$1,420,364Average Value$818Average Price per Sq Ft4Homes 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 54 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 8% from the median home sale price over the previous 12 months.
Great Opportunity!! Welcome to this cozy, move-in ready single-story home. This home has been fully reimagined, blending timeless charm with modern elegance.Set on a prime corner lot with no HOA, the 3-bedroom, 2.5-bath residence offers nearly 2,000 sq. ft. of living space with an open floor plan designed for today’s lifestyle. The light-filled living areas flow seamlessly, highlighted by
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.
Nestled in the desirable Mission Hills neighborhood, this remodeled single-story 3-bedroom, 2-bath home is positioned on a generous 8,748 SF lot. The turnkey residence offers the flexibility to enjoy as a primary home or short-term rental, while the oversized RM-3-7–zoned lot and Complete Communities designation provide attractive ADU and development incentives for investors and developers.
Stephanie JezekeXp Realty of Southern California, Inc.
Mission Hills, San Diego, a fantastic development opportunity, especially given its location and potential for stunning views. Here are some key points and considerations for potential buyers or developers: Location and Neighborhood: Mission Hills is known for its historic charm, scenic views, and vibrant community. Its proximity to Downtown San Diego and other urban areas makes it a desirable
Discover the perfect blend of character, flexibility, and modern comfort in this beautifully refreshed Mission Hills triplex. Ideal for an owner-occupier, this versatile property offers the opportunity to live in one unit and generate rental income from the others—all in one of San Diego’s most desirable neighborhoods. The property includes a 2-bedroom, 1-bath main home, a 1-bedroom, 1-bath
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
High Performing Short Term Rental - $130k in Revenue and ADU. Perfect year-end bonus depreciation purchase! 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,
Experience Mission Hills at its finest! Tucked into the highly sought-after Middletown neighborhood, this 4-bedroom, 2.5-bath Spanish-Mediterranean home offers a rare combination of sweeping city and canyon views, exceptional privacy, and a true indoor-outdoor lifestyle—set on an expansive 1/3-acre lot just minutes from the heart of San Diego. From the moment you enter, the home feels both warm
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. With immediate access to Downtown San
Introducing 3318–3320 Union Street, a rare and highly coveted two-unit multifamily asset in one of San Diego’s most desirable urban enclaves. Perfectly combining privacy, modern luxury, and investment appeal, this property represents a trophy small asset for discerning investors seeking a stable, high-quality addition to their portfolio. The property features two recently modernized apartments: a
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
Available Now | Luxury Mission Hills Rental Experience elevated California living in this beautifully remodeled, Craftsman-inspired 3-bedroom, 2-bath home ideally located in the heart of San Diego, Mission Hills. Designed for both comfort and entertaining, this home features an open floor plan, soaring 10-foot ceilings, and abundant natural light throughout. The main living spaces showcase
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
Live the San Diego lifestyle in this beautifully updated, modern, ideally located townhome in South Mission Hills! The large living room features an inviting fireplace and French doors that lead out to the private brick patio. The sleek modern kitchen features a spacious island, stainless steel appliances, a bay window, and a dining space with convenient access to the outdoor view balcony.
1 MONTH FREE!!! This remodeled unit is a large 1,050 sq ft 2 bed 2 bath condominium. It is a corner unit less than a 10 minute walk to Little Italy and close access to freeways. The unit features new calcutta quarts counter tops, vinyl plank flooring, new shower and baths, sound proof windows and doors, central air conditioning and heat, one off street parking, and views of down town and San
Property Id: 2091767ULTRA-MODERN 1BR/1BA with separate work den, 1000 SF | SPA BATH •Brand New KITCHEN; Kitchen appliances •$2695 /MO | FULLY REMODELED | GATED | EV CHARGINGGated Duplex/ Only one neighbor inside the gated property.Just minutes from Little Italy, Downtown, and the San Diego waterfront. This fully remodeled luxury 1BR/1BA unit is a private unit in a
1 MONTH FREE!!! Large beautifully remodeled 1 bed 1 bath condo on the North edge of Little Italy and Middletown. This 841 sq ft brand new remodel has an open kitchen with new 15" deep cabinets, quartzite countertops and Stainless Steel Appliances. Beautiful panoramic views of the San Diego Bay, Downtown, all the way to the point. Sound proof windows and doors, vinyl plank flooring, can lighting,
This property at 3523 Crowell St features 2 bedrooms and 1 bathroom within a total of 825 square feet. The living room offers ample space for relaxation. The bathroom includes a tub/shower combination for convenience. Each bedroom provides sufficient room for furnishings and personal items. Amenities include cable readiness, high-speed internet access, and in-unit washer/dryer for added
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