Middlefield, CT Homes

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  /40

  $399,900

  • 2 Beds
  • 2 Baths
  • 1,208 Sq Ft

  161 Peters Ln, Rockfall, CT 06481

  This charming ranch boasts modern up-dates throughout offering a fresh and inviting interior that blends comfort with style. Featuring a totally remodeled kitchen with sleek appliances and granite counters and a large dining area. No ownership headaches ahead for many years because all mechanicals are less than 10 years young -- furnace, oil tank, roof, well tank,etc. Step outside to discover the

  Nancy Currlin William Raveis Real Estate

  161 Peters Ln, Rockfall, CT 06481
• 

  Explore Middlefield

• 

  

  

  /20

  $6,899 per month

  • 2 Beds
  • 1.5 Baths
  • 1,194 Sq Ft
  • Condo for Rent

  6 Nancy Ln Unit ID1261565P, Middlefield, CT 06455

  This beautifully remodeled two-bedroom single-family home is situated on a large private lot in the quaint town of Middlefield, Connecticut. Centrally located, it is just a short drive from Wesleyan University, Lyman Orchards, Middlesex Hospital, Lake Beseck, and much more. No matter your reason for visiting the area, this home is sure to leave you feeling satisfied and wanting to return again

  6 Nancy Ln Unit ID1261565P, Middlefield, CT 06455
• 

  $175,000 Sold Sep 19, 2025

  • 1,154 Sq Ft
  • $152/SF
  • 89 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1986

  6 Bittersweet Ridge Unit A, Middlefield, CT 06455

  Welcome to this beautifully updated and freshly painted, over-55 unit that blends comfort and style in a highly desirable community. Boasting hardwood floors throughout and an open floor plan, this unit feels much more spacious than its square footage suggests. Enjoy the 6" crown molding and flat ceilings, which add a touch of elegance to the living and dining areas. The custom remodeled bath and

  John Zubretsky Century 21 AllPoints Realty

  6 Bittersweet Ridge Unit A, Middlefield, CT 06455
• 

  Est $582,075 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,717 Sq Ft

  8 Crest View Dr, Rockfall, CT 06481

  8 Crest View Dr, Rockfall, CT 06481
• 

  

  

  /40

  $449,000 Pending

  • 4 Beds
  • 3 Baths
  • 3,340 Sq Ft

  140 Main St, Rockfall, CT 06481

  This split-level 4BD, 3BA home offers over 3,000 square feet of above grade living space and includes a beautiful in-law apartment with its own sunroom - making this house a fully zoned and permitted 2-family! The property features a 3-car attached garage, a large level lot, and a fenced backyard featuring a beautiful deck ready for entertaining. The spacious front porch provides a welcoming

  Christina Bates Coldwell Banker Realty

  140 Main St, Rockfall, CT 06481
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  /21

  $2,200 per month

  • 2 Beds
  • 1 Bath
  • 932 Sq Ft
  • House for Rent

  118 Lake Shore Dr, Middlefield, CT 06455

  Don't miss this rare opportunity for lakefront living in a charming, well-kept cottage! 2 good sized bedrooms, 1 bath and a laundry/office/den space, open concept kitchen/dining and a cozy living room, give you ample space. Enjoy stunning water views from every room in this adorable retreat, complete with a private gazebo and serene waterfront setting. Whether you're sipping morning coffee on the

  Roberta Whalen LAER Realty Partners

  118 Lake Shore Dr, Middlefield, CT 06455
• 

  $310,000 Sold Sep 18, 2025

  • 610 Sq Ft
  • $508/SF
  • 19 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1947

  239 Baileyville Rd, Middlefield, CT 06455

  Direct waterfront on Lake Beseck! This small cottage offers a rare opportunity to create your own lakeside retreat. The property is in need of significant renovation, but with vision and effort, it can be transformed into the perfect getaway. The home features a newer treks deck overlooking the water-an ideal spot to relax and take in the lake views. Bring your ideas and make this property shine.

