Southshore Hills belongs to the years when Westlake Village was moving off the valley floor and onto the slopes around its new lake. The land had been cattle range since the Russell brothers bought it in 1881; it passed to William Randolph Hearst in 1925 and to Fred Albertson in 1943, whose Albertson Company ran it as a working ranch and a movie location. In 1963 the American-Hawaiian Steamship Company, controlled by the shipping magnate Daniel K. Ludwig, bought the 12,000-acre Albertson Ranch straddling the Los Angeles–Ventura county line for about $32 million and, with Prudential Insurance as its partner, hired A. C. Martin and Associates to master-plan a new community. The plan put a 125-acre man-made lake at the center, with about eight miles of shoreline, and organized the rest of the ranch into residential neighborhoods separated by greenbelts, parks and open hillsides. The lake was built in 1969, and its western arm curls south toward Westlake Boulevard; the hill that rises from that arm, south of Triunfo Canyon Road, is Southshore Hills.

The flat ground went first. Foxmoor, on the south bank of Potrero Valley Creek west of the boulevard, was built in 1968 and 1969, and the first Village Homes phase along Triunfo Canyon Road followed in 1969. County records date the first and larger phase of Southshore Hills to 1970: two-story and single-story homes of roughly 2,650 to 3,260 square feet on Highgate Road, Kelmscott Court, Folkestone Terrace, Woodburn Avenue, Bowcliff Terrace, Elmsbury Road and Bayside Court, sold through the local multiple listing service as “Southshore Hills-720.” The county recorded the subdivision as Tract 1998, and the legal descriptions on parcels throughout the hill still read that way. A second, smaller phase of single-story homes of about 2,040 to 2,140 square feet was built on Hillsbury Road in 1974 through 1976, and the Glastonbury Road and Channelford Road lots between and above them were developed later still, from 1974 into the 1980s, as a separate tract. The builder was designing for a different buyer than Foxmoor’s: the lots were graded as terraces of 10,000 to 30,000 square feet, many of them flag lots reached by a private drive, and the plans were larger, with cathedral ceilings, three-car garages and living rooms that faced the view rather than the street. The English street names, Highgate and Kelmscott and Folkestone, carried the same marketing voice the master plan used across the valley.

The political geography was settled while the first homes were being framed. In 1968 and again in 1972 the Ventura County portions of the master plan were annexed into the City of Thousand Oaks, so Southshore Hills has been inside Thousand Oaks city limits from the start. The Los Angeles County third of the plan, 3,456 acres, incorporated as the City of Westlake Village on December 11, 1981, and because a California city cannot straddle two counties, the Ventura side kept its Westlake Village mailing addresses while taking its police contract, its building department and its parks from Thousand Oaks and the Conejo Recreation and Park District. A Southshore Hills owner therefore pays Ventura County property tax, pulls permits from Thousand Oaks and sends a child to a Conejo Valley Unified school, all with a Westlake Village 91361 address on the mailbox, and the parcels carry the Thousand Oaks zoning code R1-13, which in the city’s system denotes single-family lots with a minimum size in the 13,000-square-foot range; buyers who plan to build should confirm the standard with the city.

What the master plan gave Southshore Hills, beyond the view, was its edges. The lake and the private lakefront tract of Windward Shores close the east side, Westlake Boulevard closes the west, Triunfo Canyon Road runs along the bottom, and above the last cul-de-sacs the ridge is open hillside toward Three Springs. In 1983 the park district opened Southshore Hills Park on four hilly acres at Glastonbury and Channelford Roads in the middle of the neighborhood, which is where the tract’s children have played ever since. Fifty-five years on, the neighborhood still reads as the planners drew it: a hill of large lots with a park in the middle, the lake below and the mountains behind. Gary Jacobs has worked in and around the south shore of Westlake Lake for years and keeps the original plan sheets for the tract on file.

Southshore Hills sold as MLS tract 720, and the Conejo Simi Moorpark Association of Realtors plan archive holds fifteen sheets for it: four named plans, the Aventine, the Birchmont, the Cherrywood and the Treemont, a numbered series from Plan 1 through Plan 8, and three variant sheets labeled Plan 300W Aventine, Plan 18 Cherrywood and Plan 17W Treemont. The named plans and their variants belong to the 1970 phase and the numbered plans appear to be the later series on Hillsbury Road, though the archive does not label them by year and Gary confirms the plan on any given house from the drawing itself rather than the name. What they share is the vocabulary of a 1970 Westlake Village hillside tract: living rooms with cathedral or vaulted, exposed-beam ceilings, brick fireplaces, formal dining rooms, family rooms opening to a rear patio, and attached garages, many of them three-car on the larger plans. The most common footprints in county records are the 2,808- and 2,823-square-foot two-story homes with four or five bedrooms and three baths that turn up on Highgate Road, Kelmscott Court, Bowcliff Terrace, Elmsbury Road and Folkestone Terrace, followed by a 2,654-square-foot four-bedroom on Woodburn Avenue and Bayside Court, a 2,944-square-foot four-bedroom on Woodburn Avenue, and a 3,263-square-foot five-bedroom on Highgate Road; the single-story homes record at about 2,300 and 2,625 square feet in the 1970 phase and at 2,038 to 2,140 square feet on Hillsbury Road. Gary Jacobs keeps the plan sheets on file and can tell a buyer which plan a given house started as and what has been added since.

Drawings on file for the tract. Other plans, elevations and options may have been offered.

