$1,408,481Average Value$774Average Price per Sq Ft6Homes 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 44 days on the market compared to the national average of 57 days. The median sale price for homes in Middletown, San Diego over the last 12 months is $1,250,000, consistent with the median home sale price over the previous 12 months.
This striking three-level loft, where modern design meets sweeping views of the San Diego Bay and Downtown skyline. From the moment you step inside, soaring ceilings and architectural details set the tone for a home that feels both sophisticated and effortlessly livable. Custom floating stairs lead you through thoughtfully designed spaces, beginning with a versatile first-floor family room or
This stylish 2-bedroom, 2-bath condominium is located in the highly sought-after Mission Hills community and offers spectacular panoramic views of the bay, ocean, and city from a desirable corner unit. The open concept layout features a large kitchen with slab countertops, stainless steel appliances, wood floors, crown molding, custom baseboards, plush carpeting, recessed lighting, a cozy
Kevin HallBerkshire Hathaway HomeServices California Properties
MISSION HILLS DEVELOPEMNT OPPROTUNITY. 4858 SQFT LOT. LEVEL W/GENTLE SLOPE AT BACK. CLOSE TO DOWNTOWN, AIRPORT, BALBOA PARK, ZOO, LITLE ITALY AND MUCH MORE. POPULAR LOCATION UPPER REYNARD WAY JUST SOUTH OF GOLDFINCH & TORRANCE. SAN DIEGO COMPLETE COMMUNITES MAP TEIR 2 / 8.0 FAR.
1654 LINWOOD STREET AND 1648 WINDER STREET PRESENT AN OUTSTANDING OPPORTUNITY TO ACQUIRE TWO DETACHED HOMES ON ONE PARCEL. THE MAIN HOUSE IS 1,210 SQUARE FEET, AND THE OTHER HOME IS ABOUT 1,000 SQUARE FEET. FRONT HOME HAS NICE VIEWS OF THE HARBOUR/BAY. THE ZONING ACCORDING TO THE CITY OF SAN DIEGO WEBSITE, IS MR 2-5. THE FLOOR-TO-AREA- RATIO IS 8.0. THIS INDICATES THAT A BUILDING OF 45.936 SQUARE
Gregory ScafidiBerkshire Hathaway HomeServices California Properties
Tremendous value for a rarely available 2-bedroom, single-level top-floor unit in a prime spot between Bankers Hill, Little Italy, and Mission Hills. You’re right in the middle of it all with easy access to everything San Diego has to offer. The layout is open and functional, with a spacious primary bedroom, in-unit stackable washer/dryer, and a large private balcony. The kitchen has been updated
Mixed use investment and redevelopment opportunity in the Bankers Hill / Mission Hills corridor. The property consists of two legal parcels totaling approximately 14,246 square feet with 6,222 square feet of existing improvements, currently occupied by a diverse mix of creative, studio, wellness, and service oriented tenants. Provides in place income with the ability to reposition rents while
Ideally situated in the heart of Mission Hills, San Diego, this beautiful, updated corner unit offers comfort, privacy, and walkability. Just minutes from Downtown San Diego, Little Italy, and Hillcrest, and surrounded by top-rated restaurants, trendy cafés, and boutique shopping, this prime location delivers the best of San Diego lifestyle with convenient freeway access. This residence features
Michelle PlastirasPacific Sotheby's International Realty
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
Opportunity to acquire a well-maintained, 3-story, six-unit apartment property on Columbia Street, ideally situated between Mission Hills, Little Italy, and Bankers Hill. The property consists of two buildings. The front building at 2801–2807 Columbia Street features four spacious two-bedroom, one-bath units, three garages, and a shared laundry facility. The rear building at 962–964 W. Olive
Steve CairncrossBerkshire Hathaway HomeServices California Properties
SELLER TO ENTERTAIN ALL OFFERS !!! 2831–2837 Columbia Street offers investors a rare opportunity to acquire a four-unit apartment building in one of San Diego’s most sought-after urban neighborhoods. Perfectly positioned between Mission Hills, Bankers Hill, and Little Italy, the property delivers the ideal balance of strong in-place income, long-term appreciation, and unbeatable tenant appeal.
Discover a compelling value-add investment opportunity -- 11-unit residential Investment. Property perfectly positioned in the heart of Middletown, one of Metro San Diego's most sought-after and consistently resilient neighborhoods. This is your chance to acquire a property in a sub-market that continues to attract strong renter demand and long-term appreciation potential. RM-2-5 zoned corner lot
Breathtaking Views, Prime Location & Entertainer’s Dream! Perched on the canyon's edge in a quiet cul-de-sac, this home offers 2,702 sqft of thoughtfully designed living space with panoramic ocean, city, bay, and evening light views. Step inside to soaring ceilings and an open, airy layout that welcomes natural light throughout. The heart of the home is a chef’s delight—featuring a 5-burner gas
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
Your New Home AwaitsWelcome home to Overlook Point Apartments in San Diego’s beautiful Mission Hills neighborhood. We are located just off Interstates 5 and 8, providing easy freeway access and a very central, convenient location. Excellent dining, shopping, and entertainment destinations are minutes away, with the San Diego Trolley nearby. Discover everything that makes San Diego,
$2,142 per month
University Crest Apartments | Hillcrest/Mission Hills – Modern Living
Limited-Time Special: 1 Month FREE! + $500 Look & Lease, if you apply same day as tour!Open House: Saturday 10:00am - 11:00am - Call to be added.Welcome to University Crest Apartments, a fully renovated boutique community offering modern living in one of San Diego’s most desirable locations—just minutes from Hillcrest, Mission Hills, and Downtown.Walkable to dining, coffee shops
Welcome to The Patterson House, this gorgeous, rare, historically accredited, fully restored and remodeled 1915 Mission Hills gem from the Arts and Crafts movement, sits quietly in one of the finest communities in San Diego. With a family friendly neighborhood, this 4 bedroom with Loft (optional bedroom) Craftsman house is in pristine turn key condition. Original stunning deep hardwood floors,
Gorgeous Mission Hills fully furnished townhome w/ bay & downtown views. 2 bedroom 2.5 bath with large bonus loft for third bedroom or office. Bright natural light throughout, extra storage space, designer finishes, fireplace, 2 car attached garage, in unit washer/dryer, central AC, dual master bedrooms, chef's kitchen w/stainless steel appliances & quartz countertops, & balcony perfect for
Completely remodeled 2 bedroom/1 bath condo. The unit has quartz counter tops, new appliances, soaker tub, recessed lighting, and ceiling fans. Patio with small green space and 2 sliders. 1 covered parking space with extra storage cabinets.
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
South Mission Hills, quiet, newly renovated, second floor, private balcony, tenant pays utilities(gas, electricity, Wi-Fi/cable) one year lease, no smoking, 1 pet under 25 pounds welcome upon approval. First months rent and security deposit due at signing.
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.
Do Not Disturb Occupants.Welcome to 3266 Goldfinch Street, a beautifully situated 3-bedroom, 2-bathroom home in the heart of Mission Hills—one of San Diego’s most charming and desirable neighborhoods. This residence blends classic character with everyday comfort, offering a warm and inviting space that truly feels like home.Inside, you’ll find a thoughtfully laid-out floor plan
Breathtaking Views, Prime Location & Entertainer’s Dream! Perched on the canyon's edge in a quiet cul-de-sac, this homeoffers 2,702 sqft of thoughtfully designed living space with panoramic ocean, city, bay, and evening light views. Step insideto soaring ceilings and an open, airy layout that welcomes natural light throughout. The heart of the home is a chef’sdelight—featuring a 5-burner gas
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