Fairfield County CT Homes for Sale with Acreage

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  /49

  $100,000,000

  • 8 Beds
  • 14 Baths
  • 13,163 Sq Ft

  108 Cedar Cliff Rd, Riverside, CT 06878

  Perched in timeless elegance atop an expansive 2.91-acre gated peninsula, with best-in-class views of the Manhattan skyline and the shimmering Long Island Sound, Cedar Cliff is a Mediterranean villa of unrivaled pedigree and commanding presence. Privately situated along a secluded road within Riverside's prestigious Indian Head Association, this storied property occupies the historic grounds of

  Leslie McElwreath Sotheby's International Realty

  108 Cedar Cliff Rd, Riverside, CT 06878
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  /22

  $6,650,000

  Coming Soon

  • 6 Beds
  • 9 Baths
  • 8,274 Sq Ft

  33 Boulder Brook Rd, Greenwich, CT 06830

  Absolutely stunning 6 bedroom, 7 bathroom home in a beautiful setting on a peaceful and private cul-de-sac with a long drive enticing you to the front door. Embrace the tranquility of the landscaped backyard with pool and terraced areas, perfect for entertaining or relaxing. Sunlit gourmet kitchen overlooking the pool and back lawn. Savor morning coffee in the sun drenched living area. Beautiful

  Alison Jones Brown Harris Stevens CT, LLC

  33 Boulder Brook Rd, Greenwich, CT 06830
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  /40

  $1,975,000

  • 4 Beds
  • 3 Baths
  • 3,253 Sq Ft

  5 Tanglewood Ln, Westport, CT 06880

  Set on a quiet, convenient street in Westport's coveted Old Hill, this charming home captures the essence of Fairfield County living. A picturesque acre with level lawns, a sparkling pool, and expansive patios creates an exceptional outdoor retreat ideal for relaxing or entertaining. A welcoming front porch leads into a thoughtfully renovated interior with beautifully proportioned spaces and

  Doug Bross Coldwell Banker Realty

  5 Tanglewood Ln, Westport, CT 06880
• 

  

  

  /41

  $800,000

  • 4 Beds
  • 2.5 Baths
  • 3,277 Sq Ft

  754 Milltown Rd, Brewster, NY 10509

  The Crown Jewel of Milltown Road! Enter through stone pillars accented by a beautiful white picket fence! Set on three private, level, landscaped acres along the Brewster/Danbury border, this custom-built Colonial offers a rare blend of seclusion, convenience, and long-term value—enhanced by the advantage of Danbury taxes. Meticulously built and maintained by its current owners, this home is

  Filiz Dalo Coldwell Banker Realty

  754 Milltown Rd, Brewster, NY 10509
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  /39

  $3,350,000

  • 5 Beds
  • 5.5 Baths
  • 5,789 Sq Ft

  221 Greens Farms Rd, Westport, CT 06880

  The Bedford House: Architecturally and historically significant estate in Greens Farms. This exceptional property offers a rare opportunity to own one of Westport's true gems with a remarkable provenance. Set on 2.33 acres with a gunite pool & spa, court and a 2400 SF barn w/ 3 car garage, loft and more, this estate blends timeless elegance with modern comfort. Originally built in 1904 and

  Patricia Shea Coldwell Banker Realty

  221 Greens Farms Rd, Westport, CT 06880
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  /36

  $1,250,000

  $25K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 3,713 Sq Ft

  98 Hopewell Woods Rd, Redding, CT 06896

  Custom-built in 2004 and meticulously maintained, this 2.18-acre home offers a true escape from the everyday. Surrounded by perennial gardens, stone walls, and specimen trees, the grounds are anchored by a stunning stone patio-your own private sanctuary for quiet mornings or lively entertaining. Inside, discover 3,669 square feet of sun-drenched living space featuring 11 rooms, 4 bedrooms, and

  Paul Gervais William Pitt Sotheby's Int'l

  98 Hopewell Woods Rd, Redding, CT 06896
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  /37

  $1,350,000

  Open Sun 1PM - 3PM

  • 4 Beds
  • 3.5 Baths
  • 3,500 Sq Ft

  118 Davenport Ridge Ln, Stamford, CT 06903

  Set on a quiet North Stamford cul-de-sac, this beautifully updated ranch offers effortless one-level living with a 2016 addition that created a serene primary suite complete with a sitting area, walk-in closet, and spa-like bath with heated floors and a steam shower. Enjoy a private backyard retreat and the space, comfort, and lifestyle that make North Stamford so desirable.