What the plans mean on the ground today: county records put the median Southshore Hills home at about 2,290 square feet, with the tenth-to-ninetieth percentile running from roughly 2,040 to 2,820 square feet, and the largest at about 3,800 square feet after a 2021 rebuild. That is a narrower spread than the lots would suggest, and it reflects a tract where most owners have remodeled inside the original walls rather than added to them. The changes buyers see most often are the ones the 2026 listings describe: a 2018 kitchen with granite and stainless appliances behind a 1970 cathedral ceiling at 2205 Highgate Road, a 2022 tile roof and a recent furnace over an otherwise original 1974 single-story at 2236 Hillsbury Road, owned solar and a rebuilt kitchen at 2024 Woodburn Avenue, and a full renovation with a pool house and a car charger on the 0.67-acre flag lot at 2252 Hillsbury Road. Buyers should compare the county’s recorded square footage to the original plan and ask the City of Thousand Oaks for the permit history on any home that measures more than a few hundred feet over it, and should expect original-era galvanized plumbing, single-pane aluminum sliders and 100-amp panels on homes that have not been systematically updated. On a hillside, the inspection should also cover the retaining walls, the slope drainage and the condition of any deck or view patio, because those are where a 1970 terrace lot shows its age first.

Southshore Hills is a hill with clear edges and a simple plan. Triunfo Canyon Road runs along the bottom, parallel to the lake’s southwestern arm; Westlake Boulevard closes the west side; the lakefront circles of Windward Shores close the east; and above the highest cul-de-sacs the slope runs up to open hillside. Inside those edges the two spines are Highgate Road and Hillsbury Road, which climb from the Triunfo Canyon Road side and wind across the face of the hill. Highgate Road carries the 1970 phase, with house numbers from the 1980s to the 2360s on lots of about 9,500 to 19,000 square feet, and the short courts and terraces open off it: Kelmscott Court, whose 2224 sits perched at the end of the cul-de-sac on 16,089 square feet with valley views, and 2279 on half an acre; Bowcliff Terrace, where 1766 sold in September 2024 with a primary-suite balcony looking over the lake and the mountains; Folkestone Terrace, Woodburn Avenue, Elmsbury Road and Bayside Court, a cul-de-sac of seven 1970 homes. Hillsbury Road, with house numbers from the 2030s to the 2340s, is where the 1974 single-story phase went in, and its lots are among the largest on the hill: 2141 Hillsbury Road sits on 34,757 square feet, 2252 on 0.67 acre and 2236 and 2237 on a third to four tenths of an acre each.

The lots deserve a paragraph of their own, because so many of them are flag lots. A flag lot is a parcel whose house sits behind a neighbor’s, reached by a long private driveway that forms the pole of the flag; on a hillside it is the surveyor’s way of fitting a second row of homes above the first without a second street. 2205 Highgate Road, 2226 Highgate Road, 2236 Hillsbury Road and 2252 Hillsbury Road all sold or listed as flag lots between 2022 and 2026, and their listings use the same two words, privacy and views, for the same reason: the house sits back from the road, above the roofline in front of it. The cost is a long driveway to maintain, a shared or easement access on some parcels, and a lot whose square footage includes a strip of pavement and a bank. A buyer should walk the pole as well as the flag and read the title report for any access easement before assuming the whole parcel is usable.

Every street in Southshore Hills

Home counts come from the Ventura County master address file for tract 720; median lot sizes are measured from county parcel geometry. Two addresses on Triunfo Canyon Road and one on Tanbark Road round the tract out to 262.

Two boundary points matter when reading listings. First, the two roads that run through the middle of the hill around Southshore Hills Park do not split the way the map suggests. Every one of the 32 homes on Channelford Road is recorded in the multiple listing service as tract 720, Southshore Hills, and dated 1974. Glastonbury Road straddles the line: 51 of its homes are recorded as The Bluffs, tract 751, and ten as Southshore Hills. A Glastonbury listing therefore has to be read address by address, and the association line is the quickest tell, since the two tracts carry different dues. Second, the name Southshore Hills is sometimes attached in listing and county data to Foxmoor Hills streets and the reverse, and the older Highgate Road and Kelmscott Court homes appear in some Foxmoor Hills datasets although they are on the far side of Westlake Boulevard from that tract. The reliable marker is the tract number on the preliminary title report, Tract 1998 for Southshore Hills, and Gary keeps the tract-720 streets sorted from the look-alikes.

The defining feature of Southshore Hills is the combination of elevation and water. The tract climbs from Triunfo Canyon Road toward the ridge, and the lots on the upper terraces look north and east over the southwestern arm of Westlake Lake, across the lake basin to the Conejo hills and, on the highest streets, south toward the Santa Monica Mountains. Listings describe it consistently: 1766 Bowcliff Terrace closed in September 2024 with a primary balcony and “panoramic mountain and lake views”; 2226 Highgate Road, a single-level home on a gated flag lot, sold in August 2022 on the strength of panoramic views of Westlake Village; 2224 Kelmscott Court closed in February 2025 with valley views from the end of its cul-de-sac; 2205 Highgate Road sold in April 2026 with mountain views from its pool and gazebo; and 2141 Hillsbury Road sold in May 2026 with views over the homes below and the hills beyond. What varies is the direction and the degree, and on a hillside those depend on the exact lot, the neighbor’s trees and the roofline in front, so a buyer should judge the view from the actual patio at the actual time of day and not from the photographs. The seller of 2236 Hillsbury Road put it plainly in the 2026 listing: the owners had preferred privacy and trees over the sweeping view the lot could have had, and the deer, rabbits and coyotes that came with them.

