239 Oak Dr, Middletown, DE 19709
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Property image
OFF MARKET

239 Oak Dr
Middletown, DE 19709

  • 4 Beds
  • 2 Baths
  • 3,525 sqft (on 1.25 acres)

$624,700

Trulia Estimate
as of Jul 14, 2026
Est. Refi. Payment $3,611/mo*
Refinance Your Home

$624,700

Trulia Estimate
as of Jul 14, 2026
Est. Refi. Payment $3,611/mo*
Refinance Your Home
4 Beds
2 Baths
3,525 sqft
(on 1.25 acres)

Local Information

  • Map ViewExplore the area around 239 Oak Dr.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

There~S Plenty Of Room To Spare In This 2-Story 5Br, 3-Bth, 2-Kitchen Cape Cod On A 1.25 Acre Lot W/Fenced In Area In Rear Yard And Is With-In Walking Distance To The New St. George~S Vo-Tech High School. Combine Households And Bring The In-Law~S, Or Do You Have A Catering Or In-Home Daycare Business; The 2nd Kitchen Is Ideal For You! On The 1st Floor You'll Enjoy A Casual Living Room With Carpeting, Country Kitchen With Trash Compactor, Walk-In Pantry For Extra Storage, Dishwasher, Refrig, Electric Range, 1St-Floor Laundry, 3 Bedrooms And 2 Updated Baths. On The 2nd Floor Are 2Brs, Full Bath And Two 7 X 10 Storage Closets. The Basement Is Partially Finished, (Drywall Installed) All You~Ll Need To Do Is Add A Drop Ceiling. The In-Law Suite Consists Of County Kitchen, Casual Living Room, Bedroom, And Updated Full Bath. Also Included On The Property Is A Detached 25~X50~ 3 Bay Garage With Workshop Area, Perfect For The Car Enthusiast Or Craftsman. There's Plenty Room For The Rv Or Boat, So Bring Them Too!
239 Oak Dr, Middletown, DE 19709 is a 4 bedroom, 2 bathroom, 3,525 sqft single-family home built in 1989. It last sold for $319,900 on May 7, 2009. It is currently off market. The Trulia Estimate is $624,700, with a rent estimate of $3,308/month.

Home Highlights

Parking
Garage
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 239 Oak Dr

Interior Features

Interior Details
BasementNumber of Rooms: 9Types of Rooms: Family Room
Heating & Cooling
Heating: ElectricAir ConditioningHeating Fuel: Electric
Levels, Entrance, & Accessibility
Stories: 2Floors: Carpet

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: OtherFoundation Type: Crawl Raised
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1989
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Lot Information

Lot Area: 1.25 acres

Price History for 239 Oak Dr

DatePriceEventSource
05/07/2009$319,900Sold
N/A

Market trends in Middletown

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$509K
$28.75KMoM
Sale-to-List Price
99.5%
0.7%MoM
Price per sq ft
$196
$1MoM
Available listings
175
1MoM
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Property Tax and Assessment

Year2025
Tax
Assessment$584,500
Home facts updated by county records

Comparable Sales for 239 Oak Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
315 Beech Ln, Middletown, DE
0.24
Single-Family Home
$550,000
08/28/25
4
3
2,500
319 Pheasant Dr, Middletown, DE
0.39
Single-Family Home
$505,000
01/15/26
4
2.5
3,370
822 Lorewood Grove Rd, Middletown, DE
0.29
Single-Family Home
$190,200
06/11/26
3
2
1,575
776 Lorewood Grove Rd, Middletown, DE
0.40
Single-Family Home
$270,000
10/24/25
3
1.5
1,400
467 Hyetts Corner Rd, Middletown, DE
0.74
Single-Family Home
$375,000
05/25/26
3
2.5
1,900
147 Parker Dr, Middletown, DE
0.63
Single-Family Home
$630,000
09/11/25
4
2.5
3,600
422 Georgiana Dr, Middletown, DE
0.77
Single-Family Home
$570,000
10/02/25
4
2.5
3,450
331 Acasta Dr, Middletown, DE
0.74
Single-Family Home
$515,000
04/27/26
4
3
4,100
300 Fenn Ct, Middletown, DE
0.76
Single-Family Home
$580,000
01/28/26
4
2.5
2,375
313 Acasta Dr, Middletown, DE
0.65
Single-Family Home
$620,000
07/31/25
4
3.5
4,025