  Maria Bardelli Douglas Elliman of Connecticut

  118 Davenport Ridge Ln, Stamford, CT 06903
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  /2

  $5,980,000

  New Construction

  • 6 Beds
  • 9 Baths
  • 10,521 Sq Ft

  21 Sturges Commons, Westport, CT 06880

  NEW CONSTRUCTION TO BE BUILT IN THE COVETED HUNT CLUB NEIGHBORHOOD - Renowned, luxury builder Mattera Construction is well-known for architecturally significant & stunning modern homes filled with elegance, timeless beauty, custom interiors with state-of-the-art amenities. Now offering a perfectly designed 6 bedroom home finished on 4 levels filled with elegant finishes, well sited on a quiet

  Patricia Shea Coldwell Banker Realty

  21 Sturges Commons, Westport, CT 06880
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  /9

  $1,869,000

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 4,457 Sq Ft

  20 Flat Rock Dr, Ridgefield, CT 06877

  Location is everything-and this one delivers. Nestled on a quiet cul-de-sac in the sought-after West Lane section of Ridgefield, this property offers the ultimate combination of privacy, neighborhood charm, and unmatched convenience. Just 15 minutes to the Katonah Metro-North line, one hour to NYC by car, minutes to downtown New Canaan, Ridgefield & nearby NY/CT state parks, this is one of the

  Kyle Neumann Houlihan Lawrence

  20 Flat Rock Dr, Ridgefield, CT 06877
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  /36

  $870,000

  $80K PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 4,080 Sq Ft

  2 Abbey Ln, Newtown, CT 06470

  Extensively updated and thoughtfully expanded, this spacious Colonial offers over 4,000 square feet of flexible living space designed for today's evolving lifestyle needs. With five bedrooms and 4.5 baths, including two private primary suites on separate levels, the home is ideally suited for multigenerational living, long-term guests, au pair accommodations, or work-from-home flexibility. The

  Lynda Linley Coldwell Banker Realty

  2 Abbey Ln, Newtown, CT 06470
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  /2

  $325,000

  • Land
  • 2.46 Acres
  • $132,114 per Acre

  6 Vona Way, Newtown, CT 06470

  Welcome to one of Newtown, CT's most stunning hidden gems - an absolutely beautiful private 2.46 acre lot nestled on a cul-de-sac in one of the region's most sought after subdivisions. This is your chance to craft the home of your dreams in an exclusive, upscale community. Surrounded by gorgeous homes & plenty of nature, the community offers a lavish lifestyle that combines luxury and

  Anthony Fabrizio Coldwell Banker Realty

  6 Vona Way, Newtown, CT 06470
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  /35

  $699,900

  • 3 Beds
  • 2.5 Baths
  • 1,536 Sq Ft

  8 Stony Brook Rd, Brookfield, CT 06804

  Tucked along a quiet stretch of Brookfield, 8 Stony Brook Road tells a story that feels both grounded and elevated-a home where everyday living meets thoughtful design. From the moment you arrive, there's a sense of balance. A modern split-level, welcomes you with clean lines and a warm, inviting presence. Step inside, and the heart of the home reveals itself-an updated, modern kitchen where

  Maria Capela BHGRE Gaetano Marra Homes

  8 Stony Brook Rd, Brookfield, CT 06804
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  /36

  $1,295,000

  • 4 Beds
  • 3.5 Baths
  • 3,308 Sq Ft

  145 Pine Hill Rd, New Fairfield, CT 06812

  Welcome to 145 Pine Hill Rd. A renovated Organic Modern home mixing both modern amenities and rustic charm. Adorned with random plank flooring, hand-hewn beams and massive field stone fireplace. The 12ft sliders in the Living Room allow for access onto the spacious deck. The culinary space is a chef's haven, equipped with state-of-the-art appliances & premium finishes that inspire culinary

