# 4282 Middlesex Drive, San Diego, CA 92116 > **TL;DR:** 5bd/4ba single family, $2,645,000 ($751/sqft), built 1960, 3,523 sqft. > Fireplace, A/C, 2-car garage. Est. $14,146/mo. Listed 53 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $2,645,000 | | Price/sqft | $751 | | Bedrooms | 5 | | Bathrooms | 3 full, 1 half | | Square Feet | 3,523 | | Year Built | 1960 | | Lot Size | 10,088 sqft (0.23 acres) | | Stories | 2 | | Garage | 2-car | | Property Type | Single Family (Other) | | Status | Active | | Days on Market | 53 | ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $13,375 | | Estimated Insurance | $771 | | **Total** | **$14,146** | ## Key Amenities - Fireplace - A/C - 2-car garage ## Property Highlights - Built in 1960 - 0.23 acre lot - 2 stories - 4 parking spaces - Fireplace ## Description ### Agent Description Classic Kensington! Located on one of Kensington's finest streets, this stately two-story traditional offers five bedrooms and three-and-one-half baths with an abundance of space and timeless appeal. A grand entry welcomes you and leads in two directions: to the left, a formal living room with high ceilings and fireplace; to the right, a spacious formal dining room easily accommodating a generous table for memorable family gatherings. Beyond the dining room is an expansive family room with French doors opening to the rear patio. The adjacent kitchen is exceptionally spacious, featuring stainless steel counters, an abundance of cabinetry, and a charming breakfast nook. Three bedrooms on the lower level, along with a separate laundry room, provide an ideal arrangement for guests, extended family, or additional living space. Upstairs, a library/office area sits at the top of the stairs, along with a smaller bedroom and an extraordinary primary suite that is sure to impress. The spacious bedroom features a dramatic vaulted wood ceiling, while the generously sized walk-in closet and bath provide plenty of room and comfort. Decks off both levels capture wonderful north-facing views and add to the home's quintessential Kensington appeal. And don't miss the detached lower-level room-perfect for a home gym, office, studio, or creative space. A truly special home in a coveted location! ## Location - **Address:** 4282 Middlesex Drive, San Diego, CA 92116 - **County:** San Diego - **Neighborhood:** KENSINGTON - **Coordinates:** 32.772008, -117.102484 - **Google Maps:** https://www.google.com/maps?q=32.772008,-117.102484 ## Virtual Tour & Media - **Video Tour:** https://player.vimeo.com/video/1224675162?h=200eb5525a&badge=0 ## Listing Agent - **Name:** Mike Tristani · **License:** 01406640 - **Brokerage:** Tristani Real Estate Group - **Broker Phone:** (619) 501-4000 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/4282-Middlesex-Dr_San-Diego_CA_92116_M18808-68693?f=listhub&s=SANDICOR&m=260021875&c=propsimple) ## Photos ![4282 Middlesex Drive - Photo 1](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f2491933413r.jpg) ![4282 Middlesex Drive - Photo 2](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f2583132071r.jpg) ![4282 Middlesex Drive - Photo 3](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f418686233r.jpg) ![4282 Middlesex Drive - Photo 4](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f2148370743r.jpg) ![4282 Middlesex Drive - Photo 5](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f744913468r.jpg) ![4282 Middlesex Drive - Photo 6](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f2555977740r.jpg) ![4282 Middlesex Drive - Photo 7](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f241851620r.jpg) ![4282 Middlesex Drive - Photo 8](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f255696809r.jpg) ![4282 Middlesex Drive - Photo 9](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f493192290r.jpg) ![4282 Middlesex Drive - Photo 10](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f1453055503r.jpg) ![4282 Middlesex Drive - Photo 11](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f3561311521r.jpg) ![4282 Middlesex Drive - Photo 12](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f2640612520r.jpg) ![4282 Middlesex Drive - Photo 13](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f2845453509r.jpg) ![4282 Middlesex Drive - Photo 14](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f58146948r.jpg) ![4282 Middlesex Drive - Photo 15](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f1385475649r.jpg) ![4282 Middlesex Drive - Photo 16](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f1685937583r.jpg) ![4282 Middlesex Drive - Photo 17](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f1828556236r.jpg) ![4282 Middlesex Drive - Photo 18](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f2147219612r.jpg) ![4282 Middlesex