Homes for Sale near Valley Regional High School

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  /39

  $2,200,000

  • 4 Beds
  • 3.5 Baths
  • 3,957 Sq Ft

  47 E Kings Hwy, Chester, CT 06412

  A once-in-a-generation opportunity to become the steward of one of the Connecticut River Valley's most important historic estates. Built in 1798 by Jonathan Warner-founder of the Chester-Hadlyme Ferry, merchant, ship owner, farmer, Constable, Justice of the Peace, civic leader, and director of the Middlesex Turnpike-the Warner-Brooks House stands as a remarkable testament to early American

  

  Al Chiarito

  Chiarito Real Estate LLC

  47 E Kings Hwy, Chester, CT 06412
• 

  Explore Valley Regional High School

• 

  

  

  /37

  $1,150,000

  • 8 Beds
  • 6 Baths
  • 7,300 Sq Ft

  87 Main St, Deep River, CT 06417

  VC Property Group is proud to present a rare two-parcel assemblage in Deep River, Connecticut, featuring a newer construction single-family residence, a five-unit mixed-use building with four residential apartments and one retail unit, and a contiguous 0.30-acre vacant parcel. Located in the highly desirable Lower Connecticut River Valley, the property is just 0.4 miles from Downtown Deep River

  

  Anthony Velez

  VC Property Group, LLC

  87 Main St, Deep River, CT 06417
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  /27

  $220,000

  • Studio
  • 1 Bath
  • 540 Sq Ft

  15 Sunset Terrace Unit 9, Essex, CT 06426

  Thoughtfully reimagined and beautifully remodeled, this fully furnished studio condominium offers a rare opportunity to own a turnkey retreat in the heart of Essex Village. Just bring your clothes-everything else has been carefully curated. Designed with both style and function in mind, the interior features all new windows, skylights, flooring, lighting, paint, custom details, and a beautifully

  

  Kelly Puorro

  Puorro Realty Group

  15 Sunset Terrace Unit 9, Essex, CT 06426
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  /37

  $999,000

  $191K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,905 Sq Ft

  13 Mill Rd, Essex, CT 06426

  Nestled at the end of a private lane in one of Essex Village's premier waterfront settings, this exceptional residence offers a rare blend of privacy, natural beauty, and walk-to-town convenience. Set on 1.5 acres overlooking Falls River Pond and North Cove, the property enjoys year-round water views, abundant wildlife, and room for future expansion. Designed to embrace its surroundings, the home

  

  Kelly Puorro

  Puorro Realty Group

  13 Mill Rd, Essex, CT 06426
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  /6

  $979,860

  New Construction

  • 4 Beds
  • 3 Baths
  • 2,246 Sq Ft

  130 Mares Hill Rd, Essex, CT 06442

  Stunning new construction ranch set on a beautiful level lot, just under an acre. Thoughtfully designed for both comfort and flexibility. This To-Be Built contemporary home will feature an open-concept layout with a spacious kitchen, center island, and seamless flow to the living and dining areas-perfect for entertaining and everyday living. The private primary suite offers a walk-in closet and

  

  Kiki Sydnor

  Choice Realty

  130 Mares Hill Rd, Essex, CT 06442
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  /40

  $795,000

  $30K PRICE DROP

  • 6 Beds
  • 3 Baths
  • 4,184 Sq Ft

  163 Main St, Deep River, CT 06417

  Rare mixed-use investment opportunity located in the heart of desirable Deep River Village. Positioned directly on Main Street, this 5-unit asset offers a strong blend of residential and commercial income within one of the Connecticut shoreline region's most sought-after rental and retail markets. The property consists of 3 residential apartments and 2 commercial storefronts occupied by long-term

  Connor Wenchell VC Property Group, LLC

  163 Main St, Deep River, CT 06417
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  /26

  $2,195,000

  • 8 Baths
  • 12,155 Sq Ft

  31 N Main St, Essex, CT 06426

  Signature building in Essex Village. Originally the EE Dickinson corporate offices; grandfathered use in a residential zone. Reimagine this amazing space, water views, Essex Village, .78 acres of land, large footprint. Rare opportunity to own a cherished piece of Essex history

