5000 Windsor Rd, Middletown, OH 45044
OFF MARKET

5000 Windsor Rd
Middletown, OH 45044

  • 4 Beds
  • 2 Baths
  • 1,638 sqft (on 1.50 acres)

$255,600

Trulia Estimate
as of Aug 19, 2026
Est. Refi. Payment $1,642/mo*
Refinance Your Home

$255,600

Trulia Estimate
as of Aug 19, 2026
Est. Refi. Payment $1,642/mo*
Refinance Your Home
4 Beds
2 Baths
1,638 sqft
(on 1.50 acres)

Home Value

Trulia Estimate
$256K
Since last month
Decreased$7K (-2.7%)
Since last year
Increased$23K (+9.9%)
Since last sale
Increased$157K (+159.5%)
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 +152% in the last 10 years
MonthEstimated value
2026
August 2026$256K
July 2026$263K
June 2026$264K
May 2026$261K
April 2026$244K
March 2026$246K
February 2026$236K
January 2026$235K
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
5003 Windsor Rd, Middletown, OH
0.07
Single-Family Home
$197,000
04/24/26
3
1
1,116
2481 Cincinnati Dayton Rd, Middletown, OH
0.33
Single-Family Home
$209,900
01/07/26
3
2
1,474
2511 El Camino Dr, Middletown, OH
0.43
Single-Family Home
$240,000
12/10/25
4
2
1,536
4712 Lefferson Rd, Middletown, OH
0.44
Single-Family Home
$173,000
09/10/25
3
1.5
1,368
2001 Kenway Pl, Middletown, OH
0.30
Single-Family Home
$225,000
10/29/25
3
2
1,200
4708 Lefferson Rd, Middletown, OH
0.45
Single-Family Home
$234,900
05/29/26
3
2
1,248
1613 Kenway Pl, Middletown, OH
0.34
Single-Family Home
$224,000
08/07/26
3
1.5
1,339
2510 El Camino Dr, Middletown, OH
0.43
Single-Family Home
$320,000
05/07/26
3
2.5
1,536
2413 Buckingham Ct, Middletown, OH
0.48
Single-Family Home
$160,000
05/12/26
3
1.5
1,108
1904 Kenway Pl, Middletown, OH
0.36
Single-Family Home
$215,000
06/05/26
3
2
1,029

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
4918 Windsor Rd, Middletown, OH 45044
0.03
$273,800
4
2
1,316
Off Market
5003 Windsor Rd, Middletown, OH 45044
0.07
$197,000
3
1
1,116
Recently Sold
S Dixie Hwy, Franklin, OH 45005
0.18
-
-
-
-
Off Market
4902 Roosevelt Ave, Middletown, OH 45044
0.23
$177,400
2
1
1,105
Off Market
4924 Lefferson Rd, Middletown, OH 45044
0.24
$239,400
3
2
1,534
Off Market
2001 Kenway Pl, Middletown, OH 45044
0.30
$225,000
3
2
1,200
Recently Sold
1625 Kenway Pl, Middletown, OH 45042
0.30
$310,400
4
2
1,572
Off Market
1805 Kenway Pl, Middletown, OH 45044
0.32
$245,000
3
2
1,177
Off Market
1901 Kenway Pl, Middletown, OH 45044
0.33
$416,700
3
2.5
1,911
Off Market
1613 Kenway Pl, Middletown, OH 45044
0.34
$224,000
3
1.5
1,339
Recently Sold
2481 Cincinnati Dayton Rd, Middletown, OH 45044
0.33
$209,900
3
2
1,474
Recently Sold
2002 Kenway Pl, Middletown, OH 45044
0.35
$246,000
3
2
1,200
Off Market

Local Information

  • Map ViewExplore the area around 5000 Windsor Rd.
  • Schools1 Preschool School2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1933
Lot Size
1.5 acres
Living Area
1,638 sqft
Price/Sqft
$156
Parking
Garage

About this House

One of the very limited homes in Middletown with land. 1.5 acres on a wooded lot in the city limits. Many recent updates to a home that sold for over $188,000 in 2005, and is only $109,900 now. Roof, water heater, furnace, A/C, sump pump, and septic lines are all recently new. Bedroom on the first floor! Oversized garage, really nice screened in porch and patio. Storage shed and peach trees are also in the back yard! Come now before this rare land fine in Middletown is gone! House does need a little work, but you won't find another house like this anywhere!
5000 Windsor Rd, Middletown, OH 45044 is a 4 bedroom, 2 bathroom, 1,638 sqft single-family home built in 1933. It last sold for $98,500 on Jul 17, 2015. It is currently off market. The Trulia Estimate is $255,600, with a rent estimate of $2,484/month.

