Connecticut Homes for Sale with Private Pool

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  $519,000

  • 2 Beds
  • 2.5 Baths
  • 1,796 Sq Ft

  63 Woodbury Hill Unit 63, Woodbury, CT 06798

  Exceptionally private, Putnam Loft model in the sought after Woodbury Hill! This unit is located in a secluded part of the community with woods behind and only sounds of the nearby babbling brook. This well-cared for unit features hardwood floors throughout, vaulted ceilings, floor to ceiling gas fireplace, a large dining room and remodeled kitchen. The primary bedroom suite is on the main level

  Katherine Parlato Drakeley Real Estate, Inc.

  63 Woodbury Hill Unit 63, Woodbury, CT 06798
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  /39

  $714,900

  • 4 Beds
  • 3.5 Baths
  • 3,694 Sq Ft

  2 Quail Hollow Ct, Beacon Falls, CT 06403

  Welcome to 2 Quail Hollow Court, a spacious 4-bedroom, 3.5-bath Colonial tucked away on a desirable cul-de-sac in Beacon Falls, set on 1.87 picturesque acres, which offers a wonderful combination of comfort, functionality, and space for both everyday living and entertainment. The spacious kitchen features granite countertops, a breakfast bar, and a dining area that opens seamlessly to the

  Floyd O'Connor Realty ONE Group Connect

  2 Quail Hollow Ct, Beacon Falls, CT 06403
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  /23

  $499,999

  • 4 Beds
  • 1.5 Baths
  • 2,240 Sq Ft

  18 Lawler Rd, West Hartford, CT 06117

  Classic 4 bedroom, New England colonial with hardwoods throughout. Expansive, heated sunroom overlooking private, fully fenced backyard with in-ground pool. Move in before summer and start hosting your backyard barbecues in the well desired Bishops corner area. Close to shopping, schools and the Trout Brook trail.

  Sondra Maddox GRL & Realtors, LLC

  18 Lawler Rd, West Hartford, CT 06117
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  /36

  $685,000

  Open Sat 12PM - 2PM

  • 2 Beds
  • 2.5 Baths
  • 1,719 Sq Ft

  2435 Bedford St Unit 11C, Stamford, CT 06905

  Welcome to this beautifully maintained end-unit townhouse located in the desirable Chesterfield community of Stamford, CT. This spacious home offers 2 bedrooms, 2.5 bathrooms, and a versatile multi-level layout perfect for modern living. The main level features a bright and open living room and dining room combination with hardwood floors and a glass slider leading to a private deck-ideal for

  Deirdre Clement William Raveis Real Estate

  2435 Bedford St Unit 11C, Stamford, CT 06905
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  /51

  $19,900,000

  • 7 Beds
  • 10 Baths
  • 18,000 Sq Ft

  37 Burying Hill Rd, Greenwich, CT 06831

  Custom designed and built to exacting standards, this phenomenal back country lakefront compound was built to exacting standards offering fabulous privacy and flexibility for families, guests and staff. Prominent local design build firm created a masterpiece that combines a pre war elegance with substantial entertaining and modern lifestyle amenities. Multiple structures, including a large pool

  Robert Johnson Brown Harris Stevens CT, LLC

  37 Burying Hill Rd, Greenwich, CT 06831
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  /2

  $489,900

  • 3 Beds
  • 2.5 Baths
  • 2,080 Sq Ft

  131 Ashley Rd, Bristol, CT 06010

  Located on the Burlington side of Bristol, Desirable Bristol Neighborhood. Home offers spacious eat-in kitchen with sliders to deck and pool. Formal dinning Room, Living room and Family Room with fireplace on the main level. The lower level has a Theater Room with heat.