  Cheryl Finley Coldwell Banker Realty

  145 Pine Hill Rd, New Fairfield, CT 06812
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  /2

  $5,650,000

  New Construction

  • 7 Beds
  • 9 Baths
  • 8,762 Sq Ft

  8 Pleasant Valley Ln, Westport, CT 06880

  Experience modern luxury in this new SIR SIGNATURE Home by SIR Development, Westport's premier builder. Set on 1.02 private acres on a coveted culdesac, this home offers a striking approach, 3car garage, and rare backyard privacy, all within walking distance to Bedford Middle, Staples High, Wakeman Fields, and Town Farm. A fresh contemporary aesthetic features a dramatic twostory foyer, 10ft

  Doug Bross Coldwell Banker Realty

  8 Pleasant Valley Ln, Westport, CT 06880
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  /34

  $7,495,000

  • 6 Beds
  • 11 Baths
  • 7,528 Sq Ft

  229 Umpawaug Rd, Redding, CT 06896

  Welcome to 229 Umpawaug Road, the quintessential estate of exceptional quality on the premier scenic road in Redding, Connecticut in Fairfield County. Surround yourself in luxury inside this sun-filled 6 bedroom, 11 bathroom, 6 fireplaces center hall colonial with a flowing floor plan, formal and informal rooms, embracing the incredibly private 6.5 acres of hand-stacked walls, privacy gates and

  Stacy Young William Raveis Real Estate

  229 Umpawaug Rd, Redding, CT 06896
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  /40

  $4,750,000

  • 6 Beds
  • 6.5 Baths
  • 6,829 Sq Ft

  234 Brookside Rd, Darien, CT 06820

  Set along a picturesque stretch in one of Darien's most sought-after neighborhoods, 234 Brookside Road offers a rare blend of timeless architecture, privacy, and modern comfort. Surrounded by mature trees and beautifully landscaped grounds, this exceptional property provides a serene, retreat-like setting just minutes from town, top-rated schools, and the coastline. This HOBI award-winning

  Kristin Nemec William Pitt Sotheby's Int'l

  234 Brookside Rd, Darien, CT 06820
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  /15

  $6,995,826

  New Construction

  • 6 Beds
  • 10 Baths
  • 8,417 Sq Ft

  24 Edgemarth Hill Rd, Westport, CT 06880

  This Beauty will be ready Summer 2026! Construction of this 8,417SF dream residence with pool and spa on 1 private acre in coveted Greens Farms, Westport, is in full swing. 24 Edgemarth Hill was designed and will be crafted and appointed with the finest materials - see rendering photos of what's to come. Flaunting sexy floor-to-ceiling walls of windows, stone and textured accents, vaulted

  Jaclyn Picarillo Higgins Group Bedford Square

  24 Edgemarth Hill Rd, Westport, CT 06880
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  /7

  $10,650,000

  New Construction

  • 6 Beds
  • 8 Baths
  • 9,100 Sq Ft

  11 Dogwood Ln, Westport, CT 06880

  Another extraordinary masterpiece by Coastal Luxury Homes, ideally situated in one of Westport's premier neighborhoods. Spanning over 9000 square feet of living space this 6 bedroom estate is defined by bold architectural lines, chic designer interiors, expansive balconies and seamless indoor-outdoor living. A resort caliber pool, fully equipped outdoor kitchen, and lush manicured grounds

  Jen Kass Higgins Group Bedford Square

  11 Dogwood Ln, Westport, CT 06880
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  /2

  $295,000

  • Land
  • 2.96 Acres
  • $99,662 per Acre

  195 Candlewood Rd, Stratford, CT 06614

  Rare Level Lot at end of street. 400 feet of frontage along the 2nd hole at Black Hawk Country Club. Build your dream home. No restrictions on house size. Over 2 acres of dry buildable land. Beautiful views.