The lake itself is close but not shared. Westlake Lake is a private lake; boating and fishing are restricted to residents of the lake associations and their guests, the docks belong to the lakefront tracts such as Windward Shores at the bottom of the hill, and a Southshore Hills home carries no lake rights. What the tract has instead is the sight of the water, which for many buyers is the better half of the bargain: the lakefront homes on the circles below sit on 5,000-square-foot lots and pay lake assessments, while a Highgate Road home on a third of an acre looks down on the same water for a fraction of the dues. The Landing on the north shore and the restaurants along Triunfo Canyon Road and Westlake Boulevard are the places to get onto the lake’s edge, and lakefront neighbors with electric boats are a common sight from the upper decks.

The lots are the other half of the story. County records show a median of about 14,800 square feet, or 0.34 acre, with the tenth-to-ninetieth percentile running from roughly 9,600 to 34,400 square feet and several parcels over half an acre. On the flat streets of Westlake Village a lot that size is rare; here it is the norm, and it explains why Southshore Hills has pools on many of its parcels, basketball courts, gazebos and pool houses that the lakefront tracts cannot fit. The catch is that much of a hillside lot is slope. A 16,000-square-foot parcel may have 7,000 usable feet on the pad and the rest in a bank above or below the house, and a flag lot spends part of its area on the driveway, so buyers should walk the lot with a grading plan in mind rather than assume that a large lot means a large yard. Three practical points follow. Slope drainage and retaining walls are a standard inspection item here. The tract sits below open hillside mapped by the Ventura County Fire Department for fire hazard, and the Woolsey Fire of November 2018, which burned nearly 97,000 acres and forced evacuations in Thousand Oaks and Westlake Village, is recent enough that buyers on the upper streets should confirm the parcel’s fire-zone designation, the brush-clearance requirements and the insurance picture before writing an offer. And a home with a long history of the same owner should be checked for deferred work on the banks and the drains behind the walls.

The first reason people choose Southshore Hills is the view of the water without the price of the water. A lakefront home on the circles of Windward Shores below the hill sits on about 5,000 square feet and traded at a median of about $2.17 million in 2024–2026; a Highgate Road or Bowcliff Terrace home on a third of an acre with the lake in the window traded at $1.6 million to $1.85 million, with room for a pool, a three-car garage and a basketball court, and with association dues of $50 to $60 a month instead of a lake assessment.

The second is the lots. A median parcel of 14,800 square feet, many of them flag lots set back from the street, gives the tract a privacy that the flat Westlake Village neighborhoods cannot offer; the 2026 listings describe treehouses, pool houses, gazebos, orchards of native plants and wildlife in the yard, and every one of them is on a lot that a Foxmoor or Village Homes buyer would call an estate.

The third is the single-story phase. The 1974 homes on Hillsbury Road, at 2,040 to 2,140 square feet on lots from a third of an acre to eight tenths, are among the few one-level houses with land and a view on the Ventura County side of the lake, and the buyers who need one, downsizers and families with a parent at home, have paid the tract’s highest prices per square foot for them.

The fourth is the park. Southshore Hills Park is inside the neighborhood, not across a road from it, and its 2021 playground and lighted court are the sort of small amenity that shows up in daily life more than a clubhouse would.

The fifth is the schools and the address. The tract feeds Westlake Elementary, Colina Middle and Westlake High, all within three miles, and it carries a Westlake Village 91361 mailing address with Thousand Oaks services and Ventura County property tax, which some buyers prefer to the Los Angeles County side. And the sixth is that it is small: with about 262 homes and a handful of sales a year, the neighborhood keeps its owners, and the homes that do come to market tend to sell in weeks.

Anyone who looks up Southshore Hills sales will see a $7,300,000 closing on Highgate Road in 2026 and wonder what it means for a 1970 tract home. The answer is that it means very little. 1985 Highgate Road is a new house, completed in 2025, of about 8,071 square feet with five bedrooms and six baths on a 2.01-acre parcel overlooking protected open space; it came to market in October 2025 at $9,150,000, was reduced twice, and closed in the spring of 2026 at $7,300,000 after 181 days. Its listing carries its own association, shown as Highgate Estates with dues of about $650 per month, and its own subdivision name. It is an estate enclave at the top of the road, not a Southshore Hills-720 home, and the county’s neighborhood statistics sweep it in only because it shares a street name.

What the sale does tell a Southshore Hills owner is where the ceiling sits on this hill. The buyer paid about $900 per square foot for new construction with canyon and sunset views two turns above the 1970 homes, which is roughly $200 to $300 more per foot than the tract’s renovated homes fetch, and it confirms that the view and the address will support a rebuild when the lot is large enough. It also gives Gary a cautionary example for pricing: an automated valuation that averages the $7.3 million sale into a tract whose next-highest closing was $1.85 million will overstate every house on the hill. Buyers and sellers should read the recent Southshore Hills sales as a set that runs from about $1.4 million to $1.9 million, and treat the estate above as a different market that happens to share a road.

Every home in the tract belongs to a property owners association that listings call the Southshore Hills POA, and the first thing to know is how little it costs. MLS listings have reported the dues fairly consistently across two decades: $548 a year on a 2008 closing on Bayside Court, $135 a quarter on a 2019 closing on Hillsbury Road, $700 a year on a September 2020 closing on Highgate Road, $50 a month on an August 2022 closing on Highgate Road, $60 a month, or about $725 a year, on the September 2024 sale of 1766 Bowcliff Terrace and the February 2025 sale of 2224 Kelmscott Court, $50 to $60 a month on the 2026 listings on Highgate Road, Hillsbury Road and Woodburn Avenue, and $600 a year on the June 2026 closing on Fallview Road. Two 2026 closings on Hillsbury Road reported far lower figures, under $20 a month, which is more likely a data-entry difference than a second dues schedule, but it is a reminder that a listing is not a disclosure. Taken together the dues run somewhere between $540 and $725 a year, which is a fraction of what the lakefront and gated tracts pay and reflects what the association actually owns: listings describe the common area as greenbelt and slopes, with no pool, clubhouse, tennis court or gate to maintain.

