14

Middletown Homes for Sale

Section Image
  • /32

    $1,295,000

    • 3 Beds
    • 2.5 Baths
    • 1,858 Sq Ft

    3711 Columbia St, San Diego, CA 92103

    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

    3711 Columbia St, San Diego, CA 92103
  • /74

    $1,275,000

    • 2 Beds
    • 3 Baths
    • 1,949 Sq Ft

    3033 India St Unit 6, San Diego, CA 92103

    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

    Sidnev Muldrow Compass

    3033 India St Unit 6, San Diego, CA 92103
  • /31

    $2,095,000

    • 8 Beds
    • 4 Baths
    • 3,400 Sq Ft

    3062-68 Columbia St, San Diego, CA 92103

    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

    3062-68 Columbia St, San Diego, CA 92103
  • /68

    $4,499,000

    • 4 Beds
    • 4 Baths
    • 4,600 Sq Ft

    3515 Union St, San Diego, CA 92103

    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

    3515 Union St, San Diego, CA 92103
  • /27

    $499,000

    $26K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 726 Sq Ft

    2850 Reynard Way Unit 30, San Diego, CA 92103

    Lowest Priced 2-Bedroom in 92103 - And It's Not Even Close! Sitting between Bankers Hill, Hillcrest, Little Italy, and Mission Hills, you're walking distance from some of San Diego's best restaurants, coffee shops, and nightlife, with Balboa Park and the waterfront just minutes away. This is the kind of location people pay a premium for. Here’s your entry point. The unit is light, bright, and

    sam shuck Golden Empire Realty

    2850 Reynard Way Unit 30, San Diego, CA 92103
  • /67

    $799,000

    $50K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,125 Sq Ft

    909 Sutter St Unit 105, San Diego, CA 92103

    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 Plastiras Pacific Sotheby's International Realty

    909 Sutter St Unit 105, San Diego, CA 92103
  • /75

    $1,749,900

    • 4 Beds
    • 3 Baths
    • 1,994 Sq Ft

    3109 Hawk St, San Diego, CA 92103

    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

    3109 Hawk St, San Diego, CA 92103
  • /44

    $2,575,000

    • 26284 Beds
    • 86 Baths
    • 6,028 Sq Ft

    2801-7 Columbia St, San Diego, CA 92103

    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 Cairncross Berkshire Hathaway HomeServices California Properties

    2801-7 Columbia St, San Diego, CA 92103
  • /18

    $1,995,000

    $200K PRICE DROP
    • 8 Beds
    • 4 Baths
    • 2,860 Sq Ft

    2831-37 Columbia St, San Diego, CA 92103

    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

    2831-37 Columbia St, San Diego, CA 92103
  • /6

    $3,950,000

    $200K PRICE DROP
    • 7,800 Sq Ft

    2901 Columbia St Unit 21, San Diego, CA 92103

    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

    Judy Preston JP Equity Real Estate Corp.

    2901 Columbia St Unit 21, San Diego, CA 92103
  • /2

    $1,395,000

    • 3 Beds
    • 2 Baths

    1716 Glenwood Dr, San Diego, CA 92103

    Steve Malley Steven Michael Malley

    1716 Glenwood Dr, San Diego, CA 92103
  • /2

    $1,995,000

    • 3 Beds
    • 3 Baths
    • 2,330 Sq Ft

    1404 Bush St, San Diego, CA 92103

    Centrally located with backyard privacy and canyon views, this modernized contemporary home offers the perfect blend of location, space, and convenience. The entire second floor is a dedicated primary suite, featuring vaulted ceilings, a generous walk-in closet, en-suite bathroom with jacuzzi tub, and elegant French doors opening to a private rear balcony overlooking canyon views. The main level

    Natasha Mora VIP Premier Realty Corp

    1404 Bush St, San Diego, CA 92103
  • /5

    $1,100,000

    • 2 Beds
    • 2 Baths
    • 1,260 Sq Ft

    1620 Glenwood Dr Unit 2, San Diego, CA 92103

    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.