  David D. D'Ausilio Discount Listing Center

  195 Candlewood Rd, Stratford, CT 06614
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  /27

  $579,000

  $66K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,472 Sq Ft

  178 Church St, Monroe, CT 06468

  Blending a perfect combination of privacy, modern updates, appealing floorplan, and convenient location - 178 Church Street is ready to fulfill its next owner's every need. Before even stepping inside, you'll find yourself on a stunning picturesque 1.25 acre lot, lined with trees and a stream at the rear. At the end of the expansive, recently repaved driveway sits an oversized detached 2 car

  John Nigro Keller Williams Realty Prtnrs.

  178 Church St, Monroe, CT 06468
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  /7

  $10,350,000

  $500K PRICE DROP

  • 6 Beds
  • 8 Baths
  • 7,072 Sq Ft

  12 Woodside Rd, Greenwich, CT 06830

  DEER PARK WOODSIDE: This distinguished 1930's brick Georgian is set on a serene, oversized lot within Deer Park Association, embodying the timeless architectural presence of a classic pre-war brick manor. Originally designed as an elegant six-bedroom, six-bath residence, the home offers an exciting opportunity to be reimagined for its next chapter. The exceptional grounds unfold across expansive,

  Leslie McElwreath Sotheby's International Realty

  12 Woodside Rd, Greenwich, CT 06830
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  /9

  $369,000

  • Land
  • 2 Acres
  • $184,500 per Acre

  B Bridge Rd, Weston, CT 06883

  Rare oppotunity to purchase a magical 2 acre parcel of land w/ a little slice of frontage on Aspetuck River in coveted Stonybrook Association. Beautiful lot with fabulous views in true lower Weston on Westport border! Stonybrook is a unique enclave of homes in Weston and offers swimming, boating, tennis, zipline, basketball court, playground, picnic benches and more, all for the use of homeowners

  Carrie Shea Camelot Real Estate

  B Bridge Rd, Weston, CT 06883
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  /39

  $1,395,000

  • 3 Beds
  • 2 Baths
  • 1,747 Sq Ft

  89 Wood Creek Rd, New Fairfield, CT 06812

  One-of-a-Kind Lakefront Retreat on Candlewood Lake - 14+ Acres of Pure Privacy & Panoramic Views. Perched high above Candlewood Lake on pristine woodland, this truly exceptional lake cottage offers an unmatched combination of direct waterfront access, total privacy, & sweeping 180-degree lake views. The home is a nature lover's dream. Meander down a private wooded trail & steps to your secluded

  Cory Neumann Houlihan Lawrence

  89 Wood Creek Rd, New Fairfield, CT 06812
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  /2

  $4,999,999

  • Land
  • 17 Acres
  • $294,118 per Acre

  2 A Owenoke Park, Westport, CT 06880

  The property consists of 17 waterfront acres including a 7 acre upland section.

  Ralph Harvey ListWithFreedom.com

  2 A Owenoke Park, Westport, CT 06880
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  /28

  $2,195,000

  $200K PRICE DROP

  • 6 Beds
  • 4.5 Baths
  • 10,746 Sq Ft

  677 W Hill Rd, Stamford, CT 06902

  Rare 3.75-Acre Builder Opportunity on W Hill Road Exceptional opportunity to own 3.75 private acres in one of the area's most prestigious and sought-after locations-W Hill Road. This unique property features an existing 4,400 sq ft main residence plus a separate 900 sq ft cottage, offering endless possibilities for builders, investors, or end-users seeking a private estate setting. The current

  Antonio LaRocca The LaRocca Group

  677 W Hill Rd, Stamford, CT 06902
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  /39

  $13,100,000

  • 6 Beds
  • 8 Baths
  • 10,286 Sq Ft

  7 Parsonage Rd, Greenwich, CT 06830

  SUMMER FUN BEGINS HERE! An extraordinary newly constructed residence in the heart of Greenwich,7 Parsonage Road is a masterfully crafted white brick manor on 1.12 acres, defined by timeless elegance and modern sophistication. Spanning four expansive light filled levels served by an elevator, this six-bedroom, six full and two half-bathroom home offers over 10,200+/- square feet of meticulously

