Old Saybrook, CT homes for sale & real estate

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OPEN SAT, 11:30AM TO 1PM

ABOUT THIS HOME
Old Saybrook, CT Homes for Sale
Discover the best of Connecticut shoreline living at 11 Trolley Crossing in Old Saybrook-a private 3+ acre compound blending classic Colonial architecture with modern luxury. Designed for those who value space, comfort, and connection, this 3,600 sq ft residence invites you to experience an exceptional lifestyle surrounded by nature and minutes from the coast. A covered front porch opens to expansive, light-filled rooms where timeless craftsmanship meets everyday convenience. The kitchen fireplace creates a welcoming centerpiece for gatherings, while a second fireplace in the living room adds warmth and style. The first-floor primary suite allows for true one-level living, complemented by f

$1,190,000

5 beds3.5 baths3,664 sq ft

11 Trolley Xing, Old Saybrook, CT 06475

3.2 acre lot • 3 garage spots • Pool

COMING SOON

ABOUT THIS HOME
Old Saybrook, CT Homes for Sale
Impeccably Renovated Waterfront Condominium in Coveted Sheltered Cove! Welcome to this beautifully renovated, turn-key condominium in the highly sought-after Sheltered Cove community of Old Saybrook. Every detail has been thoughtfully updated, blending modern comfort with timeless coastal charm. Step into a bright, open-concept kitchen featuring sleek stainless steel appliances, abundant storage, and a seamless flow to the dining and living areas-perfect for entertaining or simply relaxing while taking in breathtaking views of the Connecticut River, marsh, and passing boats. Wake each morning to spectacular sunrises and unwind with stunning sunsets from the comfort of your home. Upstairs,

$735,000

2 beds2.5 baths2,310 sq ft

100 Dudley Ave Unit D20, Old Saybrook, CT 06475

$167 HOA • Garage • Pool

ABOUT THIS HOME
Old Saybrook, CT Homes for Sale
Welcome to 5 Foxhollow Road, a meticulously renovated 4 bedroom, 3 bath Cape located on a quiet cu-de-sac on 1.84 acres. This property offers the unique blend of exceptional privacy with a prime central location convenient to shopping and dining, hiking and biking trails, and all the beauty of coastal Connecticut. This secluded retreat, however, offers easy access to all things in Essex, Westrook and Old Saybrook and only minutes from entrances to I-95 and route 9. The home features an open floor plan with large eat-in chef's kitchen, large island, and plenty of storage. The adjacent family room is perfect for lounging or entertaining. Newly re-finished gleaming hardwood floors, soft linen

$749,000

4 beds3 baths2,142 sq ft

5 Fox Hollow Rd, Old Saybrook, CT 06475

1.84 acre lot • 2 garage spots • Built 1987

ABOUT THIS HOME
Old Saybrook, CT Homes for Sale
Unique Multi-Generational Property on 2+ Private Acres. A truly rare opportunity: two connected yet fully private residences set on 2.02 serene acres bordering the breathtaking 1,000-acre "Preserve". An impressive (24' x 40') heated, two-story barn with a loft offers endless possibilities for contractors, hobbyists, collectors, or creatives seeking a private studio or workshop. Primary Residence: 3 bedrooms, two full bathrooms, home office option, wrap-around porch, full basement, oil heat & hot water. Second Residence: 2 bedrooms, two full bathrooms, home office option, wrap-around porch, full basement, geothermal warm air + A/C with electric hot water. Perfect for multi-ge

$925,400

3 beds2 baths2,938 sq ft

179 Bokum Rd, Old Saybrook, CT 06475

2.02 acre lot • 2 garage spots • Built 1987

OPEN SAT, 1:30PM TO 2:30PM

ABOUT THIS HOME
Old Saybrook, CT Homes for Sale
No Flood Insurance Required! Built in 2025, 26 Meadowood Lane offers a rare mix of architectural elegance, energy efficiency, and a shoreline lifestyle all outside a flood zone. Just 0.7 mi to Old Saybrook Town Beach, 1.2 mi to Fenwick Golf Course, 1.1 mi to Saybrook Point Marina, 0.9 mi to downtown Main Street, and 1.4 mi to the Old Saybrook train station, this Colonial delivers both convenience and serenity. Inside, red oak floors bathe in natural light through impact-rated windows. The open-concept layout flows through arched transitions to a chef's kitchen featuring a 6-burner gas range, Carrera marble waterfall island, walk-in pantry, and custom cabinetry. From here, sliding doors lead

