$1,409,861Average Value$776Average Price per Sq Ft7Homes 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 43 days on the market compared to the national average of 58 days. The median sale price for homes in Middletown, San Diego over the last 12 months is $1,175,900, down 6% from the median home sale price over the previous 12 months.
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 Spyglass Hill in highly sought-after South Mission Hills. Situated on a premium sun-filled corner lot, this exceptional townhome offers panoramic views of San Diego Bay, the downtown skyline, and the Pacific Ocean. Featuring 3 bedrooms, 3 full bathrooms, and an attached 2-car garage, the home is filled with natural light from soaring 12-foot ceilings, skylights, and expansive windows.
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
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
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
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,
Turnkey Mission Hills condo just a 5-minute walk to Little Italy and moments from Bankers Hill, Balboa Park, museums, dining, and entertainment. Nestled in a peaceful canyon setting, this move-in-ready 1-bedroom, 1-bath home offers the perfect blend of urban convenience and natural beauty. Features include stainless steel appliances, covered assigned parking, no neighbors below, and access to a
Seen it before? Look again. This is a rare sub-$500K foot-in-the-door to one of San Diego's most walkable, sought-after central pockets, ideally situated between Bankers Hill, Hillcrest, Little Italy, and Mission Hills. It's the kind of address people pay a premium to reach. Here's your chance to get in. Live the city the way it's meant to be lived: morning coffee around the corner, Saturday at
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
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
Limited Time Only! $300 off when you apply same day!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
Newly renovated, bright 2 bed/2 bath full floor apartment in Mission Hills / Middletown. Located on a quiet residential street, situated between Little Italy and Mission Hills, expansive views of downtown and harbor from your windows and private deck.The apartment was just renovated with a brand new kitchen, 2 new bathrooms (primary bedroom has ensuite with double vanity and walk-in
Gorgeous Mission Hills 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 sunset bbqs. Walk to
This beautifully updated home which features drought-tolerant landscaping, panoramic views, and an open floorplan, is nestled in a cozy pocket of Mission Hills! The modern craftsman home features a modern kitchen with wood cabinetry, a large center island with bar seating and stainless steel Viking appliances, a large pantry and access to a beautiful viewing deck. The open floorplan flows from
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
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
$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
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
Fully furnished midterm rental available for flexible stays of 30 days or longer.Stylish contemporary 2 bedroom 2 bathroom townhome in South Mission Hills with no neighbors above or below The location is secluded, a short walk to Mission Hills and Hillcrest and minutes to freeways and downtown. This home has been thoughtfully renovated with high quality finishes and a great sense of design. The
$5,690 per month
Luxury Mission Hills Living | Designer Remodel + Prime Central Location | Minutes to Freeways
* 3 Bed | 2 Bath | Approx. 1,506 Sq Ft* Beautifully remodeled single-story detached home in highly desirable Mission Hills* Prime central location near Mission Hills, Little Italy & Downtown* High ceilings, abundant natural light & modern custom finishes* Luxury Vinyl Plank (LVP) flooring throughout – No carpet* Spacious kitchen with breakfast bar & stainless steel
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