$1,275,000
5445 Chesley AV
Los Angeles, CA, 90043
Privately set behind mature landscaping in Windsor Hills adjacent, 5445 Chesley Ave is a striking architectural retreat designed for those who appreciate style, serenity, and seamless indoor-outdoor living. Three (3) bedrooms and three full baths in the home, plus a garage conversion with room for 4th bedroom and 3/4 bathThoughtfully curated with bold contemporary elements and zen-inspired spaces, this one-of-a-kind residence offers the perfect balance of quiet retreat living and effortless entertaining. As you enter, you are immediately welcomed into an expansive living room highlighted by dramatic oversized picture windows, custom built-ins, rich textured flooring, and a sleek modern fireplace that anchors the space with warmth and sophistication. Sliding glass doors and open sightlines create a natural flow throughout the home, filling the interiors with light while blurring the lines between indoors and out. The open-concept dining area and chef-inspired kitchen offer a vibrant yet functional gathering space, complete with custom cabinetry, stone countertops, stainless steel appliances, designer backsplash, and a large center island ideal for hosting family and friends. Architectural ceiling details, bold color palettes, and custom finishes throughout the home create a truly artistic and elevated atmosphere. The spacious family room opens effortlessly to the private outdoor courtyard and sparkling in-ground lap pool, creating a tranquil resort-like setting perfect for relaxing, entertaining, or enjoying peaceful evenings under the stars. Multiple patio and lounge areas provide flexibility for intimate gatherings or larger celebrations, while the lush privacy hedging enhances the home’s secluded feel. The primary suite serves as its own private sanctuary, featuring generous proportions, a spa-inspired bath, walk-in closet, and calming views of the pool and outdoor spaces. Additional bedrooms are thoughtfully positioned for comfort and privacy. Just steps from the pool, a separate private guest area with its own bathroom offers an ideal setup for guests, creative workspace, wellness studio, or extended stays. Set on a beautifully designed lot with gated parking, a covered carport, and exceptional architectural character throughout, this residence is a rare offering that combines modern design, privacy, and a true lifestyle experience in one of Los Angeles’ most desirable neighborhoods.
Property Details
Price:
$1,275,000
MLS #:
26816735
Status:
Active
Beds:
4
Baths:
4
Type:
Single Family
Subtype:
Single Family Residence
Neighborhood:
phhtparkhillsheights
Listed Date:
May 15, 2026
Finished Sq Ft:
2,209
Total Sq Ft:
2,209
Lot Size:
7,001 sqft / 0.16 acres (approx)
Year Built:
1924
Schools
School District:
Los Angeles Unified
Interior
Appliances
DW, GD, RF, GS, BBQ, BI, CO, RA
Bathrooms
3 Full Bathrooms, 1 Three Quarter Bathroom
Cooling
CA
Flooring
TILE, WOOD, CARP
Heating
CF
Interior Features
CF
Laundry Features
IN, ICL, DINC, WINC
Levels
A
Exterior
Common Walls
NCW
Construction Materials
STC
Direction Faces
E
Exterior Features
RG
Fencing
WD, WI
Roof
CMP, SHN
Security Features
SD, COD, GC
Spa Features
NO
View
NO
Window Features
BLI, SCR
Financial
Get Out There, A Simply Outgoing Approach to Life. James Outland Jr. is one of those rare people who simply has an outgoing approach to life. No matter the activity… from dune buggy riding to skydiving to motorcycling to riding the local Pismo Beach waves… James Outland Jr. approaches life with a “just get out there and do it” kind of attitude. A zest for Life. James’ zest for life is obviously apparent in his many exciting hobbies. In his spare time, he loves riding dune buggies or hi…
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Current real estate data for Single Family in Los Angeles as of May 25, 2026
7,253
Single Family Listed
88
Avg DOM
427
Avg $ / SqFt
$1,675,605
Avg List Price
Community
- Address5445 Chesley AV Los Angeles CA
- CityLos Angeles
- CountyLos Angeles
- Zip Code90043
Similar Listings Nearby
Property Summary
- 5445 Chesley AV Los Angeles CA is a Single Family for sale in Los Angeles, CA, 90043. It is listed for $1,275,000 and features 4 beds, 4 baths, and has approximately 2,209 square feet of living space, and was originally constructed in 1924. The current price per square foot is $577. The average price per square foot for Single Family listings in Los Angeles is $427. The average listing price for Single Family in Los Angeles is $1,675,605. To schedule a showing of MLS#26816735 at 5445 Chesley AV in Los Angeles, CA, contact your James Outland agent at 8057482262.
Courtesy of Pacific Playa Realty. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the California Regional Multiple Listing Service. Detailed information about real estate listings held by brokerage firms other than James Outland include the name of the listing broker. Neither the listing company nor James Outland shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. California Regional Multiple Listing Service. All rights reserved. 5445 Chesley AV
Los Angeles, CA































































