Homes for Sale near Valley Regional High School

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  /37

  $1,350,000

  • 7 Beds
  • 6 Baths
  • 3,787 Sq Ft

  87 Main St, Deep River, CT 06417

  VC Property Group is proud to present a two-parcel assemblage in Deep River, Connecticut, offering stabilized mixed-use income with residential value and land optionality. The assemblage includes: 87 Main Street - a parcel improved with: a Newer Construction Single Family Residence and a 5-unit mixed-use building (four residential apartments and one retail unit) 55 Prospect Street - a contiguous

  

  Anthony Velez

  VC Property Group, LLC

  87 Main St, Deep River, CT 06417
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  Explore Valley Regional High School

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  /40

  $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
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  /40

  $1,795,000

  $100K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 5,610 Sq Ft

  108 Westbrook Rd, Essex, CT 06426

  Amazing custom built Nantucket style Cape situated on sprawling grounds, terraced high above a picturesque great yard & overseen by natural highlands. The setting is nothing but breathtaking! Inclusive is an inground pool engulfed by the primary hardscape which walks-out from the lower level & is situated high above the great yard. A magnificent carriage house featuring a 4 bay garage &

  

  Kevin Geysen

  William Pitt Sotheby's Int'l

  108 Westbrook Rd, Essex, CT 06426
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  /40

  $949,000

  • 6 Beds
  • 4.5 Baths
  • 2,772 Sq Ft

  7 Orchard Heights Rd, Essex, CT 06426

  Set on a picturesque street in the charming town of Essex, 7 Orchard Heights Road offers classic New England living with spacious interiors and inviting outdoor spaces designed for everyday comfort and entertaining. This well maintained Colonial features a generously sized kitchen with ample cabinetry and workspace, flowing seamlessly into the main living areas for easy gatherings and relaxed

  

  Tammy Tinnerello

  William Pitt Sotheby's Int'l

  7 Orchard Heights Rd, Essex, CT 06426
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  /37

  $1,190,000

  • 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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  /40

  $525,000

  • 3 Beds
  • 3 Baths
  • 2,971 Sq Ft

  12 Meadow Ln, Chester, CT 06412

  Set at the end of a quiet dead-end road, this three-bedroom ranch offers the ease of one-floor living, exceptional privacy, and over four acres of peaceful surroundings in Chester. Inside, two inviting wood stoves create warm, comfortable gathering spaces, while a newer roof adds peace of mind. Step outside to a covered deck that flows seamlessly to an open deck overlooking the private backyard

  

  Kelly Puorro

  Puorro Realty Group

  12 Meadow Ln, Chester, CT 06412
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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 contemporary home features 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 en-suite bath,

  

  Kiki Sydnor

  Choice Realty

  130 Mares Hill Rd, Essex, CT 06442
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  /40

  $825,000

  • 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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  /24

  $299,900

  • 1 Bed
  • 1 Bath
  • 1,034 Sq Ft

  90 Water St, Chester, CT 06412

  Rare waterfront opportunity! Nestled directly on the water, 90 Water St is a 1-bathroom Ranch currently configured as a 1-bedroom, but offering a spacious layout that easily converts to a 2-bedroom home. Built in 1950, the property provides a fantastic foundational footprint. It features a large 13'6" x 20'10" living room and a versatile 10'3" x 20'10" family room-the ideal space to partition

  Luke Florian SSG Real Estate LLC

  90 Water St, Chester, CT 06412
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  /29

  $324,900

  • 3 Beds
  • 1 Bath
  • 1,217 Sq Ft

  92 Water St, Chester, CT 06412

  Welcome to 92 Water St, a charming 1927 two-story Colonial offering a rare opportunity to own waterfront property in picturesque Chester, CT! This 3-bedroom, 1-bathroom home is perfectly situated right on the water, offering tranquil riverfront views and an unbeatable location just a short, scenic stroll from downtown Chester's highly desirable boutiques, art galleries, and acclaimed dining.