  Lori Campbell Coldwell Banker Realty

  239 Baileyville Rd, Middlefield, CT 06455
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  Est $482,020 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 2,827 Sq Ft

  14 Massasoit Rd, Middlefield, CT 06455

  14 Massasoit Rd, Middlefield, CT 06455
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  /39

  $399,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,843 Sq Ft

  25 Aresco Dr, Rockfall, CT 06481

  Charming Ranch in Rockfall --- Tucked away on a peaceful cul-de-sac in the Rockfall section of Middlefield, this beautifully maintained ranch offers comfort, character, and convenience. Step inside to a tastefully remodeled kitchen with rich cabinetry and hardwood floors that flow through much of the home. A cozy living room with a fireplace and picture window invites relaxation, while a heated

  David Gallitto Huntsman,Meade & Partners Comp

  25 Aresco Dr, Rockfall, CT 06481
• 

  $900,000 Sold Sep 10, 2025

  • 4,458 Sq Ft
  • $202/SF
  • 82 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1988

  45 Snell Rd, Middlefield, CT 06455

  Located on the Durham/Middlefield border, this farmhouse-style Colonial with Post & Beam Barn is for those who run from cookie cutter, and dream about beautiful, thoughtful design, custom and quality finishes, and grounds that are unmatched. Perched on 2 secluded acres with lush sweeps of lawn, magical garden pathways, pergola, stunning perennials, and multiple bluestone patios on a quiet

  Claudia O'Connell William Raveis Real Estate

  45 Snell Rd, Middlefield, CT 06455
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  Est $434,944 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,946 Sq Ft

  51 Mack Rd, Middlefield, CT 06455

  51 Mack Rd, Middlefield, CT 06455
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  /40

  $392,900 Pending

  • 4 Beds
  • 3.5 Baths
  • 2,776 Sq Ft

  20 Mack Rd, Middlefield, CT 06455

  This very spacious, nearly 3,000 SF colonial WITH IN-LAW, set on 1.43 acres, offers the perfect foundation to create your dream property. With ample room both inside & out, this residence features a separate single floored in-law apt w/ its own private entrance & porch, eat-in Kit, DR/LR combo, full bath & bedrm making it ideal for multi-generational living, guests, or perhaps a home office. The

  Suzy Couture Executive Real Estate Inc.

  20 Mack Rd, Middlefield, CT 06455
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  $298,000 Sold Sep 09, 2025

  • 1,088 Sq Ft
  • $274/SF
  • 44 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1959

  9 Garden Hill Rd, Middlefield, CT 06455

  Nestled on a quiet cul-de-sac in scenic Middlefield, this ranch offers a rare blend of possibility and potential. Yes, it needs updating-but look closer, and you'll see the makings of something truly special. Hardwood floors throughout add warmth and character, central air keeps things comfortable, and recent updates like a newer boiler and solar panels provide a solid foundation for your vision.

  Debbie Huscher Real Broker CT, LLC

  9 Garden Hill Rd, Middlefield, CT 06455
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  Est $413,565 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,248 Sq Ft

  5 Meriden Rd, Rockfall, CT 06481

  5 Meriden Rd, Rockfall, CT 06481
• 

  /2

  $524,900 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,063 Sq Ft

  31 High St Unit Lot 2, Middlefield, CT 06455

  A beautiful subdivision to be built with 4 lots to choose from, and 3 different house plans. The Ashwood model consists of 2,614 sq ft, 4 bedrooms, 2.5 bathrooms, 2 car attached garage. The Aspen model is 2,272 sq ft, 4 bedrooms, 2.5 bathrooms and a 2 car attached garage. Lastly, the Beechwood model has a first-floor master, 2,063 sq ft, 3 bedroom, 2.5 bathrooms, and 2 car garage attached. This

  Milena Mineri RE/MAX One

  31 High St Unit Lot 2, Middlefield, CT 06455
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  $409,500 Sold Sep 03, 2025

  • 1,960 Sq Ft
  • $209/SF
  • 83 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1969

  30 Dwight Rd, Middlefield, CT 06455

  Welcome to a lifestyle, not just a location! Nestled on a quiet cul-de-sac in a friendly Middlefield neighborhood, this well-maintained Colonial offers charm, comfort, and an incredibly convenient lifestyle. Within 3 miles, enjoy top local attractions-Lyman Orchards, Lake Beseck, Powder Ridge, Indian Springs Golf, Peckham Park, and Wadsworth Falls. Whether it's apple picking, kayaking, or hitting

