Homes for Sale near Valley Regional High School

• 

  

  

  /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

  (860) 579-1057

  87 Main St, Deep River, CT 06417
• 

  Explore Valley Regional High School

• 

  

  

  /33

  $185,000

  • 2 Beds
  • 1 Bath
  • 832 Sq Ft

  15 Sunset Terrace Unit 11, Essex, CT 06426

  Location, Location! Available immediately to investors and primary owner-occupants. Perched high atop Sunset Terrace in Essex, the Stone Pit Hill condo complex offers only 12 units in a private setting. Enjoy a high walk-score lifestyle with nearby Sunset Pond for summer and winter fun, Essex Steam Train, Grove Street Park with playground, tennis courts, and walking paths. Stroll to charming

  

  Al Chiarito

  Chiarito Real Estate LLC

  (860) 909-8521

  15 Sunset Terrace Unit 11, Essex, CT 06426
• 

  

  

  /40

  $1,850,000

  • 4 Beds
  • 2.5 Baths
  • 2,676 Sq Ft

  9 Essex Hills Dr, Essex, CT 06426

  Exquisitely updated & remodeled Essex home on the cusp of South Cove with easterly views. This fabulous home has been completely transformed into something very special! From the eat-in kitchen with breakfast bar & smart design to the living room & family room both with wood burning fireplaces & sleeping quarter, no detail has been overlooked. The outdoor space has been completely revived with

  

  Kevin Geysen

  William Pitt Sotheby's Int'l

  (860) 419-4926

  9 Essex Hills Dr, Essex, CT 06426
• 

  

  

  /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

  (860) 288-9987

  130 Mares Hill Rd, Essex, CT 06442
• 

  

  

  /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
• 

  

  /35

  $1,250,000 Open Sat 12PM - 3PM

  • 3 Beds
  • 3.5 Baths
  • 2,467 Sq Ft

  45 Falls River Dr, Ivoryton, CT 06442

  Embrace the waterfront lifestyle at 45 Falls River Drive, located on a designated scenic road in the charming village of Ivoryton within the Town of Essex. Launch your kayak from your own backyard, sip your morning coffee on the dock, and unwind on the expansive deck while herons glide by. Adjacent to the protected Falls River Preserve, this property offers access to scenic trails, kayaking, and

  Nora Porcelli William Raveis Real Estate

  45 Falls River Dr, Ivoryton, CT 06442
• 

  

  /3

  $1,100,000 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,700 Sq Ft

  Lot 2 - 160 Saybrook Rd, Essex, CT 06426

  Traditional New England Colonial style meets high efficiency, elevated luxurious, and BRAND NEW!! This is your chance to embrace new construction situated in the highly sought after town of Essex. This Brand new house has WATER VIEWS overlooking the Essex South Cove. Imagine your New England coastal dreams, fourth of July parties on the patio and incredible sunrises/ Sunsets. Lets plan your

  Robyn Letourneau Berkshire Hathaway NE Prop.

  Lot 2 - 160 Saybrook Rd, Essex, CT 06426
• 

  

  /36

  $1,300,000

  • 4 Beds
  • 4 Baths
  • 3,036 Sq Ft

  11 N Main St, Essex, CT 06426

  Welcome to the reimagined John Miner House on North Main Street in the charming Connecticut River Valley Village of Essex. Originally built in 1880 as a residence and tailor shop, this historic property has evolved over the years into a unique investment and lifestyle opportunity. Ideally located in the Heart of the Village, you'll enjoy a short stroll to the Connecticut River, marinas, quaint

  Philip Warner William Pitt Sotheby's Int'l

  11 N Main St, Essex, CT 06426
• 

  

  /4

  $1,400,000 New Construction

  • 5 Beds
  • 3.5 Baths
  • 3,400 Sq Ft

  Lot 3 - 160 Saybrook Rd, Essex, CT 06426

  TO BE BUILT subject to final approval, imagine your beautiful new home here across the street from coveted south cove in Essex, Connecticut. Customization is possible, and initial design is just one option! This brand new home features traditional new england charm with modern amenities. Hardwood floors, beautiful natural light, granite/quartz countertops, soft close cabinetry and your choice of

  Robyn Letourneau Berkshire Hathaway NE Prop.