The association is professionally managed, but the name of the manager has moved. The 2020 Highgate Road closing named Property Management Professionals LLC; the April 2026 closing of 2205 Highgate Road named Tandem Property Management; and the 2026 listings on Woodburn Avenue and Hillsbury Road named Community Property Management. Whether that is a change of contract or a difference in how three agents filled in the same field, a buyer’s agent should confirm the current manager, the current dues and the reserve position from the seller’s HOA disclosure package rather than from a listing or a third-party directory; no association website or phone number for the Southshore Hills POA was found in public sources at the time of writing, and buyers should be careful not to confuse it with the identically named property owners association on Torch Lake in Michigan whose website appears first in a search. Despite the low dues, the association’s architectural authority is real: the CC&Rs govern exterior changes, and a buyer planning a second story, a new roofline, a driveway change or a front-yard makeover should read the CC&Rs and ask the seller for any open violation notices before writing the offer.

There is no gate; the streets are public and maintained by the City of Thousand Oaks. Mello-Roos and other special-district assessments are not typical of 1970s tracts in Westlake Village, but the direct assessments on any parcel’s Ventura County tax bill should be confirmed in escrow. And because the neighborhood name is applied loosely in directories, the reliable sources are the preliminary title report, which will show Tract 1998, and the seller’s association disclosures.

Southshore Hills is on the Ventura County side of Westlake Village, so it is in the Conejo Valley Unified School District, not Las Virgenes. The assigned schools shown on recent MLS listings throughout the tract, on Highgate Road, Hillsbury Road, Kelmscott Court, Bowcliff Terrace and Woodburn Avenue, are Westlake Elementary (kindergarten through fifth grade), Colina Middle School and Westlake High School. Westlake Elementary, at 1571 East Potrero Road in Foxmoor on the other side of Westlake Boulevard, is about 0.8 mile from a Highgate Road front door; the route is down the hill to Triunfo Canyon Road, across the boulevard and into the Foxmoor greenbelt, which many families walk or bike. Colina Middle School is at 1500 East Hillcrest Drive in Thousand Oaks, about three miles away by Westlake Boulevard and Hillcrest Drive, and Westlake High School, which opened in 1978 at 100 North Lakeview Canyon Road, is a little under two miles away on the north side of the lake with roughly 2,000 students and a long record of strong state rankings.

One caution. Older neighborhood write-ups sometimes list Westlake Hills Elementary rather than Westlake Elementary for this part of Westlake Village, and attendance boundaries do change. The recent listing data across the tract all point to Westlake Elementary, but the district, not a listing, is the authority, and families should verify the assignment for the specific parcel with Conejo Valley Unified before making an offer, which Gary does on every transaction here. Private options in the area include Oaks Christian School in Westlake Village.

Southshore Hills has its own park in the middle of the hill. Southshore Hills Park, at the corner of Glastonbury Road and Channelford Road, is a four-acre Conejo Recreation and Park District facility that the district describes as hilly and passive: a playground rebuilt in 2021 as a boat-themed structure with hill climbers, a lighted outdoor basketball court that stays lit until 10 p.m., a backstop, two barbecue grills and two picnic tables, on a slope with trees and a view. It opened in 1983 and is open from 7 a.m. to 10 p.m. every day. It is not a sports complex, and that is the point; it is the kind of park a family with a stroller or a child on a bike uses every afternoon, and most of the tract can walk to it without crossing a through street. For fields and courts, Triunfo Community Park at 980 Aranmoor Avenue, about a mile north across Triunfo Canyon Road in Village Homes, has three lighted tennis courts, ball fields, soccer fields and a sand volleyball court, and it is the trailhead for the Triunfo Canyon Trail up to the Los Robles Trail East on the ridge.

The lake is the other daily presence. The Landing, on the north shore at Lindero Canyon Road, holds the lakefront restaurants and the Westlake Yacht Club, which runs sailing instruction on the water; the shopping centers where Westlake Boulevard meets Triunfo Canyon Road and Agoura Road hold the grocery stores, banks, coffee and restaurants residents use daily, most of them within a mile of the bottom of the hill. Above the tract, the open hillside toward Three Springs and the ridge is the neighborhood’s backdrop; the formal trailheads for the Los Robles system are at Triunfo Community Park to the north and along Potrero Road to the south, and buyers who want a trail from their door should ask Gary which streets have informal access to the slopes and which do not.

Southshore Hills drains onto Triunfo Canyon Road and from there onto Westlake Boulevard, and Westlake Boulevard is the neighborhood’s road to everything. The US-101 interchange at Westlake Boulevard, signed as State Route 23, is about two miles north of the bottom of the hill, roughly five to seven minutes off-peak, past the shopping centers at Agoura Road and Townsgate Road; from the top of Highgate Road the trip is a few minutes longer because of the hill. Two alternatives keep the boulevard from being the only way out. To the east, Triunfo Canyon Road runs along the south shore of the lake past the Westlake Island bridge to Lindero Canyon Road on the Los Angeles County side, which serves the office parks along Lindero Canyon and Agoura Road, the Lindero Canyon interchange and The Landing at 32129 Lindero Canyon Road on the north shore. To the west, Triunfo Canyon Road continues past Village Homes and Triunfo Community Park to the west end of Westlake Village, and from there Thousand Oaks Boulevard leads to the Hampshire Road interchange, which is the better route toward Thousand Oaks and The Oaks mall. Commute hours on Westlake Boulevard are real, especially at the freeway ramps in the afternoon, and residents learn to use Agoura Road and Thousand Oaks Boulevard as bypasses.