  Ronald Forcier Century 21 AllPoints Realty

  131 Ashley Rd, Bristol, CT 06010
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  /38

  $1,399,000

  • 6 Beds
  • 7 Baths
  • 7,071 Sq Ft

  132-MF Merrimac Dr, Trumbull, CT 06611

  A rare opportunity to own an exceptional legal multi-generational property featuring two fully independent residences on one remarkable parcel. Perched atop Tashua Hills, this one-of-a-kind offering showcases breathtaking panoramic views of the reservoir and rolling hills beyond. The main residence offers convenient one-level living with vaulted ceilings, exposed beams, hardwood floors, and walls

  Stefanie Runlett RE/MAX Heritage

  132-MF Merrimac Dr, Trumbull, CT 06611
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  /40

  $14,900,000

  • 5 Beds
  • 9 Baths
  • 9,546 Sq Ft

  279 Saugatuck Ave, Westport, CT 06880

  Panoramic views of Long Island Sound extend from this gated, resort-like estate. Designed to maximize its spectacular waterfront setting, the east-facing main house takes in the coastal views from walls of windows, glass French doors, and private balconies. Effortless indoor-outdoor flow defines the main level, where a charming screened-in porch and awning-covered veranda overlook a Gunite pool

  Joseph Barbieri Sotheby's International Realty

  279 Saugatuck Ave, Westport, CT 06880
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  /40

  $729,000

  • 3 Beds
  • 2.5 Baths
  • 2,120 Sq Ft

  185 Brentwood Cir Unit 185, Danbury, CT 06810

  Welcome to The Rivington, where resort style amenities meet modern luxury. This bright and spacious end unit townhouse offers an exceptional living experience, perfect for both relaxation and entertaining. Updated light fixtures throughout the home. Enjoy the beautiful kitchen featuring stainless steel appliances, granite countertops, center island, pantry, and slider leading to the outdoor deck.

  Tony Zaccardo Coldwell Banker Realty

  185 Brentwood Cir Unit 185, Danbury, CT 06810
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  /40

  $2,679,000

  $171K PRICE DROP

  • 6 Beds
  • 6.5 Baths
  • 7,200 Sq Ft

  20 Cherry Ln, Wilton, CT 06897

  20 Cherry Lane is a rare Georgian Colonial estate set on nearly 2.5 flat, manicured acres bordering 50 acres of protected conservation land and hiking trails. Offering over 7200 sqft, with an additional 2100+ sqft lower level, this home combines exceptional scale, modern updates, and long-term value. Designed for entertaining and everyday living, the renovated chef's kitchen features double

  Molly Rubins NestSeekers International

  20 Cherry Ln, Wilton, CT 06897
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  /27

  $495,000

  • 2 Beds
  • 2.5 Baths
  • 2,198 Sq Ft

  93 Litchfield Ponds Dr, Litchfield, CT 06759

  Welcome to tranquil Litchfield Ponds! This well maintained Tri-level Townhouse with view of pond has over 2100sq ft. Step directly front he one car garage into the spacious kitchen with stainless steel appliances and then onto the open living and dining areas. The living room features tons of natural light and a wood burning fireplace. The cecond floor has two bedrooms each with a full bath and

  Andrew Murphy E.J. Murphy Realty

  93 Litchfield Ponds Dr, Litchfield, CT 06759
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  /36

  $995,000

  $200K PRICE DROP

  • 5 Beds
  • 5 Baths
  • 2,804 Sq Ft

  286 South St, Roxbury, CT 06783

  Discover this charming 4-bedroom Colonial with 1 additional bedroom is attached in-law apt on the southern side of Roxbury, offering an idyllic escape with seamless access to NYC. This privately situated home rests in a serene meadow, gracefully bordered by Pierce Brook. The main residence features a comfortable layout with a living room and fireplace that flows into the dining area and kitchen.

  Kathryn Clair William Pitt Sotheby's Int'l

  286 South St, Roxbury, CT 06783
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  /29

  $219,900

  • 2 Beds
  • 1.5 Baths
  • 1,056 Sq Ft

  11 Lakeside Dr Unit 18, Bristol, CT 06010

  ***HIGHEST AND BEST OFFERS DUE BY FRIDAY, 6/5 AT NOON.*** Welcome to maintenance-free living at South Mountain! This beautifully maintained 2-bedroom, 1.5-bathroom townhome offers the perfect blend of comfort and modern convenience. The main level features new luxury vinyl plank flooring throughout, creating a bright and airy living space that flows seamlessly into the kitchen and dining area.