  Susan Malan William Pitt Sotheby's Int'l

  31 N Main St, Essex, CT 06426
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  /40

  $1,150,000

  • 2 Beds
  • 2.5 Baths
  • 3,278 Sq Ft

  112 River Rd, Essex, CT 06426

  A remarkable blend of architecture, nature, and modern comfort, this modernist custom home offers a living experience unlike any other. Nestled within a private and serene setting, the property is surrounded by natural beauty, where meandering streams feed a tranquil pond that spills into a cascading waterfall before winding through the marshlands toward the Connecticut River. The setting is both

  Gigi Giordano Taylor Compass Connecticut, LLC

  112 River Rd, Essex, CT 06426
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  /40

  $825,000

  Open Sun 11AM - 12:30PM $170K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,343 Sq Ft

  136 Goose Hill Rd, Chester, CT 06412

  Welcome to 136 Goose Hill Rd. This home has been tastefully redesigned inside and out with no expense spared. Featuring 4 bedroom, 3 full bathroom, over 3,300 sq ft of beautifully finished living space sitting on just over 2 acres. Step inside to discover all-new hardwood flooring throughout the main level and a thoughtfully designed open-concept layout ideal for both everyday living and

  Chris Torrez RE/MAX One

  136 Goose Hill Rd, Chester, CT 06412
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  /19

  $75,000

  $25K PRICE DROP

  • Land
  • 1 Acre
  • $75,000 per Acre

  0 Turkey Hill Rd, Chester, CT 06412

  Discover the perfect setting to build your dream home in the desirable Wig Hill area of Chester, Connecticut. Located near Cockaponset Sate Forest and the scenic Connecticut River valley. This beautiful one-acre level building lot features approximately 211 feet of road frontage and dimensions of roughly 200 x 200 feet, offering ample space and flexibility to bring your custom plans and ideas to

  Charles Kroopneck Charles Kroopneck Real Estate

  0 Turkey Hill Rd, Chester, CT 06412
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  /37

  $1,995,000

  $105K PRICE DROP

  • 11 Beds
  • 12 Baths
  • 8,500 Sq Ft

  59 Maple St, Chester, CT 06412

  A mixed-use and multifamily package located in Chester and Deep River, two of the most desirable towns in the Lower Connecticut River Valley. The offering includes: 59 Maple Street (Chester): 7-unit multifamily asset with an additional ~1,500 SF commercial warehouse on 2.5+ acres. 163 Main Street (Deep River): 5-unit mixed-use property positioned at the gateway to the downtown retail corridor.

  Connor Wenchell VC Property Group, LLC

  59 Maple St, Chester, CT 06412
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  /36

  $1,595,000

  • 3 Beds
  • 2.5 Baths
  • 2,708 Sq Ft

  46 West Ave, Essex, CT 06426

  1/2 mile walk to Essex Village, the marina, shops, and restaurants, this historic residence is nestled within one of Essex's most desirable neighborhoods. Thoughtfully reimagined by an established interior designer, the home masterfully blends modern luxury with the timeless charm quintessential to Essex. Original architectural details including hand-carved doors, staircase banister, fireplace

  Steve Wollman Wollman Realty

  46 West Ave, Essex, CT 06426
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  /40

  $659,900

  $20K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,196 Sq Ft

  73 Long Hill Rd, Deep River, CT 06417

  Good design is all about the details and this well maintained custom Colonial is just what you have been looking for in the perfect shoreline home. Recently updated, the current owner's signature style has magically taken this charming home from ordinary to extraordinary with her colorful design. From the warm and welcoming entrance, to the well-appointed kitchen or the cozy family room centered

  Peg Mitchel Coldwell Banker Realty

  73 Long Hill Rd, Deep River, CT 06417
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  /40

  $375,000

  • 2 Beds
  • 1 Bath
  • 1,006 Sq Ft

  85 River Rd Unit E8, Essex, CT 06426

  Waterfront 2 bedroom condo located in Essex, CT at the desirable Heritage Cove association. Nicely situated in the middle of the state for convenient traveling. Close to downtown Essex. Condo features an open concept floor plan with fireplace and two bedroom. Association has a pool to enjoy and scenic views of the water. Condo is subject to probate court approval..

