Windward Shores exists because the lake it sits on was drawn into a master plan almost as an afterthought. In 1963 the American-Hawaiian Steamship Company, controlled by the shipping and oil magnate Daniel K. Ludwig, bought the 12,000-acre Albertson Ranch on the Los Angeles–Ventura county line for about $32 million and, in partnership with Prudential Insurance, hired the architectural and planning firm A. C. Martin and Associates to lay out a new town. The following year the Bechtel Corporation produced a planning study of the 11,780 developable acres, and its first drafts had no lake at all; the engineers were considering concrete or rock channels to carry Triunfo Creek through the valley floor. When an alternative that dammed the creek was put in front of Ludwig, he approved it, and McIntire and Quiros designed a 125-acre lake with a concrete gravity dam about 700 feet long and three stories high. Pascal and Ludwig Engineering began construction in 1965, the shoreline was sculpted from natural soil and concrete by Julian George using high-pressure water, and the whole project was finished in 1969 at a cost of about $3.5 million. The lake holds roughly 500 million gallons when full, averages about eight feet deep, and has a little over eight miles of shoreline, into which the designers cut coves, finger channels and the large central island that became Westlake Island.

The Ventura County side of the plan, 8,544 acres of it, was annexed into the City of Thousand Oaks in two pieces in 1968 and 1972, which is why Windward Shores has a Westlake Village mailing address, a Thousand Oaks building department and a Ventura County tax bill. The Los Angeles County side, 3,456 acres, incorporated as the City of Westlake Village on December 11, 1981. By then the shoreline had largely been built out. The first waterfront neighborhoods went up on the east and north shores in the late 1960s, First Neighborhood and Lakeshore among them, and Westlake Island filled in through the 1970s. The western arm of the lake, the stretch of water between Westlake Boulevard and the island bridge on the Ventura County side, was developed a few years later, and Windward Shores was part of that second wave: county records date the 23 homes on Windward Circle to 1973 and the 62 homes on Topsail and Leeward Circles to 1976.

What the builder was designing for is visible in the tract itself. By the mid-1970s the market for Westlake Village lakefront had matured, and the buyers were no longer only young families drawn by the novelty of a lake; they included empty-nesters and second-home buyers who wanted the water without stairs or a large yard. Windward Shores answered that with compact one-story plans of roughly 1,600 to 2,400 square feet on lots of about 5,000 square feet, arranged on three short loops so that as many houses as possible touched either the lake or a landscaped greenbelt leading to it. The street names, Topsail, Leeward and Windward, carry the sailing vocabulary that the developer used across the lake, on Westlake Island and elsewhere. In 1968 Ludwig had formed the Westlake Lake Management Association to own and run the lake and dam, and in 1974 he handed control of it to the homeowners, so the first Topsail and Leeward buyers in 1976 moved into a neighborhood whose lake was already governed by the people who lived around it. The identity of the merchant builder that bought the tract 733 lots from the Westlake Village developer and built the homes is not confirmed in the records Gary Jacobs has reviewed; the Conejo Simi Moorpark Association of Realtors archive preserves the five original plans by number rather than by a builder’s brand name.

Windward Shores was marketed as MLS tract 733, and the Conejo Simi Moorpark Association of Realtors plan archive holds five original floor plans for it, listed simply as Plan 1, Plan 2, Plan 3, Plan 4 and Plan 5. They share a single premise: one level in four of the five plans on file, a two-car garage on the street, and living space turned toward the water or the greenbelt behind the house. County records put the smallest homes in the tract at about 1,609 square feet with two bedrooms and two baths, the most common size around 1,800 to 2,000 square feet with three bedrooms, and the largest original plans a little over 2,400 square feet, so the plans on file were drawn in a tight band. Features that the 1976 listings still describe today, and that appear in the drawings, include vaulted ceilings in the living room and bedrooms, a private atrium or entry courtyard off the dining room, a family room open to the kitchen, and a primary bedroom at the rear with sliding doors to the patio and the lake. Gary Jacobs keeps the plan sheets on file and can identify which plan a given house started as.

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 show the middle of the tract at about 1,960 square feet, with the tenth-to-ninetieth percentile running from roughly 1,609 to 2,402 square feet, which means most Windward Shores homes are still close to their original footprint. That is unusual for Westlake Village lakefront. On Westlake Island a large share of the housing has been expanded upward or rebuilt; in Windward Shores the one-story character has held, with a single full rebuild dated 2010 in county records at about 4,500 square feet, and a handful of two-story records on Windward Circle. The typical remodel here is interior: the wall between kitchen and family room comes out, the atrium is either glassed in or made into a true courtyard, and the water-side wall is opened with wider sliders. A 2026 sale on Leeward Circle described exactly that program, an “open floor plan” with “walls of windows” toward the lake, in a house still recorded at 2,263 square feet. Buyers should compare the listed square footage against the county figure, ask the City of Thousand Oaks for the permit history on anything that looks enlarged, and treat the dock, where there is one, as a separate structure to be inspected on its own, since it belongs to the lake association’s permit system rather than to the house.

