Best Condo Options for Downsizers in Fairfield & Westport, CT

(2026 Guide)

Downsizing sounds simple-until you actually start looking.  Many homeowners in Fairfield and Westport are ready for a lifestyle shift:

• Less maintenance
• Fewer stairs
• More convenience

But what we see every day is this: the inventory that truly works for downsizers is limited and highly competitive.  Not every condo advertised as “main floor living” functions that way in practice. And elevator-access options are even more limited.  Below is a breakdown of communities in Fairfield and Westport organized by what downsizers are actually looking for.

*Typical pricing is based on closed sales over the past two years, where available, and may not reflect current market conditions. 

Fairfield, CT Condo Options for Downsizers

Main Floor Primary / Ranch-Style Living

Southport Woods

• Setting: Southport near Post Road, close to village and train
• Community Size: 152 units
• Amenities: Pool, clubhouse, paddle court, some detached garages
• Typical Size: ~1,200–1,500 sq ft
• Typical Pricing: ~$525,000–$629,750
• Reality Check: Limited storage; ranch units move quickly

Woodfield Village

• Setting: Stratfield area
• Community Size: 134 units
• Amenities: Pool, clubhouse, tennis, garages
• Typical Size: ~1,100–2,050 sq ft
• Typical Pricing: ~$510,000–$875,000
• Reality Check: Low turnover and not all units have main floor primary suite.

Stratfield Falls

• Setting: Near Merritt Parkway
• Community Size: 28 units
• Amenities: Landscaped grounds, attached garages
• Typical Size: ~1,782–3,300 sq ft
• Typical Pricing: ~$682,000–$1,150,000
• Reality Check: Some highway noise.  Most units back up to Fairchild Wheeler Golf Course

The Meadows

• Setting: Beach area
• Community Size: 48 units
• Amenities: Pool, garage
• Typical Size: ~1,965 sq ft
• Typical Pricing: ~$1,025,000–$1,105,000
• Reality Check: Flood zone but walk to beach.

Mosswood

• Setting: In-town location
• Community Size: 136 units
• Amenities: Assigned Parking, storage lockers
• Typical Size: ~900–1,600 sq ft
• Typical Pricing: ~$400,000–$815,000
• Reality Check: No garages, limited in unit storage and not many true ranch style floor plans- units move quickly

Quincy at Southport

• Setting: Southport near Post Road
• Community Size: 40 units
• Amenities: Pool, parking, some garages services
• Typical Size: ~1,150 sq ft
• Typical Pricing: ~$479,000–$552,000
• Reality Check: Smaller units but many appreciate the location.

Condo Communities with Elevator Access

Stone Ridge

• Setting: Near Fairfield Metro
• Community Size: 70 units
• Amenities: Elevators, gym, concierge services and covered parking
• Typical Size: ~1,126–1,769 sq ft
• Typical Pricing: ~$530,000–$801,000
• Reality Check: Strong no-stairs option but in a predominantly commercial area

Southgate

• Setting: Southport near harbor and train
• Community Size: 16 units
• Amenities: Garages, some units with elevators
• Typical size: 1,984-3,052 sq. Ft
• Typical pricing: $952,000-$1,165,000
• Reality Check: Limited turnover, some highway noise but great walk to village location

Southport Green

• Setting: Walkable Southport location
• Community Size: 24 units
• Amenities: Garages, some elevators
• Typical Size: ~2,320–3,328 sq. ft
• Typical Pricing: ~$1,500,000–$2,300,000
• Reality Check: Rare availability highly sought after village location

Village at Southport

• Setting: Near Southport Village on Westway Road
• Community Size: 16 units
• Amenities: Garages, some elevators
• Typical Size: ~3,805 sq. ft
• Typical Pricing: ~$1,700,000–$1,800,000
• Reality Check: Some noise from nearby transit but walk to town location

Westport, CT Condo Options for Downsizers

Main Floor Primary / Ranch-Style Living

Harvest Commons

• Setting: Long Lots area off Post Road
• Community Size: 82 units
• Amenities: Pool, tennis, garages
• Typical Size: ~1,662–2,774 sq. ft
• Typical Pricing: ~$1,100,000–$1,500,000
• Reality Check: Units sell quickly; special tax district

Lansdowne

• Setting: Greens Farms gated community
• Community Size: 90 units
• Amenities: Pool, tennis, garages
• Typical Size: ~2,050–2,450 sq. ft
• Typical Pricing: ~$1,030,000–$1,510,000
• Reality Check: No basement; special tax district

Terra Nova

• Setting: Old Hill gated community
• Community Size: 54 units
• Amenities: Pool, attached 2-car garages, some elevators
• Typical Size: ~2,337–2,988 sq ft
• Typical Pricing: ~$1,450,000–$1,625,000
• Reality Check: Not all units have main floor primary

Condo Communities with Elevator Access

The Mill at Westport

• Setting: Walkable to downtown Westport
• Community Size: 31 units
• Amenities: Pool, concierge, gym, cafe
• Typical Size: ~1,300–2,400 sq ft
• Typical Pricing: ~$1,300,000–$3,000,000
• Reality Check: Rare resale opportunities but good walk to town location

Bankside House

• Setting: Saugatuck River, walk to town
• Community Size: 12 units
• Amenities: Gym, covered parking, soundproofing
• Typical Size: ~2,437–2,517 sq ft
• Typical Pricing: ~$3,334,101 median
• Reality Check: Not all units have river views but luxurious amenities.

Downsizing in Fairfield County isn’t about finding the perfect property-it’s about finding the right next fit based on how you want to live day-to-day.  With limited inventory in both Fairfield and Westport, the most functional units tend to move quickly and, in some cases, never hit the open market.

There are also a few new condo developments in the works that may offer additional options in the near future. If you’d like insight into what’s coming-and what might be worth waiting for, we’re always happy to connect.