$1,298,989

3 beds2.5 baths2,236 sq ft

26 Meadowood Ln, Old Saybrook, CT 06475

Custom colonial • Open-concept design • Water views

Property at 24 Cottage Pl, Old Saybrook, CT 06475, 4 beds, 3 baths

$960,000

4 beds3 baths2,516 sq ft

24 Cottage Pl, Old Saybrook, CT 06475

Property at 122 Old Post Rd, Old Saybrook, CT 06475, 3 beds, 2.5 baths

$1,125,000

3 beds2.5 baths2,467 sq ft

122 Old Post Rd, Old Saybrook, CT 06475

Property at 227 Essex Rd, Old Saybrook, CT 06475, 3 beds, 1 bath

$425,000

3 beds1 bath1,032 sq ft

227 Essex Rd, Old Saybrook, CT 06475

Property at 21 Farview Ave, Old Saybrook, CT 06475, 3 beds, 2 baths

$683,000

3 beds2 baths1,664 sq ft

21 Farview Ave, Old Saybrook, CT 06475

Property at 5 Sunrise Ave, Old Saybrook, CT 06475, 3 beds, 1 bath

$499,999

3 beds1 bath1,064 sq ft

5 Sunrise Ave, Old Saybrook, CT 06475

Property at 24 Seabreeze Rd, Old Saybrook, CT 06475, 2 beds, 2 baths

$1,045,000

2 beds2 baths1,952 sq ft

24 Seabreeze Rd, Old Saybrook, CT 06475

Property at 254 Hidden Cove Rd #254, Old Saybrook, CT 06475, 2 beds, 2.5 baths

$574,900

2 beds2.5 baths1,557 sq ft

254 Hidden Cove Rd #254, Old Saybrook, CT 06475

Property at 100 Dudley Ave Unit H43, Old Saybrook, CT 06475, 2 beds, 2.5 baths

$639,000

2 beds2.5 baths1,920 sq ft

100 Dudley Ave Unit H43, Old Saybrook, CT 06475

Property at Town Beach Rd, Old Saybrook, CT 06475, 5 beds, 2.5 baths

$985,000

5 beds2.5 baths3,472 sq ft

Town Beach Rd, Old Saybrook, CT 06475

Property at 25 Maplewood Rd, Old Saybrook, CT 06475, 4 beds, 3.5 baths

$1,199,500

4 beds3.5 baths2,850 sq ft

25 Maplewood Rd, Old Saybrook, CT 06475

Property at 1 Lighthouse Ln, Old Saybrook, CT 06475, 3 beds, 2.5 baths

$939,900

3 beds2.5 baths3,286 sq ft

1 Lighthouse Ln, Old Saybrook, CT 06475

Property at 20 Saltus Dr, Old Saybrook, CT 06475, 5 beds, 7.5 baths

$9,850,000

5 beds7.5 baths9,481 sq ft

20 Saltus Dr, Old Saybrook, CT 06475

Property at 174 Nehantic Trl, Old Saybrook, CT 06475, 1 bed, 1 bath

$1,190,000

1 bed1 bath578 sq ft

174 Nehantic Trl, Old Saybrook, CT 06475

Property at 7 Sharon Ln, Old Saybrook, CT 06475, 4 beds, 2.5 baths

$899,900

4 beds2.5 baths2,636 sq ft

7 Sharon Ln, Old Saybrook, CT 06475

Property at 96 Ayers Point Rd, Old Saybrook, CT 06475, 4 beds, 3 baths

$1,095,000

4 beds3 baths4,109 sq ft

96 Ayers Point Rd, Old Saybrook, CT 06475

Property at 14 Denmore Ln, Old Saybrook, CT 06475, 3 beds, 1 bath

$520,000

3 beds1 bath1,196 sq ft

14 Denmore Ln, Old Saybrook, CT 06475

Property at 96 Fenwood Dr, Old Saybrook, CT 06475, 3 beds, 3 baths

$1,350,000

3 beds3 baths2,326 sq ft

96 Fenwood Dr, Old Saybrook, CT 06475

Property at 26 College St, Old Saybrook, CT 06475, 5 beds, 3 baths

$895,000

5 beds3 baths2,898 sq ft

26 College St, Old Saybrook, CT 06475