Windward Shores is three streets. Topsail Circle, Leeward Circle and Windward Circle are short loops that leave the mainland road on the south shore of the lake’s western arm and wind back on themselves, so no one drives through the neighborhood to get anywhere else. House numbers run from about 2350 to 2433 on all three, the low, four-digit numbering that marks the Ventura County side of Westlake Village, as opposed to the 31000- and 32000-block addresses across the county line. Topsail and Leeward each hold 31 homes in county street records and Windward 23, for 85 on the circles; the tract outline holds 92 parcels, and the difference is a handful of homes recorded under the adjoining road frontage. Either way it is one of the smallest named neighborhoods in Westlake Village, a fraction of the 446 parcels on Westlake Island next door or the 622 in Village Homes up Triunfo Canyon Road.

The two phases are visible in the records. Windward Circle, the 1973 street, has the smallest lots in the tract, a median of about 3,484 square feet, and slightly larger houses, about 1,960 to 2,440 square feet, along with the tract’s only two-story parcels; it reads as an earlier, denser piece of planning, closer in spirit to the attached lake-access homes of Northshore across the water, which also date to 1973. Topsail and Leeward, both 1976, have more conventional detached lots with medians around 5,200 to 5,700 square feet and homes from about 1,609 to 2,583 square feet. A buyer comparing a Windward Circle home with one on Leeward is comparing a slightly older, tighter site plan with a slightly newer and roomier one, and prices should be read with that in mind.

The lake sets the hierarchy of lots. Homes on the outer side of each loop back onto Westlake Lake itself, with a patio, a seawall maintained by the lake association and, in most cases, a private dock; homes on the inner side of the loop back onto the association greenbelt, a strip of lawn and trees that runs down to the water and gives every resident a way to reach the shore on foot. Both kinds are sold as Windward Shores and both pay the lake association, but the lakefront lots pay roughly twice the lake assessment and sell for roughly twice the price. The 2026 closings make the point: a renovated 2,263-square-foot lakefront home with a dock on Leeward Circle closed at $3,110,000 in April, and a remodeled 1,609-square-foot greenbelt home a few doors away, with “direct access to a spacious greenbelt which adjoins Westlake Lake,” closed at $1,500,000 in June. Position on the water matters too. The western arm is narrower than the main body of the lake, so some Windward Shores lots look across a few hundred feet of water at the homes of Westshore on the north bank or at the flank of Westlake Island, while the lots nearest the island bridge see more open water; the listing for 2398 Leeward Circle described “lake and mountain views,” which on the south shore means looking north across the water toward the hills above Village Homes and Westlake Hills.

Westlake Lake and its dam are private, owned and operated by the Westlake Lake Management Association, a nonprofit with about 1,300 member households in seven residential districts plus one commercial district, governed by a 33-member volunteer board. Buying in Windward Shores makes the owner a WLMA member, and the association’s rules, most recently republished in January 2026, decide what happens on the water behind the house. The office is at 32353 Triunfo Canyon Road, a short distance from the neighborhood, at (818) 889-5377, and day-to-day administration is handled by PMP Management.

The boats are small, slow and silent by rule, and that is the whole character of the lake. Nothing over 18 feet in length or 8 feet 6 inches in beam is allowed, and every powerboat must be electrically propelled, with exceptions only for the association’s work boats, approved vendors and the Westlake Yacht Club patrol boat. The speed limit is five miles an hour on the open lake and three in the finger basins. Multi-hulled sailboats, inflatables, windsurfers, jet skis, paddleboards and anything towing a skier are prohibited. Boating runs from an hour before sunrise until 11 p.m., with low-profile craft such as kayaks and rowing shells kept off the water after dark. Swimming is prohibited except for sailing training, an accidental fall or an emergency. Fishing requires an annual WLMA badge, plus a state license for anyone 16 or older, and is limited to an hour before sunrise until an hour after sunset. On a summer evening the western arm fills with Duffy-style electric boats heading east under the island bridge toward The Landing, where WLMA enforces a two-hour mooring limit at busy times with an hour away before a boat can come back.

The dock is the piece buyers most often misunderstand, and in Windward Shores it decides which of two very different products a house is. A private dock on Westlake Lake is not deeded to the lot; it is a permit issued by WLMA to a lakefront member, one per lot, and the rules are explicit that it transfers with the property on sale only if the seller is in good standing, meaning not more than 30 days delinquent on fees, carrying the required insurance and in compliance with any hearing decisions. Dock permits cannot otherwise be assigned without WLMA’s written consent, repairs and changes need prior approval, and the seawall along the shore is WLMA’s to maintain rather than the owner’s. A buyer’s agent on a lakefront Windward Shores lot should be ordering the WLMA good-standing letter and the dock permit file alongside the association documents, and hiring a dock contractor for a separate inspection, because a home inspector will not touch it.

Greenbelt homes have their own arrangement. Under the 2026 rules, members without a private dock may register one watercraft at a district community dock on a first-come basis, subject to restrictions near greenbelts, so a Windward Shores owner on the inner side of the loop can still keep an electric boat or kayak on the lake without owning frontage. That is the practical reason the greenbelt lots carry a lake assessment at all, and why a buyer comparing a $1.5 million greenbelt home with a $3 million lakefront one is comparing two ways of using the same water rather than water against no water. Tenants can be given temporary exclusive use of a private dock under a written agreement with the owner, provided they register and insure the boat, and the owner remains responsible for their conduct on the lake.