Nearby homes

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Assigned Schools

These are the assigned schools for 239 Oak Dr.
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 270 Trulia users voted on each feature.

  • 91 % Say it's dog friendly

  • 89 % Say car is needed

  • 88 % Say parking is easy

  • 85 % Say there are sidewalks

  • 84 % Say yards are well-kept

  • 82 % Say there's holiday spirit

  • 81 % Say it's quiet

  • 77 % Say kids play outside

  • 76 % Say people would walk alone at night

  • 73 % Say streets are well-lit

  • 60 % Say neighbors are friendly

  • 59 % Say they plan to stay for at least 5 years

  • 50 % Say there's wildlife

  • 45 % Say it's walkable to restaurants

  • 44 % Say it's walkable to grocery stores

  • 36 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • H47b4nyc4k
    "Owners frequently curb their dogs then take them on e walk-"
    0
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  • 9f9yws85yn
    "It’s wonderful, everyone is friendly and helpful. The people here are quiet and considerate. There is a good mix of ages, cultures and races. Many people have pride of ownership and care for their property. "
    0
    Flag
  • Trulia User
    "Easy access to NYC via Amtrak from Wilmington. Traffic to get to Wilmington is not terrible. There are also buses available. "
    0
    Flag
  • Unspecified
    "Lived here since 2016. Great place to raise kids. Getting many stores . Roads are good. Community is welcoming. Close to rt 13 and I95. "
    0
    Flag
  • Guzmancortespaul
    "It's very nice to live here, it's a very quiet and cozy place.. Everything is very nice to live in, and the people are very friendly, The stores are very close… It's a historic place, and it has good places to visit. "
    1
    Flag
  • Unspecified
    "Same age group in the neighborhood. Children are of various ages. Elementary to college level but all look out for each other."
    0
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  • Juan Peralta
    "lots of green places for the dogs to roam around. Great pet owners always with their pets with a leash."
    0
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  • jfreeman413
    "There is a bus / carport near my home, but most people drive to work. I work from home, but have taken public transportation to town in the past. It is convenient."
    3
    Flag
  • Trulia User
    "I love living in this area. I think the schools are great and the neighbors are very friendly. Makes me feel good I chose this area. Thanks "
    3
    Flag
  • George C.
    "Neighborhood garage sales, safe surroundings, great schools, churches, and restaurants. Plenty of places to shop"
    1
    Flag
  • Michael J.
    "That dodge are not allowed in this area because they like to poop everywhere and poop stinks very badly"
    0
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  • Gkareliz
    "Lots of dogs, people love dogs in my neighborhood. Animal hospital near by. A large dog park near. One negative is sometimes people do not pick up after their dogs, and many dogs are not trained and seem to rule the owners. "
    16
    Flag
  • Smithnation10
    "yard space is on the small side but the neighborhood is a great walking area that leads to a school that has a track or trail for the dog"
    2
    Flag
  • Lekisha.parker
    "Neighborhood is very nice. Lots of friendly people and our children have made new friends. Very satisfied with the Appo school district as well. "
    3
    Flag
  • Shayla M.
    "Parents should know that the school district is amazing and that this town is up and coming and ready for young families. I just moved here and my sons love that we have parks and lots to do. We have started to try different restaurants in the area all good so far."
    3
    Flag
  • Katherine1rodriguez
    "I lived here for a year and most people are friendly and family oriented. Most families have dogs and children’s. The neighborhood feels safe and it’s clean. Very quiet neighborhood you only see families walking there kids or dogs. "
    11
    Flag
  • Springilove55
    "No traffic , I travel by car and the roads are in good shape . No potholes like Long Island N.Y. I see buses on many roads that are in area , also that go to the mall in Christina De"
    0
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  • Shayla R.
