West Side-Waterside-South End, CT homes for sale & real estate

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NEW 13 HRS AGO

255 Fairfield Ave, Stamford, CT 06902
255 Fairfield Ave, Stamford, CT 06902
255 Fairfield Ave, Stamford, CT 06902
ABOUT THIS HOME
West Side-Waterside-South End, CT Homes for Sale
Welcome to this rare and expansive 2-family residence offering a total of 9 generously sized bedrooms and multiple living spaces, perfectly designed for multigenerational living or rental income opportunities. Each unit features a private entrance and a thoughtfully designed layout to maximize space and comfort. Perfect for innovative living designs! A Yard to Enjoy and ideal for entertaining or relaxing outdoors and the property offers a partially finished basement that's ready for your vision! Don't miss this chance to own a versatile and income-producing property in a great location! Just 1 minute from Downtown, Harbor Point, The Train Station, Bus Station, and Hospital! TALK ABOUT LO

$899,000

9 beds3 baths3,364 sq ft

255 Fairfield Ave, Stamford, CT 06902

5,662 sq ft lot • 2 garage spots • 2 family residence

16 Carolina Rd, Stamford, CT 06902
16 Carolina Rd, Stamford, CT 06902
16 Carolina Rd, Stamford, CT 06902
ABOUT THIS HOME
West Side-Waterside-South End, CT Homes for Sale
Stamford Multi Family with two units, one upstairs and one down. Great opportunity for an investor, or live in one apartment and rent out the other, as this owner has for many years. Nicely set on a level 0.16 acre lot with ample private parking as well as a two car garage. First floor apartment features: Living room with fireplace, dining room, kitchen, sun room, 2 bedrooms and one full bath with Tub/shower. Second floor apartment features: Living room, kitchen with large dining area, sun room, 2 bedrooms and one full bath with Tub/shower. The basement is partially finished but is in need of repair. . Utilities: City water, city sewer. Two electric meters, one for each of the units. Basebo

$800,000

4 beds2 baths2,344 sq ft

16 Carolina Rd, Stamford, CT 06902

6,969 sq ft lot • 2 garage spots • Two separate units

115 Top Gallant Rd #6, Stamford, CT 06902
115 Top Gallant Rd #6, Stamford, CT 06902
115 Top Gallant Rd #6, Stamford, CT 06902
ABOUT THIS HOME
West Side-Waterside-South End, CT Homes for Sale
Welcome to 115 Top Gallant Road, Unit 6 - a beautifully maintained and thoughtfully updated townhome nestled adjacent to Stamford's Dolphin Cove and Southfield Point, with easy access to downtown and nearby Old Greenwich. This light-filled 2-bedroom, 1.5-bath home offers the perfect blend of charm, comfort, and convenience. Step inside to find soaring ceilings, a cozy gas fireplace, and an open layout ideal for both relaxing and entertaining. The versatile second floor bonus space is perfect as a home office, reading nook, or additional sitting area. The kitchen and dining room flow seamlessly out to your private backyard oasis, featuring a large expanded patio-perfect for outdoor dining or

$810,000

2 beds1.5 baths1,463 sq ft

115 Top Gallant Rd #6, Stamford, CT 06902

$400 HOA • Garage • Cozy gas fireplace

137 Wilson St #15, Stamford, CT 06902
137 Wilson St #15, Stamford, CT 06902
137 Wilson St #15, Stamford, CT 06902
ABOUT THIS HOME
West Side-Waterside-South End, CT Homes for Sale
Sale is contingent on Probate Court and Housing Authority approval. This property cannot be rented out. It must be owner occupied.