One level on the water. Westlake Village has thousands of single-story homes and a few hundred lakefront ones, and Windward Shores is where the two sets overlap most completely. A buyer who wants to walk from the front door to the dock without a stair anywhere in the house has very few places to look in the Conejo Valley, and this tract is the largest of them.

A private dock and the electric-boat lake. WLMA’s rules cap boats at 18 feet and require electric power, so the western arm behind Windward Shores is quiet enough to hear a heron land. An evening out means untying the boat, idling under the island bridge and tying up at The Landing for two hours, and no car is involved.

The right size. At 1,600 to 2,400 square feet on 5,000-square-foot lots, these are houses that a couple can maintain, heat, cool and clean without help, with a yard that is mostly patio and water. Downsizers from the larger hillside tracts describe the change as trading a house that owned them for one they own.

A small, private, through-traffic-free enclave without a gate to manage. Three circles, 92 homes and no reason for anyone else to drive in give Windward Shores much of the seclusion of Westlake Island without the guard house, the bridge or the island association’s budget.

Ventura County schools and services. For families who have chosen Conejo Valley Unified, Windward Shores is the lakefront option inside that district, with Westlake Elementary a mile away and the City of Thousand Oaks handling permits, streets and services.

The greenbelt alternative. A buyer who wants the lake lifestyle at half the price can buy a greenbelt lot, walk to the water and register a boat at a community dock. Few lake tracts offer a lower rung on the ladder that still comes with the same association, the same badges and the same view of the same water.

Every Windward Shores owner pays two associations, and recent listings report them in a consistent way. The first is the neighborhood association, shown on 2026 MLS listings simply as “Windward Shores,” with dues of $300 to $325 per quarter, about $100 to $108 a month. Those same listings pair the association name with “Seabreeze,” which appears to refer to Seabreeze Management Company, a large California association manager headquartered at 26840 Aliso Viejo Parkway in Aliso Viejo, reachable at 800-232-7517; that identification is Gary’s reading of the listing data rather than a confirmed fact, and buyers should verify the current manager and the association’s legal name from the escrow disclosure package. What the neighborhood dues cover is not itemized in the listings. Given the tract’s size and layout, the obvious items are the greenbelt that runs between the inner lots and the lake, common landscaping and insurance, and architectural review; there is no gate, no clubhouse and no pool, which is why the dues are a fraction of what the amenity-rich associations in Village Homes or Lakeshore charge.

The second association is the Westlake Lake Management Association, and here the listings show two different numbers for two different kinds of lot. A lakefront home with a dock on Leeward Circle reported the lake assessment at about $2,000 a year, and so did the original-condition lakefront listing on the same street in 2026; a greenbelt home on Leeward with lake access but no dock reported about $1,000 a year. Earlier research from 2010s listings put the combined cost at about $432 per quarter plus about $1,690 a year, which suggests both associations have restated their assessments over the years. The safest summary is that a lakefront Windward Shores owner should budget on the order of $3,200 to $3,300 a year for both associations and a greenbelt owner roughly $2,200, before WLMA’s separate charges for annual lake-use badges, fishing badges and boat registration, and that the only reliable figures are the ones in the current budgets. Buyers should ask for both associations’ budgets, reserve studies and any special assessment history; WLMA is the owner of a 700-foot concrete dam and a 125-acre lake, and its long-term capital needs are a legitimate question.

Architectural review runs on two tracks. The neighborhood association reviews exterior changes to the house, and WLMA must approve in writing anything at or over the water, including dock repairs, patio structures near the shore and lighting, because shoreline work happens under the lake association’s agreements with the state. Rental rules for the neighborhood association are not published; the WLMA side of leasing is described in the leasing section below. Mello-Roos does not typically appear on 1970s Westlake Village tracts, and the 2024 property tax bill of about $4,137 reported for one long-held Leeward Circle home, on an assessed value of about $244,652, is consistent with a standard Ventura County levy plus modest direct assessments, but the direct assessments on any specific parcel should be read from the tax bill. Building permits and code questions go to the City of Thousand Oaks, not the City of Westlake Village.

Windward Shores is on the Ventura County side of the county line, in the City of Thousand Oaks, and therefore in the Conejo Valley Unified School District. The three 2026 listings in the tract all show the same assignment: Westlake Elementary School for kindergarten through fifth grade, Colina Middle School for sixth through eighth, and Westlake High School. Westlake Elementary, at 1571 East Potrero Road inside the Foxmoor tract across Westlake Boulevard, enrolled about 505 students in 2025–26; it is roughly a mile from Windward Shores by road. Colina Middle School is off Hillcrest Drive and Westlake High School is on Lakeview Canyon Road, both a few minutes away by car. Some older neighborhood descriptions for this part of Westlake Village mention Westlake Hills Elementary instead of Westlake Elementary; the current listing data points to Westlake Elementary, but attendance boundaries change and the district, not a listing or this guide, is the authority. Gary confirms the assignment by parcel on every transaction.

