0.jpg
1 / 74

28 Caballeros Road, Rolling Hills, CA 90274

$8.00M5bd · 6ba · 5,874 sqft
Lot 60,709 sqft•HOA $16789/mo•Single Family Residence•
Active
•18d on market•MLS# SB-26206322

Property Description

Welcome to 28 Caballeros Rd — a rare offering in the gated hillside enclave of Rolling Hills, where sprawling parcels, hiking and horse trails, and lush greenery set the stage for true resort-style living above the clouds. This exceptional 5,874 sq ft estate (4,727 sq ft main house plus a ~1,147 sq ft guest house) offers 5 bedrooms and 5.75 baths, fully reimagined by Kim Lapin Interiors and Canyon Homes in a modern Montecito Ranch aesthetic. Enter through a private courtyard with a running fountain into a home defined by vaulted ceilings and thoughtful flow throughout. Curated natural, vintage, and hand-crafted finishes are found at every turn — Calacatta Viola marble, solid white oak and walnut cabinetry with unlacquered brass and polished nickel hardware, zellige and sand-cast brick, warm hardwood floors, and four fireplaces. A formal living room opens directly to the stunning backyard, with views of the Queen's Necklace and twinkling city lights setting the tone for indoor-outdoor living. The North side of the home holds the kitchen, dining, and family living room — a warm, easy space built for lazy days together. The chef's kitchen features double ovens and a sunny breakfast nook, opening naturally into the family room beyond. The South side offers four bedrooms, each with its own ensuite bath for maximum privacy. The primary suite is a true sanctuary, with soaring vaulted ceilings and natural light pouring in, its own fireplace, a walk-in closet, and a spa-like primary bath designed for a quiet retreat. Downstairs, a bonus den awaits with a projector screen, bar area, and direct access outside, along with a laundry room and additional office space. The existing ADU — which includes the 5th bedroom, bath, and kitchenette with sweeping views — was expanded by 500 sq ft. The result is a fully built-out gym with white oak floors, mirrored walls, and minimal-frame Titoni sliding doors opening to views of the horse corral. Outside, enjoy a fenced yard with pool, spa, fire pit, and BBQ area, plus full horse facilities and direct access to the Purple Canyon trail — a true equestrian and entertainer's dream in one of the South Bay's most coveted communities.

Features & Amenities

FeeBuilt 1981

Property Details

Land Type
Fee
Year Built
1981
Property Type
Residential
Property Subtype
Single Family Residence
Parking Spaces
3
Garage Spaces
3
Heating
Central
Cooling
Central Air
View
City Lights, Coastline
Flooring
Wood
Roof
Tile
City
Rolling Hills
Zip Code
90274
County
Los Angeles
Listed byCompass, Robin Brooke Smith

Mortgage Calculator

Current Rates

$
$
%
Monthly Payment
$40,427.07
Principal & Interest
Loan Amount
$6,396,000
Total Interest
$8,157,745
Total Payment Over 30 Years
$14,553,745
This calculator provides estimates only. Actual mortgage payments may include taxes, insurance, HOA fees, and PMI. Contact a lender for accurate quotes.

Comparative Market Analysis

Luxury Tier · 5 active · 3 closed

28 Caballeros Road, Rolling Hills, CA 90274

Rolling Hills · Single Family Residence

$8.00M
Luxury Tier
Beds
5
Baths
6
Sqft
5,874
Lot
1.39 ac
Year
1981
$/Sqft
$1361
Pool: Yes✓
Spa: Yes✓
View: city✓
Garage: 3-car✓

Listed 19.3% above the median closed sale of $6,700,000. Price per sqft ($1,361) is a 32% premium to closed comps ($1,028). Closed comps sold at 92% of list — buyers have negotiating leverage. Expect a longer timeline — comps averaged 196 days on market. Luxury tier — fewer comparable sales widen the confidence range.

Price Position

Positioned above the market — commands a premium.

Premium
Subject listed at $8.00M· $1,361/sqft
Total list price
Closed comps
vs closed median $6.70M
+$1.29M (+19.3%)
Active comps
vs active median $6.90M
+$1.10M (+15.9%)
Price per sqft
Closed compsinsufficient comp data
Active comps
vs active avg $/sqft $1,178
+$183 (+15.5%)

Active Properties (5)

Active Comparables

AddressCityYearBDBTHSqFtLotSzLP/SqFtLPDIMScore
57 SaddlebackRolling Hills1986455,27484,743$1,057$5.58M18870
1384 Via RomeroPalos Verdes Estates1978666,27115,695$956$6.00M4668
1905 Paseo Del SolPalos Verdes Estates1990575,74712,262$1,200$6.90M5267
1565 Via LeonPalos Verdes Estates2024576,16516,986$1,427$8.80M2167
2990 Twin Harbors ViewRancho Palos Verdes2005466,20812,669$1,252$7.77M2565
Total: 5 · Average4.86.25,93328,471$1,178.4$7.01M66.4
Median6,165$6.90M

Closed Properties (3)

Closed Comparables

AddressCityYearDateBDBTHSqFtLotSzLPSPSP/SqFtSP/LPDIMScore
50 Eastfield DriveRolling Hills199907/22/2026566,60073,586$6.00M$5.20M$7880.8743481
100 SaddlebackRolling Hills195207/06/2026676,269187,893$7.50M$6.70M$1,0690.8911163
7 Acacia RoadRolling Hills193708/19/2026465,63075,720$7.00M$6.90M$1,2260.994362
Total: 3 · Average5.06.36,166.333112,399.667$6.27M$6.27M$1,027.667—196
Median6,269$6.70M$6.70M

Market Analysis

List vs Sale $/SqFt

Sale Price Trend

Days on Market

Sale vs List Price

AI-generated CMA

This analysis was generated automatically from MLS data. For an in-depth, human-reviewed valuation, contact Joseph Sardella at josephsardella@gmail.com.