Middlesex Real Estate

Middlesex Real Estate

Welcome to Middlesex, a hidden gem nestled in the heart of Yates County, New York. This charming town offers a picturesque blend of natural beauty and small-town warmth, making it an ideal place for those seeking a peaceful retreat or a vibrant community to call home.

Surrounded by the stunning landscapes of the Finger Lakes region, Middlesex boasts breathtaking views, lush vineyards, and serene lakes, perfect for outdoor enthusiasts. Whether you enjoy hiking the scenic trails, fishing in the crystal-clear waters of nearby Canandaigua Lake, or exploring the local wineries, there’s no shortage of activities to keep you engaged.

Middlesex is steeped in rich history, with a welcoming community that prides itself on its strong sense of camaraderie. Residents enjoy a slower pace of life, where neighbors become friends, and community events bring everyone together. The town features a variety of local shops, farmers' markets, and cozy eateries that highlight the region's agricultural roots and culinary delights.

Families will appreciate the quality of life here, with access to well-regarded schools and safe neighborhoods. The town's commitment to preserving its natural beauty and fostering a close-knit community atmosphere makes it an attractive choice for families, retirees, and young professionals alike.

With its idyllic surroundings, friendly community, and a wealth of recreational opportunities, Middlesex is more than just a place to live; it’s a place to thrive. Discover the charm of this enchanting town and envision your future in Middlesex, where every day feels like a vacation.

Newest Listings in Middlesex

1247 Shay Road, Middlesex
$200,000
3 Beds ⋅ 2 Baths ⋅ R1724434 MLS
Relax in the peace and quiet this 4.1 acre property has to offer. Its sits nestled behind a small section of woods giving complete privacy. Beyond the tress it opens up to a large level lawn surrounding this single story home with a circular driveway. Rear deck perfect for morning coffee, outdoor dinners and nature watching. You can enjoy the sights and sounds of nature without the hustle and bustle of traffic or noise of neighbors. Inside you will be happy to find 2/3 bedrooms (one is currently an office/ storage room) 2 bathrooms one being an on-suite. A large kitchen with dining space and a peninsula for bar stools perfect for holiday gatherings and special occasions. This opens up to a central livingroom, keeping everyone together. This is where the memories are made! Come see for yourself how this home and property may be perfect for you!

1247 Shay Road, Middlesex
6380 Vine Valley Road Lot #112, Middlesex
$84,900
2 Beds ⋅ 1 Baths ⋅ R1719625 MLS
SPECTACULAR CANANDAIGUA LAKE AT VINE VALLEY PARK! RARE AND BEST LOCATION WITH IMMEDIATE MILLION DOLLAR LAKE VIEW! THIS IS THE MOST AFFORDABLE WAY TO BE ON CANANDAIGUA LAKE. OVER 500'+ OF SAND AND SHALE BEACH AREA! GREAT SPOT TO DOCK YOUR BOAT TOO! TURNKEY READY TO MOVE IN AND ENJOY! BEAUTIFUL AND IMMCACULATE...... WELCOMING YOU AND YOUR GUEST IS AN ENTERTAINMENT SIZED COVERED PORCH WITH LAKE VIEWS. LEADING TO THE INTERIOR WHICH HAS A BEACH VIBE FEATURING A LIVING AREA, KITCHEN WITH BREAKFAST BAR AND DINING ALL WITH LAKE VIEWS! THIS IS ONE FLOOR LIVING AT ITS BEST! SPACIOUS OWNER'S BEDROOM AND 2ND BEDROOM AND AN UPDATED BATH TOO! THE VINE VALLEY AREA ON CANANDAIGUA LAKE IS A VERY SPECIAL LOCATION ! THIS WATERFRONT NATURE PARADISE OFFERS BREATHTAKING VIEWS OF THE HILLS AND THE LAKE! VINE VALLEY PARK IS A GREAT COMMUNITY SHARING THE LOVE OF THE LAKE WITH OVER 500' WATERFRONT, DOCKS, COMMUNITY CENTER WITH SOME FEATURED CELEBRATIONS OF SUMMER LIKE THE 4TH OF JULY FIREWORKS & THE "RING OF FIRE" THE SATURDAY EVENING BEFORE LABOR DAY..... MAKES THIS A VERY SPECIAL PLACE TO BE ON CANANDAIGUA LAKE. STEPS AWAY IS THE VINE VALLEY BEACH, BOAT LAUNCH & GENERAL STORE. THIS "KEY WEST" LIKE COMMUNITY IS ONE OF THE BEST KEPT SECRETS ON CANANDAIGUA LAKE. EASY ACCESS TO THE CITY OF CANANDAIGUA WITH GREAT RESTAURANTS, SHOPS & WEGMANS......AND THE ENTIRE FINGER LAKES REGION. START MAKING THOSE SPECIAL CANANDAIGUA LAKE MEMORIES AT VINE VALLEY PARK! ONLY THE STRUCTURE NOT THE LAND IS BEING SOLD. CURRENT LOT RENT IS $11,500 PER SEASON. CURRENT BOAT HOIST LOCATION RENT IS $2,500. (Do not need to have a hoist to be at Vine Valley Park). HOIST CAN BE PURCHASED SEPARATELY. LOT RENT INCLUDES, WATER, SEPTIC & GARBAGE PICK UP. Owner of Vine Valley Park maintains common areas and docks. Mobile home make: Royal Cove 1986 Model 8208-1311-0244-4. Buyer of mobile is subject to​​‌​​​​‌​‌​​​​‌‌​​‌‌​‌‌​​‌​​​‌​‌ l