$379,000

3 beds2.5 baths1,380 sq ft

137 Wilson St #15, Stamford, CT 06902

$225 HOA • Garage

88 Southfield Ave #202, Stamford, CT 06902
88 Southfield Ave #202, Stamford, CT 06902
88 Southfield Ave #202, Stamford, CT 06902
ABOUT THIS HOME
West Side-Waterside-South End, CT Homes for Sale
2 bedroom, 2 bath unit on 2nd floor with million dollar water views of Stamford Harbor and beyond. Live like you are on vacation year 'round in this one level condo featuring an open floor plan with 9' ceilings and hickory floors. The eat-in kitchen with high end appliances, wood cabinetry and granite counters is open to the spacious living room with gas fireplace and stunning water views. The master bedroom is on the water side with a master bath that features marble and double vanities. Guest bedroom features a marble bathroom in the hall. Harbor Point with restaurants galore is just a water taxi away. Private terrace overlooking the harbor is the perfect spot to start and end your day. 4

$725,000

2 beds2 baths1,415 sq ft

88 Southfield Ave #202, Stamford, CT 06902

$1,000 HOA • Pool

Property at 18 Brown Ave #34, Stamford, CT 06902, 2 beds, 1 bath

$253,000

2 beds1 bath1,296 sq ft

18 Brown Ave #34, Stamford, CT 06902

Property at 35 Southfield Ave, Stamford, CT 06902, 4 beds, 2 baths

$849,990

4 beds2 baths2,242 sq ft

35 Southfield Ave, Stamford, CT 06902

Property at 20 Cook Rd, Stamford, CT 06902, 4 beds, 3.5 baths

$1,585,000

4 beds3.5 baths2,878 sq ft

20 Cook Rd, Stamford, CT 06902

Property at 37 Greenwich Ave Apt 1-2, Stamford, CT 06902, 3 beds, 1 bath

$360,000

3 beds1 bath1,170 sq ft

37 Greenwich Ave Apt 1-2, Stamford, CT 06902

Property at 19 Stillwater Ave Unit E, Stamford, CT 06902, 3 beds, 2.5 baths

$550,000

3 beds2.5 baths1,749 sq ft

19 Stillwater Ave Unit E, Stamford, CT 06902

Property at 17 Alden St, Stamford, CT 06902, 4 beds, 2 baths

$799,900

4 beds2 baths1,620 sq ft

17 Alden St, Stamford, CT 06902

Property at 16 Greenwood Hill St, Stamford, CT 06902, 8 beds, 5.5 baths

$1,200,000

8 beds5.5 baths5,231 sq ft

16 Greenwood Hill St, Stamford, CT 06902

Property at 50 Signal Rd, Stamford, CT 06902

$2,200,000

— beds— baths— sq ft

50 Signal Rd, Stamford, CT 06902

Property at 54 Signal Rd, Stamford, CT 06902

$2,200,000

— beds— baths— sq ft

54 Signal Rd, Stamford, CT 06902

Property at 42 Signal Rd, Stamford, CT 06902

$2,200,000

— beds— baths— sq ft

42 Signal Rd, Stamford, CT 06902

Property at 46 Signal Rd, Stamford, CT 06902

$2,200,000

— beds— baths— sq ft

46 Signal Rd, Stamford, CT 06902

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220 Halliwell Dr, Stamford, CT 06902
220 Halliwell Dr, Stamford, CT 06902
220 Halliwell Dr, Stamford, CT 06902
ABOUT THIS HOME
West Side-Waterside-South End, CT Homes for Sale
Stunning updated Colonial! Life doesn't get sweeter than this beautiful 4-bedroom, 3.5-bath Center Hall Colonial nestled in the desirable Hycliff community. Thoughtfully updated with all the bells and whistles, this home perfect blends classic charm & modern comfort! Step inside to an inviting open floor plan that connects the kitchen & dining areas-ideal for entertaining! The sleek, updated kitchen features modern appliances & flows seamlessly out to a private backyard oasis with a charming patio-perfect for al fresco dining or summer gatherings. The spacious living room features a cozy wood-burning fireplace, while the adjacent sunroom/library offers a quiet retreat for

$1,199,000

4 beds3.5 baths2,802 sq ft

220 Halliwell Dr, Stamford, CT 06902

0.26 acre lot • 2 garage spots • Open floor plan

71 Strawberry Hill Ave Apt 1116, Stamford, CT 06902
71 Strawberry Hill Ave Apt 1116, Stamford, CT 06902
71 Strawberry Hill Ave Apt 1116, Stamford, CT 06902
ABOUT THIS HOME
West Side-Waterside-South End, CT Homes for Sale
Enjoy sweeping city views, stunning sunsets, and the comfort of this refreshed 2-bedroom, 1-bath corner unit in a high-rise Stamford condo. Filled with natural light, the unit features tile flooring, fresh paint, and an open-concept living and dining area-ideal for entertaining. A private (not shared) balcony offers beautiful views of downtown Stamford, while both bedrooms enjoy abundant sunlight. Additional highlights include hallway storage and a full bath. The secure, gated building provides 24/7 security, two elevators, laundry facilities, basement storage, visitor parking, a fitness center, and an outdoor pool. One assigned parking space is included, and the monthly HOA covers heat, ho