  Brian Hammett Hammett Real Estate

  85 River Rd Unit E8, Essex, CT 06426
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  /14

  $205,000

  • 1 Bed
  • 1 Bath
  • 454 Sq Ft

  391 Main St Unit 134, Deep River, CT 06417

  Welcome to one of Deep River's hidden treasures! Ideally located in the heart of the beautiful Connecticut River Valley, this inviting condominium with low monthly HOA of $272 offers comfortable, low-maintenance living in a well-maintained 50-unit community with easy access to Routes 9 and I-95.Enjoy the convenience of nearby Main Street, where you'll find a grocery store, liquor store, charming

  Kathy Schellens William Pitt Sotheby's Int'l

  391 Main St Unit 134, Deep River, CT 06417
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  /34

  $1,650,000

  • 2 Beds
  • 3 Baths
  • 1,880 Sq Ft

  24 Mallard Point Rd, Essex, CT 06426

  Peaceful, private and beautifully positioned above the tranquil waters of South Cove, this exceptional contemporary ranch offers spectacular water views and effortless one-floor living just minutes from historic Essex Village. More than 3,000 square feet* of light-filled living space features an open floor plan, hardwood floors and expansive windows that frame ever-changing water views and bring

  Sharon Craig William Raveis Real Estate

  24 Mallard Point Rd, Essex, CT 06426
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  /40

  $599,000

  • 3 Beds
  • 3 Baths
  • 1,846 Sq Ft

  32 Sunset Terrace, Essex, CT 06426

  Welcome home to this beautifully maintained Cape-style residence offering over 1,800 square feet of finished living space, including 1,370 square feet on the main and upper levels plus an additional 476 square feet in the finished lower level. The main floor features a newly remodeled kitchen complete with quartz countertops, stainless steel appliances, and ample cabinet space, seamlessly flowing

  Chris Torrez RE/MAX One

  32 Sunset Terrace, Essex, CT 06426
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  /38

  $429,900

  Open Sun 12PM - 1:30PM $20K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,114 Sq Ft

  58 Union St, Deep River, CT 06417

  Welcome to 58 Union Street in the heart of charming Deep River! Just moments from the vibrant downtown, this beautifully updated home offers the perfect blend of character, comfort, and modern efficiency. Inside, you'll find hardwood floors, timeless architectural charm, and a thoughtfully renovated interior featuring a remodeled kitchen with all-new stainless-steel appliances, an updated

  Gigi Giordano Taylor Compass Connecticut, LLC

  58 Union St, Deep River, CT 06417
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  /40

  $829,000

  • 4 Beds
  • 6 Baths
  • 7,309 Sq Ft

  33 Deep River Rd, Centerbrook, CT 06409

  Incredible investment opportunity. Mixed use/flex space including two existing apartments. Historic building that has had multiple uses including an antique book store and once a brush factory. Many updates in recent years with a variety of potential uses. Level .74 acre lot, gravel parking lot, great visibility and signage. There are two apartments and multiple office/flex spaces. The property

  Susan Malan William Pitt Sotheby's Int'l

  33 Deep River Rd, Centerbrook, CT 06409
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  /15

  $995,000

  • Land
  • 1.02 Acres
  • $975,490 per Acre

  41B River Rd, Essex, CT 06426

  Extremely rare! Peaceful, tranquil waterfront lot available. This special location is on Falls River Cove with a shared dock and consists of 1+ acres ready for new construction. View restrictions in place. Please see declaration of restrictions, covenants and easements in the attached. The lot is not visible from the road; shown by appointment only.

