Watertown, CT Homes

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  /21

  $549,000

  $50K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 962 Sq Ft

  2581 Litchfield Rd, Watertown, CT 06795

  Cottage with post and beam Barn with loft on 15+ acres. Fields, woods, small pond, farm. Barn is 24x 36 overall and has 2 box stalls and a straight stall, hay or other storage a wash stall, and a finished loft apartment with kitchen, living areas, bedroom and bathroom. Options include practicing agriculture, hunting, relaxing and building an estate. Additional land available for a house. See MLS

  Vincent Gualtieri Town & Country Real Estate

  2581 Litchfield Rd, Watertown, CT 06795
• 

  $300,200

  Sold Jan 30, 2026

  464 French St, Oakville, CT 06779

  • 3 Beds
  • 1 Bath
  • 1,252 Sq Ft
  • Built 1963

  Last Sold Summary

  • 18% Below List Price
  • $240/SF
  • 89 Days On Market

  Current Estimated Value $380,764

  Last Listing Agent Margaret Shea William Raveis Real Estate

  464 French St, Oakville, CT 06779
• 

  Est $349,729

  Not Listed For Sale

  45 Pleasantview St, Oakville, CT 06779

  • 3 Beds
  • 2 Baths
  • 1,700 Sq Ft
  • Built 1941

  45 Pleasantview St, Oakville, CT 06779

  Last Sold Summary

  • 91 Days On Market

  Last Listing Agent Tim Drakeley Drakeley Real Estate, Inc.
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  /32

  $874,900

  • 4 Beds
  • 2.5 Baths
  • 3,528 Sq Ft

  193 Stoney Brook Ln, Watertown, CT 06795

  Nestled at the end of a long, private driveway on a quiet cul-de-sac, this custom-built colonial has been a private treasure - until now. Set on nearly 5 acres of lush, wooded land near the Litchfield border, this distinguished four-bedroom home spans just over 3,500 square feet of thoughtfully designed living space in one of the area's most sought-after neighborhoods. Lovingly maintained since

  Sarah Hull Coldwell Banker Realty

  193 Stoney Brook Ln, Watertown, CT 06795
• 

  $245,000

  Sold Dec 19, 2025

  245 Cherry Ave Unit I15, Watertown, CT 06795

  • 3 Beds
  • 1.5 Baths
  • 1,296 Sq Ft
  • Built 1968

  Last Sold Summary

  • $189/SF
  • 40 Days On Market

  Current Estimated Value $257,416

  Last Listing Agent Victor Santana Santana Realty Group LLC

  245 Cherry Ave Unit I15, Watertown, CT 06795
• 

  Est $231,234

  Not Listed For Sale

  148 Sunnyside Ave, Oakville, CT 06779

  • 2 Beds
  • 1 Bath
  • 784 Sq Ft
  • Built 1930

  148 Sunnyside Ave, Oakville, CT 06779

  Last Sold Summary

  • 137 Days On Market

  Last Listing Agent Sharon Parziale Appletown Realty Inc.
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  /39

  $459,900

  Under Contract

  • 3 Beds
  • 2 Baths
  • 1,760 Sq Ft

  15 Fieldwood Dr, Watertown, CT 06795

  This updated, well maintained home, located on a quiet cul de sac, with a fenced in yard is now ready for new owners. The main level features a kitchen/dining room that flows to the living room. The large living room features a gas fireplace, wood floor and bay window. The sliders off the dining area lead to an expansive deck with gazebo. Three bedrooms and a full bath complete this level. The

  Dorothy Beckley D. Beckley Realty

  15 Fieldwood Dr, Watertown, CT 06795
• 

  $353,000

  Sold Apr 16, 2026

  301 Winslow Dr, Watertown, CT 06795

  • 2 Beds
  • 2.5 Baths
  • 1,448 Sq Ft
  • Built 1992

  Last Sold Summary

  • 1% Above List Price
  • $244/SF
  • 9 Days On Market

  Current Estimated Value $356,752

  Last Listing Agent Lynn LaForme Regency Real Estate, LLC

  301 Winslow Dr, Watertown, CT 06795
• 

  Est $338,718

  Not Listed For Sale

  277 Buckingham St, Oakville, CT 06779

  • 3 Beds
  • 2 Baths
  • 1,912 Sq Ft
  • Built 1945

  277 Buckingham St, Oakville, CT 06779

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Amy Bartolucci Coldwell Banker Realty
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  /35