  Debbie Huscher Real Broker CT, LLC

  30 Dwight Rd, Middlefield, CT 06455
• 

  Est $656,738 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,949 Sq Ft

  15 Orchard Ln, Middlefield, CT 06455

  15 Orchard Ln, Middlefield, CT 06455
• 

  

  /3

  $125,000

  • Land
  • 5.15 Acres
  • $24,272 per Acre

  0 Kikapoo Rd, Middlefield, CT 06481

  **For Sale: 5.15 Acres in Middlefield** Discover the beauty of Middlefield, offering breathtaking views and endless possibilities. Nestled near the serene Lake Beseck, this land is perfect for your dream cottage, home, or even a small retreat. **Why Middlefield?** Middlefield is known for its charming community, outdoor recreation, and central CT location. Enjoy the tranquility of rural living

  Heather Kilbourn Cavanaugh & Company LLC

  0 Kikapoo Rd, Middlefield, CT 06481
• 

  $550,000 Sold Aug 28, 2025

  • 2,812 Sq Ft
  • $196/SF
  • 91 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1981

  32 Powder Hill Rd, Middlefield, CT 06455

  Vacation Living All Year Long - Want to feel like you're on vacation year-round? Welcome to 32 Powder Hill Road, where every season brings new adventures right outside your door. Located directly across from Powder Ridge Ski Resort, you'll enjoy skiing, fine dining, and entertainment just steps away. Tee off at any of four nearby golf courses or spend your days picking apples, peaches, and

  Margaret Curry William Raveis Real Estate

  32 Powder Hill Rd, Middlefield, CT 06455
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  Est $739,892 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,182 Sq Ft

  43 High Meadow Ln, Middlefield, CT 06455

  43 High Meadow Ln, Middlefield, CT 06455
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  /37

  $349,900 Pending

  • 3 Beds
  • 1 Bath
  • 2,330 Sq Ft

  18 Rosemary Ct, Middlefield, CT 06455

  One-Level Living at Its Best! This well-loved home, cherished by the same family for over 36 years, offers comfort, space, and a fantastic location. Featuring 3 generously sized bedrooms, 1 full bath, and beautiful hardwood floors throughout, this solid home is ready for its next chapter. Enjoy 6 spacious rooms, a partially finished basement for extra living space, and sliders off the enclosed

  Katrina Pratt Rainbow Realty

  18 Rosemary Ct, Middlefield, CT 06455
• 

  $960,000 Sold Aug 22, 2025

  • 3,536 Sq Ft
  • $271/SF
  • 75 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1947

  22 Lake Shore Dr, Middlefield, CT 06455

  LAKE LIVING at its finest! Beautiful Lake Beseck is a true gem-conveniently located just minutes from I-91 and a short drive to New Haven, Hartford, or even NYC. This stunning property makes the most of everything lake life has to offer: breathtaking views, lush grassy areas leading to the shoreline, and a spacious cantilevered dock that truly wows. Boat, swim, sail, jet ski, or fish right from

  Jamie Clark Berkshire Hathaway NE Prop.

  22 Lake Shore Dr, Middlefield, CT 06455
• 

  Est $344,352 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft

  39 Maryland Dr, Middlefield, CT 06455

  39 Maryland Dr, Middlefield, CT 06455
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  /38

  $250,000 Pending

  • 2 Beds
  • 1 Bath
  • 1,258 Sq Ft

  51 Lake Shore Dr, Middlefield, CT 06455

  Location, location, location! This house is directly across from the town beach giving it awesome views and maximum convenience. It might be a tear-down -- and it might be salvageable with vision-but either way it's a diamond in the rough that has mountains of potential. It has a second house that must be sold with it -- 53 Lake Shore! An adorable 260 sq.ft. cottage that adds $50,000 to the price

  Nancy Currlin William Raveis Real Estate

  51 Lake Shore Dr, Middlefield, CT 06455
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  $615,000 Sold Jul 29, 2025

