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For sale
$2,550,000
5beds
2,730sqft

4314 Middlesex Dr, San Diego, CA 92116

5beds
2,730sqft
Single family residence
Built in 1938
8,982 sqft
2 Garage spaces
$934 price/sqft

What's special

Elegant poolNew roofMediterranean-inspired courtyardLarge windows throughoutTwo bifold windowsBreathtaking canyon viewsWarm and inviting entry

Set on one of the most prominent and sought-after streets in all of Kensington, this stunning Colonial Revival residence offers timeless architecture, sweeping canyon views, and an incredible sense of privacy. A Mediterranean-inspired courtyard welcomes you at the front of the home, creating a warm and inviting entry — the perfect ...

24 days
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2,234
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78
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Source: SDMLS,MLS#: 260005611MLS LogoOriginating MLS: San Diego Association of REALTOR
Travel times

Living Room

Kitchen

Primary Bedroom

Zillow last checked: 7 hours ago

Listing updated: April 02, 2026 at 04:10pm

Listed by:

Patrick H Mercer DRE #01964971 619-846-2083,

Keller Williams La Jolla

Source: SDMLS,MLS#: 260005611MLS LogoOriginating MLS: San Diego Association of REALTOR

Facts & features

Interior

Bedrooms & bathrooms
  • Bedrooms: 5
  • Bathrooms: 3
  • Full bathrooms: 3
Heating
  • Forced Air Unit
Cooling
  • Central Forced Air
Appliances
  • Included: Dishwasher, Disposal, Garage Door Opener, Microwave, Pool/Spa/Equipment, Range/Oven, Refrigerator, Solar Panels, Washer, Free Standing Range, Gas Oven, Gas Stove, Gas Range, Gas Cooking
  • Laundry: Electric, Gas
Features
  • Number of fireplaces: 1
  • Fireplace features: FP in Living Room
Interior area
  • Total structure area: 2,730
  • Total interior livable area: 2,730 sqft
Video & virtual tour

Property

Parking
  • Total spaces: 4
  • Parking features: Attached
  • Garage spaces: 2
Features
  • Levels: 2 Story
  • Pool features: Below Ground
  • Fencing: Full
  • Has view: Yes
  • View description: Evening Lights, Mountains/Hills, Valley/Canyon
Lot
  • Size: 8,982 Square Feet
Details
  • Parcel number: 4650410800

Construction

Type & style
  • Home type: SingleFamily
  • Property subtype: Single Family Residence
Materials
  • Stucco
  • Roof: Composition
Condition
  • Year built: 1938

Utilities & green energy

  • Sewer: Sewer Connected
  • Water: Meter on Property

Community & HOA

Community
  • Subdivision: KENSINGTON
Location
  • Region: San Diego

Financial & listing details

  • Price per square foot: $934/sqft
  • Tax assessed value: $813,040
  • Annual tax amount: $10,854
  • Date on market: 3/10/2026
  • Listing terms: Cash,Conventional,VA

Price history

DateEventPrice
3/11/2026Listed for sale$2,550,000+382%$934/sqft
Source: SDMLS #260005611 Report a problem
8/5/2019Listing removed$4,995$2/sqft
Source: Mercer Properties Report a problem
7/23/2019Price change$4,995-9.1%$2/sqft
Source: Mercer Properties Report a problem
6/28/2019Listed for rent$5,495$2/sqft
Source: Mercer Properties Report a problem
7/14/1999Sold$529,000$194/sqft
Source: Public Record Report a problem

Public tax history

YearProperty taxesTax assessment
2025$10,854 +9.2%$813,040 +2%
2024$9,943 +2.3%$797,099 +2%
2023$9,721 +2.8%$781,471 +2%
2022$9,458 +0.7%$766,149 +2%
2021$9,387 +1.2%$751,127 +1%
2020$9,273 +3.3%$743,426 +2%
2019$8,979 +5.4%$728,850 +2%
2018$8,518 +2.4%$714,560 +2%
2017$8,316 +1.6%$700,550 +2%
2016$8,183 +1.5%$686,815 +1.5%
2015$8,061 +2.6%$676,500 +2%
2014$7,853 $663,249 +0.5%
2013-- $660,253 +2%
2012-- $647,308 +2%
2011-- $634,617 +0.8%
2010-- $629,875 -0.2%
2009-- $631,372 +2%
2008-- $618,993 +2%
2007-- $606,857 +2%
2006-- $594,958 +2%
2005-- $583,293 +2%
2004-- $571,857 +1.9%
2003-- $561,377 +2%
2002-- $550,371 +2%
2001-- $539,580

Find assessor info on the county website

Monthly payment

Est. payment
$15,277/mo
Principal & interest
$12791
Property taxes
$2486
More affordability tools

    Estimated market value

    $2,490,200

    $2.37M - $2.61M

    $7,461/mo

    Climate risks

    Explore flood, wildfire, and other predictive climate risk information for this property on First Street®️.

    Neighborhood: Kensington

    Nearby schools

    GreatSchools rating