Homes for Sale near John Winthrop Middle 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

  (860) 579-1057

  87 Main St, Deep River, CT 06417
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  Explore John Winthrop Middle School

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  /40

  $1,895,000

  • 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 Gunite 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

  (860) 321-5635

  108 Westbrook Rd, Essex, CT 06426
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  /40

  $650,000

  • 3 Beds
  • 3 Baths
  • 2,752 Sq Ft

  1 Ferry Rd, Chester, CT 06412

  An extraordinary offering in one of Connecticut's most beloved river towns. Stunning sunrises over unobstructed views of Chester Creek sets the tone for this rare piece of Chester history. The Bani Denison homestead dates to 1781 and once served as Chester's first post office. Thoughtfully restored, this classic embankment Colonial with Dutch kick gambrel style roof offers modern amenities while

  

  Jennifer D'Amato

  Real Broker CT, LLC

  (860) 454-6525

  1 Ferry Rd, Chester, CT 06412
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  /21

  $850,000

  • 4 Beds
  • 2 Baths
  • 8,382 Sq Ft

  26 Ferry Rd, Chester, CT 06412

  Located in the Town of Chester, this mixed-use property presents a rare opportunity to acquire a distinctive asset in one of Connecticut's most desirable markets. As it stands, the property consists of approximately 5,000 square feet of commercial space, including one loading dock, three (3) garages, and an oversized on-site parking lot, supporting a wide range of operational and occupancy needs.

  

  Anthony Velez

  VC Property Group, LLC

  (860) 579-1600

  26 Ferry Rd, Chester, CT 06412
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  /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
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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

  (860) 288-9987

  130 Mares Hill Rd, Essex, CT 06442
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  /32

  $10,000,000

  • 5 Beds
  • 8 Baths
  • 7,021 Sq Ft

  153 Ferry Rd, Lyme, CT 06439

  Welcome to 'Highover,' a 25-acre hilltop estate on the Connecticut River, voted the WSJ House of the Month nationwide. Over half a mile of waterfront, with natural barriers, ensures unmatched privacy and security. Accommodation for extended family and live-in help. Uniquely poised between New York and Boston, and less than an hour by helicopter from JFK, Logan, and Bradley. The home, designed by

  Edward Hillyer William Raveis Real Estate

  153 Ferry Rd, Lyme, CT 06439
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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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  /2

  $200,000

  • Land
  • 2.25 Acres
  • $88,889 per Acre

  43 Bokum Rd, Chester, CT 06412

  Beautiful potential building lot. Access via Private road, 2.25 acres. Undeveloped.

  Nicholas Tomanelli Coldwell Banker Realty

  43 Bokum Rd, Chester, CT 06412
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  /40

  $649,000

  • 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
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  /40

  $750,000

  • 4 Beds
  • 5 Baths
  • 2,800 Sq Ft

  16 Navy Ln, Essex, CT 06426

  Located in the heart of Essex, this special home offers the perfect blend of charm, privacy, and convenience. Just a short walk to the village yet tucked away on a quiet private street with no through traffic, the setting provides peaceful wooded surroundings while remaining close to shops, restaurants, marinas, and community events that make Essex so special. Inside, the home features a bright,

  Craig Milton Re/Max Valley Shore

  16 Navy Ln, Essex, CT 06426
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  /38

  $625,000

  • 4 Beds
  • 3 Baths
  • 2,969 Sq Ft

  112 Cedar Swamp Rd, Deep River, CT 06417

  Welcome to your dream home at 112 Cedar Swamp Road, Deep River, CT! This charming Cape Cod-style residence, originally built in 1940, has been beautifully renovated to blend classic charm with modern efficiency. With 4 spacious bedrooms and 3 full bathrooms, this home has +/- 2,900 square feet of living space, providing ample room for all your lifestyle needs. Step inside to discover a bright and

  Gigi Giordano Taylor Compass Connecticut, LLC

  112 Cedar Swamp Rd, Deep River, CT 06417
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  /40

  $375,000

  • 3 Beds
  • 1.5 Baths
  • 2,012 Sq Ft

  25 Union St, Deep River, CT 06417

  ***HIGHEST AND BEST HAS TO BE IN AT WEDNESDAY MARCH 25TH AT NOON***Charming antique home, once the church parsonage, rich with history and original character. Many period details remain, including original doors, trim, hardware, and wood floors throughout. The home features three fireplaces (two decorative) that add to its classic New England charm. Set on a lovely yard with mature plantings and

  Craig Milton Re/Max Valley Shore

  25 Union St, Deep River, CT 06417
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  /38

  $775,000

  • 3 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 3 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
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  /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
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  /24

