$1,434,751Average Value$816Average Price per Sq Ft15Homes For Sale
One of San Diego's historic hillside communities
Middletown has come a long way from its founding in 1850. Its hillside location, overlooking San Diego Bay, made it a natural landing point for many Italian and Portuguese fishermen. By the early 1900s, its water views and proximity to the developing city center led to its transformation from a humble fishing village to a home for Craftsman and Spanish Revival mansions. "People are drawn to the historic nature of this area. There are so many homes built over 100 years ago that are still just as pretty as the day they were finished," says Joe Carta of Joe Carta Realty, who's been selling in San Diego since the 1980s. As the city grew, it added a layer of urban convenience to this primarily residential neighborhood. Carta says, "This area is infused with commercial districts, which feels unique for a neighborhood this old to have walkable restaurants and cafes."
An elevated view of Middletown overlooking San Diego Bay shows the proximity to downtown as well
Architectural styles vary in Middletown; however, Spanish influence is ubiquitous.
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1920s homes and contemporary hillside mansions
Despite its city location, homes on the steep streets of Middletown sit on relatively spacious lots with grassy front and backyards full of palms and other coastal foliage. Different waves of architecture can be seen throughout the neighborhood, but the 1920s homes are the most prominent. They take the form of small bungalows, larger Craftsman with ornate woodwork and grand Spanish Revivals with breezy verandas and red-tile roofs. These historic homes aren't on the market often, but when they are, they range from $1 million to $2 million. The neighborhood hasn't physically grown over the years, but it's seen the addition of newer homes, like 1980s contemporary designs with white-stucco exteriors, rounded walls and cylindrical extensions wrapped with tall windows. These designs vary from midsize homes to walled hillside mansions with water views that can cost $1 million to $3 million. Large duplexes in the neighborhood can cost $1 million to $2 million. There are also condos ranging from $500,000 to $1 million for luxury units overlooking the bay.
Some homes in Middletown have a view of the San Diego Bay.
Craftsman style homes feature soaring A-frame roofs.
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A-rated San Diego Unified School District
The neighborhood is part of the San Diego Unified School District, which Niche grades an A overall. Students may go to the Grant School, graded an A-minus, for kindergarten through eighth grade. They finish at A-minus rated Point Loma High, about 4 miles west of most homes. Point Loma students can explore professions through career-focused classes like Introduction to Engineering and Principles of Biomedical Science.
Elevate learning at Grant K-8, where every day unfolds a new adventure.
An entrance view to Point Loma High School located in Point Loma Heights.
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Gelato shops and seafood markets on India Street
Residents can walk down the hill to India Street, which offers a row of restaurants on the neighborhood's west side. Spots like Gelato Vera Caffe keep the neighborhood's Italian roots alive. Folks often enjoy an espresso at the sidewalk tables. Blue Water Seafood Grill & Market takes advantage of the proximity to the bay by serving traditional seafood dishes made with the fresh catch they sell at their seafood counter. Shakespeare Pub is a casual British-inspired bar that's become a popular place to watch soccer matches. For fine dining, the Wine Vault & Bistro offers a fixed menu with wine pairings. Some of the city's hottest eateries, such as Farmer's Bottega and Harley Gray Kitchen & Bar, are just north of the neighborhood on Goldfinch Street. There's also a Vons near these restaurants for groceries, less than a mile from many homes.
Many food choices line the streets of India Street located in Middletown such as Rubicon Deli.
Customers enjoy delicious seafood from Blue Water Seafood Market & Grill in Middletown.
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Harper's Topiary Garden and nearby parks
Middletown's streets are home to some impressive greenery. Most notable is Harper's Topiary Garden, a grand arrangement of hedges in somebody's front yard. Years ago, the owners of this hillside Union Street mansion decided to take advantage of their steep, spacious front lawn by filling it with over 50 tall hedges that are hand-trimmed into different figurines. People come from all over the city to see the display. Residents often visit Pioneer Park for recreation just north of the neighborhood, across West Washington Street. It has a playground, ample lawn space and a paved walking loop shaded by large trees. Mission Hills Park offers more walking trails across from Pioneer Park. Balboa Park—the city's most prominent recreation space—is 4 miles east. This 1,200-acre park is also home to the San Diego Zoo. Plus, Ocean Beach is 6 miles west.
Pioneer Park features ample green space and a playground.
Harper's Topiary Garden located in Middletown is a must see for San Diego. It features intricate trimmed bushes with distinguished characters.
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San Diego International Airport next to the neighborhood
Commuters can take Interstate 5 for their daily drive, which runs down the neighborhood's west side. Downtown San Diego is 2 miles south on the 5. San Diego Naval Base is 6 miles south, and Naval Air Station North Island is 7 miles away across the Coronado Bridge from the base. Folks can also catch a bus to downtown at stops on Reynard Way. Scripps Mercy Hospital is the nearest major medical facility, about 2 miles northeast. The San Diego International Airport is just west of the neighborhood, no more than 2 miles from most homes.
An elevated view of Middletown shows the tidy neighborhood streets and lush landscapes.
San Diego International Airport is conveniently close by, just south of Middletown.
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Middletown Demographics and Home Trends
On average, homes in Middletown, San Diego sell after 46 days on the market compared to the national average of 53 days. The median sale price for homes in Middletown, San Diego over the last 12 months is $1,250,000, down 10% from the median home sale price over the previous 12 months.
Perched above the city in one of San Diego’s most desirable Midtown locations, this stunning residence offers panoramic views that stretch across the entire San Diego Bay, from Coronado Island to Downtown and beyond. Experience the beauty of the skyline, ocean, and harbor from every room in the home, day and night. Inside, you’ll find fresh updates throughout, including new paint and flooring
3519 Andrews St, a stunning condo-townhouse nestled in the vibrant heart of the Mission Hills/Middletown area of San Diego, CA. This spacious 1,553 square foot home offers an ideal blend of modern living and urban convenience. With 3 bedrooms and 3 full bathrooms, this residence is perfect for those seeking comfort and style with OWNED SOLAR to keep electricity bills low and a HUGE BONUS you have
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Experience the perfect blend of historic charm and modern sophistication at Columbia Studios, a fully gated 12-unit property in the highly desirable Bankers Hill neighborhood of San Diego. The offering includes a beautifully renovated 1938 building featuring spacious one- and two-bedroom units, alongside a brand-new, all-electric studio building completed in 2025. Each unit offers premium
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This centrally located, charming, and clean apartment home is now available. The 1 bedroom 1 bathroom boasts hardwood floors, ample storage, and an updated bathroom. The unit's amenities include private laundry on-site, and your own parking spot with off-street parking as well. The lot is shared with one other unit with only one adjoining wall.
Located in the Old Town/Mission Hills area of San Diego, we are sited in a wooded area overlooking Lindberg Field and San Diego Harbor, and above the India Street colony near Washington and India Streets. We feature small, unfurnished studios and studio alcoves. The alcoves are larger studios with separate living room and bedroom set-ups. We are at the top of a big hill, but are close to all
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