Middlesex, CT Homes

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  $660,000

  • Land
  • 39 Acres
  • $17,116 per Acre

  0 Gildersleeve Rd, Portland, CT 06480

  Rare 38.56-Acre Parcel with Golf Course Views - Portland, CT Attention developers, investors, and visionaries-this is your opportunity to own a prime 38.56-acre parcel in scenic Portland, Connecticut. With stunning views overlooking a nearby golf course, this expansive property offers incredible subdivision potential or the perfect setting for a private estate. This raw piece of land is a blank

  

  Amy Rio

  Executive Real Estate Inc.

  (860) 981-0331

  0 Gildersleeve Rd, Portland, CT 06480
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  Explore Portland

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  /25

  $2,300 per month

  • 3 Beds
  • 1 Bath
  • 1,344 Sq Ft
  • House for Rent

  629 Main St, Portland, CT 06480

  Welcome to this beautifully refreshed 3-bedroom, 1-bath rental, perfect for those seeking comfort and convenience. Recently updated with new paint throughout, this home offers a bright, modern feel while still maintaining its cozy charm. The refinished hardwood floors throughout bring a touch of classic elegance. The bedrooms are generously sized with plenty of closet space, and the bathroom

  

  Amy Rio

  Executive Real Estate Inc.

  (860) 497-9150

  629 Main St, Portland, CT 06480
• 

  $380,000 Sold Jul 26, 2025

  • 1,516 Sq Ft
  • $251/SF
  • 3 Days On Market

  • 4 Beds
  • 1.5 Baths
  • Built 1864

  17 Strongs Ave, Portland, CT 06480

  Check out this charming 4 bedroom colonial built in 1864! Sitting on a level .22 acre deep lot with a new chain link run great for pets, a garden or chickens. Entirely updated with an open layout kitchen/ dining room, and attached living room on the first floor. Laundry is conveniently located in the main level half bath. The eat-in kitchen is fully updated with new subway tile back splash,

  Moira Dill mygoodagent

  17 Strongs Ave, Portland, CT 06480
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  Est $395,154 Not Listed For Sale

  289 Middle Haddam Rd, Portland, CT 06480

  289 Middle Haddam Rd, Portland, CT 06480
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  /2

  $789,900 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,521 Sq Ft

  62 Cornwall St, Portland, CT 06480

  Come custom build the Home of your dreams. With a wide selection of plans, and possible Options and upgrades, this is something you do not want to wait for!

  

  Amy Rio

  Executive Real Estate Inc.

  (860) 943-4408

  62 Cornwall St, Portland, CT 06480
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  /34

  $1,655 - $3,120 per month

  Brainerd Place

  Studio - 2 Beds

  69 Marlborough St, Portland, CT 06480

  Experience the perfect blend of history and modern elegance at Brainerd Place, a luxury apartment community built in historic Portland, CT. Where the charm of the past meets the sophistication of the present, our thoughtfully designed residences offer unparalleled comfort, state-of-the-art amenities, and timeless style. Immerse yourself in a setting that honors its heritage while providing the

  69 Marlborough St, Portland, CT 06480
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  $565,000 Sold Jul 25, 2025

  • 4,535 Sq Ft
  • $125/SF
  • 39 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 1924

  35 Summer St, Portland, CT 06480

  Truly a rare find! This one-of-a-kind Portland property features two distinct residences on 1.23 level, fenced-in acres in a quiet neighborhood just minutes from downtown. The main home, originally built in 1924 as the town doctor's residence, has been thoughtfully transformed by the current owners over the past 16 years. Offering 3,620 sq ft of living space, it includes 4 bedrooms, 3.1

  Olivia Crable Berkshire Hathaway NE Prop.

  35 Summer St, Portland, CT 06480
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  Est $649,034 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,595 Sq Ft

  113 Meshomasic Trail, Portland, CT 06480

  113 Meshomasic Trail, Portland, CT 06480
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  /39

  $699,900 Under Contract

  • 4 Beds
  • 4.5 Baths
  • 2,764 Sq Ft

  31 Crimson Heights, Portland, CT 06480

  Beautiful Colonial in Prime Location! Ideally situated just minutes from the town center and vibrant downtown Middletown, this spacious 4-bedroom, 5-bathroom colonial offers the perfect blend of comfort and convenience. Featuring gleaming hardwood floors throughout, a modern kitchen with stainless steel appliances, and a finished basement complete with a wet bar-perfect for entertaining. The main

  Jacek Mikolajczyk Berkshire Hathaway NE Prop.

