See Home Value
$3,775,000
● House - Off Market

4223 Middlesex Dr

San Diego, CA 92116
bedrooms
5 Beds
bathrooms
3 Baths, 1 Half Bath
square feet
3,650 Ft²
$19,101
Est. Monthly

About This Property

Artful, lavish and precious rarity all synthesized to create this flawless masterpiece. Introducing a one-of-a-kind executive residence beaming bespoke craftsmanship and innovative sophistication. This new construction architecture pays homage to Kensington's legacy with a brilliant Spanish design. The main house is a work of art, but not at the expense of function and livability. Every facet of daily life has been accommodated, all the while meticulously aligning with modern day contemporary precision. The fixtures, materials and details have created transcendent value. Add to that the perfectly appointed guest home, which is spacious and nothing short of pure inspiration. It doesn't stop there, because the verandas, gardens and ensuing privacy are the ultimate calling card for the discerning connoisseur looking for that quiet luxury experience. *See Supplement for Details*  The main residence boasts approximately 3000sf of timeless refinement. Extensive thought has been given to even the smallest design curve, flooring selection, wall finish, lighting and optimal window placement. Predominantly new construction, there are only a few areas of original front and side wall/roof framing remaining. The infrastructure boasts completely new plumbing, electrical and sewer to the street. The house features MARVIN Windows, FLEETWOOD Sliders, LUTRON Lighting, MIRAGE engineered Hardwood Floors, FITTES integrated air vents, the list goes on and on and on... Let's make a visit into the kitchens of dreams. I mean, are you ready to take a culinary journey into elevated gastronomy? Well, here is the ultimate launching ground for such a trip since you have both MAIN and PREP Kitchens. This kitchen truly sets the standard for timeless functional intelligence, as well as a sleek presentation. All expectations are achieved, be it the SUBZERO refrigeration, WOLF 60" range with double oven and French cooktop, two MIELE dishwashers or exquisite QUARTZITE natural stone countertops. The 11ft+ Island feels dramatic and defining. The auxiliary PREP Kitchen offers a wine fridge, freezer drawers, its own dishwasher and speed oven with microwave, a party ready SCOTSMAN pellet ice maker, coffee station and an Instagram Selfie worthy bar! In a home full of highlights, the centerpiece of the home is arguably the dramatic staircase! Framed by spectacular windows, custom designed iron railing, limestone tile risers with MIRAGE treads, it is topped off with a "MOMA" quality RH Chandelier perched royally over an open two- story light drenched atrium. The main living areas are all transitional open concept rooms with sight lines directly from the front of the home, straight through the custom EUROLINE steel and glass doors and windows, out to the gardens. There is no facet of day to day living that hasn't been considered. The design has integrated bedrooms on both floors, stunning baths, a dog bath, mud room, full laundry room (including ROOMBA Vacuum), an office and/or nursery, and to top it all off is the primary suite you've been searching your whole life for. The suite starts with a beautiful wardrobe featuring a CALIFORNIA CLOSET custom walk-in closet system. The bedroom itself is grand in stature and enjoys rooftop views leading out to the balcony. The lighting, blackout drapes and cabinetry will exceed your expectations. But that's not all - step into the sleek primary bath. Once again, Quartzite natural stone, Kallista shower fixtures, a sumptuous freestanding BLU Bathworks bathtub and a refined potpourri of flooring, lighting and wall tiles take the stage. The guest house is also new construction boasting a separate address and power meter. The kitchen and island are better than most regular home kitchens. The forms, fixtures and materials are all consistent with the main house quality. Between the main house and guest house are the gardens. Manicured and cultured, there is room for a pool, spa or other recreational addition. Multiple electrical accommo...
Unit Size
3,650 Ft²
Days on Market
138 days
Land Size
0.18 acres
Price per sqft
$1,066
Property Type
House
Property Taxes
-
HOA Dues
-
Year Built
1928

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Last updated: 12 months ago (SDMLS #250031699SD)

Price History

Date / Event Date Event Price
Nov 12, 2025 Sold
Sold
Oct 14, 2025 In contract -
In contract
Sep 26, 2025 Price Decreased $3,890,000
↓ $605K (13.5%)
Price Decreased
Jun 25, 2025 Listed by eXp Realty of California, Inc $4,495,000
Listed by eXp Realty of California, Inc

