Middlesex County, CT Houses for Rent

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  $10,000 per month

  • 3 Beds
  • 2 Baths
  • 5,228 Sq Ft
  • House for Rent

  558 N Roast Meat Hill Rd, Killingworth, CT 06419

  Welcome to Living on the Farm, a one-of-a-kind Summer Rental May 23, 2026 to Sept 8, 2026 for only $40,000. Fully staffed, working equestrian estate (Yellow Stone Experience). The Main quarters are fully furnished, beautifully maintained, offer everything you would expect from a high-quality retreat-comfortable, clean, and thoughtfully designed. Set on 23 scenic acres, guests can enjoy a true

  Linda O'Hara William Raveis Real Estate

  558 N Roast Meat Hill Rd, Killingworth, CT 06419
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  $2,000 per month

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • House for Rent

  411 Main St Unit 1, Cromwell, CT 06416

  Well-located 3-bedroom, 1-bath home in a desirable Cromwell setting. Set on clear, level land in a quiet area just west of the Connecticut River, with easy access to shops, highways, and transportation. The layout is efficient and functional with spacious bedrooms and recent updates throughout. In-unit washer and dryer included. Plenty of off-street parking available. Tenant responsible for all

  Jeff P Puciato Realty Group

  411 Main St Unit 1, Cromwell, CT 06416
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  $2,550 per month

  • 1 Bed
  • 1 Bath
  • 1,700 Sq Ft
  • House for Rent

  23 Main St, East Haddam, CT 06423

  A spectacular luxury apartment. Originally a Masonic hall, it has the historic barrel ceiling and all old moldings throughout. The wood floors date back to 1863. There is a huge island with marble top and bar seats. All high end appliances - built in micro, Smart refrigerator, dishwasher. Also has a sleeping loft and access to a private gym and laundry. Did we mention a bathroom of utmost luxury.

  Allen Jacobs Sunset Creek Realty, LLC

  23 Main St, East Haddam, CT 06423
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  $3,200 per month

  • 2 Beds
  • 2 Baths
  • 2,015 Sq Ft
  • House for Rent

  740 Little City Rd, Higganum, CT 06441

  Beautifully restored 1780s farmhouse set on 14 peaceful acres, offering authentic New England charm with thoughtful modern updates. Stunning exposed wood beams and wide-plank floors highlight the home's character, while a gas-log fireplace creates a warm and inviting focal point. Renovated with sustainability and historical accuracy in mind, the home features reclaimed original trim and salvaged

  Jay Lafleur William Pitt Sotheby's Int'l

  740 Little City Rd, Higganum, CT 06441
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  $2,500 per month

  • 3 Beds
  • 1 Bath
  • 2,081 Sq Ft
  • House for Rent

  32 Wall St Unit 2, Middletown, CT 06457

  HEAT INCLUDED IN RENT! Spacious and fully renovated, this 3-bedroom, 1-bathroom apartment offers comfortable living with thoughtful upgrades throughout. The kitchen and bathroom have been completely remodeled with brand-new appliances and fixtures, and the entire unit has been freshly painted. You'll find hardwood floors throughout, new LED lighting, and updated door hardware throughout the

  Kris Robinson Eagle Eye Realty PLLC

  32 Wall St Unit 2, Middletown, CT 06457
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  $2,400 per month

  • 2 Beds
  • 1 Bath
  • 892 Sq Ft
  • House for Rent

  110 Great Hill Pond Rd, Portland, CT 06480

  Enjoy serene waterfront living in this charming 892 sq. ft. ranch home directly on Great Hill Pond. Featuring two bedrooms, this residence offers incredible views along with fishing, and kayaking opportunities right outside your door. The inviting three-season porch overlooks the pond, creating the perfect spot to relax or entertain. Inside, you'll find hardwood floors throughout, a washer and

  Theresa Bitondo Berkshire Hathaway NE Prop.

