Browse All Watertown CT Properties with Pool for Sale

6 Beds ⋅ 7 Baths ⋅ 24192575 MLS

Welcome to 47 Academy Hill, a stately Victorian-era Colonial where timeless craftsmanship meets modern comfort in the heart of Watertown. Offering more than 3,700 square feet of beautifully maintained living space, this exceptional home is just a five-minute walk from The Taft School and minutes from downtown shops, restaurants, and amenities. A gracious wraparound porch creates an impressive first impression and sets the tone for the remarkable period details found throughout. Inside, soaring 10-foot ceilings, extensive moldings, custom built-ins, and generously proportioned rooms reflect a level of craftsmanship that would be extraordinarily difficult to reproduce in today's building climate. The versatile layout includes several en suite bedrooms and baths, providing excellent flexibility for family, guests, or multigenerational living. A bright sun porch overlooks the private backyard and in-ground pool, creating a beautiful space to relax and enjoy the changing seasons. The pool area offers a peaceful setting for summer entertaining and everyday enjoyment. Rich in character and filled with irreplaceable architectural details, this distinctive home presents a rare opportunity to own one of Watertown's truly special properties.

47 Academy Hl, Watertown

$205,000

2 Beds ⋅ 2 Baths ⋅ 24187354 MLS ⋅ Highgate BLDG.

Welcome home to this spacious, two-bed, two bath, upper level end unit in a quiet, peaceful complex! Enjoy well-maintained grounds, open fields, scenic views, and a swimming pool that is perfect for summer. Find a beautiful built-in entertainment center/bookshelf/display case built and installed by the current owner. A roomy kitchen overlooks an open lawn. Two large bedrooms both have ample closet space and large windows to let in a lot of natural light! A small hall between bedrooms has a full bathroom, while the main bedroom has its own full bathroom. Find extra storage space in a walk-up attic. Relax in a large living/dining area. The Highgate complex is located in a pretty, small-town, picturesque neighborhood. Come make this home your own! Minutes from highways for commuters, shopping, schools, restaurants, recreation, local lakes, and more.

245 Cherry Ave Unit A24, Watertown

$230,000

2 Beds ⋅ 2 Baths ⋅ 24186305 MLS ⋅ Highgate BLDG.

Welcome home to this well-maintained 2-bedroom, 2-bath condo offering over 1,000 square feet of comfortable living space. Inside, you'll find a clean, inviting interior with spacious rooms and well-kept carpeting throughout. Step outside onto the low-maintenance Trex deck, the perfect spot to enjoy your morning coffee while overlooking the peaceful backyard. Tucked away in a quiet setting, this condo offers the perfect blend of comfort, convenience, and easy, low-maintenance living with plenty of space to make your own.

245 Cherry Ave Unit E24, Watertown

$219,900

2 Beds ⋅ 2 Baths ⋅ 24178154 MLS ⋅ Highgate BLDG.

You don't want to miss this rare chance to own an updated first-floor, ranch-style, end-unit condo in the highly desirable Highgate community! Perfectly situated at the top of the hill close to the pool, this two bedroom unit offers peaceful, scenic surroundings and an amazing backyard view. Step inside to find an attractive remodeled kitchen featuring stylish cabinets, granite countertops, tile backsplash, stainless steel appliances, and a pantry closet. The spacious open-concept living and dining area is warm and inviting with hardwood floors, a ductless air conditioning unit, and sliders leading to a covered deck where you can relax and enjoy the tranquil setting. Both oversized bedrooms offer hardwood flooring, two large closets each, and plenty of natural light. The bathrooms were also remodeled in 2017. The full bath features a beautiful oversized shower, while the half bath includes a convenient stackable washer and dryer, eliminating the need for shared laundry facilities. Additional storage space is available in the basement, with dedicated storage areas for each unit. Highgate residents also enjoy access to the impeccably maintained in-ground pool area, complete with lounge chairs, dining tables, and grills, creating the perfect setting for summer relaxation and entertaining. The HOA includes heat, hot water, snow removal, and trash pickup, making for easy, low-maintenance living. The unit also comes with two assigned parking spots plus ample visitor parking.

