Recently Sold Homes in Middletown, CT

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SOLD DEC 5, 2025

ABOUT THIS HOME
Recently Sold Home in Middletown, CT:
Opportunity is knocking! South Farms area freshly updated 900 sq. ft. home with 1 bedroom, 1.5 baths, office, living room, kitchen, set on 3.14 acres with a two-level barn. Potential for one lot sub-division w/ variance. Build up on the house, add an ADU -- so many options! This was part of a working farm up until about 10 years ago. Frontage on Chamberlain and Chauncy. Could be a great hobby farm for horses, alpacas, sheep, goats, or a vineyard. Only limited by your imagination. Or -- just enjoy the privacy!

$330,000 Last sold price

2 beds1.5 baths900 sq ft

342 Chamberlain Rd, Middletown, CT 06457

SOLD OCT 20, 2025

ABOUT THIS HOME
Recently Sold Home in Middletown, CT:
* Seller is requesting that offers be submitted by Monday, September 15, 2025 at 6:00pm. Thank you for showing! * Built in 1949, this charming Cape Cod home is ready for your personal touch! This 2 bedroom, 1.5 bath home features a 2 car detached garage and sits on 1.12 acres near Dooly Pond. The main level offers an eat-in kitchen, full bath, cozy living room with fireplace along with the primary and secondary bedrooms. The second floor offers an unheated expansion attic and provides the potential for two additional rooms. Half- bath in basement. Furnace was installed 9/2024 and oil tank is 2016. The property offers ample, well-lit parking lot style along with two separate access points

$325,000 Last sold price

2 beds1.5 baths1,040 sq ft

1904 S Main St, Middletown, CT 06457

SOLD SEP 22, 20253D WALKTHROUGH

ABOUT THIS HOME
Recently Sold Home in Middletown, CT:
Fantastic Riverbend Cape! This amazing floor plan offers it all. Open living room large windows and beautiful fireplace, large center dining room, good size kitchen open to large dining room/dining area. First floor primary bedroom with full bath and walkin closet. Additional den/office and powder room. The upper level of this abode offers 2 large bedrooms and an additional full bath. This amazing home sits on a beautiful lot offering an oversized deck stepping out onto a picturesque backyard with patio and oversized shed, all perfect for those summer gatherings or enjoying the serenity of nature. Topping it off all of this is completely fenced in. Some additional features includes central

$429,900 Last sold price

3 beds2.5 baths2,076 sq ft

20 Benjamin Ln, Middletown, CT 06457

SOLD DEC 5, 20253D WALKTHROUGH

ABOUT THIS HOME
Recently Sold Home in Middletown, CT:
A Riverbend beauty! This home boasts large rooms, front vaulted living room, center dining room, large eat-in kitchen with granite counters and oversized family room with fireplace. This floor plan also offers 1st floor laundry. The upstairs of this abode includes a large loft area with cabinetry, 2 generously-sized bedrooms and an oversized primary with en suite. Some additional features include new windows on 1st level, solar panels have a loan of $219 month - not leased. This can be paid down. New hot water heater. Newer furnace and A/C, sprinkler system. Plumbing completely redone in 2023. Appliances are 7 years old. Basement ceiling finished with recessed lights, waiting for your final

$429,900 Last sold price

3 beds2.5 baths2,031 sq ft

101 Morning Glory Dr, Middletown, CT 06457

SOLD DEC 12, 2025

ABOUT THIS HOME
Recently Sold Home in Middletown, CT:
Welcome Home! This beautifully maintained Colonial offers the perfect blend of comfort and functionality, set on a private lot surrounded by nature. Featuring 3 spacious bedrooms and 2.5 baths, this home is move-in ready and designed to impress. Step inside to find an inviting open layout with hardwood floors, a bright kitchen with granite counters, center island cooktop, and double ovens-perfect for entertaining. The kitchen flows seamlessly into the dining and living areas with a cozy fireplace. Upstairs, the large primary suite includes a vaulted ceiling, walk-in closet, and ensuite bath. Enjoy year-round comfort with central air and peace of mind with a new roof. The 2-car garage provi