  Leslie McElwreath Sotheby's International Realty

  7 Parsonage Rd, Greenwich, CT 06830
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  /43

  $2,299,000

  • 5 Beds
  • 3.5 Baths
  • 2,956 Sq Ft

  42 Stone Brook Ln, Cos Cob, CT 06807

  Tucked at the end of a peaceful cul-de-sac in Cos Cob, within the coveted North Street School district, this serene 5-bedroom home (featuring a main-level en-suite) offers a tranquil escape. Contemporary design shines through vaulted ceilings, skylights, and sun-drenched interiors that flow seamlessly to a large screened-in porch and an expansive 900 sq ft wraparound deck with private wooded

  Cora Lynch-O'Meara Brown Harris Stevens CT, LLC

  42 Stone Brook Ln, Cos Cob, CT 06807
• 

  /2

  $3,100,000

  • 4,311 Sq Ft

  Unlisted Address

  Imagine the possibilities! From residential to commericial opportunities this waterfront parcel is ideally poised for transformation into luxurious waterfront and water-view condominiums, townhomes or apartments. Alternatively, retain the existing turnkey and profitable establishment with income producing tenants while allowing the property to appreciate overtime. Just over the creek abutting

  Susan Vanech Compass Connecticut, LLC

  Unlisted Address
• 

  

  /39

  $949,000

  • 4 Beds
  • 2.5 Baths
  • 4,168 Sq Ft

  170 Whippoorwill Ln, Stratford, CT 06614

  Welcome to 170 Whippoorwill Lane In Stratford's desirable Putney neighborhood. This property overlooking the Mill River Country Club golf course is seated well above the road on a rare 3.53 acre lot providing park-like grounds and plenty of privacy. There are 12 rooms, 4100 square feet and 9 foot ceilings throughout. Approaching the home via a long shared driveway, you are welcomed by a parking

  Emily O'Connor Karolyi Century 21 AllPoints Realty

  170 Whippoorwill Ln, Stratford, CT 06614
• 

  

  /20

  $3,150,000

  • 4 Beds
  • 4.5 Baths
  • 5,185 Sq Ft

  19 Richards Ln, New Canaan, CT 06840

  ALL OFFERS TO BE RECEIVED BY NOON (12:00) ON FRIDAY THE 15TH. Ideally located close to schools and Waveny Park, this updated Colonial is set on 1.34 private acres at the end of a secluded lane. An open floor plan with abundant windows and doors fills the home with natural light and creates seamless access to a terrace and expansive, level backyard. Featuring a spacious primary suite, generous

  Wendy Dixon Fog Houlihan Lawrence

  19 Richards Ln, New Canaan, CT 06840
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  /40

  $1,700,000

  • 5 Beds
  • 3.5 Baths
  • 5,079 Sq Ft

  23 Norton Rd, Easton, CT 06612

  Experience the best of both worlds in Easton, where luxury, comfort, and timeless elegance meet unmatched privacy, just minutes from the vibrant downtowns of Westport and Fairfield. Enjoy a refined lifestyle with space to breathe, while staying effortlessly connected to top dining, shopping, beaches, train stations, and a direct commute to New York City. Set on a quiet lane in Lower Easton, this

  Julie Vanderblue Higgins Group Real Estate

  23 Norton Rd, Easton, CT 06612
• 

  

  /40

  $754,900

  • 3 Beds
  • 2 Baths
  • 2,300 Sq Ft

  153 Everett Rd, Easton, CT 06612

  Well maintained home in lower Easton on 1.6 park-like acres of level land with extensive landscaping and mature trees backing up to open space. Inside has an open floor plan with large family room with vaulted ceilings and plenty of natural light at the center of the home. Kitchen offers a large gas viking stove perfect for the home chef as well as plenty of cabinet space, separate dining area

  Steven Lage Coldwell Banker Realty

  153 Everett Rd, Easton, CT 06612
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  /31

  $1,290,000

  • 5 Beds
  • 4.5 Baths
  • 5,169 Sq Ft

  29 Alpine Rd, Monroe, CT 06468

  Tucked away in one of Fairfield County's most desirable suburban settings, this exceptional property offers over 4,000 square feet of beautifully designed living space including an in-law apartment. The main house includes 4 bedrooms and 2.5 bathrooms, with an incredible combination of comfort, flexibility, and outdoor living. From the moment you arrive, the impressive 4-car garage, expansive

