Lakeside Woods, CT Homes for Sale

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  /50

  $4,750,000

  $250K PRICE DROP

  • 8 Beds
  • 13 Baths
  • 15,000 Sq Ft

  618 Quaker Hill Rd, Pawling, NY 12564

  Set high atop the storied crest of Quaker Hill, Elmwood Farm is a legacy estate where Hudson Valley history, architectural grandeur, and pastoral beauty converge. Approached by a long, winding gated drive, the property reveals itself gradually across 25.5 rolling acres before arriving at a striking Elizabethan style manor that has stood watch over the surrounding countryside for

  Jake Garay Serhant LLC

  618 Quaker Hill Rd, Pawling, NY 12564
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  /18

  $269,000

  $10K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,025 Sq Ft

  18 Wishing Well Ln Unit 18, New Milford, CT 06776

  Move right into this meticulous townhouse featuring 9 Ft ceilings, 2 car tandem garage and central air. Kitchen has newer appliances. Shining wood-like laminate floors for easy maintenance. Lots of deck space plus private patio. Newer stackable laundry conveniently located near bedrooms. Primary bedroom with walk in closet. Lots of storage. Easy location near shopping, restaurants, downtown etc.

  Joe Chemero Coldwell Banker Realty

  18 Wishing Well Ln Unit 18, New Milford, CT 06776
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  /40

  $719,000

  $31K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,466 Sq Ft

  9 Birch Rd, New Milford, CT 06776

  Welcome home to this beautifully remolded Cape where timeless charm meets exceptional indoor and outdoor living. Inside, thoughtful renovations and quality craftmanship shine throughout offering comfortable living with stylish updates. Expanded dormers have transformed the second level, creating generous living spaces with built-ins and a stunning sunroom filled with natural light in addition to

  Emily Fritz Real Estate By Teresa LLC

  9 Birch Rd, New Milford, CT 06776
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  /40

  $679,900

  $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,974 Sq Ft

  10 Candleview Dr, Sherman, CT 06784

  Welcome to 10 Candleview Drive, a beautifully renovated home in the highly sought-after Deer Run Shores community on Candlewood Lake. Thoughtfully updated from top to bottom, this move-in-ready property offers the perfect blend of modern luxury, lake living, and convenient access to New York City. Step inside to discover a stunning new designer kitchen featuring premium finishes, custom

  Gregory Balek Showcase Realty, Inc.

  10 Candleview Dr, Sherman, CT 06784
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  /16

  $169,500

  $16K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 710 Sq Ft

  470 Danbury Rd Unit 7, New Milford, CT 06776

  Fresh and clean. Main level unit, recent total bathroom renovation , newer kitchen and flooring. Two in-the wall air conditioners, patio door with morning sun. Heat is included in common charges. owner's highest electric bill has been $32 per month. Southern New Milford, a few minutes to Route 7 connector.

  Jehad Sabbagh William Raveis Real Estate

  470 Danbury Rd Unit 7, New Milford, CT 06776
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  /9

  $190,000

  • 1 Bed
  • 1 Bath
  • 625 Sq Ft

  65 West St Unit 404, New Milford, CT 06776

  Welcome to Gaslight Place! This remarkable building, once home to the historic J.S. Halpine Tobacco Warehouse, offers a unique blend of character, charm, and convenient village living. Ideally located within walking distance of the Village Green, where community events are enjoyed throughout the year, you'll be perfectly situated to experience all that this quaint New England town has to offer.