The contrast with the other side of the lake is worth understanding, because it changes what a buyer is comparing. The Los Angeles County streets of Westlake Island, a few hundred feet east across the bridge, are in the Las Virgenes Unified School District and feed White Oak Elementary, Lindero Canyon Middle School and Agoura High School. Two families on the same lake, in houses of the same era, can be zoned to different high schools, and buyers who have already decided on a district should filter their search by the county line before they filter by the water. Private options nearby include Oaks Christian School on La Tienda Drive north of the 101 and Carden Conejo, an independent elementary school on Evenstar Avenue in Village Homes.

The lake is the park. Windward Shores residents boat, kayak and fish from their own docks or from the district community docks, walk the greenbelt to the water, and watch the lake’s calendar of events, including the Fourth of July fireworks and the holiday boat parade, from their own patios. The Westlake Yacht Club, based at The Landing on the north shore, teaches sailing to all ages and runs the patrol boat. The loop of Triunfo Canyon Road, Westlake Boulevard and the streets around the lake is a well-used walking and cycling circuit, and the WLMA office on Triunfo Canyon Road is close enough to visit on foot for a badge.

On land, the nearest public park is Triunfo Community Park at 980 Aranmoor Avenue, a Conejo Recreation and Park District facility on the far side of Westlake Boulevard in Village Homes. It has a baseball field, a softball field, two soccer fields, three lighted tennis courts on a first-come basis, a lighted basketball court, a sand volleyball court, ten picnic tables, restrooms, 92 parking stalls and a playground rebuilt in 2022 with natural play structures, and it is open daily from 7 a.m. to 10 p.m. The park is also the trailhead for the Triunfo Canyon Trail, which climbs into the Los Robles trail system in the Conejo open space, the most direct route from the lake into the hills for a morning hike or mountain-bike ride. Evenstar Park, four acres of turf and playground on Evenstar Avenue, is a little farther into Village Homes. On the Los Angeles County side of the line, Berniece Bennett Park at 31800 Village Center Road and the Westlake Village Community Park are a few minutes away by car.

Dinner and errands orbit the lake. The Landing at 32129 Lindero Canyon Road, with lakefront restaurants, a boardwalk and guest docks, is reachable by electric boat from a Windward Shores dock as well as by car, and the listing for 2398 Leeward Circle sold the idea of “dinner by boat at The Landing or Boccaccio’s,” the long-standing lakeside restaurant on the same shore. The Westlake Plaza and Village centers along Agoura Road and Westlake Boulevard are the nearest shopping, and the larger centers north of the freeway are described in the getting-around section below.

Every trip out of Windward Shores starts at Triunfo Canyon Road on the south shore of the lake. From there the choice is Westlake Boulevard, which is State Route 23 and meets US 101 about a mile north of the lake, or Lindero Canyon Road, reached by Agoura Road, with its own interchange a little to the east. Off-peak either on-ramp is roughly five minutes away; Westlake Boulevard is the busier because it carries the shopping-center traffic on both sides of the freeway, so residents heading east toward Agoura Hills or Calabasas often prefer Lindero Canyon, and Hampshire Road, one interchange west, is the alternate when Westlake Boulevard backs up. The 101 itself is the constraint. The Ventura Freeway between Westlake Village and the San Fernando Valley slows badly in both directions at commute hours, and a resident working in the Valley or downtown Los Angeles should plan on an hour or more each way at peak against perhaps forty-five minutes to the west Valley off-peak. Those are rough ranges, not measurements.

Errands are close. Gelson’s Westlake Village is at 2734 Townsgate Road just north of the freeway; Trader Joe’s is at 3835 East Thousand Oaks Boulevard and Ralphs is in the North Ranch Mall at 3963 East Thousand Oaks Boulevard, both a short drive up Westlake Boulevard and a turn onto Thousand Oaks Boulevard. The Promenade at Westlake, with its cinema, restaurants and grocery, sits at Westlake Boulevard and Thousand Oaks Boulevard on the north side of the 101, five to ten minutes away off-peak. The Landing on Lindero Canyon Road is a few minutes by car around the lake and about the same by electric boat from a dock on the western arm, passing under the island bridge on the way. The Oaks mall in Thousand Oaks, off the 101 at Hillcrest Drive, is a ten-to-fifteen-minute drive off-peak, and the medical and professional offices along Lindero Canyon Road and Townsgate Road are within the same radius.

The school run is short and stays on the Ventura County side. Westlake Elementary is across Westlake Boulevard inside Foxmoor at 1571 East Potrero Road, close enough that some families walk or bike and most drive in a few minutes; Colina Middle School off Hillcrest Drive and Westlake High School on Lakeview Canyon Road are each a few miles. Public transit is thin, as it is throughout the Conejo Valley. Metrolink’s Ventura County Line stops at Moorpark and Simi Valley, each roughly twenty to thirty minutes away by car off-peak, with no station in Thousand Oaks or Westlake Village; LADOT’s Commuter Express routes run weekday peak-hour buses between Thousand Oaks and Agoura Hills and the Valley, Hollywood and downtown Los Angeles, and Thousand Oaks Transit and Ventura County buses cover local routes along the 101, with schedules that change and should be checked. The coast is the neighborhood’s other geographic advantage. Westlake Boulevard continues south as State Route 23 past Potrero Road and becomes Decker Canyon Road, a steep and winding two-lane route to Pacific Coast Highway in western Malibu; Kanan Road from Agoura Hills is the wider way down Kanan Dume Road to Zuma Beach. Either is on the order of thirty to forty-five minutes to the sand off-peak, longer on summer weekends.

