Middlesex County CT Houses for Sale

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  /40

  $6,600,000

  • 6 Beds
  • 4 Baths
  • 5,739 Sq Ft

  11 River Edge Rd, Old Saybrook, CT 06475

  Riverside Elegance Meets Neoclassical Grandeur: Experience the pinnacle of waterfront living in this breathtaking Grecian Colonial estate, perfectly situated on 3.43 pristine acres overlooking the majestic Connecticut River. Spanning an impressive 7,239 square feet, including 1,500 finished square feet on the lower level including an ensuite bedroom and recreational room with French doors opening

  Colette Harron William Pitt Sotheby's Int'l

  11 River Edge Rd, Old Saybrook, CT 06475
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  /39

  $824,900

  • 4 Beds
  • 3.5 Baths
  • 2,706 Sq Ft

  275 W Main St, Chester, CT 06412

  Completely Reimagined 4 Bedrooms, 3.5 Bathrooms, 2 Acres, Luxury Primary Suite, Finished Lower Level. This classic New England charm meets a stunning, comprehensive renovation. Directly across from Cockaponset State Forest, this exceptional Chester home has been thoughtfully transformed to deliver modern luxury, comfort, and effortless turnkey living. From the moment you step inside, you'll

  Shirley Tapper Great Estates, CT

  275 W Main St, Chester, CT 06412
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  /36

  $850,000

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,552 Sq Ft

  9 Silver Springs Dr, Higganum, CT 06441

  Timeless Colonial design, thoughtfully arranged spaces and quality craftsmanship come together in this exceptional to be built offering in the highly desirable Chatham Lake neighborhood. Set on 2.32 acres and positioned along a gentle rise, this elevated homesite provides an attractive setting for two distinctive home designs offered at two different price points. The featured white Colonial,

  Rob Paskiewicz CT Home Pro, LLC

  9 Silver Springs Dr, Higganum, CT 06441
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  /40

  $479,500

  • 3 Beds
  • 2 Baths
  • 1,713 Sq Ft

  47 Spice Hill Dr, East Hampton, CT 06424

  Move right into this beautifully maintained Contemporary Cape in the popular Spice Hill subdivision! Freshly painted throughout with gleaming hardwood floors, this inviting home combines modern updates with timeless appeal. A cathedral ceiling, skylights, ceiling fans, and a fireplace create a bright, airy atmosphere, perfect for relaxing or entertaining. The open living and dining areas flow

  Rick Berkenstock CENTURY 21 AllPoints Realty

  47 Spice Hill Dr, East Hampton, CT 06424
• 

  

  

  /13

  $499,900

  • 4 Beds
  • 3.5 Baths
  • 4,390 Sq Ft

  57 Summer St, Portland, CT 06480

  Set on a generous 1.2-acre lot in Portland, this expansive ranch offers an incredible amount of space and potential for someone ready to bring their vision to life. With over 4,300 square feet of living space, the home features 10 rooms including 4 bedrooms and 3 full baths plus a half bath, providing plenty of room for extended living, hobbies, or multi-generational needs. The layout offers the

  Carl Guild Carl Guild & Associates

  57 Summer St, Portland, CT 06480
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  /34

  $1,295,000

  • 4 Beds
  • 3.5 Baths
  • 2,656 Sq Ft

  1409 Millbrook Rd, Middletown, CT 06457

  Nestled on an extraordinary 39-acre estate with breathtaking panoramic views, this stunning custom log home offers the perfect blend of rustic elegance, modern comfort, and exceptional investment potential. Originally built in 2005 with an addition completed in 2014, the home features 4 bedrooms and 3 full bathrooms. The interior showcases soaring cathedral ceilings, beautiful tile flooring,

  Barbara Puorro Puorro Realty Group

  1409 Millbrook Rd, Middletown, CT 06457
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  /40

  $730,000

  • 4 Beds
  • 2.5 Baths
  • 2,964 Sq Ft

  9 Taylor Ridge Rd, Clinton, CT 06413

  4 Bedroom Colonial on a cul-de-sac not far from town and schools. Open & spacious first floor with 9ft ceilings offers a Living Room, Dining Room, a large Eat-in Kitchen, Family Room with fireplace and a powder room. The second floor has the Primary Suite with custom bathroom and walk-in closet, as well as 3 more bedrooms and a full bath. Addionally it has a huge 22x25 Bonus Room and convenient