  Dawn Gagliardi Serhant Connecticut, LLC

  11 Lakeside Dr Unit 18, Bristol, CT 06010
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  /35

  $699,000

  • 4 Beds
  • 2.5 Baths
  • 3,513 Sq Ft

  60 W Meadow Rd, Hamden, CT 06518

  Nestled on a private lot in Hamden's highly desirable West Woods neighborhood, this beautifully maintained home offers comfort, elegance, and exceptional functionality. The heart of the home is the stunning custom kitchen, renovated in 2016 with style & practicality in mind. A large granite-topped island provides extra storage, power access, pull-out recycling and garbage bins, and a dedicated

  Debbie Schlegel Coldwell Banker Realty

  60 W Meadow Rd, Hamden, CT 06518
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  /39

  $1,695,000

  • 5 Beds
  • 5.5 Baths
  • 5,308 Sq Ft

  110 Sport Hill Rd, Redding, CT 06896

  A rare blend of scale, privacy and value, this beautifully maintained Redding retreat offers over 6,000 square feet of flexible living space. From the gracious front entry, the home unfolds with purpose and ease. To the right, a private library/home office creates a quiet place to work. Straight ahead, the living room frames peaceful views of the pool and grounds, while the formal dining room

  Tara Hawley Coldwell Banker Realty

  110 Sport Hill Rd, Redding, CT 06896
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  /40

  $2,950,000

  • 6 Beds
  • 3.5 Baths
  • 5,105 Sq Ft

  40 Rogers Rd, Stamford, CT 06902

  Tucked within Stamford's coveted Shippan Point, 40 Rogers Road presents a refined coastal offering just moments from the water. Thoughtfully reimagined, the residence blends timeless character with a comprehensive suite of recent upgrades, delivering a turnkey living experience. Sun-filled interiors offer well-proportioned spaces with seamless flow for everyday living and entertaining. The second

  Ryan Dichter Compass Connecticut, LLC

  40 Rogers Rd, Stamford, CT 06902
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  /39

  $611,000

  • 4 Beds
  • 2 Baths
  • 2,123 Sq Ft

  327 W Main St, Cheshire, CT 06410

  A showstopper!! This fully updated home seamlessly blends timeless character and charm with every modern convenience. Featuring 4 bedrooms and 2 full baths, this refreshed property offers the warmth and craftmanship of a vintage home paired with an updated move in ready feel. Enjoy peace of mind with new windows, gutters, fresh interior paint, on demand hot water system, and a new mini split

  Katie Breitkreutz Dave Jones Realty, LLC

  327 W Main St, Cheshire, CT 06410
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  /34

  $725,000

  • 3 Beds
  • 2 Baths
  • 2,248 Sq Ft

  602 Durham Rd, Madison, CT 06443

  602 Durham Road delivers the lifestyle living by the shoreline is known for, starting the moment you pull into the circular driveway. The covered front porch sets the tone, but the backyard is the headline: a resort-caliber outdoor environment anchored by an in-ground pool, hot tub, covered patio with TV, outdoor kitchen with built-in grill, oversized high-top bar, pizza oven, basketball court,

  Heidi DeRusso Coldwell Banker Realty

  602 Durham Rd, Madison, CT 06443
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  /25

  $1,068,000

  New Construction Open Sat 1PM - 3PM $130K PRICE INCREASE

  • 2 Beds
  • 2 Baths
  • 3,002 Sq Ft

  4 Holly Ridge Way Unit Lot 80, Danbury, CT 06810

  The Alstead blends sophistication with everyday comfort in a thoughtfully planned 55+ community-the only opportunity to own a single-family home with resort-style amenities and primary living on the first floor. A welcoming foyer with a tray ceiling leads past a versatile flex room into the open main living area, where an elegant dining room flows into a spacious great room featuring a cozy

  Lauren Logiacco Thomas Jacovino

  4 Holly Ridge Way Unit Lot 80, Danbury, CT 06810
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  /23

  $229,000

  $21K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,410 Sq Ft

  373 Trailsend Dr, Torrington, CT 06790

  3-bedroom Woodhaven model in excellent condition. Bedroom and full bath on main level. Living room has a pellet stove insert and a split system for heat & a/c. It also has a half-vaulted ceiling with a ceiling fan & skylight. Engineered hardwood throughout the main level. Sliders from dining room to a large expanded deck. Upstairs you have the primary bedroom with vaulted ceiling and another