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.

Windward Shores prices are a story about two kinds of lot. In the two years through September 2026, two homes in the tract sold through the MLS, for $3,275,000 in November 2024 and $2,676,919 in March 2025; the 2026 Leeward Circle closings below do not appear in that MLS data. Against a median home of about 1,960 square feet, the middle of the market works out to roughly $1,100 per square foot, in the same territory as Westlake Island and well above the $550 to $750 per foot that prevails in the land-locked tracts on the same side of the county line. The bottom of the range is the greenbelt homes, the top is renovated lakefront homes with docks, and the gap between them is the water.

The 2026 closings show the spread inside one street. At 2398 Leeward Circle, a 1976 single-story of 2,263 square feet with three bedrooms and three baths, fully renovated with a Thermador kitchen, a reworked primary bath and a private dock, was listed in February 2026 at $3,200,000, reduced to $3,099,000 in March, and closed on April 27, 2026 at $3,110,000, about $1,374 per square foot, after 70 days on the market. The same house had sold on February 27, 2025 for $2,340,000, so the intervening renovation and a strong lakefront market added roughly $770,000 in fourteen months. At 2362 Leeward Circle, a 1,609-square-foot two-bedroom, two-bath home of the same year on a 5,227-square-foot greenbelt lot, thoroughly updated with a 2018 lightweight tile roof, newer dual-pane windows, a newer electrical panel, updated plumbing, newer heating and cooling and a tankless water heater, was listed in March 2026 at $1,650,000, reduced to $1,579,000, and closed on June 16, 2026 at $1,500,000, about $932 per square foot, after 99 days. Its listing history shows it at $640,000 in 2013 and $979,000 in 2016. Between the two, 2378 Leeward Circle, an original-condition 1,808-square-foot lakefront home with three bedrooms and two baths on a 6,219-square-foot lot, came to market for the first time on August 7, 2026 at $2,100,000, about $1,162 per square foot, and went pending within the month; it is the clearest current measure of what an unrenovated lakefront lot is worth on its own.

Turnover is low: two MLS sales in the last two years across 92 parcels is about one percent a year, which fits a neighborhood of one-story homes bought by owners at a later stage of life. Because the tract is small and the lakefront lots are a subset of it, a buyer who wants a dock and a specific view may see only one or two suitable homes in a year, and the 2026 pattern of list-price reductions followed by sales a few percent under the reduced price suggests sellers have been pricing a little ahead of the market. Long-held homes are also common; the 2024 property tax on 2378 Leeward Circle, about $4,137 on an assessed value of about $244,652, reflects an original-owner Proposition 13 basis, and a buyer at $2.1 million should expect a tax bill roughly ten times that amount once the parcel is reassessed.

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.

Windward Shores has a rental market, and it is a very small one. In a September 2026 scan of public rental listings for Westlake Village, one house in the tract was advertised, a three-bedroom, two-bath home at 2350 Leeward Circle listed on Redfin, and none appeared on the other major rental sites. Against 92 parcels that suggests one or two homes for lease at any moment and perhaps a handful of leases in a typical year; most owners live in their houses, and the ones who leave tend to sell. The asking rent for the Leeward Circle home was not captured in Gary’s review, so the working ranges below come from comparable homes around the lake and on the same side of the county line, and should be treated as estimates.

The nearest comparables are on Westlake Island, where September 2026 asking rents for single-story and small two-story homes of the same era ran from $7,200 a month for a 1,592-square-foot two-bedroom on Mainsail Circle to $8,900 for a 2,954-square-foot five-bedroom on the same street, roughly $3 to $4.50 per square foot with the lake and the dock driving the number. On the Ventura County side without water, 1970s houses of 1,700 to 2,500 square feet in Village Homes and Foxmoor were asking about $5,800 to $7,200 a month in the same month, for example $5,795 for a 2,491-square-foot four-bedroom on Triunfo Canyon Road, $6,450 for a 1,737-square-foot four-bedroom on Bainbrook Court, and $7,200 for an 1,895-square-foot four-bedroom on Kingspark Court. A Windward Shores greenbelt home should therefore lease roughly in line with the Village Homes range, about $5,500 to $7,000 a month depending on condition, and a lakefront home with a dock closer to the island range, about $7,000 to $8,500, with a furnished lakefront home commanding more. Gary Jacobs leased 3808 Mainsail Circle on Westlake Island, a 1,568-square-foot 1973 home, in January 2010 for $2,725 a month, and the same size of house on the same street was asking $7,200 in 2026, which is the clearest measure of how far lakefront rents in Westlake Village have moved in sixteen years.