$295,000

2 beds1 bath875 sq ft

71 Strawberry Hill Ave Apt 1116, Stamford, CT 06902

$716 HOA • Parking • Pool

1465 E Putnam Ave #430, Old Greenwich, CT 06870
1465 E Putnam Ave #430, Old Greenwich, CT 06870
1465 E Putnam Ave #430, Old Greenwich, CT 06870
ABOUT THIS HOME
West Side-Waterside-South End, CT Homes for Sale
1br with a loft, living room with high ceilings, walk-in closet in primary br, convenient location, deck, storage area, and heat & hot water included in common charges. Make this one your own. Unit sold ''As Is. '' Owner prefers closing after 9/10

$495,000

1 bed1 bath784 sq ft

1465 E Putnam Ave #430, Old Greenwich, CT 06870

Walk-in closet • Deck • Convenient location

COMING SOON

65 Glenbrook Rd Apt 5E, Stamford, CT 06902
ABOUT THIS HOME
West Side-Waterside-South End, CT Homes for Sale
Welcome to this charming condo located in the desirable Glenbrook area of Stamford. Boasting 2BR 2BTH, this property invites you to experience comfort and coziness in abundance. Enjoy the copious amounts of natural light pouring in from large, generous windows, complementing the beautiful hardwood floors. Beneficial utilities include heat, hot-water, trash, and a dedicated parking spot. Conveniently located, this home places you to nearby shopping, restaurants, train station and public transportation. Become part of this Glenbrook community and enjoy the warmth of this lovely property. Surely, you wouldn't want to miss out on this.

$379,000

2 beds2 baths1,336 sq ft

65 Glenbrook Rd Apt 5E, Stamford, CT 06902

$750 HOA • Parking

86 Myrtle Ave Apt 9, Stamford, CT 06902
86 Myrtle Ave Apt 9, Stamford, CT 06902
86 Myrtle Ave Apt 9, Stamford, CT 06902
ABOUT THIS HOME
West Side-Waterside-South End, CT Homes for Sale
Investor-friendly 2-bedroom, 1.5-bath end-unit three-level townhouse with strong cash flow potential. This bright, spacious corner unit features hardwood floors, central air, and an in-unit washer and dryer. The two-level living layout provides excellent space separation, making it ideal for tenants or future resale. Includes two covered, reserved parking spaces and benefits from exceptionally low common charges, which help the unit's cash flow at current market rents. The natural light from the primary bedroom's skylight adds to its appeal. An additional storage space is accessible from the exterior next to the front door. Freshly painted for you or a tenant to move right in! * * Cash or

$300,000

2 beds1.5 baths1,142 sq ft

86 Myrtle Ave Apt 9, Stamford, CT 06902

$250 HOA • 2 parking spots • End-unit townhouse

33 Halsey Dr, Greenwich, CT 06870
33 Halsey Dr, Greenwich, CT 06870
33 Halsey Dr, Greenwich, CT 06870
ABOUT THIS HOME
West Side-Waterside-South End, CT Homes for Sale
This charming Old Greenwich home in the highly sought-after North Mianus/ Eastern school district is the perfect starter or the best condo alternative. A picturesque setting, this single-family dwelling comes with low property taxes, low maintenance responsibilities and costs. The first floor offers comfortable living and family room spaces, a newer kitchen with quartz countertop and stainless steel appliances, along with 1 bedroom and a new hall bath. The 2nd floor consists of 2 bedrooms (one with spacious cedar closet) and another newer full bath. The private backyard with a bluestone patio provides a serene outdoor environment, surrounded by mature trees and plantings. Many updates throu

