Middlesex County Homes with Cottage Style

Middlesex County Homes with Cottage Style

Welcome to Middlesex County, Connecticut, a charming locale that perfectly blends natural beauty with vibrant community living. Nestled along the scenic Connecticut River, this county is a haven for those who appreciate both outdoor adventures and the quaint charm of small-town life. With its picturesque landscapes, rich history, and a variety of recreational opportunities, Middlesex County is an ideal place to call home.

One of the standout features of homes in this area is their enchanting cottage-style architecture. These delightful residences often exude warmth and character, making them perfect for those seeking a cozy retreat. With their inviting porches, gabled roofs, and whimsical gardens, cottage-style homes in Middlesex County provide an idyllic setting for both relaxation and entertaining. Imagine sipping your morning coffee on a sun-drenched porch or hosting friends in a beautifully landscaped backyard—these homes offer a lifestyle that is both charming and functional.

In addition to their aesthetic appeal, many of these cottages are conveniently located near the county’s vibrant downtown areas, where you can explore local shops, enjoy farm-to-table dining, or take part in community events. The surrounding natural beauty, from the rolling hills to the serene riverbanks, provides endless opportunities for outdoor enthusiasts. Whether you’re hiking the trails, kayaking on the river, or simply enjoying a peaceful stroll through one of the many parks, Middlesex County is a place where nature and community thrive.

Discover the magic of cottage-style living in Middlesex County, where charm meets convenience in a truly picturesque setting. Your dream home awaits!

Newest Middlesex County Homes with Cottage Style

7 Toms Rd, Old Saybrook
$1,200,000
2 Beds ⋅ 1 Baths ⋅ COMING SOON Status ⋅ 24216468 MLS
2 Plots sold together- 7 & 18 Toms Rd. Rare opportunity to own a slice of CT shoreline! Tucked away at the end of a private road, this charming seasonal waterfront cottage offers water on 2 sides, water views on 3, private beach, backyard dock & breathtaking sunsets. Cherished by the same family for generations, this special coastal retreat captures everything there is to love about beach living. Recently refreshed with new flooring, new granite counters, new hot water heater and electrical updates. The cottage features an inviting open floor plan, flexible sleeping accommodations with convenient convertible beds & a spectacular enclosed front porch where you can relax, entertain & take in the waterfront scenery. Spend your days swimming, kayaking, paddleboarding, or simply enjoying the sand & sea breeze. An outdoor shower makes rinsing off after a day at the beach a breeze. The property includes both front & back lots, offering a unique waterfront setting with room to enjoy the outdoors. Conveniently located near Harvey's Beach & all that Old Saybrook has to offer, this property presents an incredible opportunity for a personal summer getaway, a family retreat, or a seasonal rental investment. Currently winterized & ready for its next chapter, this is your chance to create lasting shoreline memories in a truly special location. Come experience the sunsets, salty air, and laid-back beach lifestyle.

7 Toms Rd, Old Saybrook
61 Bailey Rd, East Haddam
$215,000
1 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24215061 MLS
Welcome to Bashan Lake, widely regarded as one of Connecticut's cleanest lakes, and your own cottage getaway. This seasonal cottage is a rare chance to enjoy lake life without the lakefront price tag. Swim, kayak, fish, and relax on the beach, all with a deeded right to use the lakefront lot directly across the street. Inside, you'll find an open kitchen and living area, a primary bedroom with room for a king bed, and a den or second bedroom currently set up with two twin beds, Step outside to a covered porch and large deck with lake views, ideal for entertaining and cooking out. Parking in front fits four cars. Peace of mind comes with a new engineered septic system installed in 2019, a rare find in this area, and all rooms were freshly painted. All indoor furniture shown in the photos is included, along with the refrigerator, so you can just bring your bags and start enjoying the summer.

61 Bailey Rd, East Haddam
18-A Lake Shore Dr, Middlefield
$595,000
2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24210670 MLS
Fall on Lake Beseck may just be its best-kept secret. Wake up to spectacular sunrises reflecting off the water, take in the changing colors from your private deck, and enjoy peaceful days kayaking, fishing or simply relaxing lakeside. This charming direct waterfront cottage offers the lake lifestyle buyers dream about, with private docks and a floating dock providing instant access to the water. Motorboats are welcome, so when warmer days return, boating and swimming are right outside your door. Inside, the open floor plan is filled with natural light and flows into a beautiful sunroom wrapped in windows, keeping the lake views front and center in every season. Step outside to the Trex deck, the perfect spot for morning coffee, evening cocktails and a front-row seat to some unforgettable sunrises. Thoughtfully maintained with central air and a new roof in 2024, this home is ready to enjoy from day one. Lake Beseck is managed by DEEP, and no flood insurance is required. Looking to create something more? There is potential to build up to 35 feet, subject to approvals. Just minutes from I-91 and close to Powder Ridge, Lyman Orchards and four golf courses, this is more than a summer escape. It's a place to enjoy every season and start making lake memories now.