    Sandra Love Willis Allen Real Estate

    1620 Glenwood Dr Unit 2, San Diego, CA 92103
  • /2

    $1,550,000

    • 4 Beds
    • 4 Baths

    1717 W Walnut Ave, San Diego, CA 92103

    Steve Malley Steven Michael Malley

    1717 W Walnut Ave, San Diego, CA 92103

Why Live in Middletown

Middletown in San Diego is a neighborhood characterized by its steep streets and spacious lots adorned with coastal foliage. The area showcases a variety of architectural styles, with 1920s bungalows, Craftsman homes, and grand Spanish Revivals being the most prominent. Newer additions include 1980s contemporary designs and luxury condos with bay views. Residents enjoy a range of dining options on India Street, such as Gelato Vera Caffe, Blue Water Seafood Grill & Market, and Shakespeare Pub. For fine dining, the Wine Vault & Bistro offers a fixed menu with wine pairings. Nearby, Goldfinch Street features popular eateries like Farmer's Bottega and Harley Gray Kitchen & Bar. Harper's Topiary Garden, a unique display of over 50 hand-trimmed hedges, is a local highlight. Pioneer Park and Mission Hills Park provide recreational spaces with playgrounds, walking trails, and shaded areas, while Balboa Park, home to the San Diego Zoo, is 4 miles east. Ocean Beach is 6 miles west. Middletown is part of the highly rated San Diego Unified School District, with students attending Grant School and Point Loma High. The neighborhood is conveniently located near Interstate 5, offering a 2-mile commute to downtown San Diego and proximity to the San Diego International Airport.

Frequently Asked Questions

Is Middletown a good place to live?
Middletown is a good place to live. Middletown is considered fairly walkable and bikeable with good transit options. Middletown is a neighborhood with a crime score of 4, on par with the average neighborhood in the U.S. Middletown has 6 parks for recreational activities. It is very dense in population with 17.0 people per acre and a median age of 43. The average household income is $127,008 which is above the national average. College graduates make up 58.3% of residents. A majority of residents in Middletown are renters, with 57% of residents renting and 43% of residents owning their home. A local real estate agent serving Middletown can help you decide if this neighborhood is the right one for you. Learn more on our Middletown neighborhood guide.
Is Middletown, CA a safe neighborhood?
Middletown, CA is a safe neighborhood and is on par with the average neighborhood in the United States. It received a crime score of 4 out of 10.
How much do you need to make to afford a house in Middletown?
The median home price in Middletown is $1,285,000. If you put a 20% down payment of $257,000 and had a 30-year fixed mortgage with an interest rate of 6.48%, your estimated principal and interest payment would be $6,480 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $278K a year to afford the median home price in Middletown. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Middletown is $127K.
What are the best public schools in Middletown?
The best public schools that serve Middletown are:
What are the best private schools in Middletown?
The best private schools that serve Middletown are:
What are the most popular zip codes in Middletown, San Diego, CA?
The most popular zip codes in Middletown, San Diego, CA include 92103, 92110, 92101, 92108 and 92109.
What are the most popular neighborhoods near Middletown, San Diego, CA?
The most popular neighborhoods near Middletown, San Diego, CA are Mission Hills, Hillcrest, Bankers Hill, Little Italy and Old Town.

Middletown Home Prices vs. Nearby San Diego, CA Neighborhoods

Middletown Bankers Hill Mira Mesa Old Town
Median Home Price
$1,285,000
$1,199,500
$999,500
$1,087,500
Median Sale Price
$1,250,000
+1% YoY
$1,140,000
-5% YoY
$1,010,000
+5% YoY
$940,000
-35% YoY
Median Single Family Price
$1,789,950
$1,388,000
$1,109,500
$1,962,500
Median Townhouse Price
$2,675,000
$1,740,000
$1,067,630
$1,100,000
Median Condo Price
$925,000
$949,800
$572,500
$735,000
Total Active Listings
7
38
76
3
Market Conditions
2 Months
Seller's Market
5 Months
Balanced Market
2 Months
Seller's Market
4 Months
Balanced Market
How to Buy a Home How to Finance a Home How to Sell a Home