Drive - Photo 19](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f2657619990r.jpg) ![4282 Middlesex Drive - Photo 20](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f754109211r.jpg) ![4282 Middlesex Drive - Photo 21](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f3252929722r.jpg) ![4282 Middlesex Drive - Photo 22](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f1882996836r.jpg) ![4282 Middlesex Drive - Photo 23](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f2549314912r.jpg) ![4282 Middlesex Drive - Photo 24](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f2415677056r.jpg) ![4282 Middlesex Drive - Photo 25](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f2265727250r.jpg) ![4282 Middlesex Drive - Photo 26](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f1831594005r.jpg) ![4282 Middlesex Drive - Photo 27](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f780245024r.jpg) ![4282 Middlesex Drive - Photo 28](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f3372924646r.jpg) ![4282 Middlesex Drive - Photo 29](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f1964355440r.jpg) ![4282 Middlesex Drive - Photo 30](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f765564253r.jpg) ![4282 Middlesex Drive - Photo 31](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f827465574r.jpg) ![4282 Middlesex Drive - Photo 32](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f240773543r.jpg) ![4282 Middlesex Drive - Photo 33](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f611680962r.jpg) ![4282 Middlesex Drive - Photo 34](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f783555642r.jpg) ![4282 Middlesex Drive - Photo 35](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f2489433759r.jpg) ![4282 Middlesex Drive - Photo 36](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f1631157326r.jpg) ![4282 Middlesex Drive - Photo 37](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f3349680239r.jpg) ![4282 Middlesex Drive - Photo 38](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f2910001805r.jpg) ![4282 Middlesex Drive - Photo 39](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f1729483517r.jpg) ![4282 Middlesex Drive - Photo 40](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f3137680785r.jpg) ![4282 Middlesex Drive - Photo 41](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f726036280r.jpg) ![4282 Middlesex Drive - Photo 42](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f2491933413r.jpg) ![4282 Middlesex Drive - Photo 43](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f2817824062r.jpg) ![4282 Middlesex Drive - Photo 44](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f2893486577r.jpg) ![4282 Middlesex Drive - Photo 45](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f143780479r.jpg) ![4282 Middlesex Drive - Photo 46](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f3638004450r.jpg) ![4282 Middlesex Drive - Photo 47](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f3268287791r.jpg) ![4282 Middlesex Drive - Photo 48](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f3009279981r.jpg) ![4282 Middlesex Drive - Photo 49](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f2216639611r.jpg) ![4282 Middlesex Drive - Photo 50](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f3489582566r.jpg) ![4282 Middlesex Drive - Photo 51](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f123176639r.jpg) ![4282 Middlesex Drive - Photo 52](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f2231170714r.jpg) ![4282 Middlesex Drive - Photo 53](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f401589121r.jpg) ![4282 Middlesex Drive - Photo 54](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f1601772412r.jpg) ![4282 Middlesex Drive - Photo 55](http://lh.rdcpix.com/fa316eb599875d375ec46c068164461el-f141033861r.jpg) --- **MLS#:** 260021875 | **Updated:** 2026-10-22 **Source:** listhub *Copyright © 2026 San Diego MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.* [View on PropertySimple](https://www.propertysimple.ai/listing/4282-middlesex-drive-san-diego-ca-92116-7fbbea99f85f478c9d0d519d6b4b4bbe) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://www.propertysimple.ai/listing/4282-middlesex-drive-san-diego-ca-92116-7fbbea99f85f478c9d0d519d6b4b4bbe#listing", "url": "https://www.propertysimple.ai/listing/4282-middlesex-drive-san-diego-ca-92116-7fbbea99f85f478c9d0d519d6b4b4bbe", "name": "4282 Middlesex Drive, San Diego, CA 92116", "description": "Classic Kensington! Located on one of Kensington's finest streets, this stately two-story traditional offers five bedrooms and three-and-one-half baths with an abundance of space and timeless appeal. 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