Cottage living in the heart of Wellesley. Welcome to 20 David Street, a rare & beautifully updated waterfront home overlooking Wellesley Pond. Professionally & extensively renovated in 2021, this 3 bedrm+den, 3-bathrm home offers approx. 2,133 SF of finished living space, blending modern comfort with a pond-side setting that feels like a private retreat in town. The main flr is bright, open, & designed to bring the view into everyday living, with a spacious family rm featuring an electric fireplace, dining area, & updated kitchen. Glass sliders lead to the oversized back deck, creating seamless indoor-outdoor living. With glass railings & a pergola, the deck captures the pond views beautifully & offers space for morning coffee, summer dinners, quiet evenings, & relaxed entertaining. The updated kitchen features quartz counters, stainless appliances, tile backsplash, under-cabinet lighting, & breakfast bar seating for 4. Main flr laundry, a 2-pce bathrm, custom window coverings, designer lighting, & pot lights throughout add to the home’s polished feel. Upstairs, the luxurious primary suite is tucked into its own private wing with dual walk-in closets, an updated 3-pce ensuite with tiled glass shower, & direct access to a den/office-perfect for working from home, a nursery, reading rm, or quiet escape. 2 additional spacious bedrms & an updated 4-pce main bathrm complete the upper level. Outside, the property comes to life with a covered front porch, partially fenced & beautifully landscaped backyard, mature trees, walk-down access to the private dock & pond, & a tranquil, cottage-like feel that is hard to replicate. Approximately $30K in additional recent improvements further enhance the home’s privacy, curb appeal, & move-in ready feel. Walkable to local shops, groceries, parks, community events & amenities, with easy access to Waterloo, Kitchener & Stratford, this is more than a move-in ready home-it's a rare waterfront lifestyle property in the heart of Wellesley.