  $395,000

  Coming Soon

  • 4 Beds
  • 2 Baths
  • 1,442 Sq Ft

  77 Jenta Ln, Watertown, CT 06795

  Welcome to this spacious Cape-style home, ideally situated in one of the towns sought-after subdivisions. A covered front porch with Trex-style decking adds welcoming curb appeal. As you enter the home, you're welcomed into the living room, where a beautiful stone-faced fireplace with a raised stone hearth and built-in cast-iron wood-burning insert creates a warm and inviting focal point. From

  David Aurigemma Regency Real Estate, LLC

  77 Jenta Ln, Watertown, CT 06795
• 

  $295,000

  Sold Nov 13, 2025

  108 Cannon Ridge Dr Unit 108, Watertown, CT 06795

  • 2 Beds
  • 2 Baths
  • 1,110 Sq Ft
  • Built 1987

  Last Sold Summary

  • 6% Below List Price
  • $266/SF
  • 70 Days On Market

  Current Estimated Value $314,178

  Last Listing Agent Paula Basso Evjen Agency

  108 Cannon Ridge Dr Unit 108, Watertown, CT 06795
• 

  Est $302,232

  Not Listed For Sale

  21 Hazel St, Oakville, CT 06779

  • 4 Beds
  • 1 Bath
  • 1,044 Sq Ft
  • Built 1940

  21 Hazel St, Oakville, CT 06779

  Last Sold Summary

  • 65 Days On Market

  Last Listing Agent Sandra Deschenes Fercodini Properties, Inc.
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  /26

  $399,900

  $40K PRICE DROP Pending

  • 4 Beds
  • 3.5 Baths
  • 1,496 Sq Ft

  15 Monroe St, Oakville, CT 06779

  Located in a quiet Watertown, CT neighborhood just minutes from shopping, dining, and major conveniences, this 4-bedroom, 2.5-bath home offers space and flexibility. The upper level features a bright kitchen, dining area, and a spacious family room with skylights that fill the home with natural light, along with three generously sized bedrooms, a full bath, and a half bath in the primary bedroom.

  Tom Dorso Mapleridge Realty

  15 Monroe St, Oakville, CT 06779
• 

  $330,000

  Sold Nov 25, 2025

  1301 Winslow Dr, Watertown, CT 06795

  • 2 Beds
  • 2.5 Baths
  • 1,952 Sq Ft
  • Built 1990

  Last Sold Summary

  • 2% Above List Price
  • $169/SF
  • 0 Days On Market

  Current Estimated Value $352,052

  Last Listing Agent Jennifer Bundock Coldwell Banker Realty

  1301 Winslow Dr, Watertown, CT 06795
• 

  Est $374,105

  Not Listed For Sale

  16 Chestnut Grove Rd, Watertown, CT 06795

  • 3 Beds
  • 1.5 Baths
  • 1,598 Sq Ft
  • Built 1898

  16 Chestnut Grove Rd, Watertown, CT 06795

  Last Sold Summary

  • 36 Days On Market

  Last Listing Agent Christina Zainc BHGRE Gaetano Marra Homes
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  /14

  $3,668,000

  Pending

  • 7 Beds
  • 3 Baths
  • 2,688 Sq Ft

  805 Main St, Watertown, CT 06795

  Rare opportunity to acquire a well-maintained 28-unit multifamily portfolio spanning 8 buildings across 4 tax parcels in Watertown, CT. The portfolio includes 15 Pythian Ave, 20 Pythian Ave, 28, 38, 48, 58 and 68 Atwood Court, and 805 Main St. Under single ownership for five years, the current owner has completed significant capital improvements including new roofs, siding, and porches