  MARY CLANCEY William Pitt Sotheby's Int'l

  373 Trailsend Dr, Torrington, CT 06790
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  /40

  $775,000

  Open Sun 12PM - 3PM Coming Soon

  • 4 Beds
  • 2.5 Baths
  • 2,832 Sq Ft

  24 Jericho Dr, Old Lyme, CT 06371

  This exceptional and spacious mid-century modern home offers incredible updates in a stunning setting. The design creates natural separation between entertaining spaces, quiet bedroom quarters, and informal gathering areas. The main level is comprised of a granite/stainless kitchen, large dining room and formal living room with gas fireplace. A short flight of stairs leads to 4 bedrooms and two

  Nancy Mesham Coldwell Banker Realty

  24 Jericho Dr, Old Lyme, CT 06371
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  /30

  $699,999

  Open Sat 12PM - 2PM

  • 3 Beds
  • 3.5 Baths
  • 2,120 Sq Ft

  14 E Cross Trail Unit 14, Danbury, CT 06810

  This is the one you've been waiting for. A 2022-built Toll Brothers townhome in Danbury, CT's coveted Woodlands Community at Rivington, and this one won't last. Imagine starting every morning in a chef's kitchen designed for the way you actually live, granite counters, oversized island, gas cooktop, wall oven, and wine chiller, then stepping onto your private deck with coffee in hand. This is

  Chelsea Stinson Lake Homes Realty, LLC

  14 E Cross Trail Unit 14, Danbury, CT 06810
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  /34

  $425,000

  Open Sun 12PM - 2PM

  • 3 Beds
  • 2.5 Baths
  • 2,268 Sq Ft

  186 Schaffer Rd, Bethany, CT 06524

  Enjoy one level living in this large ranch style home offering 2,268 sq. ft. in Bethany. Spacious kitchen with brick wall. Living room/Dining room with fireplace. There are 3 bedrooms and 2.5 baths, first floor family room with fireplace. Also, an office or guest room, large unfinished basement and 2-car attached garage. This home sits on a beautiful level 1.7-acre parcel. Property abuts the

  Irma Nesson Calcagni Real Estate

  186 Schaffer Rd, Bethany, CT 06524
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  /32

  $1,699,000

  Open Sat 11AM - 1PM

  • 4 Beds
  • 2.5 Baths
  • 3,290 Sq Ft

  34 Orchard Rd, Milford, CT 06460

  Rebuilt inside and out in 2019, this home offers a bright, open layout designed for everyday living and elegant entertaining-just steps from Long Island Sound with the rare benefit of no flood or wind insurance required. The main level features a chef's kitchen with high-end appliances, walk-in pantry and breakfast nook that flows into the dining and family rooms. Upstairs, the vaulted primary

  Frank D'Ostilio Houlihan Lawrence WD

  34 Orchard Rd, Milford, CT 06460
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  /37

  $589,000

  • 4 Beds
  • 2.5 Baths
  • 2,206 Sq Ft

  71 Bainton Rd, West Hartford, CT 06117

  Welcome to 71 Bainton Road, a classic 4-bedroom Colonial in Golf Acres, a lovely, highly sought-after West Hartford neighborhood. Solidly maintained with great bones, this home stands ready for its next chapter. It offers the ideal opportunity for someone looking for a structurally sound property who wants to layer in their own cosmetic updates and modern design choices over time to create their

  Karen Tuvin William Raveis Real Estate

  71 Bainton Rd, West Hartford, CT 06117
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  /40

  $1,550,000

  $50K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 4,452 Sq Ft

  380 Southbury Rd, Roxbury, CT 06783

  Nestled on nearly seven private acres along a quiet country road in picturesque Roxbury, this exceptional residence offers a seamless blend of elegance, comfort, and classic New England charm. Set back from the road with a gently curving drive, the home welcomes you with a dramatic two-story foyer and grand staircase, complemented by hardwood floors, detailed millwork, crown molding, tray

  ROSEANN BLANTON Berkshire Hathaway NE Prop.