  $475,000

  • 3 Beds
  • 1.5 Baths
  • 1,066 Sq Ft

  44 N Main St, Essex, CT 06426

  Welcome to a beautifully reimagined 1900 gem nestled right in the heart of Ivoryton Village. This charming three-bedroom, one-and-a-half-bath home has been lovingly renovated from top to bottom, blending old-world character with fresh, modern touches. Step inside and you'll immediately notice the gorgeous hardwood floors flowing through bright, airy rooms filled with natural light. The kitchen is

  Sue Gerace Central CT Realty Group

  44 N Main St, Essex, CT 06426
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  /12

  $899,900 New Construction

  • 3 Beds
  • 3.5 Baths
  • 2,164 Sq Ft

  48A Ironworks Rd, Clinton, CT 06413

  Welcome to "The River Wood" a 3-bedroom custom home, nestled on a sprawling 4.81-acre parcel boasting an impressive 624 feet of riverfront along the scenic Menunketesuck River. This architectural gem is a seamless blend of luxurious living spaces, natural beauty, and tranquil surroundings. Upon entering, you'll be greeted by an inviting double door that leads into the heart of the home. The first

  Gigi Giordano Taylor Compass Connecticut, LLC

  48A Ironworks Rd, Clinton, CT 06413
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  /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
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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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  /36

  $1,350,000

  • 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
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  /39

  $799,900 Open Sat 11AM - 1PM

  • 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
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  /19

  $689,000

  • 4 Beds
  • 2 Baths
  • 1,970 Sq Ft

  62 River St, Deep River, CT 06417

  THIS ONE OF A KIND TWO FAMILY VICTORIAN HOME IS MOVE IN CONDITION. MAKE THIS YOUR LIFESTYLE, LIVE IN ONE AND RENT THE SECOND. ALL NEW APPLIANCES, REMODELED, SEPARATE UTILITIES, IDEAL LOCATION, WALK TO TOWN, DRUG STORE, GROCERY AND RESTAURANTS.

  Mim Beardsley Houlihan Lawrence WD

  62 River St, Deep River, CT 06417
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  /30

  $299,000

  • Land
  • 4.49 Acres
  • $66,592 per Acre

  4 Laurel Ln, Clinton, CT 06413

  Build Your Dream Home on 4.49 Acres of Privacy and Natural Beauty! Nestled in a serene wooded setting, this exceptional 4.49-acre property offers a rare opportunity to bring your vision to life. With key site improvements already in place-including a driveway, existing foundation for approximately a 2,000 sq. ft. home, septic system, well, and a charming bridge crossing a gentle brook-this parcel

  Jules Gaughran - Etes William Pitt Sotheby's Int'l

  4 Laurel Ln, Clinton, CT 06413
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  /39

  $699,900

  • 4 Beds
  • 2.5 Baths
  • 2,831 Sq Ft

  85 McVeagh Rd, Westbrook, CT 06498

  Exceptional Country Living Close to Town - Westbrook, CT Discover the perfect blend of country charm and modern comfort in this beautifully maintained farmhouse colonial, ideally located in the scenic shoreline town of Westbrook. Built in 2002 by a respected local builder, this spacious home offers over 2,800 sq. ft. of living space, plus additional finished (unheated) basement area-plenty of

  Lynn Lehrman Re/Max Valley Shore

  85 McVeagh Rd, Westbrook, CT 06498
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  /40

  $375,000

  • Land
  • 11.68 Acres
  • $32,106 per Acre

  41 Bushy Hill Rd, Ivoryton, CT 06442

  Builders, Developers make note of this beautiful 11.68 Acre property. 433' road frontage on Bushy Hill Rd, underground and above ground electricity available. Surround yourself with nature and Build a Dream home on this mostly level, lightly wooded lot. Bring your horses, llamas, allowed per Zoning regulations. Can be split, able to build 2 houses with a good potential to subdivide into 3 lots.

  Carolyn DiPietro Berkshire Hathaway NE Prop.

  41 Bushy Hill Rd, Ivoryton, CT 06442
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  /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
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  /39

  $669,000 Open Sun 1PM - 3PM

  • 2 Beds
  • 2 Baths
  • 1,076 Sq Ft

  16 N Main St, Essex, CT 06426

  This Charming Carriage house in the heart of Essex Village provides the perfect blend of historic charm and modern comfort. Enjoy a short stroll to local restaurants, the Connecticut River, Museums, marinas, boutique shopping and the Iconic Griswold Inn. Sunlight fills the space, creating a warm and inviting atmosphere. The living room boasts built-ins and a wood burning fireplace. Tiered gardens

  Alice Trautman William Raveis Real Estate

  16 N Main St, Essex, CT 06426
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  /37

  $699,000 Coming Soon

  • 3 Beds
  • 2 Baths
  • 2,948 Sq Ft

  24 Tower Hill Rd, Clinton, CT 06413

  Tucked away on over 7.5 private acres and abutting protected state forest, this rare Clinton property offers the perfect blend of tranquility, space, and flexibility. A true retreat, the setting provides exceptional privacy while still being conveniently located near shoreline amenities. This one owner home was designed for easy one-level living, the home features an inviting open floor plan with