The lake rules follow the tenant. WLMA requires a member who leases a home to give the tenant a copy of the rules and holds the owner responsible for the tenant’s conduct on the water. A residing tenant can be given temporary exclusive use of the private dock under a written arrangement with the owner, provided the tenant owns or leases the boat under a written agreement and keeps its registration and insurance current, and lessees can obtain annual fishing badges. Because the dock is a WLMA permit issued to the owner rather than a right that comes with the lease, a Windward Shores rental agreement should say plainly whether the tenant may use the dock, whose boat may be tied there and who carries the insurance. The neighborhood association’s own leasing policy, including any minimum term, is not published, and a buyer planning to rent the home out should ask before closing. Under the state security-deposit law in effect since July 2024, a small landlord can ask up to two months’ rent and a larger one only one month. Tenants who lease here tend to be executives relocating to Amgen and the employers along the 101 corridor, households waiting out a rebuild elsewhere in Westlake Village, and retirees testing single-story lake living before buying it.

The Windward Shores homes were built in 1973 and 1976, and an unrenovated example carries the systems of that era. What follows is common in Westlake Village homes of this age; every house varies, and only a licensed inspector looking at the specific property can say what applies. By the mid-1970s copper water supply was standard in Conejo Valley tracts, so galvanized steel lines are less likely here than in the 1960s neighborhoods across the lake, but original copper is now fifty years old and pinhole leaks and a repipe to PEX are common line items in remodeled listings. Drain lines of the period are cast iron under the slab and ABS above it, and a camera inspection of the sewer lateral is worth the cost on a house that sits on graded fill beside a lake, since settlement can put a belly in the line. Homes finished in 1976 fall just before the years when polybutylene supply pipe became common, but it is worth a glance.

Electrical panels deserve a direct question. Zinsco and Federal Pacific Stab-Lok panels were installed across the Conejo Valley through the 1970s, many inspectors and insurers now treat both as replacement items, and some carriers ask about the panel brand on the application; the remodeled greenbelt home that closed in June 2026 advertised a “newer electrical panel” for that reason. Aluminum branch wiring, which turns up in some homes built nationally between the mid-1960s and about 1973, could overlap with the Windward Circle phase and is very unlikely in the 1976 phase; the usual remedy is a certified connector retrofit at every device rather than a rewire. Original aluminum-frame single-pane sliders, which on a lakefront plan can run the whole water side of the house, show up on nearly every unrenovated inspection, both for energy loss and for corroded rollers and failed seals in the damp air off the lake. Original roofs of shake or tar-and-gravel have generally been replaced once or twice; the heating and cooling equipment and ducting are usually in the attic and often on their second or third generation; and tract-era attic insulation is thin. Vaulted ceilings, which the plans use throughout, mean less attic to work in and less room for ducts.

The lake adds its own list. Every lot in the tract sits on graded ground a few feet above lake level, so inspectors look for slab moisture and efflorescence on the water side, cracked patio hardscape that suggests differential settlement, drainage that carries water away from the foundation rather than pooling behind the seawall, and corrosion at anything metal near the water. The seawall is WLMA’s responsibility, so the useful question is what the association’s records show for that stretch of shore. The dock is the owner’s, is outside the scope of a home inspection, and should be checked separately by a dock contractor for rot, corroded fasteners, flotation, electrical service to the dock and boat charger, and whether the structure matches the permit on file with WLMA. Patio covers, enclosed atriums and extensions toward the water are the most common unpermitted improvements in single-story lake tracts, and permit history comes from the City of Thousand Oaks.

The remodel arithmetic in Windward Shores is simpler than on Westlake Island because the houses are all the same shape. The 2026 record on Leeward Circle is the cleanest local example: a 2,263-square-foot lakefront plan bought in February 2025 for $2,340,000 and resold in April 2026, fully renovated, for $3,110,000. Some of that $770,000 is market movement and some is the renovation, but the renovation was the thing buyers paid $1,374 per square foot for, against roughly $1,162 per foot for the original-condition lakefront home listed on the same street five months later. On the greenbelt side, the 1,609-square-foot home that closed at $1,500,000 in June 2026 was sold on its systems as much as its finishes, with a 2018 roof, newer windows, panel, plumbing, heating and water heater all listed, and it still traded at about $932 per foot. The lesson, hedged for a small sample, is that renovation pays here at both price points, and that in a one-story tract where buyers are often downsizing, the systems and the absence of steps are worth as much as the kitchen.

The projects that recur in listings follow from the plans on file. The kitchen, breakfast area and family room are separate rooms in the original drawings, and opening them into one water-side great room with wide sliders or a folding door to the patio is the standard first move. The atrium off the dining room is usually either glassed in to add square footage or landscaped as a true courtyard with a water feature; both approaches appear in the tract. Primary baths get enlarged into the adjacent closet or bedroom, and the “spa-inspired” bath in the April 2026 sale is the current benchmark. Vaulted ceilings are already there, so the work is more about light and flow than volume. Because the lots are about 5,200 square feet and the house already fills much of the buildable envelope, additions tend to be modest, a few hundred square feet toward the side yard or a covered outdoor room on the water, and the one full rebuild recorded in 2010 at about 4,500 square feet shows the ceiling of what the association and the city have approved; a buyer contemplating a second story should assume both associations will scrutinize height, and neighbors will care about their view across the arm.

Accessory dwelling units are a limited opportunity. State law now requires cities to approve an ADU of at least 800 square feet with four-foot side and rear setbacks on nearly any single-family lot, allows a junior ADU of up to about 500 square feet within the existing house, and prevents associations from prohibiting them outright, though reasonable conditions are allowed and the current rules should be confirmed with the association and the City of Thousand Oaks. On a Windward Shores lot the back yard is the lake or the greenbelt, so a detached unit is rarely worth the trade; a garage conversion or a junior unit carved from a bedroom with its own entrance is the realistic form, and it suits a caregiver or an adult child more than a separate tenant.