18-A Lake Shore Dr, Middlefield
18 Brook Trl, East Hampton
$347,000
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24209823 MLS
Lake lovers rejoice! With views of the lake, beach-access, possible dock access, this home is just waiting for your refurbishing touch. Drenched in the charm of yesteryear with 3 Bedrooms, 1 bath, and a wide-open floor plan - this home is perfect for anyone looking for a summer cabin getaway or anyone looking to get Hands-On your new water-side retreat. Morning coffee on the lakeview deck, chilly evenings by the fieldstone fireplace, and entertaining friends in the cozy. This East Hampton home is revamp ready, the only thing missing is your vision! Selling AS IS. This property extends across the road far enough to include a second lot with building potential. House with lot (Map ID 10A 79 3), Lot (Map ID 10A 78 29. Total taxes for both $7,777.22.

18 Brook Trl, East Hampton
89 Book Hill Rd, Essex
$479,999
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24209577 MLS
Welcome to 89 Book Hill Road in the heart of Essex Village. This beautifully updated Cape offers a perfect blend of classic New England charm and modern comfort. Set on a private lot surrounded by mature trees, the home features a spacious and light-filled layout with hardwood floors, two fireplaces, and a flexible floor plan. The kitchen has been tastefully updated with modern finishes, flowing into a cozy dining area ideal for gatherings. Upstairs you'll find comfortable bedrooms with ample storage, while the finished lower level adds versatile space for a family room, home office, or gym. Enjoy the convenience of central air, a walk-out basement, and an attached two-car garage. The property also offers a large yard perfect for outdoor entertaining, gardening, or simply relaxing. Located just minutes from the shops, restaurants, and waterfront of Essex Village, this home provides easy access to Route 9, local marinas, and top-rated schools including Essex Elementary and Valley Regional High School. Whether you're seeking a full-time residence or a weekend retreat, 89 Book Hill Road is ready to welcome its next owner. One of the parties to the LLC has an active real estate license

89 Book Hill Rd, Essex
105 Shore Rd, Clinton
$899,000
4 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24206662 MLS
Quintessential summer waterfront cottage lovingly owned by the same family for 88 years. Enjoy four bedrooms and sleeping porch option. Large Sandy beachfront. Long Island Sound views from dining room, living room, enclosed 400sf porch and upstairs bedroom. Paneling in bedrooms and hardwood floors on lower level. Also nearby access to Clinton Town Beach and Hammonasset State Park. Outlet mall and grocery stores nearby. Close public bus, commuter and Amtrak train station. Shown by appointment. Do not go on the property without permission.

105 Shore Rd, Clinton
144 Shore Rd, Clinton
$899,000
4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24206668 MLS
Experience the very best of Connecticut shoreline living! The stunning REMODELED interior has 4 BR 2-baths with beautiful water & marsh views and deeded beach access. This exceptional property offers the perfect blend of relaxed coastal living with incredible flexibility and right-of-way access to the beach. Every square inch of the interior has been thoughtfully renovated with today's lifestyle in mind. The bright, open floor plan creates an inviting flow for everyday living & effortless entertaining. The main level features a spacious family room, sitting area, dedicated work-from-home space, a fabulous new kitchen with loads of storage & breakfast bar. Laundry/mud room. A beautiful bedroom with a full bath & walk in closet ideal for guests or one-level living.Upstairs, the spacious primary suite offers a walk-in closet with French doors opening to a private heated sunroom & large deck where you can unwind while taking in the water views & coastal breeze. 2 additional bedrooms & a beautifully remodeled full bath.Outdoor living is equally impressive with a deck, outdoor shower, peaceful marsh views & steps to the sandy beach creating a picturesque natural backdrop. Charming red barn offers additional storage for your kayak, bikes, outdoor toys & more. Located near Duck Island, Clinton Harbor, marinas, shopping ,great restaurants & Long Island Sound, this beautifully re-imagined home is perfect as a year-round residence, weekend escape!

