Pleasant Valley Real Estate

Welcome to Pleasant Valley, Connecticut – a charming neighborhood that truly embodies the essence of suburban living. Nestled in the heart of Litchfield County, Pleasant Valley offers residents a serene escape from the hustle and bustle of city life while still providing convenient access to urban amenities.

The neighborhood is known for its picturesque landscapes, characterized by rolling hills, lush greenery, and scenic views that change beautifully with the seasons. Whether you’re enjoying a leisurely stroll along tree-lined streets or exploring the nearby parks, the natural beauty of Pleasant Valley is sure to captivate you.

Families will appreciate the excellent school system, which is committed to providing quality education and fostering a supportive community for children of all ages. The local parks and recreational facilities offer ample opportunities for outdoor activities, including hiking, biking, and picnicking, making it a perfect spot for families to bond and create lasting memories.

Pleasant Valley is also home to a tight-knit community that prides itself on its friendly atmosphere. Local events and gatherings foster connections among neighbors, creating a warm and welcoming environment. From farmers' markets to seasonal festivals, there’s always something happening that brings residents together.

Additionally, the neighborhood’s proximity to major highways makes commuting to nearby cities like Hartford and Waterbury a breeze, allowing residents to enjoy the tranquility of suburban life without sacrificing convenience.

Discover the charm of Pleasant Valley – where community spirit meets natural beauty, making it an ideal place to call home. Whether you’re a first-time homebuyer or looking to settle down, Pleasant Valley invites you to explore its unique offerings and vibrant lifestyle.

Newest Listings in Pleasant Valley

$139,900

1 Beds ⋅ 1 Baths ⋅ 24193625 MLS ⋅ Pleasant Valley BLDG.

Stop renting and start investing in your future! This affordable first-floor end-unit, 1-bedroom, 1-bath condo offers a fantastic opportunity to build equity while enjoying the benefits of homeownership. The spacious step-down living room features 9-foot ceilings and oversized windows, creating an inviting space filled with natural light. Ideally located just minutes from shopping, dining, and major highways, you'll have everything you need within easy reach. The unit is ready for your personal updates, giving you the chance to add your own style and make it truly feel like home. Enjoy the convenience of both interior and exterior entrances, making everyday living even easier. As an added bonus, the community features an outdoor pool-perfect for cooling off and relaxing during the warmer months. If you've been searching for an affordable place to call your own, this is an opportunity you won't want to miss. Schedule your showing today and discover all the potential this charming condo has to offer! ***You must owner occupy for 2 years before you are able to rent the unit***

949 Pleasant Valley Rd Unit 3-3, South Windsor

$629,900

4 Beds ⋅ 3 Baths ⋅ 24194368 MLS

Welcome to this beautiful Contemporary home offering 3465 square feet of updated living space, perfectly situated on a level 1.2 acre lot complete with a picturesque pond and a fully fenced in backyard. Designed for both comfortable everyday living and effortless entertaining, this spacious home features 9 rooms, 4 bedrooms and 3 full bathrooms. The updated kitchen is a true showpiece, featuring a large center island with elegant quartz countertops, a built-in wine refrigerator, soft-close cabinetry and drawers and abundant workspace for cooking and gathering. The inviting primary suite serves as a private retreat on the top floor with an expansive spa-like full bath, walk-in closet and loft. Recent improvements include a new roof and a new chimney flue, while the updated bathrooms add modern style and convenience throughout the home. Outside, you'll appreciate the huge concrete deck overlooking the flat fenced in backyard offering endless possibilities for recreation, gardening or simply enjoying the tranquil setting. Beyond the fence is the scenic pond. Car enthusiasts and hobbyists will love the 4-car tandem garage, providing exceptional storage and workspace. This unique home has so much to see.

1010 Strong Rd, South Windsor

$359,900

4 Baths ⋅ 24193960 MLS

Back on the market and reduced. Versatile Renovated Church Property - Ideal for Classrooms, Events, or Multi-Use. This spacious former church property includes a 30' x 40' (1,200 sq. ft) meeting hall, complete with a dedicated audio room-perfect for gatherings, presentations, or worship services. Recently updated from top to bottom, renovations include brand-new walls, ceilings, flooring, and a new overhead door-providing a fresh, move-in-ready environment. The building includes 14 additional rooms and 4 bathrooms, offering an excellent layout for classrooms, offices, or community use. With three separate front entrances and dual gas meters, the property also presents strong potential for subdivision into multiple functional spaces. This is a unique, flexible space with endless possibilities. A must-see opportunity-you won't be disappointed!