  31 Crimson Heights, Portland, CT 06480
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  /39

  $2,400 per month

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

  60 Jobs Gate 2, Portland, CT 06480

  Direct Waterfront on Jobs Pond! This truly unique rental offers direct waterfront living and it is available immediately. This home features almost 1,000 sq ft offering 2 beds and 1 bathroom with an open-concept designed to maximize natural light & showcase stunning water views from every room. Inside, enjoy a recently updated interior with an open-concept living room, dining room & kitchen. The

  Margaretann Fiderio William Raveis Real Estate

  60 Jobs Gate 2, Portland, CT 06480
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  $124,900 Sold Jul 23, 2025

  • Land
  • 3.08 Acres
  • $40,552 per Acre

  • 358 Days On Market

  390 Cox Rd Unit 10, Portland, CT 06480

  NEW PORTLAND SUBDIVISION - KELSEYS POND ESTATES. Custom Homes by Lepore and Sons LLC. New land lots with views of Kelseys Pond across the road! Short distance to Meshomasic State Forest and the walking trails. Quarry Ridge Golf Course nearby. Minutes to all the amenities in Portland, Middletown and Glastonbury. Perfectly situated near Routes 2 & 9. Other lots available. One or more of this

  Steven Lepore West Wind Realty, LLC

  390 Cox Rd Unit 10, Portland, CT 06480
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  Est $338,108 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,526 Sq Ft

  55 E Main St, Portland, CT 06480

  55 E Main St, Portland, CT 06480
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  /40

  $649,900

  • 3 Beds
  • 4 Baths
  • 3,486 Sq Ft

  76 High St, Portland, CT 06480

  CHARMING and spacious colonial at The Highlands loaded with CHARACTER!! This beautifully maintained home offers the perfect blend of classic charm and modern updates. The stunning remodeled kitchen features Brazilian granite counters, stainless steel appliances, a large center island, and a sunny dining area-ideal for casual meals and entertaining. The inviting living room boasts a wood burning

  Jody Smaglis Coldwell Banker Realty

  76 High St, Portland, CT 06480
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  /10

  $2,200 per month

  • 3 Beds
  • 1.5 Baths
  • 2,517 Sq Ft
  • House for Rent

  36 Indian Hill Ave, Portland, CT 06480

  Stunning views with an even better living space! Welcome to this beautiful 3-bedroom, 1.5 bathroom rental with views of the CT river. The property features an open-concept kitchen, living, and dining area-perfect for modern living and entertaining. Plus, an oversized deck complete with a huge backyard that is ideal for relaxing or hosting. The main level offers two comfortable bedrooms with

  Alexandra Riccardi William Raveis Real Estate

  36 Indian Hill Ave, Portland, CT 06480
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  $425,000 Sold Jul 22, 2025

  • 1,759 Sq Ft
  • $242/SF
  • 4 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1947

  6 Victoria Rd, Portland, CT 06480

  Welcome to this expanded 2-bed (2 additional unfinished rooms on 2nd level), 2.5-bath Cape Cod set on a private, level lot and located near schools. Enjoy an open floorplan with custom woodwork, hardwood floors, a pellet stove, and split system heating/cooling. The main level features a spacious, sun-filled family room that offers the perfect gathering space with plenty of room for everyone to

  Elizabeth Harrison Hagel & Assoc. Real Estate

  6 Victoria Rd, Portland, CT 06480
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  Est $385,851 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,320 Sq Ft

  7 Myrtle Rd, Portland, CT 06480

  7 Myrtle Rd, Portland, CT 06480
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  /25

  $500,000

  • 3 Beds
  • 2.5 Baths
  • 2,141 Sq Ft

  5 Scenic Dr, Portland, CT 06480

  Welcome to this beautifully updated 3-bedroom, 2.5-bath home, thoughtfully designed and built by the original owners and lovingly maintained by the family ever since. The home features a fully finished walk-out lower level with excellent potential for an in-law suite or guest accommodations, offering flexibility to meet a variety of needs. Ideal for gardening enthusiasts, the expansive yard

  Christie Diaz-o William Raveis Real Estate

  5 Scenic Dr, Portland, CT 06480
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  $452,000 Sold Jul 16, 2025

  • 1,733 Sq Ft
  • $261/SF
  • 3 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1939

  44 William St, Portland, CT 06480

  HIGHEST & BEST BY MONDAY 6/16 @ 5:00 Welcome to my lovingly maintained and thoughtfully updated Cape-style home! Over the years, we've made numerous upgrades to enhance both comfort and functionality. The home is equipped with a 40-year roof (currently 18 years old), a 330-gallon oil tank, and hardwired smoke detectors for added peace of mind. The siding, windows, and doors have all been

  Angela Aresco Carl Guild & Associates

  44 William St, Portland, CT 06480
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  Est $344,582 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,824 Sq Ft