  Craig Milton Re/Max Valley Shore

  9 Taylor Ridge Rd, Clinton, CT 06413
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  /31

  $304,900

  • 3 Beds
  • 1 Bath
  • 888 Sq Ft

  18 Lake Blvd, East Hampton, CT 06424

  Great opportunity to own this enchanting 3-bedroom Cape located in a desirable lake community, just a short walk to beautiful Lake Pocotopaug and Sears Park. This warm and inviting home offers a comfortable open floor plan with a seamless flow through the living and dining areas. The beautifully remodeled bathroom brings a fresh, modern touch, while the large eat-in kitchen-featuring new tile

  Gene Pica RE/MAX Alliance

  18 Lake Blvd, East Hampton, CT 06424
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  /40

  $599,900

  $25K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,683 Sq Ft

  16 Hawthorne Rd, East Hampton, CT 06424

  Welcome to lake living at its best in the desirable Brookhaven Lake Association! Beautifully remodeled and ideally situated directly across from the association boat dock with a private launch and beach, this charming 3-bedroom, 2-full-bath home offers the perfect blend of modern comfort and relaxed waterfront living. Set on a beautiful, level lot with water views, the home features a bright,

  Linda Muraski Century 21 Classic Homes

  16 Hawthorne Rd, East Hampton, CT 06424
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  /25

  $689,000

  New Construction

  • 2 Beds
  • 2 Baths
  • 1,555 Sq Ft

  UNIT 2-41 Webster Ln Unit 145, Middletown, CT 06457

  Expect the best! Carefree living at Founders' Ridge, the premier award-winning 55+ community in Central Connecticut! Introducing the highly sought-after Kirby II model home, now available for IMMEDIATE occupancy. This is the last Kirby II available at this price point. Located in Middletown's desirable Westfield section, this thoughtfully designed 1,555-square-foot, single-level home offers an

  Phyllis Bysiewicz Berkshire Hathaway NE Prop.

  UNIT 2-41 Webster Ln Unit 145, Middletown, CT 06457
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  /20

  $429,000

  • 3 Beds
  • 1.5 Baths
  • 1,581 Sq Ft

  76 George St, Middletown, CT 06457

  Welcome to 76 George St, Middletown! This 1,600 SF home offers 3 bedrooms, a spacious kitchen, and plenty of potential to make the property your own. The walk-out lower level features roughed-in plumbing, creating an exciting opportunity for additional living space, a recreation area, or a possible in-law apartment. Set on nearly one acre of land, the property offers additional road frontage on

  Santo Gulino William Raveis Real Estate

  76 George St, Middletown, CT 06457
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  /40

  $1,380,000

  Open Sun 12PM - 2PM Coming Soon

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

  46 Fenwood Grove Rd, Old Saybrook, CT 06475

  Step through the front door and experience a warm European inspired feel in this distinctive Fenwood Beach Association home. Offering exceptional flexibility and comfortable one-level living, the home features four bedrooms in the original residence, plus an additional bedroom and spacious in-law/primary suite in the addition, ideal for multi-generational living, guests, or a private retreat. The

  Mary Maffuid Berkshire Hathaway NE Prop.

  46 Fenwood Grove Rd, Old Saybrook, CT 06475
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  /17

  $410,000

  $15K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,112 Sq Ft

  104 Higby Rd, Middletown, CT 06457

  Welcome to this charming 3-bedroom, 1-bath ranch nestled on the highly sought-after Higby Road. Set on a generous half-acre lot, this home offers the perfect opportunity for first-time buyers, downsizers, or anyone looking to add their personal touch. Inside, you'll find comfortable one-level living with a functional layout, hardwood floors, and a cozy fireplace. Additional features include an

  Jacqueline Caban William Raveis Real Estate

  104 Higby Rd, Middletown, CT 06457
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  /37

  $585,000

  • 3 Beds
  • 2.5 Baths
  • 1,920 Sq Ft

  49 Iron Works Rd, Killingworth, CT 06419

  Nicely updated home with open floor plan and cathedral ceilings in the main Living/Dining/Kitchen Area. The Family room is large, has a fireplace and looks out across the 24x26 deck at the private backyard. There is also a first floor bedroom or office and a half bath with laundry. The second floor has a spacious primary suite with a fireplace, full bath and walk in closet. Additionally, it has

  Craig Milton Re/Max Valley Shore

  49 Iron Works Rd, Killingworth, CT 06419
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  /2

  $285,000

  • 3 Beds
  • 1 Bath
  • 941 Sq Ft

  43 Quarry St, Old Saybrook, CT 06475

  43 Quarry Street, Loved and occupied by the same owner for more than 40 years, this three-bedroom home on Quarry Street presents a rare opportunity in the heart of Old Saybrook. Set on .25 acres on a quiet dead-end street, the real story here is the location. Enjoy an easy walk with sidewalk access into Old Saybrook's vibrant Main Street for coffee, restaurants, shopping, the library, and all the