400 Chapel Rd Unit 2A, South Windsor

$199,900

1 Beds ⋅ 1 Baths ⋅ 24192960 MLS ⋅ Cinnamon Springs BLDG.

Move right into this beautifully maintained condo offering the perfect combination of comfort, convenience, and lifestyle. This move-in ready home features a rare and versatile double loft, providing endless possibilities for a home office, guest space, fitness area, or additional living space. Enjoy the convenience of in-unit laundry and unwind on your private patio overlooking a peaceful water view-the perfect backdrop for your morning coffee or evening relaxation. With low condo HOA, this pet-friendly community offers exceptional value along with fantastic amenities, including a sparkling pool and clubhouse for residents to enjoy. Ideally located close to shopping, dining, and major highways, this home delivers low-maintenance living in a desirable setting. If your looking for a turnkey home with unique character, this condo is a rare opportunity you won't want to miss!

30 Cinnamon Springs S Unit 30, South Windsor

$374,900

2 Beds ⋅ 2 Baths ⋅ 24192909 MLS ⋅ Brookside BLDG.

Tucked into a well-kept condo community in one of South Windsor's most convenient spots, 13 Ivy Lane offers low-maintenance living without giving up the space or the finishes. A dramatic two-story fireplace greets you at entry, with hardwood floors running throughout and natural light pouring through skylights and oversized windows. The kitchen is done right - granite countertops and a full appliance suite, all just two years old. Custom remote-controlled Hunter Douglas shades add everyday ease, and energy-efficient Weathershield windows, including the slider to the deck, keep things comfortable year-round. Velux skylights, all less than ten years old, bring even more light in. A first-floor bedroom and full bathroom - with a newly updated shower - make single-level living a real option, ideal for guests, a main-floor primary, or anyone wanting to skip the stairs. Upstairs, a second bedroom is joined by a versatile room that flexes to fit your life: a third bedroom, home office, study, or quiet sitting room. Downstairs, the 300+ sq ft finished basement is built for gathering, with a built-in wet bar and a pool table that stays with the home. Additional highlights: one-car garage, ample parking, and a three-year-old hot water heater. Everything South Windsor has to offer is just minutes away - come see this easy, move-in-ready condo!

13 Ivy Ln Unit 13, South Windsor

$375,000

3 Beds ⋅ 2 Baths ⋅ 24191548 MLS

Welcome to 384 Long Hill Road, South Windsor! This charming two-story home offers 1,440 square feet of comfortable living space on nearly a half-acre lot. Originally built in 1800 and renovated in 1972, it combines timeless character with modern-day comfort. The flexible floor plan features 3 bedrooms and 2 full bathrooms, including a first-floor bedroom and full bath-ideal for guests, multigenerational living, or anyone looking for first-floor convenience. Upstairs you'll find two additional bedrooms and a second full bath. Just off the kitchen, the spacious den/mudroom provides the perfect space for a home office, playroom, or cozy family room. Enjoy the comfort of central air, natural gas heat, public sewer, and a private well. The attached two-car garage, generous driveway, and spacious backyard offer plenty of room for parking, entertaining, gardening, or simply relaxing outdoors. Conveniently located near I-84, Route 291, shopping, restaurants, parks, and South Windsor's highly rated schools, this home is ready to welcome its next owner. Why paying rent if you can enjoy the freedom at this property? It is Natural gas heat, Roof 2012, Central Air 2022. Seller is selling the property as is .

384 Long Hill Rd, South Windsor

$459,000

3 Beds ⋅ 3 Baths ⋅ 24190674 MLS

Stunning and fully updated 3-bedroom and 2.5 baths home in one of South Windsor's most sought-after neighborhoods, surrounded by natural beauty. This move-in-ready property features new windows, new flooring, and newer carpeting throughout. The wraparound porch provides a perfect setting to relax and enjoy the peaceful surroundings. The inviting living room with a fireplace flows seamlessly into the dining area and updated kitchen, creating an ideal layout for everyday living and entertaining. The remodeled kitchen boasts new cabinetry, quartz countertops, and newer appliances, offering both style and functionality. The spacious primary suite features a ceiling fan, walk-in closet, and private full bath. The second bedroom also includes a ceiling fan and walk-in closet, while the third bedroom is perfect for guests, a home office. Access to the porch from the dining area provides an additional space to unwind. The beautifully landscaped backyard is ideal for gatherings, entertaining, and outdoor enjoyment. Combining modern updates, generous living spaces, and a serene setting, this exceptional home has everything today's buyers are looking for. The smart lights are installed in all of the bedrooms, and most of the smart appliances are also set up. Additionally, the fans are located in the living area and the master bedroom. Schedule your private showing today!