    "I’m not sure I just moved to this area... I hope to learn more about what happens in Middletown. The ppl are friendly though. Great restaurants."
    0
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  • Lillian G.
    "Live here for 3 years with my kids and town is great, people and the school district awesome. "
    0
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  • Vanessa T.
    "My neighborhood is quite,clean and very family oriented. Neighbors stay to themselves and so far the children are mannerly. I hope and pray it remains this way."
    5
    Flag
  • Chorstead
    "Our neighborhood is quaint and everyone is friendly .. also the community areas are friendly as well. "
    0
    Flag
  • T G.
    "The dog owners in my neighborhood like that there is a lot of space for the dogs to walk and run around. What dog owners would not like is that there is no gate to keep the dogs from running away."
    4
    Flag
  • Chrisaez
    "there are dogs everywhere. if your dog is not friendly then you might run into a problem. however, there's enough land for your dog to roam freely. "
    0
    Flag
  • Rollyn
    "Dogs don’t run free. Owners are greeted by neighbors.Larger dogs are welcomed too.Most back yards are fenced."
    5
    Flag
  • C Guy
    "In the Town of Whitehall, you actually know your neighbors and their names. It’s not just a neighborhood but a community. "
    1
    Flag
  • Kayle C.
    "The area has great parks and its neighborhood friendly. schools are pretty close. ⁰00000000000000000000 "
    0
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  • Kaitlyn M.
    "It’s been very safe for the entire time I’ve lived here. Both sides of town have their perks but this side is being built up very nicely. "
    0
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  • Vickiesantino
    "There is no good transportation in Delaware. That is way the roads are so crowded! Everything’s nw is so spread out in Middletown there is no easy way to get anywhere without a car!"
    16
    Flag
  • Amanda H.
    "Middletown is booming! Keeping its small town feel, but with convenient shops nearby, and a great dog park. Hard to imagine ever leaving!"
    0
    Flag
  • Liabeaufort
    "Local bbqs, trick or treating, parades, good schools and great teachers. Elementary school does a book drive delivering books to neighborhoods "
    1
    Flag
  • Bibi.li.sita
    "I live on a block that only 6 houses on it. It’s great!!! The people are friend and watch out for each other "
    0
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  • Paige O.
    "Quick to get anywhere in town. Traffic is heavy near schools and through the center of town. Easy to get to most places though."
    0
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  • Bibi.li.sita
    "Peach feast, big ball, little shops everywhere. It’s an awesome area to live in. They always have family events "
    2
    Flag
  • Ankit2shahi
    "Good for kids. Good for halloween, trick or treat. Good privacy n safety for kids and elderly. Neighbours mind their own business, without interfering too much"
    3
    Flag
  • Amanda H.
    "Great public playground with dog park, more than four quality grocery stores in a five mile radius, and some of the best public schools around!"
    0
    Flag
  • Becky
    "School district is best in Delaware. Very diverse due to job transfers or job relocation. Very family friendly."
    0
    Flag
  • James T.
    "Peach festival is an annual fav and well attended. Fair at Catholic Church as well. Christmas decorating of light poles "
    0
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  • Trulia User
    "The options for schools In the area are the best in the state. That was the main reason for my family relocating. "
    0
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  • Rogercthornton
    "Holiday parade is a great annual event. Very old times town center (quaint) and friendly. Family friendly "
    0
    Flag
  • Ericka R.
    "New elementary school opening September 2019 New community center coming soon Postal store will be located closer than post office as well"
    0
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Apartments for Rent

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Homes for sale near 239 Oak Dr

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Off Market Homes Near 239 Oak Dr

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