  Levi Judqin Brass Moon Realty

  805 Main St, Watertown, CT 06795
• 

  $390,000

  Sold Nov 11, 2025

  33 Mallory Rd, Watertown, CT 06795

  • 4 Beds
  • 2 Baths
  • 1,890 Sq Ft
  • Built 1995

  Last Sold Summary

  • 17% Below List Price
  • $206/SF
  • 58 Days On Market

  Current Estimated Value $434,810

  Last Listing Agent David Aurigemma Regency Real Estate, LLC

  33 Mallory Rd, Watertown, CT 06795
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  Not Listed For Sale

  245 Cherry Ave Unit O22, Watertown, CT 06795

  • 1 Bed
  • 1 Bath
  • 728 Sq Ft
  • Built 1968

  245 Cherry Ave Unit O22, Watertown, CT 06795

  Last Sold Summary

  • 33 Days On Market

  Last Listing Agent Shelley Drakeley Drakeley Real Estate, Inc.
• 

  /2

  $558,465

  New Construction Pending

  • 3 Beds
  • 2.5 Baths
  • 1,778 Sq Ft

  71 Turnberry Ct Unit 17, Watertown, CT 06795

  Easy Living Begins at Turnberry Estates - a thoughtfully designed 55+ adult community offering 32 single-story homes tailored for low-maintenance living. These to-be-built residences combine style and practicality with open-concept layouts, vaulted ceilings, and a range of customizable finishes to suit your personal taste. Each home features 3 bedrooms, 2 full bathrooms, and floor plans ranging

  Renee Lovley Century 21 AllPoints Realty

  71 Turnberry Ct Unit 17, Watertown, CT 06795
• 

  $287,000

  Sold Aug 29, 2025

  136 Bamford Ave, Oakville, CT 06779

  • 3 Beds
  • 1 Bath
  • 1,148 Sq Ft
  • Built 1944

  Last Sold Summary

  • 1% Below List Price
  • $250/SF
  • 34 Days On Market

  Current Estimated Value $306,816

  Last Listing Agent Beverly DiScala William Raveis Real Estate

  136 Bamford Ave, Oakville, CT 06779
• 

  Est $442,497

  Not Listed For Sale

  118 Pullen Ave, Oakville, CT 06779

  • 4 Beds
  • 3 Baths
  • 2,669 Sq Ft
  • Built 1949

  118 Pullen Ave, Oakville, CT 06779

  Last Sold Summary

  • 29 Days On Market

  Last Listing Agent Robert Perriello Century 21 AllPoints Realty
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  /11

  $269,900

  Under Contract

  • 2 Beds
  • 2 Baths
  • 1,188 Sq Ft

  44 Maplewood St, Waterbury, CT 06708

  AMAZING AFFORDABLE VALUE! This well maintained home located in the sought after BUNKER HILL area is a wonderful start or finish! The home offers Living Room, Kitchen with newer countertop & wood flooring, 2 updated Full Baths, 2 Bedrooms upstairs & One Bedroom in the lower level with a private entrance & interior access. Perfect space for an in-law or roommate, gameroom, Gym. Cathedral Ceilings &

  RITA BLUE Blue Real Estate

  44 Maplewood St, Waterbury, CT 06708
• 

  $285,000

  Sold Jul 10, 2026

  33 Chestnut Grove Rd, Watertown, CT 06795

  • 4 Beds
  • 2 Baths
  • 1,499 Sq Ft
  • Built 1916

  Last Sold Summary

  • 24% Below List Price
  • $190/SF
  • 56 Days On Market

  Current Estimated Value $313,371

  Last Listing Agent Joe Moreira Clearview Realty LLC

  33 Chestnut Grove Rd, Watertown, CT 06795
• 

  Est $331,870

  Not Listed For Sale

  62 Highwood Ave, Oakville, CT 06779

  • 2 Beds
  • 2 Baths
  • 1,480 Sq Ft
  • Built 1971

  62 Highwood Ave, Oakville, CT 06779

  Last Sold Summary

  • 12 Days On Market

  Last Listing Agent David Aurigemma Regency Real Estate, LLC
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  /34