  Jennifer Gurnell William Raveis Real Estate

  43 Quarry St, Old Saybrook, CT 06475
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  /33

  $424,900

  • 4 Beds
  • 2.5 Baths
  • 2,030 Sq Ft

  28 Tennyson Rd, East Hampton, CT 06424

  Completely remodeled from top to bottom and showing like brand-new construction, this beautifully refreshed home offers bright, inviting living spaces and a fantastic location in the Pocotopaug Lake community. The first floor features hardwood flooring and an open, comfortable layout with a spacious kitchen, dining area and sun-filled living room with access to the covered deck. Upstairs,

  Linda Edelwich William Raveis Real Estate

  28 Tennyson Rd, East Hampton, CT 06424
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  /40

  $749,900

  • 4 Beds
  • 2.5 Baths
  • 2,458 Sq Ft

  88 Powder Hill Rd, Middlefield, CT 06455

  Nestled in the heart of scenic Middlefield, this distinctive and beautifully maintained 4 bedroom 2.5 bathroom property offers a rare blend of classic New England character and modern flexibility. Inside on the first floor, an open-concept kitchen and dining area invite gathering and entertaining, seamlessly flowing into a sunroom-style flex space with room to grow-ideal for a home office,

  Gary Marino William Raveis Real Estate

  88 Powder Hill Rd, Middlefield, CT 06455
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  /32

  $995,000

  $105K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,153 Sq Ft

  65 Knollwood Dr, Old Saybrook, CT 06475

  The best of both worlds-enjoy the tranquility of a peaceful setting while being just a short stroll to the beach. Beautifully updated and impeccably maintained, this year-round home offers the perfect blend of coastal charm and modern comfort. A welcoming front porch invites you inside where you'll find beautifully renovated kitchen and baths as well as quality finishes throughout. You'll love

  Martha Quaratella Coldwell Banker Realty

  65 Knollwood Dr, Old Saybrook, CT 06475
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  /25

  $189,000

  $11K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 448 Sq Ft

  2 Hay Field Rd, East Haddam, CT 06415

  This charming and cozy Lake Hayward cottage is ready for your personal touch, making it the perfect summer vacation spot or weekend retreat. Major updates have already been completed, including a newer roof, siding, windows, and an updated electrical panel. Relax on the sun-filled porch, catch a cool breeze on the deck, and enjoy being just a short walk from four private association beaches. The

  Carolyn Kress Berkshire Hathaway NE Prop.

  2 Hay Field Rd, East Haddam, CT 06415
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  /31

  $345,000

  • 3 Beds
  • 1.5 Baths
  • 1,304 Sq Ft

  40 Fairview St, Portland, CT 06480

  HIGHEST AND BEST BY TUESDAY 9/15/2026 8PM! A little cottage with a lot to love! This charming Cape Cod sits on a picturesque corner lot in the heart of Portland, offering beautiful curb appeal and a welcoming setting. The main level features two separate living areas filled with natural light, including one with a cozy fireplace and built-in bookshelves that create a warm and inviting space full

  Rebecca lucian Mapleridge Realty

  40 Fairview St, Portland, CT 06480
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  /28

  $2,400,000

  • 8 Beds
  • 3 Baths
  • 2,709 Sq Ft

  127 Shore Rd, Clinton, CT 06413

  Three direct beachfront cottages located right on the sand of the Long Island Sound in Clinton, Connecticut offer a rare turnkey coastal investment opportunity. The property includes two well-appointed 2-bedroom cottages and one spacious 4-bedroom cottage, all fully furnished and recently updated for modern comfort. Each cottage provides unobstructed waterfront views, immediate beach access, and

  Sharlene Kieslich LAER Realty Partners

  127 Shore Rd, Clinton, CT 06413
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  /22

  $799,999

  • 3 Beds
  • 2 Baths
  • 1,338 Sq Ft

  103 Old Salt Works Rd, Westbrook, CT 06498

  Sea Salt Air Changes Everything... The mood. The conversation. The momentum. When you are here you will find yourself at the crossroads of nature and civilization. Stroll to a private association beach from this restful retreat. Stretch out on the deck overlooking swaying seagrass. Sing in the outdoor shower. Go on, no one is listening. Deck with awning and marsh views. Fenced in yard featuring