Property at 2 Old South Cove Rd, Old Saybrook, CT 06475, 3 beds, 3.5 baths

$1,575,000

3 beds3.5 baths2,500 sq ft

2 Old South Cove Rd, Old Saybrook, CT 06475

Property at 41 Watrous Point Rd, Old Saybrook, CT 06475, 6 beds, 4.5 baths

$4,250,000

6 beds4.5 baths5,536 sq ft

41 Watrous Point Rd, Old Saybrook, CT 06475

Property at 30 Watrous Point Rd, Old Saybrook, CT 06475, 4 beds, 4 baths

$1,475,000

4 beds4 baths4,546 sq ft

30 Watrous Point Rd, Old Saybrook, CT 06475

Property at 13 College St, Old Saybrook, CT 06475, 1 bed, 1 bath

$450,000

1 bed1 bath576 sq ft

13 College St, Old Saybrook, CT 06475

Property at 20 Hill St, Old Saybrook, CT 06475, 2 beds, 2 baths

$749,900

2 beds2 baths1,432 sq ft

20 Hill St, Old Saybrook, CT 06475

Property at 355 Main St, Old Saybrook, CT 06475, 3 beds, 1.5 baths

$729,000

3 beds1.5 baths2,194 sq ft

355 Main St, Old Saybrook, CT 06475

Property at 18 Quarry St, Old Saybrook, CT 06475, 4 beds, 2 baths

$630,000

4 beds2 baths1,760 sq ft

18 Quarry St, Old Saybrook, CT 06475

Property at 23 Briarwood Dr, Old Saybrook, CT 06475, 3 beds, 2 baths

$975,000

3 beds2 baths2,000 sq ft

23 Briarwood Dr, Old Saybrook, CT 06475

Property at 175 N Cove Rd, Old Saybrook, CT 06475, 4 beds, 4.5 baths

$3,750,000

4 beds4.5 baths3,518 sq ft

175 N Cove Rd, Old Saybrook, CT 06475

Property at 143 Sandy Point Rd #143, Old Saybrook, CT 06475, 2 beds, 2.5 baths

$575,000

2 beds2.5 baths1,557 sq ft

143 Sandy Point Rd #143, Old Saybrook, CT 06475

Property at 96 Chalker Beach Rd, Old Saybrook, CT 06475, 3 beds, 1 bath

$649,900

3 beds1 bath870 sq ft

96 Chalker Beach Rd, Old Saybrook, CT 06475

Property at 12 Rocky Point Rd, Old Saybrook, CT 06475, 4 beds, 4.5 baths

$6,400,000

4 beds4.5 baths5,651 sq ft

12 Rocky Point Rd, Old Saybrook, CT 06475

Property at 118 Sandy Point Rd #118, Old Saybrook, CT 06475, 2 beds, 1.5 baths

$519,000

2 beds1.5 baths1,557 sq ft

118 Sandy Point Rd #118, Old Saybrook, CT 06475

Property at 125 Main St, Old Saybrook, CT 06475, 1 bed, 1.5 baths

$2,195,000

1 bed1.5 baths7,985 sq ft

125 Main St, Old Saybrook, CT 06475

Property at 6 South St, Old Saybrook, CT 06475

$159,900

— beds— baths— sq ft

6 South St, Old Saybrook, CT 06475

Property at 81 Essex Rd, Old Saybrook, CT 06475

$649,000

— beds— baths— sq ft

81 Essex Rd, Old Saybrook, CT 06475

Property at 396 Middlesex Tpke, Old Saybrook, CT 06475

$399,000

— beds— baths— sq ft

396 Middlesex Tpke, Old Saybrook, CT 06475

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Average home prices near Old Saybrook, CT

Cities

Zip Codes
Minor Civil Divisions

Old Saybrook, CT real estate trends

$670K

Sale price

-27.2%
since last year

$351

Sale $/sq ft

-25.3%
since last year

Under list price

2.3%

Days on market

Down payment

—

Total homes sold

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