  • 3,472 Sq Ft
  • $177/SF
  • 22 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 2010

  2 Crestview Dr Unit 2, Rockfall, CT 06481

  Enjoy gracious living in this small 55+ community, nestled in a quiet country setting yet only minutes from Middletown center. Built by an established contractor, this home features upgrades galore. Entertainers and cooks will delight in the well-appointed kitchen. From the pot filler over the Viking cook top, to the wine cooler located at the center island, this warm inviting space is the heart

  Victoria Sammis Sammis Realty

  2 Crestview Dr Unit 2, Rockfall, CT 06481
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  Est $365,707 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,189 Sq Ft

  49 Mattabeseck Rd, Middlefield, CT 06455

  49 Mattabeseck Rd, Middlefield, CT 06455
• 

  

  /40

  $644,900 Pending

  • 4 Beds
  • 3.5 Baths
  • 3,212 Sq Ft

  135 Harvest Woods Rd, Rockfall, CT 06481

  A MUST see is this absolutely stunning 4 Bedroom, 3.5 Bath Colonial with 3,212 square feet on 1.08 acres in a picturesque New England setting. Inside, enjoy a quaint Family Room with wood-burning fireplace and sliders to the deck, Huge eat-in Kitchen with concrete counters, stainless & black appliances, Spacious peninsula w/seating for 4-5, Dining Area, pantry closet, and butler pantry area. A

  Jeff Coleman Hagel & Assoc. Real Estate

  135 Harvest Woods Rd, Rockfall, CT 06481
• 

  $357,500 Sold Jul 25, 2025

  • 1,142 Sq Ft
  • $313/SF
  • 6 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1962

  130 Cherry Hill Rd, Middlefield, CT 06455

  Experience Exceptional Living in Middlefield, CT! Located in a sought-after area known for outdoor recreation, this home is just minutes from Powder Ridge Mountain Park & Resort, Lyman Orchards, and a short walk to Wadsworth Falls State Park's Blue Trailhead. This beautifully maintained 3-bedroom, 1.5-bath ranch with one-car carport offers the ease of single-level living combined with style and

  Natalee King Coldwell Banker Realty

  130 Cherry Hill Rd, Middlefield, CT 06455
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  Est $337,156 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,194 Sq Ft

  15 Mohican Rd, Middlefield, CT 06455

  15 Mohican Rd, Middlefield, CT 06455
• 

  

  /3

  $129,000 Pending

  • Land
  • 4.24 Acres
  • $30,425 per Acre

  80 West St, Middlefield, CT 06455

  Discover the perfect canvas for your dream home on this stunning 4.5+ acre parcel of raw land, ideally situated in the heart of Middlefield. Tucked away yet perfectly centered to enjoy all the town has to offer, this property places you minutes from the charming pick-your-own experiences at Lyman Orchards, scenic rounds at Indian Springs Golf Course, and year-round adventure at Powder Ridge Ski

  Casey Meadows William Raveis Real Estate

  80 West St, Middlefield, CT 06455
• 

  $375,000 Sold Jul 25, 2025

  • 2,576 Sq Ft
  • $146/SF
  • 116 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1970

  38 High St, Middlefield, CT 06455

  Step into this lovely 1900 Colonial, full of warmth and character, nestled on a spacious 2.51-acre lot. This home has been lovingly cared for, offering a perfect balance of charm and potential for your personal touch. The main floor features beautiful hardwood floors throughout, with an inviting living room centered around a cozy fireplace, creating the perfect space to relax and unwind. The

  Michelle Pirruccio Carl Guild & Associates

  38 High St, Middlefield, CT 06455
• 

  Est $380,898 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,604 Sq Ft

  17 Dwight Rd, Middlefield, CT 06455

  17 Dwight Rd, Middlefield, CT 06455
• 

  

  /22

  $275,000 Under Contract

  • 2 Beds
  • 1 Bath
  • 672 Sq Ft

  10 Massasoit Rd, Middlefield, CT 06455

  Lake life made easy! This charming Lake Beseck cottage offers seasonal water views and a short stroll to the beach-so your weekends can start with a swim, a paddleboard ride, or a sunset picnic without ever packing the car. Whether you're simplifying full-time or craving a weekend retreat, this home delivers a lifestyle that feels like vacation every day. Wrapped in a white picket fence and