The lots are small and the houses fill them. A Windward Shores lot is about 5,200 square feet at the median and as little as 3,500 on Windward Circle, and the back yard is a patio and a seawall. Buyers who want lawn, a pool or a detached studio should look at the hillside tracts instead. The one-story plans also cap out around 2,400 square feet in original form, and adding a second story is possible but subject to two associations, the city and neighbors who value their view across the narrow western arm.

The water costs money in ways beyond the price. Lakefront owners pay about $2,000 a year to WLMA on top of the neighborhood dues, plus badges, boat registration and the eventual replacement of a dock that a home inspection does not cover. Insurance carriers ask about panel brands and proximity to water. A buyer of a $2 million to $3 million home should budget for the reassessed tax bill, which can be ten times what a long-held original owner was paying.

Two associations mean two sets of rules and two escrow packages. WLMA controls the dock, the seawall and everything at the water; the neighborhood association controls the house. Escrows on lakefront property around Westlake Lake commonly run into document-review extensions, and having both associations’ paperwork in hand before an offer is written is the practical remedy.

The systems are fifty years old unless someone has replaced them. The tract has a good share of renovated homes, but the original-condition lakefront listing of 2026 is a reminder that first-time-on-the-market homes still exist here, and a buyer of one should price in a repipe, a panel, windows, heating and cooling, and a roof if not already done.

The western arm is not the main lake. Views are across a narrower body of water toward Westshore or the flank of the island, pleasant and private but not the wide-open panorama of the island’s outer edge or the east shore. Boat traffic to and from The Landing passes the back yard on summer evenings, which most owners enjoy and a few do not.

The county line. Windward Shores is in Thousand Oaks and Conejo Valley Unified, not the City of Westlake Village and Las Virgenes Unified, despite the mailing address. Buyers who assumed the lake was all one jurisdiction sometimes discover the difference late; it is neither better nor worse, but it is different, and it should be settled before an offer rather than after.

Downsizers from the hillside tracts are the core buyer. A couple leaving a 3,500-square-foot two-story in Three Springs, North Ranch or Foxmoor Hills, often after the children have gone, wants one level, a smaller footprint and something to look at, and Windward Shores gives them all three with a dock thrown in. Many arrive with the equity to pay cash for a renovated lakefront home in the $2.5 million to $3.5 million range and the patience to wait a year for the right one.

Lake-lifestyle buyers who priced Westlake Island and stepped back are the second group. The island’s median is above $3 million and its combined assessments are higher; a Windward Shores lakefront home offers the same lake, the same electric boat and the same trip to The Landing at a lower entry price, without a gate to pass through, and the Ventura County schools instead of the Los Angeles County ones, which for some families is the deciding factor.

Families targeting Conejo Valley Unified with a lake in mind are a smaller third group, drawn by Westlake Elementary a mile away and by the three-bedroom plans, which work for a family with one or two children. The small lots and the open water behind the house make the tract less common for families with very young children than Foxmoor or Village Homes.

Greenbelt buyers are their own category: households who want to be part of the lake community, walk to the water and keep a kayak or a small electric boat at a community dock, at half the price of frontage. The June 2026 sale of a two-bedroom greenbelt home for $1.5 million, to a buyer who valued its systems and its single level, is the template. A few of these buyers are also renters trying the lake first, and a few are investors, though the tract’s thin rental market keeps that number small.

The obvious comparison is Westlake Island, a few hundred feet away across the water and reached by the La Venta Drive bridge that Windward Shores residents pass on the way home. The island has about 446 parcels, every one of them waterfront, built from 1967 to 1981 with a median home of about 2,700 square feet on a median lot of about 5,360, guarded around the clock at a single gate, and it has renewed itself with second stories and full rebuilds to the point that homes over 3,500 square feet are common. Its 2024–2026 sales ran from about $1.45 million to $8 million with a median near $3.05 million, roughly $1,000 to $1,200 per square foot for typical closings, and its owners pay both an island association and WLMA, with combined assessments that have run on the order of $3,500 to $6,500 a year. Windward Shores is the one-story, ungated, smaller-scale version on the mainland: 92 homes with a median of about 1,960 square feet, recent MLS sales of about $2.68 million to $3.28 million, comparable per-foot pricing on the lakefront lots and a much lower entry point on the greenbelt lots, and combined dues of roughly $2,200 to $3,300 a year. The island’s Ventura County streets, Bluesail, Redsail, Eastwind, Southwind, Westwind and the 2400 to 2660 block of Oakshore Drive, share Windward Shores’ school assignment; its Los Angeles County streets do not.

