$1,414,917Average Value$803Average Price per Sq Ft17Homes 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.
GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
View GreatSchools Rating Methodology
Are you familiar with the Middletown neighborhood?
to let others know what life in this neighborhood is like.
Crime and Safety
1 - Low Crime, 10 - High Crime
Middletown
US
Homicide
3
4
Sexual Assault
4
4
Assault with Weapon
4
4
Robbery
4
4
Burglary
5
4
Motor Vehicle Theft
5
4
Larceny
6
4
Crime Score
4
4
Source: WhatIsMyCrimeRisk.com
Middletown Demographics and Home Trends
On average, homes in Middletown, San Diego sell after 37 days on the market compared to the national average of 56 days. The median sale price for homes in Middletown, San Diego over the last 12 months is $1,175,900, down 5% from the median home sale price over the previous 12 months.
Exceptional custom craftsmanship meets modern luxury in one of San Diego's most coveted neighborhoods. Built in 2007 and extensively upgraded, this stunning 4-bedroom, 4-bath residence offers soaring ceilings, elegant travertine floors, multiple fireplaces, and a Viking chef's kitchen designed for everyday living and effortless entertaining. The west-facing view deck becomes your private
Rarely does a property come to market with a story this layered. Harper's Topiary Garden at 3547 Union St is a Mission Hills landmark. A 1939 single family home with a 1914 casita, set on 13,142 sq ft of terraced grounds featuring a decades-old topiary garden tended by the same family for generations. Featured in San Diego Magazine, Hidden San Diego, and viral across social media, this is one of
Welcome to this beautifully upgraded 3 bedroom home offering stunning bay and city views! The open-concept main living space is designed for both everyday living and entertaining, featuring a gorgeous kitchen with a large island with bar seating, generous counter space, stainless steel LG appliances, a breakfast nook, and a dining area that flows seamlessly into the entertainer's living room and
Rare 4-unit investment opportunity with breathtaking panoramic city, bay, and harbor views. Consistently rented with strong income potential, this property features four 2-bedroom, 1-bath units, each with its own one-car garage, plus a community laundry room. Designed for low-maintenance ownership in an unbeatable location, two units have been remodeled with modern updates, while the remaining
Sabrina OrtegaPacific Sotheby's International Realty
Rarely available South Mission Hills Craftsman featuring three separate residences: a studio with floor-to-ceiling windows and unobstructed canyon views toward Bankers Hill and downtown, a spacious one-bedroom/one-bath, and a front two-bedroom/one-bath with peek views of the bay, downtown, Point Loma, and the airport. All units are privately entranced. Original period lighting, sconces, preserved
The STATETHORN is an architectural two-story Streamline Moderne inspired duplex, perfectly positioned in highly desirable South Mission Hills. It presents classic San Diego character, premium hillside appeal, and spectacular ocean vistas of the Bay and Downtown. This residence is sited on a corner lot where State Street and W Thorn Street intersect, providing two different addresses and separate
Brand-New Remodel | 4 Bed, 4 Bath San Diego Home with Breathtaking Panoramic Bay & Ocean Views. Discover elevated living in this meticulously remodeled residence, where unobstructed panoramic views of the bay, ocean, and sparkling city lights take center stage. Stunning 4-panel sliding doors open seamlessly to a expansive wraparound balcony and multiple outdoor entertaining spaces—perfect for
This turnkey 2-bedroom, 2-bathroom Mission Hills residence beautifully blends historic character with modern luxury, featuring rich wood flooring, refurbished windows, and a stunning, iconic Batchelder tile fireplace. Beyond the main home’s exceptional curb appeal and light-filled interiors, the property offers rare and highly versatile advantages: a fully finished detached bonus space perfect
Welcome to 3515 Union Street, a stunning architectural residence in the heart of Mission Hills, one of San Diego’s most coveted neighborhoods. Spanning approximately 4,600 square feet, this exceptional 4-bedroom, 3.5-bath home offers an elevated living experience defined by scale, light, and breathtaking views. Step inside to soaring 20-foot ceilings that create a dramatic first impression,
If you are looking for a unique, turnkey home that offers both charm and an abundance of outdoor living space, this 1920s gem—nestled in a private, four-home canyon cul-de-sac—is the perfect sanctuary. This delightful property places you at the heart of San Diego’s best offerings. You are just minutes from Old Town, Little Italy, downtown, Harbor Island, Shelter Island, Point Loma, and Seaport
Prime location. Welcome to this newly reimagined, single-level, model-perfect home offering a beautiful combination of charm, comfort, quality finishes, and an exceptional central San Diego lifestyle. Thoughtfully updated throughout, this inviting residence features luxury laminated wood flooring, crown molding, recessed lighting, custom cabinetry, and large windows that fill the home with
High Performing Short Term Rental - $130k in Revenue and ADU. Bring any and all offers to Sellers. Perched atop a scenic hillside in coveted South Mission Hills, 3109 Hawk Street blends modern comfort with timeless San Diego charm. This fully renovated luxury home offers panoramic canyon views from three expansive patios and a rare mix of tranquility, elegance, and income potential—just minutes
New studio, one and two bedroom apartment homes located in historic Mission Hills.Modern living. Built for community. Introducing Rainford, San Diego's premier upscale apartment community, nestled in the charming and historic Mission Hills neighborhood. Rainford beautifully captures a timeless turn of the century aesthetic, blending influences from both the Art Nouveau and Craftsman
Large, bright studio casita on a quiet street Mission Hills/Middletown, close to downtown. No shared walls.Open bedroom/living area with ability to create space for a king bedroom, living area, and workspace as desired. 1 bath (shower only), in-unit private washer/dryer, closet space, kitchen with fridge, dishwasher, electric cooktop, microwave and small convection oven. Good storage
This is a lovely property on a very quiet street two blocks directly behind El Indio Restaurant. Close to Interstate 5, trolley and airport. Three units and a friendly cooperative atmosphere is a priority.