  Susan Malan William Pitt Sotheby's Int'l

  41B River Rd, Essex, CT 06426
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  /37

  $895,000

  $100K PRICE INCREASE

  • 3 Baths
  • 4,544 Sq Ft

  3 Essex Square, Essex, CT 06426

  A rare and unparalleled opportunity to acquire an iconic c.1900 property set atop a gentle rise at the head of Main Street in historic Essex Village. This substantial, professionally maintained building is comprised of two legal condominium units, and offers unmatched flexibility with its APPROVED MIXED RETAIL/OFFICE/RESIDENTIAL USE status. Potential to create your own custom Essex village

  Rick Weiner William Pitt Sotheby's Int'l

  3 Essex Square, Essex, CT 06426
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  /40

  $7,889,000

  • 3 Beds
  • 5 Baths
  • 4,664 Sq Ft

  175 River Rd, Essex, CT 06426

  Set along one of Essex's most coveted stretches of River Road, this exceptional waterfront estate offers a rare blend of understated elegance, privacy, and Connecticut River waterfront. Privately sited on nearly three acres, the property enjoys a serene, tucked-away feel while remaining just minutes from the heart of Essex Village. Custom-built and thoughtfully designed by its original owner, the

  Susan Malan William Pitt Sotheby's Int'l

  175 River Rd, Essex, CT 06426
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  /33

  $499,900

  • 3 Beds
  • 1.5 Baths
  • 1,860 Sq Ft

  18 Partridge Ln, Essex, CT 06426

  Set on a peaceful cul-de-sac, this inviting 3-bedroom home offers 1,860 square feet of living space, hardwood floors, and a flexible, open layout. The main level features a spacious kitchen that flows seamlessly into the dining area and living room, creating a bright and connected space for everyday living and entertaining. The living room features a gas fireplace with built-ins, adding warmth

  Mikell Foggitt Margaret Bennett Realty

  18 Partridge Ln, Essex, CT 06426
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  /39

  $850,000

  • 4 Beds
  • 2.5 Baths
  • 2,756 Sq Ft

  78 Meadow Woods Rd, Deep River, CT 06417

  An oasis of privacy, peace and elegance awaits you here at one of Deep River's most desirable locations. Spring and summer song birds serenade you from the refurbished deck nestled among mature trees covering 3.21 acres of gently sloping land. As you enter through colorful gardens professionally landscaped for minimal maintenance, you'll be greeted by rich Brazilian Cherry hardwood floors that

  Gerard Sullivan Coldwell Banker Realty

  78 Meadow Woods Rd, Deep River, CT 06417
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  /28

  $496,900

  • 3 Beds
  • 2 Baths
  • 2,103 Sq Ft

  11 Castle View Dr, Chester, CT 06412

  Offered for sale for the very first time, this lovingly cared-for home is a rare opportunity in the welcoming Castle View Drive neighborhood, just moments from Chester Center. While the manicured lawn, mature gardens, and meticulous exterior maintenance create an excellent first impression, this home is much larger than it appears from the front elevation. Step inside and discover a spacious

  Cortney Emshwiller-Swokla Coldwell Banker Realty

  11 Castle View Dr, Chester, CT 06412
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  /2

  $2,200,000

  • Land
  • 30 Acres
  • $73,333 per Acre

  134 Meadow Woods Rd, Deep River, CT 06417

  Rare opportunity to acquire approximately 30 acres in one of Deep River's most desirable locations. This exceptional property presents a unique residential development opportunity combining privacy, natural beauty, existing improvements, and future potential. The property includes an existing Saltbox style residence and offers subdivision potential for approximately 5-7 residential lots, subject

  Jennifer Gurnell William Raveis Real Estate

  134 Meadow Woods Rd, Deep River, CT 06417
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  /9

  $229,000

  Open Sun 12PM - 2PM

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft

  77 Scenic View Dr Unit 17, Deep River, CT 06417

  Single level living in updated condo in Deep River! Peaceful location provides serenity, yet close to vibrant town center with everything you need including restaurants, shops, groceries, pharmacy and more! Close to Route 9 for convenience. Why rent when you can own in Deep River?!