  Gigi Giordano Taylor Compass Connecticut, LLC

  24 Tower Hill Rd, Clinton, CT 06413
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  /40

  $509,999

  • 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
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  /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
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  /30

  $749,000

  • 5 Beds
  • 4 Baths
  • 2,648 Sq Ft

  11 Phelps Rd, East Haddam, CT 06423

  Rare opportunity in the Hadlyme section of East Haddam featuring two dwellings on one parcel set in a scenic, natural setting. The main circa 1780 Mill House offers approximately 1,786 sq ft with original hardwood floors, chestnut paneling, two second-floor bedrooms, two additional attic rooms, and a first-floor suite with fireplace and private entrance overlooking a historic spring-fed pond.

  George Agnelli Agnelli Real Estate

  11 Phelps Rd, East Haddam, CT 06423
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  /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
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  /40

  $738,500 Coming Soon

  • 3 Beds
  • 1.5 Baths
  • 1,982 Sq Ft

  6 Pelton Hill Rd, Chester, CT 06412

  Nestled at the end of a peaceful, dead-end street, this beautifully maintained Carpenter Gothic home offers the perfect blend of historic charm and modern comforts. With its unique architectural style and serene private setting, this property is truly a hidden gem. The three Bedrooms are spacious and bright, each bedroom offers a cozy retreat with plenty of natural light and charming details that

  John Zubretsky Century 21 AllPoints Realty

  6 Pelton Hill Rd, Chester, CT 06412
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  /40

  $789,000

  • 3 Beds
  • 2.5 Baths
  • 2,798 Sq Ft

  17 Colonial Dr, Killingworth, CT 06419

  Escape to this serene nearly 6-acre homestead perfectly positioned at the end of a quiet cul-de-sac bordering a protected land trust preserve. This property offers the ultimate in privacy and a deep connection to nature with no through-traffic. The home is a modern farmhouse full of light and air, featuring an open floor plan and stunning wide-plank pine floors throughout. With 3 bedrooms, 2.5

  Susan Malan William Pitt Sotheby's Int'l

  17 Colonial Dr, Killingworth, CT 06419
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  /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
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  /16

  $1,025,000

  • Land
  • 1.02 Acres
  • $1,004,902 per Acre

  41B River Rd, Essex, CT 06426

  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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  /10

  $249,000

  • Land
  • 4.81 Acres
  • $51,767 per Acre

  48A Ironworks Rd, Clinton, CT 06413

  This 4.81-acre private building lot provides a blend of seclusion and convenience, making it an ideal spot to build your dream home. With 624 feet of pristine river frontage, you'll enjoy serene water views and easy access to nature. The lot features a private driveway for added exclusivity and has been thoughtfully prepared for construction-it's cleared, stumped, and even has a foundation hole

  Gigi Giordano Taylor Compass Connecticut, LLC

  48A Ironworks Rd, Clinton, CT 06413
• 

  

  /32

  $448,900 Open Sun 12PM - 1PM

  • 2 Beds
  • 1 Bath
  • 1,470 Sq Ft

  79 Middlesex Ave, Chester, CT 06412

  Charming Cape just steps from Chester Village! This inviting 2-bed, 1-bath home blends timeless New England character with everyday comfort and walk-to-village convenience. Warm newly refinished hardwood floors flow throughout the light-filled living room into the updated kitchen with its beautiful bow window and dining area. The kitchen is replete with ample granite counters, perfect for the

  Gigi Giordano Taylor Compass Connecticut, LLC

  79 Middlesex Ave, Chester, CT 06412
• 

  

  /14

  $240,000

  • 2 Beds
  • 1 Bath
  • 884 Sq Ft

  113 Union St Unit Z, Deep River, CT 06417

  FOR SALE: Deep River Condo This remodeled first-floor 2-bedroom condo is quietly located at Village Knoll near the village of Deep River. The unit features a spacious living room with dining area open to a updated galley kitchen. The primary bedroom includes a slider to a private covered deck. A second bedroom and remodeled full bath complete the layout. Shared laundry is on site. Well maintained

  Kevin Kennedy Kennedy Real Estate Solutions

  113 Union St Unit Z, Deep River, CT 06417
• 

  

  /11

  $725,000

  • Land
  • 0.29 Acre
  • $2,500,000 per Acre

  4 Bank Ln, Essex, CT 06426

  Amazing Essex Village location. 4 Bank Lane is one of four parcels which create an enclave in a prime spot in Essex Village yet is private and allows the abiltiy to build new. This special setting must be seen to fully understand the concept and possibilities. Viewings by appointment only please.

  Susan Malan William Pitt Sotheby's Int'l

  4 Bank Ln, Essex, CT 06426

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