  Patty McManus William Pitt Sotheby's Int'l

  65 West St Unit 404, New Milford, CT 06776
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  /37

  $875,000

  $320K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 2,400 Sq Ft

  131 Route 39 N, Sherman, CT 06784

  Instantly inviting this pristine circa 1940 's classic Connecticut cottage also known as Little Fox Farm is brimming with character and jewel like qualities on nearly 3 acres a wonderful mixture of meadows, light woods, and mature trees as well as stunning perennial flower gardens developed over 30 years by its owner a designer. Set back on the property the house is in mint condition with

  Karen Casey William Pitt Sotheby's Int'l

  131 Route 39 N, Sherman, CT 06784
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  /35

  $425,000

  • Land
  • 33,976 Sq Ft
  • $544,872 per Acre

  21 Candlewood Shore, New Milford, CT 06776

  This exceptional property offers a beautiful blend of level and gently sloping terrain, perfect for designing and building your dream home in a picturesque and highly desirable setting! Perfectly positioned across from Candlewood Lake, the lot captures stunning, year-round water views without the premium of direct waterfront taxes. Enjoy the full lake lifestyle just steps away, with access to a

  Diana Newbert William Raveis Real Estate

  21 Candlewood Shore, New Milford, CT 06776
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  /37

  $14,995,000

  • 4 Beds
  • 3.5 Baths
  • 3,942 Sq Ft

  15 Kirby Hill Rd, Pawling, NY 12564

  Kirby Hill Farm, an exceptional equestrian estate set on 247 acres of Quaker Hill's finest countryside. The turnkey, multi-discipline, equestrian facility offers 4 barns with 81 stalls, 2 indoor riding arenas, 3 outdoor riding rings, 37 paddocks, 7 additional paddocks with winterized waterers, 21 fields, polo field, over 100 acres of fenced property, and 150 acres of riding trails with direct

  Brian McGrath McGrath Realty Inc

  15 Kirby Hill Rd, Pawling, NY 12564
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  /40

  $539,900

  • 3 Beds
  • 2.5 Baths
  • 1,812 Sq Ft

  14 Heather Ct, New Milford, CT 06776

  Joyful living! All-around warm & wonderful, this endearing Colonial captures your eye, heart & spirit! Just right in size & design, it's enhanced by impeccable care, significant updates, and an eye for natural beauty. The uniquely captivating setting offers exceptional privacy, a stunning natural landscape rich in flora & fauna, and colorful perennial gardens. Higher on appeal, lower on

  Carole Sansone William Raveis Real Estate

  14 Heather Ct, New Milford, CT 06776
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  /31

  $660,000

  • 3 Beds
  • 1 Bath
  • 1,061 Sq Ft

  6 Mountain View Ln, New Milford, CT 06776

  A must see! This classic property captures the essence of the Candlewood Lake Club (CLC) experience. As one of the few remaining original cabins, it offers a rare blend of historical charm and authentic lake-living nostalgia, perfectly complemented by the privacy of a quiet, flat lot surrounded by mature landscape. The thoughtful layout-featuring three bedrooms and two full baths on a single

  Erin Porter Coldwell Banker Realty

  6 Mountain View Ln, New Milford, CT 06776
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  /21

  $88,000

  $7K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 720 Sq Ft

  1 Tallow Ln, New Milford, CT 06776

  Welcome to Candle Hill Community in the heart of New Milford! This beautifully remodeled mobile home has been thoughtfully updated throughout, featuring new windows, an updated kitchen, new flooring, and a propane stove for efficient and cozy heating. The fresh updates create a bright, comfortable, and inviting space that is ready for its next owner. Enjoy the charm and convenience of being close

  Marissa Bolmer Berkshire Hathaway NE Prop.

  1 Tallow Ln, New Milford, CT 06776
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  /36

  $1,100,000

  $150K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 3,000 Sq Ft

  35 Skyline Dr, Sherman, CT 06784

  It's All About the Views! REDUCED TO SELL on this one of a kind, custom built contemporary with extraordinary 50 mile views in all directions. Client say make Set in the Lake community of Candlewood Lake Estates, this stately Contemporary, set on a private acre plus an additional lot (.82 acs), at the end of a cul-de-sac, is just waiting for your customization. This incredible setting hosts a 3