6380 Vine Valley Road Lot #112, Middlesex
1892 Shay Road, Middlesex
$160,000
3 Beds ⋅ 1 Baths ⋅ R1719257 MLS
Welcome to 1892 Shay Rd! This home sits on just over an acre of land for quiet country living. Located within walking distance to Majestic Hills Golf Course, minutes from local activities such as Bristol Mountain, Hi-Tor Hiking Trails, Canandaigua Lake and much more. You will enjoy 3 bedrooms and one versatile room that can be an additional bedroom, one bathroom w/ double wide walk in shower, eat-in kitchen, livingroom and gorgeous three season room complete with tongue and groove walls and ceiling. From there you will enjoy the beauty of nature and hours of relaxation. Inside you will find some hardwood floors, fireplace with electric in-cert, first floor laundry, thermal windows and walk in pantry. Detached garage with concrete floor, electric service and garage door openers. Shed and outdoor fireplace complete this nice country lot. It ready to make it your own with a little TLC.

1892 Shay Road, Middlesex
34 Vine Valley Park, Middlesex
$39,000
R1710028 MLS
There is still time to enjoy the season at Vine Valley Park! This tastefully decorated 2-bedroom, 1 bath cottage is ready for you to relax and enjoy all that Canandaigua Lake has to offer. Enjoy private lake access, boat launch, community center, and general store. Seasonal living approximately April 15th-October 15th. Annual fee is $10,500 plus $2500 for dock space. Home only, land not included. Park approval required. No rentals permitted.

34 Vine Valley Park, Middlesex
6374 Glenn Avenue, Middlesex
$419,900
2 Beds ⋅ 1 Baths ⋅ R1707987 MLS
SPECTACULAR CANANDAIGUA LAKE COTTAGE GETAWAY! This is what lake living is all about—a charming, character-filled cottage where you can spend your days on the water and your evenings relaxing with family and friends! Tucked away at the end of the street and just one house from Newago Cove, this special property offers an incredible opportunity to enjoy the Canandaigua Lake lifestyle! Enjoy approximately 92' of shared beachfront through the Newago Cove Association, complete with a boat launch, dock & swim platform, plus nearby docking available for your boat! Swim, boat, paddle, fish or simply relax by the water and take in everything this wonderful lake community has to offer. Even better, the cottage has been extensively updated with over $130,000 invested, including a new roof, kitchen, bathroom, flooring & subflooring, lighting, deck enclosure, septic system, driveway, landscaping, new PEX water lines & more—so you can spend less time working and more time enjoying the lake! Inside, this quintessential lake cottage is loaded with warmth, character and charm! The designer white & bright kitchen features gorgeous soft-close Shaker-style cabinetry, stainless steel appliances and a breakfast bar. A fun family hangout space with an expansive bar and sitting area overlooks the entertainment-sized dining room with classic wainscoting—perfect for gathering after a day on the lake! The spacious living room captures that unmistakable cottage feel with traditional tongue-and-groove pine cathedral ceilings and access to the porch. A spacious bedroom with cathedral ceilings, plus an additional sleeping loft, provides plenty of room for family and guests—sleeping up to 7, potentially more! Great parking, a storage shed and incredible lake access complete this special getaway. Pack your bags, bring the boat and start making memories—this charming Canandaigua Lake cottage is ready to be enjoyed! SQ.FT from floor plan