Home Details for 5000 Windsor Rd

Interior Features

Interior Details
BasementNumber of Rooms: 7Types of Rooms: Walk In Closet, Breakfast Nook, Dining Room, Family Room, Pantry, Recreation Room, Solarium Atrium, Sun Room
Heating & Cooling
Heating: GasAir ConditioningCooling System: CentralHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 2Floors: Carpet, Hardwood, Laminate
Appliances & Utilities
Cable ReadyMicrowaveRefrigerator

Exterior Features

Exterior Home Features
Roof: OtherExterior: Wood
Parking & Garage
GarageParking Spaces: 2Parking: Garage Detached

Property Information

Year Built
Year Built: 1933Year Updated: 2008
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 1.50 acres

Price and Tax history

DateEventPrice
Jul 17, 2015
Source: Cincy MLS #1447451
Sold
$98,500
Sep 16, 2014
Source: Agent Provided
ListingRemoved
$119,900
Aug 22, 2014
Source: Agent Provided
PriceChange
$119,900
Price decreased by 4%
Jul 8, 2014
Source: Agent Provided
PriceChange
$125,000
Price decreased by 6%
Jun 19, 2014
Source: N/A
PriceChange
$132,900
Price decreased by 5%

Market trends in Middletown

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$235K
$18.96KMoM
Sale-to-List Price
100.0%
Price per sq ft
$169
$16MoM
Available listings
231
11MoM

Around this home

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 Middletown

At least 379 Trulia users voted on each feature.

