*PROFESSIONAL PICTURES COMING SOON* Welcome to 265 Ann Drive in Middletown — a completely renovated home offering stunning modern farmhouse style, privacy, space and an unbeatable location. This stunning property has been thoughtfully updated throughout the sellers’ ownership with bright, modern farmhouse finishes that create a warm yet elevated feel from the moment you step inside. Luxury vinyl plank flooring flows seamlessly throughout the main living areas, providing both durability and style — with original hardwood floors still preserved underneath for future options. The main level offers light-filled living spaces designed for both everyday comfort and entertaining. The fully finished basement expands your living space even further, featuring beautiful exposed ceiling beams that add character and charm, along with a full bathroom — making it the perfect space for a guest suite, home gym, media room, or additional family room. Step outside and you’ll find a private backyard retreat. The expansive stone patio is ideal for gatherings and summer evenings, enhanced by solar-powered lighting that creates the perfect ambiance. Wrought iron fencing surrounds the yard, and privacy trees have been thoughtfully planted along the perimeter. The lot backs to open space and a tree line, offering both scenic views and added seclusion. Practical features include a two-car garage and a spacious four-car driveway, providing plenty of parking for family and guests. Location is everything — and this home delivers. Situated just five minutes from Delaware Route 1, commuting and travel are incredibly convenient. You’re only minutes from St. Georges Technical High School, shopping and dining at Christiana Mall, and the growing town of Middletown, known for its expanding restaurant scene, local businesses, and small-town charm. Completely renovated, privately situated, and perfectly located — 265 Ann Drive is truly move-in ready and offers the best of modern living in one of Middletown’s most convenient settings.
Sold for $575,000
$575,000
265 Ann Dr, Middletown, DE 19709
4beds
2,875sqft
Single Family Residence
Built in 2011
8,276 Square Feet Lot
$584,500 Zestimate®
$200/sqft
$3,551 Estimated rent
Home value
$584,500
$526,000 - $649,000
$3,551/mo
Zestimate® history
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$3,645/mo
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List your homeWhat's special
Wrought iron fencingFully finished basementBeautiful exposed ceiling beamsLight-filled living spacesBright modern farmhouse finishesExpansive stone patioSolar-powered lighting
Zillow last checked:
Listing updated:
Listed by:
Maddie Justison 302-650-2944,
Crown Homes Real Estate
Bought with:
Maddie Justison, RS0025883
Crown Homes Real Estate
Source: Bright MLS,MLS#: DENC2097326
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 4
- Full bathrooms: 3
- 1/2 bathrooms: 1
- Main level bathrooms: 1
Rooms
- Room types: Living Room, Dining Room, Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 1, Bathroom 1, Bathroom 2, Bonus Room, Half Bath
Bedroom 1
- Level: Upper
Bedroom 2
- Level: Upper
Bedroom 3
- Level: Upper
Bedroom 4
- Level: Upper
Bathroom 1
- Level: Upper
Bathroom 1
- Level: Lower
Bathroom 2
- Level: Upper
Bonus room
- Level: Lower
Dining room
- Level: Main
Half bath
- Level: Main
Living room
- Level: Main
Heating
- Central, Natural Gas
Cooling
- Central Air, Electric
Appliances
- Included: Dishwasher, Disposal, Stainless Steel Appliance(s), Gas Water Heater
- Laundry: Main Level
Features
- Crown Molding, Dining Area, Exposed Beams, Family Room Off Kitchen, Formal/Separate Dining Room, Eat-in Kitchen, Kitchen - Gourmet, Kitchen Island, Pantry, Primary Bath(s), Recessed Lighting, Upgraded Countertops
