103 Winchester Way, Crestview, FL 32539
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OFF MARKET

103 Winchester Way
Crestview, FL 32539

  • 3 Beds
  • 2 Baths
  • 1,640 sqft

$299,100

Trulia Estimate
as of Jul 6, 2026
Est. Refi. Payment $1,866/mo*
Refinance Your Home

$299,100

Trulia Estimate
as of Jul 6, 2026
Est. Refi. Payment $1,866/mo*
Refinance Your Home
3 Beds
2 Baths
1,640 sqft

Local Information

  • Map ViewExplore the area around 103 Winchester Way.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Elevate your lifestyle with this exquisite long-term rental in Crestview! Boasting 3 bedrooms, 2 bathrooms, and an attached 2-car garage, this residence is the epitome of homey sophistication. Experience the ease of electric AC, heating, and water heating, coupled with the added comfort of ceiling fans and blinds. Revel in the contemporary blend of tile and vinyl flooring in the main living areas, complemented by brand new carpet in the bedrooms.Unwind by the electric fireplace in the open living area, and relish the privacy afforded by the thoughtfully designed split bedroom floor plan. The fully equipped kitchen features an electric stove/oven, refrigerator, dishwasher, and a standalone microwave (as-is). The expansive laundry room includes washer/dryer included and a custom-built slide-out cabinet for organized storage of laundry supplies.Escape to the primary suite, offering dual vanity, a jacuzzi tub, and a separate shower for your ultimate relaxation. Step outside to a covered back patio and a privacy-fenced backyard, creating the perfect outdoor oasis. This home is equipped with smart features, including a Ring doorbell (AS-IS), keyless door entry, smart light switches, and a WiFi-enabled garage door opener. Welcome to your new home sweet home, where luxury meets functionality!
Pets are accepted with a $250 per pet non-refundable pet fee (Subject to Owner Approval).
No smoking is permitted.

In addition to the rental amount, all Sundance Rental Management residents are enrolled in the Resident Benefits Package (RBP) for $25.00/month which includes liability insurance, credit building to help boost the resident's credit score with timely rent payments, and much more! The benefits can be found on our website under Tenant FAQ.
103 Winchester Way, Crestview, FL 32539 is a 3 bedroom, 2 bathroom, 1,640 sqft single-family home. It last sold for $295,000 on Aug 1, 2022 (16,289% above the $1,800 asking price). More recently, it was listed as a rental in December 2025 with an asking price of $1,800 per month. That rental listing was removed on January 15, 2026. It is currently off market. The Trulia Estimate is $299,100, with a rent estimate of $1,979/month.

Home Highlights

Parking
Attached Garage
Outdoor
Patio
View
No Info
HOA
None
Price/Sqft
No Info
Listed
180+ days ago

Home Details for 103 Winchester Way

Interior Features

Heating & Cooling
Heating: FireplaceCooling System: Ceiling FanHeating Fuel: Fireplace
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: Contact For DetailsAvailable: now

Exterior Features

Parking & Garage
GarageParking: Attached Garage, On Site

Price History for 103 Winchester Way

DatePriceEventSource
01/15/2026$1,800ListingRemovedZillow Rentals
12/02/2025$1,800Listed For RentZillow Rentals
01/30/2024ListingRemovedZillow Rentals
01/19/2024$1,900PriceChange
Zillow Rentals
12/22/2023$2,000PriceChange
Zillow Rentals
11/29/2023$2,150Listed For RentZillow Rentals
08/01/2022$295,000Sold
ECAOR #902154
07/07/2022$289,900PendingECAOR #902154
06/30/2022$289,900PriceChange
ECAOR #902154
06/26/2022$299,900Listed For SaleECAOR #902154
06/13/2019$184,000Sold
N/A
04/23/2019$180,000PendingAgent Provided
04/21/2019$180,000Listed For SaleAgent Provided
10/24/2012$93,000ListingRemovedAgent Provided
10/20/2012$93,000Listed For SaleAgent Provided
05/27/2010$159,900Sold
N/A
02/22/2010$166,400Listed For SaleAgent Provided
12/19/2009$166,400ListingRemovedAgent Provided
09/14/2009$166,400PriceChange
Agent Provided
11/27/2008$166,900PriceChange
Agent Provided
06/26/2008$169,900PriceChange
Agent Provided
06/12/2008$179,900PriceChange
Agent Provided
04/05/2008$189,900Listed For SaleAgent Provided
11/07/2000$14,000Sold
N/A

Market trends in Crestview

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$298K
$1.43KMoM
Sale-to-List Price
99.5%
0.5%MoM
Price per sq ft
$165
$3MoM
Available listings
511
13MoM
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Property Tax and Assessment