  5 Coe Ave, Portland, CT 06480

  5 Coe Ave, Portland, CT 06480
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  /40

  $649,000

  • 2 Beds
  • 2.5 Baths
  • 2,669 Sq Ft

  286 Marlborough St, Portland, CT 06480

  A Rare Blend of Lifestyle & Opportunity! They say you shouldn't mix business with pleasure - but this unique property might just be the exception. Upstairs, you'll find a bright and inviting two-bedroom, one-bath apartment, ideal for comfortable living or strong rental potential. Downstairs, a flexible commercial space - formerly a charming salon - awaits your vision. Whether it's a boutique,

  Kris Robinson Eagle Eye Realty PLLC

  286 Marlborough St, Portland, CT 06480
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  $169,500 Sold Jul 16, 2025

  • 848 Sq Ft
  • $200/SF
  • 5 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 2004

  1 Brush Pasture Ln Unit 313, Portland, CT 06480

  Move-in ready 1-bedroom, 1-bath, condo unit in desirable 55+ Portland community. This meticulously maintained third-floor unit, accessed by convenient elevator, boasts a spacious open concept living area that flows into a fully equipped kitchen with peninsula seating, perfect for everyday meals or entertaining. The interior of the unit has been freshly painted and features brand-new bedroom

  Kara Pedersen Carl Guild & Associates

  1 Brush Pasture Ln Unit 313, Portland, CT 06480
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  Est $335,249 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,450 Sq Ft

  38 High St, Portland, CT 06480

  38 High St, Portland, CT 06480
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  /40

  $635,000

  • 4 Beds
  • 2.5 Baths
  • 2,992 Sq Ft

  328 Old Marlborough Turnpike, Portland, CT 06480

  Spacious 4 bedroom Colonial on a private lot. Nicely laid out for entertaining in and out. Generous living areas. Home office. Family room with fireplace, vaulted ceiling, and custom inlay in the wood flooring. 4 Bedrooms upstairs including a primary suite with a custom bath, walk-in closet and balcony. Partially finished basement with room for a rec. room, home gym, hobby room etc. The private

  Craig Milton Re/Max Valley Shore

  328 Old Marlborough Turnpike, Portland, CT 06480
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  $600,000 Sold Jul 14, 2025

  • 2,648 Sq Ft
  • $227/SF
  • 60 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 2004

  5 Pear Orchard Rd Unit 5, Portland, CT 06480

  This is your chance to come live in the wonderful 55+ community of Bartlett Hill! This move-in ready "Kent" style home is 2648 total sf - it was the model home for the builder! This home is gorgeous! It has an open floor plan, a first floor primary bedroom suite with large bath with separate vanities and a walk-in closet plus two more. The kitchen connects with the dining area and the freshly

  Georgia Newcomb Houlihan Lawrence WD

  5 Pear Orchard Rd Unit 5, Portland, CT 06480
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  Est $471,325 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,140 Sq Ft

  118 Rose Hill Rd, Portland, CT 06480

  118 Rose Hill Rd, Portland, CT 06480
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  /37

  $585,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,336 Sq Ft

  26 Rockwood Dr, Portland, CT 06480

  Welcome to Paley Farms, a sought-after neighborhood known for its peaceful setting and community charm. This beautifully maintained home offers bright, airy living spaces and is truly move-in ready, thanks to a long list of recent upgrades. In the past five years, the current owners have taken care of major updates including a new roof, furnace, central air system, water heater, kitchen

  Carly Luciér Our Home Realty Advisors

  26 Rockwood Dr, Portland, CT 06480
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  $400,000 Sold Jul 11, 2025

  • 1,853 Sq Ft
  • $216/SF
  • 43 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1954

  5 Brainerd Dr, Portland, CT 06480

  Welcome to this charming 3-bedroom, 1 1/2 bath Colonial nestled on a quiet cul-de-sac in a convenient in-town location. This beautifully maintained home features gleaming hardwood floors throughout and has been freshly painted for a move-in ready experience. The spacious living room offers a cozy fireplace, and there's a formal dining room perfect for gatherings. The remodeled kitchen features

  Cheryl Zalewski eXp Realty

  5 Brainerd Dr, Portland, CT 06480
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  Est $630,213 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,748 Sq Ft

  1086 Portland Cobalt Rd, Portland, CT 06480

  1086 Portland Cobalt Rd, Portland, CT 06480
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  /40

  $499,900 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,538 Sq Ft

  126 Penfield Hill Rd, Portland, CT 06480

  For sale for the first time in decades, this remarkable center chimney Colonial, The Daniel Burton House, is graciously set on 4 pastoral acres. This property is on of the most beautiful roads in Portland and it is truly a magical setting - you can feel it as soon as you pull in the driveway. With 2538 sf of living space, the layout successfully blends history and modern living, the best of both

  Georgia Newcomb Houlihan Lawrence WD

  126 Penfield Hill Rd, Portland, CT 06480
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  $685,000 Sold Jul 09, 2025

  • 2,841 Sq Ft
  • $241/SF
  • 15 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2000

