Middletown Homes for Sale

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

Penny Nathan Ascent Real Estate

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

Bobby Graham Personalized RE

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

Kyle Stamps Roderic Mack Wright, Broker

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 Ortega Pacific Sotheby's International Realty

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

Holly Darrah eXp Realty of California, Inc.

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

Amber Bunch Bunch Realty Group

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

Chad Dannecker Compass

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

Shakira Shahrir Del Fresno Compass

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

Steven Ortiz Dolan Realty Company

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,

Laura Valente The Agency

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. OPEN HOUSE: 12-3 pm Saturday and Sunday, September 12th and 13th, 2026.This delightful property places you at the heart of San Diego’s best offerings. You are just minutes from Old Town,

Jodie Moncrief 888 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

Keegan Wetzel Real Broker

TURNKEY Mission Hills living with approximately 1,100 SF of finished, usable space, plus an approximately 900 SF walk-in basement offering exceptional storage. This beautifully updated 2BR/2BA home features an approximately 900 SF main residence plus an approximately 200 SF detached and finished flex space. The main home blends original character with thoughtful updates. It features beautiful

Jonathan Vizcaino Compass

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.

Josh Browar The Browar Group

Love at first sight begins before you even step inside. Tucked just blocks from the vibrant shops and restaurants of Mission Hills, this Mission Revival-style home greets you with sun-warmed stucco walls, graceful archways, and a wrought-iron elegance that speaks to old Spanish California — outdoor spaces that instantly feel like home, steeped in character you simply can't recreate. Step through

Miguel Aldrete Weichert SoCal

Discover this remarkably maintained two-story duplex, originally built in 1933 and carefully preserved both inside and out. The updated units are currently occupied by excellent, long-term tenants, offering immediate rental income and a smooth transition for the next owner. The exterior is clean, well-kept, and presents beautifully, while the oversized lot provides ample space to garden, relax,

Craig Everett Advent Real Estate

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

James Jam Berkshire Hathaway HomeService

Offered at an exceptional basis of just $275,000 per unit, 3206-16 Reynard Way presents investors with a rare opportunity to acquire a well-located multifamily asset in San Diego's urban core. The property provides attractive day-one income while offering meaningful upside through future rental growth and the long-term potential to redevelop the site. Zoned RM-3-7, the property offers investors

Derek Kaptanoglu Compass

Welcome to this bright and cheerful top-floor, one-bedroom, one-bath condo in the desirable Mission Hills/Middletown area. Move-in ready, this inviting home features stylish tile flooring, warm carpeting, designer cabinetry, and chic appliances. Abundant natural light creates a welcoming atmosphere, while the spacious private patio deck is perfect for relaxing, entertaining, or enjoying San

Craig Gagliardi Berkshire Hathaway HomeServices California Properties

1620-24 Glenwood Dr is situated in one of San Diego's most desirable neighborhoods; this duplex provides the rare opportunity for buyers looking to customize a property to their own vision. The lot offers outdoor space with room to enhance landscaping or create outdoor living spaces. Located just moments from Mission Hills dinning and parks. Downstairs unit is a studio garage conversion.

Sandra Love Willis Allen Real Estate