  Heather McGuinness William Raveis Real Estate

  103 Old Salt Works Rd, Westbrook, CT 06498
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  /40

  $409,995

  $25K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,333 Sq Ft

  165 Colchester Ave, East Hampton, CT 06424

  Comfort, convenience, and efficiency on nearly 1 acre are the highlights of this well-maintained 3-bedroom, 2 full bath Ranch. This home is equipped with energy money saving systems. Home includes a whole house electric heat pump, central air, hybrid heat pump water heater, automated water filtration system and updated well pump tank for year-round comfort. This single level home boasts an open

  Polly Carilli William Raveis Real Estate

  165 Colchester Ave, East Hampton, CT 06424
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  /13

  $2,800,000

  • 15 Beds
  • 7.5 Baths
  • 10,623 Sq Ft

  153 Wallingford Rd, Durham, CT 06422

  This unique farm complex is comprised of an equestrian area for 40 horses +, 5 residential houses and more. It has been in operation for over 100 years and is ready for new multi-generation owners to take the reins or for a progressive investor. There is nearly 280 acres of outstanding land, a pond, pastureland, rolling hills, stalls for 40+ horses and much more. There is, also, an outstanding

  Gary Dobratz Century 21 AllPoints Realty

  153 Wallingford Rd, Durham, CT 06422
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  /31

  $767,000

  New Construction

  • 2 Beds
  • 2.5 Baths
  • 2,552 Sq Ft

  215 Chamberlain Hill Rd Unit 1, Higganum, CT 06441

  Tucked into a quiet corner of Higganum, where the Connecticut River valley still feels like the country, The Enclave is a private community of eight to-be built homes designed around a simpler, fuller way of living - less to maintain, and more room for what matters. "The Shiloh" model offers 2,552 square feet of thoughtfully open living, with the primary suite on the main level so everyday life

  Nick DeLuca eXp Realty

  215 Chamberlain Hill Rd Unit 1, Higganum, CT 06441
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  /35

  $699,900

  $25K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,833 Sq Ft

  4 Pine Place, Clinton, CT 06413

  REDUCED PRICE! Welcome home to this charming and beautifully updated Cape nestled on a quiet dead-end street in a wonderful waterfront community. This inviting 4-bedroom, 2-full-bath home sits on a generous quarter-acre lot and is just a half-mile stroll to the town marina, waterfront, and local restaurants. The interior features beautifully refinished hardwood floors, elegant crown molding, and

  Christina King Connecticut Real Estate Group LLC

  4 Pine Place, Clinton, CT 06413
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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

  $1,100,000

  • 3 Beds
  • 3 Baths
  • 2,556 Sq Ft

  18 Cedar Ln, Westbrook, CT 06498

  Welcome to 18 Cedar Lane in Westbrook-a contemporary 3-bedroom, 3-full-bath home offering the perfect blend of modern living and beach-community lifestyle. Step inside to an open-concept living space highlighted by soaring cathedral ceilings, and the stone wood burning fireplace in the living room. Open to a beautifully remodeled kitchen completed in 2023 with an adjacent dining area. Designed

  Carolyn Augur FIV Realty Co. Connecticut, LLC

  18 Cedar Ln, Westbrook, CT 06498
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  /39

  $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

  Essex Village is a short walk to this one-of-a-kind home, privately set on over three picturesque acres. 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

  Gigi Giordano Taylor Compass Connecticut, LLC

  106 Meadow Woods Rd, Deep River, CT 06417
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  /33

  $549,000

  • 3 Beds
  • 2.5 Baths
  • 2,128 Sq Ft

  4 Sears Place, East Hampton, CT 06424

  Get ready to experience all that lake life has to offer at this meticulously maintained Lake Pocotopaug home! This picturesque retreat is just a short walk to a private beach association and includes a deeded right-of-way to a nearby boat launch, providing convenient access to the lake. As you enter the home from the front Trex porch, you're greeted by an open-concept floor plan filled with

  James Harrington Carl Guild & Associates

  4 Sears Place, East Hampton, CT 06424
• 

  

  /40

  $764,900

  Open Sat 11AM - 2PM Coming Soon

  • 4 Beds
  • 2.5 Baths
  • 2,662 Sq Ft

  13 High Field Ln, Chester, CT 06412

  Privacy, space, and location come together in this classic custom colonial nestled on over two private acres at the end of a quiet cul-de-sac just minutes from the heart of Chester Village. Lovingly cared for by its original owners, this 2,662-square-foot home offers a rare opportunity to enjoy the tranquility of a tucked-away setting without sacrificing proximity to downtown. An inviting covered