Year2024
Tax$2,458
Assessment$245,663
Home facts updated by county records

Comparable Sales for 103 Winchester Way

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
2806 Blackbird Ct, Crestview, FL
0.21
Single-Family Home
$299,000
07/02/26
3
2
1,533
2834 Blackbird Ct, Crestview, FL
0.21
Single-Family Home
$323,300
04/30/26
3
2
1,616
1415 Red Oak Dr, Crestview, FL
0.24
Single-Family Home
$323,995
10/29/25
3
2
1,762
2831 Blackbird Ct, Crestview, FL
0.28
Single-Family Home
$300,049
04/08/26
3
2
1,533
2832 Blackbird Ct, Crestview, FL
0.30
Single-Family Home
$322,000
04/24/26
3
2
1,616
3005 Lillie St, Crestview, FL
0.31
Single-Family Home
$299,999
02/03/26
3
2
1,557
2829 Blackbird Ct, Crestview, FL
0.26
Single-Family Home
$278,000
07/02/26
3
2
1,337
3077 Border Creek Rd, Crestview, FL
0.14
Single-Family Home
$299,900
12/29/25
4
2
2,393
2801 Blackbird Ct, Crestview, FL
0.20
Single-Family Home
$348,000
06/17/26
4
2
1,823
2833 Blackbird Ct, Crestview, FL
0.30
Single-Family Home
$275,000
05/15/26
3
2
1,337

Nearby homes

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Assigned Schools

These are the assigned schools for 103 Winchester Way.
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 Crestview

At least 379 Trulia users voted on each feature.

