Connecticut Retirement Communities
for over 55 (40)

Connecticut Counties on this Page:

Stony Creek Connecticut HarborStony Creek Harbor shoreline
New Haven


New London






Most Popular Communities in Connecticut Chart

New Haven County - New Connecticut Retirement Communities for Over 55

Orange, Connecticut, Retirement Communities

  • Beecher Walk at Orange - Dock on Indian Lake, walking trails.  Villas starting at $200's.  Call Beth Cantor at 203-288-1821 Ext 457 (Agent), Calcagni Real Estate, for appointment to see M-F.   100 South Orange Center Rd., Orange
Connecticut sailboat

Beacon Falls

  • EG Homes at Chatfield Farms - 3 large detached floor plans start in mid-$300's - charming country ambience - low maintenance community on 140 acres - clubhouse, pool, hot tub, fitness, social activities and more.  
    100 Fieldstone Lane, Beacon Falls - 203-714-6622 - Open Daily 

Oxford 55+ Communities

  • The Village at Oxford Greens - Sold - by Del Webb at Oxford - access to high-end golfcourses. Price: $$$-$$$$ - 15 miles to New Haven. 

  • New  Fairview at Oxford Greens carriage homes by Del Webb starting in $290's.  
    642 Championship Dr. - 866-313-9322 - Open 10-5 Daily


  • Castle Heights in Cheshire - Large community of spacious upscale single homes. Very new designs and home features.  (I love the bathrooms.) New Haven County by Carrier Homes. Upper $400's.
    141 Victoria Dr., Cheshire
    Open Thurs thru Mon 1-4 or by appointment. 860-798-2221
  • Richmond Glen Cheshire in New Haven county -  large single new homes in $400's -  small maintenance-free community of 41 one and two-story homes.  On 32 acres.  Phase II now.  Brodach Builders -  Wiese Rd.  - 203-272-1821

New Haven

  • Breakwater Bay - New Haven - not for over 55 but is a waterfront condo development with water views - priced from $200's. Good for commute. 150 Harbour Close Rd. - Call for appt. 203.439.1625


  • Regency at Prospect- New Haven by Toll Brothers - townhouse gated community from $290's. Pool, clubhouse and more. 36 golf courses in the area. Near Waterbury and I-84.
    120 Scott Rd., Prospect, CT - Phone: 203-758-4494 - Open Daily


Riverwalk in Branson Ct

Branford - Donmar Development Corp. New England-styled small to large homes start low $400's. Near train station for commute to Boston or New York, Yale University and YMCA. A shore community on the Long Island Sound. 287 E. Main St. - 203-464-0125 - By appt


Stony Creek Harbor in Branford Photos Near the Riverwalk 55+ Community

Stony Creek harbor Branford CtStony Creek Harbor in Branford

The Connecticut shoreline consists of numerous coves and harbors--this is just one in Stony Creek. View a map of the Connecticut shoreline.

On our visit, we found it amazingly peaceful. None of these boats are yachts--just small pleasure boats in seasonal slips. Seniors were out strolling or in their small motorboats.

Docks and slips and small boats everywhere in this cozy cove...

cove and homes
boats in cove
Stony Creek Harbor dockStony Creek Harbor dock


Resales in New Haven County:

  • Fieldstone Village Orange, Connecticut - Sunrise Development Group - Price: $$$-$$$$$$ - priced in $300's+.  Luxury homes by long-time local builders familiar with over 55 living. Short drive to New Haven.New England-styled medium to large homes. Clubhouse, amenities and activities. Many floor plan options. Near Merritt Pkway - HOBI Award.  1025 Grassy Hill Road  
  • Chatfield Farms - Beacon Falls - EG Homes - small, medium and large homes in $300's and $400's. All the amenities and activities in single homes of traditional styling. Clubhouse, pool, social activities.
    100 Fieldstone Lane, Beacon Falls  
  • County Walk Village - East Haven - desirable area near shore - condo ranches  priced under $200,000 - County Walk Lane, East Haven - Contact your Realtors to see.
  • Golf Crest - Single ranch homes good for downsizing.  Resales - See local Realtors.  Garages and basements available; low homeowners (verify all information--we are not responsible for inaccuracies).  Upscale interior amenities.  Pinehurst Dr., East Haven 
  • Quail Run by Calcagni in North Haven - condominiums.
  • Hamden Farms in Hamden by Calcagni - attached 1 and 2 bedroom homes with garage. 2620 Whitney Avenue  
  • Pond View North Haven by Calcagni - duplex styled homes in $200's. See local Realtors for resales.

  • Heritage Village - Southbury - 1, 2 and 3-bedroom homes and carriage homes for resale - large community of 2850   condos on 1000 acres in foothills of the Berkshires.  One of the first active adult communities on East Coast.  Formerly Victor Borge's estate.  