Watertown

$779,900

4 Beds ⋅ 4 Baths ⋅ 24178706 MLS

Motivated Seller Price Improved 15K Welcome to 55 Butternut Ln, Watertown! Tucked away on 3.5 private acres, this custom-built 2006 home offers over 3,200 sq. ft. of living space thoughtfully designed for both comfort and entertaining. The open floor plan showcases soaring two-story ceilings, a spacious dining room/living room with wet bar, ice machine, and wine chiller, a welcoming family room with gas fireplace, and an eat-in kitchen that makes gathering easy. Additional highlights include central air, a built-in desk/office area, half bath, and an oversized two-car garage. Step outside and enjoy your own private retreat with a heated in-ground pool, hot tub, fire pit, bocce court, and horseshoe area perfect for hosting family and friends. Upstairs, you'll find four generously sized bedrooms, all with gleaming hardwood floors. The primary suite offers a walk-in closet, spa-like full bath, and private balcony overlooking the serene grounds. With a seamless blend of privacy, elegance, and entertainment-ready spaces, this rare property is truly one of a kind.

55 Butternut Ln, Watertown

$395,000

3 Beds ⋅ 2 Baths ⋅ 24179120 MLS

A charming colonial set right outside of Watertown's Taft area and historical section bringing modern and cozy style to a home that still holds some of its 1930's charm. Beautiful built ins throughout the homes' living room, dining room and even kitchen give it additional character while providing added kitchen storage, space for your drinkware or classy dinner sets and shelving to hold books full of stories you can't put down. The large dining room with its' vaulted ceiling and beaming natural light make this room the perfect space for dining at home or entertaining guests! In the kitchen you'll find gorgeous newer quartz countertops, stainless steel appliances and a view of the backyard oasis. Through the kitchen there is an additional pantry - and its huge! A half bath and laundry area are also on the main floor through the kitchen. Upstairs are three bedrooms and a full bathroom. Each bedroom has its own closet and there is an additional closet in the hallway for storage as well. A fully fenced in getaway is your new backyard with paver patio, firepit lounge area and two tier deck leading up to the large above ground pool- just in time for summer! There is still plenty of yard space and even a small set of garden beds. The detached two car garage also has heat through a wood stove for any time spent working in there during the winter. New upgrades include deck around pool 2020, fence in 2022, oil tank 2022, hot water heater 2019, dishwasher 2026, quartz counters.

72 Prospect St, Watertown

$498,000

4 Beds ⋅ 4 Baths ⋅ 24177877 MLS

You'll be the one everyone wants to visit this summer as you relax by your private inground pool! Set on over 2 picturesque acres in one of Watertown's most desirable locations, this charming 1840 Colonial offers the perfect blend of historic character, modern comfort, and resort-style outdoor living. This spacious 4-bedroom, 3.5-bath home features over 2,000 square feet of living space with eight well-proportioned rooms designed for everyday living and entertaining. Inside, you'll find three fireplaces, original wide-board wood floors, a large loft-style bedroom, an attached barn/shed with unlimited potential, clapboard siding, and inviting gathering spaces filled with timeless New England charm. Step outside and discover what truly sets this property apart. The sparkling inground pool is the centerpiece of your own private backyard retreat, complemented by an expansive patio, a charming gazebo, and multiple outdoor living spaces perfect for summer barbecues, pool parties, or simply unwinding in complete privacy. The expansive grounds provide exceptional space, tranquility, and room to enjoy the outdoors all season long. Conveniently located while offering a peaceful residential setting, this special property also features remote-controlled radiant heated floors in the dining room/enclosed porch for year-round comfort. From sunny afternoons by the pool to cozy evenings by the fire, this home offers the best of every season. You will fall in love with this beauty!

635 Northfield Rd, Watertown

$779,900

5 Beds ⋅ 4 Baths ⋅ 24165679 MLS

Welcome to your private retreat set on 2.7 beautifully maintained acres, offering the perfect blend of space, comfort, and lifestyle. This expansive 5-bedroom, 3.5-bath home spans approximately 3,400 square feet and features a bright, open layout designed for both everyday living and entertaining. Vaulted ceilings with exposed wood beams create a warm, architectural statement, while updated flooring and neutral tones provide a modern, move-in-ready feel. The spacious living areas flow seamlessly, offering flexibility for gatherings, relaxation, and work-from-home needs. Large windows throughout the home bring in abundant natural light and highlight the peaceful surroundings. Step outside to enjoy your own private outdoor oasis: In-ground pool perfect for summer enjoyment Tennis court offering recreation or multi-use potential Expansive yard with endless possibilities Recent updates include a newer roof, siding, garage doors, and patio-adding both value and peace of mind. This property offers a rare combination of privacy, space, and, lifestyle amenities, all within close proximity to shopping, dining, and major routes.

1460 Guernseytown Rd, Watertown

Start Your Search

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

Watertown Homes with Pool

Our website features the best real estate search for properties available in Watertown and surrounding areas with pool. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes.

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire.

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood!

Considering selling or refinancing your home? Get an INSTANT property valuation now!