5306 Windham Rd, Milton, FL 32570
Property image
Property image
OFF MARKET

$186,800

Trulia Estimate
as of Sep 21, 2026
  • 3 Beds
  • 2 Baths
  • 1,216 sqft

5306 Windham Rd, Milton, FL 32570

Home Highlights

Single-Family Home
1,216 sqft
$154/sqft

Local Information

  • Map ViewExplore the area around 5306 Windham Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Well-maintained 3-bedroom, 2-bathroom two-story home located off Hamilton Bridge Rd in a convenient Milton location close to shopping, dining and schools. Offering over 1,200 sq. ft. of living space, this home features tiled floors in the kitchen and bathrooms, a kitchen equipped with a refrigerator, electric stove and dishwasher and a primary bedroom downstairs with a private bathroom featuring a tub/shower combo and a walk-in closet. Two additional guest bedrooms are upstairs along with a second full bathroom with a tub/shower combo. An indoor laundry area with washer and dryer hookups is included and the fully fenced backyard offers privacy and space for pets or outdoor enjoyment. Pet-friendly with owner approval and a $250 non-refundable pet fee per pet (aggressive breeds not considered). Residents are required to have renter liability insurance, which can be added for $11.95/month or you can opt into the Resident Benefits Package (rbp) for $45/month, which includes renter liability insurance, HVAC air filter delivery and on-demand pest control. More details in the application. Dishwasher, Electric Stove, Oven, Pantry, Refrigerator, Carpet, Ceramic Tile, Breakfast Nook, Laundry Room, Living Room, Primary Bath, Primary Bedroom, Air Conditioning, Blinds, Cable / Satellite, Ceiling Fan, Washer Dryer Hookups, Fence, Patio & Pet Friendly.
5306 Windham Rd, Milton, FL 32570 is a 3 bedroom, 2 bathroom, 1,216 sqft single-family home. It last sold for $69,900 on Jun 10, 2015 (4,576% above the $1,495 asking price). More recently, it was listed as a rental in August 2025 with an asking price of $1,495 per month. That rental listing was removed on September 3, 2025. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $186,800, with a rent estimate of $1,708/month.

Home Details for 5306 Windham Rd

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: Contact For Details

Interior Features

Appliances & Utilities
DishwasherRefrigerator
Heating & Cooling
Air ConditioningCooling System: Central Air, Ceiling Fan
Levels, Entrance, & Accessibility
Floors: Carpet

Comparable Sales for 5306 Windham Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
5354 Windham Rd, Milton, FL
0.10
Single-Family Home
$215,000
03/31/26
3
2
1,196 sqft
5402 Douglas St, Milton, FL
0.31
Single-Family Home
$194,000
03/10/26
3
1.5
1,193 sqft
5457 Windham Rd, Milton, FL
0.32
Single-Family Home
$280,000
12/23/25
3
2
1,409 sqft
5609 Columbia Ave, Milton, FL
0.62
Single-Family Home
$100,500
05/08/26
3
2
1,258 sqft
5246 Persimmon Ln, Milton, FL
0.39
Single-Family Home
$259,900
11/21/25
3
2
1,271 sqft
5262 Springdale Dr, Milton, FL
0.62
Single-Family Home
$100,000
08/31/26
3
1
1,182 sqft
5377 Mountain Laurel Ln, Milton, FL
0.23
Single-Family Home
$352,900
10/20/25
5
2
2,191 sqft
5434 Gardenbrook Blvd, Milton, FL
0.24
Single-Family Home
$380,000
12/30/25
4
2
2,673 sqft
5429 Camille Gardens Cir, Milton, FL
0.61
Single-Family Home
$235,000
09/14/26
3
2
1,050 sqft
5437 Camille Gardens Cir, Milton, FL
0.64
Single-Family Home
$230,000
10/27/25
3
2
1,324 sqft

Nearby homes

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Rental Market Trends in Milton

Last updated Sep 2026
Trulia Rent Estimate$1,708/mo
Average rent
$1.9K
Available listings
103
View rental market trends in Milton, FL

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
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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
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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
    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
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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
    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
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  • 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
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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
    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
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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
    Flag

LGBTQ Local Legal Protections

Price and Tax history

DateEventPrice
Sep 3, 2025
Source: PAR #669193
ListingRemoved
$1,495
Aug 12, 2025
Source: PAR #669193
Listed For Rent
$1,495
Jun 24, 2022
Source: Zillow Rental Network_1
ListingRemoved
Jun 22, 2022
Source: Zillow Rental Network_1
Listed For Rent
$1,350
May 26, 2019
Source: Agent Provided
ListingRemoved
$1,025

Frequently asked questions about 5306 Windham Rd

  • What is 5306 Windham Rd estimated to be worth?
    Trulia's estimated value for 5306 Windham Rd in Milton, FL is $186,800.
  • What is the price history for 5306 Windham Rd?
    5306 Windham Rd in Milton, FL last sold for $69,900 in June 2015.
  • 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 $297K. That is up $13.08K from the prior month.
  • Does 5306 Windham Rd have air conditioning?
    Yes, 5306 Windham Rd in Milton, FL has air conditioning.

Homes for rent near 5306 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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