- Flooring: Hardwood, Luxury Vinyl, Carpet, Wood
- Basement: Finished
- Number of fireplaces: 1
- Fireplace features: Brick
Interior area
- Total structure area: 2,875
- Total interior livable area: 2,875 sqft
- Finished area above ground: 2,875
- Finished area below ground: 0
Property
Parking
- Total spaces: 6
- Parking features: Garage Faces Front, Asphalt, Attached, Driveway, On Street
- Attached garage spaces: 2
- Uncovered spaces: 4
Accessibility
- Accessibility features: None
Features
- Levels: Two
- Stories: 2
- Pool features: Community
- Fencing: Wrought Iron
- Has view: Yes
- View description: Trees/Woods
Lot
- Size: 8,276 Square Feet
- Features: Backs - Open Common Area, Backs to Trees, Cul-De-Sac, Front Yard, Private
Details
- Additional structures: Above Grade, Below Grade
- Parcel number: 13003.40262
- Zoning: S
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence
Materials
- Vinyl Siding
- Foundation: Concrete Perimeter
Condition
- New construction: No
- Year built: 2011
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Community & HOA
Community
- Subdivision: Crossland At Canal
HOA
- Has HOA: Yes
- Amenities included: Clubhouse, Fitness Center, Pool
- Services included: Snow Removal, Pool(s), Common Area Maintenance, Health Club
- HOA fee: $195 quarterly
- HOA name: ASSOCIATION MID ATLANTIC
Location
- Region: Middletown
Financial & listing details
- Price per square foot: $200/sqft
- Tax assessed value: $456,400
- Annual tax amount: $3,587
- Date on market: 2/19/2026
- Listing agreement: Exclusive Agency
- Listing terms: Conventional,Cash,FHA,VA Loan
- Inclusions: See Disclosures
- Exclusions: Washer & Dryer. Dining Room Chandelier (will Be Replaced With Chandelier To Match One In Adjacent Living Room)
- Ownership: Fee Simple
Price history
| Date | Event | Price |
|---|---|---|
| 3/27/2026 | Sold | $575,000$200/sqft |
Source:  Bright MLS #DENC2097326 Report a problem | ||
| 2/26/2026 | Pending sale | $575,000$200/sqft |
Source: Bright MLS #DENC2097326 Report a problem | ||
| 2/19/2026 | Listed for sale | $575,000+93%$200/sqft |
Source: Bright MLS #DENC2097326 Report a problem | ||
| 4/20/2017 | Sold | $298,000-2.3%$104/sqft |
Source: Public Record Report a problem | ||
| 3/4/2017 | Listed for sale | $305,000+6.3%$106/sqft |
Source: RE/MAX Associates-Newark #6938483 Report a problem | ||
| 10/4/2011 | Sold | $286,992$100/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | -- | $456,400 +380.9% |
| 2024 | $3,294 +9.8% | $94,900 |
| 2023 | $3,000 +8.9% | $94,900 +13.2% |
| 2022 | $2,756 +0.1% | $83,800 |
| 2021 | $2,753 -0.4% | $83,800 |
| 2020 | $2,763 +0.2% | $83,800 |
| 2019 | $2,758 +8.4% | $83,800 |
| 2017 | $2,544 +12.1% | $83,800 |
| 2016 | $2,269 | $83,800 |
| 2015 | $2,269 -0.1% | $83,800 |
| 2014 | $2,272 | $83,800 |
| 2013 | -- | $83,800 |
| 2012 | -- | $83,800 +1189.2% |
| 2011 | -- | $6,500 |
| 2010 | -- | $6,500 |
| 2009 | -- | $6,500 |
| 2008 | -- | $6,500 |
Find assessor info on the county website
Neighborhood: 19709
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Nearby schools
GreatSchools rating
- 3/10Southern Elementary SchoolGrades: K-5Distance: 2.6 mi
- 3/10Bedford (Gunning) Middle SchoolGrades: 6-8Distance: 2.5 mi
- 2/10Penn (William) High SchoolGrades: 9-12Distance: 10 mi
Schools provided by the listing agent
- Middle: Gunning Bedford
- High: William Penn
- District: Colonial
Source: Bright MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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Estimated market value
$584,500
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Estimated market value
$584,500
- Delaware
- New Castle County
- Middletown
- 19709
- 265 Ann Dr
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