  110 Great Hill Pond Rd, Portland, CT 06480
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  $9,950 per month

  • 5 Beds
  • 3 Baths
  • 4,088 Sq Ft
  • House for Rent

  8 Jacob Ln, Killingworth, CT 06419

  Prepare to be WOWed by this far-from-typical Colonial! This gorgeous home has been completely reimagined and remodeled with the highest-end finishes throughout, blending timeless design with modern sophistication. The heart of this 4,000+ sqft home is the chef's kitchen, featuring a Sub-Zero refrigerator, Wolf range, and a stunning Carrara marble island-perfect for culinary enthusiasts and

  Melanie Scull William Pitt Sotheby's Int'l

  8 Jacob Ln, Killingworth, CT 06419
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  $4,000 per month

  • 4 Beds
  • 1.5 Baths
  • 2,180 Sq Ft
  • House for Rent

  422 Maple Ave, Old Saybrook, CT 06475

  Classic New England year round beach house across the street from the ocean in the private Knollwood beach area. This home has 4 bedrooms, 2 full baths and an outside shower ! Master bedroom has a king bed, 2nd bedroom has a full size bed, 3rd bedroom has a queen size bed and 4th bedroom has a full and twin bed. Stunning views on every side and amazing sunsets ! This is a great location the

  Dawn Caso Williams Realty Services

  422 Maple Ave, Old Saybrook, CT 06475
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  $6,500 per month

  • 4 Beds
  • 3 Baths
  • 3,762 Sq Ft
  • House for Rent

  17 Agawam Ave, Old Saybrook, CT 06475

  Fantastic Opportunity to Rent in Fabulous Fenwick! This charming water-view traditional Fenwick Cottage is available from September, 2026, through June 20, 2027! Boasting 4 bedrooms and 4 baths plus a huge third-floor rec room/bunk room space, the home offers over 3,700 sq. ft. of comfortable beach living. Open floor plan living room with walls of windows and French door access to a spacious back

  Lynn Lehrman Re/Max Valley Shore

  17 Agawam Ave, Old Saybrook, CT 06475
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  $7,500 per month

  • 4 Beds
  • 4.5 Baths
  • 4,708 Sq Ft
  • House for Rent

  15 Liberty St, Chester, CT 06412

  Exceptional Rental Opportunity in Chester's Quintessential New England Village. Experience refined living in this estate-like setting, exquisitely furnished and thoughtfully remodeled to the highest standards. Offering over 4,000 sq. ft. of light-filled luxury, this stunning home is available October 2025 through mid-May 2026. Property Highlights: 4 Bedrooms | 5 Baths - including an exceptionally

  Lynn Lehrman Re/Max Valley Shore

  15 Liberty St, Chester, CT 06412
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  $1,800 per month

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft
  • House for Rent

  70 Pond Meadow Rd, Ivoryton, CT 06442

  Freshly Painted 2 bedrooms/1 bathroom unit located in a quite complex Tenant responsible for electric/Internet Landlord is responsible for landscaping/snow/water good credit, no pets, and no smoking 1 year lease, 2 months Security deposit and first month rent due at lease signing

  Amru Abo-Alaial RE/MAX One

  70 Pond Meadow Rd, Ivoryton, CT 06442
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  $18,000 per month

  • 4 Beds
  • 3 Baths
  • 1,120 Sq Ft
  • House for Rent

  8 Belaire Manor, Old Saybrook, CT 06475

  Summer 2026 -- Available: June 15-30 for $9,000 -- Rented: July/Aug/Sept. This beautiful property is a direct waterfront, 4 bedroom, one-level home situated on a sandy beach in a private association. Wake up every morning to ocean waves, and enjoy the panoramic sunrises/sunsets which are magical here. Upon pulling into the driveway, you'll be greeted by breathtaking water views. The expansive