  Michael Dziedzic Precision Realty LLC

  29 Alpine Rd, Monroe, CT 06468
• 

  

  /39

  $1,825,000

  • 5 Beds
  • 6 Baths
  • 4,595 Sq Ft

  140 Signal Hill Rd, Wilton, CT 06897

  Tucked away on 2.18 private acres, this beautifully designed 5-bedroom, 6-bathroom home offers exceptional space, natural light, and a layout ideal for both everyday living and entertaining. Discover hardwood floors and a thoughtfully designed main level. The open kitchen flows seamlessly into the family room, anchored by a fireplace that creates a warm gathering space. A sun-filled den with a

  Mayra Cardenas Mayorga Berkshire Hathaway NE Prop.

  140 Signal Hill Rd, Wilton, CT 06897
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  /29

  $1,995,000

  • 4 Beds
  • 3.5 Baths
  • 3,546 Sq Ft

  86 Dandy Dr, Cos Cob, CT 06807

  Discover charming, single-level living with incredible space! This classic ranch offers over 2,100 sq. ft. on the main floor, featuring a gracious living room with fireplace, formal dining, and a sunny, open-concept kitchen and family room, plus 4 nicely sized bedrooms. The large screened-in porch offers seamless indoor-outdoor living. Convenience is key with a dedicated laundry/powder room off

  Charles Magyar William Raveis Real Estate

  86 Dandy Dr, Cos Cob, CT 06807
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  /38

  $1,699,000

  $139K PRICE DROP

  • 4 Beds
  • 5 Baths
  • 5,385 Sq Ft

  7 Long Meadow Ln, Redding, CT 06896

  Sweeping meadow views, privacy & sunsets from an elevated setting 7 Long Meadow Lane is a distinctive property defined by its scale, setting, and versatile layout, offering generous proportions and an architectural presence that supports a wide range of lifestyles. Sited on an elevated, scenic 4.39 acres with exceptional privacy and open meadow outlooks, the home enjoys a peaceful setting

  Linda Sweeny William Raveis Real Estate

  7 Long Meadow Ln, Redding, CT 06896
• 

  

  /14

  $475,000

  • 3 Beds
  • 2 Baths
  • 1,469 Sq Ft

  21 High Bridge Rd, Sandy Hook, CT 06482

  Welcome to 21 High Bridge Road, a rare Sandy Hook gem where classic New England charm meets peaceful country living on 3 acres. This inviting colonial instantly feels like home with its timeless curb appeal, expansive covered front porch, and warm character throughout. Step inside and you're welcomed by a layout that balances charm, functionality, and space. To one side, a spacious formal dining

  Mark Mermelstein eXp Realty

  21 High Bridge Rd, Sandy Hook, CT 06482
• 

  

  /39

  $1,149,000

  $51K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 4,420 Sq Ft

  15 Mountain View Dr, Weston, CT 06883

  Reminiscent of an European Estate this 4420 square-foot home features, four bedrooms, two full bathrooms and two half bathrooms on an open acre of land. It's extensive outdoor patio and entertainment areas wrap around the rear of the property, a cobblestone lined driveway, and specimen landscaping are all situated on a cul-de-sac in an easy to get to everything location. The gourmet kitchen

  Peter Hastings Hastings Real Estate

  15 Mountain View Dr, Weston, CT 06883
• 

  

  /25

  $800,000

  $50K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 3,788 Sq Ft

  95 Wildwood Dr, Stratford, CT 06614

  Welcome home to 95 Wildwood Drive! This meticulously maintained Colonial offers 2,388 sq ft above grade plus an additional 1,400 sq ft of finished lower-level space, all just minutes from Rt. 8 and Rt. 15, as well as nearby restaurants, Jones Family Farms, and Two Roads Brewery. The home features 4 bedrooms, 2.5 bathrooms, flexible options for dedicated home offices, a formal dining room, and a

  Matthew Boateng Coldwell Banker Realty

  95 Wildwood Dr, Stratford, CT 06614

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