$550,000 Last sold price

3 beds2.5 baths2,578 sq ft

115 Meadowood Dr, Middletown, CT 06457

Property at 90 Briarwood Ln, Middletown, CT 06457, 3 beds, 2.5 baths

$450,000 Last sold price

3 beds2.5 baths1,512 sq ft

90 Briarwood Ln, Middletown, CT 06457

Property at 80 Elizabeth Ln, Middletown, CT 06457, 3 beds, 3 baths

$535,000 Last sold price

3 beds3 baths2,310 sq ft

80 Elizabeth Ln, Middletown, CT 06457

Property at 166 Elizabeth Ln, Middletown, CT 06457, 3 beds, 2 baths

$407,000 Last sold price

3 beds2 baths1,426 sq ft

166 Elizabeth Ln, Middletown, CT 06457

Property at 30 Denison Rd, Middletown, CT 06457, 4 beds, 2 baths

$415,000 Last sold price

4 beds2 baths1,600 sq ft

30 Denison Rd, Middletown, CT 06457

Property at 6 Blue Acre Rd, Middletown, CT 06457, 3 beds, 2.5 baths

$455,000 Last sold price

3 beds2.5 baths2,287 sq ft

6 Blue Acre Rd, Middletown, CT 06457

Property at 833 East St, Middletown, CT 06457, 4 beds, 1 bath

$353,000 Last sold price

4 beds1 bath1,260 sq ft

833 East St, Middletown, CT 06457

Property at 3 Prospect Pl, Middletown, CT 06457, 2 beds, 1 bath

$150,000 Last sold price

2 beds1 bath735 sq ft

3 Prospect Pl, Middletown, CT 06457

Property at 181 Fowler Ave, Middletown, CT 06457, 3 beds, 2 baths

$325,000 Last sold price

3 beds2 baths1,638 sq ft

181 Fowler Ave, Middletown, CT 06457

Property at 2332 S Main St, Middletown, CT 06457, 3 beds, 1 bath

$217,500 Last sold price

3 beds1 bath758 sq ft

2332 S Main St, Middletown, CT 06457

Property at 154 Front St, Middletown, CT 06457, 2 beds, 1.5 baths

$272,000 Last sold price

2 beds1.5 baths1,103 sq ft

154 Front St, Middletown, CT 06457

Property at 281 Old Mill Rd, Middletown, CT 06457, 3 beds, 2.5 baths

$410,000 Last sold price

3 beds2.5 baths1,902 sq ft

281 Old Mill Rd, Middletown, CT 06457

Property at 11 Little River Ln, Middletown, CT 06457, 3 beds, 1.5 baths

$320,000 Last sold price

3 beds1.5 baths1,164 sq ft

11 Little River Ln, Middletown, CT 06457

Property at 68 Orchard Hill Ln, Middletown, CT 06457, 3 beds, 1.5 baths

$435,000 Last sold price

3 beds1.5 baths2,254 sq ft

68 Orchard Hill Ln, Middletown, CT 06457

Property at 40 Batt St, Middletown, CT 06457, 2 beds, 1 bath

$250,000 Last sold price

2 beds1 bath912 sq ft

40 Batt St, Middletown, CT 06457

Property at 311 E Ridge Rd, Middletown, CT 06457, 3 beds, 2.5 baths

$485,000 Last sold price

3 beds2.5 baths1,784 sq ft

311 E Ridge Rd, Middletown, CT 06457

Property at 37 Timber Ridge Rd, Middletown, CT 06457, 5 beds, 2.5 baths

$520,000 Last sold price

5 beds2.5 baths2,308 sq ft

37 Timber Ridge Rd, Middletown, CT 06457

Property at 40 Meadowbrook Rd, Middletown, CT 06457, 3 beds, 2 baths

$330,000 Last sold price

3 beds2 baths960 sq ft

40 Meadowbrook Rd, Middletown, CT 06457

Property at 158 Newtown St, Middletown, CT 06457, 2 beds, 1 bath

$355,000 Last sold price

2 beds1 bath1,288 sq ft

158 Newtown St, Middletown, CT 06457

Property at 56 Jefferson Ave, Middletown, CT 06457, 4 beds, 2 baths

$400,000 Last sold price

4 beds2 baths1,629 sq ft

56 Jefferson Ave, Middletown, CT 06457

Property at 108 Barry Ct, Middletown, CT 06457, 2 beds, 1 bath

$225,000 Last sold price

2 beds1 bath912 sq ft

108 Barry Ct, Middletown, CT 06457

Property at 80 Russell St, Middletown, CT 06457, 4 beds, 3 baths

$350,000 Last sold price

4 beds3 baths2,089 sq ft

80 Russell St, Middletown, CT 06457

Property at 10 Yellow Green Rd, Middletown, CT 06457, 4 beds, 2 baths

$380,000 Last sold price

4 beds2 baths1,536 sq ft

10 Yellow Green Rd, Middletown, CT 06457