$1,495,000

3 beds2 baths1,481 sq ft

33 Halsey Dr, Greenwich, CT 06870

7,405 sq ft lot • Garage • Bluestone patio

Property at 5 Hunter St, Greenwich, CT 06870, 3 beds, 1.5 baths

$1,250,000

3 beds1.5 baths1,333 sq ft

5 Hunter St, Greenwich, CT 06870

Property at 43 Harbor Dr Apt 104, Stamford, CT 06902, 1 bed, 1.5 baths

$589,000

1 bed1.5 baths1,005 sq ft

43 Harbor Dr Apt 104, Stamford, CT 06902

Property at 1 Broad St Ph 27E, Stamford, CT 06901, 2 beds, 2.5 baths

$675,000

2 beds2.5 baths1,530 sq ft

1 Broad St Ph 27E, Stamford, CT 06901

Property at 50 Glenbrook Rd Apt 7C, Stamford, CT 06902, 3 beds, 3 baths

$489,000

3 beds3 baths1,680 sq ft

50 Glenbrook Rd Apt 7C, Stamford, CT 06902

Property at 25 Adams Ave #103, Stamford, CT 06902, 2 beds, 2 baths

$540,000

2 beds2 baths1,151 sq ft

25 Adams Ave #103, Stamford, CT 06902

Property at 65 Glenbrook Rd Unit 8B, Stamford, CT 06902, 2 beds, 2 baths

$385,000

2 beds2 baths1,336 sq ft

65 Glenbrook Rd Unit 8B, Stamford, CT 06902

Property at 75 Rachelle Ave, Stamford, CT 06905, 4 beds, 3 baths

$650,000

4 beds3 baths2,097 sq ft

75 Rachelle Ave, Stamford, CT 06905

Property at 1 Broad St Ph 26E, Stamford, CT 06901, 2 beds, 2.5 baths

$875,000

2 beds2.5 baths1,530 sq ft

1 Broad St Ph 26E, Stamford, CT 06901

Property at 127 Greyrock Pl Apt 1401, Stamford, CT 06901, 1 bed, 1 bath

$389,900

1 bed1 bath764 sq ft

127 Greyrock Pl Apt 1401, Stamford, CT 06901

Property at 51 Forest Ave #60, Old Greenwich, CT 06870, 1 bed, 2 baths

$799,000

1 bed2 baths947 sq ft

51 Forest Ave #60, Old Greenwich, CT 06870

Property at 104 North St Apt 803, Stamford, CT 06902, 2 beds, 2 baths

$599,000

2 beds2 baths1,729 sq ft

104 North St Apt 803, Stamford, CT 06902

Property at 51 Forest Ave #31, Old Greenwich, CT 06870, 1 bed, 2 baths

$825,000

1 bed2 baths1,160 sq ft

51 Forest Ave #31, Old Greenwich, CT 06870

Property at 90 Strawberry Hill Ave #3, Stamford, CT 06902, 2 beds, 1 bath

$285,000

2 beds1 bath860 sq ft

90 Strawberry Hill Ave #3, Stamford, CT 06902

Property at 71 Strawberry Hill Ave Apt 820, Stamford, CT 06902, 1 bed, 1 bath

$237,000

1 bed1 bath725 sq ft

71 Strawberry Hill Ave Apt 820, Stamford, CT 06902

Average home prices near West Side-Waterside-South End, CT

Cities

Neighborhoods

Newfield-Westover-Turn of River homes for sale
$739,000
Noroton homes for sale
$1,675,000
The Cove homes for sale
$745,000
Eastern Greenwich homes for sale
$3,472,500
North Old Greenwhich homes for sale
$2,175,000
Chesterfield homes for sale
$562,000
Shippan Point homes for sale
$1,524,500
Glenbrook homes for sale
$507,000
Downtown Stamford homes for sale
$479,000
Springdale-Glenbrook-Belltown homes for sale
$614,950

West Side-Waterside-South End, CT real estate trends

All Home Types trends in West Side-Waterside-South End, CT

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$705,944

+2.3% YoY | Jun 2025

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Jun 2025

Growth

% YoY

West Side-Waterside-South End, CT

$705,944

+2.3%

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