  Debbie Huscher Real Broker CT, LLC

  10 Massasoit Rd, Middlefield, CT 06455
• 

  $285,000 Sold Jul 24, 2025

  • 1,726 Sq Ft
  • $165/SF
  • 6 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1986

  10 Bittersweet Ridge Unit 10, Middlefield, CT 06455

  ***Highest & Best due tomorrow, 6/10 by EOD. Tucked in the peaceful and highly sought-after Bittersweet Ridge 55+ community in Middlefield, this beautifully maintained 2-bedroom, 1.5-bath ranch-style condo offers 1,726 sq ft of finished space, including a fully remodeled basement. Ideal for low-maintenance living, the home blends comfort, style, and convenience in a serene countryside setting.

  Jessica Boswell LPT Realty

  10 Bittersweet Ridge Unit 10, Middlefield, CT 06455
• 

  Est $325,357 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 966 Sq Ft

  5 Wildwood Cir, Rockfall, CT 06481

  5 Wildwood Cir, Rockfall, CT 06481
• 

  

  /28

  $305,000 Under Contract

  • 2 Beds
  • 1 Bath
  • 760 Sq Ft

  87 Lake Shore Dr, Middlefield, CT 06455

  Start living the Lake Life! 2 Bedroom, 1 Bath Ranch home with a view and short walk to the beach of beautiful Lake Beseck. Remodeled and updated in 2017 including new kitchen and bath, heating system, electrical, plumbing, siding and windows! New water heater 2025 The open floor plan creates an inviting area with hardwood floors, vaulted ceiling and masonry fireplace in the Living Room. Kitchen

  Phil Giampietro Coldwell Banker Realty

  87 Lake Shore Dr, Middlefield, CT 06455
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  $1,002,500 Sold Jul 10, 2025

  • 2,055 Sq Ft
  • $488/SF
  • 1 Day On Market

  • 3 Beds
  • 4 Baths
  • Built 2017

  86 Lake Shore Dr, Middlefield, CT 06455

  Discover this stunning perfect lakefront retreat in this beautifully designed 3-level home just eight years young! Breathtaking year-round views, modern amenities, gas firepit, and your own private dock make you feel like you're always on vacation. Step inside to find a spacious open layout perfect for family living or entertaining guests. The gourmet kitchen features high-end appliances, sleek

  Nancy Currlin William Raveis Real Estate

  86 Lake Shore Dr, Middlefield, CT 06455
• 

  Est $447,846 Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 2,144 Sq Ft

  20 Burt Dr, Middlefield, CT 06455

  20 Burt Dr, Middlefield, CT 06455
• 

  

  /40

  $749,900 Under Contract

  • 4 Beds
  • 2 Baths
  • 2,505 Sq Ft

  88 Powder Hill Rd, Middlefield, CT 06455

  Nestled in the heart of scenic Middlefield, this distinctive and beautifully maintained 4 bedroom 2.5 bathroom property offers a rare blend of classic New England character and modern flexibility. Inside on the first floor, an open-concept kitchen and dining area invite gathering and entertaining, seamlessly flowing into a sunroom-style flex space with room to grow-ideal for a home office,

  Gary Marino William Raveis Real Estate

  88 Powder Hill Rd, Middlefield, CT 06455
• 

  $445,000 Sold Jul 07, 2025

  • 2,740 Sq Ft
  • $162/SF
  • 28 Days On Market

  • 5 Beds
  • 2 Baths
  • Built 1890

  65 Spring St, Rockfall, CT 06481

  Blending old and new, this gracious Colonial home welcomes you to explore and imagine the space and all of it's possibilities. Nestled on a private, lightly wooded 1.17 acre lot, the original 1890 home in the center has been expanded in the last 20 years with two major additions on either side, yielding 2740 square feet of living space with 5 bedrooms and 2 full baths (and room to add another to

  Claudia O'Connell William Raveis Real Estate

  65 Spring St, Rockfall, CT 06481

Showing Results 1 - 40, Page 1 of 18