16 Arrowwood Cir Unit 16, South Windsor

$695,000

3 Beds ⋅ 3 Baths ⋅ 24187032 MLS

Enjoy the country and ultimate privacy in this unique 7-room Raised Ranch home with many upgrades. Situated on a 10+ acre lot the property is minutes from shopping & conveniences at Town Center, Costco, Whole Foods, Evergreen & the Buckland corridor. This 3-bedroom - 3 full bath home offers a large recently upgraded eat-in kitchen with an abundance of cabinets, full appliances, hardwood flooring, ceiling fan, large breakfast bar and lots of sun and brightness from two large bay windows facing southeast. There is an adjacent open space dining area and living room with sliders to a large 450+ sq. ft. deck which is also southeast facing affording sunny picturesque views of the park like grounds. All three bedrooms are on the main level including the primary with recently upgraded ensuite bath with large ceramic tile shower, bench seat, glass door, custom sink, and ceramic tile flooring. There is a second main level bathroom also recently renovated with high-end finishes including ceramic tile flooring convenient to bedrooms 2 & 3. The lower level has a finished family room with brick fireplace and walk-out door. The lower level also offers a 3rd full bath with shower and washer/dryer. The finished lower level is completed with two separate rooms currently utilized for hobbies & exercise, but which could be easily re-purposed to fit the needs of a new family. The entire finished area of the lower level has laminate tile flooring with access to the large 2-car garage.

610 Clark St, South Windsor

$589,900

4 Beds ⋅ 3 Baths ⋅ 24177678 MLS

Welcome to this beautifully maintained 4-bedroom, 2.5-bath home offering the perfect blend of comfort, character, and outdoor living. Proudly owned and lovingly cared for by the original owners, this home stands out from others in the neighborhood thanks to several thoughtful custom upgrades and unique design touches throughout. Inside, you'll find spacious living areas, a functional layout, and a warm, inviting atmosphere that reflects years of meticulous maintenance and pride of ownership. Every detail has been carefully cared for, making this home truly move-in ready. Step outside and discover your own private backyard oasis - a peaceful retreat designed for both relaxation and entertaining. Whether you're enjoying quiet mornings, hosting summer gatherings, or unwinding after a long day, the beautifully landscaped outdoor space offers the perfect escape right at home. This is a rare opportunity to own a home with individuality, quality craftsmanship, and timeless appeal in a desirable neighborhood.

480 Quarry Brook Dr, South Windsor

$850,000

24162866 MLS

Welcome to your own nature lover's paradise in the Berkshire foothills! This exceptional 140-acre property offers breathtaking views of Ski Sundown and the potential for multiple home sites with views. A rare opportunity to build your dream retreat or even create a family compound. Abutting the American Legion State Forest and the Farmington River, the existing trails offer endless opportunities to explore, two meandering streams cross through the property adding a soothing soundtrack. Situated on a quiet cul-de-sac, you'll experience a sense of privacy and seclusion that complements the natural surroundings but convenience is not compromised, shopping and highway access are just a stone's throw away. The proximity to Lake McDonough provides endless opportunities for water sports from boating and fishing to swimming and kayaking. Ski Sundown is also close by where winter enthusiasts can indulge in downhill skiing and snowboarding. Don't miss your chance to own a slice of paradise!

13 Dew Rd, Barkhamsted

$99,000

24088276 MLS

Nestled on a serene country lane in the Pleasant Valley section of Barkhamsted, this prime 2.07-acre lot at 28 Fuller Road offers an idyllic setting for your dream home. Boasting 293 feet of frontage on Fuller Road, this property provides ample space and privacy. Enjoy stunning views of the valley, with close proximity to the Farmington River and the reservoir, making it perfect for nature enthusiasts and those seeking a tranquil lifestyle. Adding to its charm, a small meandering brook flows from the rear to the front of the property. The site is ready for construction with a carved-out driveway and completed septic feasibility. Embrace the opportunity to build your custom home in this beautiful, peaceful location.

28 Fuller Rd, Barkhamsted

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.