33 S Windsor Avenue

A distinguished 1925 French Provincial residence on one of Brightwaters most prestigious blocks features 5 bedrooms, 3.5 bathrooms and over 3,700 square feet of architectural living. Fully restored and renovated in 2026 just steps away from the water and the entrance to Gilbert Park. Set into .41 acres, this standout property welcomes you with timeless curb appeal highlighted by steeply pitched roof lines and asymmetrical massing, a hallmark of French Provincial architecture that is complimented by a charming, crushed stone driveway and detached two-car garage. A spacious European sunroom entryway with 10-foot finished ceilings immerses you in the home’s impressive scale and historic character. Original Ebony Oak Hardwoods and decorative millwork remain thoughtfully preserved throughout the floor plan. The main living room anchored by a wood-burning fireplace is wrapped in European revival style windows and detailed stepped crown molding finish a great room with enduring architectural appeal. Arched openings create a welcoming transition into the formal dining room which offers an elegant setting for entertaining in the heart of the home. The chef’s kitchen features quartz countertops, a full stainless steel appliance suite, gas cooking, custom wet bar with wine refrigerator and built-in wine storage. Water views from the kitchen add a rare and serene backdrop. A first-floor laundry room and dedicated private office provide modern functionality without compromise. The residence offers a total of five bedrooms and three-and-a-half baths, including a primary suite with tranquil water views, a full wall of windows, a generously sized walk-in closet, and a spa-inspired bath with dual vanities. Three bedrooms and a full hallway bathroom with charm and original details finish the second level while the third floor hosts another private bedroom with wonderful water views and an ensuite bath. Additional highlights include natural gas heating, central air conditioning, public sewers, and a location that embodies the charm and walkability of Brightwaters Village. A rare offering combining historic provenance, modern refinement, and water-adjacent living, 33 S. Windsor Avenue represents a truly elevated Brightwaters lifestyle for the most discerning South Shore buyer.