Luxury apartment for rent in South Mission Hills with an incredible view of the bay and airport. Enjoy the 12x24 deck gazing at the bay and watching the airplanes and Cruise Ships all year round, or enjoy the front courtyard while drinking your coffee, socializing with the friendly neighbors walking their dogs. Completely renovated open concept, spacious dining and living area with a
Step into a charming and spacious lower-level residence that perfectly combines comfort, style, and everyday convenience. This UNFURNISHED home features a bright and inviting layout with generous living space, giving you the flexibility to design and personalize it to suit your lifestyle. The living area is filled with natural light, creating a warm and welcoming atmosphere ideal for relaxing or
This ADU was been built in 2024 with love and had taken over a year to perfect! The downstairs is Open Concept with high ceilings, recessed lighting and A/C. The main level has space for a queen bed and has a large 8' closet. Full kitchen with gorgeous quartz countertops and custom cabinets. The bathroom has a beautiful-tiled shower with glass doors, lovely vanity & toilet. It has a Whirlpool
Experience spectacular panoramic views from this spacious 2-bedroom, 2-bath condominium at 2920 Union Street in the highly desirable Mission Hills/Middletown neighborhood. Offering approximately 1,417 square feet, this exceptional home captures breathtaking vistas of Downtown San Diego, San Diego Bay, Coronado Island, Point Loma, the cruise ship terminal, sparkling city lights, and unforgettable
Andy GilcrestThe Equity Company
$4,300 per month
Beautifully Renovated 2Bdm 2.5Ba Mission Hills Condo with Bay Views!
Beautifully Renovated 2Bdm 2.5Ba Mission Hills Condo with Bay Views! This thoughtfully designed condo offers an open-concept floor plan ideal for both everyday living and entertaining. The updated kitchen is appointed with quartz countertops, custom European-style cabinetry, a designer tile backsplash, and recessed lighting. Stainless steel appliances include refrigerator a range/oven,
Brand new high end remodel. This large 850 sq ft 1 bed 1 bath condo is in the quiet neighborhood of Middletown just a few blocks from Little Italy. It has brand new cabinets and quartzite countertops, vinyl plank flooring, in unit laundry, new stainless steel appliances, soundproof windows, central ac and heat, walk in closet, new lighting and fixtures, and a 240 sq ft patio.
Gilbert MouritzenZenden Property Management Inc
$4,195 per month
Gorgeous home in a hidden valley with extra room for office or guest bedroom
Welcome to this charming 2 bedroom, 2 bathroom home located in the heart of San Diego, CA. This cozy house features a fully fenced yard, perfect for enjoying the sunny California weather. The extra room can be used as an office or potentially a third bedroom, providing flexibility for your living needs. The central location offers convenience to all that the city has to offer, while still
This recently remodeled Spacious 2 bed 2 bath 1074 sq ft condominium is located in Middletown just four blocks from Little Italy. Located near San Diego Bay, Little Italy, and Downtown, as well as convenient freeway access. The unit was remodeled with no expense spared with new cabinetry, quartzite countertops, Full size stacked in unit laundry, central AC and heat, vinyl plank flooring and sound
Gilbert MouritzenZenden Property Management Inc
$5,895 per month
"Charming 3-Bed, 2-Bath Oasis in Mission Hills – Spacious 1792 Sq Ft Home on Hawk Street!"
Situated on a quiet, tree-lined street in the heart of historic Mission Hills, this beautifully preserved Craftsman home offers an unrivaled blend of timeless character and modern walk ability. Step outside your door and enjoy effortless access to the vibrant heart of the neighborhood—including organic grocery stores, charming boutiques, acclaimed restaurants, and inviting coffee shops—all just a
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