  Lot 3 - 160 Saybrook Rd, Essex, CT 06426
• 

  

  /39

  $1,849,000

  • 4 Beds
  • 3.5 Baths
  • 3,724 Sq Ft

  101 N Main St, Essex, CT 06426

  Nestled in the heart of Essex Village along one of its most picturesque streets, this iconic c.1818 home welcomes you with a charming wraparound covered front porch, an inviting place to sit and relax. Inside, you'll find a perfect blend of timeless character and thoughtful modern updates, creating a home is both beautiful and comfortable. At its heart is a custom chef's kitchen featuring solid

  Jodi Strycharz William Pitt Sotheby's Int'l

  101 N Main St, Essex, CT 06426
• 

  

  /40

  $1,199,999

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

  209 Main St, Deep River, CT 06417

  Experience the timeless beauty of New England living! This meticulously restored 1854 Colonial blends historic charm with modern comfort in the heart of Deep River. Every detail has been thoughtfully preserved or reimagined-from the gleaming pumpkin pine wide-plank floors and custom-milled woodwork to carefully selected reproduction hardware that speaks to its heritage. Six fireplaces grace the

  Diane Devries William Pitt Sotheby's Int'l

  209 Main St, Deep River, CT 06417
• 

  

  /31

  $454,900

  • 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
• 

  

  /10

  $365,000

  • 2 Beds
  • 1 Bath
  • 912 Sq Ft

  8 Prospect Hill, Deep River, CT 06417

  This home possesses structural integrity and endless potential. Many updates including new boiler in 2024, roof, garage doors front and back, new appliances include sink and countertop. Originally had a 3rd bedroom and wall could be put back up if interested in adding back. Short walking distance to charming downtown Deep River and 3/4 mile to the gorgeous CT river. Only 2 hours from NYC. Whether

  Craig Milton Re/Max Valley Shore

  8 Prospect Hill, Deep River, CT 06417
• 

  

  /21

  $750,000

  • 2 Beds
  • 2 Baths
  • 1,179 Sq Ft

  1 Benson Ln, Essex, CT 06426

  Meticulously maintained and thoughtfully curated, this one-of-a-kind post-and-beam barn in the Essex Village district offers a rare blend of historic character and modern comfort. Showcasing wide plank floors, rich natural textures, and awe-inspiring architectural details throughout, this home delivers warmth and style in every space. The open-concept main living area is anchored by a striking

  Katherine Bergeron Real Broker CT, LLC

  1 Benson Ln, Essex, CT 06426
• 

  

  /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
• 

  

  /32

  $724,900

  • 2 Beds
  • 2 Baths
  • 1,589 Sq Ft

  14 Essex Glen Dr Unit 4, Essex, CT 06426

  Tucked within an intimate enclave of just 26 thoughtfully designed homes in Essex -- often celebrated as "The Best Small Town in America" -- this one-owner residence, built in 2018, offers a refined yet effortless lifestyle. A free-standing design provides privacy, while the community handles lawn care and snow removal, making everyday living refreshingly simple. Low utility costs and favorable

  Susan Malan William Pitt Sotheby's Int'l

  14 Essex Glen Dr Unit 4, Essex, CT 06426
• 

  

  /39

  $625,000

  • 4 Beds
  • 2.5 Baths
  • 2,550 Sq Ft

  22 Ebony Ln, Ivoryton, CT 06442

  Welcome to this beautifully maintained Colonial at 22 Ebony Lane in Ivoryton, offering a thoughtful layout, quality updates, and comfortable living spaces ideal for today's lifestyle. A welcoming foyer with a sitting area sets the tone as you enter the home, leading into a warm and inviting interior enhanced by new Harvey windows, a new roof, and a whole-house generator for comfort and peace of

  Gigi Giordano Taylor Compass Connecticut, LLC

  22 Ebony Ln, Ivoryton, CT 06442
• 

  /2

  $282,225

  • 2 Beds
  • 2 Baths
  • 1,344 Sq Ft

  3 Kirtland Ave, Chester, CT 06412

  REO Occupied - NO ACCESS OR VIEWINGS of this property - no interior photos. Please DO NOT DISTURB the occupant. Built in 1974, this one level home offers approximately 1344 finished square feet, two bedrooms and two full baths, fireplace, unfinished basement and attached one car garage. This home sits on an approximate 14810 sqft lot. "As is" cash only sale with no contingencies or inspections.

