5590 Windham Rd, Milton, FL 32570
OFF MARKET

5590 Windham Rd
Milton, FL 32570

  • 2 Beds
  • 1.5 Baths
  • 1,000 sqft (on 0.28 acres)

$210,300

Trulia Estimate
as of May 10, 2026
Est. Refi. Payment $1,307/mo*
Refinance Your Home

$210,300

Trulia Estimate
as of May 10, 2026
Est. Refi. Payment $1,307/mo*
Refinance Your Home
2 Beds
1.5 Baths
1,000 sqft
(on 0.28 acres)

Homes for sale near 5590 Windham Rd

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Local Information

Map showing home location
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-- mins to
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Description

Welcome home! Adorable cottage style home for sale in Milton. This property offers a picturesque first impression with lovely Bermuda shutters, white picket fence, brick paver walkway, and charming Gambrel style roof line. Speaking of roofs, this beauty is getting a brand new one! (On order). Inside you will find a spacious open living/dining/kitchen combo. Kitchen features lots of countertop space and pantry. Two large bedrooms, 1.5 bathrooms. All doorways in this house are oversized, making it very accommodating for wheelchairs if needed. Master bath features a seated jacuzzi style jetted bathtub/shower combo. One car attached garage, PLUS a huge detached garage. Come check out this one-of-a-kind property today!
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
No Info

Home Details for 5590 Windham Rd

Interior Features

Heating & Cooling
Heating: Forced Air, ElectricAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Interior Details
Types of Rooms: Breakfast Nook, Dining RoomCeiling Fan
Levels, Entrance, & Accessibility
Floors: Carpet

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: VinylFoundation Type: SlabPatio
Parking & Garage
GarageParking Space: 1Parking: Garage Attached

Property Information

Year Built
Year Built: 1993Year Updated: 1992
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 0.28 acres

Price History for 5590 Windham Rd

DatePriceEventSource
10/27/2022$200,000Sold
PAR #615720
10/27/2022$189,900PendingPAR #615720
09/21/2022$189,900ContingentPAR #615720
09/18/2022$189,900Listed For SalePAR #615720
03/15/2021$144,500Sold
PAR #583598
01/19/2021$139,900Listed For SaleAgent Provided
08/22/2019$995ListingRemovedAgent Provided
07/26/2019$995Listed For RentAgent Provided
05/24/2018$108,200ListingRemovedAgent Provided
05/12/2018$108,200PriceChange
Agent Provided
05/03/2018$108,300PriceChange
Agent Provided
04/27/2018$108,400PriceChange
Agent Provided
04/19/2018$108,500PriceChange
Agent Provided
04/07/2018$108,700PriceChange
Agent Provided
03/30/2018$108,800PriceChange
Agent Provided
03/12/2018$108,900PriceChange
Agent Provided
03/09/2018$109,000PriceChange
Agent Provided
03/02/2018$109,100PriceChange
Agent Provided
02/21/2018$109,200PriceChange
Agent Provided
02/17/2018$109,300PriceChange
Agent Provided
02/08/2018$109,400PriceChange
Agent Provided
02/05/2018$109,500PriceChange
Agent Provided
01/30/2018$109,600PriceChange
Agent Provided
01/24/2018$109,700PriceChange
Agent Provided
01/19/2018$109,800PriceChange
Agent Provided
01/15/2018$109,900Listed For SaleAgent Provided
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Property Tax and Assessment

Year2024
Tax$1,624
Assessment$133,128
Home facts updated by county records

Comparable Sales for 5590 Windham Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
5437 Camille Gardens Cir, Milton, FL
0.20
Single-Family Home
$230,000
10/27/25
3
2
1,324
5500 Marsha Dr, Milton, FL
0.35
Single-Family Home
$251,000
07/29/25
3
2
1,498
5354 Windham Rd, Milton, FL
0.53
Single-Family Home
$215,000
03/31/26
3
2
1,196
5435 Lucy Ln, Milton, FL
0.16
Single-Family Home
$299,000
11/06/25
3
2
2,061
5583 Jones St, Milton, FL
0.53
Single-Family Home
$200,000
08/20/25
3
2
1,293
5457 Windham Rd, Milton, FL
0.31
Single-Family Home
$280,000
12/23/25
3
2
1,409
5246 Persimmon Ln, Milton, FL
0.39
Single-Family Home
$259,900
11/21/25
3
2
1,271
5402 Douglas St, Milton, FL
0.37
Single-Family Home
$194,000
03/10/26
3
1.5
1,193
5541 Berryhill Rd, Milton, FL
0.60
Single-Family Home
$235,000
05/30/25
3
2
1,284
5559 Jones St, Milton, FL
0.48
Single-Family Home
$255,000
12/12/25
3
2
1,505

Assigned Schools

These are the assigned schools for 5590 Windham Rd.
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

  • 86 % 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

  • 46 % 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

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
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  • Caitfranko
    "It’s safe. We have yard sales frequently. Neighbors are friendly. Kid/family friendly. "
    0
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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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
    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
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Homes for rent near 5590 Windham Rd

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Off Market Homes Near 5590 Windham Rd

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Explore by feature

5590 Windham Rd, Milton, FL 32570 is a 2 bedroom, 2 bathroom, 1,000 sqft single-family home built in 1993. This property is not currently available for sale. 5590 Windham Rd was last sold on Oct 27, 2022 for $200,000. The current Trulia Estimate for 5590 Windham Rd is $210,300.