5299 Windham Rd, Milton, FL 32570
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Property image
OFF MARKET

5299 Windham Rd
Milton, FL 32570

  • 3 Beds
  • 2.5 Baths
  • 2,020 sqft (on 1.62 acres)

$410,000

Trulia Estimate
as of Aug 14, 2026
Est. Refi. Payment $2,572/mo*
Refinance Your Home

$410,000

Trulia Estimate
as of Aug 14, 2026
Est. Refi. Payment $2,572/mo*
Refinance Your Home
3 Beds
2.5 Baths
2,020 sqft
(on 1.62 acres)

Home Value

Trulia Estimate
$410K
Since last month
Decreased$3K (-0.8%)
Since last year
Increased$13K (+3.3%)
Since last sale
Increased$250K (+157%)
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 +112% in the last 10 years
MonthEstimated value
2026
August 2026$409K
July 2026$403K
June 2026$412K
May 2026$401K
April 2026$400K
March 2026$399K
February 2026$392K
January 2026$383K
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
5425 Windham Rd, Milton, FL
0.35
Single-Family Home
$450,000
03/11/26
3
2.5
2,466
5402 Douglas St, Milton, FL
0.36
Single-Family Home
$194,000
03/10/26
3
1.5
1,193
5354 Windham Rd, Milton, FL
0.16
Single-Family Home
$215,000
03/31/26
3
2
1,196
5530 Hamilton Bridge Rd, Milton, FL
0.69
Single-Family Home
$133,000
03/16/26
4
2.5
1,877
5413 Hamilton Bridge Rd, Milton, FL
0.56
Single-Family Home
$165,000
04/06/26
3
1
1,407
5457 Windham Rd, Milton, FL
0.39
Single-Family Home
$280,000
12/23/25
3
2
1,409
5203 Tupelo Ln, Milton, FL
0.83
Single-Family Home
$138,100
11/21/25
3
2.5
1,788
5434 Gardenbrook Blvd, Milton, FL
0.28
Single-Family Home
$380,000
12/30/25
4
2
2,673
5377 Mountain Laurel Ln, Milton, FL
0.31
Single-Family Home
$352,900
10/20/25
5
2
2,191
5246 Persimmon Ln, Milton, FL
0.47
Single-Family Home
$259,900
11/21/25
3
2
1,271

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
5301 Windham Rd, Milton, FL 32570
0.06
$603,800
5
3.5
3,138
Off Market
5354 Windham Rd, Milton, FL 32570
0.15
$215,000
3
2
1,196
Recently Sold
5351 Bella Ridge Rd, Milton, FL 32570
0.18
$685,100
5
4.5
3,336
Off Market
5418 Gardenbrook Blvd, Milton, FL 32570
0.26
$336,600
4
3
2,675
Off Market
5434 Gardenbrook Blvd, Milton, FL 32570
0.28
$380,000
4
2
2,673
Recently Sold
5352 Mountain Laurel Ln, Milton, FL 32570
0.30
$500,200
4
3
3,154
Off Market
5377 Mountain Laurel Ln, Milton, FL 32570
0.31
$352,900
5
2
2,191
Recently Sold
5353 Mountain Laurel Ln, Milton, FL 32570
0.33
$487,900
4
3
3,088
Off Market
5471 Cottonwood Dr, Milton, FL 32570
0.33
$377,500
4
3
2,108
Off Market
5336 Tildon St, Milton, FL 32570
0.29
$667,700
3
2
2,664
Off Market
5267 Gardenbrook Blvd, Milton, FL 32570
0.36
$498,000
5
3
3,004
Recently Sold
5200 Tildon St, Milton, FL 32570
0.30
$800,300
3
2.5
3,403
Off Market

Local Information

  • Map ViewExplore the area around 5299 Windham Rd.
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Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2006
Lot Size
1.62 acres
Living Area
2,020 sqft
Price/Sqft
$203
Parking
Garage

About this House

Nice home home on over 1.5 acres in Bentley Woods. Home features an open and bright living/dining room that opens to a breakfast nook and kitchen with a breakfast bar. Kitchen leads to a butlers pantry and laundry room with a sink. Home also features a master bath with a garden tub and separate tiles shower. Off the back off the back of the home you will find a screened in patio that overlooks a large, privacy fenced backyard with a detached 2 car garage/workshop(in addition to the 2 car attached to garage to home). HURRY! This home won't last long!
5299 Windham Rd, Milton, FL 32570 is a 3 bedroom, 3 bathroom, 2,020 sqft single-family home built in 2006. It last sold for $159,000 on Oct 5, 2016. It is currently off market. The Trulia Estimate is $410,000, with a rent estimate of $2,084/month.

Home Details for 5299 Windham Rd

Interior Features

Heating & Cooling
Heating: Forced Air, ElectricAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1Floors: Laminate
Interior Details
Types of Rooms: Walk In Closet, Family Room, Master Bath, Pantry, Workshop, Sun RoomCeiling Fan
Appliances & Utilities
DishwasherDryerMicrowaveRefrigerator
Fireplace & Spa
Jetted Bath Tub

Exterior Features

Exterior Home Features
Roof: Shake ShingleDeckExterior: BrickFoundation Type: MasonryLawnPorch
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached, Garage Detached

Property Information

Year Built
Year Built: 2006Year Updated: 2006
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 1.62 acres

Price and Tax history

DateEventPrice
Oct 5, 2016
Source: PAR #498196
Sold
$159,000
Jul 22, 2016
Source: Agent Provided
PriceChange
$159,900
Price decreased by 3%
Jul 20, 2016
Source: Agent Provided
Listed For Sale
$164,900
Jun 16, 2016
Source: Agent Provided
ListingRemoved
$164,900
May 18, 2016
Source: Agent Provided
PriceChange
$164,900
Price decreased by 6%

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
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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
    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
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  • 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
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  • 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
    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
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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
    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
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  • 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
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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
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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
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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

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Apartments for Rent

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Homes for sale near 5299 Windham Rd

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Off Market Homes Near 5299 Windham Rd

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Frequently asked questions about 5299 Windham Rd

  • What is 5299 Windham Rd estimated to be worth?
    Trulia's estimated value for 5299 Windham Rd in Milton, FL is $410,000.
  • What is the price history for 5299 Windham Rd?
    5299 Windham Rd in Milton, FL last sold for $159,000 in October 2016.
  • 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 5299 Windham Rd have air conditioning?
    Yes, 5299 Windham Rd in Milton, FL has air conditioning.
  • Does 5299 Windham Rd have laundry facilities?
    Yes, 5299 Windham Rd in Milton, FL has laundry facilities.