  Barbara Sivba Coldwell Banker Realty

  35 Skyline Dr, Sherman, CT 06784
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  /40

  $1,195,000

  • 4 Beds
  • 2.5 Baths
  • 5,353 Sq Ft

  3 Hay Meadow Ln, New Milford, CT 06776

  Set on 2.48 gorgeous, level acres, this spacious 4-bedroom, 3.5-bath center-hall Colonial offers exceptional indoor and outdoor living. Hardwood floors, 9-foot ceilings, neutral finishes and generously sized rooms enhance the main level. The beautifully appointed kitchen features custom white cabinetry, an expansive granite island, tile backsplash, coffee bar, large pantry and casual dining area,

  Kim Kendall Keller Williams Realty

  3 Hay Meadow Ln, New Milford, CT 06776
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  /40

  $895,000

  • 5 Beds
  • 2.5 Baths
  • 3,074 Sq Ft

  8 S Main St, New Milford, CT 06776

  Exceptional opportunity to own a piece of New Milford history just steps from the Town Green. Built in 1900 and extensively renovated in 2020, this award-winning 3,038 SF property features hardwood floors, high ceilings, stained-glass windows, a grand staircase, stone fireplace, wraparound porch, central air, walk-up attic, finished ground-level space with a half bath, and 10 off-street parking

  Thomas Consalvo Tower Realty Corp

  8 S Main St, New Milford, CT 06776
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  /38

  $599,000

  • 3 Beds
  • 2.5 Baths
  • 1,896 Sq Ft

  8 Pinewood Shores, Sherman, CT 06784

  Beautifully maintained, move-in ready +1890 sf raised ranch with a deeded boat dock and private sandy beach in desirable Pinewood Shores at Squantz Pond! Enjoy the best of water-community living with a gorgeous, level yard surrounded by perennial plantings and a spacious deck perfect for outdoor entertaining, dining alfresco or simply relaxing after a day on the water. Light and bright

  Angelina Valentini Coldwell Banker Realty

  8 Pinewood Shores, Sherman, CT 06784
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  /48

  $949,000

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

  36 Sunset New Fairfield Ct Trail, New Fairfield, NY 06812

  Enjoy year-round resort living at Candlewood Isle, one of Candlewood Lake's most sought-after private lake communities. Perfectly sited to capture year-round breathtaking western exposure and unforgettable sunsets, this move-in ready, one-level-living ranch offers +2,260 square feet of beautifully maintained living space in total with spectacular lake views. The inviting open floor plan is

  Angelina Valentini Coldwell Banker Realty

  36 Sunset New Fairfield Ct Trail, New Fairfield, NY 06812
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  /19

  $1,180,000

  $20K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 800 Sq Ft

  18 Orchard Beach Rd, Sherman, CT 06784

  DIRECT WATERFRONT, rarely available, LAKEFRONT HOME ON CANDLEWOOD LAKE - SHERMAN, CT Experience the best of lakefront living in this charming 3-bedroom, 1 bath home nestled on a private .43- acre lot. An adjacent .63-acre wooded, sloping lot is included. New kitchen with new appliances and new bathroom. New washer and dryer and hot water tank. Located on a cul-de-sac and next to Orchard Beach.

  Derek Greene Derek Greene

  18 Orchard Beach Rd, Sherman, CT 06784
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  /40

  $699,999

  $49K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,488 Sq Ft

  34 Hardscrabble Rd, Sherman, CT 06784

  Welcome home to this exceptional 4-bedroom, 3.5-bath Custom Colonial nestled on 4.5 scenic acres in sought-after Sherman. Featuring an expansive wraparound covered porch, a beautifully updated kitchen with stone countertops, and an inviting den with a fireplace, every space is designed for comfortable living and effortless entertaining. Upon entering, you'll find a flexible main-level suite that