  Joe Simmons Coldwell Banker Realty

  77 Scenic View Dr Unit 17, Deep River, CT 06417
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  /38

  $3,150,000

  • 4 Beds
  • 6 Baths
  • 4,926 Sq Ft

  288 Middlesex Ave, Chester, CT 06412

  Set along a coveted stretch of the Connecticut River, this stunning, turnkey waterfront compound offers a rare convergence of privacy, protected views, and deep water access-just over one mile from the heart of Chester Village. Encompassing 2.65 acres with 285 feet of direct river frontage, the property unfolds as a true waterfront retreat. Manicured grounds lead seamlessly from the residence and

  Nancy Mesham Coldwell Banker Realty

  288 Middlesex Ave, Chester, CT 06412
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  /40

  $1,199,999

  • 9 Beds
  • 9 Baths
  • 4,982 Sq Ft

  209 Main St, Deep River, CT 06417

  Quintessential New England living in the heart of Deep River. This exceptional Antique home was masterfully expanded in 1987, seamlessly doubling its size while capturing the essence of a classic Colonial-offering the space, flow, and functionality for today's living. The home's design celebrates period-inspired architecture including custom-milled woodwork, wide-plank pumpkin pine floors, and

  Diane Devries William Pitt Sotheby's Int'l

  209 Main St, Deep River, CT 06417
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  /40

  $1,895,000

  • 4 Beds
  • 3 Baths
  • 3,023 Sq Ft

  5 Hemlock Dr, Essex, CT 06426

  Every home tells a story, and 5 Hemlock Drive's is one of transformation. Perched high above South Cove with sweeping views across the Connecticut River to Essex Village beyond, this striking post-and-beam Acorn Deck House has been reimagined from top to bottom by its owner, a local architect, with no detail overlooked and no expense spared. Vaulted ceilings, walls of glass and skylights flood

  John Campbell Compass Connecticut, LLC

  5 Hemlock Dr, Essex, CT 06426
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  /40

  $1,065,000

  • 3 Beds
  • 2 Baths
  • 2,102 Sq Ft

  106 Meadow Woods Rd, Deep River, CT 06417

  Privately set on over three picturesque acres in Deep River, just moments from the Essex town line, this extraordinary custom home is the result of an exceptional architectural transformation, blending timeless New England character with thoughtful, high-end design. Enjoy a peaceful, private setting while being just minutes from the charming village centers of Deep River and Essex, with their

  Gigi Giordano Taylor Compass Connecticut, LLC

  106 Meadow Woods Rd, Deep River, CT 06417
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  /40

  $3,595,000

  • 5 Beds
  • 4 Baths
  • 3,769 Sq Ft

  10 Scholes Ln, Essex, CT 06426

  Steeped in history and prominently positioned in the heart of Essex Village, the distinguished "Frederick Scholes House" (circa 1890) offers a rare opportunity to own a landmark waterfront estate. Cherished by its current owners for 49 years and nestled on a quiet lane along picturesque Middle Cove, just off the Connecticut River, this property seamlessly blends timeless character with refined

  Susan Malan William Pitt Sotheby's Int'l

  10 Scholes Ln, Essex, CT 06426
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  /35

  $499,000

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft

  135 Middlesex Ave, Chester, CT 06412

  NEW PRICE!! Beautiful view from this WATERFRONT home on Chester Cove! Steps to fishing or kayaking just out your door. Enjoy watching the wildlife from the 20x10 deck directly off the kitchen/dining/living rooms. Wonderful light enters through the abundant windows on the first floor with its open floor plan, kitchen with granite, newer appliances and a window over the kitchen sink you won't want