Property Highlights

Garage
Air Conditioning
Fireplace

Building Info

Overview

    General

  • Year Built: 1928
  • Effective Year Built: 1928
  • Building Count: 1
  • Total Rooms: 6
  • Bedroom Count: 3
  • Bathroom Count: 1
  • Full Bathrooms: 1
  • Partial Bathrooms: 1
  • Building Condition: 3
  • Building Quality: 4
  • Construction Type: 6
  • Building Style: 14
  • Exterior Walls Type: 12
  • Interior Walls Type: 0
  • Roof Shape Type: 0
  • Roof Cover Type: 4
  • Floor Count: 100
  • Living Units: 1
  • Floor Cover: 0
  • Basement Type: 0
  • Basement Area: 0
  • Garage Type: 3
  • Parking Space Count: 1
  • Patio Type: 0
  • Porch Type: 0
  • Pool Type: 0
  • Location Influence Type: 000

    Dimensions

  • Lot Size Square Feet: 7,738
  • Lot Size Frontage Feet: 500
  • Total Building Area: 1,384
  • Building Area: 1,384
  • Building Area Measurement: L

    Heating and Cooling

  • Fireplace Count: 1
  • Air Conditioning: 0
  • Heating: 4
  • Heated Square Feet: 1,384
  • Heating Fuel Type: 0

    Utilities

  • Sewer System: 1
  • Water Service: 2

Building

  • Building Type: 0
  • Property Class: R
  • Subdivision: KENSINGTON HEIGHTS EXT
  • Land Acres: 0000000178
  • Standard Land Use Code: 1001
  • County Land Use Code: 11
  • Legal Description 1: LOT 189 TR 001912

Neighborhood

  • School District Name: San Diego City Unified School District
  • School Tax School District: SAN DIEGO CITY
  • Census Tract: 002001

Zoning

  • Zoning: RS-1-7

Geography

  • Assessors Map Reference: 001912
  • Subdivision Tract Number: 001912
  • Parcel: 465-031-05-00
  • Lot: 189
  • Municipality: CITY OF SAN DIEGO
  • Latitude: 32.7713
  • Longitude: -117.104

    Address

  • Full Address: 4223 Middlesex Dr
  • Address - House Number: 4223
  • Address - Street Name: Middlesex
  • Address - Suffix Type: Dr
  • State: CA
  • City Name: San Diego
  • Carrier Code: C019
  • 4-Digit Zip Code: 2138
  • Zip Code: 92116

Valuation

    Tax

  • Tax Year: 2023
  • Tax Amount: $1,724,298
  • Tax Rate Code Area: 08-001

    Appraisal Valuation

  • Standard Deviation: 0.1659
  • Valuation Date: Jan 27, 2024
  • Confidence Score: 79
  • Final Value: 1,540,335
  • High Value: 1,795,959
  • Low Value: 1,284,711

    Assessments Valuation

  • Assessed Year: 2023
  • Assessed Total Value: $1,402,500
  • Assessed Land Value: $1,020,000
  • Assessed Improvements Value: $382,500

    Exemptions

  • Homeowner Exemption: Yes

    Sales

  • Current Sale Contract Date: Jun 04, 2021
  • Current Sale Recording Date: Jul 01, 2021
  • Current Sale Price:
  • Current Sale Document Type: 36
  • Current Sale Input Document Number: 2021-0475950
Data used for valuation calculations is provided by RealtyHop, and other third party sources

Comparables

Unit
Status
Type
Beds
Baths
ft²
Price/ft²
Asking Price
Listed On
Closing Price
Sold On
HOA + Taxes

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Frequently Asked Questions

When was property at 4223 Middlesex Drive built and last sold?
The property at 4223 Middlesex Drive was built in 1928 and last sold on Jun 4, 2021 for $1,375,000.
How much is this home worth?
The estimated value of the home located at 4223 Middlesex Drive is $0.
What are some comparable homes to 4223 Middlesex Drive?
There are currently no comparable homes to 4223 Middlesex Drive.