  $345,000

  $24K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,056 Sq Ft

  462 Davis St, Oakville, CT 06779

  Welcome to a classic Colonial brimming with character, warmth, and opportunity. Situated on a generous corner lot in one of Oakville's established neighborhoods, this inviting three-bedroom home offers timeless appeal and comfortable everyday living. Step inside to discover sun-filled living spaces accented by hardwood floors, original door hardware, and classic New England charm. The bright

  Breanna Goebel Compass Connecticut, LLC

  462 Davis St, Oakville, CT 06779
• 

  $195,000

  Sold Aug 28, 2025

  148 Westbury Park Rd Unit D, Watertown, CT 06795

  • 2 Beds
  • 1.5 Baths
  • 1,098 Sq Ft
  • Built 1969

  Last Sold Summary

  • $178/SF
  • 141 Days On Market

  Last Listing Agent Ken Demirs Regency Real Estate, LLC

  148 Westbury Park Rd Unit D, Watertown, CT 06795
• 

  Est $399,853

  Not Listed For Sale

  169 Echo Lake Rd, Watertown, CT 06795

  • 5 Beds
  • 3 Baths
  • 1,872 Sq Ft
  • Built 1900

  169 Echo Lake Rd, Watertown, CT 06795

  Last Sold Summary

  • 17 Days On Market

  Last Listing Agent Raelyn Lawrence Coldwell Banker Realty
• 

  

  /30

  $320,000

  $20K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,504 Sq Ft

  319 Thomaston Rd Unit 13, Watertown, CT 06795

  Desirable Watertown Old Farms townhome offering open-concept living, custom stone, natural gas fireplace with built-in shelving, granite kitchen, and a private deck overlooking serene wooded surroundings. The bright living and dining area features warm wood-style flooring, a natural gas fireplace framed by custom stonework and flanked by built-in bookshelves, and a sliding door that leads to a

  Taylor O'Keefe Drakeley Real Estate, Inc.

  319 Thomaston Rd Unit 13, Watertown, CT 06795
• 

  $622,800

  Sold Jan 09, 2026

  239 Old Farms Rd, Watertown, CT 06795

  • 4 Beds
  • 2.5 Baths
  • 3,114 Sq Ft
  • Built 1986

  Last Sold Summary

  • 11% Below List Price
  • $200/SF
  • 77 Days On Market

  Current Estimated Value $664,556

  Last Listing Agent Ken Demirs Regency Real Estate, LLC

  239 Old Farms Rd, Watertown, CT 06795
• 

  Est $278,853

  Not Listed For Sale

  246 Falls Ave, Oakville, CT 06779

  • 3 Beds
  • 1 Bath
  • 1,008 Sq Ft
  • Built 1943

  246 Falls Ave, Oakville, CT 06779

  Last Sold Summary

  • 14 Days On Market

  Last Listing Agent Emmannuel Pina eXp Realty
• 

  

  /21

  $425,000

  • 4 Beds
  • 2 Baths
  • 1,558 Sq Ft

  77 Hubbell Ave, Oakville, CT 06779

  Charming & remodeled 4 Bedroom Colonial with beautiful brand new kitchen with Quartz Countertops, soft-close dovetail modern cabinetry, Center Island with Breakfast Bar and Stainless Steel Appliances. Hardwood floors throughout. Newly remodeled full baths on both the main and upper levels. This home provides ample parking & storage, Enclosed Sun Porch, Driveway plus a large detached 2 car Garage,

  Maria Vilar Lamacchia Realty

  77 Hubbell Ave, Oakville, CT 06779
• 

  $506,562

  Sold Feb 25, 2026

  48 Wentworth Ct Unit 9, Watertown, CT 06795

  • 3 Beds
  • 2 Baths
  • 1,444 Sq Ft
  • Built 2025

  Last Sold Summary

  • $351/SF
  • 0 Days On Market

  Last Listing Agent Renee Lovley Century 21 AllPoints Realty

  48 Wentworth Ct Unit 9, Watertown, CT 06795
• 

  Est $440,602

  Not Listed For Sale

  174 Jordan Ave, Oakville, CT 06779

  • 6 Beds
  • 2 Baths
  • 2,654 Sq Ft
  • Built 1930

  174 Jordan Ave, Oakville, CT 06779

  Last Sold Summary

  • 20 Days On Market

  Last Listing Agent Aurel Adhami Showcase Realty, Inc.
• 

  

