Waterside Real Estate

Waterside Real Estate

Welcome to Waterside, an enchanting neighborhood nestled in the vibrant city of Stamford, Connecticut. Known for its picturesque waterfront views and a warm sense of community, Waterside offers a unique blend of suburban tranquility and urban convenience. This charming enclave is perfect for families, young professionals, and retirees alike, making it a sought-after destination in Fairfield County.

One of the standout features of Waterside is its proximity to the Long Island Sound, allowing residents to enjoy scenic walks along the waterfront and partake in various recreational activities. The neighborhood boasts beautiful parks, including the popular Cummings Park, where you can bask in the sun, picnic with friends, or take a leisurely stroll along the sandy beach. Waterside is also home to a vibrant marina, making it a haven for boating enthusiasts and water sports lovers.

In addition to its natural beauty, Waterside is conveniently located near Stamford’s bustling downtown area, which offers an array of shopping, dining, and entertainment options. From trendy cafes to fine dining restaurants, there’s something to satisfy every palate. The neighborhood is also well-connected to public transportation, with easy access to Metro-North trains, making commuting to New York City a breeze.

With its friendly atmosphere, stunning landscapes, and a wealth of amenities, Waterside truly embodies the best of coastal living in Connecticut. Discover the charm of this remarkable neighborhood and make it your next home sweet home!

Newest Listings in Waterside

38 Carlisle Pl, Stamford
$719,000
3 Beds ⋅ 2 Baths ⋅ 24209120 MLS
Welcome to 38 Carlisle Place, a charming 3-bedroom, 2-bath Cape offering an inviting blend of character, updates and versatility. Inside, enjoy hardwood floors, a beautifully updated eat-in kitchen with quartz countertops, a bright sunroom with French doors, and a full bath on each level. The expansive upper-level primary bedroom offers exciting potential for a future 4-bedroom layout. Outside, a newly improved backyard and beautiful new stonework create the perfect setting for entertaining and outdoor living. Additional highlights include a newer roof and boiler, attached garage, private driveway, and a large unfinished basement offering exceptional storage and future possibilities. Convenient to shopping, dining, parks and transportation.

38 Carlisle Pl, Stamford
604 Fairfield Ave, Stamford
$999,000
6 Beds ⋅ 2 Baths ⋅ 24192292 MLS
Outstanding value-add opportunity in Stamford! This spacious two-family property offers approximately 2,378 SF of currently recorded living area, with each unit presently laid out with 3 bedrooms, a living room and a dining room, providing significantly more functional space than the original configuration. What truly sets this property apart is its renovation potential. The seller has renovation plans and a building permit supporting improvements to both the basement and third-floor/attic areas. The basement has an approximately 1,181 SF footprint, with the permitted scope including 1 bedroom, 1 full bath and wet bar as an extension of the first-floor unit. The permit also provides for connection of the attic to the second floor for storage. With 2,378 SF of existing recorded living area plus substantial additional basement and attic/storage space, this property presents tremendous upside for investors, owner-occupants or buyers looking to renovate and maximize a multi-family asset. Located in an established Stamford residential neighborhood with convenient access to shopping, restaurants, transportation, downtown Stamford and major commuting routes. A rare opportunity to acquire a two-family property with existing space, renovation plans, permits and significant value-add potential. Buyer to perform due diligence regarding plans, permits, approvals & allowable sqft.

604 Fairfield Ave, Stamford
511 Fairfield Ave, Stamford
$975,000
6 Beds ⋅ 4 Baths ⋅ 24198263 MLS
ATTENTION INVESTORS AND/OR BUILDERS! OPPORTUNITIES ARE KNOCKING ON YOUR DOOR! COME SEE THIS MEGA 2-FAMILY HOME FEATURING 3,200 SQUARE FEET AND SITTING ON A MASSIVE .24 ACRE LOT WITH 2 DETACHED CAR GARAGE. WHETHER YOU CHOOSE TO RENOVATE OR TEAR DOWN THE EXISTING STRUCTURE TO BUILD FROM SCRATCH, THE OPPORTUNITY IS THERE. THE UNITS ARE SIDE BY SIDE. THE CURRENT LAYOUT IS 3 BEDROOMS, ONE FULL BATH AND A HALF IN EACH UNIT. THE LEFT UNIT FEATURES A PARTIALLY FINISHED BASEMENT. WASHER AND DRYER HOOKUPS ARE IN BOTH UNITS. EASY COMMUTE TO HIGHWAYS, TRAINS, BEACHES, SHOPPING CENTERS, RESTAURANTS, AND THE VIBRANT DOWNTOWN OF STAMFORD. VERY CONVENIENT LOCATION! FULL OF POTENTIAL! BRING YOUR BUYERS, INVESTORS, ENTREPRENEURS, ETC! HOUSE TO BE SOLD IN "AS IS" CONDITION.

511 Fairfield Ave, Stamford
19 Davenport St, Stamford
$899,500
9 Beds ⋅ 3 Baths ⋅ 24194303 MLS
Well-maintained property in Stamford's Waterside neighborhood, offering a compelling opportunity for owner-occupants and investors. Legal two-family, The basement is partially finished with a full bathroom, The first floor has two units with separate entrances: one offers 3 bedrooms, a full kitchen, a full bathroom, and a living room, while the other is a Studio-style unit with a kitchenette and full bathroom. The second floor is the largest unit, featuring 4 bedrooms, a full kitchen, a full bathroom, and a living room area. These property was remodeled with sheetrock, all plaster was removed. Flood insurance needed.

19 Davenport St, Stamford
281 Greenwich Ave, Stamford
$2,599,000
15 Beds ⋅ 15 Baths ⋅ 24148165 MLS
New Construction - Units are now completed with Certificate of Occupancy. rented at $3,500. each with leases beginning on July 1, 2025. Low maintenance 5 unit townhouses. Each unit has 3 bedrooms and 3 bathrooms. There are 12 parking spaces in all and washer/dryer in each unit. Attic storage. Alarm system with camera. All separate utilities. Walk to the Stamford Train Station and minutes to Stamford downtown and Harbor Point shopping, restaurants and bars. These units are perfect for a 1031 tax exchange.

281 Greenwich Ave, Stamford
281 Greenwich Ave, Stamford
$2,599,000
15 Baths ⋅ 24148010 MLS
New Construction - less than 1 year old. All 5 units (3BRs, 3 Baths each) are rented for $3,500/month each. Great project for an investor, nothing to do. Tenants are responsible for their own utilities. Washer/Dryer in all units plus attic storage. All separate utilities. Walk to Stamford Train Station and minutes to Stamford downtown and Harbor Point shopping, restaurants and bars. Complex was begun in 2024, but completed in 2025 These units are perfect for a 1031 Tax Exchange

281 Greenwich Ave, Stamford
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The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

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