  380 Southbury Rd, Roxbury, CT 06783
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  /43

  $14,900,000

  • 5 Beds
  • 8 Baths
  • 9,546 Sq Ft

  279 & 281 Saugatuck Ave, Westport, CT 06880

  Panoramic vistas of Long Island Sound extend from this gated, resort-style estate. Designed to maximize its spectacular waterfront setting, the east-facing main house takes in the coastal views from walls of windows, French doors, and private balconies. Effortless indoor-outdoor flow defines the main level, where a charming screened-in porch and awning-covered veranda overlook a Gunite pool with

  Joseph Barbieri Sotheby's International Realty

  279 & 281 Saugatuck Ave, Westport, CT 06880
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  /35

  $7,400,000

  • 7 Beds
  • 7 Baths
  • 6,844 Sq Ft

  102 Melius Rd, Warren, CT 06754

  Reverie Farm is an exceptionally rare late 18th century stone and shingle estate, on more than one hundred acres, located in one of the highest and most private parts of Connecticut. Situated in the heart of Litchfield County, the property rises more than 1,200 feet in elevation across four distinct tax parcels, among which are several estate quality building sites. The setting is dreamlike in

  Andrew Gates Houlihan Lawrence, Inc.

  102 Melius Rd, Warren, CT 06754
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  /24

  $279,900

  • 2 Beds
  • 2 Baths
  • 1,386 Sq Ft

  13 Byrne Ct Unit G, Farmington, CT 06032

  Welcome to this bright and beautifully townhome in the highly desirable Talcott Glen complex-just minutes from UConn Health Center, major highways, shopping, dining and much more. Nestled within a peaceful, lush setting, this home offers both privacy and convenience. Upon entry, you're greeted by a tiled foyer, that leads into an open concept floor plan filled with natural light, the living room

  Melenie Phillips Signature Properties of N.E.

  13 Byrne Ct Unit G, Farmington, CT 06032
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  /26

  $5,595,000

  Open Thu 11AM - 1PM

  • 5 Beds
  • 10 Baths
  • 9,806 Sq Ft

  42 Nettleton Hollow Rd, Washington, CT 06793

  Stone Bridge: The Ultimate Classic Country Estate - PERFECTION AND READY TO MOVE IN! Embodying the pinnacle of refined country living, "Stone Bridge" is a magnificent stone and shingle estate with Elevator to all floors and Geothermal Heating, that seamlessly marries timeless architectural grandeur with state-of-the-art modern amenities. Situated on over 24.9 private, bucolic acres in Washington,

  Kathryn Clair William Pitt Sotheby's Int'l

  42 Nettleton Hollow Rd, Washington, CT 06793
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  /34

  $585,000

  $14K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,017 Sq Ft

  111 Logging Trail Rd Unit 111, Danbury, CT 06811

  Coveted single-family style detached condo in desirable Sterling Woods complex. This spacious unit lives like a home only without all the exterior maintenance worries. It features three bedrooms and two and one-half baths. Beautiful front porch entry leads to a two-story foyer bathed in natural light. The open dining/living room features hardwood floors, breakfast bar, gas fireplace and French

  John Casey Coldwell Banker Realty

  111 Logging Trail Rd Unit 111, Danbury, CT 06811
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  /27

  $699,900

  $25K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,655 Sq Ft

  23 Benedict Ave, Fairfield, CT 06825

  ***Buyer could not perform*** Incredible curb appeal defines this classic 3-bedroom, 2-bath New England Cape, ideally situated in a premier Stratfield neighborhood. Step inside to a warm and inviting living room anchored by a charming fireplace, perfect for relaxing or entertaining. The home offers a sun-drenched family room/den, a convenient main-level bedroom, and a sunroom/solarium that opens

  Anthony Fabrizio Coldwell Banker Realty

  23 Benedict Ave, Fairfield, CT 06825
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  /40

  $3,999,999

  • 5 Beds
  • 8 Baths
  • 4,911 Sq Ft

  22 Sturges Commons, Westport, CT 06880

  22 Sturges Commons offers the rare combination of timeless elegance, true neighborhood living, and unmatched convenience in one of Westport's most sought-after locations near the Hunt Club. Just one traffic light to the Greens Farms Station train station, this home makes commuting to New York City effortless while allowing you to return home to a peaceful walking neighborhood where charming

