Kent

Lakeside Woods, Kent Neighborhood

Lakeside Woods offers a peaceful and tranquil environment with quiet streets that promote relaxation. The neighborhood predominantly features single detached homes built from the 1960s to the 2000s, providing diverse options ranging from lofts to spacious four-bedroom residences. Parking is convenient throughout the community, making transportation by car straightforward and practical. While cycling presents some challenges due to the area's terrain and limited bike paths, many residents still make use of bicycles. Shops and dining options are accessible, though traveling by vehicle is the most practical choice for errands. Overall, Lakeside Woods presents a serene setting with a variety of housing choices.

The character of Lakeside Woods is exemplified by its calm environment. Lakeside Woods is very quiet, as there isn't a lot of street noise or city clamor.

Highlights of Lakeside Woods

Parks, schools, dining, and what makes this neighborhood special

🌊 Candlewood Lake Shoreline

Sitting directly on the western shore of Candlewood Lake, Lakeside Woods provides residents with easy access to boating, swimming, and scenic shoreline views that anchor the neighborhood’s lakeside charm.

🏫 Sherman School (K–8)

Located just north in Sherman, this well-regarded K–8 public school serves neighborhood families, offering a personalized and supportive learning environment before students attend one of several nearby high schools.

🚤 Orchard Rest Community Dock

Homes within Lakeside Woods like those on Chestnut Hill Road include access to a shared community beach and boat dock with designated slips on Candlewood Lake, enhancing waterfront living opportunities.

🥾 Historic Trail Maps & Exploration

The neighborhood is surrounded by old trail networks—vintage USGS maps show footpaths, ghost roads, and exploration routes that adventurers and history enthusiasts can rediscover over layered terrain.

🏞️ Proximity to Hiking & Lakeside Trails

Though small, Lakeside Woods is a gateway to outdoor recreation with nearby trails around Sherman and western Candlewood Lake area offering peaceful hiking, lakeside walks, and pastoral landscape experiences.

A Kent Neighborhood

This August in Lakeside Woods

Things to do, events, and what's happening this month

August 6–9, 2026

Kent Sidewalk Sale Days

Main Street, Kent, CT

This beloved summer tradition brings Main Street in Kent to life with pop‑up shops, discounts, live music, food, and family activities—perfect for Lakeside Woods residents looking to support local businesses and enjoy a festive community vibe just minutes away.

August 15, 2026

Kent Farmers’ Market

Town Hall Park, Kent Lakes, NY • 10:00 AM–2:00 PM

A convenient weekend farmers’ market offering fresh local produce, crafts, and friendly community atmosphere—ideal for Lakeside Woods residents seeking nearby, seasonal shopping and a chance to mingle with neighbors.

August 3–31, 2026

Mystery Take and Make! (Kent Public Library)

Kent Public Library

A summer-long mystery craft program where families pick up surprise take‑home kits—great for Lakeside Woods families looking for creative, low‑effort activities close to home all month long.

August 5, 2026

Starry Night Stuffed Animal Sleepover (Kent Public Library)

Kent Public Library • 5:30 PM–6:15 PM

A playful, whimsical program where children bring a stuffed animal for a sleepover storytime—a charming, local option for young families seeking gentle evening entertainment near Lakeside Woods.

August 17–19, 2026

Family Camp Mini Weekend (Club Getaway)

Club Getaway, 59 S Kent Road, Kent, CT

A lakeside family camp weekend offering outdoor adventure and connection—an excellent getaway for Lakeside Woods families wanting a nearby immersive outdoor experience without a long trip.

From the Neighborhood

Stories, updates, and things to know in Lakeside Woods

Know Your Neighborhood

Local characteristics and demographics for Lakeside Woods

Neighborhood Characteristics

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Demographics

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