday spirit
  • 55% say neighbors are friendly
  • 24% say there are sidewalks
Trulia Trick or TreatStart Ghost Hunt
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
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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
    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

Price and Tax history

DateEventPrice
Mar 10, 2025
Source: Zillow Rentals
ListingRemoved
$1,650
Mar 10, 2025
Source: Zillow Rentals
PriceChange
$1,650
Price decreased by 21%
Mar 4, 2025
Source: Zillow Rentals
Listed For Rent
$2,100
Feb 20, 2025
Source: Zillow Rentals
ListingRemoved
$2,000
Jan 21, 2025
Source: Zillow Rentals
Listed For Rent
$2,000

Frequently asked questions about 5599 Windham Rd

  • What is 5599 Windham Rd estimated to be worth?
    Trulia's estimated value for 5599 Windham Rd in Milton, FL is $251,800.
  • What is the price history for 5599 Windham Rd?
    5599 Windham Rd in Milton, FL last sold for $140,000 in December 2004.
  • Is Milton a buyer's or seller's market?
    Milton is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Milton?
    The median sale price in Milton is $300K. That is up $5.5K from the prior month.
  • Does 5599 Windham Rd have air conditioning?
    Yes, 5599 Windham Rd in Milton, FL has air conditioning.
  • Does 5599 Windham Rd have laundry facilities?
    Yes, 5599 Windham Rd in Milton, FL has in-unit laundry.

Homes for rent near 5599 Windham Rd

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Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.
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