    Tennis court, pools.  Many activities. Garden plots, wood working, photo lab, pottery workshop, stained glass, computer lab, gym. 4 pools. 18-hole golf on nearby course.  Near East Coast gaming centers.  1 Heritage Way, Southbury 
  • Preston Woods in Meriden - just 13 detached condo homes built on cul-de-sac. - priced from upper mid-$200's.   By Preston Woods.
  • Simpson Village - Wallingford - live in town and be near YMCA, parks, tennis, dining and more. Energy Star homes started from low $250's. By Simpson Development.  Some luxury features were included in price.  701 Center St., Wallingford     
  • Trailside Village - Hamden - luxury reasonably-priced attached ranch homes. ($200's-verify pricing) 

Hartford County - New


  • Bidwell Village -  Coventry - 5 minutes to the University of Connecticut - Single homes and duplex homes in small 55+ community. - Open Thursday through Sunday or anytime by appointment.  94 Stonehouse Rd., Coventry - 860-748-1821 (Sales)

Resales in Hartford County:

  • Autumn Estates - Farmington by Carrier Inc. medium to large homes. 1 Hazelnut Dr. - Now sold out - check with local Realtors.
  • Chimney Hill Estates - Farmington by Carrier Home Builders Inc -  Single homes near upscale dining and golf and country clubs. Spacious homes in small luxury community.   Now sold out.
  • Newington Ridge Preserve - By My CT Dream Home - 10 minutes to Hartford - small community of 2-3 bedroom detached homes - 5 floorplans - Started mid-$300's - 
    Deming St., Newington, CT
  • Orchard Hill - Bristol between Waterbury and Hartford - upscale contemporary single homes in 55+ community priced in mid-$300's plus. Pond and country views. Townhomes to be built in a later phase.
  • Kari Court - Windsor - Cape Cod style homes with 1 garage.
  • Regency at Berlin - Toll Brothers - 50+ - between Hartford and New Haven. townhomes started in $200's - sold out - Bannan La., Berlin
  • Phillips Farm - East Hartford - Phillips Farm Rd - single condos priced in high $100's.  See Realtors for resales.
  • Fairfield Village - Glastonbury - 2 bedroom contemporary ranch condominiums with 2-car garages priced in upper $200's.
  • Oxbow Ridge - Canton - northwest ct - resales built 2003-06 - 96 spacious singles or townhomes priced in the $300's.
  • Hunt Glen - Granby - small community of contemporary-styled 2- bedroom homes priced in $300's. Granby is a small town of approx. 10,000 pop.
  • River Park Crossing - Rocky Hill - Rocky Hill is on the Connecticut River.  2-4 bedroom homes started at the $300's.  By Rocky Hill Enterprises.  Dividend Rd., Rocky Hill

New London County


  • North Woods of Colchester - Small to medium detached homes start in $300's.  Award-winning designs - Southeast Connecticut 25 miles to Hartford -  351 Lebanon Ave., Colchester - 860-537-5338 - Open Daily

Fairfield County


  • New  Rivington - The Enclave Collection
    By Toll Brothers - this is the 55+ community within the master community of Rivington - 2 and 3-bedroom carriage homes - location is on New York-Connecticut border with excellent shopping and views.  Prices start $500's.
    300 Center Meadow Lane, Danbury - 203-744-4600 - Open Daily


  • Maple Oak Reserve - Sold Out - Coastal Town - Just 42 large 3 bedroom, 2 1/2 bath single homes started from $490's - Near Long Island Sound - Clubhouse and Fitness - Homes feature front porches, kitchens with center island, basements and more.  Stratford, CT
  • Oronoque Village - North Stratford - 900+ condos look like part chalet and part cottage. Some have great features like cathedral ceilings, 1- car garages and lots of storage space. Some are detached but most are attached. Community amenities include 3 pools, tennis, vegetable gardens, community center, nearby golf club, library activities.
    600 North Trail. - 203-377-5313.

Newtown Woods

  • Newtown Woods by Toll Brothers in Newtown - luxury single level condos start low $300's and 2-bedroom townhomes start upper $300's - Outdoor pool, fitness, clubhouse.  Near Danbury - Nearby public golf at Richter Park Memorial golf course. Short distance to I-84.
    176 Mount Pleasant Road, Newtown - Phone: 203-364-9900 - Open Daily


  •  The Summit at Bethel - Bethel - near train station for commute to New York, Stamford and Norwalk. Award-winning - At completion will have 232 townhomes in 2 collections.  By Toll Brothers from mid-$400's.  10 Great Hill Dr., Bethel - 203-792-3500

Middlesex County Retirement Communities in Connecticut


  • Mystique Lane - Old West St., Cromwell from $249,900 - 26 detached condos. By J.D. Bender Homes.  Now sold out.  Phone Real Estate rep: 203-265-1821

East Hampton

  • Laurel Ridge in East Hampton - detached homes
    North Cove Crossing - Old Saybrook - small community of detached spacious homes near the shore. Watch the sailboats flit by. 
    Phone - 860-388-3623 at 81 Coulter St. #3 or see Realtors for resales.

Old Saybrook

  •  North Cove Crossing - Old Saybrook - small community of detached spacious homes near the shore. Watch the sailboats flit by. Homeowners association information: phone - 860-388-3623 at 81 Coulter St. #3 or see Realtors for resales.

Litchfield County

  • Tall Oaks - New Milford - Detached homes.

Tolland County

  • Belvedere Ridge - Tolland - on 44 wooded acres with walk trails - 66 detached homes offering a variety of floor plans.
    601 Old Post Rd - Phone: 860-896-0101


  • Heritage Commons - rent includes meals and housekeeping vegetarian meals options.  20 minutes to Hartford.  Adult Day program available.
    38 Boston Rd., Middletown - 860-344-1221
  • Bella Vista - New Haven apartments with an active lifestyle. Large apartment complex in Connecticut since 1971. Plans are being made for expansion adding new apartments and amenities. On New Haven bus line.

Most Popular 55+ Communities in Connecticut*




1. Beecher WalkOrange/$299,990More
2. NorthwoodsColchester/$300'sMore
3. RiverwalkBranford/$400'sMore
*As determined by most click-thrus on this page in the last 3 months.

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