  Lisa Genovali Re/Max Valley Shore

  135 Middlesex Ave, Chester, CT 06412
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  /40

  $489,999

  $25K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,608 Sq Ft

  89 Book Hill Rd, Essex, CT 06426

  Welcome to 89 Book Hill Road in the heart of Essex Village. This beautifully updated Cape offers a perfect blend of classic New England charm and modern comfort. Set on a private lot surrounded by mature trees, the home features a spacious and light-filled layout with hardwood floors, two fireplaces, and a flexible floor plan. The kitchen has been tastefully updated with modern finishes, flowing

  Gary Crawford RE/MAX RISE

  89 Book Hill Rd, Essex, CT 06426
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  /39

  $3,950,000

  • 5 Beds
  • 5.5 Baths
  • 5,557 Sq Ft

  323 River Rd, Deep River, CT 06417

  Here is your opportunity to own an extraordinary Connecticut River waterfront estate complete with a deep-water dock! This exceptional 5 bedroom, 5.5 bath residence offers unparalleled privacy and stunning panaromic views across protected conservation land, creating a setting of remarkable beauty and tranquility. Thoughtfully designed to embrace its spectacular surroundings, every room is filled

  Margaret Muir William Pitt Sotheby's Int'l

  323 River Rd, Deep River, CT 06417
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  /27

  $430,000

  • 2 Beds
  • 2 Baths
  • 810 Sq Ft

  52 Pond Meadow Rd, Ivoryton, CT 06442

  Welcome home to your own private cottage style farm house in the heart of picturesque Ivoryton - where timeless New England charm meets modern comfort. This beautifully maintained home offers the perfect blend of character, quality, and opportunity, making it an ideal year-round residence, weekend retreat, or investment property. Situated in one of Connecticut's most sought-after shoreline

  Noah Gates Real Broker CT, LLC

  52 Pond Meadow Rd, Ivoryton, CT 06442
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  /31

  $820,000

  $55K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,554 Sq Ft

  18 Maple Ave, Essex, CT 06426

  Private, move in ready Essex Village ranch on a large level landscaped lot, set back from the road. Lots of privacy. Walk to restaurants, shops, library, parks and CT River. Remodeled 36x10 sunroom / dining area with a wall of sliders. Finished lower lever Family room, guest room and full bathroom. 690 square feet not included in the square feet. Total of 1914 sqf. Oversized shed for a handyman

  Mark Reyher Reyher Real Estate

  18 Maple Ave, Essex, CT 06426
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  /14

  $1,750,000

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,500 Sq Ft

  Lot 1 - 160 Saybrook Rd, Essex, CT 06426

  TO BE BUILT, imagine your beautiful NEW construction home here across the street from coveted south cove in Essex, Connecticut. Just minutes away from downtown Essex. Customization is possible. The striking roofline with multiple gables, elegant dormers, and a signature cupola creates architectural presence, while crisp white trim and standing-seam metal roof accents provide clean, sophisticated

  Robyn Letourneau Berkshire Hathaway NE Prop.

  Lot 1 - 160 Saybrook Rd, Essex, CT 06426
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  /29

  $449,999

  $20K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,252 Sq Ft

  46 Main St, Essex, CT 06426

  Discover the perfect blend of income potential and small-town charm with this centrally located two-unit property. Ideal for investors or owner-occupants seeking rental income, this well-maintained home offers flexibility and walkable convenience in the heart of Centerbrook. First Floor - Private entrance with direct access from the parking area. Freshly painted and flooded with natural light,

  Tracy Lenz William Pitt Sotheby's Int'l

  46 Main St, Essex, CT 06426
• 

  

  /39

  $759,900

  • 3 Beds
  • 3 Baths
  • 2,456 Sq Ft

  45 Main St, Essex, CT 06426

  Wonderful waterfront antique home on 1.6 acres. The Parker Bull House, circa 1754 located in Ivoryton overlooking the Falls River, this gracious home is a unique blend of original antique features with updated modern amenities. The large sunlit kitchen has granite countertops and stainless-steel appliances, hardwood floors, and is adjacent to a spacious pantry/laundry room, heated sunroom, and a

  Susan Malan William Pitt Sotheby's Int'l

  45 Main St, Essex, CT 06426

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