Errands are close. The nearest full grocery stores are Vons at 2725 Agoura Road and Gelson’s at 2734 Townsgate Road in Westlake Plaza, both at the north end of Westlake Boulevard within about two miles of the tract; Ralphs at 3963 East Thousand Oaks Boulevard and Trader Joe’s at 3835 East Thousand Oaks Boulevard sit together on the Ventura County side east of the boulevard, a short drive north of the freeway. The Promenade at Westlake, off Thousand Oaks Boulevard near Westlake Boulevard, holds the neighborhood’s cinema, restaurants and specialty shops, and The Oaks in Thousand Oaks, the regional mall at Hillcrest Drive and Lynn Road, is about fifteen to twenty minutes west off-peak. Amgen’s headquarters campus in Thousand Oaks and the Westlake Village and Agoura Hills office parks are the large employers within roughly a fifteen-minute drive off-peak.

The rail and bus picture is thin, as it is across the Conejo Valley. The nearest Metrolink stations on the Ventura County Line are Moorpark, at 300 High Street, reached by State Route 23 north from the freeway, and Simi Valley; the line runs ten trains in each direction on weekdays, with most turning at Moorpark, and Moorpark is also served by Amtrak’s Pacific Surfliner. Driving to Moorpark station takes roughly twenty to thirty minutes off-peak, so a Southshore Hills owner who rides the train is a park-and-ride commuter. Thousand Oaks Transit’s fixed routes serve central Thousand Oaks and its transit center at 265 South Rancho Road, from which LADOT commuter routes run to downtown Los Angeles on weekdays; service to Westlake Village itself is limited and buyers who need it should check the current routes rather than assume a stop.

The coast is the other direction. Westlake Boulevard becomes State Route 23 south of Potrero Road and climbs over the Santa Monica Mountains to Mulholland Highway and Decker Canyon to Pacific Coast Highway west of Malibu, a winding drive of roughly forty-five minutes to an hour; the more common route is Kanan Road, which begins at Westlake Boulevard and runs to the freeway in Agoura Hills, then continues as Kanan Dume Road for about twelve and a half miles through three tunnels to PCH at Zuma, in the same range of time. School runs are short: Westlake Elementary is under a mile across the boulevard, Colina Middle School on East Hillcrest Drive is about three miles to the north, and Westlake High on North Lakeview Canyon Road is a little under two miles by Triunfo Canyon Road and the north shore, with the morning queue on Lakeview Canyon the one to plan around. All of these times are rough, off-peak ranges; a buyer should drive the route at the hour that matters.

The figures in this section were current when this guide was last reviewed. The sale record in the facts above and the listings below are drawn live from the MLS each time the page loads.

Southshore Hills is a small tract, and it trades in small numbers: in the two years through June 2026, 20 homes in the tract sold through the MLS, at prices from $1,500,000 to $2,850,000 and a median of $1,750,000. The new-construction estate at the top of Highgate Road is a separate enclave, and the working range for the 1970s homes has been roughly $1.4 million to $1.9 million. The closings tell the story better than the median. 1766 Bowcliff Terrace, a 2,808-square-foot four-bedroom of 1970 with a remodeled kitchen, a pool and a balcony over the lake, was listed at $1,725,000 and closed in September 2024 at $1,630,000, about $580 per square foot. 2224 Kelmscott Court, a 2,625-square-foot single-story three-bedroom of 1970 with vaulted beamed ceilings, new floors and an original brick fireplace on 16,089 square feet at the end of the cul-de-sac, was listed in November 2024 at $1,650,000 and closed in February 2025 at $1,550,000, about $590 per foot. In the spring of 2026 the market firmed: 2205 Highgate Road, a 2,808-square-foot five-bedroom of 1970 on a 12,632-square-foot flag lot with a pool, a spa, a gazebo, a three-car garage and a 2018 kitchen, listed at $1,875,000 on March 23 and closed at $1,850,000 on April 14, twenty-two days later, about $659 per foot; 2141 Hillsbury Road, a 2,140-square-foot one-story four-bedroom of 1974 on 0.8 acre, listed at $1,500,000 on March 25 and closed at full price on May 1, about $701 per foot; and 2236 Hillsbury Road, a 2,038-square-foot single-story four-bedroom of 1974 on a 14,374-square-foot flag lot with a 2022 tile roof, listed at $1,495,000 and closed in June at $1,430,000, about $702 per foot.

Two listings were in escrow as this guide was written. 2252 Hillsbury Road, a renovated 2,823-square-foot three-bedroom of 1970 on a 0.67-acre flag lot with a heated pool, a pool house, a treehouse and an EV charger, came to market on August 18, 2026 at $1,899,999, about $673 per foot, and went pending within a week; it had last sold in September 2011 for $915,000. 2024 Woodburn Avenue, a 2,654-square-foot four-bedroom of 1970 on a 7,840-square-foot lot, one of the smaller parcels on the hill, with owned solar, a newer furnace and water heater and a wet bar, listed on July 6, 2026 at $1,798,000, was reduced to $1,698,000 on August 4 and went under contract at about $640 per foot. The longer record fills in the trend: 2227 Highgate Road, a 2,823-square-foot two-story, sold for $924,000 in July 2014, $1,185,000 in December 2018 and $1,330,000 in September 2020; 2237 Hillsbury Road, a 2,040-square-foot single-story with views, sold for $1,225,000 in August 2019; and 2226 Highgate Road, a 2,300-square-foot single-level home on a gated 0.43-acre flag lot with a pool, sold for $1,595,000 in August 2022, about $693 per foot, after being marketed furnished for short-term lease at $12,500 a month.