  Luke Florian SSG Real Estate LLC

  92 Water St, Chester, CT 06412
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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

  $399,000

  Coming Soon

  • 2 Beds
  • 1 Bath
  • 1,817 Sq Ft

  79 River St, Deep River, CT 06417

  Move right into this Deep River home just moments from the Connecticut River and the charming village and town center. Since purchasing the property, the current owner has completed numerous valuable improvements, including a brand-new roof, new furnace, new oil tank, a tastefully remodeled kitchen, and an updated full bathroom. The main level offers inviting living spaces that blend character

  Gigi Giordano Taylor Compass Connecticut, LLC

  79 River St, Deep River, CT 06417
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  /40

  $945,000

  $50K 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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  /31

  $449,500

  $5K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,122 Sq Ft

  85 River Rd Unit G2, Essex, CT 06426

  Well appointed two story, two bedroom townhouse located in the waterfront community of Heritage Cove. An updated kitchen, primary bath, neutral color palette for the walls, trim and flooring makes this home truly move in ready. Conveniently located for on street parking and the units assigned carport. Just a stroll across the lawn to enjoy the pool and community fire table add to this unique

  Patrick Kilty William Raveis Real Estate

  85 River Rd Unit G2, Essex, CT 06426
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  /31

  $599,900

  • 2 Beds
  • 1 Bath
  • 980 Sq Ft

  17 Grandview Terrace, Essex, CT 06426

  Village living at its best! Lovely inviting Ranch offering Living Rm. with cozy Fireplace, 2BR, charming Kitchen, HW floors, Breezeway/Sun rm. and attached garage. Fun and adventure is just a short walk to nearby Library, Playground, Tennis Courts, Pond, Dog Park, Town Center Shops, and Dining. Furnace 10yr, HW heater 5yr old. Roof 2025. Dining preferences possible in LR nook or Sun Rm. Come

  Diane Beckwith Popolizio William Raveis Real Estate

  17 Grandview Terrace, Essex, CT 06426
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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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  /15

  $212,000

  • 1 Bed
  • 1 Bath
  • 727 Sq Ft

  92 Main St Unit 107, Deep River, CT 06417

  Step into a loft-style townhouse in the historic Piano Works building that blends vintage charm with modern living. With its own private entrance and location in a 4-unit outbuilding, this home offers peace and privacy-no upstairs or downstairs neighbors to worry about! With its impressive 9-foot-plus ceilings and exposed ductwork, this home exudes a chic, industrial vibe. Right outside your

  Anna Kilty Compass Connecticut, LLC

  92 Main St Unit 107, Deep River, CT 06417
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  /37

  $2,100,000

  • 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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  /9

  $450,000

  • 2 Beds
  • 1 Bath
  • 1,006 Sq Ft

  85 River Rd Unit M4, Essex, CT 06426

  River views from your living room, primary bedroom and patio. Meticulously maintained two bedroom ground floor unit. Brick fireplace with lovely wood mantelpiece surround. Kitchen updates include granite countertops, newer appliances and open plan with large island. Bathroom entry from primary bedroom has larger door and level shower handicap access. Patio with brick and flagstone has water view.

  Louisa Ketron Berkshire Hathaway NE Prop.

  85 River Rd Unit M4, Essex, CT 06426
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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

  $679,900

  • 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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  /30

  $299,900

  • 2 Beds
  • 1 Bath
  • 912 Sq Ft

  8 Phelps Ln, Deep River, CT 06417

  Welcome to 8 Phelps Lane, a wonderful opportunity in Deep River's sought after Tri-Town and located in the Landing Neighborhood. With a new roof and new siding already completed, this home offers peace of mind and a solid foundation for future improvements. Inside, the open concept living room, dining area, and kitchen create a bright, functional space ideal for everyday living and entertaining.

  kathleen mullins Real Broker CT, LLC

  8 Phelps Ln, Deep River, CT 06417
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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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  /23

  $455,000

  $20K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,375 Sq Ft

  85 River Rd Unit B7, Essex, CT 06426

  Welcome to Heritage Cove and a rare opportunity. Unit B-7 in the desirable B building is on the market. Three story, three-bedroom townhouse has been owned by the same family since the earliest days of Heritage. Bring your decor ideas to this exceptionally located property. It is very unusual to find a legitimate three-bedroom condominium. This unit offers sweeping views of North Cove and the