  67 Stephen Tom Rd, Portland, CT 06480

  Beautifully crafted and meticulously maintained, this custom one-owner home-built in 2000-is set back from a quiet street, offering exceptional privacy and peaceful living. Enjoy stunning sunsets and wildlife views from the wraparound porch or entertain on the expansive Trex deck with a pergola, overlooking two man-made waterfalls and ponds designed to house fish and frogs and create a relaxing

  Angela Aresco Carl Guild & Associates

  67 Stephen Tom Rd, Portland, CT 06480
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  Est $316,963 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,120 Sq Ft

  16 Susan Cir, Portland, CT 06480

  16 Susan Cir, Portland, CT 06480
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  /40

  $585,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,564 Sq Ft

  72 Cox Rd, Portland, CT 06480

  Absolutely beautiful cape gracefully set amongst meticulously kept grounds. Charm and elegance are around every corner of this updated and lovingly cared for home. Numerous updates include an updated kitchen and baths (2023), newer roof (2020) and septic (2019). The family room with beautiful wood plank cathedral ceiling leads to a deck overlooking the yard with pool and stone shed with screened

  Siobhan McLaughlin William Raveis Real Estate

  72 Cox Rd, Portland, CT 06480
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  $700,000 Sold Jul 09, 2025

  • 3,750 Sq Ft
  • $187/SF
  • 33 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 2002

  74 High St, Portland, CT 06480

  Tucked away in nature yet minutes from downtown Portland, this stunning McGinley custom home offers over 3,750 sq ft of luxury living - with public utilities! Step into the grand foyer and fall in love with the open layout, soaring ceilings, sun-filled windows, and an oversized fireplace that anchors the space beautifully. The chef's kitchen boasts granite counters, an 8-foot island, double

  Amy Rio Executive Real Estate Inc.

  74 High St, Portland, CT 06480
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  Est $378,931 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,538 Sq Ft

  1 Woodland Rd, Portland, CT 06480

  1 Woodland Rd, Portland, CT 06480
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  /30

  $450,000

  • 3 Beds
  • 2 Baths
  • 1,925 Sq Ft

  121 Rose Hill Rd, Portland, CT 06480

  Welcome to the George Cox House, built circa 1855 and steeped in rich local history. Once part of a bustling 18th- and 19th-century mill site that provided flour to the Continental Army, this is one of Portland's most picturesque and storied locations. The 3-bedroom, 2-bath home offers original wide plank floors, exposed beams, and stone walls. It needs some work, but the charm and bones are

  Carl Guild Carl Guild & Associates

  121 Rose Hill Rd, Portland, CT 06480
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  $325,000 Sold Jul 08, 2025

  • 1,362 Sq Ft
  • $239/SF
  • 1 Day On Market

  • 2 Beds
  • 2.5 Baths
  • Built 2001

  2 Cinnamon Ln, Portland, CT 06480

  Take a look at this beautiful, free standing condo, with 2 bedrooms and 2.5 baths, in the Grandview Farms active adult community (55+)! There are hardwood floors in the Primary Bedroom and the Dining Rm, new plank flooring in the Living Room. The Living Rm is oversized and could include an office space or sun room. The Primary Bedroom has its own full bath and double closets! The Kitchen has lots

  Rick Berkenstock Century 21 AllPoints Realty

  2 Cinnamon Ln, Portland, CT 06480
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  Est $521,193 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,496 Sq Ft

  63 Rose Hill Rd, Portland, CT 06480

  63 Rose Hill Rd, Portland, CT 06480
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  /14

  $60,000

  • Land
  • 0.54 Acre
  • $111,111 per Acre

  0 Gadpouch Rd, Portland, CT 06480

  Approved Building Lot Near Great Hill Pond Don't miss this rare opportunity to own a fully approved .54-acre lot on quiet and scenic Gadpouch Road in East Hampton, Connecticut. Ready for your dream home, the property has completed soil testing and is fully approved for building-saving you time and money. Located just under half a mile from beautiful Great Hill Pond, perfect for kayaking,

  Joel Espada Coldwell Banker Realty

  0 Gadpouch Rd, Portland, CT 06480
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  $302,000 Sold Jun 27, 2025

  • 2,060 Sq Ft
  • $147/SF
  • 47 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1970

  17 Adorno Dr, Portland, CT 06480

  This classic 3-bedroom, 1.5-bath Colonial offers timeless appeal and solid potential. Nestled at the end of a peaceful cul-de-sac, this single-family home features a traditional layout with a formal dining room, spacious living room, and a cozy family room complete with a fireplace-perfect for relaxing evenings. The partially finished walkout basement provides additional living or storage space.

  Ellen Paklos William Raveis Real Estate

  17 Adorno Dr, Portland, CT 06480
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  Est $412,062 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,792 Sq Ft

  51 High St, Portland, CT 06480

  51 High St, Portland, CT 06480

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