Read together, the numbers say three things. Turnkey single-story homes on the big Hillsbury Road lots earn about $700 per square foot, the top of the tract, because the pool of buyers who want one level, a view and land is deep and the supply is a couple of homes a year. Renovated two-story 1970 plans of about 2,800 square feet with a pool earn $1.6 million to $1.9 million depending on the lot and the kitchen, or roughly $580 to $675 per foot. And the spread between an original home and a remodeled one is real but smaller than in Foxmoor Hills, because fewer Southshore Hills homes come to market in original condition; most have had at least one kitchen. Days on market for a well-priced home in 2026 ran from one week to five, and the two 2024–2025 sales that closed five to six percent under their asking prices, on Bowcliff Terrace and Kelmscott Court, were listed in the softer market of that fall and winter at $1.65 million and above and took two to three months to find their buyer.

Figures are drawn from public records and MLS closings and are rounded. They are a snapshot, not a valuation; contact Gary for a current read on any specific property.

Southshore Hills is an owner neighborhood first, and homes come up for lease only a few times a year, but the two on the market in the late summer of 2026 set the rate clearly. 2344 Highgate Road, a 2,822-square-foot five-bedroom, three-bath 1970 home with a fireplace, was offered at $6,800 per month on a twelve-month lease, and 1504 Folkestone Terrace, a 2,823-square-foot four-bedroom, three-bath of the same plan with hardwood floors, was also offered at $6,800 per month. That is about $2.40 per square foot for the tract’s most common two-story plan, a little under the $2.75 to $3.00 per foot that renovated homes with pools have been fetching in Foxmoor Hills across the boulevard, where Gary Jacobs leased 1267 Willsbrook Court at $6,800 per month in June 2024 and $6,900 in August 2025, and under the $7,450 asked for a 2,683-square-foot five-bedroom with a pool on Stonesgate Street in the same season. The difference is condition and pool rather than address; a Southshore Hills home of 2,800 square feet with a pool, a renovated kitchen and the view should lease in the low to mid $7,000s, and one in original condition in the mid $6,000s. At the other end of the scale, 2226 Highgate Road was marketed furnished for short-term stays at $12,500 a month before it sold in 2022, which shows what a view home with a pool can ask from a corporate or relocation tenant on a short term, though that is a different market from a twelve-month lease.

Who rents here is as telling as what they pay. A five-bedroom hillside house at $6,800 a month is not a starter rental; the tenants tend to be families relocating into the Westlake High attendance area while they buy, executives on assignment with the Conejo Valley’s larger employers, and households rebuilding or remodeling elsewhere in Westlake Village. Landlords should expect tenants to ask for the gardener and any pool service to be included and to ask about pets. Homes are typically offered unfurnished on a standard California residential lease: a security deposit that under current state law is generally capped at one month’s rent for most landlords, a written lease of twelve months in most cases, and the usual disclosures for a 1970 home, including lead-based paint.

Two practical notes. No leasing restriction for the Southshore Hills association was found in public sources, and MLS listings in the tract have offered homes for lease without reference to a minimum term, but the CC&Rs govern and an owner planning to rent should read them before signing a tenant. And because the parcel is in the City of Thousand Oaks, not the City of Westlake Village, any rental-registration or short-term-rental rule comes from Thousand Oaks; Gary confirms the current rules for owners weighing a lease against a sale, and his leases in Foxmoor Hills and Village Homes give him a direct read on the tenant pool and the rent a turnkey home on this side of the lake will hold.

Most of Southshore Hills was built in 1970 and the rest in 1974 through 1976, and a general inspection here follows the pattern of an early-1970s Conejo Valley tract with a hillside overlay. The following are common in homes of this era; each house varies, many have been updated once or twice, and a licensed inspector must confirm the condition of any specific property. Nothing here describes a particular address.

Inside the walls, the original water supply lines were galvanized steel, and after fifty-five years those that have not been replaced with copper or PEX are usually near the end of their life, showing as low pressure at upstairs fixtures and rust at the connections. Drain lines were cast iron or early ABS plastic; a sewer camera run from the cleanout to the street is the single most useful add-on inspection in the tract, because the laterals are long on flag lots and hillside parcels and root intrusion and bellied pipe are common. Electrical panels of this period were often Zinsco or Federal Pacific, both of which most inspectors and insurers now flag for replacement, and the original service was typically 100 amps, which is light for a home with a pool pump, an electric vehicle charger and central air; a few early-1970s Southern California tracts also used aluminum branch wiring for the 15- and 20-amp circuits, so an inspector should open a few outlets and the panel to confirm what is in the walls. Original windows were single-pane aluminum sliders, and a home that still has them will also usually have the original insulation levels in the attic and none in the walls. The listings that mention dual-pane windows, as the 2008 Bayside Court listing did, are telling the buyer that work has been done.

