8914 Oak Shadow Rd, Milton, FL 32583
Property image
Property image
OFF MARKET

8914 Oak Shadow Rd
Milton, FL 32583

  • 3 Beds
  • 3 Baths
  • 2,260 sqft

$381,700

Trulia Estimate
as of Aug 24, 2026
Est. Refi. Payment $2,414/mo*
Refinance Your Home

$381,700

Trulia Estimate
as of Aug 24, 2026
Est. Refi. Payment $2,414/mo*
Refinance Your Home
3 Beds
3 Baths
2,260 sqft

Home Value

Trulia Estimate
$382K
Since last month
Decreased$2K (-0.5%)
Since last year
Increased$9K (+2.4%)
Since last sale
Increased$13K (+3.4%)
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 +2% in the last 10 years
MonthEstimated value
2026
August 2026$383K
July 2026$384K
June 2026$384K
May 2026$381K
April 2026$380K
March 2026$380K
February 2026$379K
January 2026$379K
2025
2024

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
5198 Santa Rosa St, Milton, FL
0.17
Single-Family Home
$230,000
09/12/25
3
2
1,820
5293 Conecuh St, Milton, FL
0.35
Single-Family Home
$371,900
06/12/26
3
2
1,824
5093 Canal St, Milton, FL
0.26
Single-Family Home
$251,000
12/18/25
3
2
1,670
5108 Escambia St, Milton, FL
0.12
Single-Family Home
$180,000
06/16/26
5
2
2,383
5190 Santa Rosa St, Milton, FL
0.15
Single-Family Home
$134,500
04/09/26
4
2
1,878
6773 Taylor St, Milton, FL
0.74
Single-Family Home
$379,900
12/05/25
3
2.5
2,124
5185 Canal St, Milton, FL
0.21
Single-Family Home
$150,000
02/27/26
6
2
2,235
5261 Bayou Dr, Milton, FL
0.53
Single-Family Home
$533,403
02/12/26
3
2
1,850
5115 Pike St, Milton, FL
0.18
Single-Family Home
$187,500
09/29/25
3
1
1,039

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
5108 Escambia St, Milton, FL 32570
0.12
$180,000
5
2
2,383
Recently Sold
5148 Willing St, Milton, FL 32570
0.12
$520,000
Studio
-
-
For Sale
5115 Escambia St, Milton, FL 32570
0.14
$221,600
3
1.5
1,400
Off Market
5241 Willing St #A, Milton, FL 32570
0.14
-
6
3
3,890
Off Market
5190 Santa Rosa St, Milton, FL 32570
0.15
$134,500
4
2
1,878
Recently Sold
5198 Santa Rosa St, Milton, FL 32570
0.17
$235,800
3
2
1,820
Off Market
5115 Pike St, Milton, FL 32570
0.18
$192,000
3
1
1,039
Off Market
5165 Canal St, Milton, FL 32570
0.19
$356,800
3
2
2,128
Off Market
5200 Canal St, Milton, FL 32570
0.20
$210,000
2
1.5
1,500
For Sale
5185 Canal St, Milton, FL 32570
0.21
$150,000
6
2
2,235
Recently Sold
6793 Margaret St, Milton, FL 32570
0.23
$155,300
6
1
1,111
Off Market

Local Information

  • Map ViewExplore the area around 8914 Oak Shadow Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2025
Living Area
2,260 sqft
Price/Sqft
$169
Parking
Garage

About this House

Welcome to the Dora, a floorplan from the Cornerstone collection by Holiday Builders. This new home floorplan offers a spacious and functional layout designed to accommodate the needs of your family while providing a touch of elegance.
The Dora features three bedrooms, offering ample space for everyone to have their own private retreats. Additionally, there is a versatile den/flex space that can be transformed into a home office, playroom, or fourth bedroom depending on your preferences.
Upon entering the foyer, you'll immediately notice a bedroom to the right, complete with a separate full bathroom and linen closet. This arrangement ensures privacy and convenience for guests or family members. To the left, a long wall awaits, providing an ideal space for showcasing your cherished family photographs and adding a personal touch to your home.
Moving beyond the front bedroom, you'll discover an open dining room and great room, creating an expansive and welcoming atmosphere for entertaining and creating lasting memories. Just outside the great room, an outdoor living area invites you to relax and enjoy the fresh air.
8914 Oak Shadow Rd, Milton, FL 32583 is a 3 bedroom, 3 bathroom, 2,260 sqft single-family home built in 2025. It last sold for $370,000 on Feb 26, 2025 (2% below the $376,514 asking price). It is currently off market. The Trulia Estimate is $381,700, with a rent estimate of $2,556/month.
Contact this Building
Property Website
Source: Holiday Builders

Home Details for 8914 Oak Shadow Rd

Interior Features

Levels, Entrance, & Accessibility
Stories: 1

Property Information

Year Built
Year Built: 2025
Property Type / Style
Property Type: Single Family HomeArchitecture: House

Exterior Features

Parking & Garage
GarageParking Spaces: 2Parking: Garage

Price and Tax history

DateEventPrice
Feb 26, 2025
Source: N/A
Sold
$370,000
Oct 16, 2024
Source: Holiday Builders
PriceChange
$376,514
Price increased by 1%
Apr 24, 2024
Source: Holiday Builders
Listed For Sale
$373,609

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
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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
    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
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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

LGBTQ Local Legal Protections

Frequently asked questions about 8914 Oak Shadow Rd

  • What is 8914 Oak Shadow Rd estimated to be worth?
    Trulia's estimated value for 8914 Oak Shadow Rd in Milton, FL is $381,700.
  • What is the price history for 8914 Oak Shadow Rd?
    8914 Oak Shadow Rd in Milton, FL last sold for $370,000 in February 2025.
  • 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 8914 Oak Shadow Rd have a garage?
    Yes, 8914 Oak Shadow Rd in Milton, FL has a garage.

Explore by feature - Pet Friendly

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