  Sherry Price Realhome Services & Solutions

  3 Kirtland Ave, Chester, CT 06412
• 

  

  /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
• 

  

  /34

  $525,000

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

  135 Middlesex Ave, Chester, CT 06412

  Coming in a few short days.... This WATERFRONT home on Chester Cove has the most spectacular views! Steps to fishing or kayaking! Enjoy watching the wildlife from the 20x10 deck just off the kitchen/dining/living rooms. Wonderful light enters through the numerous windows on the first floor with its open floor plan, full bath and sliders to the deck. On the second floor there are three bedrooms

  Lisa Genovali Re/Max Valley Shore

  135 Middlesex Ave, Chester, CT 06412
• 

  

  /38

  $775,000

  • 2 Beds
  • 2 Baths
  • 1,600 Sq Ft

  10 Cove Hill Rd, Essex, CT 06426

  Private 2.2 acre property with an in-ground pool just minutes from Essex Village. Set on a lightly wooded lot, this 2 bedroom, 2 full bath home offers a combination of privacy and convenience near the shops, restaurants, and marinas in the village. Inside you will find a spacious kitchen and great room with vaulted ceilings, island seating, and plenty of room for a dining table. A formal living

  Kara Bell J.M. REALTY

  10 Cove Hill Rd, Essex, CT 06426
• 

  

  /23

  $465,000

  • 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
• 

  

  /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
• 

  

  /40

  $823,999

  • 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
• 

  

  /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
• 

  

  /39

  $799,900

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

  45 Main St, Essex, CT 06426

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

  Susan Malan William Pitt Sotheby's Int'l

  45 Main St, Essex, CT 06426
• 

  

  /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
• 

  

  /11

  $238,500

  • Land
  • 1.5 Acres
  • $159,000 per Acre

  11 Kings Hwy, Chester, CT 06412

  1.5+ acre lot, clear cut, open, sunny, with a clean air flow. SE facing with 4-mile view down CT River Valley to Deep River, and Lyme Hills; seasonal partial view of Gillette Castle in Hadlyme. Excellent solar, passive or active potential; 220 volts available at street. Ready to build with approvals in place for 3-bedroom septic, town building department, with Connecticut Water Co. supply line

  Rachel Welch William Raveis Real Estate

  11 Kings Hwy, Chester, CT 06412
• 

  

  /40

  $2,800,000

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

  88 Main St, Ivoryton, CT 06442

  Move into this elegantly designed, meticulously restored estate in the nationally registered historic village of Ivoryton in the town of Essex. Built by the prominent Essex industrialist, Samuel Comstock, the 5,234 sq. ft. property on 1.86 acres offers history and grandeur to those seeking privacy and tasteful opulence. Preserved in the same family for five generations and recently completely

  Kirsten Adams William Pitt Sotheby's Int'l

  88 Main St, Ivoryton, CT 06442
• 

  

  /40

  $499,999

  • 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

  Tyler Lynch RE/MAX RISE

  89 Book Hill Rd, Essex, CT 06426
• 

  

  /24

  $1,700,000

  • 13 Beds
  • 8 Baths
  • 7,641 Sq Ft

  170 Main St, Deep River, CT 06417

  Exciting investment package in the heart of downtown Deep River! This rare offering includes two nicely renovated multifamily/mixed-use buildings plus a well-established laundromat business, all conveyed together in one sale. 170 Main Street sits on a beautiful corner lot and features a turnkey 5-unit multifamily property with a unit mix of (2) two-bedroom units and (3) one-bedroom units. All

  Amanda Sheehan Oxford Realty

  170 Main St, Deep River, CT 06417
• 

  