On the north and east shores, Lakeshore and Northshore are the attached alternatives. Lakeshore, on the Los Angeles County side off Triunfo Canyon Road and Lakeview Canyon Road, is about 278 townhomes and patio homes built in 1967 to 1969 as the lake was being filled, 1,300 to 2,250 square feet on lots of about 3,000, with three pools, private beaches and docks for dues of roughly $275 to $310 a month; its 2024–2026 sales ran from about $520,000 to $2.46 million with a median near $1.35 million, and it feeds Las Virgenes Unified. Northshore, on the Ventura County side north of the island, is about 240 attached planned-unit homes from 1973, mostly 1,144 to 1,765 square feet, with a clubhouse, pool, spa and a private beach on the lake for dues in the neighborhood of $364 a month, and a 2024–2026 median close to $1.13 million with sales from about $600,000 to $2.5 million; it shares Windward Shores’ schools. Both offer the lake at a lower price with shared walls and shared amenities; Windward Shores offers detached one-story homes with private docks and much lower dues, at a higher price.

Inland on the same side of the county line, Foxmoor and Village Homes are what a Windward Shores buyer gives up the water to get. Foxmoor, built in 1968 and 1969 around Westlake Elementary just across Westlake Boulevard, has about 270 homes with a median near 2,460 square feet on lots near 6,970, a pool, clubhouse and greenbelt for about $230 to $240 per quarter, and 2024–2026 closings from about $1.14 million to $2.7 million with a median of about $1.55 million, roughly $600 to $650 per square foot. Village Homes, along Triunfo Canyon Road and around Triunfo Community Park, went up in phases from 1969 to 1978, so its later homes match the age of Windward Shores; it has about 622 homes with a median near 2,200 square feet on lots near 7,400, a pool, spa, clubhouse, tennis and a long greenbelt for about $260 to $275 per quarter, and a 2024–2026 median close to $1.46 million at roughly $550 to $750 per foot. Both feed Westlake Elementary, Colina Middle and Westlake High, the same assignment as Windward Shores, and both have more single-story homes than most Westlake Village tracts. A buyer who wants one level and Conejo Valley Unified can therefore choose between a lake and a dock at about $1,100 per foot in Windward Shores, or a larger lot, a pool and tennis courts at about $600 per foot a few blocks away.

Put together, Windward Shores trades at Westlake Island prices on its lakefront lots and at hillside-tract prices on its greenbelt lots, with the lowest combined dues of any lake neighborhood on the Ventura County side and none of the shared walls of Lakeshore or Northshore. What it lacks is scale, amenities and large lots; what it has, that almost nothing else around the lake has, is a detached one-story house with its own dock. The broader context is on the Westlake Village guide.

Gary Jacobs has no recorded sale or lease inside Windward Shores itself, and says so plainly; with 92 homes and a handful of sales a year, most Conejo Valley agents can say the same. His work around the lake and on the same side of the county line is the relevant record. On Westlake Island, a few hundred feet away, he leased 3808 Mainsail Circle, a 1,568-square-foot single-story from 1973 that is a close cousin of the Windward Shores plans, in January 2010 for $2,725 a month, and he has represented buyers and sellers of island homes since. In Lakeshore, on the opposite shore, he sold 32108 Beachview Lane, a three-bedroom, 1,753-square-foot 1968 lake home, in February 2018 for $690,000. In Foxmoor, across Westlake Boulevard, he sold 1490 Cheswick Place, a 2,494-square-foot 1971 two-story with a pool, in January 2018 for $970,000, and in Village Homes he sold 2244 Silver Spring Drive, a 3,128-square-foot two-story with pool and spa, in January 2017 for $1,052,500 after leasing it four times between 2008 and 2013, and leased 1869 Tamarack Street, a 4,600-square-foot 2009 home, in October 2022 at $9,000 a month.

For Windward Shores specifically, Gary keeps the five original tract 733 plan sheets, the parcel-by-parcel build dates and lot sizes for Topsail, Leeward and Windward Circles, the 2024–2026 closing record for the tract, and the current WLMA rules and fee schedule. He will provide a comp set for any Windward Shores home, lakefront or greenbelt, on request.

Buyers: decide first whether the purchase is lakefront or greenbelt, because they are different products at different prices with different lake assessments, and write the offer accordingly. On a lakefront lot, order the WLMA good-standing letter, the dock permit file and any seawall records at the same time as the neighborhood association’s documents, and book a dock contractor alongside the home inspector; on a greenbelt lot, ask WLMA about community-dock availability in the district before assuming a boat can be kept. Confirm the school assignment by parcel with Conejo Valley Unified, confirm that the City of Thousand Oaks is the permitting authority, pull the permit history for any enlarged or enclosed space, and read the tax bill for direct assessments. Budget for reassessment; the seller’s tax bill on a long-held home is not a guide. Expect little inventory: a specific lakefront position may appear once a year, and a pre-approved buyer with the association paperwork already read is the one who gets it.

Sellers: the 2026 closings show that renovated homes on both sides of the loop sold at a premium and that original-condition lakefront homes still draw immediate attention, so the decision is whether to sell the house as an opportunity or as a finished product; both work, but they should be priced differently. Have the WLMA good-standing letter, the dock permit, the association budgets and a current dock inspection in the disclosure package before listing, because dock and document questions are the usual cause of extended escrows on this lake. Photograph from the water and at the hour the light comes across the arm from the west. Lead the marketing with what is scarce, a detached single-story home with its own dock, rather than with finishes, and price against the current Windward Shores and Westlake Island closings rather than against the inland tracts.