  • 91 % Say car is needed

  • 83 % Say parking is easy

  • 81 % Say yards are well-kept

  • 78 % Say it's dog friendly

  • 74 % Say there's holiday spirit

  • 67 % Say kids play outside

  • 67 % Say it's quiet

  • 57 % Say people would walk alone at night

  • 51 % Say neighbors are friendly

  • 48 % Say there's wildlife

  • 38 % Say they plan to stay for at least 5 years

  • 28 % Say there are sidewalks

  • 28 % Say streets are well-lit

  • 25 % Say it's walkable to grocery stores

  • 20 % Say it's walkable to restaurants

  • 18 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Numberonly33
    "I’ve been here for 10 years and my kids have a good experience in school as well as the neighborhood I live in the Auburn area. Yard Neighbourhood downtown area looks really good. Most areas of the town maintain well.."
    0
    Flag
  • Hazel Diane Fetter
    "Nothing it’s very quiet and safe place to walk. The neighbors are friendly. The neighborhood is clean and safe. "
    0
    Flag
  • Vym6nt6t2s
    "It’s nice here for the most part of course we have some neighbors that are not nice and make comments and are holy then thou kinda people but for the most part everyone’s nice here"
    1
    Flag
  • Martin Paras
    "Almost 2 years living here honestly I don’t see lots of dogs in our area. There’s some but definitely dog owners will love to live here because the roads are not busy. Neighborhood our pet friendly. "
    0
    Flag
  • Eperez009
    "I drive everywhere. There really isn't great city infrastructure. No sidewalks in most communities. 2 main roads go up and down the city, which creates heavy traffic. "
    0
    Flag
  • Teresa W.
    "I have lived here for almost forty years. Our small town has grown into a decent sized smaller city. People are friendly and helpful to others if they need it. Lots of different things to do. Pet friendly"
    5
    Flag
  • Aliciabyrd1227
    "There are a bunch of Stray cats. Other dog owners don’t clean up after their dogs while on walks. Some of the fences make it easy for dogs to escape."
    0
    Flag
  • Tabathaworkman
    "I don’t really know I have only lived here 2yrs so I haven’t been out in the community. Twin Hills park is nice, for walking and walking dogs also a nice park for kids"
    0
    Flag
  • Kelcie
    "Dog owners would love the roads and subdivisions they can walk their dog. It’s very quiet here and relaxing. "
    7
    Flag
  • Tabathaworkman
    "New to the area, not sure of a lot of things. Fireworks on Fourth of July and family movie nights that are free."
    0
    Flag
  • Christina B.
    "Lived here 5yrs. Neighborhood is friendly and everyone looks out for one another. We have our own FB page where we share happenings in our neighborhood/community. "
    1
    Flag
  • Kody P.
    "I have lived here for a year and am surprised I haven't been robbed yet. Seriously, if you're going to live in this city live on the south side, not the north..or don't live here. It's truly a drug infested violent area. No place to raise a family...on the north side that is. South Crestview isn't too bad, with the city expanding and new homes being built next to nicer newer homes and apartment complexes. Be wise. "
    2
    Flag
  • Shaye_murphy
    "People are friendly towards pets as long as you pick up after them and don’t let them bark all hours of the night. Just simple pet courtesies."
    0
    Flag
  • Elisha B.
    "quiet neighborhoods. friendly neighborhoods. large backyards for pets to enjoy. definitely a great place to have a pet. "
    0
    Flag
  • Justin T.
    "Have a dog yard. Everyone has the dogs on leash when walking I don’t really know what else to say jckxbxoxbxjxbx"
    0
    Flag
  • Taylormindy25
    "We take are children trick or treating every year in Crestview. We go where ever we live up and down the road so we feel more safe about letting them eat the candy"
    0
    Flag
  • Taylormindy25
    "It’s a great place to live and to rise your children. Crestview can be good and bad it’s What you make it, there jobs and school and church. The only down side is that there not really anything for children to do in this town so it easy for kids go down the wrong path. "
    0
    Flag
  • Julia R.
    "wonderful neighbors! Quiet neighborhood. ❤ Beautiful trees and well kept yards. Dogwood Estates is a perfect little gem close to shopping"
    0
    Flag
  • Christian M.
    "20miles one way very traffic congested and lots of accidents ........................................."
    0
    Flag
  • Sheronda M. T.
    "Pretty safe and the neighborhood is very nice everyone is very mindful of each others property. Crestview is a nice place to live and close to the beach. "
    0
    Flag
  • Matt H.
    "Far from everything. Takes 45 minutes to go to a real town with restaurants and shopping areas. Average age is 55+ years old and has no younger community activities. "
    0
    Flag
  • Henrycook76
    "plenty of walking around spaces up and down roads and trails. nice neighbors generally. and easy drives in and out of town "
    0
    Flag
  • Aggie909
    "Very peaceful area. No loud music, no loud kids. Fun during Halloween as this is the spot. Yards are kept up and people are nice."
    0
    Flag
  • Ashton S.
    "Newer housing is well maintained and friendly, the closer to downtown you are the worse you can expect morning commute traffic to be "
    0
    Flag
  • Aggie909
    "Very peaceful place to live. Neighbors are quiet and kids are respectful. No loud parties, or music. I feel safe here overall , even as my husband works overnight. "
    0
    Flag
  • Sylvia R.
    "This is a great area for families but it could use more sidewalks. Plenty of restaurants and a good variety."
    0
    Flag
  • KP
    "Living on the south side makes my drive to Destin about 20 minutes less then living on the north side. "
    0
    Flag
  • Fabphleb
    "40 mins by car through airforce base, with no exits for detours. Not terrible, but not ideal when lanes are closed on highway."
    0
    Flag
  • TD
    "There are many families is this small neighborhood and it is very quiet and pretty, well maintained. "
    0
    Flag
  • Jtjones513
    "I’ve lived in this neighborhood since 1994, many families move in & out real quick if they’re in the military. Fairly quiet & peaceful around here. Not far from highway & I-10, but not too close. "
    3
    Flag
  • CLocK
    "Great community!! Growing city military economic dependency, small town feel. Plenty of churches, plenty of room to expand"
    1
    Flag
  • AS
    "Quaint town with lots of traffic near i10 highway and a small town feel. Sometimes backed up for miles."
    0
    Flag
  • Mjautry
    "Traffic on 85 is awful. It can take 45 minutes to get home. We need more transportation development to keep traffic flowing."
    0
    Flag
  • Galaxymlp
    "I commute very far for work. I commute 46 miles into Pensacola to work everyday. Traffic is light in that direction. "
    0
    Flag
  • Mysticangelsdesires
    "live in neighborhood. military or retired military. easy access to highway 85 and interstate 10. friendly neighborhood. kids play in street. "
    1
    Flag
  • Mfzee
    "I don't know much about the area but what I do know is there are not many places to go shopping in the immediate area. The nearest Target is 40 min away."
    0
    Flag
  • Jerryconesr
    "The area we are at is at the very edge of city limits so you definitely need a vehicle to get to anything. It’s quiet and safe. Don’t really know why but the kids here just hide in their houses all day and night."
    0
    Flag
  • Theqsters
    "neighbors tend to stay to there self its a safe nice neighborhood close to main roads and reasturant "
    1
    Flag

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Apartments for Rent

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Explore by feature - Pet Friendly

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Homes for sale near 103 Winchester Way

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Off Market Homes Near 103 Winchester Way

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