144 Shore Rd, Clinton
74 Pine Rd, East Haddam
$299,000
3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24205225 MLS
Your Connecticut lake escape awaits! Welcome to 74 Pine Rd, a beautifully renovated 3-bedroom retreat in the desirable Moodus Lake Shores community on the Upper Moodus Reservoir. This move-in-ready home features a renovated kitchen and bathroom, new flooring, stainless-steel appliances, fresh paint, and ductless heating and air conditioning. The spacious primary bedroom offers a walk-in closet, while the bright, inviting interior is designed for easy lake living. Step outside to the large deck, perfect for morning coffee, outdoor dining, entertaining, or unwinding with peaceful water views. Beach rights and association boat-launch access make it easy to enjoy swimming, kayaking, boating, fishing, and days by the water. Enjoy seasonal occupancy from April 15 through October 31-the heart of Connecticut's lake season from spring weekends through summer and fall foliage. An ideal weekend getaway, summer home, or spring-through-fall retreat from NYC, Westchester, Fairfield County, Boston, or beyond. A turnkey Connecticut lake retreat under $300K-just bring your bags and start enjoying!

74 Pine Rd, East Haddam
120-A Shore Rd, Clinton
$499,900
2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24204504 MLS
MOVE-IN READY AND UPDATED HOME AT CLINTON BEACH. Come enjoy the cutest cottage on Shore Rd. EXTENSIVELY RENOVATED. Just steps to the beach and minutes away from town and all of the CT shoreline attractions. DIRECT BEACH ACCESS ACROSS THE STREET. This newly renovated cottage has all the modern amenities of today and all the old charm of yesterday. HEATED FOR YEAR ROUND COMFORT. The cottage features water views, a fully equipped kitchen, washer/dryer, and dishwasher. The cottage sleeps up to 6 (1 queen,1 bunkbed, and 1 sleeper sofa) and has parking for 2 cars. Private beach club located down the road. Upper level loft offers space (not included in sq ft). Easy access to I-95 and town amenities.

120-A Shore Rd, Clinton
127 Shore Rd, Clinton
$2,400,000
8 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24195448 MLS
Three direct beachfront cottages located right on the sand of the Long Island Sound in Clinton, Connecticut offer a rare turnkey coastal investment opportunity. The property includes two well-appointed 2-bedroom cottages and one spacious 4-bedroom cottage, all fully furnished and recently updated for modern comfort. Each cottage provides unobstructed waterfront views, immediate beach access, and the charm of classic shoreline living. With a strong and proven rental history, this unique package is ideal for investors or buyers seeking a move-in ready, income-producing beachfront retreat along the Connecticut shoreline.

127 Shore Rd, Clinton
2 Hay Field Rd, East Haddam
$189,000
2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24191133 MLS
This charming and cozy Lake Hayward cottage is ready for your personal touch, making it the perfect summer vacation spot or weekend retreat. Major updates have already been completed, including a newer roof, siding, windows, and an updated electrical panel. Relax on the sun-filled porch, catch a cool breeze on the deck, and enjoy being just a short walk from four private association beaches. The active Lake Hayward community features access to tennis, pickleball, and a full lineup of fun summer events at the pavilion, offering endless entertainment for the entire family. This cottage has so much potential ~ come make it your own today!

2 Hay Field Rd, East Haddam
52 Pond Meadow Rd, Essex
$430,000
2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24189285 MLS
Welcome home to your own private cottage style farm house in the heart of picturesque Ivoryton - where timeless New England charm meets modern comfort. This beautifully maintained home offers the perfect blend of character, quality, and opportunity, making it an ideal year-round residence, weekend retreat, or investment property. Situated in one of Connecticut's most sought-after shoreline communities, this enchanting home is just a short stroll to the vibrant Ivoryton Village, the renowned Ivoryton Playhouse, charming inns, boutique shops, and acclaimed local restaurants. Enjoy country living with Essex, marinas, beaches, and scenic coastal attractions just minutes away. Thoughtfully updated throughout, this home offers peace of mind with numerous capital improvements, including a new roof, a new driveway, an energy-efficient Mitsubishi split-duct heating and cooling system with programmable Eco thermostats, updated windows and insulation, updated electrical and plumbing, a newer well pressure tank, and an updated septic system. The oversized detached garage is a rare bonus, featuring a spacious loft, dedicated electrical service, and its own circuit breaker.

52 Pond Meadow Rd, Essex
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