  Patrick Kilty William Raveis Real Estate

  85 River Rd Unit B7, Essex, CT 06426
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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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  /40

  $779,000

  $45K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,433 Sq Ft

  257 W Elm St, Deep River, CT 06417

  Tucked away on 4.4 acres of rolling countryside with direct frontage on a tranquil reservoir, this custom-built farmhouse Cape is a rare find. Thoughtfully constructed in 2002 and lovingly maintained by its original owner, the home offers three bedrooms, two and a half baths, and a first-floor primary suite with a generous walk-in closet and en suite bath. Hardwood floors, a wood-burning

  John Izzo William Raveis Real Estate

  257 W Elm St, Deep River, CT 06417
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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

  $795,000

  • 3 Baths
  • 4,260 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

  $899,900

  $50K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,782 Sq Ft

  16 Glen Grove Rd, Deep River, CT 06417

  16 Glen Grove Road....a stunning custom built 2023 Colonial privately set on 4.53 acres in desirable Deep River. Tucked well off the road and surrounded by beautiful stone walls, this property offers exceptional privacy and endless possibilities to enjoy the outdoors, from garden areas & gorgeous rock walls, to creating your own walking trails throughout the wooded landscape. Inside, you'll find

  Sara Tufano Real Broker CT, LLC

  16 Glen Grove Rd, Deep River, CT 06417
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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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  /21

  $259,900

  • 2 Beds
  • 1.5 Baths
  • 1,232 Sq Ft

  77 Scenic View Dr Unit 4, Deep River, CT 06417

  Welcome to your new home-a spacious townhouse-style condominium nestled in a peaceful wooded setting in desirable Deep River. This 2-bedroom, 1.5-bath home offers over 1,200 square feet of comfortable living space, featuring an open and functional layout, central air, and abundant natural light throughout. Enjoy your morning coffee on the private balcony or relax on the patio overlooking the

  Cassandra Aronson Puorro Realty Group

  77 Scenic View Dr Unit 4, Deep River, CT 06417
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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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  /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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  /39

  $2,600,000

  $200K PRICE DROP

  • 5 Beds
  • 5.5 Baths
  • 5,234 Sq Ft

  88 Main St, Ivoryton, CT 06442

  Two hours from New York City. Two hours from Boston. A world away from both. Privacy is the ultimate luxury. This masterfully re-imagined 5,234 sq. ft. compound located in historic Ivoryton, a village within the town of Essex, sits behind newly established hedges on nearly two flat, manicured acres - completely turn-key, completely private. The grounds are designed for outdoor living. A 20 X 40

  Kirsten Adams William Pitt Sotheby's Int'l

  88 Main St, Ivoryton, CT 06442
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  /31

  $845,000

  $30K 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 oof 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. Oversized shed for a handyman or artist studio.

  Mark Reyher Reyher Real Estate

  18 Maple Ave, Essex, CT 06426
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  /36

  $924,000

  • 4 Beds
  • 2.5 Baths
  • 2,774 Sq Ft

  15 Pent Rd, Deep River, CT 06417

  Welcome to 15 Pent Rd in Deep River, a truly captivating property that feels like a private retreat from the moment you arrive. Set in a peaceful, natural setting surrounded by trees and scenic outdoor views, this home offers a rare blend of charm, character, and everyday comfort. This home features 4 bedrooms and a finished attic for added living space. Inside, the home is warm, bright, and full

  Nadia Martinez Ki Property Group

  15 Pent Rd, Deep River, CT 06417
• 

  

  /30

  $750,000

  • 3 Beds
  • 2.5 Baths
  • 1,979 Sq Ft

  199 Westbrook Rd, Essex, CT 06426

  Set in a serene Essex setting, this lovely contemporary home offers a rare opportunity to enjoy waterfront living on Tiffany Pond. Surrounded by beautifully landscaped grounds, the property provides a peaceful retreat with beautiful natural views in every direction. Designed for both comfort and style, the home features 3 spacious bedrooms and 2.5 baths, including a desirable first-floor primary

  Wendy Visgilio Coldwell Banker Realty

  199 Westbrook Rd, Essex, CT 06426
• 

  

  /20

  $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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