6374 Glenn Avenue, Middlesex
105 Indian Village Park, Middlesex
$29,000
1 Beds ⋅ 1 Baths ⋅ R1705479 MLS
THIS IS A GREAT LOW MAINTENANCE WAY TO SPEND TIME ON CANANDIAGUA LAKE AND GET YOUR FEET WET ! Canandaigua Lake access from Indian Village Park lot 105. This sale includes a park model tiny home on lot #105 and the storage shed. This is a 1994 Casa Villa model "1379 Villa Royal" 1 bedroom , 1 full bath unit. Enjoy the shade and outdoor dining if it rains under the attached covered deck. This is a quiet seasonal park on Canandaigua Lake's east side. The Park is opened from May 7th to October 7th. Community well and septic included in the lot rent. Kitchen stove ( propane ), range hood and refrigerator included. Lot rent is $4,850.00 for this lot#105 for the 2026 season not including the boat slip fees. There is a free Town of Middlesex public boat launch about 5 minutes down the road at the town park. Swimming beach owned by Indian Village Park is available to tenants. The park charges additional fees for boat slips, jetski slip, and kayak storage on the shared beachfront. "Small Dock" /jetski $ 1,500.00, Boat slips from $3,455.00 to $3,855.00 per season and Kayak racks rent $155.00/season. This unit has a 3 yr old Metal roof. Seller will supply a bill of sale for the unit and a copy of the Certificate of Origin. Tenants are responsible for their own electric and propane.

105 Indian Village Park, Middlesex
264 E Lake Road, Middlesex
$369,900
3 Beds ⋅ 1 Baths ⋅ R1690756 MLS
CANANDAIGUA LAKE COTTAGE - CAMP CONNEMARA is a charming yet eclectic OLD WORLD kind of NATUCKET-styled summer lake property. This is the "Get Away" place you have been waiting for all at an AMAZING VALUE! The cottage is LAKE LEVEL with 49' WATERFRONT featuring a dock, hoist and....MILLION DOLLAR VIEWS. The current owners have loved this property for many years. It is being sold turnkey ready to move in. Living Room features a fireplace and beamed ceilings with lake views, opening to a galley kitchen. The first floor has two sleeping areas. The upstairs has two sleeping areas and that scenic balcony to enjoy the morning coffee or a glass of wine to take in those AMAZING SUNSETS! Currently the owners access the property via boat. The property is being sold in "AS IS" condition. The land alone is worth the asking price. Do you want to be the next steward of Camp Connemara? Nearby is the Vine Valley Boat Launch & other boat docking facilities. Short distance to City of Canandaigua with great shops, restaurants and CMAC the entertainment venue. And Naples with the world famous Grape Festival.

264 E Lake Road, Middlesex
1316 Bay Drive, Middlesex
$424,900
4 Beds ⋅ 2 Baths ⋅ R1685456 MLS
Join us on Saturday October 3rd from 11-1 for an OPEN HOUSE! Property is aka as 5246 Sunflower Rd - use this address for GPS - follow signs. Incredible Lakefront Family Home!! Tucked away in a serene park-like setting on 4 private acres, this exceptional four bedrm,2 1/2 bath home offers a rare opportunity to own one of only six homes on beautiful Emerson Lake. With over 380 ft of private lake frontage, you will enjoy unparalleled peace and tranquility on this non-motorized lake, where the sounds of nature replace the noise of boat traffic. A gently graded pathway winds through the property, leading to you own waterfront oasis featuring a picnic pavilion and private dock, perfect for launching kayaks and canoes, casting a fishing line or cooling off with a swim on hot summer days. Inside this lovely home is the open concept floor plan designed for comfortable everyday living and effortless entertaining. Hardwood floors, abundant natural light and a cozy stove create a warm and inviting atmosphere. The spacious kitchen features a breakfast bar and flows seamlessly into the dining and family room areas. A sliding glass door opens to the rear deck, where stunning lake views provide the perfect backdrop for morning coffee or evening gatherings. Convenient first floor living includes a large laundry/mud room with half bath located between the garage and the kitchen. The impressive first floor primary suite showcases beautiful wood accents, a fireplace and a private exterior entrance, offering potential for an in-laws suite or guest quarters. Upstairs you will find 3 generously sized bedrooms and a large full bath. The finished walkout lower level expands your living space with a large rec room centered around a pellet stove, which serves as the home's primary heat source. A dedicated workshop area provides plenty of room for hobbies, projects and storage. Whether you are seeking a year-round residence, vacation getaway or waterfront sanctuary, this unique Emerson Lake property offers the perfect combination of privacy, recreation and natural beauty. (Square footage includes approx 600 sqft of finished space in lower level, as per seller.)

1316 Bay Drive, Middlesex
Start Your Search

How much is your home worth?

Get instant property value now!