  Lisa Weisenberger Luks Realty

  34 Hardscrabble Rd, Sherman, CT 06784
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  /11

  $225,000

  • Land
  • 8.44 Acres
  • $26,659 per Acre

  14 Akindale Rd, Pawling, NY 12564

  Discover the opportunity to build your custom home on this exceptional 8.44-acre homesite in Brady Brook Falls, an established community of estate properties nestled in Pawling's scenic countryside. Offering a beautiful mix of open areas and mature woodlands, the property provides a peaceful setting with plenty of space to create the home you've envisioned. Much of the preparation has already

  Debra Allan BHHS Hudson Valley Properties

  14 Akindale Rd, Pawling, NY 12564
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  /39

  $819,000

  $46K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 2,996 Sq Ft

  3 Old Forest Rd, Sherman, CT 06784

  The Lake Experience! Candlewood Lake Estates, a private gated community on Lake Candlewood hosts this 1998 built, 3 bedroom, 2 bath contemporary with 2 dramatic stone, floor to ceiling fireplaces, gleaming hardwood floors, new 2 car garage with loft and fabulous wrap deck to enjoy the private yard & seasonal views! An idyllic weekend.summer retreat or full time residence, this home exudes a

  Barbara Sivba Coldwell Banker Realty

  3 Old Forest Rd, Sherman, CT 06784
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  /2

  $69,000

  • Land
  • 20,037 Sq Ft
  • $150,000 per Acre

  11 Southeast Trail, New Milford, CT 06776

  Vacate wooded lot.

  Daniele Amelia Global Realty

  11 Southeast Trail, New Milford, CT 06776
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  /36

  $1,195,000

  $100K PRICE DROP

  • 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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  /39

  $700,000

  • 5 Beds
  • 3 Baths
  • 2,004 Sq Ft

  27 Town Farm Rd, New Milford, CT 06776

  Fully rebuilt in 2026 - Better than New Construction! 5 bed-3 full marble baths w/ New 5Br septic. 3 miles from Candlewood Lake. Home boasts 2 en-suite bedrms & potential for multi-gen living. Main level features solid bamboo floors throughout, stunning NEW Kitchen w/ new cabinets, quartz tops, glass backsplash, S/S LG Signature appliances: dual fuel, double ovens, gas cooktop, French door

  Michael Bachmann HomeSmart Homes and Estates

  27 Town Farm Rd, New Milford, CT 06776
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  /39

  $1,345,000

  • 4 Beds
  • 6 Baths
  • 6,052 Sq Ft

  32 Sail Harbour Dr, New Fairfield, CT 06812

  A New Look! Grand Colonial in Sail Harbour Club, on Candlewood Lake, sits majestically on 1.13 acs offering 4/5 BRS, 6 Baths,4 car garage plus an expansive yard w/seasonal lake views. Spacious rooms, hardwood floors & a center isle kitchen w/coffee bar & breakfast nook topped with new quartz counters. A flex floor plan offers a private living room, w/hardwood can double as an office or library. A

  Barbara Sivba Coldwell Banker Realty

  32 Sail Harbour Dr, New Fairfield, CT 06812
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  /40

  $999,900

  • 4 Beds
  • 3.5 Baths
  • 3,744 Sq Ft

  1 Elwell Rd, New Fairfield, CT 06812

  Built just two years ago, this stunning modern farmhouse blends timeless design with thoughtful finishes and quality craftsmanship throughout. A welcoming front porch and custom front door set the tone as you enter into a bright, open interior featuring 9-foot ceilings, abundant natural light, wide-plank oak hardwood floors, matte gold fixtures, and an inviting layout designed for modern living.

  Cory Neumann Houlihan Lawrence

  1 Elwell Rd, New Fairfield, CT 06812
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  /6

  $260,000

  • Land
  • 2.25 Acres
  • $115,556 per Acre

  56 Hubbell Mountain Rd, Sherman, CT 06784

  Wooded land.

  John Sniffen William Pitt Sotheby's Int'l

  56 Hubbell Mountain Rd, Sherman, CT 06784

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