$1,431,544Average Value$807Average Price per Sq Ft16Homes 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 31 days on the market compared to the national average of 55 days. The median sale price for homes in Middletown, San Diego over the last 12 months is $1,117,500, down 11% from the median home sale price over the previous 12 months.
This charming Craftsman duplex offers unique flexibility for both owner-occupants and investors alike. The front 2/1 home retains much of its original character with hardwood floors, coved ceilings and crown molding throughout, while a beautifully updated kitchen with stainless steel appliances brings a modern touch. At the rear of the property, a fully remodeled attached studio features
Tucked away on a quaint cul-de-sac in South Mission Hills, this beautifully updated Craftsman blends timeless character with fresh, modern touches. Beautiful LVP floors, detailed woodwork, wainscoting, custom built-ins, and tall crisp white baseboards add warmth and character throughout. The light paint palette gives the home a fresh, inviting feel while allowing its classic Craftsman details to
Welcome to 3217 Columbia Street! Perched above the city in the desirable Middletown neighborhood, this spacious residence at offers sweeping views of Downtown San Diego, San Diego Bay, Point Loma, and the surrounding cityscape. Expansive windows fill the open living and dining areas with natural light while showcasing the impressive panorama from multiple rooms. Step onto the private balcony to
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
1st time on market in over 40 years... elevated site sits above the curb. Long driveway and detached garage. 5000 sq. ft. lot. This South Mission Hills location conveniently located to Little Italy, the village of Mission Hills, freeways, beaches and the airport. In 1949 a Bungalow was all the rage in the post war era. Known for smaller, typically 1 story homes on larger lots to enhance the
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
Bring your vision and transform this property into a beautiful home! This spacious 2-bedroom, 2-bath condo in the desirable Mission Hills neighborhood. This corner, end unit offers added privacy, abundant natural light, and a spacious balcony—perfect for relaxing or entertaining. The functional floor plan features generously sized living spaces and includes all appliances, even a washer and dryer
Russell ElrodBerkshire Hathaway HomeServices California Properties
A Rare Mission Hills Opportunity! Why rent when you can own? Tucked along a quiet, tree-lined street in the heart of Mission Hills, this fully renovated 2-bedroom, 2-bath home is a turnkey entry point into San Diego homeownership, with updated plumbing, electrical, and systems throughout. Previously operated as a short-term rental, this property offers an opportunity for short-term and mid-term
*NEW PRICE @ $1,599,900!* Strong interest and multiple offers were received. Previous opportunities did not move forward for reasons unrelated to the property. Now repositioned at an exceptional value in South Mission Hills. Rare Craftsman triplex with three separate residences: a studio featuring floor-to-ceiling windows with unobstructed canyon views toward Bankers Hill and downtown; a spacious
Discover the pinnacle of modern urban living in the highly sought-after Terracina community, perfectly perched on a serene public cul-de-sac ridge where Middletown and South Mission Hills converge. This stunningly designed townhome radiates with natural light, showcasing an expansive open floor plan framed by soaring 9-foot+ ceilings. The seamless flow from the sunlit kitchen directly into the
Brand-New FULLY Permitted 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
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
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,
LARGE STUDIO W/ SEPARATE SLEEPING AREA.... INCLUDES ALL UTILITIES ($200 VALUE)Lovely studio in quaint 4-plex CLOSE TO ALL.Separate sleeping area.Eat-in kitchen.Walk-in closet.Patio deck off kitchen...BBQ ok.Off street parking.Free on-site laundry.Walk to International Restaurant Row.Rent is based on single occupancy. Applicant must have good credit
Newly remodeled rental perched on an expansive 5,353 sq. ft. lot, offering breathtaking panoramic views of the San Diego skyline, bay, and surrounding hills. Enjoy stunning sunsets and refreshing coastal breezes from your own private retreat. The spacious lot provides ample room for outdoor entertaining, gardening, or simply relaxing while taking in the incredible views. Ideally located in one of
This Property can be shown by appointment. We are seeking a twelve month lease. We require a credit report on any occupant over the age of 18. Our application fee is only $35. No pets allowed.
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.
$500 off 1st month!!!2x2 HOUSE with detached parking and washer/dryer in Mission HillsCozy, front house in small community (1 apartment and 1 duplex in the back). This unit has views of San Diego Bay. Beautiful large rooms through out, beautiful hardwood flooring. You have 1 detached garage, street parking for the 2nd vehicle. Located close to all that Mission Hills, Little Italy
$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
2nd floor studio condo located in Mission Hills. Tons of natural light, ample kitchen cabinets and counter space, spacious living area with a private street facing balcony and large shade trees complete this studio home. Community offers on-site laundry and gated parking lot with one assigned space. Close proximity to Little Italy, Balboa Park and major highways.Rental
Discover this bright 2-bedroom, 1-bath apartment in San Diego featuring in-unit full-size laundry and hardwood flooring throughout. The kitchen has stainless steel appliances and a large balcony that overlooks a peaceful canyon view—ideal for morning coffee or evening relaxation. To view this unit, please give us a call at .Requirements: Credit above 640, gross income 2.5x the
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
Updated 2BD/2.5BA Middletown Townhome with Garage, Central A/C & In-Unit Laundry! Welcome home to this updated 2-bedroom, 2.5-bath townhome in Middletown! This spacious multi-level home features a bright, open layout with beautiful flooring, an updated kitchen with quartz countertops and stainless steel appliances, and plenty of natural light throughout. Both bedrooms offer their own bathrooms,
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