  Erika Raffles William Pitt Sotheby's Int'l

  8 Belaire Manor, Old Saybrook, CT 06475
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  $3,000 per month

  • 3 Beds
  • 2 Baths
  • 2,137 Sq Ft
  • House for Rent

  8 Clinton Ave, Old Saybrook, CT 06475

  Turn-key Academic Shoreline Rental for today's modern-living and tastefully decorated in Old Saybrook, CT. Beautifully renovated home in South Cove neighborhood great for morning walks with coffee or evening strolls with a cocktail in hand. This lovely light filled home has an open floor plan, custom built kitchen with modern stainless steel appliances, new hardwood floors throughout, first floor

  Terry McDonald McDonald Real Estate, LLC

  8 Clinton Ave, Old Saybrook, CT 06475
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  $5,000 per month

  • 4 Beds
  • 3.5 Baths
  • 2,679 Sq Ft
  • House for Rent

  21 Groveway Unit 21, Clinton, CT 06413

  The rate posted is the monthly off season academic rental rate Please ask for all other rates. Rental Comes FULLY FURNISHED. Additional information is stated in the last paragraph.This ocean front luxurious 4 bedroom 3 bath is a dream home in a high-end community located in Clinton, Connecticut. The property has just undergone a full renovation with a first floor bedroom. Spanning over 2,000 SF,

  Jorge Zea Blue Lighthouse Realty, Inc

  21 Groveway Unit 21, Clinton, CT 06413
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  $2,400 per month

  • 3 Beds
  • 1 Bath
  • 912 Sq Ft
  • House for Rent

  38 Seabreeze Rd, Old Saybrook, CT 06475

  This spectacular home with a fantastic location is an Academic Rental; from September 15, 2026 through May 15, 2027. Living in this Old Saybrook home is comfortable, near the beach and close to town with shopping and dining. Only a few steps to Cornfield Point, walk the quiet neighborhood and enjoy the gorgeous sunsets. This home is a perfect place of peaceful, tranquil days and evenings, with

  Terry McDonald McDonald Real Estate, LLC

  38 Seabreeze Rd, Old Saybrook, CT 06475
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  $8,400 per month

  • 3 Beds
  • 2.5 Baths
  • 2,336 Sq Ft
  • House for Rent

  25 W Shore Dr, Old Saybrook, CT 06475

  BEACHFRONT Beautifully renovated Furnished luxury waterfront $8400 weekly rental or 1200 a day for June 1st thru Sept. 15th or weekly at $8400. Waterviews from all rooms, private beach, plus cornfield point assocation amenties. Enjoy 3 bedrooms all with water-views, 2 full bathrooms, 1 half bathroom, fireplace, CA, new gourmet kitchen, generator, in beautiful seaside setting and neighborhood.

  Joel Lucas Coldwell Banker Realty

  25 W Shore Dr, Old Saybrook, CT 06475
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  /22

  $4,500 per month

  • 2 Beds
  • 2 Baths
  • 1,358 Sq Ft
  • House for Rent

  28 Beach Rd W, Old Saybrook, CT 06475

  Amazing views of Long Island Sound at 28 Beach Rd West, Old Saybrook! Beautiful Academic Rental "beach" home, with 3 bedrooms and 2 baths, available for your enjoyment, across the street from Chalker Beach with spectacular and unobstructed views of Long Island Sound. The open kitchen, dining and living room with a gas fireplace are the focal point of the home. The kitchen has gorgeous granite

  Terry McDonald McDonald Real Estate, LLC

  28 Beach Rd W, Old Saybrook, CT 06475
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  $3,500 per month

  • 3 Beds
  • 2 Baths
  • 1,008 Sq Ft
  • House for Rent

  18 Thompson Ln, Old Saybrook, CT 06475

  Available immediatly, if your looking for a place in Old Saybrook to enjoy the summer while your shopping for your forever home great short term rental with water views and plenty of privacy. The best of one level living this adorable ranch has 3 bedrooms and 2 newly renovated bathrooms. Everything is immaculate. This is a great location uniquely situated off of RT one but at the end of a cul de

  KD Kling William Raveis Real Estate

  18 Thompson Ln, Old Saybrook, CT 06475

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