  Susan Malan William Pitt Sotheby's Int'l

  13 High Field Ln, Chester, CT 06412
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  /38

  $549,000

  • 3 Beds
  • 2 Baths
  • 2,648 Sq Ft

  18 Orchard Heights Rd, Essex, CT 06426

  Welcome to 18 Orchard Heights Road, a charming modified saltbox colonial located at the end of a cul-de-sac in a desirable neighborhood. This home offers exceptional convenience, located just minutes from the boutique shops and historic charm of downtown Essex, with quick access to the vast amenities, dining, and shoreline conveniences of neighboring Old Saybrook. Inside, the home features a

  Erin Borruso William Pitt Sotheby's Int'l

  18 Orchard Heights Rd, Essex, CT 06426
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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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  /36

  $450,000

  $35K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,916 Sq Ft

  98 Maple Rd, Portland, CT 06480

  Timeless and charming colonial offers stunning details around every corner. First floor boasts a formal dining room with built-ins, full living room and den (each with a fireplace), kitchen and keeping room, foyer, and half bath. French doors lead from the dining room to a screened porch perfect for outdoor lounging and taking in the idyllic 1.5 acre property complete with 2 car garage as well as

  Josh James Farnam Realty Group

  98 Maple Rd, Portland, CT 06480
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  /36

  $599,900

  $245K PRICE DROP

  • 4 Beds
  • 1.5 Baths
  • 2,070 Sq Ft

  110 Freeman Rd, Middletown, CT 06457

  Step back in time while enjoying the comfort of modern updates in this distinctive 1868 home in Middletown's desirable South Farms area. Set on a property rich in character, history, and functionality, this unique home offers 3 bedrooms, 1 1/2 baths, an upstairs office, and a completely remodeled kitchen area. The full-height basement features a granite foundation, poured concrete floor, and

  Pam Rizy Berkshire Hathaway NE Prop.

  110 Freeman Rd, Middletown, CT 06457
• 

  

  /40

  $1,100,000

  $195K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,904 Sq Ft

  26 Willard Ave, Old Saybrook, CT 06475

  Welcome to shoreline living at its finest in one of Old Saybrook's desirable beach communities, just minutes from the water, marinas, beaches, restaurants, and all that the Connecticut shoreline has to offer. This beautifully remodeled split-level ranch combines modern updates, flexible living space, and an exceptional outdoor setting. Step inside to an inviting open-concept floor plan filled

  Gigi Giordano Taylor Compass Connecticut, LLC

  26 Willard Ave, Old Saybrook, CT 06475
• 

  

  /3

  $1,590,000

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,070 Sq Ft

  13 College St, Old Saybrook, CT 06475

  13 College Street | Old Saybrook, CT TO BE BUILT Discover the opportunity to build your dream home in one of Old Saybrook's most desirable locations-Saybrook Point. Thoughtfully designed with luxury, comfort, and flexibility in mind, this exceptional new construction home offers approximately 2,070 square feet, four bedrooms, two and one-half baths, and the ability to personalize finishes to suit

  Lisa Fekete William Raveis Real Estate

  13 College St, Old Saybrook, CT 06475
• 

  

  /32

  $465,000

  • 3 Beds
  • 1.5 Baths
  • 2,031 Sq Ft

  6 Castle View Dr, Chester, CT 06412

  One level living at its best! Tucked away in a peaceful neighborhood, 6 Castle View Drive offers the perfect blend of comfort, charm, and convenience. This lovingly cared for home features 3 bedrooms, 1.5 baths, and 2,031 square feet of thoughtfully designed living space all set on a beautifully level 0.43 acre lot. Step inside through the breezeway, kick off your shoes, hang your coat, and make

  Alan Spotlow William Raveis Real Estate

  6 Castle View Dr, Chester, CT 06412
• 

  

  /4

  $747,900

  New Construction Open House 9/27

  • 3 Beds
  • 2 Baths
  • 2,046 Sq Ft

  507 Freya Ln, East Hampton, CT 06424

  The awaited Phase II is now available for Lake Overlook Estates. 2 beautiful homesites with views of Lake Pocotopaug. Lot 16 is 1.22 acres and Lot 20 is 2.21 acres. The Charlestown. Attention Ranch lovers - look no further! There are not enough descriptive words to describe this amazing home. From the quaint covered front porch to the peaks and gables that offers a true architectural splendor

  Mark Toledo Berkshire Hathaway NE Prop.

  507 Freya Ln, East Hampton, CT 06424

Showing Results 121 - 160, Page 4 of 8