Property at 82 Basswood Dr, Middletown, CT 06457, 2 beds, 1 bath

$305,000 Last sold price

2 beds1 bath960 sq ft

82 Basswood Dr, Middletown, CT 06457

Property at 16 Snow Rdg S, Middletown, CT 06457, 4 beds, 2.5 baths

$520,000 Last sold price

4 beds2.5 baths2,813 sq ft

16 Snow Rdg S, Middletown, CT 06457

Property at 311 Coleman Rd, Middletown, CT 06457, 4 beds, 1.5 baths

$545,000 Last sold price

4 beds1.5 baths1,939 sq ft

311 Coleman Rd, Middletown, CT 06457

Property at 193 Hendley St, Middletown, CT 06457, 3 beds, 1.5 baths

$366,000 Last sold price

3 beds1.5 baths1,677 sq ft

193 Hendley St, Middletown, CT 06457

Property at 95 Barbara Rd, Middletown, CT 06457, 2 beds, 2 baths

$290,000 Last sold price

2 beds2 baths1,312 sq ft

95 Barbara Rd, Middletown, CT 06457

Property at 74 Clarence Ct, Middletown, CT 06457, 3 beds, 2.5 baths

$485,000 Last sold price

3 beds2.5 baths2,217 sq ft

74 Clarence Ct, Middletown, CT 06457

Property at 80 Pond Pl, Middletown, CT 06457, 3 beds, 2 baths

$425,000 Last sold price

3 beds2 baths1,672 sq ft

80 Pond Pl, Middletown, CT 06457

Property at 22 Belvidere Ter, Middletown, CT 06457, 3 beds, 2.5 baths

$408,000 Last sold price

3 beds2.5 baths1,960 sq ft

22 Belvidere Ter, Middletown, CT 06457

Property at 29 Talias Trl, Middletown, CT 06457, 4 beds, 2.5 baths

$673,000 Last sold price

4 beds2.5 baths2,432 sq ft

29 Talias Trl, Middletown, CT 06457

Property at 100 Jack English Dr, Middletown, CT 06457, 4 beds, 2.5 baths

$555,000 Last sold price

4 beds2.5 baths2,219 sq ft

100 Jack English Dr, Middletown, CT 06457

Property at 55 Trolley Crossing Ln #55, Middletown, CT 06457, 2 beds, 1.5 baths

$223,000 Last sold price

2 beds1.5 baths1,136 sq ft

55 Trolley Crossing Ln #55, Middletown, CT 06457

Property at 49 Rising Trail Dr #49, Middletown, CT 06457, 3 beds, 1.5 baths

$190,000 Last sold price

3 beds1.5 baths1,232 sq ft

49 Rising Trail Dr #49, Middletown, CT 06457

Property at 113 Trolley Crossing Ln #113, Middletown, CT 06457, 1 bed, 1 bath

$154,000 Last sold price

1 bed1 bath644 sq ft

113 Trolley Crossing Ln #113, Middletown, CT 06457

Property at 5 Sonoma Ln #5, Middletown, CT 06457, 2 beds, 2.5 baths

$590,000 Last sold price

2 beds2.5 baths1,840 sq ft

5 Sonoma Ln #5, Middletown, CT 06457

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Recently Sold Homes in Middletown

There are currently 148 recently sold homes for sale in Middletown at a median listing price of $340K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Middletown stay on the market for 38 days and receive 1 offers. This map is refreshed with the newest listings in Middletown every 15 minutes.

In the past month, 43 homes have been sold in Middletown. In addition to houses in Middletown, there were also 35 condos, 1 townhouse, and 10 multi-family units for sale in Middletown last month. Middletown is a minimally walkable city in Connecticut with a Walk Score of 28. Middletown is home to approximately 47,560 people and 26,247 jobs. Find your dream home in Middletown using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Middletown are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Middletown. Our Middletown real estate stats and trends will give you more information about home buying and selling trends in Middletown. If you're looking to sell your home in the Middletown area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Middletown with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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