  /39

  $799,900

  • 3 Beds
  • 3 Baths
  • 2,407 Sq Ft

  112 Main St, Centerbrook, CT 06409

  Nestled on a prime 0.5-acre corner lot in the heart of Centerbrook, 112 Main Street is a meticulously maintained 3-bedroom home that perfectly blends classic charm with serious modern utility. The residence has been extensively updated, featuring an exterior professionally painted in August 2025 with a three-year guarantee and a refreshed kitchen boasting new countertops and a functional kitchen

  Adam Zak Century 21 Classic Homes

  112 Main St, Centerbrook, CT 06409
• 

  

  /39

  $775,000

  • 3 Beds
  • 3.5 Baths
  • 3,476 Sq Ft

  74 Bushy Hill Rd, Ivoryton, CT 06442

  Tucked away on 2.53 picturesque acres in Ivoryton, this inviting Cape Cod offers the perfect blend of privacy, space, and natural beauty. With 3 bedrooms, 3 baths, and over 3,400 square feet, the home is surrounded by gardens, beautiful meadow, a tranquil pond, and plenty of space to simply enjoy the peaceful setting. Entertain or unwind on the expansive patio and deck while taking in the serene

  Susan Malan William Pitt Sotheby's Int'l

  74 Bushy Hill Rd, Ivoryton, CT 06442
• 

  

  /37

  $2,100,000

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

  163 Main St, Deep River, CT 06417

  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

  163 Main St, Deep River, CT 06417
• 

  

  /37

  $399,900

  • 2 Beds
  • 2.5 Baths
  • 1,384 Sq Ft

  65 Main St Unit 24, Essex, CT 06426

  Enjoy easy living just steps from the charm of Ivoryton Village in this beautifully maintained 2-bedroom home, 2 full and 1 half bath, offering 1,384 sq ft of bright, inviting space. The main level features an open and airy layout, highlighted by a remodeled eat-in kitchen with sliders leading to a spacious deck, perfect for entertaining or relaxing outdoors. Hardwood flooring flows throughout,

  Craig Milton Re/Max Valley Shore

  65 Main St Unit 24, Essex, CT 06426
• 

  

  /29

  $469,900

  • 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
• 

  

  /40

  $597,900

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

  7 Mitchel Terrace, Ivoryton, CT 06442

  Tucked into a peaceful woodland setting near the scenic Falls River Preserve, this striking contemporary home offers a seamless blend of nature, light, and modern design. Surrounded by mature trees, this tranquil property delivers a sense of privacy while remaining close to outdoor recreation and everyday conveniences. Inside, soaring cathedral ceilings & an open-concept first floor create an

  Lisa Genovali Re/Max Valley Shore

  7 Mitchel Terrace, Ivoryton, CT 06442
• 

  

  /28

  $815,000

  • 2 Beds
  • 1.5 Baths
  • 961 Sq Ft

  39 Prospect St, Essex, CT 06426

  Hilltop Cottage c.1900 The Perfect pied a terre in the heart of the historic Essex CT yachting village welcomes you in each season. In spring, see your professional perennial cottage garden come alive with roses, irises, and peonies. In summer, entertain friends on your large private deck overlooking more gardens and catching the breeze off Long Island Sound. In fall, join in the village

  R. Dean Eubank William Pitt Sotheby's Int'l

  39 Prospect St, Essex, CT 06426
• 

  

  /32

  $4,300,000

  • 3 Beds
  • 3.5 Baths
  • 4,383 Sq Ft

  7 Hanna Ln, Essex, CT 06426

  Fresh Update for a Classic Connecticut Home - Discover a beautifully restored 1955 waterfront classic. Stunning panoramic water views, privacy and walk-to-town convenience. Ascend to the family room, crowned with cathedral ceilings and expansive windows that invite the breathtaking views of the Connecticut River. A Danish gas fireplace adds a touch of sophistication, creating a cozy yet chic

  Colette Harron William Pitt Sotheby's Int'l

  7 Hanna Ln, Essex, CT 06426
• 

  

  /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

Showing Results 1 - 40, Page 1 of 2