Overhead and underfoot, the homes sit on slab foundations, and on a terraced hillside lot the inspection should include moisture readings at the slab edge, the condition of the drains behind any retaining wall, the swales and area drains on the pad, the long driveway on a flag lot, and any settlement or cracking in the walls that hold the terraces. Roofs have generally been replaced at least once since 1970; concrete tile and composition shingle are both common now, and a tile roof can look sound from the street while the underlayment beneath it has failed, which is why the 2022 roof at 2236 Hillsbury Road was a selling point. Furnaces and ducting are usually in the attic, and older ducting loses a share of the conditioned air before it reaches the rooms. Pools are on many of these lots and the equipment has its own timeline: heaters, pumps and filters last ten to fifteen years, and a pool that has been in place since the 1970s may have been replastered several times and re-plumbed once.

Because the lots are large, an inspector should compare the house to the county’s recorded square footage and the original plan. Room additions, enclosed patios, converted garages and pool houses that do not appear in the City of Thousand Oaks permit history are the most common source of a post-inspection renegotiation here. Finally, the tract sits below open hillside mapped for fire hazard; buyers should confirm the parcel’s zone, the vegetation-clearance requirements and the insurance picture early in escrow rather than at the end.

The sales record in Southshore Hills rewards two things above all: one level, and the view. 2141 Hillsbury Road, a 2,140-square-foot single-story of 1974 with a granite eat-in kitchen and level patios on 0.8 acre, sold at full price in May 2026 at about $701 per square foot, and 2236 Hillsbury Road, the same era and size with a new roof but a mostly original interior, sold a month later at $702 per foot; the tract’s two-story plans in the same season closed at $580 to $675. A single-story home with a renovated kitchen and primary bath on a flag lot with a view is the most valuable thing on this hill per square foot, and it is worth more here than the cost of the work, because the buyers who want it, downsizers from the larger Westlake Village tracts and families who need a bedroom on the main floor, cannot find it in the lakefront or gated neighborhoods.

What gets done to the two-story plans is consistent. The 1970 layouts separate the kitchen, nook, family room and dining room with walls that are mostly non-bearing, and the standard remodel removes them into one room that opens through new sliders to the patio and the view; the living room with its cathedral or vaulted beamed ceiling is almost always kept, as it was at 2205 Highgate Road and 2224 Kelmscott Court, and smoothing the ceilings and replacing the aluminum sliders with dual-pane units are the two changes buyers see first. Upstairs, the original primary suite has a compact bath and a dressing area, and the common expansion takes the adjacent bedroom into a larger bath and closet, trading a five-bedroom for a four-bedroom with a real suite; the 1766 Bowcliff Terrace listing’s custom walk-in closet and view balcony is the finished version. Outdoors is where Southshore Hills differs from the flat tracts: the lots are large enough for the pool house at 2252 Hillsbury Road, the gazebo at 2205 Highgate Road and the basketball court at 2227 Highgate Road, and a renovated outdoor room facing the view has been part of every top sale in the tract. Owned solar, which 2024 Woodburn Avenue and 2226 Highgate Road both advertised, has become a standard line item that tenants and buyers now ask about.

Whole-house rebuilds and second stories are rarer here than in Foxmoor Hills, because most Southshore Hills lots already hold a 2,800-square-foot house and the market pays well for the original plans; county records show one rebuild, in 2021, at about 3,800 square feet, and the $7.3 million new house at the top of Highgate Road is a separate enclave on two acres. The lots do make the tract one of the better Westlake Village neighborhoods for an accessory dwelling unit. Under California law a single-family owner may generally build a detached ADU of up to 1,200 square feet, or an attached unit of up to half the primary home’s floor area, and a junior ADU of up to 500 square feet inside the existing house; an ADU of up to 800 square feet cannot be denied on lot-coverage or floor-area grounds, and Civil Code section 4751 voids any association rule that effectively prohibits or unreasonably restricts one, though reasonable conditions on parking and appearance still apply. The City of Thousand Oaks, which issues the permits here, publishes pre-approved ADU plans and requires owner occupancy for a junior unit. The hillside is the constraint: a flag lot with a long driveway and a terraced pad may have room for a detached unit and may not, and grading, retaining and fire-zone construction standards can add more to the cost than the unit itself. Every one of these projects goes through the association’s architectural review, so a buyer planning work should read the CC&Rs before writing the offer and ask the seller for the approvals on any work already done.

The hill cuts both ways. A view lot is also a slope lot, and the inspection items that come with it, retaining walls, drains, a long driveway on a flag lot and the fire-hazard mapping above the tract, are real costs that a flat Westlake Village lot does not carry; insurance in the hillside zones has become more expensive and less predictable since the Woolsey Fire, and a buyer should get a quote before removing contingencies rather than after. The flag lots that give the neighborhood its privacy also bring shared driveways and access easements on some parcels, and a buyer should read the title report for them.

The homes are fifty-five years old. Most have been remodeled at least once, but galvanized plumbing, original panels, single-pane sliders and attic ducting are still found in the tract, and a home that has had a kitchen but not a re-pipe can look finished and still need $50,000 of systems work. Because the tract is small and the buyer pool wants turnkey, a home in original condition here can sit while the remodeled one next door sells in a week, which is good news for a buyer willing to do the work and a caution for a seller who is not.

The lake is a view, not an amenity. Southshore Hills has no docks, no lake access and no lake rights; a buyer who wants to put a boat in the water should look at Windward Shores or Westlake Island and pay the assessments. The association is light, which keeps dues low but also means no pool, no clubhouse and no gate, and buyers who want those should look at Village Homes or the gated tracts. The management company named on listings has changed, so the HOA disclosure package, not the listing, is the place to confirm dues and rules. And the neighborhood name is applied loosely: Glastonbury and Channelford Roads share the hill and the park but belong to a different tract without an association, and the $7.3 million sale on Highgate Road is a separate enclave, so a buyer reading comps should sort by tract number rather than by street.