  /40

  $800,000

  Pending

  • 4 Beds
  • 4.5 Baths
  • 4,321 Sq Ft

  95 Carola Dr, Watertown, CT 06795

  Welcome to this impeccably maintained, sprawling Colonial situated in the heart of Watertown. Boasting 4,321 square feet of living space, this home offers a perfect blend of timeless design and modern comfort. The main level features a spacious chef's kitchen complete with an island, breakfast nook and a butler's kitchen for seamless food preparation. The great room boasts a cozy fireplace and

  Roland Leal William Pitt Sotheby's Int'l

  95 Carola Dr, Watertown, CT 06795
• 

  $630,000

  Sold Sep 03, 2025

  1414 Guernseytown Rd, Watertown, CT 06795

  • 4 Beds
  • 2 Baths
  • 2,380 Sq Ft
  • Built 2011

  Last Sold Summary

  • 2% Above List Price
  • $265/SF
  • 3 Days On Market

  Current Estimated Value $662,535

  Last Listing Agent David Aurigemma Regency Real Estate, LLC

  1414 Guernseytown Rd, Watertown, CT 06795
• 

  Est $483,051

  Not Listed For Sale

  40 Warren Way, Watertown, CT 06795

  • 3 Beds
  • 3.5 Baths
  • 4,150 Sq Ft
  • Built 1919

  40 Warren Way, Watertown, CT 06795

  Last Sold Summary

  • 59 Days On Market

  Last Listing Agent Ryan Bollard William Pitt Sotheby's Int'l
• 

  

  /40

  $550,000

  • 3 Beds
  • 3 Baths
  • 2,520 Sq Ft

  300 Hilltop Rd, Oakville, CT 06779

  Welcome to 300 Hilltop Road in Oakville - an expansive ranch-style home offering comfort, space, and easy one-level living. This 3-bedroom, 3-bath home features an inviting open floor plan, creating a seamless flow between the main living areas and making it ideal for both everyday living and entertaining. A beautiful dual-sided fireplace between the living rooms adds warmth, character, and a

  Desiree Meister William Pitt Sotheby's International Realty

  300 Hilltop Rd, Oakville, CT 06779
• 

  $615,000

  Sold Apr 10, 2026

  191 Pond View Dr, Watertown, CT 06795

  • 3 Beds
  • 2.5 Baths
  • 2,312 Sq Ft
  • Built 1998

  Last Sold Summary

  • 3% Above List Price
  • $266/SF
  • 40 Days On Market

  Current Estimated Value $618,079

  Last Listing Agent Jonna Dibble BHGRE Gaetano Marra Homes

  191 Pond View Dr, Watertown, CT 06795
• 

  Est $335,371

  Not Listed For Sale

  24 Crestwood Ave, Watertown, CT 06795

  • 3 Beds
  • 2 Baths
  • 1,664 Sq Ft
  • Built 1958

  24 Crestwood Ave, Watertown, CT 06795

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Jason Saphire www.HomeZu.com
• 

  

  /34

  $369,900

  Pending

  • 3 Beds
  • 1.5 Baths
  • 1,514 Sq Ft

  32 Moreland Ave, Oakville, CT 06779

  Charming, well-maintained split-level home featuring three levels of functional living space. The main level offers a bright living room with hardwood floors and an oversized, eat-in kitchen perfect for entertaining. Upstairs, find three comfortable bedrooms with carpet protecting the original hardwood floors, alongside a classic full tile bath. The cozy lower-level family room includes a

  Sherry Cosmos Proe Regency Real Estate, LLC

  32 Moreland Ave, Oakville, CT 06779

Showing Results 161 - 200, Page 5 of 18