  Judy Michaelis Coldwell Banker Realty

  22 Sturges Commons, Westport, CT 06880
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  /40

  $5,750,000

  • 4 Beds
  • 4.5 Baths
  • 3,800 Sq Ft

  69 Birch Rd, Fairfield, CT 06824

  Your new fully custom near beach luxury residence is ready for you now... Introducing "White Birch", a masterfully executed collaboration between Fairfield County's premier Architect, Builder, & Designer, sets a new benchmark for bespoke coastal living and the effortless estate lifestyle. Every detail has been thoughtfully curated, every finish intentionally elevated, every inch built with

  Jaclyn Picarillo Higgins Group Bedford Square

  69 Birch Rd, Fairfield, CT 06824
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  /40

  $8,650,000

  • 5 Beds
  • 5.5 Baths
  • 5,823 Sq Ft

  82 Arrowhead Way, Darien, CT 06820

  (Don't miss the spectacular waterfront video). On the water in the Tokeneke Association, Short Rocks Manor is poised at the very tip of Arrowhead Way, high above Scotts Cove and Long Island Sound. This breathtaking, updated 1925 English-style stone manor sits on 2.11 acres which includes .362 acres of designated OPEN SPACE. The 5,823 square feet of exquisite craftmanship houses five bedrooms -

  Becky Munro Brown Harris Stevens

  82 Arrowhead Way, Darien, CT 06820
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  /40

  $1,325,000

  $375K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 4,103 Sq Ft

  40 Great Ring Rd, Sandy Hook, CT 06482

  EXCITING NEW LISTING DEVELOPMENT! Now offered independently, with the adjoining land available if desired - two properties, one extraordinary opportunity at 40 Great Ring Road. This modern vision of New England living blends refined architectural character with forward-thinking innovation, energy independence, and sustainable design. The four-bedroom home features a spacious primary suite and

  Stephanie Barnes William Raveis Real Estate

  40 Great Ring Rd, Sandy Hook, CT 06482
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  /33

  $1,299,000

  • 4 Beds
  • 3 Baths
  • 4,316 Sq Ft

  16 Shady Ln, Redding, CT 06896

  Ideal setting and location! This spacious 12 room split level home tucked away on a country lane in the heart of Redding, offers the perfect blend of privacy, charm, and versatility. Set on 3.64 acres, this unique property features a spacious main residence with an open floor plan providing easy living, hardwood floors, an expansive primary suite, in-ground concrete pool, Ironwood deck, and

  Alexis Bennett Coldwell Banker Realty

  16 Shady Ln, Redding, CT 06896
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  /58

  $7,950,000

  • 5 Beds
  • 9 Baths
  • 8,911 Sq Ft

  74 Rock Maple Rd, Greenwich, CT 06830

  Set on four beautifully landscaped acres in Greenwich, 74 Rock Maple Road is a classic Georgian-style residence that blends timeless architecture with exceptional modern amenities. Recently updated with a stunning new kitchen and beautifully renovated bathrooms, the home is designed for both elegant entertaining and comfortable everyday living. Gracious sun-filled interiors, a thoughtful floor

  Jenny Allen Compass Connecticut, LLC

  74 Rock Maple Rd, Greenwich, CT 06830
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  /40

  $650,000

  • 4 Beds
  • 3 Baths
  • 2,286 Sq Ft

  882 Killingworth Rd, Higganum, CT 06441

  Welcome to 882 Killingworth Road, a beautifully updated 4-bedroom, 3-bath Colonial set on two private acres in the heart of Haddam. Offering over 2,200 sq ft of living space, this home blends classic New England charm with modern updates, including refinished hardwood floors and a bright, open layout ideal for everyday living and entertaining. The well appointed kitchen flows seamlessly into the

  Rob Paskiewicz CT Home Pro, LLC

  882 Killingworth Rd, Higganum, CT 06441
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  /36

  $874,999

  $25K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 3,303 Sq Ft

  25 Hillside Dr, Sherman, CT 06784

  A true waterfront retreat with direct frontage on Candlewood Lake, this hidden gem is tucked away behind a perimeter of mature trees, offering a private and peaceful setting within the private Holiday Point Association. The community invites an active lifestyle with scenic opportunities for walking, hiking, and biking. Outdoor living shines here, featuring an expansive 107' x 12' deck and a

  Gary Crawford RE/MAX RISE

  25 Hillside Dr, Sherman, CT 06784

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