The most consistent buyer in Southshore Hills is the family moving up from a flat Westlake Village tract, Foxmoor, Village Homes or Westlake Hills, who has outgrown a 7,000-square-foot lot and wants a pool, a three-car garage and a bedroom count of four or five without leaving the Westlake High attendance area; the 2,808- and 2,823-square-foot 1970 plans on Highgate Road, Bowcliff Terrace and Folkestone Terrace are built for them. The second is the one-level buyer: downsizers from the larger Three Springs and North Ranch homes and households with a parent or a child who cannot use stairs, who compete for the 1974 single-story homes on Hillsbury Road and the single-level 1970 plans on Kelmscott Court and Highgate Road, and who have paid the tract’s highest prices per foot for them. The third is the view buyer who priced the lakefront and decided the water is better seen from above, and the fourth is the privacy buyer who wants a flag lot behind a gate of their own rather than a guard gate shared with four hundred neighbors. Tenants, when homes lease, are relocating families and executives on assignment with the Conejo Valley’s larger employers, at $6,800 a month and up.

The closest comparison is Foxmoor Hills, the other 1969–1971 hillside tract on the Ventura County side, on the far side of Westlake Boulevard and Potrero Valley Creek to the northwest. The two neighborhoods are contemporaries with similar plans, similar lots and the same schools, and their listings are sometimes confused with each other. Foxmoor Hills is larger, at about 309 homes, with a median lot of about 12,600 square feet and a median sale since 2024 of about $1.725 million; Southshore Hills is smaller, with a larger median lot of about 14,800 square feet, more flag lots, the lake in the view and a median closer to $1.85 million for the tract homes. Foxmoor Hills dues are about $220 a year; Southshore Hills dues are about three times that, still nominal. Foxmoor Hills has the regional park and the Los Robles trailhead on its doorstep; Southshore Hills has its own small park and the water.

Village Homes, across Triunfo Canyon Road to the north, is the large planned unit development of about 654 homes built from 1969 to 1977 on lots of about 7,400 square feet, with a median sale of about $1.46 million since 2024 and an association that charges roughly $270 a quarter for a clubhouse, pool, spa, tennis courts and a central greenbelt. A buyer choosing between them is choosing between amenities on a small lot and land and a view with none. Windward Shores, at the bottom of the hill on the lake’s southwestern arm, is the lakefront answer: about 100 mostly single-story homes of 1973–1976 on 5,000-square-foot lots with private docks, a median sale of about $2.17 million and lake assessments on top of the tract dues. Westlake Island, reached by the guard-gated bridge from Triunfo Canyon Road a mile east, is the top of the lake market, with a median of about $3.05 million since 2024, every lot on the water and dues of about $850 a quarter plus the lake association. Price per square foot tells the story in one line: Southshore Hills tract homes closed at about $580 to $700 per foot in 2024–2026, Foxmoor Hills at roughly $650 to $700 for renovated homes, Windward Shores and the Island well above $1,000 for the water. The Westlake Village guide puts all of these tracts on one map.

Gary Jacobs has no recorded closings inside the Southshore Hills tract, and this guide says so plainly. His work on this side of the lake has been in the neighborhoods that Southshore Hills buyers and sellers are compared against: in Foxmoor Hills, where he leased 1267 Willsbrook Court, a renovated 2,465-square-foot 1969 home with a pool, at $6,800 per month in June 2024 and again at $6,900 per month in August 2025, and where he tracks the Stonesgate Street sales that set the hillside price per foot on the Ventura County side; in Village Homes, where he sold 2244 Silver Spring Drive in January 2017 and leased it four times before that; and on Westlake Island. He keeps the Southshore Hills plan sheets on file, the sales record for every street on the hill and the tract-720 parcels sorted from the Glastonbury Road and Highgate Estates look-alikes, and he offers the comparable sales from all four neighborhoods to any owner or buyer who asks.

Buyers: Read the tract number on the preliminary title report before trusting the neighborhood name on a listing; Southshore Hills is Tract 1998 and MLS tract 720, and Glastonbury Road, Channelford Road and the estate at the top of Highgate Road are not. Get the HOA disclosure package early and confirm the current dues, manager and any architectural or leasing rules from it, because the listings disagree. Walk the whole lot, including the driveway pole on a flag lot, with the grading and any easements in hand, and judge the view from the patio at the hour you will use it. Order a sewer camera, a panel and wiring check and a roof inspection that looks under the tile, and get a fire-insurance quote before contingencies come off. Well-priced homes here have gone pending in one to three weeks in 2026, so be ready to write when the right single-story or view home appears; there are only a few a year.

Sellers: Price to the tract, not to the hill’s outliers; an automated estimate that averages the $7.3 million Highgate Estates sale into the tract will overstate a 1970 home, and the 2024–2025 listings that came out in the slower fall and winter months at $1.65 million and above were the ones that took five to six percent cuts. Lead with the lot and the view, in that order, and stage the outdoor room facing them. Have the permit history for any addition, pool house or solar system ready, a recent roof and sewer report if the systems are original, and the association documents in the disclosure package before the first showing. A single-story home in turnkey condition should be marketed to one-level buyers across Westlake Village and Thousand Oaks, because they are the buyers paying $700 per foot here; a two-story plan with an updated kitchen and a pool should be priced against the 2026 Highgate Road and Bowcliff Terrace closings. Gary will pull the comps for the specific plan and street before setting a number.