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For salePrice cut: $155K (9/3)
$1,995,000
3beds
2,100sqft

4391 Middlesex Dr, San Diego, CA 92116

3beds
2,100sqft
Single family residence
Built in 1947
1.47 Acres
2 Garage spaces
$950 price/sqft

What's special

Designer finishesEstate-like feelUnmatched canyon backdropEndless canyon vistasQuiet cul-de-sacAbundant natural lightGorgeous center island

Set on a quiet cul-de-sac in the heart of north Kensington, this extraordinary canyon rim home sits on nearly 1.5 acres and offers a truly rare opportunity to own the 3rd largest lot in the entire neighborhood. This tastefully remodeled single level home delivers a level of privacy, tranquility, and natural beauty that is almost impossible to find while still being moments from the restaurants, coffee shops, and boutiques along Adams Avenue. . Mature landscaping and expansive grounds create an estate-like feel while the home embraces sweeping canyon views from nearly every room. Inside, you're welcomed by beautiful original hardwood floors, abundant natural light, and a warm living room anchored by a fireplace and oversized windows framing the breathtaking scenery beyond. Stunning archways guide you from room to room, blending timeless architectural charm with tasteful modern updates. Designed for both everyday living and entertaining, the remodeled kitchen serves as the heart of the home with a gorgeous center island, designer finishes, ample cabinetry, and effortless flow into the main living spaces. The primary suite feels like a private retreat with endless canyon vistas, French doors opening to a spacious view deck, and a beautifully remodeled ensuite. Additional bedrooms are generously sized and filled with natural light. Outside, multiple entertaining areas, sprawling grounds, and the unmatched canyon backdrop create an atmosphere rarely found in Metro San Diego. Opportunities to own a property of this size, setting, and caliber in Kensington are exceptionally rare.

39 days
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1,173
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54
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Source: SDMLS,MLS#: 260018434MLS LogoOriginating MLS: SDMLS
Travel times

Living Room

Kitchen

Primary Bedroom

Zillow last checked:

Listing updated:

Listed by:

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

Keller Williams La Jolla

Source: SDMLS,MLS#: 260018434MLS LogoOriginating MLS: SDMLS

Facts & features

Interior

Bedrooms & bathrooms
  • Bedrooms: 3
  • Bathrooms: 3
  • Full bathrooms: 3
Heating
  • Forced Air Unit
Cooling
  • Central Forced Air
Appliances
  • Included: Dishwasher, Disposal, Dryer, Garage Door Opener, Refrigerator, Washer, Freezer, Gas Stove, Gas Range, Counter Top
  • Laundry: Electric, Gas
Features
  • Number of fireplaces: 1
  • Fireplace features: FP in Living Room
Interior area
  • Total structure area: 2,100
  • Total interior livable area: 2,100 sqft
Video & virtual tour

Property

Parking
  • Total spaces: 4
  • Parking features: Detached
  • Garage spaces: 2
Features
  • Levels: 1 Story
  • Pool features: N/K
  • Fencing: Partial
  • Has view: Yes
  • View description: City, Mountains/Hills
Lot
  • Size: 1.47 Acres
Details
  • Parcel number: 4650201000
  • Zoning: R-1:SINGLE
  • Zoning description: R-1:SINGLE

Construction

Type & style
  • Home type: SingleFamily
  • Property subtype: Single Family Residence
Materials
  • Stucco
  • Roof: Flat
Condition
  • Year built: 1947

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: $950/sqft
  • Tax assessed value: $967,153
  • Date on market: 7/29/2026
  • Listing terms: Cash,Conventional,FHA,VA

Price history

DateEventPrice
9/3/2026Price change$1,995,000-7.2%$950/sqft
Source: SDMLS #260018434 Report a problem
7/29/2026Listed for sale$2,150,000-5.5%$1,024/sqft
Source: SDMLS #260018434 Report a problem
7/29/2026Listing removed$2,275,000$1,083/sqft
Source: SDMLS #260011908 Report a problem
7/25/2026Pending sale$2,275,000$1,083/sqft
Source: SDMLS #260011908 Report a problem
6/15/2026Price change$2,275,000-4.2%$1,083/sqft
Source: SDMLS #260011908 Report a problem
5/15/2026Listed for sale$2,375,000+76.6%$1,131/sqft
Source: SDMLS #260011908 Report a problem
7/19/2018Listing removed$1,345,000$640/sqft
Source: Tristani Real Estate Group #180025145 Report a problem
6/7/2018Price change$1,345,000-2.2%$640/sqft
Source: Tristani Real Estate Group #180025145 Report a problem
5/11/2018Listed for sale$1,375,000+78.6%$655/sqft
Source: Tristani Real Estate Group #180025145 Report a problem
3/27/2013Sold$770,000-18.9%$367/sqft
Source: Public Record Report a problem
2/16/2012Listing removed$949,000-2.7%$452/sqft
Source: Prudential California Realty #110024290 Report a problem
1/22/2011Price change$975,000-1.4%$464/sqft
Source: NRT California #100064420 Report a problem
11/5/2010Listed for sale$989,000+5.2%$471/sqft
Source: NRT California #100064420 Report a problem
2/13/2009Sold$940,000+59.1%$448/sqft
Source: Public Record Report a problem
8/12/2008Sold$591,000-32.8%$281/sqft
Source: Public Record Report a problem
9/23/2005Sold$880,000$419/sqft
Source: Public Record Report a problem

Public tax history

YearProperty taxesTax assessment
2026-- $967,153 +2%
2025$12,555 +8.4%$948,190 +2%
2024$11,580 +2.3%$929,599 +2%
2023$11,322 +2.8%$911,372 +2%
2022$11,017 +1.5%$893,503 +2%
2021$10,850 +1.2%$875,984 +1%
2020$10,717 +3.2%$867,002 +2%
2019$10,386 +5.5%$850,003 +2%
2018$9,841 +2.4%$833,337 +2%
2017$9,606 +1.6%$816,998 +2%
2016$9,452 +1.5%$800,980 +1.5%
2015$9,309 +1.6%$788,949 +2%
2014$9,162 $773,495 -21.3%
2013-- $983,001 +2%
2012-- $963,728 +2%
2011-- $944,833 +0.8%
2010-- $937,772 +58.7%
2009-- $591,000 -35.4%
2008-- $915,552 +2%
2007-- $897,600 +2%
2006-- $880,000 +669.6%
2005-- $114,339 +2%
2004-- $112,098 +1.9%
2003-- $110,044 +2%
2002-- $107,887 +2%
2001-- $105,772

Find assessor info on the county website

Monthly payment

Est. payment
$12,085/mo
Principal & interest
$10140
Property taxes
$1945
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Estimated market value

Not available

Estimated sales range

Not available

Not available

Climate risks

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

Neighborhood: Kensington

Nearby schools

Franklin Elementary School
Grades K-51.1 miles
5/10
GreatSchools® Rating
Test Score Rating
5/10
Student Progress Rating
4/10
Wilson Middle School
Grades 6-81.5 miles
3/10
GreatSchools® Rating
Test Score Rating
3/10
Student Progress Rating
2/10
Hoover High School
Grades 9-121.1 miles
4/10
GreatSchools® Rating
Test Score Rating
5/10
College Readiness Rating
2/10