  • 84 % Say car is needed

  • 79 % Say yards are well-kept

  • 78 % Say parking is easy

  • 75 % Say there are sidewalks

  • 71 % Say it's dog friendly

  • 68 % Say there's holiday spirit

  • 66 % Say kids play outside

  • 48 % Say neighbors are friendly

  • 48 % Say streets are well-lit

  • 45 % Say it's quiet

  • 42 % Say there's wildlife

  • 41 % Say people would walk alone at night

  • 39 % Say it's walkable to restaurants

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

  • 31 % Say it's walkable to grocery stores

  • 22 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Kristie LeVangie
    "We have a block of park right across the street with plenty of room for dog walks. "
    0
    Flag
  • Pattifam4u
    "Sidewalks and good neighborhoods to walk"
    0
    Flag
  • Trulia User
    "Public transit and commute downtown is quick. Nice drive by the park, 4 gas stations on the same street. Low crime and a public school around the corner."
    1
    Flag
  • Brooklynn.heilgeist
    "Nice some people will take their dogs for walks and their children some sidewalks are on maintained others are maintained. Depends on the neighborhood."
    0
    Flag
  • Trulia User
    "Nice and easy most days the lines could use some repainting and pot holes are a issue But there is a bus"
    0
    Flag
  • Ptghhcj6bz
    "I’m new to the area and I don’t have any advice on the specifics of this particular area but I’m going to be positive about it "
    0
    Flag
  • Brenda Stevens Lindsey
    "To many stray cats and loose dogs. People don’t control their dogs behavior , dogs need to be on a leash no matter what "
    0
    Flag
  • Lindsay Potts
    "It’s Middletown - 30 minutes to get anywhere. But close to highways, it’s just where the city falls between more industrious areas."
    0
    Flag
  • Lindsay
    "Lots of foot traffic, crime. It doesn’t feel safe to go outside at night. Especially by yourself. Packages are frequently stolen and/or delivered to the wrong place. "
    0
    Flag
  • Kmedmonds57
    "I have lived in this neighborhood for almost 2 years very convenient lots of stores around and I’m right in the heart of everything I just wish public transportation was a little better in school. Districk was better as well. I would choose to have more restaurants family are near."
    0
    Flag
  • Trulia User
    "The city bus runs all throughout my neighborhood. There are several stops down central avenue and it’s only 5 minutes from downtown…………………….."
    1
    Flag
  • Trulia User
    "Very quiet area nice schools and very friendly neighbors never had a problem from anybody. Would move back "
    0
    Flag
  • Trulia User
    "I’ve lived here for 8 years and I love it. Not too many younger people live around here so it’s pretty quiet"
    1
    Flag
  • Pamela C.
    "Have to be on a leash and pick up poop. It’s a quiet neighborhood so barking all the time or at night is bad. "
    8
    Flag
  • Regina W.
    "This is a family friendly neighborhood but it is not very diverse. It is getting better. I would definitely recommend living here!"
    1
    Flag
  • Pamela C.
    "Quiet and private and park with trees. It’s has good and bad sections. I guess I live in the good section. "
    0
    Flag
  • Trulia User
    "nothing is unique about this neighborhood. I have 2 neighbors that live across the street who are lovely and always watching out for one another. "
    1
    Flag
  • Jillakplay
    "Great schools friendly neighborhood everyone takes care of homes. Lots of kids playing on the many cul de sacs"
    0
    Flag
  • Donald L.
    "Owners need to clean up after their own dogs. Make sure that their dogs are on a leash when walking them. Owners are able to control them. If in their yard, they need chained up or fenced in. But can't reach out of their yard. All basic animal etiquette we have learned all our life. You are responsible fir your animal."
    1
    Flag
  • Erzsm00
    "the bullying in the sxhools and fighting in the middle and high school is terrible very lite interventiom from staff either utterly disgusting"
    4
    Flag
  • Pamela C.
    "Certain parts of Middletown is nice and some parts not so much. Just make sure you look at the area and do research. "
    3
    Flag
  • Saylorpatrickk
    "Very easy! The public transportation is also very close by in most neighborhoods. Most people use cars but walking is also an option"
    0
    Flag
  • Nevilleconnie99
    "We really don’t have anything honestly. Middletown is not family friendly and we can’t wait to move "
    6
    Flag
  • Chelsey0902
    "This neighborhood has its friendly areas which are the older families that have been here for 20+ years. However over the years it has become overrun with homeless and drugs. "
    0
    Flag
  • Diane L. D.
    "parents shouldn't let their kids run around by themselves because of the stray animal's. i also think maple park is a great community to raise a family ..... "
    2
    Flag
  • Devona V.
    "That there are a lot of great neighborhoods and great families in Middletown for many years it has been a decent place to raise your children."
    4
    Flag
  • Brian M.
    "Lived here all my life & have had some great experiences. It could be better but overall it’s not a bad place to live."
    0
    Flag
  • Jennifer M.
    "I love the little fairs that are all around, not just here but in Hamilton. The sky diving adventures is really neat. I don't know what else to say. Our area is riddled with drugs but there are a lot of normal ppl here that are good hearted and make it enjoyable."
    8
    Flag
  • Jeren K.
    "this area has eazy access to interstate 75. there are a lot of food and shopping options in the area. roads could be better maintained, especially the main roads. "
    0
    Flag
  • Barb M
    "I love Middletown! really a half hour from everywhere very safe and beautiful I am very happy here."
    4
    Flag
  • Arthur
    "butler county has always been good in my opinion about building a great community. Middletown has its pros and cons like any other community. We have lived here for 5 years now and we love it, we have gotten to know our neighbors and we have lots of family that lives close by. We look out for one another and take pride in our properties and community. I'm glad we came."
    6
    Flag
  • Jrieman
    "movie night outdoors, fourth of july, playgrounds, dog park, kids sporting events, rent a wrestler, football games"
    0
    Flag
  • Jake H.
    "I moved here 4 years ago and things seem to be getting better. My neighbors are great and I don’t have any issues. I guess it’s based on where you live in Middletown."
    0
    Flag
  • Adrienne Paolini
    "We have lived here a little over a year. Most folks are nice. Schools are not very highly rated. Definitely need a car."
    0
    Flag
  • Lila Jane
    "We have been on the same street for almost 10 years now. You get to know the long term neighbors, ecspecially the older ones who need help time to time. I live right around Mayfield Elementary. Some people don't like the noise of children playing. I Love it"
    4
    Flag
  • Grubbsb30
    "is it a very good town. police is good. great schools and best of all has plenty things to do outside with family or friends "
    1
    Flag
  • Jennifer B.
    "we have block parties and festivities at the park open to everyone. even free lunches in the summer. love it so much"
    2
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 5000 Windsor Rd

  • What is 5000 Windsor Rd estimated to be worth?
    Trulia's estimated value for 5000 Windsor Rd in Middletown, OH is $255,600.
  • What is the price history for 5000 Windsor Rd?
    5000 Windsor Rd in Middletown, OH last sold for $98,500 in July 2015.
  • Is Middletown a buyer's or seller's market?
    Middletown is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Middletown?
    The median sale price in Middletown is $235K. That is up $18.96K from the prior month.
  • Does 5000 Windsor Rd have air conditioning?
    Yes, 5000 Windsor Rd in Middletown, OH has air conditioning.
  • How big is the lot at 5000 Windsor Rd?
    The lot at 5000 Windsor Rd in Middletown, OH is about 1.5 acres.

Explore by feature - Pet Friendly

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Off Market Homes Near 5000 Windsor Rd

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Homes for sale near 5000 Windsor Rd

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