263 Ann Dr, Middletown, DE 19709
OFF MARKET

263 Ann Dr
Middletown, DE 19709

  • 4 Beds
  • 2.5 Baths
  • 1,900 sqft

$441,100

Trulia Estimate
as of Jul 30, 2026

$441,100

Trulia Estimate
as of Jul 30, 2026
4 Beds
2.5 Baths
1,900 sqft

Local Information

  • Map ViewExplore the area around 263 Ann Dr.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2011
Living Area
1,900 sqft
Price/Sqft
$232
Parking
Garage

About this House

Superb 4BR colonial located in cul-de-sac and backing to woods in the ever popular Crosslands at the Canal! Hardwood foyer, spacious family room w/fireplace, oversized country kitchen w/recessed lighting and loads of counter and cabinet space, owners suite w/walk-in closet, 2 car garage, full basement with window egress, rear deck backing to woods and so much more! Priced under market to account for a little paint, carpet and your finishing touches! Don't miss this gem!!
263 Ann Dr, Middletown, DE 19709 is a 4 bedroom, 3 bathroom, 1,900 sqft single-family home built in 2011. It last sold for $385,000 on Mar 15, 2023. It is currently off market. The Trulia Estimate is $441,100, with a rent estimate of $2,916/month.

Home Details for 263 Ann Dr

Interior Features

Interior Details
BasementNumber of Rooms: 8Types of Rooms: Dining Room
Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Carpet
Fireplace & Spa
Fireplace

Exterior Features

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

Property Information

Year Built
Year Built: 2011
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Lot Information

Lot Area: 9583 sqft

Price History for 263 Ann Dr

DatePriceEventSource
03/15/2023$385,000Sold
Bright MLS #DENC2037456
02/03/2023$379,900PendingBright MLS #DENC2037456
02/01/2023$379,900Listed For SaleBright MLS #DENC2037456
08/31/2017$295,000Sold
N/A
07/31/2017$295,000PriceChange
Agent Provided
07/14/2017$305,000Listed For SaleAgent Provided
07/15/2011$256,329Sold
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$444,900
Home facts updated by county records

Comparable Sales for 263 Ann Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
267 Ann Dr, Middletown, DE
0.03
Single-Family Home
$552,000
07/17/26
4
2.5
2,250
248 Ann Dr, Middletown, DE
0.08
Single-Family Home
$479,900
06/30/26
4
3
1,900
265 Ann Dr, Middletown, DE
0.01
Single-Family Home
$575,000
03/27/26
4
3.5
2,875
300 Fenn Ct, Middletown, DE
0.14
Single-Family Home
$580,000
01/28/26
4
2.5
2,375
422 Georgiana Dr, Middletown, DE
0.16
Single-Family Home
$570,000
10/02/25
4
2.5
3,450
147 Parker Dr, Middletown, DE
0.24
Single-Family Home
$630,000
09/11/25
4
2.5
3,600
445 Georgiana Dr, Middletown, DE
0.20
Single-Family Home
$565,000
09/26/25
5
3.5
2,900
142 Parker Dr, Middletown, DE
0.27
Single-Family Home
$675,000
11/07/25
5
5
4,375
102 Parker Dr, Middletown, DE
0.38
Single-Family Home
$749,000
01/23/26
4
3.5
4,250
331 Acasta Dr, Middletown, DE
0.79
Single-Family Home
$515,000
04/27/26
4
3
4,100

Nearby homes

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Assigned Schools

These are the assigned schools for 263 Ann 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
    Flag
  • 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
    Flag
  • Juan Peralta
    "lots of green places for the dogs to roam around. Great pet owners always with their pets with a leash."
    0
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • Lillian G.
    "Live here for 3 years with my kids and town is great, people and the school district awesome. "
    0
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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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Homes for sale near 263 Ann Dr

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Off Market Homes Near 263 Ann Dr

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